Nitrogen Or -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Hetero Ring Patents (Class 548/953)
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Patent number: 5488037Abstract: This invention relates to L-Arginine aldehyde derivatives, pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors and thromboembolic disorder agents.Type: GrantFiled: March 4, 1994Date of Patent: January 30, 1996Assignee: Eli Lilly and CompanyInventors: Daniel J. Sall, Robert T. Shuman
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Patent number: 5481005Abstract: The invention relates to N-sulfonyl derivatives of formulae (I) and (I)' ##STR1## to their preparation, and to pharmaceutical compositions in which they are present. The compounds of formulae (I) and (I)' have an affinity for the vasopressin and ocytocin receptors.Type: GrantFiled: November 28, 1994Date of Patent: January 2, 1996Assignee: SanofiInventors: Jean Wagnon, Paul de Cointet, Dino Nisato, Claude Plouzane, Claudine Serradeil-Legal, Bernard Tonnerre
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Patent number: 5476951Abstract: Method of synthesizing a 1,3,3 trinitroazetidine compound (TNAZ) comprising the steps of:selecting a compound of the formula I: ##STR1## wherein R' is one of hydrogen and an organic group and R is selected from the group consisting of electron withdrawing and electron donating groups; and,reacting the selected compound with a nitrolyzing agent such that a TNAZ compound is formed from the reaction.Type: GrantFiled: May 26, 1993Date of Patent: December 19, 1995Inventors: Paritosh R. Dave, Theodore Axenrod
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Patent number: 5462934Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is H or an optionally substituted hydrocarbon or acyl group; ring A is an optionally further substituted benzene ring; n is an integer of 1 to 10; R.sup.2, R.sup.3 and R.sup.4 are H or an optionally substituted hydrocarbon group; R.sup.3 and R.sup.4 may form an optionally substituted heterocyclic group, taken together with the adjacent nitrogen atom; k is an integer of 0 to 3; and m is an integer of 1 to 8; provided that when k=0 and m=2, n is an integer of not less than 2 or a pharmaceutically acceptable salt thereof, exhibiting excellent cholinesterase inhibitory activity and monoamine reuptake inhibitory activity, thus being useful as therapeutic/prophylactic medicaments of senile dementia.Type: GrantFiled: March 4, 1993Date of Patent: October 31, 1995Assignee: Takeda Chemical IndustriesInventors: Giichi Goto, Masaomi Miyamoto, Yuji Ishihara
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Patent number: 5412117Abstract: 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: GrantFiled: January 26, 1993Date of Patent: May 2, 1995Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Hiroshi Koga, Hiroyuki Nabata
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Patent number: 5401851Abstract: This invention provides novel phenyl and heterocyclic derivatives, their pharmaceutical formulations and their methods of use for antagonizing angiotensin II receptors in mammals.Type: GrantFiled: April 20, 1993Date of Patent: March 28, 1995Assignee: Eli Lilly and CompanyInventors: Donald B. Boyd, Kenneth L. Hauser, Sherryl L. Lifer, Winston S. Marshall, Alan D. Palkowitz, William Pfeifer, Jon K. Reel, Richard L. Simon, Mitchell I. Steinberg, Kumiko Takeuchi, K. Jeff Thrasher, Celia A. Whitesitt
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Patent number: 5395945Abstract: The compound, 3,3-dinitroazetidine, and a process of preparing 3,3-dinitroazetidine including reacting a mixture of 1-tertiary-butyl-3,3-dinitroazetidine and benzyl chloroformate to form 1-(benzyloxycarbonyl)-3,3-dinitroazetidine, reacting the 1-(benzyloxycarbonyl)-3,3-dinitroazetidine and trifluoromethanesulfonic acid to form 3,3-dinitroazetidinium trifluoromethanesulfonate, and neutralizing the 3,3-dinitroazetidinium trifluoromethanesulfonate with a base to form 3,3-dinitroazetidine are provided. Salts of the 3,3-dinitroazetidine and preparation of such salts are also disclosed.Type: GrantFiled: March 29, 1993Date of Patent: March 7, 1995Assignee: The United States of America as represented by the United States Department of EnergyInventor: Michael A. Hiskey
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Patent number: 5356893Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a halogen or hydrogen atom or a C.sub.1-6 alkyl or C.sub.1-6 alkoxy group;R.sup.2 represents a phenyl group optionally substituted by one or two substituents;R.sup.3 represents the group ##STR2## R.sup.4 and R.sup.5, which may be the same or different, each independently represent a hydrogen atom or a halogen atom, or a group selected from hydroxy, C.sub.1-6 alkoxy or C.sub.1-6 alkyl.The compounds may be used in the treatment or prophylaxis of depression and other CNS disorders.Type: GrantFiled: September 17, 1992Date of Patent: October 18, 1994Assignee: Glaxo Group LimitedInventors: John Bradshaw, John W. Clitherow, Ian B. Campbell
