The -oh Or -om Is Bonded To An Acyclic Carbon, Which Carbon Is Bonded Directly To Two Rings Patents (Class 546/241)
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Patent number: 5654433Abstract: The present invention is related to a novel process for preparing certain piperidine derivatives which are useful as antihistamines, antiallergy agents and bronchodilators.Type: GrantFiled: May 3, 1995Date of Patent: August 5, 1997Assignee: Merrell Pharmaceuticals Inc.Inventors: Chi-Hsin Richard King, Michele A. Kaminski
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Patent number: 5652370Abstract: The present invention is related to a novel process for preparing certain piperidine derivatives which are useful as antihistamines, antiallergy agents and bronchodilators.Type: GrantFiled: May 2, 1995Date of Patent: July 29, 1997Assignee: Merrell Pharmaceuticals Inc.Inventors: Chi-Hsin Richard King, Michele A. Kaminski
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Patent number: 5650516Abstract: The present invention is related to a novel process for preparing certain piperidine derivatives which are useful as antihistamines, antiallergy agents and bronchodilators.Type: GrantFiled: May 3, 1995Date of Patent: July 22, 1997Assignee: Merrell Pharmaceuticals Inc.Inventors: Chi-Hsin Richard King, Michele A. Kaminski
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Patent number: 5644061Abstract: The present invention is related to a novel process for preparing certain piperidine derivatives which are useful as antihistamines, antiallergy agents and bronchodilators.Type: GrantFiled: May 1, 1995Date of Patent: July 1, 1997Assignee: Merrell Pharmaceuticals Inc.Inventors: Chi-Hsin Richard King, Michele A. Kaminski
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Patent number: 5631375Abstract: The present invention is related to a novel process for preparing certain piperidine derivatives which are useful as antihistamines, antiallergy agents and bronchodilators, these piperidine derivatives can be described by the following formulas: ##STR1## wherein R.sub.1 represents hydrogen or hydroxy;R.sub.2 represents hydrogen; orR.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ;n is an integer of from 1 to 5;R.sub.3 is --CH.sub.2 OH, --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched;each of A is hydrogen or hydroxy; andpharmaceutically acceptable salts, hydrates and individual optical isomers thereof.Type: GrantFiled: January 6, 1995Date of Patent: May 20, 1997Assignee: Merrell Pharmaceuticals, Inc.Inventors: Chi-Hsin R. King, Michele A. Kaminski, Teng-Man Chen
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Patent number: 5618940Abstract: The present invention is related to a novel process for preparing certain piperidine derivatives which are useful as antihistamines, antiallergy agents and bronchodilators.Type: GrantFiled: May 2, 1995Date of Patent: April 8, 1997Assignee: Merrell Pharmaceuticals Inc.Inventors: Chi-Hsin R. King, Michele A. Kaminski
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Patent number: 5589486Abstract: The invention relates to novel N-hydroxy-substituted 1,2,3,6-tetrahydropyridine and piperidine derivatives of the formula ##STR1## wherein A, B, D, E, G, I and R are as defined in the specification, m is 0, 1 or 2, with the proviso that:m is 0 or 2, or both G and I are hydrogen, when A is benzyl or halogen-monosubstituted benzyl group; andm is 1, when A is 2-picolyl, as well as their pharmaceutically acceptable acid addition salts. The compounds of formula (I) are useful for enhancing the tolerance of mammals (including man) against hypoxic and/or ischaemic states as well as for treating the degenerative and functional disturbances arising from hypoxic and/or ischaemic results.Type: GrantFiled: January 17, 1995Date of Patent: December 31, 1996Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Kalman Harsanyi, Tibor Gizur, Eva Agai-Csongor, Anna Kallai-Sohonyai, Marta Kapolnas-Pap, Eva Csizer, Bela Heged us, Laszlo Szporny, Bela Kiss, Egon Karpati, Eva Palosi, Zsolt Szombathelyi, Adam Sarkadi, Aniko Gere, Mihaly Bodo, Katalin Csomor, Judit Laszy, Zsolt Szentirmai, Erzsebet Lapis, Sandor Szabo, Peter Bod, Attila Csehi
