Ring Nitrogen Is Shared By The Cyclos Of The Bicyclo Ring System Patents (Class 514/413)
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Patent number: 5180721Abstract: Methods and pharmaceutical formulations of alpha.sub.2 agonists and alpha.sub.3 antagonists which are useful in lowering intraocular pressure (IOP) and treatment of intraocular hypertension. Co-administration of a therapeutic amount of alpha.sub.2 agonist with a potentiating amount of alpha.sub.3 agonist is effective in lowering IOP and treatment of intraocular hypertension.Type: GrantFiled: May 30, 1991Date of Patent: January 19, 1993Assignee: Allergan, Inc.Inventor: James A. Burke
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Patent number: 5177102Abstract: There are given disclosures on a polyisoprene compound of the formula ##STR1## wherein Y is S, O, NH or ##STR2## .sub.l is an integer of 2-10, Z is a group of ##STR3## R.sup.1 and R.sup.2 are same or different and each means a hydrogen atom or an alkyl group having C.sub.1-4, m is an integer of 0 or 1, and .sub.n is an integer of 0, 1 or 2,a salt thereof, a process for the preparation of same, and use thereof.Type: GrantFiled: May 3, 1991Date of Patent: January 5, 1993Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.Inventors: Masayasu Kurono, Yasuaki Kondo, Takuji Yamaguchi, Ryoichi Unno, Hiromoto Kimura, Noboru Kuboyama, Takashi Ito, Mitsuru Oka, Akira Tashita, Kazumasa Nakano, Kiichi Sawai
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Patent number: 5132316Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which X represents R.sub.1 OOC-- in which R.sub.1 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl; R.sub.2 O-- in which R.sub.2 is C.sub.1-2 alkyl, C.sub.1 -2 alkylcarbonyl or aminocarbonyl optionally substituted by one or two methyl groups;a group ##STR2## in which Y represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one or two heteroatoms selected from oxygen, nitrogen and sulphur, any amino nitrogen optionally substituted by a C.sub.1-2 alkyl group, Y being optionally C-substituted by a methyl group; ora group ##STR3## in which A.sub.1 is oxygen or sulphur, one of A.sub.2 and A.sub.3 is CR.sub.3 and the other is nitrogen or CR.sub.4 where R.sub.3 and R.sub.4 are independently selected from hydrogen and methyl; and each of p and q independently represents an integer of 2 to 4.Type: GrantFiled: September 21, 1990Date of Patent: July 21, 1992Assignee: Beecham Group p.l.c.Inventors: Michael S. Hadley, Paul A. Wyman, Barry S. Orlek
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Patent number: 5126384Abstract: A substituted polybutadiene polymer and a composition containing the polymer which is suitable for use in a flat sheet material such as a roofing membrane is disclosed. The polymer has a superior filler capacity, excellent flame resistivity and acceptable heat aging properties, especially heat aged elongations. The composition, which includes the polymer of the present invention and from about 5 to about 160 parts by weight of a filler material per 100 parts polymer, is self-adhering without the use of an adhesive and is heat seamable to produce seams which are resistant to temperatures as high as 100.degree. C.Type: GrantFiled: June 26, 1991Date of Patent: June 30, 1992Assignees: Bridgestone/Firestone, Inc., Bridgestone CorporationInventors: James A. Davis, William L. Hergenrother, Daniel R. McGillvary, Joseph K. Valaitis
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Patent number: 5116954Abstract: Substituted six-membered benzo-fused heterocycles of the formula (I) ##STR1## in which: X=0, NH, S.fwdarw.(O).sub.n (n=0 or 2);R.sub.1 is phenyl, phenyl substituted by methoxy, hydroxy, chlorine, fluorine, diethylaminoethoxy, phenoxy, 2-methyl-4-thiazolyl, 2-amino-4-thiazolyl, phenyl, amino, nitro, terbutyl, carboxymethyl, acetamido, dimethyltriazenyl, benzoyl, hexyl, undecyl, trifluoromethyl, carbamoyl; or R.sub.1 is trifluoromethyl, pyridyl-2,pyridyl-4;R.sub.2 is H, methoxy, hydroxy; orR.sub.1 and R.sub.2 are --CH.dbd.CH--CH.dbd.CH--;R.sub.3 and R.sub.4 are methoxy, hydroxy, fluorine or form a fused benzene ring;CR.sub.5 R.sub.6 R.sub.7 is carboxymethyl, --CH.sub.2 --PO.sub.3 H,--CH.sub.2 --PO(oET).sub.2, 4-methylpiperazinyl, aminomethyl,3-4-5-trimethoxyphenylaminomethyl, acetyl, bromoacetyl, hydroxyethyl, acetoxyethyl, mercaptomethyl, acetylthiomethyl, methoxy-carbopnylthiomethyl, --CH--CONH.sub.2, ##STR2## substituted thiazolyl, subsituted furanone, imidazo(1,2-a)pyridinyl, indolizinyl, or R.sub.4 and R.Type: GrantFiled: August 2, 1989Date of Patent: May 26, 1992Assignee: Lipha, Lyonnaise Industrielle PharmaceutiqueInventors: Philippe Briet, Jean-Jacques Berthelon, Francois Collonges