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Patent number: 5356890Abstract: The invention relates to novel S-nitroso derivatives of ACE inhibitors and to pharmaceutical compositions comprising the S-nitrosothiol derivatives of the invention together with a pharmaceutically acceptable carrier.The invention also relates to methods for treating various pathophysiological conditions including acute myocardial infarction, left ventricular dysfunction without overt heart failure, hypertension, pulmonary hypertension, congestive heart failure, angina pectoris, vascular thrombosis, Raynauds syndrome, scleroderma, toxemia of pregnancy, acute renal failure, diabetic nephropathy, and renal artery stenosis, and to methods of inhibiting ACE and effecting vasodilation comprising administering the S-nitrosothiol derivatives of the ACE inhibitors of the invention to an animal.Type: GrantFiled: February 4, 1993Date of Patent: October 18, 1994Assignee: Brigham and Women's HospitalInventors: Joseph Loscalzo, John Cooke
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Patent number: 5336784Abstract: A process of preparing 1,3,3-trinitroazetidine including forming a 5-hydroxymethyl-5-nitro-1-alkyltetrahydro-1,3-oxazine, e.g., reacting a 1,3,5-trialkyl hexahydrotriazine and tris(hydroxymethyl)nitromethane, ring opening said 5-hydroxymethyl-5-nitro-1-alkyltetrahydro-1,3-oxazine to form a 3-alkylamino-2-hydroxymethyl-2-nitro-1-propanol salt, ring closing said 3-alkylamino-2-hydroxymethyl-2-nitro-1-propanol salt to form a 3-hydroxymethyl-3-nitro-1-alkylazetidine salt, nitrating said 3-hydroxymethyl-3-nitro-1-alkylazetidine salt to form a 1-alkyl-3,3-dinitroazetidine, and converting said 1-alkyl-3,3-dinitroazetidine into 1,3,3-trinitroazetidine is disclosed.Type: GrantFiled: June 7, 1993Date of Patent: August 9, 1994Assignee: The Regents of the University of CaliforniaInventors: Michael A. Hiskey, Michael D. Coburn
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Patent number: 5268374Abstract: The present invention relates to renin inhibiting compounds of the formula: ##STR1##Type: GrantFiled: May 22, 1991Date of Patent: December 7, 1993Assignee: Abbott LaboratoriesInventors: Anthony K. L. Fung, William R. Baker, Yoek-Lin Armiger, Saul H. Rosenberg, Biswanath De, Jacob J. Plattner, Steven A. Boyd, Dale J. Kempf, Hing L. Sham, Hollis D. Kleinert, Robert A. Mantei
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Patent number: 5260310Abstract: Novel compounds of the formula ##STR1## wherein Q, R.sup.1 and R.sup.2 are described herein, are disclosed along with pharmaceutical compositions, methods of use, and process for producing compounds of formula I which starts from the corresponding .beta.-hydroxycarboxylic acids.Type: GrantFiled: August 12, 1992Date of Patent: November 9, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Romano Derungs, Hans P. Marki, Henri Stalder, Andre Szente
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Patent number: 5252566Abstract: Thrombin inhibitors represented by the formula ##STR1## as provided wherein A is e.g. phenylglycyl, and phenylalanyl, .alpha.-methylphenylalanine and .alpha.-methylphenylglycine wherein the amino group is preferably substituted with lower alkyl alkanoyl or lower alkoxycarbonyl, or a bicyclo group e.g. 1,2,3,4-tetrahydroisoquinolin-1-yl. Also provided are a method for inhibiting clot formation in man and animals, pharmaceutical formulations useful in the method and intermediates for the inhibitors.Type: GrantFiled: October 16, 1992Date of Patent: October 12, 1993Assignee: Eli Lilly and CompanyInventor: Robert T. Shuman
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Patent number: 5238955Abstract: Antitumor acting platinum(II or IV) complexes of the general formula ##STR1## where B represents a phenyl-C.sub.1 -C.sub.4 -alkyl radical which is optionally substituted in the phenyl nucleus by the radical R.sub.1 and R.sub.1 is hydrogen, halogen, trihalogen methyl, C.sub.1 -C.sub.6 -alkyl, hydroxy, C.sub.1 -C.sub.6 -alkoxy or C.sub.2 -C.sub.6 -alkanoyloxy or where B together with the structural part H.sub.2 N-CR.sub.2 < forms a tetrahydroisoquinoline radical, if B contains benzyl and R.sub.2 hydrogen and the benzyl radical in the 2-position contains the CH.sub.2 -radical or where B together with the structural part --CR.sub.2 < represents a tetrahydronaphthyl radical in which one CH.sub.2 group is optionally replaced by oxygen, or where B together with the structural part --CR.sub.2 < represents a decahydronaphthyl radical or an indanyl radical; R.sub.2 represents hydrogen, C.sub.1 -C.sub.6 -alkyl, phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, it also being possible for the phenyl ring of this group R.Type: GrantFiled: November 25, 1992Date of Patent: August 24, 1993Assignee: Asta Pharma AGInventors: Henri Brunner, Peter Hankofer, Friedrich Maiterth, Jurgen Engel, Wolfgang Schumacher, Peter Hilgard, Rainer Voegeli
