Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Bicyclo Ring System Patents (Class 549/405)
  • Patent number: 6239284
    Abstract: The invention concerns aromatic tetralcyclic compounds of the retinoid type of general formula (I). The invention also concerns the method for preparing them and the pharmaceutical compositions containing at least one of said compounds.
    Type: Grant
    Filed: July 15, 1999
    Date of Patent: May 29, 2001
    Assignee: Centre Europeen de Bioprospective-CEB
    Inventors: Bertrand Leblond, Abdallah Deyine, Alain-René Schoofs, Pierre Germain, Bernard Pourrias
  • Patent number: 6239171
    Abstract: The present invention relates to novel tocotrienols and tocotrienol-like compounds displaying biological activity. The tocotrienols and tocotrienol-like compounds of this invention may be conveniently obtained from biological sources or by chemical synthesis and may be used in pharmaceutical compositions, foodstuffs and dietary supplements. This invention also relates to the use of tocotrienols, tocotrienol-like compounds, and mixtures thereof, as hypocholesterolemic, antithrombotic, antioxidizing, antiathermogenic, antiinflammatory and immunoregulatory agents, or as agents useful to decrease lipoprotein (a) concentration in the blood or to increase feed conversion efficiency.
    Type: Grant
    Filed: October 28, 1998
    Date of Patent: May 29, 2001
    Assignee: Lipogenics, Inc.
    Inventors: Ronald H. Lane, Asaf A. Qureshi, Winston A. Salser
  • Patent number: 6221900
    Abstract: The invention provides BTK inhibitors, methods for their identification and use, and pharmaceutical compositions comprising BTK inhibitors.
    Type: Grant
    Filed: October 4, 1999
    Date of Patent: April 24, 2001
    Assignee: Hughes Institute
    Inventors: Fatih M. Uckun, Yaguo Zheng, Sutapa Ghosh
  • 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: 6204290
    Abstract: The present invention relates to novel tocotrienols and tocotrienol-like compounds displaying biological activity. The tocotrienols and tocotrienol-like compounds of this invention may be conveniently obtained from biological sources or by chemical synthesis and may be used in pharmaceutical compositions, foodstuffs and dietary supplements. This invention also relates to the use of tocotrienols, tocotrienol-like compounds, and mixtures thereof, as hypocholesterolemic, antithrombotic, antioxidizing, antiatherogenic, antiinflammatory and immunoregulatory agents, or as agents useful to decrease lipoprotein (a) concentration in the blood or to increase feed conversion efficiency.
    Type: Grant
    Filed: October 28, 1998
    Date of Patent: March 20, 2001
    Assignee: Lipogenics, Inc.
    Inventors: Ronald H. Lane, Asaf A. Qureshi, Winston A. Salser
  • Patent number: 6197978
    Abstract: A process for the manufacture of the racemic compound of the formula (I), its R-enantiomer (formula R-(I)) and its S-enantiomer (formula S-(I)), and pharmaceutically acceptable salts and/or solvates thereof, as well as new intermediates obtained and used in the process.
    Type: Grant
    Filed: May 6, 1998
    Date of Patent: March 6, 2001
    Assignee: Astra Aktiebolag
    Inventors: Sverker Hanson, Lars Johansson, Daniel D. Sohn
  • Patent number: 6194450
    Abstract: Novel pharmaceutically/cosmetically-active polyaromatic heterocyclic compounds have the structural formula (I): in which Z is a divalent radical selected from among —O—, —S— or —Nr′— and Ar is either a radical having the following structural formula (II): or a radical having the following structural formula (III): and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: July 23, 1998
    Date of Patent: February 27, 2001
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Bruno Charpentier, Philippe Diaz, Philippe Nedoncelle
  • Patent number: 6143770
    Abstract: The present invention relates to novel tocotrienols and tocotrienol-like compounds displaying biological activity. The tocotrienols and tocotrienol-like compounds of this invention may be conveniently obtained from biological sources or by chemical synthesis and may be used in pharmaceutical compositions, foodstuffs and dietary supplements. This invention also relates to the use of tocotrienols, tocotrienol-like compounds, and mixtures thereof, as hypocholesterolemic, antithrombotic, antioxidizing, antiatherogenic, antiinflammatory and immunoregulatory agents, or as agents useful to decrease lipoprotein (a) concentration in the blood or to increase feed conversion efficiency.
    Type: Grant
    Filed: October 28, 1998
    Date of Patent: November 7, 2000
    Assignee: Lipogenics, Inc.
