Oxy In Acid Moiety Patents (Class 560/42)
  • Patent number: 5514716
    Abstract: This disclosure relates to a novel class of hydroxamic and carboxylic acid based matrix metalloproteinase inhibitor derivatives. The disclosure further relates to pharmaceutical compositions containing such compounds and to the use of such compounds and compositions in the treatment of matrix metalloproteinase induced diseases.
    Type: Grant
    Filed: February 25, 1994
    Date of Patent: May 7, 1996
    Assignee: Sterling Winthrop, Inc.
    Inventors: Madhusudhan R. Gowravaram, Jeffrey Johnson, Ewell R. Cook, Robert C. Wahl, Alan M. Mathiowetz, Bruce E. Tomczuk, Ashis K. Saha
  • Patent number: 5514713
    Abstract: Disclosed are amidinophenol derivatives of the formula (I) and acid-addition salts thereof (in which R.sup.1 and R.sup.2 are alkyl, alkoxy, acyl, halogen, nitro, benzoyl, COOR.sub.4 ; A is bond, alkylene, group of the formula (II); R.sup.3 is group of the formula (III), (IV)) ##STR1## Compounds of the formula (I) have inhibitory activities on phospholipase A.sub.2 and proteases (especially trypsin), and are useful for the prevention and/or the treatment of inflammatory diseases, allergic diseases, disseminated intravascular coagulation, pancreatitis, severity in pancreatitis and multiple organ failure.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: May 7, 1996
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Hisao Nakai, Koumei Kamiyasu, Masanori Kawamura
  • Patent number: 5502078
    Abstract: Compounds of the formula (I): ##STR1## and bioprecursors and pharmaceutically acceptable salts thereof are described as .beta..sub.3 -adrenoceptor agonists having anti-obesity, hypoglycaemic and related therapeutic utilities. Processes for their preparation are described as are compositions containing them.
    Type: Grant
    Filed: May 7, 1993
    Date of Patent: March 26, 1996
    Assignee: Zeneca Limited
    Inventors: Brian R. Holloway, Ralph Howe, Balbir S. Rao
  • Patent number: 5482961
    Abstract: New soft .beta.-adrenergic blocking agents, useful in the treatment or prevention of cardiovascular disorders and in the treatment of glaucoma, have the formula ##STR1## wherein n is an integer from 0 to 10; R is C.sub.6 -C.sub.12 cycloalkyl-C.sub.p H.sub.2p --, C.sub.6 -C.sub.18 polycycloalkyl-C.sub.p H.sub.2p --, C.sub.6 -C.sub.18 polycycloalkenyl-C.sub.p H.sub.2p -- or C.sub.6 -C.sub.12 cycloalkenyl-C.sub.p H.sub.2p -- (wherein p is 0, 1, 2 or 3), or together with the adjacent ##STR2## group represents a variety of other complex ester groupings; R.sub.1 is C.sub.1 -C.sub.7 alkyl; and Ar is a divalent radical containing at least one aromatic nucleus. The corresponding pharmaceutically acceptable acid addition salts are also described.
    Type: Grant
    Filed: May 6, 1994
    Date of Patent: January 9, 1996
    Inventor: Nicholas S. Bodor
  • Patent number: 5473096
    Abstract: The present invention relates to the compounds of the formula: ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, and R.sup.8 are independently hydrogen, lower alkyl which is optionally substituted, lower alkoxy which is optionally substituted, hydroxy, acyloxy, or halogen; R.sup.9 is hydrogen, hydroxy, acyloxy, lower alkyl which is optionally substituted, lower alkoxy which is optionally substituted, or lower alkylamino which is optionally substituted; E.sup.1 is hydrogen, or an ester residue; m is an integer of from 1 to 4;or a pharmaceutically acceptable salt thereof. The compounds of the present invention exhibit phospholipase A.sub.2 inhibitory activity, and can be used in treating inflammatory conditions.
    Type: Grant
    Filed: July 21, 1993
    Date of Patent: December 5, 1995
    Assignee: Shionogi & Co., Ltd.
    Inventors: Shigeru Matsutani, Tadashi Yoshida, Ryuji Sakazaki, Yasuhiko Fujii, Kazushige Tanaka
  • Patent number: 5466834
    Abstract: A process for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted isoserine esters in which a metal alkoxide is reacted with a .beta.-lactam.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: November 14, 1995
    Assignee: Florida State University
    Inventor: Robert A. Holton
  • Patent number: 5463080
    Abstract: Compounds, useful as radiolabeling reagents, including a trihalogenated phenyl ring and having the formula ##STR1## wherein X.sub.1, X.sub.2 and X.sub.3 are halogens, one of which may be a radiohalogen, are disclosed. The invention further includes radiohalogenated proteins as well as processes for preparing such reagents and radiohalogenated proteins.