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Patent number: 5204338Abstract: The invention relates to oxalylamino acid derivatives of the formula I ##STR1## in which R and R' are identical or different and are C.sub.1 -C.sub.6 -alkyl or hydrogen,R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sup.2 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.3 -alkoxy, carboxyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, aryl, SH, NH.sub.2 or halogen, where the alkyl radicals are unsubstituted or substituted by aryl, OH, SH or NH.sub.2orR.sup.1 and R.sup.2 together are a C.sub.2 -C.sub.4 -alkylene chain and the compounds in their predominantly pure D- and L-form and the physiologically tolerable salts.The compounds are distinguished as excellent inhibitors of prolyl hydroxylase and lysine hydroxylase.Type: GrantFiled: May 10, 1991Date of Patent: April 20, 1993Assignee: Hoechst AktiengesellschaftInventors: Ekkehard Baader, Harald Burghard, Volkmar Gunzler-Pukall
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Patent number: 5199968Abstract: Oxalic acid derivatives of the formula IA--CO--COO--Y--X--D Iwhere A is an unsubstituted or substituted azetidine ring which is bonded via its nitrogen atom, Y is unsubstituted or substituted alkylene, X is oxygen or sulfur and D is unsubstituted or substituted alkyl or alkenyl or is monocyclic or polycyclic unsubstituted or substituted cycloalkyl, cycloalkylmethyl, cycloalkenyl or cycloalkenylmethyl or unsubstituted or substituted phenyl, phenylalkyl or phenylalkenyl, their preparation and growth regulators containing them.Type: GrantFiled: March 9, 1992Date of Patent: April 6, 1993Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Wilhelm Rademacher, Michael Keil, Albrecht Harreus
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Patent number: 5194588Abstract: The invention concerns pharmaceutically useful trifluoromethyl ketone substituted di-, tri- and tetra-peptide derivatives of the formulae Ia, Ib, Ic set out hereinafter, and salts thereof, which are inhibitors of human leukocyte elastase. Also described herein are pharmaceutical compositions containing a peptide derivative and processes and intermediates for use in the manufacture of the peptide derivatives.Type: GrantFiled: March 9, 1990Date of Patent: March 16, 1993Assignee: ICI Americas Inc.Inventors: Philip D. Edwards, John A. Schwartz, Mark M. Stein, Diane A. Trainor, Richard A. Wildonger
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Patent number: 5183903Abstract: This invention relates to an improved process for the preparation of 3-phenoxy-1-azetidinecarboxamides of Formula I which are useful ##STR1## in the treatment of epileptic seizures. Under Formula I, n is 1 to 3, X is H, halogen, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, acetyl, or aminocarbonyl, and R is H or methyl. This process involves heating a 3-phenoxyazetidine with urea to obtain the Formula I compound. Urea is inexpensive and easily removed by washing the solid Formula I product with water.Type: GrantFiled: November 26, 1991Date of Patent: February 2, 1993Assignee: A. H. Robins Company, IncorporatedInventors: William J. Welstead, Jr., Young S. Lo
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Patent number: 5166361Abstract: This invention relates to novel methods for converting a diastereomeric mixture of S-protected derivatives of an orally active inhibitor of an angiotensin-converting enzyme (ACE) and its analogues into its separate optically resolved diastereomeric components. Specifically the invention relates to methods for the preparation of optically purified captopril and its analogs from racemic precursors. This resolution process is achieved through the fractional crystallization of S-protected derivatives of captopril and its precursors, which derivatives are useful for the reason that they are (1) easily prepared from novel precursors, (2) resolvable to their optically purified stereoisomeric species and (3) convertible to non-derivatized stereoisomeric species which correspond to the pharmacologically active inhibitor and its analogues. Novel methods for preparing the derivatives and their precursors are also noted herein. In addition, the novel derivatives and their precursors are also described herein.Type: GrantFiled: September 25, 1991Date of Patent: November 24, 1992Assignee: Sepracor, Inc.Inventor: Charles M. Zepp
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Patent number: 5163992Abstract: Oxalic acid derivatives of the formula IA--CO--COO--Y--X--D Iwhere A is an unsubstituted or substituted azetidine ring which is bonded via its nitrogen atom, Y is unsubstituted or substituted alkylene, X is oxygen or sulfur and D is unsubstituted or substituted alkyl or alkenyl or is monocyclic or polycyclic unsubstituted or substituted cycloalkyl, cycloalkylmethyl, cycloalkenyl or cycloalkenylmethyl or unsubstituted or substituted phenyl, phenylalkyl or phenylalkenyl, their preparation and growth regulators containing them.Type: GrantFiled: July 30, 1991Date of Patent: November 17, 1992Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Wilhelm Rademacher, Michael Keil, Albrecht Harreus