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Patent number: 5110493Abstract: Stable, clear, antimicrobially effective, ophthalmic formulations include an ophthalmologically effective amount of a drug, especially a --COOH group-containing drug or a NSAID, and a preservative system formed of a quaternary ammonium preservative and a nonionic surfactant, all in an aqueous vehicle. These formulations are useful for treating diseases that are either caused by, associated with or accompanied by inflammatory processes, including, among others, glaucoma, cystoid macular edema, uveitis, diabetic retinopathy and conjunctivitis, or any trauma caused by eye surgery or eye injury.Type: GrantFiled: December 7, 1990Date of Patent: May 5, 1992Assignee: Syntex (U.S.A.) Inc.Inventors: Roger F. Cherng-Chyi, Deborah M. Lidgate
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Patent number: 5110828Abstract: Novel compounds of formula (I), a process for their preparation, and their use as pharmaceutical agents are described: ##STR1## wherein R.sub.1 represents ##STR2## in which each of p and q independently represents an integer of 2 to 4, r represents an integer of 2 to 4, s represents 1 or 2 and t represents 0 or 1;R.sub.2 is a group OR.sub.4, where R.sub.4 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, a group OCOR.sub.5 where R.sub.5 is hydrogen or R.sub.4, or a group NHR.sub.6 or NR.sub.7 R.sub.8 where R.sub.6, R.sub.7 and R.sub.8 are independently C.sub.1-2 alkyl; andR.sub.3 is hydrogen or C.sub.1-4 alkyl, subject to the proviso that when R.sub.2 is a group OCOR.sub.5 or a group NHR.sub.6, R.sub.3 is C.sub.1-4 alkyl.Type: GrantFiled: April 13, 1989Date of Patent: May 5, 1992Assignee: Beecham Group p.l.c.Inventors: Steven M. Bromidge, Michael S. Hadley, Barry S. Orlek
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Patent number: 5091397Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which one of X and Y represents hydrogen and the other represents --CH.sub.2 --Z where Z is a group ##STR2## in which Q represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one or two heteroatoms selected from oxygen, nitrogen and sulphur, or three nitrogen atoms, any amino nitrogen being optionally substituted by a C.sub.1-2 alkyl, cyclopropyl or propargyl group, and any ring carbon atom being optionally substituted by a group R.sub.1 ; or a group ##STR3## in which A.sub.1, A.sub.2 and A.sub.3 complete a 5-membered aromtic ring and A.sub.1 is oxygen or sulphur, one of A.sub.2 and A.sub.3 is CR.sub.2 and the other is nitrogen or CR.sub.3, or A.sub.2 is oxygen or sulphur, one of A.sub.1 and A.sub.3 is CR.sub.2 and the other is CR.sub.3 ; and R.sub.1, R.sub.2 and R.sub.3 are independently selected from hydrogen, halogen, CN, OR.sub.4, SR.sub.4, N(R.sub.4).sub.2, NHCOR.sub.4, NHCOOCH.sub.Type: GrantFiled: September 29, 1989Date of Patent: February 25, 1992Assignee: Beecham Group p.l.c.Inventors: Harry J. Wadsworth, Michael S. Hadley, Paul A. Wyman, Sarah M. Jenkins
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Patent number: 5077314Abstract: A method is disclosed for the containment and controlled release of and the substantial reduction of the leaching from the site of application of agricultural chemicals. In the disclosed method, the agricultural chemicals are applied to the soil dispersed in an aqueous gel-forming composition. Novel compositions of the agricultural chemicals dispersed in aqueous gel-forming compositions are also disclosed.Type: GrantFiled: May 25, 1990Date of Patent: December 31, 1991Assignee: Pfizer Inc.Inventors: Judson C. Philips, Hazen L. Hoyt, IV, Christopher A. Macri, Wesley L. Miller, John J. O'Neill
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Patent number: 5068243Abstract: Novel bicyclic tetrahydroxylated pyrrolizidines are disclosed which are inhibitors of glycosidase enzymes. A preferred inhibitor is (1S,2R,6R,7S)-1,2,6,7-tetrahydroxypyrrolizidine.Type: GrantFiled: August 7, 1990Date of Patent: November 26, 1991Assignee: Monsanto CompanyInventor: George W. J. Fleet
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Patent number: 5063231Abstract: A method of treatment of visceral pain in mammals, including humans, which method comprises the administration to the mammal in need of such treatment, an effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof:X--CO--Y--Z (I)whereinX is a group of formula (a), (b), (c), (d) or (e): ##STR1## wherein R.sub.a to R.sub.d are selected from hydrogen, halogen or hydroxy;R.sub.1 is hydrogen and R.sub.2 is hydrogen or C.sub.1-4 alkyl; orR.sub.1 and R.sub.2 together are a bond;R.sub.3 to R.sub.7 are independently hydrogen or C.sub.1-6 alkyl; andR.sub.4 together with R.sub.2 may be C.sub.2-7 polymethylene when R.sub.1 is hydrogen; either R.sub.8 is C.sub.1-6 alkoxy;R.sub.9 is hydrogen;R.sub.10 is amino or C.sub.1-7 alkanoylamino; andR.sub.11 is halo or C.sub.1-6 alkylthio; orR.sub.8 is hydrogen;R.sub.9 is halo, C.sub.1-6 alkoxy or C.sub.1-6 alkyl;R.sub.10 is hydrogen or C.sub.1-6 alkoxy; andR.sub.11 is halo, C.sub.1-6 alkoxy or C.sub.Type: GrantFiled: May 7, 1990Date of Patent: November 5, 1991Assignee: Beecham Group p.l.c.Inventors: Gareth J. Sanger, Helen E. Marr