    Type: Grant
    Filed: August 27, 1992
    Date of Patent: October 31, 1995
    Assignee: Bracco International B.V.
    Inventors: Marc Ogan, Frank P. Tomasella, Jan-I Tu
  • Patent number: 5461045
    Abstract: A fused benzeneoxyacetic acid derivative of the formula: ##STR1## wherein ##STR2## is (i) ##STR3## (ii) ##STR4## (iii) ##STR5## or (iv) ##STR6## A is (i) ##STR7## or (ii) ##STR8## R.sup.1 is hydrogen or C.sub.1-4 alkyl; R.sup.2 is hydrogen, C.sub.1-6 alkyl or phenyl;R.sup.3 is(i) C.sub.1-15 alkyl,(ii) C.sub.1-8 alkyl substituted by one or two of benzene, C.sub.4-7 cycloalkane or 4-7 ring-membered monocyclic ring which contains one nitrogen atom or(iii) C.sub.10-15 condensed tricyclic ring;e is 3-5;f is 1-3;p is 0-4;q is 0-2;s is 0-3With the proviso that, ring(s) in R.sup.3 may be substituted by one to three of C.sub.1-4 alkyl, .sub.1-4 alkoxy, halogen atom, nitro or trihalomethyl. And, when D--B is the formula (iii) or (iv), --(CH2)p- or .dbd.CH--(CH2)s- is attached at the position of a or b on the ring.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: October 24, 1995
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Nobuyuki Hamanaka, Kanji Takahashi, Hidekado Tokumoto
  • Patent number: 5439937
    Abstract: This invention relates to compounds of Formula I and the stereoisomers and pharmaceutically acceptable salts thereof ##STR1## wherein R is alkyl, alkenyl, alkynyl, or cycloalkylalkyl;R.sup.1 is alkyl;R.sup.2 is hydrogen, alkyl;R.sup.6 is alkyl;n is 1 to 5;p is 0 to 6;x is 0 or 2; andR.sup.4 and R.sup.5 are independently hydrogen or alkyl or together with N form a cycloalkylamine.The compounds of Formula I are leukotriene B.sub.4 antagonists and are useful as anti-inflammatory agents and in treating disease conditions mediated by LTB.sub.4.
    Type: Grant
    Filed: March 3, 1994
    Date of Patent: August 8, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Stephen H. Docter, Stella S. Yu
  • Patent number: 5436373
    Abstract: N-benzyl-N-organo-substituted aminoalkanol is prepared by reacting benzyl chloride or substituted benzyl chloride with an organo-substituted aminoalkanol in the presence of a molar excess of the starting aminoalkanol and, optionally, water, and in the absence of a) an organic solvent for the reactants and b) alkali metal hydroxide. A portion of the excess aminoalkanol may be substituted with an alternative amine or dissolved alkali metal carbonate.
    Type: Grant
    Filed: October 26, 1994
    Date of Patent: July 25, 1995
    Assignee: Elf Atochem North America, Inc.
    Inventors: Stanley R. Sandler, Doris L. Baer
  • Patent number: 5428065
    Abstract: Pharmaceutical compounds of the formula: ##STR1## R.sup.1 to R.sup.8 are each hydrogen or C.sub.1-4 alkyl, m, n and p are each 0, 1, or 2, q is 0, 1, 2 or 3, X and Z are each C.sub.1-4 alkyl, C.sub.1-4 alkoxy, hydroxy, nitro, cyano, halo, trihalomethyl, carboxy, C.sub.1-4 alkoxy-carbonyl or phenyl, and in addition z, together with the phenyl ring to which it is attached, can be: ##STR2## Y is --O--, --S-- or --CH.sub.2 --, V is --(CH.sub.2).sub.r -- or --(CH.sub.2).sub.r S-- where r is 1 to 15, and W is hydrogen or optionally substituted phenyl; and salts thereof.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: June 27, 1995
    Assignee: Lilly Industries Limited
    Inventors: Barry P. Clark, Graham H. Timms
  • Patent number: 5405987
    Abstract: The present invention pertains to a method of preparing substituted and unsubstituted N-hydroxy-2-aminobutane diacid derivatives which can be dehydrated to 2-aminobut-2-ene dioic acid derivatives, which can be subsequently converted to pyridine and quinoline derivatives.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: April 11, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Varadaraj Elango, Donald R. Larkin, John R. Fritch, Michael P. Bodman, Werner H. Mueller, Bernard F. Gupton, John C. Saukaitis
  • Patent number: 5399178
    Abstract: Mannich condensation products prepared by the condensation of a compound having the formula: ##STR1## wherein R is hydrogen, lower alkyl having 1 through 6 carbon atoms, hydroxy or lower alkoxy having 1 through 6 atoms; R.sup.1 is polyalkyl having an average molecular weight of about from 400 to 5000 and n is 0 or a whole integer of from 1 through 10 with ammonia, alkylamine, or polyamine and an aldehyde.The condensation products and their fuel-soluble salts are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: December 17, 1993
    Date of Patent: March 21, 1995
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5399765
    Abstract: The invention relates to a method for producing albuterol by the resolution of a mixture of enantiomers of 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-hydroxybenzoate using ditoluoyltartaric acid.