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Patent number: 5091526Abstract: Biologically active, enantiomerically substantially pure intermediates of trans-hexahydro-benzo[d]naphtho[2,1-b]azepines are prepared.The present invention involves a process for preparing compounds of the general formula 3: ##STR1## wherein: R* is ##STR2## Each R.sup.1 is independently H or alkyl; Q is methylene, --O-- or --S--;m and n are independently variable and may each have a value of 0, 1 or 2, with the provisos that the sum of m and n is not greater than 3, that m may not equal zero when Q is --O-- or --S--, and that when Q is --CH.sub.2 --, m and n cannot both be zero;X is hydrogen, halo, alkyl, alkylthio, alkylsulfinyl, alkylsufonyl, hydroxy, alkoxy or trifluoromethyl;Y is hydrogen, hydroxy, alkoxy, --OC(O)NR.sup.2 R.sup.3, --OC(O)--R.sup.9, --N(R.sup.1).sub.2, --NHC(O)R.sup.1 or --OP(O)(OH)OR.sup.1,R.sup.2 and R.sup.3 are the same or different and each is hydrogen (provided that both are not hydrogen), alkyl, aralkyl, cycloalkyl, aryl, hydroxyalkyl, or alkoxyalkyl;in addition, when one of R.sup.Type: GrantFiled: January 8, 1991Date of Patent: February 25, 1992Assignee: Schering CorporationInventors: Joel G. Berger, John W. Clader
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Patent number: 5089492Abstract: Acylamino carboxylic acid derivatives corresponding to the formula I ##STR1## in which the groups R.sup.1, R.sup.2, R.sup.3, Z.sup.1 and Z.sup.2 represent functional groups specified in the claims. The acylamino carboxylic acid derivatives have valuable pharmacological properties which, in particular, favorably influence nitrogen metabolism. The compounds are useful as active ingredients in pharmaceutical and/or dietetic compositions for treatment or prevention of nitrogen metabolism disturbances in large mammals caused, for example, by liver or kidney damage.Type: GrantFiled: May 24, 1990Date of Patent: February 18, 1992Assignees: Kali-Chemie AG, Pfrimmer Kabi GmbH & Co. KGInventors: Klaus Gerling, Henning Heinemanmn, Andreas Meier, Klaus Langer
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Patent number: 5077288Abstract: The invention relates to the compounds of general formula I: ##STR1## in which: m represents an integer from 2 to 4,n and p, which may be identical or different, each represent an integer from 1 to 3,q represents 0 or 1, andR represents:either a group of formula (A): ##STR2## or a radical of formula (B): ##STR3## or a 2,4-dioxo-1,2,3,4-tetrahydroquinazolinyl radical, on condition, however, that, in this case, n and p do not simultaneously represent the number 2,or a benzhydryloxy group,or a 1-oxophthalazinyl radical,or a 5-oxothiazolo[3,2-A]pyrimidinyl radical,or a group of formula C: ##STR4## their possible stereoisomers and their addition salts with a pharmaceutically acceptable inorganic or organic acid.The compounds of formula I are medicinal products with useful 5-HT.sub.2 - and .alpha..sub.1 -antagonistic activities.Type: GrantFiled: March 20, 1990Date of Patent: December 31, 1991Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Francis Colpaert, Michel Laubie
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Patent number: 5073646Abstract: New azetidines, characterized in that they correspond to the general formula (I) ##STR1## in which R.sub.3 represents an amino radical, an alkylamino radical, a dialkylamino radical, a cycloalkylamino radical, an acylamino radical, an alkylacylamino radical, an aminomethyl radical, an alkylaminomethyl radical, an acylaminomethyl radical or an alkylacylaminomethyl radical, in which radicals each acyl fragment may be substituted with one or more halogen, especially fluorine, atoms; and R.sub.1, R.sub.2, R.sub.4, R.sub.5 and R.sub.6 represent a hydrogen atom or a lower alkyl radical, with the proviso that at least one of them represents a lower alkyl radical, and also their salts.Type: GrantFiled: June 20, 1990Date of Patent: December 17, 1991Assignee: Laboratorios Del Dr. Esteve, S.A.Inventors: Augusto C. Pinol, Jordi F. Constansa, Juan P. Corominas
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Patent number: 5055450Abstract: The invention concerns pharmaceutically useful trifluoromethyl ketone substituted di-, tri- and tetra-peptide derivatives of the formulae Ia, Ib, Ic set out hereinafter, and salts thereof, which are inhibitors of human leukocyte elastase. Also described herein are pharmaceutical compositions containing a peptide derivative and processes and intermediates for use in the manufacture of the peptide derivatives.Type: GrantFiled: March 13, 1990Date of Patent: October 8, 1991Assignee: ICI Americas Inc.Inventors: Philip D. Edwards, John A. Schwartz, Mark M. Stein, Diane A. Trainor, Richard A. Wildonger
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Patent number: 5053392Abstract: Disclosed are novel amino acid derivatives of the formula: ##STR1## wherein X is H, amidino or ##STR2## Y is H, amino or ##STR3## Z is ##STR4## OR.sub.1 or a naturally occurring L-amino acid, bounded to the carbon atom at the .alpha.-amino position;R is alkyl, aryl or aralkyl;R.sub.1 and R.sub.2 are independently H, alkyl, aryl, aralkyl or allyl;m is 1 through 5;n is 0 through 4; andpharmaceutically acceptable salts thereof, that inhibit platelet aggregation and thrombus formation in mammalian blood.Type: GrantFiled: December 1, 1989Date of Patent: October 1, 1991Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Scott I. Klein, Bruce F. Molino