    Inventors: Ronald H. Lane, Asaf A. Qureshi, Winston A. Salser
  • Patent number: 6136986
    Abstract: The invention relates to a process for preparing substituted chroman derivatives of the general formula VII, ##STR1## where X is the group --CN, --COOR.sup.3, --CHO, --CH.sub.2 OR.sup.7 or --CH(OR.sup.8).sub.2,R.sup.2 is a C.sub.1 -C.sub.23 -alkyl, C.sub.2 -C.sub.23 -alkenyl, C.sub.6 -C.sub.18 -aryl or C.sub.7 -C.sub.18 -aralkyl radical,R.sup.3 is hydrogen or an optionally substituted C.sub.1 -C.sub.4 -alkyl radical,R.sup.4, R.sup.5, R.sup.6 are, independently of one another, hydrogen or a C.sub.1 -C.sub.4 -alkyl radical,R.sup.7 is hydrogen or a C.sub.1 -C.sub.4 -alkyl radical,R.sup.8 is a C.sub.1 -C.sub.4 -alkyl radical, or the two radicals are a C.sub.2 -C.sub.6 -alkylene radical which links the two oxygen atoms to form a cyclic acetal and is optionally branched or may carry one or two carboxyl groups, cyclohexyl or phenyl radicals,and to the novel intermediates of the process.
    Type: Grant
    Filed: December 13, 1999
    Date of Patent: October 24, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Sturmer, Kai-Uwe Baldenius
  • Patent number: 6110960
    Abstract: A compound having structure (1) wherein (a) X is selected from the group consisting of O, S, SO, or SO.sub.2 ; (b) each Y is independently hydrogen or straight, branched or cyclic alkanyl having from 1 to about 4 carbon atoms, or the two Y's are bonded to form an alkanyl ring having from 3 to about 7 carbon atoms; (c) Z is branched or cyclic alkyl having from 3 to about 10 atoms other than hydrogen; (d) W is O or S; and (e) R is straight, branched or cyclic alkyl or aryl, saturated or mono- or di-unsaturated with double or triple bonds, R having from 1 to about 15 atoms other than hydrogen; pharmaceutical compositions comprising such compounds, and methods of treating inflammation or pain using such compounds.
    Type: Grant
    Filed: December 7, 1998
    Date of Patent: August 29, 2000
    Assignee: The Procter & Gamble Company
    Inventors: John Michael Janusz, Carl Randolph Johnson, Chandrawansha Bandara Weerasinghe Senanayake
  • Patent number: 6093836
    Abstract: The present invention relates to a novel 1,3-diphenylpropane derivative having an inhibitory activity against tyrosinase represented by the following formula (I): ##STR1## in which - - represents double or single bond,R.sub.1 represents hydrogen or C.sub.1 -C.sub.10 alkyl,R.sub.2 represents C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxyalkyl, orR.sub.1 and R.sub.2 together represent a 5 to 6 membered heterocycle which can be substituted by C.sub.1 -C.sub.5 alkyl and which contains oxygen as the hetero atom,R.sub.3 represents hydrogen or C.sub.1 -C.sub.7 alkyl,R.sub.4 represents hydrogen, hydroxy, or oxo, andR.sub.5 and R.sub.6 mindependently of one another represent hydrogen or C.sub.1 -C.sub.5 alkyl.
    Type: Grant
    Filed: November 6, 1998
    Date of Patent: July 25, 2000
    Assignee: LG Chemical Ltd.
    Inventors: Young Ho Rhee, Kyung Ae Kim, Hyun Ho Lee, Jong Kwon Choi, Sang Hwa Lee
  • Patent number: 6090810
    Abstract: Aryl-substituted and aryl and (3-oxo-1-propenly)-substituted benzopyran, benzothiopyran, 1,2-dihydroquinoline, and 5,6-dihydronaphthalene derivatives have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action of RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists. For example, the retinoid negative hormone called AGN 193109 effectively increased the effectiveness of other retinoids and steroid hormones in in vitro transactivation assays. Additionally, transactivation assays can be used to identify compounds having negative hormone activity.
    Type: Grant
    Filed: December 30, 1998
    Date of Patent: July 18, 2000
    Assignee: Allergan Sales, Inc.