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Patent number: 5057521Abstract: The invention relates to specific bicyclic imidazole compounds such as 5-(p-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine, or pharmaceutically acceptable non-toxic salts thereof, for the treatment of hyperaldosteronism, and to a method of treating hyperaldosteronism using such compounds, as well as to the use of said compounds for the preparation of pharmaceutical compositions for the treatment of hyperaldosteronism.Type: GrantFiled: September 26, 1989Date of Patent: October 15, 1991Assignee: Ciba-Geigy CorporationInventors: Albert Hausler, Ajay Bhatnagar
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Patent number: 5049556Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein L is NH or O;X and Y are independently selected from hydrogen or C.sub.1-4 alkyl, or together are a bond;R.sub.1 and R.sub.2 are independently selected from hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl-C.sub.1-4 alkyl, or together are C.sub.2-4 polymethylene;R.sub.3 and R.sub.4 are independently selected from hydrogen, halogen, CF.sub.3, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-7 acyl, C.sub.1-7 acylamino, C.sub.1-6 alkylsulphonylamino, N-(C.sub.1-6 alkylsulphonyl)-N-C.sub.1-4 alkylamino, C.sub.1-6 alkylsulphinyl, hydroxy, nitro or amino, aminocarbonyl, aminosulphonyl, aminosulphonylamino or N-(aminosulphonyl)-C.sub.1-4 alkylamino optionally N-substituted by one or two groups selected from C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl C.sub.1-4 alkyl, phenyl or phenyl C.sub.1-4 alkyl groups or optionally N-disubstituted by C.sub.Type: GrantFiled: August 2, 1989Date of Patent: September 17, 1991Assignee: Beecham Group p.l.c.Inventors: Francis D. King, Karen A. Joiner
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Patent number: 5032591Abstract: A pharmaceutical product comprising a potassium channel activator antihypertensive agent and a .beta.-blocker antihypertensive agent as a combined preparation for simultaneous, separate or sequential use in therapy of hypertension.Type: GrantFiled: January 4, 1989Date of Patent: July 16, 1991Assignee: Beecham Group p.l.c.Inventors: John M. Evans, Robin E. Buckingham
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Patent number: 5015655Abstract: Compounds useful in the treatment of Alzheimers's disease, senile dementia or memory disorders of the aged of the formula ##STR1## in which n represents the number 1, 2 or 3,R.sub.1 and R.sub.2, identical or different, represent hydrogen, a linear, branched or cyclic alkyl, alkenyl, or alkynyl which contain up to 6 carbon atoms, R.sub.1 and R.sub.2 optionally substituted by hydroxy, alkoxy containing up to 6 carbon atoms, aralkyl containing up to 14 carbon atoms, a COOalk.sub.1 radical in which alk.sub.1 represents alkyl containing up to 6 carbon atoms, a --CON(alk.sub.2).sub.2 radical in which alk.sub.2 represents alkyl containing up to 6 carbon the radical --C(R.sub.1).dbd.NOR.sub.2 being in position 2, 3 or 4, in all their isomer forms and their mixture, as well as their addition salts with pharmaceutically acceptable organic or mineral acids. Also therapeutic compositions containing the compounds, method of treatment and method of preparation.Type: GrantFiled: October 26, 1989Date of Patent: May 14, 1991Assignee: Roussel UCLAFInventors: Giulio Galliani, Fernando Barzaghi, Carla Bonetti, Emilio Toja
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Patent number: 5001133Abstract: The substituted benzoic acid heterocyclic amides and esters are serotonin M antagonists. Included are compounds of the formula Iq ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, Z' and R.sub.8 ' have various definitions.Type: GrantFiled: November 4, 1988Date of Patent: March 19, 1991Assignee: Sandoz Ltd.Inventors: Brian P. Richardson, Gunter Engel, Rudolf K. A. Giger, Andrea Vasella
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Patent number: 4992460Abstract: Novel bicyclic tetrahydroxylated pyrrolizidines are disclosed which are inhibitors of glycosidase enzymes. A preferred inhibitor is 1.alpha., 2.alpha., 6.alpha., 7.alpha., 7.alpha..beta.-1,2,6,7-tetrahydroxypyrrolizidine. It is synthesized from D-glycero-D-gulo-heptono-1,4-lactone.Novel Intermediate compounds prepared during this synthesis are 7-O-tert-butyldiphenylsilyl-2,3:5,6-di-O-isopropylidene-D-glycero-D-gulo-h ept ono-1,4-lactone and 1.alpha., 2.alpha., 6.alpha., 7.alpha., 7.alpha..beta.-1,2:6,7-di-O-isopropylidene-1,2,6,7-tetrahydroxypyrrolizidi ne.Type: GrantFiled: September 8, 1989Date of Patent: February 12, 1991Assignee: Monsanto CompanyInventor: George W. J. Fleet
