Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Hetero Ring Patents (Class 549/402)
  • Patent number: 6350431
    Abstract: This invention provides a physiologically tolerable light imaging contrast agent compound having a molecular weight in the range 500 to 5000000 and containing at least two chromophores having delocalized electron systems as well as at least one polyalkylene oxide (PAO) moiety having a molecular weight in the range 60 to 100000.
    Type: Grant
    Filed: October 28, 1999
    Date of Patent: February 26, 2002
    Assignee: Nycomed Imaging AS
    Inventors: Robert Allen Snow, Paul Mark Henrichs, Daniel Joseph Delecki, William Anthony Sanderson, Vinay Chandrakant Desai, Edward Bacon, Kenneth Robert Hollister, Eric Paul Hohenschuh
  • Patent number: 6331640
    Abstract: A compound of formula 1a which is useful for treating reperfusion injury, and salts, prodrugs, and related compounds.
    Type: Grant
    Filed: September 29, 1999
    Date of Patent: December 18, 2001
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Nader Fotouhi, Paul Gillespie, Robert William Guthrie, Sherrie Lynn Pietranico-Cole, Weiya Yun
  • Patent number: 6291518
    Abstract: The present invention relates to novel hydroxy and polyhydroxy derivatives of coumarin fused with dialdehydes and aldehyde acids of the general formulae I, II, III and IV: wherein R1=R2=4-hydroxycoumarin; R1=R2=4,7-dihydroxycoumarin; R1=R2=4,5,7-trihydroxycoumarin; R1=4-hydroxycoumarin, R2=—CH(OH)CH3. An object of the invention are also processes for the preparation of hydroxy and polyhydroxy derivatives of coumarin fused with dialdehydes and aldehyde acids, and the antiviral action thereof. Novel hydroxy and polyhydroxy derivatives of coumarin according to the present invention exhibit antiviral action against HIV-1 virus.
    Type: Grant
    Filed: January 3, 2000
    Date of Patent: September 18, 2001
    Assignee: Pliva farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvo
    Inventors: Mladen Trkovnik, Zrinka Ivezić
  • Patent number: 6265423
    Abstract: Novel aromatic polycyclic retinoid-type derivatives of general formula (I), wherein groupings R3 and R4 attached to the double bond between carbons 11 and 12 are cis groupings, and pharmaceutical and cosmetic compositions containing same, are disclosed.
    Type: Grant
    Filed: July 15, 1998
    Date of Patent: July 24, 2001
    Assignee: Centre Europeen de Bioprospective-Ceb
    Inventors: Bertrand Leblond, Francis Darro, Abdallah Devine, Véronique Sales-Sallans, Pierre Duhamel, Robert Kiss, Alain-René Schoofs, Pierre Germain, Bernard Pourrias
  • Patent number: 6262108
    Abstract: The cromoglycic acid compound of the formula (I) has an antirheumatic action, an antiinflammatory action and an immunomodulating action. This compound is effective for the inhibition of the symptoms of chronic rheumatoid arthritis and is associated with fewer side effects. Therefore, the antirheumatic agent of the present invention can be used beneficially for the treatment of rheumatoid arthritis. In addition, this compound has anti-type I and anti-type IV allergic activities. Therefore, the compound can be used beneficially mainly for the treatment of allergic dermatitis, in which a type IV allergic reaction is involved, such as contact dermatitis, in which a type IV allergic reaction is involved, atopic dermatitis, in which type I and type IV allergic reactions are involved and the like.
    Type: Grant
    Filed: July 28, 2000
    Date of Patent: July 17, 2001
    Assignee: Kyoto Pharmaceutical Industries, Ltd.
    Inventors: Hiroaki Shirahase, Akihisa Yoshimi, Shohei Nakamura, Mamoru Kanda, Fumio Fukata
  • Patent number: 6225481
    Abstract: Robustaflavone, intermediates and analogues thereof and a method for synthesizing the same are provided. The method involves constructing apigenin ethers containing functionalities at the 6- and 3′-positions which could be cross-coupled using transition metal catalysis. The method also involves development of a regioselective iodination of an apigenin derivative at the 6-position, formation of an apigenin 3′-boronate using a palladium-catalyzed exchange of the corresponding 3′-iodide with a diboron reagent. Finally, Suzuki coupling to form the sterically congested 6-3′″ biaryl bond of robustaflavone provides access to the desired biflavanoid system. Robustaflavone intermediates and analogues may be used to prepare analogues of other biflavanoids such as hinokifavone, rhusflavone and succedaneaflavone.
    Type: Grant
    Filed: August 21, 1998
    Date of Patent: May 1, 2001
    Assignee: Advanced Life Sciences, Inc.
    Inventors: David E. Zembower, Heping Zhang, Michael T. Flavin, Yuh-Meei Lin
  • Patent number: 6218427
    Abstract: The present invention provides a compound of the formula (I): wherein R1, R2, R3 and R4 are each independently hydrogen, optionally substituted alkyl, hydroxy, optionally substituted alkoxy or the like, R5 is optionally substituted alkyl, optionally substituted aryl, optionally substituted heterocyclic or the like, R6 is hydrogen, optionally substituted alkyl or the like, R7 is hydrogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heterocyclic or the like, A is S or O and a broken line represents presence or absence of a bond, pharmaceutically acceptable salt or hydrate thereof and a pharmaceutical composition or a pharmaceutical composition for use as an endothelin receptor antagonist, a peripheral circulation insufficiency-improving agent or a macrophage foam cell formation inhibitor comprising the compound.