    Type: Grant
    Filed: May 23, 1994
    Date of Patent: March 21, 1995
    Assignee: Sepracor, Inc.
    Inventors: Yun Gao, Charles M. Zepp
  • Patent number: 5391817
    Abstract: Certain novel biaryl compounds are effective phospholipase A.sub.2 (PLA.sub.2) inhibitors.
    Type: Grant
    Filed: December 21, 1993
    Date of Patent: February 21, 1995
    Assignee: Bristol-Myers Squibb
    Inventors: Dane Springer, Bing-Yu Luh, Katharine M. Greene, Joanne J. Bronson, Muzammil M. Mansuri
  • Patent number: 5389680
    Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.
    Type: Grant
    Filed: October 18, 1993
    Date of Patent: February 14, 1995
    Assignee: Monsanto Company
    Inventor: Peter G. Ruminski
  • Patent number: 5387594
    Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical,and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function.Use in human and veterinary medicine and in cosmetics.
    Type: Grant
    Filed: August 4, 1992
    Date of Patent: February 7, 1995
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Jean-Michel Bernardon, William R. Pilgrim
  • Patent number: 5382680
    Abstract: Allosteric hemoglobin modifier compounds having the general structural formula: ##STR1## wherein the R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 moieties may be hydrogen, halogen or alkyl groups and may be the same or different, and wherein the R.sub.7 and R.sub.8 moieties may be hydrogen or methyl groups and may be the same or different.
    Type: Grant
    Filed: June 26, 1991
    Date of Patent: January 17, 1995
    Assignee: The Center for Innovative Technology
    Inventors: Donald J. Abraham, Ahmed Mehanna, Ramnarayan Randad
  • Patent number: 5380883
    Abstract: A compound of the formula ##STR1##
    Type: Grant
    Filed: April 12, 1993
    Date of Patent: January 10, 1995
    Assignee: Roussel-Uclaf
    Inventors: Marc Benoit, Sylvain Laugraud, Jean-Louis Brayer
  • Patent number: 5373092
    Abstract: This invention relates to the production of derivatives of hydroxymethoxy mandelic acid (HMMA) and homvanillic acid (HVA), to their use in raising antibodies, and in the production of labelled compounds, and to the use of such materials in immunoassays for HMMA and HVA.
    Type: Grant
    Filed: September 15, 1993
    Date of Patent: December 13, 1994
    Assignee: Cancer Research Campaign Technology Limited
    Inventors: Gerard Gallacher, Geoffrey W. Mellor, Yee-Ping Ho
  • Patent number: 5344836
    Abstract: A fused benzenoxyacetic acid derivative of the formula (I): ##STR1## and salts thereof possess an agonistic on PGI.sub.2 receptor, so it is useful for prevention and/or treatment of thrombosis, arteriosclerosis, ischemic heart diseases, gastric ulcer and hypertention.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: September 6, 1994
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Nobuyuki Hamanaka, Kanji Takahashi, Hidekado Tokumoto
  • Patent number: 5336800
    Abstract: Oxamides useful as dye intermediates have the formula ##STR1## where R.sup.1 and R.sup.2 are independently of each other hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,X is hydroxyl, nitro or a radical of the formula --NR.sup.3 R.sup.4, where R.sup.3 is hydrogen or C.sub.1 -C.sub.4 -alkanoyl and R.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,Z is C.sub.2 -C.sub.8 -alkylene, substituted or unsubstituted phenylene or substituted or unsubstituted naphthylene, or X--Z and R.sup.1 are, together with the nitrogen atom joining them together, the radical of the formula ##STR2## where R.sup.3 is as defined above,L is a bridge member andY is vinyl or a radical of the formula --C.sub.2 H.sub.4 --A, where A is hydroxyl or a group which is detachable under alkaline reaction conditions.