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Patent number: 4992461Abstract: A compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein n is 0 or 1; andAr is an aromatic amide moiety, which compound exhibits prokinetic activity and is a 5-HT3 antagonist.Type: GrantFiled: September 11, 1989Date of Patent: February 12, 1991Assignee: G. D. Searle & Co.Inventors: Daniel L. Zabrowski, Daniel L. Flynn
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Patent number: 4985063Abstract: A 3-aryl-pyrrolidine-2,4-dione (e) derivative of the formula (I) ##STR1## in which X represents alkyl, halogen and alkoxy,Y represents hydrogen, alkyl, halogen, alkoxy and halogenoalkyl,Z represents alkyl, halogen and alkoxy,m represents a number from 1-4,n represents a number from 0-3, R represents hydrogen, ##STR2## or A where A represents a metal cation equivalent or represents an ammonium ion,R.sup.1 represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl and optionally substituted cycloalkyl which can be interrupted by hetero atoms, or represents optionally substituted phenyl, optionally substituted phenylalkyl, substituted hetaryl, substituted phenoxyalkyl and substituted hetaryloxyalkyl andR.sup.2 represents optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl and optionally substituted phenyl,as well as the pure enantiomeric forms of compounds of the formula (I).Type: GrantFiled: August 8, 1989Date of Patent: January 15, 1991Assignee: Bayer AktiengesellschaftInventors: Reiner Fischer, Hermann Hagemann, Andreas Krebs, Albrecht Marhold, Klaus Lurssen, Robert R. Schmidt, Hans-Joachim Santel, Benedikt Becker, Klaus Schaller, Wilhelm Stendel
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Patent number: 4968716Abstract: A composition useful for administering therapeutically active compounds to improve the body absorption and/or retention thereof comprising a composition which includes a therapeutically active compound having a molecular weight below about 5,000 and having an acidic functional group, which is normally eliminated from the body via the renal tubular secretion pathway for organic anions, for example, Vitamin C, and at least one compound selected from the class consisting of L-threonic, L-xylonic and L-lyxonic acids, and the edible salts, aldono-lactones and aldono-lactides thereof.A method for establishing and maintaining body levels of a therapeutically active compound which includes the step of administering a therapeutically effective dose of this composition.Type: GrantFiled: September 19, 1988Date of Patent: November 6, 1990Assignee: Oxycal Laboratories, Inc.Inventor: Richard G. Markham
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Patent number: 4937239Abstract: Novel 1-azabicycloalkane- and alkene-oximes (Ia) and 8-azabicyclo[3.2.1]octane- and octene-oximes (Ib) are provided, these compounds being useful as agents for treating pain or for treating the symptoms of senile cognitive decline. Also provided are pharmaceutical compositions containing the compounds and methods of treatment using the compounds in dosage form.Type: GrantFiled: February 13, 1989Date of Patent: June 26, 1990Assignee: Warner-Lambert CompanyInventors: David J. Lauffer, Walter H. Moos, Hasile Tecle
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Patent number: 4935447Abstract: A method is disclosed for the containment and controlled release of and the substantial reduction of the leaching from the site of application of agricultural chemicals. In the disclosed method, the agricultural chemicals are applied to the soil dispersed in an aqueous gel-forming composition. Novel compositions of the agricultural chemicals dispersed in aqueous gel-forming compositions are also disclosed.Type: GrantFiled: January 13, 1988Date of Patent: June 19, 1990Assignee: Pfizer Inc.Inventors: Judson C. Philips, Hazen L. Hoyt, IV, Christopher A. Macri, Wesley L. Miller, John J. O'Neill
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Patent number: 4920127Abstract: Compounds of formula (I), or a pharmaceutically acceptable salt thereof: ##STR1## wherein L is NH or O;R.sub.1 is hydrogen, fluoro or chloro;R.sub.2 and R.sub.5 are independently hydrogen or C.sub.1-6 alkyl or together are a bond; orR.sub.2 and R.sub.3 and/or R.sub.4 and R.sub.5, together are C.sub.2-7 polymethylene or --(CH.sub.2).sub.m --O--(CH.sub.2).sub.x -- where m and x. are 1 to 5 such that m+x is 2 to 6;R.sub.4 is C.sub.1-7 acyl, C.sub.1-6 alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl optionally substituted by one or two C.sub.1-6 alkyl groups, CF.sub.3, C.sub.1-6 alkyl substituted by C.sub.1-6 alkoxy, C.sub.1-6 alkylthio or by C.sub.1-6 alkoxycarbonyl, or R.sub.4 is phenyl or phenyl-C.sub.1-4 alkyl optionally substituted in the phenyl ring by one or two of halogen, C.sub.1-6 alkyl or C.sub.1-6 alkoxy;Z is a group of formula (a), (b) or (c).Type: GrantFiled: February 16, 1988Date of Patent: April 24, 1990Assignee: Beecham Group p.l.c.Inventors: Francis D. King, Karen A. Joiner