    Type: Grant
    Filed: April 26, 1999
    Date of Patent: April 17, 2001
    Assignee: Shionogi & Co., Ltd.
    Inventors: Natsuki Ishizuka, Ken-ichi Matsumura, Katsunori Sakai, Toshiro Konoike, Tadahiko Yorifuji, Seijiro Hara, Yoshiyuki Matsuo
  • Patent number: 6191289
    Abstract: There are disclosed an industrially favorable process for producing a tetrazole compound of general formula (1): characterized in that a nitrile of general formula (2): R1CN  (2) is reacted with hydrazine or a salt thereof in the presence of a catalyst, followed by reaction with a nitrous acid compound of general formula (3): ANO2  (3) or a nitrile of general formula (2) is reacted with hydrogen sulfide, followed by reaction with an alkyl halide of general formula (4): R4J  (4) with hydrazine or a salt thereof, and then with a nitrous acid compound of general formula (3); and an intermediate of general formula (5): R1C(═R5)R6  (5) which is useful for the production of the tetrazole compound (in which R1 to R6, A and J in the above formulas are as defined in the specification).
    Type: Grant
    Filed: October 21, 1998
    Date of Patent: February 20, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hideki Ushio, Takayuki Higashii, Masayoshi Minai, Akihiko Nakamura
  • Patent number: 6066642
    Abstract: The present invention provides certain novel compounds, compositions, and a method of treating a mammal by blocking its adenosine receptors comprising administering at least one compound of the present invention. Examples of the present inventive compounds include certain flavonoids of formulae (I) and (II), wherein R.sub.1 to R.sub.4 are as defined in the description, and M is --CH(OH)--CH(R.sub.2)-- or --C(OH).dbd.C(R.sub.2)-- and R.sub.1, R.sub.2 are as defined in the description; or dihydropyridines of formula (III), wherein R.sub.2 to R.sub.6 are as defined in the description; or pyridines of formula (IV), wherein R.sub.2 to R.sub.6 are as defined in the description, or triazoloquinazolines of formula (V), wherein R.sub.1 and R.sub.2 are as defined in the description; and their derivatives, or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: December 7, 1998
    Date of Patent: May 23, 2000
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Kenneth A. Jacobson, Ji-Long Jiang, Yong-Chul Kim, Yishai Karton, Albert M. Van Rhee
  • Patent number: 6051601
    Abstract: This invention relates to novel benzopyran and other benzo-fused leukotriene B.sub.4 (LTB.sub.4) antagonists and the pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing such compounds or a pharmaceutically acceptable salt thereof, and to methods of using such compounds as LTB.sub.4 antagonists. The compounds and the pharmaceutically acceptable salts of this invention inhibit the action of LTB.sub.4 and are therefore useful in the treatment of LTB.sub.4 induced illnesses such as inflammatory disorders including rheumatoid arthritis, osteoarthritis, inflammatory bowel disease, psoriasis and other skin disorders such as eczema, erythema, pruritus and acne, stroke and other forms of reperfuslon injury, graft rejection, autoimmune diseases, asthma, and other conditions where marked neutrophil infiltration occurs.
    Type: Grant
    Filed: April 9, 1997
    Date of Patent: April 18, 2000
    Assignee: Pfizer Inc.
    Inventors: Mark Anthony Dombroski, Kevin Koch, Anthony Daniel Piscopio
  • Patent number: 6004998
    Abstract: Certain flavonoids, notably derivatives of flavone, chrysin and apigenin, together with dimers thereof such as amentoflavone, have been found to possess anxiolytic properties (i.e., anxiety reducing properties) without exhibiting a sedative effect. Novel compounds and pharmaceutical formulations are also described.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: December 21, 1999
    Assignee: University of Strathclyde
    Inventors: Bruce Kennedy Cassels, Federico Jose Dajas, Jorge Horacio Medina, Alejandro Constantino Paladini, Rodolfo Horacio Silveira
  • Patent number: 5990142
    Abstract: The present invention relates to novel 4-oxo-4H-1-benzopyran compounds containing benzyloxymethyl, 3-phenylpropyl, or other araliphatic substituents in their 8-position. These compounds show a leukotriene-antagonistic activity. The compounds are characterized by good oral adsorption. The compounds of the present invention may be used as anti-inflammatory and antiallergic medicaments, and in the treatment of cardiovascular diseases.
    Type: Grant
    Filed: October 15, 1998
    Date of Patent: November 23, 1999
    Assignee: Laboratorios Menarini S.A.