    Inventors: Elliott S. Klein, Alan T. Johnson, Andrew M. Standeven, Richard L. Beard, Samuel J. Gillett, Tien T. Duong, Sunil Nagpal, Vidyasagar Vuligonda, Min Teng, Roshantha A. Chandraratna
  • Patent number: 6034256
    Abstract: A class of benzopyran, derivatives is described for use in treating cyclooxygenase-2 mediated disorders. Compounds of particular interest are defined by Formula I' ##STR1## wherein X, A.sup.1, A.sup.2, A.sup.3, A.sup.4, R, R", R.sup.1 and R.sup.2 are as described in the specification.
    Type: Grant
    Filed: April 17, 1998
    Date of Patent: March 7, 2000
    Assignee: G.D. Searle & Co.
    Inventors: Jeffery S Carter, Mark G Obukowicz, Balekudru Devadas, John J Talley, David L Brown, Matthew J Graneto, Stephen R Bertenshaw, Donald J Rogier, Jr., Srinivasan R Nagarajan, Cathleen E Hanau, Susan J Hartmann, Cindy L Ludwig, Suzanne Metz
  • Patent number: 5952345
    Abstract: Aryl-substituted and aryl and (3-oxo-1-propenly)-substituted benzopyran, benzothiopyran, 1,2-dihydroquinoline, and 5,6-dihydronaphthalene derivatives have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action of RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists. For example, the retinoid negative hormone called AGN 193109 effectively increased the effectiveness of other retinoids and steroid hormones in in vitro transactivation assays. Additionally, transactivation assays can be used to identify compounds having negative hormone activity.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: September 14, 1999
    Assignee: Allergan Sales, Inc.
    Inventors: Elliot S. Klein, Alan T. Johnson, Andrew M. Standeven, Richard L. Beard, Samuel J. Gillett, Tien T. Duong, Sunil Nagpal, Vidyasagar Vuligonda, Min Teng, Roshantha A. Chandraratna
  • Patent number: 5889045
    Abstract: A compound of formula (I): ##STR1## in which: R.sub.1 represents alkyl,R.sub.2, R.sub.4 and R.sub.5, which may be identical or different, represent hydrogen or alkyl,R.sub.3 represents any one of the groups as defined in the description,X represents carbonyl or methylene,Y represents hydrogen or alkyl or aryl,A represents single bond or alkylphenyl,R.sub.6 represents any one of the groups as defined in the description, its isomers as well as its addition salts with a pharmaceutically acceptable acid or base,and medicinal productes containing the same are useful in the treatment of diabetes and complications of diabetic disease.
    Type: Grant
    Filed: November 25, 1997
    Date of Patent: March 30, 1999
    Assignee: Adir et Compagnie
    Inventors: Timothee Muller, Claudie Moulin, Muriel Duflos, Sylvie Robert-Piessard, Guillaume Le Baut, Alain Tonnerre, Daniel-Henri Caignard, Dominique Manechez, Pierre Renard
  • Patent number: 5877207
    Abstract: Aryl-substituted and aryl and (3-oxo-1-propenly)-substituted benzopyran, benzothiopyran, 1,2-dihydroquinoline, and 5,6-dihydronaphthalene derivatives have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action of RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists. For example, the retinoid negative hormone called AGN 193109 effectively increased the effectiveness of other retinoids and steroid hormones in in vitro transactivation assays. Additionally, transactivation assays can be used to identify compounds having negative hormone activity.
    Type: Grant
    Filed: June 24, 1997
    Date of Patent: March 2, 1999
    Assignee: Allergan Sales, Inc.
    Inventors: Elliott S. Klein, Alan T. Johnson, Andrew M. Standeven, Richard L. Beard, Samuel J. Gillett, Tien T. Duong, Sunil Nagpal, Vidyasagar Vuligonda, Min Teng, Roshantha A. Chandraratna
  • Patent number: 5856490
    Abstract: Compounds of the formula ##STR1## where the symbols have the meaning defined in the specification have retinoid-like biological activity.