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Patent number: 4910193Abstract: Use of a mono or dicyclic carboxylic or heterocyclic carboxylic acid ester or amide of an alcohol or amine nitrogen as a ring atom in free base form or in acid addition or quaternary ammonium salt form as a 5-HT.sub.3 antagonist in the manufacture of a medicament suitable for the treatment of serotonin induced gastrointestinal disturbances.Type: GrantFiled: August 28, 1987Date of Patent: March 20, 1990Assignee: Sandoz Ltd.Inventor: Karl-Heinz Buchheit
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Patent number: 4870081Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which A represents a bond or --CH.sub.2 -- and B represents hydrogen, or A and B together with the carbon atom to which they are both attached represents a group ##STR2## R represents R.sub.1 OOC-- in which R.sub.1 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl; R.sub.2 O-- in which R.sub.2 is C.sub.1-3 alkyl, C.sub.1-2 alkylcarbonyl or aminocarbonyl optionally substituted by one or two methyl groups; or R.sub.3 CH.sub.2 - in which R.sub.3 is C.sub.1-2 alkoxy; and p represents an integer of 2 to 4, and wherein compounds of formula (I) where B is hydrogen have the stereochemical configuration in which the group R and the methylene bridge are both on the same side of the plane of the molecule which contains both bridge head atoms and the ring carbon atom bonded to the group R.Type: GrantFiled: June 26, 1987Date of Patent: September 26, 1989Assignee: Beecham Group p.l.c.Inventors: Barry S. Orlek, Michael S. Hadley, Harry J. Wadsworth, Howard E. Rosenberg
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Patent number: 4857534Abstract: This invention relates to the use of parasympathomimetic compounds, their precursors, salts and metabolites, to alter the digestive process in livestock so as to increase the efficiency of food utilization while simultaneously reducing the risk of certain disorders frequently associated with high energy diets. Specifically, the invention comprises administration to ruminants and other livestock of low level dosages of a parasympathomimetic compound to increase salivation during feeding and rumination, thereby increasing rumen digesta turnover rates and efficiency of food utilization while reducing the risk of certain digestive tract disorders such as acidosis and displaced abomasum.Type: GrantFiled: January 12, 1987Date of Patent: August 15, 1989Assignee: North Carolina State UniversityInventors: Warren J. Croom, Jr., Winston M. Hagler, Jr.
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Patent number: 4831049Abstract: A novel pyrrolizidine compound of the formula ##STR1## wherein R.sup.1 is an alkyl group of 1 to 4 carbon atoms or a phenyl group; and R.sup.2 and R.sup.3 are such that at least one of them is an alkyl group of 1 to 4 carbon atoms and the other, if not alkyl, being a hydrogen atom is produced by reacting .DELTA..sup.4(8) -dehydropyrrolizidine with a substituted malonic acid and the thus formed 2-substituted-8-pyrrolizidineacetic acid with a substituted aniline. The products are subjected to optical resolution and are potentantiarrhythmic agents.Type: GrantFiled: July 3, 1985Date of Patent: May 16, 1989Assignee: Suntory LimitedInventors: Seiji Miyano, Kunihiro Sumoto, Fumio Satoh
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Patent number: 4800207Abstract: Hexahydropyrrolizines of the formula (I): ##STR1## wherein A is a 3-7 carbon or hetero-containing ring,R.sup.1 is a substituent, andx is 0-3.Also, pharmaceutical compositions for treating pain and methods for synthesis and use as well as novel intermediates in the synthesis.Type: GrantFiled: November 2, 1987Date of Patent: January 24, 1989Assignee: McNeilab, Inc.Inventors: Richard J. Carmosin, John R. Carson
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Patent number: 4797387Abstract: Compounds of formula (I), and pharmaceutically acceptable salts thereof: ##STR1## wherein L is NH or O;X is a moiety capable of hydrogen bonding to the NH group depicted in formula (I);R.sub.1 and R.sub.2 are independently selected from hydrogen, halogen, CF.sub.3, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-7 acyl, C.sub.1-7 acylamino, C.sub.1-6 alkylsulphonylamino, N-(C.sub.1-6 alkylsulphonyl)-N-C.sub.1-4 alkylamino, C.sub.1-6 alkylsulphinyl, carboxy, C.sub.1-6 alkoxycarbonyl, hydroxy, nitro or amino, aminocarbonyl, aminosulphonyl, aminosulphonylamino or N-(aminosulphonyl)-C.sub.1-4 alkylamino optionally N-substituted by one or two groups selected from C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl C.sub.1-4 alkyl, phenyl or phenyl C.sub.1-4 alkyl groups or optionally N-disubstituted by C.sub.4-5 polymethylene; andZ is a group of formula (a), (b) or (c) ##STR2## wherein n is 2 or 3; p is 1 or 2; q is 1 to 3; r is 1 to 3; and R.sub.3 or R.sub.4 is C.sub.1-7 alkyl, C.sub.Type: GrantFiled: January 14, 1987Date of Patent: January 10, 1989Assignee: Beecham Group, p.l.c.Inventor: Francis D. King