    Inventors: Germano Carganico, David Mauleon Casellas, Jaime Pascual Avellana, M. Luisa Garcia Perez, Albert Palomer Benet
  • Patent number: 5919829
    Abstract: Compounds of formula (Ia), (Ib), or (Ic), wherein A represents a group having two fused rings, or a group of formula (Id), R.sup.1.sub.(m) represents up to 6 substituents, K represents --O--, --S--, --CH.sub.2 --, --N(R.sup.2)-- or --N(COR.sup.2)--, in which R.sup.2 is H or C.sub.1 to C.sub.3 alkyl, W is a carbonyl, sulfonyl or sulfinyl group, provided that at least one of W and X contains carbonyl, Y and Z are as given in the description, and their pharmaceutically acceptable salts are ligands at CCK and/or gastrin receptors.
    Type: Grant
    Filed: April 23, 1998
    Date of Patent: July 6, 1999
    Assignee: James Black Foundation Limited
    Inventors: Sarkis Barret Kalindjian, Katherine Isobel Mary Steel, Michael John Pether, Jonathan Michael Richard Davies, Caroline Minli Rachel Low, Martin Lyn Hudson, Ildiko Maria Buck, Iain Mair McDonald, David John Dunstone, Matthew John Tozer
  • Patent number: 5874593
    Abstract: There are disclosed an industrially favorable process for producing a tetrazole compound of general formula (1): ##STR1## characterized in that a nitrile of general formula (2):R.sup.1 CN (2)is reacted with hydrazine or a salt thereof in the presence of a catalyst, followed by reaction with a nitrous acid compound of general formula (3):ANO.sub.2 (3)or a nitrile of general formula (2) is reacted with hydrogen sulfide, followed by reaction with an alkyl halide of general formula (4):R.sup.4 J (4)with hydrazine or a salt thereof, and then with a nitrous acid compound of general formula (3); and an intermediate of general formula (5):R.sup.1 C(=R.sup.5)R.sup.6 (5)which is useful for the production of the tetrazole compound (in which R.sup.1 to R.sup.6, A and J in the above formulas are as defined in the specification).
    Type: Grant
    Filed: February 8, 1996
    Date of Patent: February 23, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hideki Ushio, Takayuki Higashii, Masayoshi Minai, Akihiko Nakamura
  • Patent number: 5851792
    Abstract: An aglucone isoflavone enriched vegetable protein whey, whey protein material, high genistein material, high daidzein material, and aglucone isoflavone material are provided, as well as a process for producing the same from a vegetable protein whey. Isoflavone conjugates in a vegetable protein whey are converted to isoflavone glucosides by treating the whey at a temperature and a pH for a period of time sufficient to effect the conversion. The isoflavone glucosides are converted to aglucone isoflavones by enzymatic reaction to produce an aglucone isoflavone enriched vegetable protein whey. Aglucone isoflavone whey protein material is recovered from the aglucone isoflavone enriched vegetable protein whey. A high genistein content material, a high daidzein content material, and an aglucone isoflavone material are produced from an alcohol extract of the aglucone isoflavone whey protein material.
    Type: Grant
    Filed: April 3, 1996
    Date of Patent: December 22, 1998
    Inventors: Jerome Shen, Mark A. Roussey, Barbara A. Bryan, Maryann C. Allred
  • Patent number: 5827682
    Abstract: Disclosed are methods for converting isoflavone conjugates in vegetable protein materials to isoflavone aglucones by forming an aqueous mixture of a vegetable protein material containing isoflavone conjugates, converting the isoflavone conjugates to isoflavone glucones, and converting the isoflavone glucones to isoflavone aglucones. The vegetable protein material may also contain isoflavone glucones which are converted to isoflavone aglucones. The isoflavone conjugates, isoflavone glucones, or isoflavone aglucones present in the vegetable protein material may be removed from the vegetable materials before, during, or after the conversion process.
    Type: Grant
    Filed: October 15, 1996
    Date of Patent: October 27, 1998
    Assignee: Protein Technologies International, Inc.
    Inventors: Barbara A. Bryan, Maryann C. Allred, Mark A. Roussey
  • Patent number: 5756538
    Abstract: Certain flavonoids, notably derivatives of flavone, chrysin and apigenin, together with dimers thereof such as amentoflavone, have been found to possess anxiolytic properties (i.e., anxiety reducing properties) without exhibiting a sedative effect. Novel compounds and pharmaceutical formulations are also described.
    Type: Grant
    Filed: May 31, 1996
    Date of Patent: May 26, 1998
    Assignee: University of Strathclyde
    Inventors: Bruce Kennedy Cassels, Federico Jose Dajas, Jorge Horacio Medina, Alejandro Constantino Paladini, Rodolfo Horacio Silveira
  • Patent number: 5726034
    Abstract: An aglucone is isoflavone enriched vegetable protein extract and protein material are provided, as well as a high genistein content material and a high daidzein content material. Isoflavone conjugates in a vegetable material are converted to isoflavone glucosides by treating the vegetable material at a temperature and a pH for a period of time sufficient to effect the conversion. The isoflavone glycosides are converted to glucose isoflavones by enzymatic reaction. The vegetable material is extracted with an aqueous extractant having a pH above about the isoelectric point of protein in the vegetable material to extract protein and the isoflavones either before or after conversion of the isoflavone conjugates to isoflavone glucosides or the conversion of the isoflavone glucosides to aglucone isoflavones. An aglucone isoflavone enriched protein material is produced by precipitating the protein and aglucone isoflavones from the extract.