    Type: Grant
    Filed: September 4, 1997
    Date of Patent: January 5, 1999
    Assignee: Allergan
    Inventors: Min Teng, Tien T. Duong, Roshantha A. Chandraratna
  • Patent number: 5849798
    Abstract: Novel pharmaceutically/cosmetically-active polyaromatic heterocyclic compounds have the structural formula (I): ##STR1## in which Z is a divalent radical selected from among --O--, --S-- or --Nr'-- and Ar is either a radical having the following structural formula (II): ##STR2## or a radical having the following structural formula (III): ##STR3## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: December 15, 1998
    Assignee: Centre International De Recherches Dermatologiques Galderma
    Inventors: Bruno Charpentier, Philippe Diaz, Philippe Nedoncelle
  • Patent number: 5821264
    Abstract: The present invention relates to novel tocotrienols and tocotrienol-like compounds displaying biological activity. The tocotrienols and tocotrienol-like compounds of this invention may be conveniently obtained from biological sources or by chemical synthesis and may be used in pharmaceutical compositions, foodstuffs and dietary supplements. This invention also relates to the use of tocotrienols, tocotrienol-like compounds, and mixtures thereof, as hypocholesterolemic, antithrombotic, antioxidizing, antiatherogenic, antiinflammatory and immunoregulatory agents, or as agents useful to decrease lipoprotein (a) concentration in the blood or to increase feed conversion efficiency.
    Type: Grant
    Filed: September 24, 1996
    Date of Patent: October 13, 1998
    Assignee: LipoGenics, Inc.
    Inventors: Ronald H. Lane, Asaf A. Qureshi, Winston A. Salser
  • Patent number: 5817766
    Abstract: Novel benzpyran derivatives and the use of these derivatives in producing novel anti-cannabinoid antibodies are disclosed. Also disclosed is the use of these antibodies as reagents in improved immunoassays for tetrahydrocannabinol metabolites in biological fluid samples.
    Type: Grant
    Filed: April 5, 1995
    Date of Patent: October 6, 1998
    Assignee: Roche Diagnostic Systems, Inc.
    Inventors: Raymond Albert Hui, Steven Mark Rosen, Salvatore Joseph Salmone
  • Patent number: 5811083
    Abstract: Novel tocopherol derivatives useful for regulating skin aging and other skin disorders, as well as compositions containing the derivatives and methods for their use are described. The tocopherol derivative is tocopherol-cysteamine. Such types of skin atrophy to be treated the thinning of the epidermis and/or general degradation of the dermis often characterized by hyperplasia and structural disorganization. Such skin maladies include but are not limited to dry skin, severe dry skin, terosis, dandruff, keratoses, psoriasis, eczema, pruritus, age spots, lentigines, melasmas, wrinkles, blemished skin, hyperpigmented skin, hyperkeratotic skin, inflammatory dermatoses and age-related skin changes.
    Type: Grant
    Filed: March 26, 1996
    Date of Patent: September 22, 1998
    Assignee: Estee Lauder, Inc.
    Inventors: Edward Pelle, Daniel H. Maes
  • Patent number: 5780651
    Abstract: This invention relates to an improved process for the preparation of 5-methylchroman-6-carboxylic acid, a useful intermediate in the preparation of chroman-containing diacylhydrazines which are useful as insecticides, by reacting a Hagemann's ester with a propargyl derivative in the presence of a base and a solvent to produce a propargyl ether, rearranging the propargyl ether by application of heat with a suitable catalyst being present, with or without a solvent, to produce a cyclic ether type compound and isomerizing the cyclic ether type compound with a catalyst in a suitable solvent to produce a chroman ester. The propargyl ethers and the cyclic ether type compounds produced by the process of the present invention are new.
    Type: Grant
    Filed: July 9, 1997
    Date of Patent: July 14, 1998
    Assignee: Rohm and Haas Company
    Inventor: Robert Eugene Hormann
  • Patent number: 5780652
    Abstract: This invention relates to an improved process for the preparation of 5-methylchroman-6-carboxylic acid, a useful intermediate in the preparation of chroman-containing diacylhydrazines which are useful as insecticides, by reacting a Hagemann's ester with a propargyl derivative in the presence of a base and a solvent to produce a propargyl ether, rearranging the propargyl ether by application of heat with a suitable catalyst being present, with or without a solvent, to produce a cyclic ether type compound and isomerizing the cyclic ether type compound with a catalyst in a suitable solvent to produce a chroman ester. The propargyl ethers and the cyclic ether type compounds produced by the process of the present invention are new.
    Type: Grant
    Filed: July 9, 1997
    Date of Patent: July 14, 1998
    Assignee: Rohm and Haas Company
    Inventor: Robert Eugene Hormann
  • Patent number: 5767290
    Abstract: The present invention relates to a process for preparing protected amines or amino acids. The invention furthermore relates to the use of tocopheryl radicals or radicals derived therefrom as protective groups for amines and amino acids, and to compounds obtained in this process as intermediates and to processes for preparing dipeptides and oligopeptides.