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Patent number: 4751232Abstract: A novel pyrrolizidine derivative of the formula, ##STR1## which has potent antiarrhythmic activity and low toxicity is produced. The derivative can be synthesized: by acylating 2,6-xylidine to protect the amino group, nitrating the protected xylidine to introduce a nitro group at 3-position, reducing the nitro group to an amino group, followed by diazotizing and hydrolyzing, and then the resulted 3-hydroxy-2,6-dimethylaniline being condensed with 8-halocarbonylmethylpyrrolizidine; or by nitrating N-(2',6'-dimethyl)phenyl-8-pyrrolizidineacetamide to introduce a nitro group at 3'-position, reducing the nitro group to amino group, diazotizing the amino group and hydrolyzing the diazonium compound.Type: GrantFiled: February 21, 1985Date of Patent: June 14, 1988Assignee: Suntory LimitedInventors: Fumio Satoh, Keiyu Shima, Takafumi Ishihara
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Patent number: 4734423Abstract: This invention provides a method of providing treatment to a warm blooded animal in need of treatment of a solid cancer tumor comprising administering an effective amount of a isopropylpyrrolizine of the formula: ##STR1##Type: GrantFiled: December 3, 1985Date of Patent: March 29, 1988Assignee: The Research Foundation of State University of New YorkInventor: Wayne K. Anderson
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Patent number: 4684658Abstract: The invention provides novel pyrrole derivatives of formula: ##STR1## in which R'=H, alkyl or phenyl optionally substituted by halogen, alkyl, alkyloxy or alkylthio, Z=0 or S, p=0 or 1, andeither A is a heterocyclic ring such that it forms, with pyrrole, a 1H,3H-pyrrolo[1,2-c]thiazole, 2,3-dihydro-1H-pyrrolizine optionally substituted by OH, 5,6,7,8-tetrahydroindolizine, 1,2-dihydro-4H-pyrrolo[1,2-c]-1,3-thiazine, 2,3-dihydropyrrolo[2,1-b]thiazole, 1H,3H-pyrrolo[1,2-c]oxazole, 1,2-dihydro-4H-pyrrolo]1,2-c]-1,3-oxazine or 2,3-dihydropyrrolo[2,1-b]oxazole ring system, n=0 or 1, Het=3-pyridyl or 5-thiazolyl, and(1) either R=H, halogen, alkyl or phenyl optionally substituted by halogen, alkyloxy or alkylthio and Y=alkyl or phenyl optionally substituted by halogen, alkyl, alkyloxy or alkylthio, or Y=--NR.sub.1 R.sub.2 with:either R.sub.1 =H and R.sub.2 =unsubstituted alkyl, cycloalkyl (C.sub.3 -C.sub.6), alkenyl (C.sub.2 -C.sub.4), alkynyl (C.sub.3 -C.sub.Type: GrantFiled: December 20, 1984Date of Patent: August 4, 1987Assignee: Rhone-Poulenc SanteInventors: Jean-Louis Fabre, Daniel Farge, Claude James, Daniel Lave
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Patent number: 4678801Abstract: Novel 2-oxopyrrolidine compounds represented by the formula ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen or alkyl group, respectively, A is alkylene group or phenyl substituted alkylene group, and B is alkylene group,or a salt thereof, a process for the preparation thereof, and a pharmaceutical agent comprising the compound or salt as an effective component.Type: GrantFiled: July 10, 1986Date of Patent: July 7, 1987Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.Inventors: Masayasu Kurono, Motohide Hayashi, Tsunemasa Suzuki, Kenji Miura, Yoshihiro Kumagai, Yukiharu Matsumoto, Seiji Miyano, Kunihiro Sumoto
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Patent number: 4677098Abstract: Novel derivatives of substituted pyrrolizine diones, isomers, and pharmaceutically acceptable derivatives thereof, have therapeutic utility for reducing amnesia induced by electroconvulsive shock and for treating senility.Type: GrantFiled: November 22, 1985Date of Patent: June 30, 1987Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, Anthony J. Thomas
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Patent number: 4655815Abstract: The present invention is directed to a synergistic antimicrobial admixture comprising 2-bromo-2-bromomethylglutaronitrile and a formaldehyde donor.Type: GrantFiled: March 27, 1985Date of Patent: April 7, 1987Assignee: Calgon CorporationInventor: John A. Jakubowski
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Patent number: 4638006Abstract: A unique series of N,N-dialkylaminoalkyl-hexahydro-5-oxo-1H-pyrrolizine-3-carboxamides are disclosed. These compounds are useful as agents for the reversal of amnesia. Intermediates for preparing the compounds, pharmaceutical compositions containing them, and methods for using the pharmaceutical compositions for treating senility and for the reversal of amnesia are described.Type: GrantFiled: September 24, 1985Date of Patent: January 20, 1987Assignee: Warner Lambert CompanyInventor: Donald E. Butler