    Type: Grant
    Filed: January 4, 1993
    Date of Patent: August 9, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Siegel, Manfred Patsch, Knut Kessel
  • Patent number: 5334601
    Abstract: New soft .beta.-adrenergic blocking agents, useful in the treatment or prevention of cardiovascular disorders and in the treatment of glaucoma, have the formula ##STR1## wherein n is an integer from 0 to 10; R is C.sub.6 -C.sub.12 cycloalkyl-C.sub.p H.sub.2p -, C.sub.6 -C.sub.18 polycycloalkyl-C.sub.p H.sub.2p -, C.sub.6 -C.sub.18 polycycloalkenyl-C.sub.p H.sub.2p - or C.sub.6 -C.sub.12 cycloalkenyl-C.sub.p H.sub.2p - (wherein p is 0, 1, 2 or 3), or together with the adjacent ##STR2## group represents a variety of other complex ester groupings; R.sub.1 is C.sub.1 -C.sub.7 alkyl; and Ar is a divalent radical containing at least one aromatic nucleus. The corresponding pharmaceutically acceptable acid addition salts are also described.
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: August 2, 1994
    Inventor: Nicholas S. Bodor
  • Patent number: 5302739
    Abstract: Compounds of the formula ##STR1## as intermediates for the preparation of pyrimidine or triazine herbicides.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: April 12, 1994
    Assignees: Kumiai Chemical Industry Co., Ihara Chemical Industry Co., Ltd.
    Inventors: Masatoshi Tamaru, Norihiro Kawamura, Masahiro Sato, Fumiaki Takabe, Shigehiko Tachikawa, Ryo Yoshida
  • Patent number: 5300674
    Abstract: Compounds of general formula I: ##STR1## Wherein: R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are variables.These compounds have collagenase inhibition activity and are useful in the management of disease involving collagen degradation. Its uses include rheumatoide arthritis, corneal ulceration, osteoporosis, periodontitis, gingivitis and tumour invasion.
    Type: Grant
    Filed: September 16, 1991
    Date of Patent: April 5, 1994
    Assignee: British Bio-Technology Limited
    Inventors: M. J. Crimmin, A. H. Davidson, R. P. Beckett
  • Patent number: 5298647
    Abstract: Aromatic compounds absorbing UVB and/or UVA, substituted with an amide function, selected from the group consisting of ##STR1## whose variable substituents are as defined in the specification, e.g. ##STR2## are useful as photoprotective agents or tanning accelerators.
    Type: Grant
    Filed: December 14, 1987
    Date of Patent: March 29, 1994
    Inventors: Dominique Robert, Louis Jung
  • Patent number: 5272144
    Abstract: Aryloxy- and heteroaryloxy-alkylene derivatives of amines of formula ##STR1## wherein each of A and B is a group of formula (i) to (iii): ##STR2## wherein Y is --O--, --S-- or --NR-- in which R is hydrogen or C.sub.1 -C.sub.6 alkyl; each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is independently:a) hydrogen, halogen, hydroxy, cyano or nitro;b) C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by halogen,c) C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 alkylthio;d) C.sub.1 -C.sub.6 alkyl-sulfonyl;e) a substituted amine group --NR.sub.7 R.sub.8 ;f) a --COR.sub.12 group; org) two adjacent groups of R.sub.3, R.sub.4, R.sub.5 and R.sub.6, taken together, form a C.sub.1 -C.sub.4 alkylenedioxy group;each of R.sub.1 and R.sub.2 independently is hydrogen, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 alkenyl or C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by phenyl; or R.sub.1 and R.sub.
    Type: Grant
    Filed: June 13, 1991
    Date of Patent: December 21, 1993
    Assignee: Farmitalia Carlo Erba s.r.l.