    Type: Grant
    Filed: February 26, 1997
    Date of Patent: June 16, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Rosenau, Wolf-Dieter Habicher, Chen-Loung Chen
  • Patent number: 5753695
    Abstract: The invention relates to a compound of formula (I) ##STR1## wherein X is a pharmacologically acceptable anion,R.sub.1 and R.sub.2 are independently of each other hydrogen, or an --OY group in which Y is hydrogen, an .alpha.-aminoacyl, or a C.sub.1-5 aminoalkyl residue,R.sub.3, R.sub.4 and R.sub.7 are independently of each other hydrogen, or a C.sub.1-5 alkyl residueR.sub.5 is hydrogen, and .alpha.-aminoacyl, or a C.sub.1-5 alkyl residue, andR.sub.6 is hydrogen, OH.sup.-, or a C.sub.1-5 alkyl residue,and pharmaceutically acceptable salts and esters thereof; and to condensation processes for preparing them.
    Type: Grant
    Filed: May 19, 1994
    Date of Patent: May 19, 1998
    Assignee: Biogal Gyogyszergyar RT
    Inventors: Gyorgy Sulyok, Janos Balint, Ildiko Borbely, Jolan Kiss, Ferenc D. Toth
  • Patent number: 5719180
    Abstract: Described herein is a chroman derivative represented by the following formula: ##STR1## wherein X represents H, --CH.sub.2 OH, --CHO, --COOH, --COOCH.sub.3, --CH.dbd.NOH, --CONH.sub.2, --COCH.sub.3, --CH(OH)CH.sub.3, Br, or CN; Y represents a hydroxyl group which may optionally be protected; R represents an alkyl group, alkenyl group, or aralkyl group; provided that, where X is hydrogen atom, R is an alkyl group, alkenyl group, or aralkyl group each having 16 or more carbon atoms; and a vitamin E-like active medicament comprising said derivative as an active ingredient.
    Type: Grant
    Filed: August 12, 1996
    Date of Patent: February 17, 1998
    Assignee: Koichi Shudo
    Inventors: Koichi Shudo, Masashi Akaike
  • Patent number: 5719145
    Abstract: The invention relates to a substituted amidine derivative which has an excellent platelet aggregation inhibiting action on the basis of fibrinogen antagonism and is particularly excellent in effectiveness on oral administration, and the platelet aggregation inhibitor containing the substituted amidine derivative of the invention as an effective ingredient is effective for prevention and treatment of thrombosis, and restenosis or reocclusion after percutaneous transluminal coronary angioplasty or percutaneous transluminal coronary recanalization.
    Type: Grant
    Filed: August 19, 1996
    Date of Patent: February 17, 1998
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Hiroyuki Yamashita, Kunio Okumura, Toshiyuki Shimazaki, Akihito Kanematsu, Yoji Aoki, Yuki Nakajima, Kouhei Yazawa, Kenji Kibayashi
  • Patent number: 5698716
    Abstract: This invention relates to an improved process for the preparation of 5-methylchroman-6-carboxylic acid, a useful intermediate in the preparation of chroman-containing diacylhydrazines which are useful as insecticides, by reacting a Hagemann's ester with a propargyl derivative in the presence of a base and a solvent to produce a propargyl ether, rearranging the propargyl ether by application of heat with a suitable catalyst being present, with or without a solvent, to produce a cyclic ether type compound and isomerizing the cyclic ether type compound with a catalyst in a suitable solvent to produce a chroman ester. The propargyl ethers and the cyclic ether type compounds produced by the process of the present invention are new.
    Type: Grant
    Filed: November 5, 1996
    Date of Patent: December 16, 1997
    Assignee: Rohm and Haas Company
    Inventor: Robert Eugene Hormann
  • Patent number: 5686471
    Abstract: A compound having the structure: ##STR1## wherein (a) n is from about 1 to about 3;(b) X is selected from the group consisiting of O, S, SO, or SO.sub.2 ;(c) Y is independently hydrogen or straight, branched or cyclic alkyl or aralkyl having from 1 to about 3 carbon atoms; or the Y's are bonded together to form an alkanyl ring having from 3 to about 7 atoms;(d) Z is hydrogen or straight, branched or cyclic alkyl having from 3 to about 10 atoms other than hydrogen;(e) R.sub.1 and R.sub.2 are each independently hydrogen or straight, branched or cyclic alkyl, unsubstituted or substituted, carboxyl, carboxamido, alkoxycarbonyl or alkylcarbonyl; and(f) Het is a heteroaryl group comprising one or more rings containing from about 5 to about 8 atoms in the rings and wherein at least one ring has at least one heteroatom selected from O, N, or S,pharmaceutical compositions comprising such compounds, and methods of treating inflammation or pain using such compounds.