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Patent number: 4612325Abstract: Novel 5-aroyl-6-methylthio-, 6-methylsulfinyl-, or 6-methylsulfonyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids represented by the formulas ##STR1## and the pharmaceutically acceptable, non-toxic esters and salts thereof, whereinR.sub.1 is lower alkylthio, lower alkylsulfinyl, or lower alkylsulfonyl;R.sub.2 is hydrogen, hydroxy, lower alkyl, vinyl, cyclohexyl, cyclopropyl, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, nitro, amino, lower alkylcarbonylamino, lower alkylthio, lower alkylsulfonyl, or lower alkylsulfinyl;X is oxygen, sulfur, N--R.sub.3 where R.sub.3 is hydrogen or lower alkyl.This invention describes intermediates of the process and the process for the production of these compounds and their pharmaceutically acceptable non-toxic salts and pharmaceutical composition thereof. The claimed compounds are useful as anti-inflammatories and analgesics in mammals.Type: GrantFiled: June 8, 1982Date of Patent: September 16, 1986Assignee: Syntex (U.S.A) Inc.Inventors: Joseph M. Muchowski, Robert Greenhouse
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Patent number: 4608384Abstract: New thieno[2,3-b] pyrrole compounds of the formula: ##STR1## in which: R.sub.1 is hydrogen or lower alkyl,R.sub.2 is cyano, carboxy, COOM in which M is alkali alkaline-earth metal, ammonium mono-, di-, or tri-, (C.sub.1 -C.sub.5) alkylammonium optionally substituted by hydroxy, COOR in which R is lower alkyl, or ##STR2## in which R' and R" are hydrogen or lower alkyl; R.sub.3 is lower alkyl; andR.sub.4 is lower alkyl, phenyl, halophenyl, lower alkylphenyl, lower alkoxy-phenyl nitrophenyl and di-lower-alkylamino,and enatiomers thereof.These new compounds may be used as medicines especially in the treatment of acute and chronic pains.Type: GrantFiled: December 12, 1983Date of Patent: August 26, 1986Assignee: Adir, S.A.R.L.Inventors: Michel Wierzbicki, Jacques Bure
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Patent number: 4605662Abstract: A novel 1-substituted pyrrolizidine derivative having the formula: ##STR1## (wherein R.sup.1 is hydrogen or a lower alkyl group; R.sup.2 is hydrogen, a lower alkyl or lower alkoxy group, or a halogen; R.sup.3 is hydrogen, a lower alkyl, lower alkoxy or amino group, or a halogen),which can be produced by reacting 1-chlorocarbonyl (or alkoxycarbonyl)pyrrolizidine with a corresponding substituted aniline (or an alkali metal salt thereof). The pyrrolizidine derivative has antiarrhythmic activity.Type: GrantFiled: September 6, 1983Date of Patent: August 12, 1986Assignee: Suntory Ltd.Inventors: Seiji Miyano, Kunihiro Sumoto, Fumio Satoh, Hidetsura Cho
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Patent number: 4591599Abstract: A perfluorobicyclo compound of the general formula: ##STR1## wherein either or both of Ring A and Ring B may optionally be substituted with lower perfluoroalkyl group (s) and m and n each represent 3 or 4.Type: GrantFiled: November 13, 1984Date of Patent: May 27, 1986Assignee: The Green Cross CorporationInventors: Kazumasa Yokoyama, Chikara Fukaya, Yoshio Tsuda, Taizo Ono, Yoshio Arakawa, Tadakazu Suyama
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Patent number: 4564624Abstract: An 8-substituted pyrrolizidine derivative representable by the formula: ##STR1## (wherein R.sup.1 stands for hydrogen or a lower alkyl group, R.sup.2 stands for hydrogen, a lower alkyl group, a lower alkoxy group or halogen, and R.sup.3 stand for a lower alkyl group, a lower alkoxy group, amino group or halogen), which can be produced by reacting a corresponding substituted anilin with 8-halocarbonylmethyl pyrrolizidine or reacting an alkali metal salt of the corresponding substituted anilin with 8-alcoxycarbonylmethyl pyrrolizidine. The derivative is useful as an antiarrhythmic agent.Type: GrantFiled: March 10, 1983Date of Patent: January 14, 1986Assignee: Suntory Ltd.Inventors: Seiji Miyano, Kunihiro Sumoto, Minoru Morita, Fumio Sato
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Patent number: 4563469Abstract: Novel derivatives of N-[2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]amine are effective as cognition activators for reversing the effects of electroshock induced amnesia. A method of preparing the compounds, a useful intermediate in their preparation, pharmaceutical compositions, and a method of treatment are also disclosed.Type: GrantFiled: July 20, 1984Date of Patent: January 7, 1986Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, James D. Leonard