    Inventors: Piero Melloni, Philippe Dostert, Arturo D. Torre, Alberto Bonsignori
  • Patent number: 5266720
    Type: Grant
    Filed: July 8, 1991
    Date of Patent: November 30, 1993
    Assignee: Cancer Research Campaign Technology Limited
    Inventors: Gerard Gallacher, Geoffrey W. Mellor, Yee-Ping Ho
  • Patent number: 5252317
    Abstract: Disclosed are amplifier molecules: various organic compounds having branched structures terminating with amine groups to which pharmacologically active groups can be chemically attached. A number of MRI contrast-enhancing agents were synthesized, each comprising plural active groups, such as stable nitroxides and complexes of trivalent metal cations. Such syntheses were successfully performed using a number of amplifiers having different branched structures, demonstrating the general utility of the pertinent chemistry in the synthesis of amplifiers having any of a wide variety of pharmacologically active groups. Amplifiers were also synthesized having linkers terminating with chemically reactive groups such as isothiocyanates, which render the amplifier bifunctional: attachable to polymers, biomacromolecules, or other biocompatible entity possessing multiple reactive sites such as terminal amines.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: October 12, 1993
    Assignee: The State of Oregon Acting by and through the State Board of Higher Education on Behalf of the University of Oregon
    Inventor: John F. W. Keana
  • Patent number: 5250735
    Abstract: Novel 2-(N-substituted-aminoalkyl)-5-(E)-alkylidene cyclopentanones, 2-(N-substituted-aminoalkyl)-5-(E)-arylalkylidene cyclopentanones, and derivatives thereof having the formula ##STR1## wherein x is methylene or ethylene; R.sub.1 is dimethylamino, diethylamino, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, anilino or substituted anilino; R.sub.2 is hydrogen, straight or branched alkyl of 1 to 9 carbon atoms, aryl or arylalkyl; R.sub.3 is hydrogen, straight or branched alkyl of 1 to 9 carbon atoms, aryl or arylalkyl; and R.sub.4 is hydrogen, methyl, ethyl, allyl, benzyl, substituted benzyl, cyclopentyl, substituted cyclopentyl, cyclopenten-1-yl, or substituted cyclopenten-1-yl; and wherein aryl is phenyl or phenyl substituted with one or more methoxyl, hydroxyl, methylenedioxy, chloro, bromo, fluoro, ethoxycarbonylmethoxy, benzoxy, alkyl group, or their combination, possess anti-inflammatory, analgesic and anticancer properties.
    Type: Grant
    Filed: April 3, 1992
    Date of Patent: October 5, 1993
    Assignee: University of Pittsburgh
    Inventors: Lan K. Wong, Hai-Tao Chen, Zhi-Zhong Ji
  • Patent number: 5237099
    Abstract: The present invention relates to methods for controlling insect populations and for protecting living plants from insect attack by applying to said plants or to the soil in which they are growing an insecticidally-effective amount of a substituted benzoic acid 1 or 2-alkyl or 2-cycloalkylhydrazide.Novel substituted benzoic acid 1 and 2-alkyl and 2-cycloalkylhydrazides effective as insecticides or intermediates for the preparation of insecticidal diacylhydrazides also are presented.
    Type: Grant
    Filed: June 8, 1990
    Date of Patent: August 17, 1993
    Assignee: American Cyanamid Company
    Inventors: Roger W. Addor, David G. Kuhn, Donald P. Wright, Jr.
  • Patent number: 5234946
    Abstract: The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7,X and Y are linking groups,R.sup.2 is H or lower alkyl,R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl,R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms,R.sup.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: August 10, 1993
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Takezawa, Masahiro Hayashi, Yoshikazu Iwasawa, Masaaki Hosoi, Yoshiaki Iida, Yoshimi Tsuchiya, Masahiro Horie, Toshio Kamei
  • Patent number: 5232948
    Abstract: Monocyclic aryl compounds having selective LTB.sub.4 antagonists properties and comprising an amido substituent, a substituent group having a terminal carboxylic acid or derivative thereof and a lipophilic substituent, therapeutic compositions and methods of treatment of disorders which result from LTB.sub.4 activity using the monocyclic aryl compounds are disclosed.