    Type: Grant
    Filed: September 6, 1996
    Date of Patent: March 10, 1998
    Assignee: Protein Technologies International, Inc.
    Inventors: Barbara A. Bryan, Maryann C. Allred
  • Patent number: 5672723
    Abstract: The present invention can provide a process for the preparation of an 1-acyl-2-substituted hydrazine compound from a mixture containing the 1-acyl-2-substituted hydrazine and an 1-acyl-1-substituted hydrazine by selective hydrolysis or alcoholysis of the 1-acyl-yl-1-substituted hydrazine in the presence of an acid catalyst, and by separation of the resulting carboxylic acid and derivative thereof.The 1-acyl-2-alkyl hydrazine obtained has a high purity.
    Type: Grant
    Filed: February 21, 1996
    Date of Patent: September 30, 1997
    Assignees: Nippon Kayaku Kabushiki Kaisha, Sankyo Company, Limited
    Inventors: Hiroki Hotta, Hiroyasu Sugizaki, Tetsuya Toya, Mikio Yanagi
  • Patent number: 5659051
    Abstract: There is disclosed a process of producing a 2-cyano-4-oxo-4H-benzopyran compound of the general formula (2): ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen, hydroxy, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro or a group of the RCONH wherein R is C.sub.1 -C.sub.20 alkyl, phenyl, phenyl-substituted (C.sub.1 -C.sub.20) alkyl, phenyl (C.sub.1 -C.sub.20)alkoxyphenyl or (C.sub.1 -C.sub.20) alkoxyphenyl. This production process is characterized in that a carboxamide of the general formula (1): ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above, is reacted with a dehydrating agent in the presence of a pyridine compound of the general formula (4): ##STR3## wherein A.sup.1 and A.sup.2 are independently hydrogen or C.sub.1 -C.sub.5 alkyl.
    Type: Grant
    Filed: July 11, 1994
    Date of Patent: August 19, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Hideki Ushio, Yukari Fujimoto, Tsutomu Matsumoto, Masayoshi Minai, Katsuichi Yasunaga, Hiroshi Sogabe, Takahiro Kotera
  • Patent number: 5639783
    Abstract: A novel ketone derivative (I) which possesses a potent inhibitory activity against thiol protease such as papain, cathepsin B, cathepsin H, cathepsin L, calpain or the like with excellent properties regarding oral absorbance, tissue transference and cell membrane permeability, and are clinically useful in the treatment of various diseases such as muscular dystrophy, amyotrophy. Also provided are a process for producing the compound (I) and a pharmaceutical composition containing the same.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: June 17, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Ryoichi Ando, Naoko Ando, Hirokazu Masuda, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
  • Patent number: 5508451
    Abstract: A process for preparing a dialkali metal cromoglycate which comprises (1) condensing a hydroxy substituted ketone with a condensing agent in the presence of a base material and an organic solvent; (2) subjecting the condensed material to ring-closure conditions, first in the presence of an alkali metal alkoxide and a suitable organic solvent, then followed by the addition of substantially dry mineral acid and a suitable organic solvent; and (3) hydrolyzing the ring-closed material in the presence of a base material and a suitable organic solvent to form said cromoglycate.
    Type: Grant
    Filed: July 7, 1994
    Date of Patent: April 16, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: Apurba Bhattacharya, Boyd A. Keys
  • Patent number: 5420307
    Abstract: 2-Amino-4-oxo-4H-benzopyrans I ##STR1## (m=0, 1 or 2; R.sup.1 -R.sup.4 have the meanings stated in the description) and the salts of I, and herbicides which contain 2-(4-hetaryloxy)- and 2-(4-aryloxy)-phenoxyacetic acid derivatives and/or cyclohexenone derivatives as herbicidal active ingredients and 2-amino-4-oxo-4H-benzopyrans I' as antidotes.
    Type: Grant
    Filed: June 7, 1993
    Date of Patent: May 30, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hagen, Gerhard Nilz, Helmut Walter, Andreas Landes, Wolfgang Freund
  • Patent number: 5352690
    Abstract: This invention provides 1,2,4-trioxygenated benzene derivatives which are leukotriene B.sub.4 antagonists, formulations of those derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.
    Type: Grant
    Filed: July 1, 1992
    Date of Patent: October 4, 1994
    Assignee: Eli Lilly and Company
    Inventor: Michael J. Sofia
  • Patent number: 5348973
    Abstract: Hydroxychroman-2-carboxylic acid esters can be resolved by enantiospecific hydrolysis by the use of liver enzymes, particularly solvent treated (acetone) enzymes. Liver enzymes from calf, cat, dog, eel, goat, lungfish, mouse, rat and seal have been found to be enantiospecific.
    Type: Grant
    Filed: October 9, 1990
    Date of Patent: September 20, 1994
    Assignee: Rhone-Poulenc Chimie
    Inventors: Muppala S. Raju, Namdol Huh
  • Patent number: 5324743
    Abstract: This invention provides certain 1,2,4,5 substituted benzene derivatives containing "acid" substituents derived from cyclic or heterocyclic moieties. These unique compounds are leukotriene B.sub.4 antagonists and formulations of these derivatives, and a method of using these derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.