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Patent number: 4560699Abstract: Novel 5-(4-vinyl- or 4-ethynylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids represented by the formula ##STR1## and the pharmaceutically acceptable, non-toxic alkyl esters and salts thereof, wherein R is vinyl or ethynyl, and Y is hydrogen, a lower alkyl group having from 1 to 6 carbon atoms, chloro or bromo.Type: GrantFiled: January 17, 1983Date of Patent: December 24, 1985Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Stefan H. Unger
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Patent number: 4551470Abstract: Hexahydro-3,5-dioxo-1H-pyrrolizine-2-carboxylic acid, its esters, ammonium, metal, and organic amine salts are useful for the treatment of senility, for enhancing memory, and for reversing electroconvulsive shock induced amnesia in humans. Pharmaceutical compositions including these compounds, and a method of treatment employing these pharmaceutical compositions is disclosed.Type: GrantFiled: August 29, 1983Date of Patent: November 5, 1985Assignee: Warner-Lambert CompanyInventor: Donald E. Butler
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Patent number: 4548947Abstract: 1-(Substituted-aryl)-dihydro-1H-pyrrolizine-3,5-[2H,6H]-diones are effective cognition activating agents for the treatment of senility and for reversing amnesia. Pharmaceutical compositions containing these compounds and a method of treating senility or of reversing amnesia are also disclosed.Type: GrantFiled: May 7, 1984Date of Patent: October 22, 1985Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, Anthony J. Thomas
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Patent number: 4547519Abstract: Tetrahydro-3,5-dioxo-1H-pyrrolizine-7a(5H)-alkanoic acids, base addition salts, esters, and amides are useful as agents for the reversal of amnesia. Pharmaceutical compositions containing said compounds and methods for using said compositions for treating senility and reversal of amnesia are also taught.Type: GrantFiled: February 9, 1983Date of Patent: October 15, 1985Assignee: Warner-Lambert CompanyInventor: Donald E. Butler
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Patent number: 4536512Abstract: New 5-(2,3-dihydro-1H-pyrrolizin-5-oyl)-, 5-(2,3-dihydro-1H-pyrrolo[2,1-b]thiazol-5-oyl)-, 5-(2,3-dihydro-1H-pyrrolo[2,1-b]imidazol-5-oyl)-, and 5-(2,3-dihydro-1H-pyrrolo[2,1-b]oxazol-5-oyl)-derivatives of substituted 2,3-dihydro-1H-pyrrolizine-1-alkanoic or carboxylic acids have been prepared. They are found to be effective inhibitors of platelet aggregation and are analgesic/anti-inflammatory agents with low ulcerogenic side effects.Type: GrantFiled: October 8, 1982Date of Patent: August 20, 1985Assignee: Merck & Co., Inc.Inventors: Tesfaye Biftu, Bruce E. Witzel, Peter L. Barker
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Patent number: 4533671Abstract: New 5-(2,3-dihydro-1H-pyrrolizin-5-oyl)-, 5-(2,3-dihydro-1H-pyrrolo[2,1-b]thiazol-5-oyl)-, 5-(2,3-dihydro-1H-pyrrolo[2,1-b]imidazol-5-oyl)-, and 5-(2,3-dihydro-1H-pyrrolo[2,1-b]oxazol-5-oyl)-pyrrole-2-alkanoic acid derivatives have been prepared. They are found to be effective inhibitors of platelet aggregation and are analgesic and anti-inflammatory agents with low ulcerogenic side effects.Type: GrantFiled: October 8, 1982Date of Patent: August 6, 1985Assignee: Merck & Co., Inc.Inventors: Tesfaye Biftu, Bruce E. Witzel, Peter L. Barker
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Patent number: 4529597Abstract: Disclosed are substituted 1-azabicyclo [3.2.0]-hept-6-en-2-one-7-carboxylic acids (I) and their pharmaceutically acceptable salts and esters which are useful as antibiotics. ##STR1## wherein R is hydrogen, and, inter alia, unsubstituted and substituted alkyl, aryl, aralkyl; R.sup.8 is, inter alia, unsubstituted and substituted alkyl, alkenyl, aryl, and aralkyl. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.Type: GrantFiled: April 19, 1982Date of Patent: July 16, 1985Assignee: Merck & Co., Inc.Inventor: James V. Heck
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Patent number: 4517195Abstract: There are described novel pyrrolo[1,2-b][1,2,5]triazepines of the general formula ##STR1## where R is hydrogen, loweralkyl, loweralkylaminoloweralkyl or diloweralkylaminoloweralkyl; X is hydrogen, halogen (fluorine, chlorine, bromine or iodine), trifluoromethyl or nitro; and Y is hydrogen, halogen or loweralkyl. Also described are derivatives of 1-amino-2-benzoylpyrrole having the general formula ##STR2## where R, X and Y are as defined above, and R.sub.1 is hydrogen, ##STR3## Compounds I and II are useful as analgesic, anxiolytic and/or anticonvulsant agents, and many of Compounds II are useful as intermediates for synthesizing Compounds I.Type: GrantFiled: July 2, 1984Date of Patent: May 14, 1985Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Richard C. Effland, Joseph T. Klein, R. Richard L. Hamer