    Type: Grant
    Filed: February 1, 1996
    Date of Patent: November 11, 1997
    Assignee: The Procter & Gamble Company
    Inventors: Zhuoliang Chen, John Michael Janusz
  • Patent number: 5675024
    Abstract: Compounds of the formula ##STR1## where the symbols have the meaning defined in the specification have retinoid-like biological activity.
    Type: Grant
    Filed: November 22, 1995
    Date of Patent: October 7, 1997
    Assignee: Allergan
    Inventors: Min Teng, Tien T. Duong, Roshantha A. Chandraratna
  • 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: 5658796
    Abstract: Described herein is a process for resolving a racemic (C>3) alkyl (R, S) chroman-2-carboxylate compound useful as intermediates in the synthesis of optically pure pharmaceutical compounds is disclosed. The process utilizes a microbial enzyme derived from Serratia marcescens to catalyze the enantioselective hydrolysis of the (C>3) alkyl (S)-chroman-2-carboxylate enantiomer of the racemic mixture to its corresponding carboxylic acid at a faster rate than the R-enantiomer. An enantiomerically pure S-configured carboxylic acid is thereby formed which can undergo acidic esterification to provide an optically pure (C>3) alkyl (S)-chroman-2-carboxylate intermediate for subsequent pharmaceutical synthesis. The nonhydrolyzed (C>3) alkyl (R)-chroman-2-carboxylate enantiomer can also be isolated to provide an optically pure pharmaceutical precursor.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: August 19, 1997
    Assignee: SepraChem, Inc.
    Inventors: Richard F. Rossi, Jr., Charles M. Zepp, Donald L. Heefner
  • Patent number: 5646308
    Abstract: Benzopyran derivatives represented by formula (I): ##STR1## wherein X represents .dbd.O, .dbd.S, .dbd.N--Z, etc. (Z represents a lower alkyl group, etc.); Y represents a substituted amino group, an alkoxy group, an alkylthio group, etc., and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 each represents a hydrogen atom, a lower alkyl group, etc, are disclosed. The benzopyran derivative exhibit K.sup.+ channel opening activities and are widely applicable as antiasthmatics, antiepileptics, and the like.
    Type: Grant
    Filed: July 18, 1994
    Date of Patent: July 8, 1997
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Hiroshi Koga, Hiroyuki Nabata
  • Patent number: 5646310
    Abstract: Described herein are benzopyran derivatives represented by the formula: ##STR1## wherein R, X and Y represent any of the following combinations:______________________________________ R X Y ______________________________________ C.sub.2 F.sub.5 O H C.sub.2 F.sub.5 S H CF.sub.3 S F C.sub.2 F.sub.5 S F C.sub.3 F.sub.7 S F ______________________________________and pharmaceutically acceptable salts thereof. These compounds have an excellent potassium channel activity and are also excellent from the aspect of safety.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 8, 1997
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Hiroshi Koga, Haruhiko Sato, Takenori Ishizawa
  • Patent number: 5605896
    Abstract: This invention provides bicyclic heterocyclic derivatives and their pharmaceutically acceptable salts useful for the treatment of hypertension, urethral and lower urinary tract contractions, and other disorders. The compounds are also useful for binding .alpha..sub.1 -adrenergic and 5HT.sub.1A serotonergic receptors, in vitro or in vivo.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: February 25, 1997
    Assignee: Recordati S.A., Chemical and Pharmaceutical Company
    Inventors: Amedeo Leonardi, Gianni Motta, Carlo Riva, Rodolfo Testa
  • Patent number: 5596100
    Abstract: A method is provided for the regioselective, palladium catalyzed carbo- or heteroannulation of internal alkynes by aryl iodides containing o-substituted side chains to yield aromatic carbocyclic and heterocyclic ring systems.