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Patent number: 5561144Abstract: The present invention is directed to a new 5HT.sub.2 antagonist, (+)-.alpha.-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidine methanol, and its use in the treatment of a number of disease states.Type: GrantFiled: January 13, 1995Date of Patent: October 1, 1996Assignee: Merrell Pharmaceuticals Inc.Inventors: Albert A. Carr, John M. Kane, David A. Hay, Christopher J. Schmidt
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Patent number: 5541331Abstract: Disclosed are preferred processes for producing .alpha.-2-pyridyl.alpha.-aryl carbinol or .alpha.-4-pyridyl .alpha.-aryl carbinol compounds.Type: GrantFiled: June 15, 1995Date of Patent: July 30, 1996Assignee: Reilly Industries, Inc.Inventors: Ramiah Murugan, Gerald L. Goe, Eric F. V. Scriven
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Patent number: 5457207Abstract: The compounds are vesamicol (hydroxylated phencyclidine (PCP) isomer trans-2-(4-phenyl-piperidino)cyclohexanol) derivatives with anticholinergic properties termed herein "spirovesamicols" which are spirofused piperidines. The compounds bind to the vesamicol receptor, a site on the cholinergic synaptic vesicle, which is associated with the vesicular transporter of acetylcholine.Type: GrantFiled: October 5, 1993Date of Patent: October 10, 1995Assignee: Regents of the University of MinnesotaInventors: Simon M. N. Efange, Stanley M. Parsons
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Patent number: 5432175Abstract: Pyridine and pyridine N-oxide derivatives of diaryl methyl piperidines or piperazines and pharmaceutically acceptable salts thereof are disclosed, which possess anti-allergic and anti-inflammatory activity. Pharmaceutical compositions containing and methods of using the compounds are also described.Type: GrantFiled: April 1, 1993Date of Patent: July 11, 1995Assignee: Schering CorporationInventors: John J. Piwinski, Jesse Wong, Michael J. Green, Vera Seidl, Richard Friary
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Patent number: 5347006Abstract: The invention relates to a method for preparing HMP terfenadine comprising the steps of reacting terfenadone free-base with sodium borohydride to yield mixed polymorph terfenadine and crystallizing said mixed polymorph terfenadine from a seeded ester or ketone solvent system to yield substantially pure HMP terfenadine.Type: GrantFiled: December 31, 1992Date of Patent: September 13, 1994Inventors: Augusto Lavacchielli, Mirco Fornaroli, Giovanni Colli
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Patent number: 5317024Abstract: Novel unsaturated ether derivatives of alkyl piperidine and pyrrolidine compounds, pharmaceutical compositions containing them, methods of preparation and methods of using these compounds as antipsychotic agents are disclosed.Type: GrantFiled: August 3, 1993Date of Patent: May 31, 1994Assignee: DuPont Merck Pharmaceutical Co.Inventors: Gary A. Cain, Thomas E. Christos, Sang W. Tam
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Patent number: 5296606Abstract: Hydroximic acid derivatives of the formula ##STR1## These compounds are useful for treating diabetes angiopathy.Type: GrantFiled: July 1, 1992Date of Patent: March 22, 1994Assignee: Biorex Kutato-Fejleszto KFTInventors: Peter L. Nagy, Bela Balazs, Maria Boross, Jeno Szilbereky, Gizella Zsila, Lajos braham, Gyorgy Blasko, Bela Gachalyi, Attila Almasi, Gabor Nemet
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Patent number: 5286866Abstract: The present invention pertains to a new class of compounds which can be characterized as 1,4-disubstituted piperidinyl compounds useful as antiarrhythmics, analgesics, and serotonin 5HT.sub.2 antagonists.Type: GrantFiled: February 14, 1992Date of Patent: February 15, 1994Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Albert A. Carr, John E. Koerner, Richard C. Dage, Tung Li
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Patent number: 5252586Abstract: Novel unsaturated ether derivatives of alkyl piperidine and pyrrolidine compounds, pharmaceutical compositions containing them, methods of preparation and methods of using these compounds as antipsychotic agents are disclosed.Type: GrantFiled: September 28, 1990Date of Patent: October 12, 1993Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Gary A. Cain, Thomas E. Christos, Sang W. Tam