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Patent number: 5025005Abstract: Novel lipid derivatives of the formula ##STR1## [wherein R.sup.1 is alkyl or alkylcarbamoyl; R.sup.2 is hydrogen, hydroxy which may be substituted, amino which may be substituted or cyclic amino; R.sup.3 is a chemical binding or alkylene which may be substituted; R.sup.4 is hydrogen, alkyl or aralkyl; X and Y are independently O, S or an imino group which may be substituted, and when Y is an imino group, Y, together with the imino group represented by X or R.sup.4, may form a ring; and Z is imino or a nitrogen-containing heterocyclic ring which may be substituted] and salts thereof have inhibiting activity on platelet activating factor and are useful as a preventive or therapeutic agent for a variety of circulatory diseases and allergic disorders and also as an antineoplastic agent.Type: GrantFiled: July 23, 1990Date of Patent: June 18, 1991Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Kohei Nishikawa, Susumu Tsushima
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Patent number: 5023335Abstract: 1,2-Bis(aminomethyl)-cyclobutane-platinum complexes having an anti-tumor activity.Type: GrantFiled: September 25, 1990Date of Patent: June 11, 1991Assignee: ASTA Pharma AktiengesellschaftInventors: Wolfgang Schumacher, Johannes Respondek, Jurgen Engel, Jorg Pohl, Rainer Voegeli, Peter Hilgard
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Patent number: 5017708Abstract: A compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 each is hydrogen, hydroxy, oxo, halogen, azido, amino, C.sub.1 -C.sub.3 alkylamino, or aminomethyl, in which said amino, C.sub.1 -C.sub.3 alkylamino and aminomethyl each is optionally substituted by one or two members selected from the group consisting of C.sub.1 -C.sub.3 alkyl and amino-protecting group; n is an integer of 1 to 3; p and q each is an integer of 0 to 3 with proviso that p+q=1 to 4 or acid-addition salts thereof, being useful materials for preparing side chains of antibacterial quinolonecarboxylic acids, cephalosporines, or other antibiotics.Type: GrantFiled: September 8, 1989Date of Patent: May 21, 1991Assignee: Shionogi & Co., Ltd.Inventors: Masaru Ogata, Hiroshi Matsumoto, Sumio Shimizu, Shiro Kida
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Patent number: 5002964Abstract: The invention relates to novel nitroso compounds having the formula: ##STR1## wherein, R is hydroxy, NH.sub.2, NHR.sup.4, NR.sup.4 R.sup.5 or C.sub.1 -C.sub.7 alkoxy, wherein R.sup.4 and R.sup.5 are C.sub.1 -C.sub.4 alkyl, aryl, or C.sub.1 -C.sub.4 alkyl substituted by aryl;R.sup.1 is hydrogen, C.sub.1 -C.sub.7 alkyl or C.sub.1 -C.sub.7 alkyl substituted by phenyl, amino, guanidino, NHR.sup.6 or NR.sup.6 R.sup.7, wherein R.sup.6 and R.sup.7 are methyl, or C.sub.1 -C.sub.4 acyl;R.sup.3 is hydrogen, C.sub.1 -C.sub.7 alkyl or C.sub.1 -C.sub.7 alkyl substituted by phenyl;n is 0 to 2;A is hydrogen,lower C.sub.1 -C.sub.7 alkyl,lower C.sub.2 -C.sub.7 alkylene,lower C.sub.2 -C.sub.7 alkylene substituted by hydroxy, C.sub.1 -C.sub.4 alkyl, aryl, ora C.sub.4 -C.sub.7 ring which may be fused to a benzene ring;B is hyrogen,lower C.sub.1 -C.sub.7 alkyl,phenyl,lower C.sub.1 -C.sub.7 substituted by phenyl, hydroxy, guanidino, amino, imidazoyl, indolyl, mercapto, mercapto substituted by lower C.sub.1 -C.sub.Type: GrantFiled: June 15, 1988Date of Patent: March 26, 1991Assignee: Brigham & Women's HospitalInventor: Joseph Loscalzo
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Patent number: 4996316Abstract: A process for the preparation of tertiary N,N-dimethylamines by the reaction of primary amines, formaldehyde, and hydrogen under pressure and at elevated temperature in the presence of a nickel-containing hydrogenation catalyst in the liquid phase. The hydrogenation catalyst is suspended in a solvent, the nickel concentration is 0.1 to 10% by weight, based on the primary amine. The starting materials are separate from each other, brought to 80.degree. to 150.degree. C. and 1 to 15 MPa and fed into the catalyst suspension simultaneously with stirring and reacted in one step to form the tertiary N,N-dimethylamines.Type: GrantFiled: December 24, 1988Date of Patent: February 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
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Patent number: 4988688Abstract: 4-(N-Substituted amino)-2-butynyl-1-ureas and thioureas and derivatives thereof are described, as well as methods for the preparation and pharmaceutical compositions of same, which are useful as centrally acting muscarinic agents and are useful as analgesic agents for the treatment of pain, as sleep aids and as agents for treating the symptoms of senile dementia, Alzheimer's disease, Huntington's chorea, tardive dyskinesia, hyperkinesia, mania, or similar conditions of cerebral insufficiency characterized by decreased cerebral acetylcholine production or release.Type: GrantFiled: August 2, 1989Date of Patent: January 29, 1991Assignee: Warner-Lambert CompanyInventors: Jeffrey A. Kester, Walter H. Moos, Anthony J. Thomas