    Type: Grant
    Filed: September 10, 1990
    Date of Patent: August 3, 1993
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Fu-Chih Huang, Wan K. Chan, Charles A. Sutherland, Robert A. Galemmo, Jr., Michael N. Chang
  • Patent number: 5210276
    Abstract: Phenylethanolamino- and phenylethanolaminomethyltetralines of formula (I) ##STR1## wherein X represents a hydrogen atom, a halogen atom, a (C.sub.1 -C.sub.4)alkyl group or a trifluoromethyl group,A represents a bond between the --COOR group and the tetraline ring, a (C.sub.1 -C.sub.4)alkylene or a (C.sub.2 -C.sub.4)alkenylene group,R is hydrogen or a (C.sub.1 -C.sub.4)alkyl group, andn is 0 or 1and their salts, are typically prepared by reaction of an epoxide of formula (IIa) ##STR2## with a tetraline derivative of formula (III) ##STR3## wherein A and n are as defined above and R' is a (C.sub.1 -C.sub.4)alkyl group, optionally followed by basic hydrolysis to obtain the compounds (I) wherein R is hydrogen.The new compounds show very interesting properties as antidepressant and intestinal spasmolytic agents.The new intermediates of formula (III) are also claimed.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: May 11, 1993
    Assignee: Elf Sanofi
    Inventors: Domenico Badone, Umberto Guzzi, Roberto Cecchi
  • Patent number: 5202347
    Abstract: New soft .beta.-adrenergic blocking agents, useful in the treatment or prevention of cardiovascular disorders and in the treatment of glaucoma, have the formula ##STR1## wherein n is an integer from 0 to 10; R is C.sub.6 -C.sub.12 cycloalkyl-C.sub.p H.sub.2p --, C.sub.6 -C.sub.18 polycycloalkyl-C.sub.p H.sub.2p --, C.sub.6 -C.sub.18 polycycloalkenyl-C.sub.p H.sub.2p -- or C.sub.6 -C.sub.12 cycloalkenyl-C.sub.p H.sub.2p -- (wherein p is 0, 1, 2 or 3), or together with the adjacent ##STR2## group represents a variety of other complex ester groupings; R.sub.1 is C.sub.1 -C.sub.7 alkyl; and Ar is a divalent radical containing at least one aromatic nucleus. The corresponding pharmaceutically acceptable acid addition salts are also described.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: April 13, 1993
    Inventor: Nicholas S. Bodor
  • Patent number: 5202483
    Abstract: Ethylenically unsaturated compounds of the general formula I ##STR1## where R.sub.1 is alkyl of 1 to 4 carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, phenyl or phenyl in which some or all of the hydrogen atoms have been replaced by radicals R.sup.4, not more than two substituents R.sup.4 being identical, or R.sup.1 together with R.sup.2 or together with R.sup.6 forms a --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 -- bridge,R.sup.4 is alkyl of 1 to 24 carbon atoms, --OH, --O--R.sup.7, --S--R.sup.7, ##STR2## R.sup.2 or R.sup.6, independently of one another, both are hydrogen, or one of the radicals R.sup.4, or, where R.sup.1 is aryl,R.sup.2 or R.sup.6 is a direct bond to R.sup.1 in the ortho-position with respect to the carbonyl group, andR.sup.3 and R.sup.5 are each hydrogen, one of the radicals R.sup.4 or a group the general formula II ##STR3## where R.sup.7 and R.sup.8 are each alkyl of 1 to 4 carbon atoms,R.sup.9 is cycloalkyl of 5 or 6 carbon atoms,R.sup.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: April 13, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Rehmer, Kaspar Bott
  • Patent number: 5162569
    Abstract: A class of substituted phenylacetonitrilealkylaminoalkyl-ortho-substituted aryl compounds having immunosuppressive properties is described. Compounds of this class would be useful in reducing recipient rejection of transplanted organs and for treatment of autoimmune or inflammatory diseases. Compounds of particular interest are of the formula ##STR1## wherein m is one or two; wherein n is a number selected from one to five, inclusive; wherein R.sup.1 is selected from hydrido, alkyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkenyl and alkynyl; wherein R.sup.6 is selected from loweralkyl; wherein each of R.sup.8, R.sup.9, R.sup.10 and R.sup.12 through R.sup.16 is independently selected from hydrido, hydroxy, alkyl, hydroxyalkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonylalkenyl, alkylaminocarbonyl and alkoxyalkyl; with the proviso that at least one of R.sup.12 and R.sup.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: November 10, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Chi-Dean Liang, John P. McKearn, John M. Farah, Jr., Richard A. Mueller
  • Patent number: 5145874
    Abstract: Provided are cyclic hydrocarbons of Formula I ##STR1## with an aminoalkyl sidechain that are useful for treating phospholipase A2 mediated conditions, diabetes, and obesity.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: September 8, 1992
    Assignee: The Upjohn Company
    Inventors: Roy A. Johnson, Gordon L. Bundy, Gilbert A. Youngdale, Douglas R. Morton, Donald P. Wallach, deceased, by Vera M. Wallach, legal representative
  • Patent number: 5144073
    Abstract: Disclosed is a process for synthesis of a dipeptide such as N-acetyl-L-.alpha.-aspartyl-L-phenylalanine methyl ester wherein one amino acid serves as a chiral template which allows for synthesis of a second amino acid residue to form said dipeptide. The process involves several novel steps such as a nucleophile addition step. In addition, several novel intermediates are described.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: September 1, 1992
    Inventor: John C. Hubbs
  • Patent number: 5135737
    Abstract: Disclosed are amplifier molecules: various organic compounds having branched structures terminating with amine groups to which pharmacologically active groups can be chemically attached. A number of MRI contrast-enhancing agents were synthesized, each comprising plural active groups, such as stable nitroxides and complexes of trivalent metal cations. Such syntheses were successfully performed using a number of amplifiers having different branched structures, demonstrating the general utility of the pertinent chemistry in the synthesis of amplifiers having any of a wide variety of pharmacologically active groups. Amplifiers were also synthesized having linkers terminating with chemically reactive groups such as isothiocyanates, which render the amplifier bifunctional: attachable to polymers, biomacromolecules, or other biocompatible entity possessing multiple reactive sites such as terminal amines.