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Patent number: 5250517Abstract: Compounds which are amino acid derivatives and have the formula ##STR1## in which R.sup.1 is hydrogen or methyl, R.sup.2 is ethyl, propyl or imidazol-4-yl, R.sup.3 is isobutyl, cyclohexylmethyl or benzyl, and A is defined as herein are useful as renin inhibitors.Type: GrantFiled: May 4, 1992Date of Patent: October 5, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Quirico Branca, Albrecht Edenhofer, Eva-Maria Gutknecht, Werner Neidhart, Henri Ramuz, Wolfgang Wostl
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Patent number: 5247092Abstract: A process for preparing the high-melting polymorph of terfenadine, characterized by dissolving terfenadine in a water-miscible polar solvent by heating to a temperature of between 40.degree. and 100.degree. C. The solution is then percolated into a sufficient quantity of water, kept stirring at ambient temperature, to cause substantial precipitation of the high-melting terfenadine polymorph.Type: GrantFiled: February 12, 1991Date of Patent: September 21, 1993Assignee: Erregierre Industria Chimica S.p.A.Inventor: Egidio Molinari
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Patent number: 5169096Abstract: This invention relates to a new class of compounds having important biochemical and pharmacological properties. More particularly, this invention relates to N-aralkyl piperidinemethanol derivatives which are potent and selective inhibitors of the binding of serotonin at the 5HT.sub.2 receptor site, and to the processes for their preparation and use.Type: GrantFiled: January 3, 1991Date of Patent: December 8, 1992Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Albert A. Carr, Norbert L. Wiech
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Patent number: 5147879Abstract: Hydroximic acid derivatives of the formula ##STR1## These compounds are useful for treating diabetes angiopathy.Type: GrantFiled: June 28, 1990Date of Patent: September 15, 1992Assignee: Biorex Kutato-Fejleszto KftInventors: Peter L. Nagy, Bela Balazs, Maria Boross, Jeno Szilbereky, Gizella Zsila, Lajos braham, Gyorgy Blasko, Bela Gachalyi, Attila Almasi, Gabor Nemet
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Patent number: 5134149Abstract: The present invention is directed to a new 5HT.sub.2 antagonist, (+)-.alpha.-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidine methanol, and its use in the treatment of a number of disease states.Type: GrantFiled: July 26, 1991Date of Patent: July 28, 1992Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Albert A. Carr, John M. Kane, David A. Hay, Christopher J. Schmidt
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Patent number: 5064838Abstract: The present invention relates to 1,4-disubstituted-piperidinyl compounds that have utility as analgesics and as muscle relaxants.Type: GrantFiled: December 7, 1988Date of Patent: November 12, 1991Assignee: Merrell Dow PharmaceuticalsInventors: Albert A. Carr, Francis P. Miller, Thaddeus R. Nieduzak, Stephen M. Sorensen
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Patent number: 5039802Abstract: The chiral catalyst of general structure 1, or its enantiomer ##STR1## is prepared by treating the corresponding N-carboxy anhydride of structure 2 ##STR2## with an aryl metal, especially a phenyl metal such as an aryl magnesium halide, aryl lithium, aryl zinc or aryl cesium, to form a 1,1-diaryl-methanol of structure 3 ##STR3## followed by treatment with a compound of structure, 4 ##STR4## The catalyst, wherein R is aromatic, is novel and in some cases superior to the catalyst wherein R is alkyl or aralkyl in directing the chirality of borane-dimethyl sulfide reductions of ketones to secondary alcohols.Type: GrantFiled: April 18, 1990Date of Patent: August 13, 1991Assignee: Merck & Co., Inc.Inventors: Thomas J. Blacklock, Todd K. Jones, David J. Mathre, Lyndon C. Xavier
