The Ring Nitrogen Is Bonded Directly To Two Ring Carbons Of The Same Cyclo Which Carbons Are Members Of One Cyclo Only (e.g., Cyclopenta(c)pyrroles, Etc.) Patents (Class 548/515)
  • Patent number: 5753690
    Abstract: A compound of the formula ##STR1## in which A, R.sup.1 and n have the meanings stated in the description are described. The novel compounds are suitable for controlling diseases.
    Type: Grant
    Filed: February 3, 1997
    Date of Patent: May 19, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Steiner, Rainer Munschauer, Thomas Hoger, Liliane Unger, Hans-Jurgen Teschendorf
  • Patent number: 5693824
    Abstract: A process for the preparation of mixed crystals of 1,4-diketopyrrolo?3,4-c!pyrroles, consisting of 1 mol each of two different compounds of formula ##STR1## by heating a corresponding mixture in solid form to the temperature range from 220.degree. to 380.degree. C.A and B are, for example, each a group of formula ##STR2## wherein R.sub.1 and R.sub.2 are each independently hydrogen, chloro, bromo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylamino, phenyl or --CN, G is --O--, --NR.sub.7 --, --N.dbd.N-- or --SO.sub.2 --, R.sub.3 and R.sub.4 are hydrogen, and R.sub.7 is hydrogen, methyl or ethyl.The mixed crystals and solid solutions obtained are excellently suited for pigmenting high molecular weight material.
    Type: Grant
    Filed: September 12, 1996
    Date of Patent: December 2, 1997
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Jin Mizuguchi, Zhimin Hao, Olof Wallquist, Abul Iqbal
  • Patent number: 5541217
    Abstract: The 4-arylcyclopenta[c]pyrroles of the following formula are effective analgesics: ##STR1## including stereoisomers and pharmaceutically acceptable salts thereof, wherein ##STR2## with the proviso that the 3a and 6a hydrogens are cis and where there is a 4-position hydroxy then such is trans to the 3a and 6a hydrogens, andwith the proviso that R.sup.b is not hydrogen when the 4-position aryl is cis to the 3a and 6a hydrogens and there is no hydroxy at the 4-position.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: July 30, 1996
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Richard J. Carmosin, John R. Carson, Philip M. Pitis
  • Patent number: 5508433
    Abstract: This invention relates to derivatives of perhydroisoindol of formula: ##STR1## in which the radicals R are hydrogen atoms or together form a bond, the symbols R.sub.2 are phenyl radicals which can be substituted by a halogen atom or a methyl radical in position 2 or 3, R.sub.3 is a halogen atom or a hydroxy radical, R.sub.4 is H or halogen if R.sub.3 is halogen, in their isomer forms, or mixture thereof, and possibly also their salts when they exist, and preparation thereof. The derivatives of the invention are particularly interesting as P substance antagonist.
    Type: Grant
    Filed: November 17, 1993
    Date of Patent: April 16, 1996
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Daniel Achard, Serge Grisoni, Stephen Hanessian, Claude Moutonnier, Jean-Francois Peyronel, Michel Tabart, Alain Truchon
  • Patent number: 5486620
    Abstract: This invention provides a process for preparing kainic acid and provides intermediates in the synthesis thereof.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: January 23, 1996
    Assignee: Eli Lilly and Company
    Inventor: James A. Monn
  • Patent number: 5473080
    Abstract: Novel 3-azabicyclo[3.2.0]heptane derivatives of the formula ##STR1## in which R.sup.1 and R.sup.2 have the meanings stated in the description, and their preparation are described. The substances are intermediates for the preparation of drugs.
    Type: Grant
    Filed: December 12, 1994
    Date of Patent: December 5, 1995
    Assignee: BASF Aktiengesellschaft
    Inventor: Gerd Steiner
  • Patent number: 5468742
    Abstract: The invention relates to new 8-vinyl- and 8-ethinylquinolonecarboxylic acids, process for their preparation, and antibacterial agents and feed additives containing them.
    Type: Grant
    Filed: November 1, 1993
    Date of Patent: November 21, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Thomas Himmler, Thomas Schenke, Andreas Krebs, Klaus Grohe, Klaus-Dieter Bremm, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 5463077
    Abstract: This ivention relates to novel perhydroisoindole derivatives having formula (I), ##STR1## wherein the symbols R, which are the same or different, are phenyl radicals optionally 2- or 3-substituted by a halogen atom or a methyl radical, R' is a phenyl radical optionally 2-substituted by a C.sub.1-2 alkylk or alkyloxy radical, R" is a fluorine atom or a hydroxy radical, and R'" is a hydrogen atom, or else R' and R'" are hydroxy radicals, or R" and R'" together form a bond, and R.sup.o is a hydrogen atom or a protective radical; salts thereof whereever applicable; and preparation thereof. These products are synthetic intermediates for the preparation of derivatives having P substance antagonist activity.