    Type: Grant
    Filed: December 10, 1992
    Date of Patent: June 28, 1994
    Assignee: Eli Lilly and Company
    Inventors: Robert D. Dillard, J. Scott Sawyer, Michael J. Sofia
  • Patent number: 5320949
    Abstract: The present invention relates to an aglucone isoflavone enriched vegetable protein fiber wherein a vegetable protein material is extracted to form a slurry of protein, fiber and glucone isoflavones. The pH of the slurry is adjusted to about 6 to 8 and the slurry reacted with a beta glucosidase to convert the glucone isoflavones in said slurry to aglucone isoflavones. The fiber fraction is then recovered from the slurry by centrifugation or similar means to provide an aglucone enriched fiber.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: June 14, 1994
    Assignee: Protein Technologies International, Inc.
    Inventor: Jerome L. Shen
  • Patent number: 5223532
    Abstract: Non-peptidyl compounds characterized generally as chromonyl/chromonylalkyl-N-terminal cycloalkoxy-C-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from ##STR2## wherein each of Y and Z is independently selected from hydrido, chloro, fluoro, methoxy and dimethylamino; wherein n is a number selected from zero through four, inclusive; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 and R.sub.7 are taken together to form a partially saturated or fully saturated heterocyclic ring containing five to eight ring members with one or two ring members being oxygen atoms and the remaining ring members being carbon atoms, and which heterocyclic ring may be optionally substituted with lower alkyl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: June 29, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
  • Patent number: 5210095
    Abstract: Non-peptidyl compounds characterized generally as chromonyl/chromonylalkyl-N-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from ##STR2## wherein each of Y and Z is independently selected from hydrido, chloro, fluoro, methoxy and dimethylamino; wherein Q is oxygen atom; wherein n is a number selected from zero through four, inclusive; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; and wherein R.sub.7 is isobutyl or ethyl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: July 29, 1991
    Date of Patent: May 11, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
  • Patent number: 5171865
    Abstract: A process for the preparation of optically active 4-oxo-1-benzopyran-2-carboxylic acid derivatives of the formula ##STR1## wherein X and Y are hydrogen atom, halogen atom or alkyl group, and R.sub.1 is hydrogen atom or alkyl group,intermediates thereof, as well as a process for the preparation of the intermediates.
    Type: Grant
    Filed: March 5, 1991
    Date of Patent: December 15, 1992
    Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.
    Inventors: Masayasu Kurono, Yasuaki Kondo, Kenji Miura, Toshinao Usui, Ryoichi Unno, Takuji Kakigami, Kiichi Sawai
  • Patent number: 5149717
    Abstract: Substituted alkanophenones of general formula ##STR1## in which R.sub.1 is unsubstituted or fluorinated lower alkyl, R.sub.2 is hydrogen, or unsubstituted or fluorinated lower alkyl or lower alkenyl, X is lower alkylene, oxy, thio or a direct bond, alk is lower alkylene, n is 1 or 2, R.sub.3 is phenyl that is unsubstituted or is substituted by unsubstituted or fluorinated lower alkyl, by etherified or esterified hydroxy, by unsubstituted or lower alkylated amino and/or by free, esterified or amidated carboxy, or is lower alkyl that is unsubstituted, substituted by fluoro and chloro or substituted by free esterified or amidated carboxy, R.sub.4 is free, esterified or amidated carboxy or 5-tetrazolyl, and R.sub.5 is hydrogen or lower alkyl, have leucotriene-antagonistic properties and can be used as anti-allergic active ingredients in medicaments.
    Type: Grant
    Filed: November 15, 1991
    Date of Patent: September 22, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas von Sprecher, Andreas Beck, Bruno Schaub, Robert W. Lang
  • Patent number: 5145868
    Abstract: Substituted alkanophenones of the general formula ##STR1## in which R.sub.1 is unsubstituted or fluorinated lower alkyl, R.sub.2 is hydrogen, or unsubstituted or fluorinated lower alkyl or lower alkenyl, X is lower alkylene, oxy, thio or a direct bond, alk is lower alkylene, n is 1 or 2, R.sub.3 is a 5-membered heteroaryl radical that contains 1N, O or S atom as hetero atom and is unsubstituted or is substituted by unsubstituted or fluorinated lower alkyl, by etherified or esterified hydroxy, by unsubstituted or lower alkylated amino and/or by free, esterfied or amidated carboxy, R.sub.4 is free, esterified or amidated carboxy or 5-tetrazolyl, and R.sub.5 is hydrogen or lower alkyl, have leucotriene-antagonistic properties can e used as antiallergic active ingredients in medicaments.
    Type: Grant
    Filed: November 15, 1991
    Date of Patent: September 8, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas von Sprecher, Andreas Beck
  • Patent number: 5017583
    Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are leukotriene antagonists. These compounds inhibit SRS-A and leukotriene synthesis and are antagonists of SRS-A and are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.
    Type: Grant
    Filed: February 23, 1988
    Date of Patent: May 21, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
  • Patent number: 5013852
    Abstract: Flavone-3-carboxylic acid compounds corresponding to the Formula I: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 represent hydrogen, lower alkyl, halogen, hydroxy, or etherified or esterified hydroxy, and Z-R.sup.6 stands for a basically substituted alkoxy or amino group, as well as processes and intermediate products for their production. The compounds exhibit inflammation-inhibiting pharmacological activity.