    Type: Grant
    Filed: April 4, 1995
    Date of Patent: January 21, 1997
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Richard C. Larock
  • Patent number: 5530028
    Abstract: Insecticidal compounds having the formula N-(2-R.sup.a -3-R.sup.b -4-R.sup.h -benzoyl)-N'-(2-R.sup.c -3-R.sup.d -4-R.sup.e -5-R.sup.f -benzoyl)-N'-R.sup.g -hydrazine wherein R.sup.a is a halo or lower alkyl; R.sup. b is lower alkoxy, optionally substituted with halo (preferably fluoro); R.sup.c is selected from hydrogen, halo, lower alkyl, lower alkoxy, lower alkoxy lower alkyl, and nitro; R.sup.d, R.sup.e and R.sup.f are each independently selected from hydrogen, bromo, chloro, fluoro, lower alkyl, lower alkoxy, and lower alkoxy lower alkyl; R.sub.g is a (C.sub.4 -C.sub.6)alkyl; R.sup.h is hydrogen, lower alkoxy, lower alkyl, or when taken together with R.sup.b is methylenedioxy (--OCH.sub.2 O--), 1,2-ethylenedioxy (--OCH.sub.2 CH.sub.2 O--), 1,2-ethyleneoxy (--CH.sub.2 CH.sub.2 O--) or 1,3-propyleneoxy (--CH.sub.2 CH.sub.2 CH.sub.2 O--) wherein an oxo atom is located at the R.sup.b position; and the substituents R.sup.c and R.sup.d, or R.sup.d and R.sup.e, or R.sup.e and R.sup.
    Type: Grant
    Filed: September 29, 1993
    Date of Patent: June 25, 1996
    Assignee: Rohm and Haas Company
    Inventors: Zev Lidert, Dat P. Le, Robert E. Hormann, Thomas R. Opie
  • Patent number: 5516784
    Abstract: Compounds of formula ##STR1## wherein Ar, W, Z, Q, R.sub.1, U, and T are as set forth herein, are described. These compounds are active as agents against retroviruses and in particular against HIV.
    Type: Grant
    Filed: February 10, 1994
    Date of Patent: May 14, 1996
    Assignee: Schering Corporation
    Inventors: Frank Bennett, Ashit Ganguly, Viyyoor Girijavallabhan, Naginbhai Patel
  • Patent number: 5516917
    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 represents alkyl from 1 to 5 carbon atoms, aryl or aryl substituted with halogen or alkyl from 1 to 5 carbon atoms;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: June 8, 1994
    Date of Patent: May 14, 1996
    Assignee: G. D. Searle & Co.
    Inventors: Steven W. Djuric, Stella S. Yu
  • Patent number: 5516918
    Abstract: There is provided a method for safening herbicides in crop plants by using substituted benzopyran or tetrahydronaphthalene compounds of formula I ##STR1## Further provided are compounds of formula II and compositions comprising a herbicide and an antidotally effective amount of a substituted benzopyran or tetrahydronaphthalene compound of formula I.
    Type: Grant
    Filed: January 31, 1995
    Date of Patent: May 14, 1996
    Assignee: American Cyanamid Company
    Inventors: Gail E. Cary, Nina R. Quinn
  • Patent number: 5508275
    Abstract: Lipid-selective antioxidants of the formula I(A).sub.a (L)(X).sub.a, (I),in whichA=an antioxidative component,L=a bridging member,X=a lipophilic componenta and a'=independently of one another the numbers 1 or 2.The compounds are used for the protection of lipid-containing substances against oxidation and in pharmaceuticals for the prophylaxis and treatment of diseases in which bioradicals are involved, in particular of coronary, circulatory and vascular diseases.
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: April 16, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus-Ulrich Weithmann, Gunther Wess, Dirk Seiffge
  • Patent number: 5495026
    Abstract: A phenol, a formaldehyde and an unsaturated compound having carbon-carbon double bond are reacted in the presence of a secondary amine and an acid at a temperature of 100.degree. to 250.degree. C., to give a chroman.
    Type: Grant
    Filed: September 13, 1994
    Date of Patent: February 27, 1996
    Assignee: Kuraray Company Ltd.
    Inventors: Eriko Fukumoto, Masahiro Torihara, Yoshin Tamai
  • Patent number: 5482942
    Abstract: This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: January 9, 1996
    Assignee: American Home Products Corporation
    Inventors: Richard M. Soll, Paul J. Dollings
  • Patent number: 5480645
    Abstract: Hydroxyamines N-acyl derivatives with benzochroman or 2,3-dihydrobenzofuran carboxy acids and relative pharmaceutical composition for the therapeutic treatment of those CNS, vascular, cardiovascular, dermatologic and ophthalmic pathologies wherein it is important to associate an inflammatory modulation effect to an antioxidant activity.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: January 2, 1996
    Assignee: LifeGroup S.p.A.