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Patent number: 5021428Abstract: The invention relates to a new class of compounds having important biochemical and pharmacological properties. More particularly, this invention relates to N-aralkyl piperidinemethanol derivatives which are potent and selective inhibitors of the binding of serotonin at the 5HT.sub.2 receptor site, and to the processes for their preparation and use.Type: GrantFiled: November 17, 1989Date of Patent: June 4, 1991Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Albert A. Carr, Norbert L. Wiech
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Patent number: 4882326Abstract: Piperidine compounds of the formula: ##STR1## or isomers thereof as well as pharmaceutically acceptable salts and/or hydrate forms thereof, and piperidine compounds of the formula: ##STR2## or isomers thereof as well as salt and/or hydrate forms thereof. In the above formulae, A represents a methylene group, an oxygen atom or a sulfur atom; B represents an oxygen atom or a sulfur atom; R.sup.1 and R.sup.2 independently represent a hydrogen atom, a lower alkyl group or an aralkyl group; R.sup.3 represents a hydrogen atom or an amino protecting group; Z represents an amino group or a protected amino group, a hydroxy group, or a reactive atom or group; m represents 1 or 2; and n represents the integer of 0 to 3.Piperidine compounds (I) possess an inhibitory activity against angiotensin-converting enzyme, and exhibit a long lasting hypotensive activity and are useful as antihypertensive agents. Piperidine compounds (II) are useful as intermediates for said piperidine compounds (I).Type: GrantFiled: May 24, 1988Date of Patent: November 21, 1989Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Shu Murakami, Tsuguo Ikebe, Ichiro Hakamada, Osamu Yaoka
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Patent number: 4742175Abstract: Polymorphically pure terfenadine, 1-(p-tert-butylphenyl)-4-[4'-(.alpha.-hydroxydiphenylmethyl)-1'-piperidiny l]-butanol, is prepared by carefully controlled recrystallization methods.Type: GrantFiled: June 30, 1987Date of Patent: May 3, 1988Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Timothy G. Fawcett, Christian T. Goralski, David W. Ziettlow
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Patent number: 4690708Abstract: A herbicide of the formula: ##STR1## in which: Z is N or CX',W, Y, Y', X, Z' and X' represent H, a halogen atom, NO.sub.2, CN or a polyhalogenoalkyl, alkyl or alkoxy group,R.sup.2 represents H, halogen, substituted alkyl, allyl, propargyl, CN, NR.sup.4 R.sup.5, C(X.sup.2)R.sup.7, C(X.sup.2)X.sup.3 R.sup.8, C(X.sup.2)NR.sup.4 R.sup.5, SO.sub.2 F, SO.sub.2 OR.sup.8, SO.sub.2 NR.sup.4 R.sup.5 or P(X.sup.2)R.sup.9 R.sup.10,R.sup.1 is halogen, X.sup.2 R.sup.3 or NR.sup.4 R.sup.5,R.sup.3 is optionally substituted alkyl or is allyl or propargyl,R.sup.4, R.sup.7 and R.sup.8 represent H, alkyl, cycloalkyl, phenyl, allyl, propargyl or the like,R.sup.5 represents R.sup.4, a cation or OR.sup.6, R.sup.6 being H, a cation or alkyl,X.sup.2 and X.sup.3 are O or S,R.sup.9 and R.sup.10 are H, alkyl, OH, OM or R.sup.1, andM is a cation.Type: GrantFiled: July 11, 1984Date of Patent: September 1, 1987Assignee: Rhone-Poulenc AgrochimieInventors: Alain Chene, Guy Borrod
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Patent number: 4645774Abstract: The invention relates to new aminoethoxybenzylalcohol derivatives of the formula (I) ##STR1## wherein R.sub.1 is hydrogen, halogen, trihalomethyl, alkyl having from one to 4 carbon atoms or alkoxy having from one to 4 carbon atoms;R.sub.2 is halogen, trihalomethyl, or alkoxy having from one to 4 carbon atoms;R.sub.3 and R.sub.4 stand for methyl or together with the adjacent nitrogen form an up to 8-membered ring optionally containing oxygen,and acid addition or quaternary ammonium salts thereof.The compounds of formula (I) are pharmacologically active, thus show enzyme-inducing effect. The pharmaceutical compositions containing them as active ingredient are also within the scope of the invention.Type: GrantFiled: December 2, 1985Date of Patent: February 24, 1987Assignee: Richter Gedeon Vegyeszeti Gyar RtInventors: Edit Toth, Jozsef Torley, Eva Palosi, Szabolcs Szeberenyi, Laszlo Szporny, Sandor Gorog, Istvan Hajdu