    Type: Grant
    Filed: May 18, 1989
    Date of Patent: May 7, 1991
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Rainer Walenta, Reiner Muller-Peddinghaus, Ivan Ban, Michael Wurl, Ulf Preuschoff
  • Patent number: 4985573
    Abstract: Hydantoin derivatives and salts thereof, intermediates therefor, process for the preparation thereof, and medicines containing the derivative, wherein said derivatives have the formula ##STR1## wherein one of V and W is hydrogen and the other is a halogenomethyl group, 1H-tetrazol-5-yl radical, --COOR group, in which R is hydrogen atom, an alkyl group, --(CH.sub.2 CH.sub.2 O)nCH.sub.3 group (n is an integer of 1 to 113) or substituted phenyl, ##STR2## in which R.sub.1 and R.sub.2 are same or different independently, each is hydrogen atom, an alkyl group, substituted phenyl or --(CH.sub.2 CH.sub.2 O)nCH.sub.3 group (n has the meaning as referred to) or R.sub.1 may form a heterocyclic ring together with R.sub.2 and nitrogen or oxygen atom, ##STR3## in which R.sub.3 and R.sub.
    Type: Grant
    Filed: May 23, 1989
    Date of Patent: January 15, 1991
    Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.
    Inventors: Masayasu Kurono, Yasuaki Kondo, Takuji Yamaguchi, Kenji Miura, Toshinao Usui, Naofumi Terada, Kyoichi Asano, Kuniharu Mizuno, Akira Matsubara, Noriaki Kato, Kiichi Sawai, Ryoichi Unno, Hiroshi Ozawa, Masato Fukushima
  • Patent number: 4985574
    Abstract: Hydantoin derivatives and salts thereof, intermediates therefor, process for the preparation thereof, and medicines containing the derivative, wherein said derivatives have the formula ##STR1## wherein one of V and W is hydrogen and the other is a halogenomethyl group, 1H-tetrazol-5-yl radical, --COOR group, in which R is hydrogen atom, an alkyl group, --(CH.sub.2 CH.sub.2 O)nCH.sub.3 group (n is an integer of 1 to 113) or substituted phenyl, ##STR2## in which R.sub.1 and R.sub.2 are same or different independently, each is hydrogen atom, an alkyl group, substituted phenyl or --(CH.sub.2 CH.sub.2 O)nCH.sub.3 group (n has the meaning as referred to) or R.sub.1 may form a heterocyclic ring together with R.sub.2 and nitogen or oxygen atom, ##STR3## in which R.sub.3 and R.sub.
    Type: Grant
    Filed: November 22, 1989
    Date of Patent: January 15, 1991
    Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.
    Inventors: Masayasu Kurono, Yasuaki Kondo, Takuji Yamaguchi, Kenji Miura, Toshinao Usui, Naofumi Terada, Kyoichi Asano, Kuniharu Mizuno, Akira Matsubara, Noriaki Kato, Kiichi Sawai, Ryoichi Unno, Hiroshi Ozawa, Masato Fukushima
  • Patent number: 4985429
    Abstract: Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives, such as l-N-[3-(2,3-dihydro-1-oxo-1H-inden-5-yl)-2-oxooxazolidin-5-ylmethyl]acetam ide, possess useful antibacterial activity.
    Type: Grant
    Filed: March 15, 1990
    Date of Patent: January 15, 1991
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Chia-Lin J. Wang, Mark A. Wuonola
  • Patent number: 4954518
    Abstract: This invention relates to a 4H-1-benzopyran-4-one derivative represented by the formula: ##STR1## or a salt thereof, a process for producing the same and a pharmaceutical composition comprising the same as active ingredient.
    Type: Grant
    Filed: October 7, 1988
    Date of Patent: September 4, 1990
    Assignee: Toyama Chemical Company, Ltd.
    Inventors: Shuntaro Takano, Chosaku Yoshida, Takihiro Inaba, Keiichi Tanaka, Ryuko Takeno, Hideyoshi Nagaki, Tomoya Shimotori, Shinji Makino
  • Patent number: 4889871
    Abstract: This invention encompasses compounds of Formula 1 and the pharmaceutically acceptable salts thereof. ##STR1## wherein R.sup.1 represents alkyl having 2-6 carbon atoms;R.sup.2 represents methyl or ethyl;R.sup.3 represents alkyl having 1 to 5 carbon atoms;W represents (CH.sub.2).sub.x where x is 2 to 7, alkylene having 2 to 7 carbon atoms, alkenylene having 3 to 7 carbon atoms, alkynylene having 3 to 7 carbon atoms, or cyclopentyl;R.sup.4 represents hydrogen, alkyl having 2-5 carbon atoms, alkenyl having 2 to 5 carbon atoms, or alkynyl having 2 to 5 carbon atoms;Q represents oxygen or CH.sub.2 ;B represents CH.sub.2, C.dbd.O or CH--OH;R.sup.5 represents hydrogen, alkyl having 1 to 6 carbon atoms, or R.sup.5 and R.sup.6 together optionally represent a carbon to carbon bond; orR.sup.5 represents alkanoyl having 2 to 4 carbon atoms, carboxy, alkoxycarbonyl, or (CH.sub.2)y--CO.sub.2 R.sup.8 wherein y is 0 to 4 and R.sup.8 is hydrogen or alkyl having 1 to 6 carbon atoms; andA represents --Z--CO.sub.2 R.sup.