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Patent number: 4977141Abstract: Non-peptidyl compounds characterized generally as aminoacyl aminodiol carbamates are useful as renin inhibitors for the treatment of hypertension.Type: GrantFiled: October 1, 1987Date of Patent: December 11, 1990Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran
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Patent number: 4968341Abstract: Novel substituted aryloxyureas, processes for their production, and herbicides comprising them as active ingredients are provided.The substituted aryloxyureas exhibit an excellent herbicidal efficacy against weeds when applied, for example, to the weeds in a wide range of period from a preemergence stage to a growth stage.The substituted aryloxyureas of the invention have the excellent advantage of maintaining high safety on crops or crop plants in spite of their herbicidal efficacy.Type: GrantFiled: August 16, 1988Date of Patent: November 6, 1990Assignees: Kumiai Chemical Industry Co., Mitsui Petrochemical Industries, Ltd.Inventors: Isao Hashimoto, Tatsuyodihi Ishida, Kazutaka Tsuru, Yuji Yamada, Takeshige Miyazawa, Yasuo Nakamura, Susumu Katou, Katsuya Takahashi
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Patent number: 4954518Abstract: This invention relates to a 4H-1-benzopyran-4-one derivative represented by the formula: ##STR1## or a salt thereof, a process for producing the same and a pharmaceutical composition comprising the same as active ingredient.Type: GrantFiled: October 7, 1988Date of Patent: September 4, 1990Assignee: Toyama Chemical Company, Ltd.Inventors: Shuntaro Takano, Chosaku Yoshida, Takihiro Inaba, Keiichi Tanaka, Ryuko Takeno, Hideyoshi Nagaki, Tomoya Shimotori, Shinji Makino
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Patent number: 4946839Abstract: This invention relates to novel azetidines and derivative thereof, as well as to pharmaceutical compositions and methods of treating memory and learning disorders. Another aspect of the invention relates to a method of utilizing the compounds and compositions as biological tools and materials for characterizing excitatory amino acid receptor systems. A further aspect of the invention relates to a method of treating PCP toxicity and abuse.Type: GrantFiled: July 17, 1987Date of Patent: August 7, 1990Assignee: Fidia-Georgetown Institute for the NeurosciencesInventors: Alan P. Kozikowskip, Jarda T. Wroblewski, Erminio Costa
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Patent number: 4944789Abstract: Azetidine derivatives of the formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or C.sub.1 -C.sub.3 -alkyl, A is --XR.sup.3 or --N(R.sup.5)--OR.sup.4, X is oxygen or sulfur, R.sup.3 is C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.20 -haloalkyl, C.sub.3 -C.sub.18 -alkenyl, C.sub.3 - or C.sub.4 -alkynyl, bridged C.sub.3 -C.sub.12 -cycloalkyl or C.sub.4 -C.sub.12 -alkylcycloalkyl, the cycloalkyl radicals or alkylcycloalkyl radicals being unsubstituted or substituted by C.sub.1 -C.sub.5 -alkyl or cyclohexyl, R.sup.4 is C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.12 -haloalkyl, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.12 -alkoxyalkyl, C.sub.3 -C.sub.18 -alkenyl, C.sub.3 -C.sub.18 -haloalkenyl, C.sub.3 - or C.sub.4 -alkynyl, C.sub.3 -C.sub.12 -cycloalkyl or C.sub.4 -C.sub.12 -cycloalkylalkyl, C.sub.3 -C.sub.16 -alkoxycarbonylalkyl or unsubstituted or substituted C.sub.7 -C.sub.20 -aralkyl and R.sup.5 is hydrogen or C.sub.1 -C.sub.3 -alkyl, and agents and methods for regulating plant growth.Type: GrantFiled: July 7, 1989Date of Patent: July 31, 1990Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Wilhelm Rademacher, Johann Jung, Albrecht Harreus
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Patent number: 4943641Abstract: The 3-aminoazetidine, its salts, new intermediates of formula ##STR1## wherein X' represents hydrogen or a protecting group and both X" represent hydrogen or, together with the nitrogen atom, a phthalimido group, X' and both X" not being hydrogen at the same time; a process for the preparation of the 3-aminoazetidine, starting from a 1-protected 3-sulfonyloxyazetidine by reaction with the potassium phthalimide and transformation of the above mentioned intermediates.Type: GrantFiled: February 17, 1989Date of Patent: July 24, 1990Assignee: SanofiInventors: Dino Nisato, Marco Frigerio
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Patent number: 4940703Abstract: The present invention provides a compound of formula I or a salt or prodrug thereof: ##STR1## wherein the dotted line represents an optional chemical bond in one of the two possible positions;A represents a group of formula II: ##STR2## in which R.sup.1 represents hydrogen, hydroxy, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 alkoxy, benzyloxy, hydroxy (C.sub.1-6)alkyl, halogen, amino, cyano, nitro, --CONR.sup.6 R.sup.7 or --SO.sub.2 NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 independently represent hydrogen, halogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl;R.sup.2 represents hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkylcarbonyl;V represents nitrogen, --CH or --C--; andW represents oxygen, sulphur or --NR.sup.8, in which R.sup.8 represents hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.Type: GrantFiled: April 4, 1989Date of Patent: July 10, 1990Assignee: Merck Sharp & Dohme LimitedInventors: Raymond Baker, Clare O. Kneen, John Saunders, Christopher Swain