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Patent number: 4558131Abstract: Compounds which contain in their molecule both a hydroquinone monoether or resorcinol monoether radical and a polyalkylpiperidine radical are effective stabilizers for photographic dyes and their intermediates. In particular, they act as stabilizers against damage by light.Type: GrantFiled: December 15, 1983Date of Patent: December 10, 1985Assignee: Ciba-Geigy AGInventors: David G. Leppard, Jean Rody
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Patent number: 4551465Abstract: The invention relates to new piperidine derivatives of the formula (I) ##STR1## wherein R.sub.1 is halogen, trihalomethyl, alkyl having from one to 4 carbon atoms or alkoxy having from one to 4 carbon atoms; andR.sub.2 is hydrogen or alkyl having from one to 4 carbon atoms, and acid addition and quaternary ammonium salts thereof. According to another aspect of the invention there are provided processes for the preparation of these compounds. The compounds of the formula (I) are pharmacologically active. In particular, they inhibit the microsomal monooxigenase enzyme system of the liver. Pharmaceutical compositions containing them as active ingredient are also within the scope of the invention.Type: GrantFiled: December 27, 1983Date of Patent: November 5, 1985Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Edit Toth, Jozsef Torley, Eva Palosi, Szabolcs Szeberenyi, Laszlo Szporny, Sandor Gorog, Istvan Hajdu
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Patent number: 4361573Abstract: .alpha.,.alpha.-Diaryl-.beta.-(tert-amino)-propanols having the general formula: ##STR1## wherein R', R" and R.sup.1 to R.sup.10 represent certain specific substituent groups, exhibit a diuretic and saluretic activity.Pharmaceutical composition containing at least one compound of the general Formula II together with a pharmaceutically acceptable diluent or carrier. The pharmaceutical compositions may be in a form suitable for oral or parenteral administration.Type: GrantFiled: March 11, 1981Date of Patent: November 30, 1982Assignee: Temmler AGInventors: Wilhelm A. Behrendt, Bernhard Stieh
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Patent number: 4285958Abstract: Pharmaceutically useful compounds of the following formula: ##STR1## wherein R.sub.1 represents hydrogen or hydroxy; R.sub.2 represents hydrogen; or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; n is a positive whole integer of from 1 to 5; R.sub.3 is --CH.sub.3, --CH.sub.2 OH, --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; and A and B are individually hydrogen or hydroxy; with the provisos that at least one of A or B is hydrogen and one of A or B is other than hydrogen when R.sub.3 is --CH.sub.3 ; and pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: October 14, 1980Date of Patent: August 25, 1981Assignee: Richardson-Merrell Inc.Inventors: Albert A. Carr, Joseph E. Dolfini, George J. Wright
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Patent number: 4285957Abstract: Novel compounds of the following formula: ##STR1## wherein R.sub.1 is hydrogen or hydroxy; R.sub.2 is hydrogen; or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; n is an integer of from 1 to 5; R.sub.3 is --CH.sub.3, --CH.sub.2 OH, --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; and each of A and B is hydrogen or hydroxy; with the provisos that at least one of A or B is hydrogen and one of A or B is other than hydrogen when R.sub.3 is --CH.sub.3 ; and pharmaceutically acceptable salts thereof.Type: GrantFiled: October 14, 1980Date of Patent: August 25, 1981Assignee: Richardson-Merrell Inc.Inventors: Albert A. Carr, Joseph E. Dolfini, George J. Wright
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Patent number: 4260623Abstract: Compounds of the formula ##STR1## where R.sub.1 is hydrogen, lower alkyl containing one to three carbon atoms, cycloalkyl lower alkyl containing four to seven carbon atoms, or benzyl; and R.sub.2 is hydrogen, halogen, alkoxy containing one to three carbon atoms, trifluoromethyl; and pharmaceutically acceptable acid addition salts thereof are useful as anti-depressants.Type: GrantFiled: November 26, 1979Date of Patent: April 7, 1981Assignee: Warner-Lambert CompanyInventor: Horace A. De Wald