    Type: Grant
    Filed: May 12, 1988
    Date of Patent: December 26, 1989
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Robert L. Shone, Stella S. T. Yu
  • Patent number: 4886546
    Abstract: A compound of the formula (I) ##STR1## wherein (1) when R.sub.1 is a C.sub.2-11 alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aralkyl which may be substituted, a lower haloalkyl or a 5 or 6 membered heterocycle;R.sub.2, R.sub.3 and R.sub.4 are the same or different, hydrogen, a halogen, cyano, nitro, amino, a lower alkyl, a lower haloalkyl, hydroxy, a lower alkoxy, an aryloxy, carboxy, or a lower alkoxycarbonyl;R.sub.5 is hydrogen, a halogen, a C.sub.1-11 alkyl, an aryl which may be substituted, an aralkyl which may be substituted;R.sub.6 is a C.sub.1-11 alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aryl which may be substituted, an aralkyl which may be substituted, a lower haloalkyl, or a 5 or 6 membered heterocycle; or R.sub.5 and R.sub.6 may be combined to form a group of --(CH.sub.2).sub.m -- (m is 3 or 4);(2) when R.sub.1 is an aryl which may be substituted;R.sub.2, R.sub.3, R.sub.4 and R.sub.5 have the same meanings as defined above; R.
    Type: Grant
    Filed: March 11, 1987
    Date of Patent: December 12, 1989
    Assignee: Daicel Chemical Industries Ltd.
    Inventors: Hiroshi Yagihara, Yukihisa Goto, Kazuhisa Masamoto, Yasuo Morishima, Hirokazu Osabe
  • Patent number: 4868205
    Abstract: The present invention relates to novel enolamide type compounds, pharmaceutical compositions, and methods of use thereof, useful in the treatment of diseases in which products of lipoxygenase enzyme activity or the action of leukotrienes contribute to the pathological condition.
    Type: Grant
    Filed: March 11, 1988
    Date of Patent: September 19, 1989
    Assignee: Warner-Lambert Company
    Inventors: Mary E. Carethers, Wiaczeslaw A. Cetenko, David T. Connor, Elizabeth A. Johnson, John S. Kiely, Charles F. Schwender, Jagadish C. Sircar, Roderick J. Sorenson, Paul C. Unangst, Robert F. Bruns
  • Patent number: 4855443
    Abstract: An antiinflammatory derivative of chromoglycic acid having the formula ##STR1## The process for the prepartion thereof is based on the reaction of chromoglycic acid, or a salt thereof, with benzidamine in a polar solvent.
    Type: Grant
    Filed: July 26, 1988
    Date of Patent: August 8, 1989
    Assignee: Laboratorios Vinas S. A.
    Inventor: Antonio Buxade-Vinas
  • Patent number: 4847286
    Abstract: Cromoglycic acid derivatives of the general formula ##STR1## wherein R.sup.1 is an .alpha.-, .beta.- or .gamma.-amino acid residue (for ester bonding) whose amino group may optionally be substituted by at least one lower alkyl group, and R.sup.2 and R.sup.3 each independently is a lower alkyloxy-substituted or an unsubstituted lower alkyl group, an 1-alkanoyloxyalkyl group, an 1-alkoxycarbonyloxyalkyl group, a phthalidyl group or a 5-methyl-1,3-dioxol-2-on-4-ylmethyl group; nontoxic salts thereof; and pharmaceutical compositions containing such compounds. Since the compounds have antiallergic activity and are readily absorbable into the blood stream, they are useful as oral antiallergic agents.
    Type: Grant
    Filed: March 27, 1987
    Date of Patent: July 11, 1989
    Assignee: Kyoto Pharmaceutical Industries, Ltd.
    Inventors: Satoshi Tamaki, Masaru Kitagawa, Hirokazu Tsuda, Susumu Nishizawa, Nobuhara Kakeya, Kazuhiko Kitao
  • Patent number: 4841078
    Abstract: Bicyclic fused benzenoid compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, where M is O, CH.sub.2 or NR.sub.6 ; R.sub.6 is hydrogen, formyl, carbobenzyloxy or certain carboalkoxyalkyl, alkanoyl, alkyl, aralkyl or aralkylcarbonyl groups;A' is:(1) A where one of A and B is hydrogen such that when A is hydrogen, B is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 1 or 2; when B is hydrogen, A is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 0 or 1, when taken together A and OR.sub.1 form a lactone or certain derivatives thereof;(2) A' is ##STR2## (3) A' is Q.sub.3 ; Q is CO.sub.2 R.sub.7, COR.sub.8, C(OH)R.sub.8 R.sub.9, CN, CONR.sub.12 R.sub.13, CH.sub.2 NR.sub.12 R.sub.13, CH.sub.2 NHCOR.sub.14, CH.sub.2 NHSO.sub.2 R.sub.17 or 5-tetrazoyl;Q.sub.3 is ##STR3## 5-tetrazolyl, CH.sub.2 CONHCOR.sub.7, COOH or certain ester, amide, carboximido or sulfonimido derivatives thereof, CONHOH, CONHCONH.sub.2, or COCH.sub.2 Q.sub.4 where Q.sub.