    Type: Grant
    Filed: September 5, 1989
    Date of Patent: August 4, 1992
    Assignee: The State of Oregon Acting by and through the State Board of Higher Education on behalf of the University of Oregon
    Inventor: John F. W. Keana
  • Patent number: 5135926
    Abstract: New soft .beta.-adrenergic blocking agents, useful in the treatment or prevention of cardiovascular disorders and in the treatment of glaucoma, have the formula ##STR1## wherein n is an integer from 0 to 10; R is C.sub.6 -C.sub.12 cycloalkyl-C.sub.p H.sub.2p -, C.sub.6 -C.sub.18 polycycloalkyl-C.sub.p H.sub.2p -, C.sub.6 -C.sub.18 polycycloalkenyl-C.sub.p H.sub.2p - or C.sub.6 -C.sub.12 cycloalkenyl-C.sub.p H.sub.2p - (wherein p is 0, 1, 2 or 3), or together with the adjacent ##STR2## group represents a variety of other complex ester groupings; R.sub.1 is C.sub.1 -C.sub.7 alkyl; and Ar is a divalent radical containing at least one aromatic nucleus. The corresponding pharmaceutically acceptable acid addition salts are also described.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: August 4, 1992
    Inventor: Nicholas S. Bodor
  • Patent number: 5130454
    Abstract: Polytetrahydrofuran derivatives of the general formula ##STR1## where n is from 2 to 70, X is the bridge member --NH-- or --O-- and R.sup.1 and R.sup.4 are each hydrogen or various radicals.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
  • Patent number: 5130339
    Abstract: New phenylethanolaminomethyltetralins of formula (I) ##STR1## wherein E represents hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, phenyl, nitro, halogen, or trifluoromethyl,L represents hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkyoxy, phenyl, nitro, or halogen, orE and L taken together represent a group --CH.dbd.CH--CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --, andG represents hydrogen, chloro, hydroxy or an --OG' group wherein G' represents a (C.sub.1 -C.sub.4 (alkyl group either unsubstituted or substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, carboxy, or (C.sub.3 -C.sub.7)cycloalkyl; a (C.sub.3 -C.sub.7)cycloalkyl group; or a (C.sub.2 -C.sub.4)alkanoyl group; and salts thereof, are described which showed to be active as intestinal motility modulating agents and intraocular hypertension lowering agents.
    Type: Grant
    Filed: December 28, 1990
    Date of Patent: July 14, 1992
    Assignee: Sanofi
    Inventors: Roberto Cecchi, Umberto Guzzi
  • Patent number: 5124478
    Abstract: The invention relates to new compounds of the formula ##STR1## in which R.sup.1 denotes (C.sub.1 -C.sub.8)-alkyl, R.sup.2 denotes an amino acid residue which is protected with a urethane protective group which can be eliminated with weak acid or base, or denotes an amino protective group which can be eliminated with weak acid or base, R.sup.3 denotes hydrogen or (C.sub.1 -C.sub.4)-alkyl, and Y.sup.1 -Y.sup.9 denote identical or different radicals hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or --O--(CH.sub.2).sub.n --COOH (with n=1 to 6), with one of these radicals being --O--(CH.sub.2).sub.n --COOH, or Y.sup.1, Y.sup.2 and Y.sup.5 -Y.sup.9 denote identical or different radicals hydrogen, (C.sub.1 -C.sub.4)-alkyl or (C.sub.1 -C.sub.4)-alkoxy, Y.sup.3 denotes hydrogen or (C.sub.1 -C.sub.8)-alkoxy and Y.sup.4 denotes --(CH.sub.2).sub.n --COOH or --NH--CO--(CH.sub.2).sub.n --COOH (with n=1 to 6).