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Patent number: 4918187Abstract: The present invention relates to compounds of the formula ##STR1## wherein R.sub.c is carboxy, esterified carboxy or amidated carboxy; R.sub.2 is hydrogen or lower alkyl or joins with R.sub.a and R.sub.b and the atoms therebetween to form a fused ring ##STR2## and either R.sub.a is methyl and R.sub.b is ##STR3## or R.sub.2 and R.sub.b and the atoms therebetween form a group ##STR4## wherein R.sub.3 and R.sub.4 are either both hydrogen, or together are propylene, butylene, or with the two atoms to which they are attached form a benzene ring. Methods of manufacture and use thereof in the production of angiotensin converting enzyme inhibitors are disclosed.Type: GrantFiled: September 27, 1988Date of Patent: April 17, 1990Assignee: Ciba-Geigy CorporationInventor: Stephen K. Boyer
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Patent number: 4910190Abstract: The invention concerns pharmaceutically useful trifluoromethyl ketone substituted di-, tri- and tetra-peptide derivatives of the formulae Ia, Ib, Ic set out hereinafter, and salts thereof, which are inhibitors of human leukocyte elastase. Also described herein are pharmaceutical compositions containing a peptide derivative and processes and intermediates for use in the manufacture of the peptide derivatives.Type: GrantFiled: January 20, 1987Date of Patent: March 20, 1990Assignee: ICI Americas Inc.Inventors: Scott H. Bergeson, Philip D. Edwards, John A. Schwartz, Andrew Shaw, Mark M. Stein, Diane A. Trainor, Richard A. Wildonger, Donald J. Wolanin
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Patent number: 4876359Abstract: Novel .gamma.-butyrolactone derivatives having strong ACE inhibitory activity are provided. They are represented by the following general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and mean individually a hydrogen atom or a straight-chain or branched alkyl or cycloalkyl group, or R.sup.1 and R.sup.2 are bonded together to mean an alkylene group having 2-6 carbon atoms, R.sup.3 denotes a hydrogen atom or a lower alkyl, aralkyl, amino lower alkyl or lower alkoxycarbonylamino lower alkyl group, R.sup.4 means a lower alkyl, cycloalkyl or aralkyl group, R.sup.5 means a hydrogen atom or a lower alkyl group, or R.sub.4 and R.sub.5 are bonded together to denote an alkylene group having 2-4 carbon atoms, and R.sup.6 stands for a hydrogen atom or a lower alkyl or aralkyl group; or a pharmacologically acceptable salt thereof.Type: GrantFiled: October 1, 1987Date of Patent: October 24, 1989Assignee: SS Pharmaceutical Co., Ltd.Inventors: Hiroshi Hasegawa, Noriaki Shioiri, Tadashi Narita, Tatsuhiko Katori
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Patent number: 4855452Abstract: Process for the preparation of a compound of formula or a salt thereof ##STR1## wherein R.sub.1 represents a hydrogen atom or a group of formula R.sub.2 SO.sub.2 or phenyl--CH(R.sub.3)-- wherein R.sub.2 represents a phenyl, tolyl or C.sub.1-4 alkyl group and R.sub.3 represents a hydrogen atom or a phenyl or C.sub.1-4 alkyl group, which process comprises contacting nickel in an oxidation state of at least 3 with a 3-hydroxymethyl azetidine derivative of formula ##STR2## wherein R.sub.4 represents a group of formula R.sub.2 SO.sub.2 or phenyl--CH(R.sub.3)-- and R.sub.5 represents a hydrogen atom or a hydroxymethyl group or a group of formula COOH or a salt thereof, followed, where R.sub.5 is not a hydrogen atom, by the decarboxylation of the compound of the 3,3-dicarboxylic intermediate product or a salt thereof and, if desired to produce a compound in which R.sub.1 represents a hydrogen atom, by deprotection of the N-atom.Type: GrantFiled: June 9, 1988Date of Patent: August 8, 1989Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Jannetje de Waal, David W. Sopher
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Patent number: 4822895Abstract: The 3-aminoazetidine, its salts, new intermediates of formula ##STR1## wherein X' represents hydrogen or a protecting group and both X" represent hydrogen or, together with the nitrogen atom, a phthalimido group, X' not and both X" being hydrogen at the same time; a process for the preparation of the 3-aminoazetidine, starting from a 1-protected 3-sulfonyloxyazetidine by reaction with the potassium phthalimide and transformation of the above mentioned intermediates.Type: GrantFiled: February 21, 1985Date of Patent: April 18, 1989Assignee: Societe Anonyme - SANOFIInventors: Dino Nisato, Marco Frigerio