    Type: Grant
    Filed: August 9, 1984
    Date of Patent: June 20, 1989
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Michael R. Johnson, Lawrence Sherman
  • Patent number: 4841077
    Abstract: Novel isoflavone derivatives are provided which have the formula ##STR1## and which exhibit cancerocidal and immunosuppressive activity. The invention also provides pharmaceutical compositions containing the derivatives, methods of use and processes for their preparation.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: June 20, 1989
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Noriki Ito, Hiroshi Ogawara, Shunichi Watanabe
  • Patent number: 4785004
    Abstract: Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: R.sup.0 represents hydrogen or C.sub.1-7 -alkanoyl,R.sup.1 represents C.sub.1-3 -alkyl which may be substituted by one or more halogen atoms having an atomic number of at most 17,R.sup.2 represents an aliphatic radical having from 5 to 15 carbon atoms,A represents ethylene, a single bond or vinylene,B.sup.1 represents C.sub.1-7 -alkylene or phenylene,B.sup.2 represents a single bond, ethylene or phenylene, andM represents an aromatic radical of the partial formula ##STR2## in which the symbols have the following meanings: R.sup.3 represents hydrogen or C.sub.1-4 -alkyl,X represents NH, O, S or if R.sup.4 represents hydrogen, a single bond,one of the symbols R.sup.4 and R.sup.5 represents hydrogen and the other represents the group --CO--R.sup.6, orR.sup.4 and R.sup.5 together represent the radical --CO--C(R.sup.6).dbd.C(R.sup.7)--or--CO--C(R.sup.7).dbd.C(R.sup.6)--orR.sup.4 R.sup.
    Type: Grant
    Filed: December 15, 1986
    Date of Patent: November 15, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Von Sprecher, Werner Breitenstein, Andreas Beck, Robert W. Lang, Konrad Oertle
  • Patent number: 4780469
    Abstract: A (fused) benz(thio)amide of the formula: ##STR1## wherein B represents(i) a carbocyclic ring of from 4 to 8 members being unreplaced or replaced one, two or three of optional carbon atom(s) by oxygen, nitrogen and/or sulphur atom(s) or(ii) a divalent group of the formula: ##STR2## R.sup.1 represents a group of formula: ##STR3## (iv) a straight or branched alkyl, alkenyl, or alkynyl of from 1 to 20 carbon atoms,R.sup.4 represents(i) when B represents a closed ring, a group of the formula: ##STR4## (ii) when B does not represent a ring, a group of formula: ##STR5## with the proviso that compounds of formula: ##STR6## wherein A' is a vinylene or an ethylene group optionally substituted by straight or branched alkyl groups of from 1 to 4 carbon atom(s);R.sup.4' is--(CH.sub.2).sub.n --COOR.sup.8andR.sup.1' is(i) a group of the formula: ##STR7## or (ii) a group of the formula: ##STR8## are excluded, wherein A, R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, U, n, m, p, q, R.sup.5', and R.sup.
    Type: Grant
    Filed: August 20, 1985
    Date of Patent: October 25, 1988
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Masaaki Toda, Tumoru Miyamoto, Yoshinobu Arai
  • Patent number: 4761425
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory agents, and cytoprotective agents.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: August 2, 1988
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Yves Girard, Joshua Rokach
  • Patent number: 4665203
    Abstract: The invention relates to compounds of the formula: ##STR1## which are useful as leukotriene D.sub.4 (LTD.sub.4) inhibitors and therefore useful in the treatment of allergies and inflammatory conditions.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: May 12, 1987
    Assignee: G. D. Searle & Co.
    Inventors: Masateru Miyano, Robert L. Shone, Daniel D. Sohn
  • Patent number: 4665202
    Abstract: The invention relates to pharmaceutical preparations containing compounds of formula I ##STR1## in which X.sub.1 and X.sub.2, independently of each other, represent hydrogen, halogen, unsubstituted or substituted amino or a quaternary ammonium salt; etherified or esterified hydroxy; free, etherified, esterified or oxidized mercapto; nitro; functionally modified formyl; free or functionally modified carboxyl; acyl; an unsubstituted or substituted hydrocarbon radical, or an unsubstituted or substituted heterocyclic radical; with the proviso that at least one of the radicals X.sub.1 and X.sub.2 is bonded by a carbon atom to the ring system and with the proviso that X.sub.1 and X.sub.2 cannot be together halogen and formyl; in which Y represents oxygen, sulfur, sulfinyl or sulfonyl but must be sulfur, sulfinyl or sulfonyl, if X.sub.1 is hydrogen and X.sub.
    Type: Grant
    Filed: August 24, 1984
    Date of Patent: May 12, 1987
    Assignee: Zyma SA
    Inventors: Christian G. Rimbault, Philippe M. Narbel