    Type: Grant
    Filed: December 20, 1988
    Date of Patent: June 23, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Breipohl, Jochen Knolle, Werner Stuber
  • Patent number: 5122435
    Abstract: Amido-containing azulene-aquaric acid dyes of the formula ##STR1## where L is C.sub.1 -C.sub.12 -alkylene which may be substituted by phenyl,R.sup.1 and R.sup.2 are each independently of the other hydrogen, substituted or unsubstituted C.sub.1 -C.sub.20 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, substituted or unsubstituted phenyl, 2,2,6,6-tetramethylpiperidin-4-yl or cyclohexylaminocarbonyl andR.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently of the others hydrogen or substituted or unsubstituted C.sub.1 -C.sub.12 -alkyl,with the proviso that when R.sup.6 is hydrogen the positions of the substituents CH.sub.2 --L--CO--NR.sup.1 R.sup.2 and R.sup.5 on either or both azulene rings may also be interchanged with each other within an azulene ring are used in an optical recording medium.
    Type: Grant
    Filed: October 22, 1990
    Date of Patent: June 16, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Schmitt, Bernhard Albert, Sibylle Brosius, Klaus D. Schomann, Harald Kuppelmaier
  • Patent number: 5105021
    Abstract: A higher yield of the difluorohalomethoxybenzene produced by the reaction of a metal phenolate with dibromodifluoromethane or bromochlorodifluoromethane can be obtained by conducting the addition of a metal alcoholate or a metal hydride as a reaction initiator to a solution or a suspension of an aprotic polar solvent containing the metal phenolate and dibromodifluoromethane or bromochlorodifluoromethane.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: April 14, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Hideyuki Akieda, Naoki Sato, Koichi Morinaga, Yoshinori Ide, Ryuichi Mita, Mitsumasa Umemoto
  • Patent number: 5102911
    Abstract: HMG-CoA reductase inhibitors of formulae (I) and (II) are disclosed.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: April 7, 1992
    Assignee: Merck & Co, Inc.
    Inventors: Ta J. Lee, Wilbur J. Holtz
  • Patent number: 5084592
    Abstract: Azulenesquaric acid dyes of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each have specified meanings are prepared from azulene derivatives of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each have specified meanings as intermediates, and used in an optical recording medium.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: January 28, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Schrott, Peter Neumann, Sibylle Brosius, Helmut Barzynski, Klaus D. Schomann, Harald Kuppelmaier
  • Patent number: 5064564
    Abstract: The present invention discloses an optically active compound represented by the following general formula (I): ##STR1## wherein R.sup.1 represents an alkyl, alkoxyl, or alkoxyalkanoyloxy group which has 1 to 18 carbon atoms and may be substituted with fluorine, chlorine, or cyano group; R.sup.2 represents an alkyl group having 1 to 18 carbon atoms; ##STR2## m is 0 or 1; Y represents a single bond, --CH.sub.2 O--, or --COO--; Z represents a single bond or --COO--; and C* and C** each independently represents an asymmetric carbon atom of the (R) and (S) configuration, an intermediate therefor being represented by the following general formula (II): ##STR3## wherein R.sup.2 represents an alkyl group having 1 to 18 carbon atoms, n is 0 or 1, and C* and C** each independently represents an asymmetric carbon atom of the (R) or (S) configuration, a process for producing the intermediate, and a liquid-crystal compound using the optically active compound.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: November 12, 1991
    Assignees: Dainippon Ink and Chemicals, Inc., Sagami Chemical Research Center
    Inventors: Sadao Takehara, Takeshi Kuriyama, Toru Fujisawa, Kayoko Nakamura, Tamejiro Hiyama, Kusumoto, Tetsuo, Akiko Nakayama
  • Patent number: 5047228
    Abstract: Nonionic compounds of the formula ##STR1## wherein X is --CONR.sub.1 R.sub.2, --COOR.sub.3, --CH.sub.2 NHR.sub.7 or --CH.sub.2 OH; Y is --1R.sub.1 R.sub.2 or --OR.sub.3 ; and Z is --NR.sub.1 R.sub.2, --NHR.sub.7 or --OR.sub.3 ; and wherein R.sub.1 R.sub.2 and R.sub.3 in X, Y or Z, and R.sub.7 in X and Z, are identical or different, R.sub.1 and R.sub.2, and each is hydrogen, C.sub.1-6 -alkyl or C.sub.2-8 - alkyl substituted by 1-5 OH groups and/or by a C.sub.1-3 -alkoxy group; R.sub.3 is C.sub.1-4 -alkyl or C.sub.2-4 -alkyl substituted by 1-2 OH groups and/or by a C.sub.1-3 -alkoxy group; and R.sub.7 is an acyl group of a C.sub.2-5 OH group and/or by a C.sub.1-3 -alkoxy group are highly advantageous X-ray contrast agents.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: September 10, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Heinz Gries, Heinrich Pfeiffer, Ulrich Speck, Wolfgang Mutzel