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Patent number: 4812581Abstract: Preparation of azetidine-3-carboxylic acid or a salt thereof from N-benzylazetidine-3-carboxylic acid or a salt thereof by catalytically hydrogenating the N-benzylazetidine-3-carboxylic compound in the presence of water, formate ions, and ammonium and/or alkylammonium ions. Novel ammonium and alkylammonium salts are claimed.Type: GrantFiled: October 28, 1987Date of Patent: March 14, 1989Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Jannetje de Waal
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Patent number: 4791133Abstract: This invention relates to leukotriene B.sub.4 antagonists having the structure ##STR1## and the pharmaceutically acceptable addition salts thereof; wherein R.sup.1 is lower alkyl having 1-10 carbon atoms; or lower alkenyl or alkynyl having 2-10 carbon atoms; or lower alkadienyl having 3-10 carbon atoms; or lower alkadiynyl or alkenynyl having 4-10 carbon atoms;wherein R.sup.2 and R.sup.3 are the same or different and represent hydrogen or lower alkyl having 1-6 carbon atoms;wherein X is CH.dbd.CH, S, or O;wherein Y is CH.dbd.CH or C.tbd.C;wherein Z is OR.sup.4 or NR.sup.5 R.sup.6, and wherein R.sup.4 represent H, lower alkyl having 1-6 carbon atoms, or a pharmaceutically acceptable cation, and wherein R.sup.5 and R.sup.6 act independently and represent H or lower alkyl having 1-6 carbon atoms, or R.sup.5 and R.sup.Type: GrantFiled: June 26, 1987Date of Patent: December 13, 1988Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
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Patent number: 4778577Abstract: Process for the preparation of a compound of formula or a salt thereof ##STR1## wherein R.sub.1 represents a hydrogen atom or a group of formula R.sub.2 SO.sub.2 or phenyl--CH(R.sub.3)--wherein R.sub.2 represents a phenyl, tolyl or C.sub.1-4 alkyl group and R.sub.3 represents a hydrogen atom or a phenyl of C.sub.1-4 alkyl group, which process comprises contacting nickel in an oxidation state of at least 3 with a 3-hydroxymethyl azetidine derivative of formula ##STR2## wherein R.sub.4 represents a group of formula R.sub.2 SO.sub.2 or phenyl--CH(R.sub.3)--and R.sub.5 represents a hydrogen atom or a hydroxymethyl group or a group of formula COOH or a salt thereof, followed, where R.sub.5 is not a hydrogen atom, by the decarboxylation of the compound of the 3,3-dicarboxylic intermediate product or a salt thereof and, if desired to produce a compound in which R.sub.1 represents a hydrogen atom, by deprotection of the N-atom.Type: GrantFiled: April 16, 1986Date of Patent: October 18, 1988Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Jannetje De Waal, David W. Sopher
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Patent number: 4769365Abstract: Compound for use in a method for treatment of the human or animal body by therapy, characterized in that the compound is a carboxy azetidine derivative of the general formula I or a pharmaceutically acceptable salt, ester, amide, alkylamide, hydrazide or alkylhydrazide thereof: ##STR1## in which: X represents one of the groups CH.sub.2, CHR or CR.sub.2.Y represents one of the groups CH.sub.2, CHR, CR.sub.2 or CH.CO.sub.2 H andZ represents one of the groups CH.sub.2, CHR, CR.sub.2 or CH.CO.sub.2 H;the or each R independently represents an alkyl, alkenyl or cycloalkyl group or an aryl or aralkyl group optionally substituted on the aryl nucleus by one or more of the same or different substituents selected from halogen atoms, alkyl groups and alkoxy groups;and one but only one of Y and Z must represent a CH.CO.sub.2 H group.Type: GrantFiled: December 3, 1986Date of Patent: September 6, 1988Assignee: Shell Oil CompanyInventors: James B. M. Gellatly, John G. Martin
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Patent number: 4766110Abstract: Novel inhibitors of angiotensin converting enzyme are disclosed which have the general formula ##STR1## wherein R.sub.1 and/or R.sub.3 form complex amides and imides thereof, R.sub.4 and R.sub.5 form with --N--C-- a 4-6 membered ring structure as described and the other R substituents are selected from a variety of disclosed groups.Type: GrantFiled: October 31, 1986Date of Patent: August 23, 1988Inventors: James W. Ryan, Alfred Chung
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Patent number: 4737518Abstract: Novel lipid derivatives of the formula ##STR1## [wherein R.sup.1 is alkyl or alkylcarbamoyl; R.sup.2 is hydrogen, hydroxy which may be substituted, amino which may be substituted or cyclic amino; R.sup.3 is a chemical binding or alkylene which may be substituted; R.sup.4 is hydrogen, alkyl or aralkyl; X and Y are independently O, S or an imino group which may be substituted, and when Y is an imino group, Y, together with the imino group represented by X or R.sup.4, may form a ring; and Z is imino or a nitrogen-containing heterocyclic ring which may be substituted] and salts thereof have inhibiting activity on platelet activating factor and are useful as a preventive or therapeutic agent for a variety of circulatory diseases and allergic disorders and also as an antineoplastic agent.Type: GrantFiled: September 12, 1986Date of Patent: April 12, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Kohei Nishikawa, Susumu Tsushima, Yoshio Kozai