    Inventors: Francesco Della Valle, Silvana Lorenzi, Gabriele Marcolongo
  • Patent number: 5474994
    Abstract: This invention provides bicyclic heterocyclic derivatives and their pharmaceutically acceptable salts useful for the treatment of hypertension, urethral and lower urinary tract contractions, and other disorders. The compounds are also useful for binding .alpha..sub.1 -adrenergic and 5HT.sub.1A serotonergic receptors, in vitro or in vivo.
    Type: Grant
    Filed: May 26, 1993
    Date of Patent: December 12, 1995
    Assignee: Recordati S.A., Chemical and Pharmaceutical Company
    Inventors: Amedeo Leonardi, Gianni Motta, Carlo Riva, Rodolfo Testa
  • Patent number: 5468878
    Abstract: Cyclohexanedione derivatives of the general formula (I), ##STR1## wherein: R is a C.sub.1 -C.sub.4 alkyl group,each of R.sup.1 to R.sup.6 is independently hydrogen or a C.sub.1 -C.sub.4 alkyl group,X.sup.1 is a C.sub.1 -C.sub.4 alkyl group,X.sup.2 is hydrogen or a C.sub.1 -C.sub.4 alkyl group, andn is an integer of 0 to 2.or salta thereof exhibit high selectivity for corn, wheat and barley, can control gramineous weeds and broad-leaved weeds at a low dosage, and can be desirably used as an active ingredient of a herbicide.
    Type: Grant
    Filed: February 2, 1995
    Date of Patent: November 21, 1995
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Ichiro Nasuno, Mitsuru Shibata, Masashi Sakamoto, Kazuyoshi Koike
  • Patent number: 5418232
    Abstract: A compound of formula (I) possesses excellent potassium channel opening activity and is effective on various diseases arising from contractions of blood vessels, bronchial smooth muscles, etc., for example, ischemic heart diseases exemplified by angina pectoris, asthma, pollakisuria, sequela of subarachnoid hemorrhage, peripheral arterioinfarct, and so on. The compound has potent and long-lasting antihypertensive activity, with the onset of the action being slow, excellent activity in increasing renal blood flow, and high safety, and is therefore particularly useful as an antihypertensive. ##STR1## The substituents are as defined in the specification.
    Type: Grant
    Filed: May 12, 1993
    Date of Patent: May 23, 1995
    Assignee: Daiichi Pharmaceutical Co., Ltd.
    Inventors: Tetsuya Mimura, Hideo Kubo
  • Patent number: 5412117
    Abstract: Benzopyran derivatives represented by formula (I): ##STR1## wherein X represents =O, =S, =N-Z (Z represents a lower alkyl group, etc.), or =CHNO.sub.2 ; Y represents a substituted amino group, an alkoxy group, an alkylthio group, etc., and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 each represent a hydrogen atom, a lower alkyl group, etc., are disclosed. The benzopyran derivatives exhibit K.sup.+ channel activating activities and are widely applicable as antiasthmatics, antiepileptics, and the like.
    Type: Grant
    Filed: January 26, 1993
    Date of Patent: May 2, 1995
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Hiroshi Koga, Hiroyuki Nabata
  • Patent number: 5403953
    Abstract: Compound of formula (I): ##STR1## in which: R.sub.1 represents halogen, or hydroxy, alkyl, alkoxy, cyano, amino, mercapto, alkylthio or phenoxy,R.sub.2 and R'.sub.2 represent two hydrogen when the ring is unsaturated, or alternatively identical or different, represent hydrogen or halogen, or hydroxy, alkyl, alkoxy, cyano, amino or oxo when the ring is saturated,R.sub.3 represents any one of the following groups: ##STR2## in which: m represents 1, 2 or 3,X represents oxygen or sulfur or N-R, R.sub.5 or R.sub.6, which are identical or different, represent hydrogen or alkyl or trifluoromethyl or form (C.sub.3 -C.sub.6) cycloalkyl,n represents 0, 1 or 2,R.sub.7 represents hydroxy, alkoxy, amino, or --O--CH.sub.2 --CO--NRR',R.sub.4 represents hydrogen or halogen or alkyl, alkoxy or trihaloalkyl.
    Type: Grant
    Filed: November 23, 1993
    Date of Patent: April 4, 1995
    Assignee: Adir et Compagnie
    Inventors: Guillaume de Nanteuil, Michel Vincent, Christine Lila, Jacqueline Bonnet, Armel Fradin