    Type: Grant
    Filed: October 11, 1994
    Date of Patent: October 31, 1995
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Daniel Achard, Serge Grisoni, Jean-Luc Malleron, Jean-Francois Peyronel, Michel Tabart
  • Patent number: 5451601
    Abstract: This invention relates to derivatives of perhydroisoindol of formula: ##STR1## in which the radicals R are hydrogen atoms or together form a bond, the symbols R' are phenyl radicals which can be substituted by a halogen atom or a methyl radical in position 2 or 3, X is an oxygen atom or an NH radical, R.sub.1 is optionally substituted phenyl, or cyclohexadienyl, naphthyl, or heterocyclyl, R.sub.2 is H, halogen, OH, alkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkyloxy, alkylthio, acyloxy, carboxy, optionally substituted alkyloxycarbonyl, benzyloxycarbonyl, amino or acylamino, R.sub.3 is halogen or OH and R.sub.4 is H or halogen if R.sub.3 is halogen, in their isomer forms, or mixture thereof, and possibly also their salts when they exist, and preparation thereof. The derivatives of the invention are particularly interesting as P substance antagonist.
    Type: Grant
    Filed: November 17, 1993
    Date of Patent: September 19, 1995
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Daniel Achard, Serge Grisoni, Stephen Hanessian, Claude Moutonnier, Jean-Francois Peyronel, Michel Tabart, Alain Truchon
  • Patent number: 5409929
    Abstract: There are provided novel nitrogen-containing bicyclic compounds which are useful in the treatment of physiological or drug induced psychosis or dyskinesia in a mammal. These novel compounds are selective sigma receptor antagonists and have a low potential for movement disorder side effects associated with typical antipsychotic agents.
    Type: Grant
    Filed: February 17, 1993
    Date of Patent: April 25, 1995
    Assignee: The DuPont Merck Pharmaceutical Company
    Inventor: Engelbert Ciganek
  • Patent number: 5391763
    Abstract: Quinolone carboxylic acids 7 -substituted by azabicyclo groups have antibacterial activity.
    Type: Grant
    Filed: August 26, 1993
    Date of Patent: February 21, 1995
    Assignee: Pfizer Inc.
    Inventor: Katherine E. Brighty
  • Patent number: 5352799
    Abstract: The present invention provides processes for the synthesis of kainic acid. More specifically, the present invention is directed to a process for preparing a compound of the formula ##STR1## wherein R.sub.1 is hydrogen, acyl, alkoxycarbonyl, or arylalkoxycarbonyl;R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, or arylalkyl; andR.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, or arylalkyl.The present invention also provides processes for the preparation of intermediates that are useful for the synthesis of kainic acid. More specifically, the present invention provides processes for preparing a compound of the formula ##STR2## wherein R.sub.4 is hydrogen, acyl , alkoxycarbonyl, or arylalkoxycarbonyl; andR.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, or arylalkyl.
    Type: Grant
    Filed: April 30, 1993
    Date of Patent: October 4, 1994
    Assignee: Eli Lilly and Company
    Inventor: James A. Monn
  • Patent number: 5319095
    Abstract: This invention provides a process for preparing kainic acid and provides intermediates in the synthesis thereof.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: June 7, 1994
    Assignee: Eli Lilly and Company
    Inventor: James A. Monn
  • Patent number: 5310911
    Abstract: A process for preparing substantially pure enantiomers of formula (I) ##STR1## where the * represents a chiral center, x is 0 or 1, in exo-, endo- or a mixture of exo- and endo- forms; and R is hydrogen, alkyl or aralkyl, via diastereomers of formula (IIA) or (IIB): ##STR2##
    Type: Grant
    Filed: March 11, 1992
    Date of Patent: May 10, 1994
    Inventors: I. F. Cottrell, S. H. B. Wright, D. Hands
  • Patent number: 5202335
    Abstract: Succinic acid compounds of the formula: ##STR1## wherein A represents a heterocyclic group, a 3 to 8-membered cycloalkyl group or a phenyl group which may have one or more substituents selected from the group of a halogen atom, a lower alkyl group having 1 to 6 carbon atoms and a lower alkoxy group having 1 to 6 carbon atoms; B represents a bicyclic amino group which may have 1 or 2 unsaturated bonds, with the proviso that B bonds to the carbon atom of the carbonyl group at the nitrogen atom; R represents a hydrogen atom or combines each other to form a chemical bond; R.sup.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: April 13, 1993
    Assignee: Kissei Pharmaceutical Co., Ltd.
    Inventors: Fumiyasu Sato, Atsushi Tsubaki, Hiroshi Hokari, Nobuyuki Tanaka, Masaru Saito, Kenji Akahane, Michihiro Kobayashi
  • Patent number: 5187290
    Abstract: Compounds of the formula ##STR1## wherein Z is oxygen or sulfur are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inbitition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: February 16, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Eric M. Gordon
  • Patent number: 5149825
    Abstract: The present invention describes a novel compound, 2-azabicyclo[2.2.1]hept-5-ene-2-acetic acid, its preparation and the preparation of related compounds, and the use of said compounds as intermediates for the preparation of N-phosphonomethylglycine.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: September 22, 1992
    Assignee: American Cyanamid Company
    Inventor: David A. Cortes
  • Patent number: 5118849
    Abstract: Intermediates of the formula ##STR1## are new, whereR stands for alkyl, alkenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl, in each case having up to 20 carbon atoms, in each case optionally branched and in each case interrupted by 1 to 4 oxygen atoms, andX stands for hydrogen or halogen, and are useful for synthesizing herbicidal and plant growth regulating compounds.
    Type: Grant
    Filed: April 16, 1991
    Date of Patent: June 2, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Schallner, Reiner Fischer, Albrecht Marhold, Karl-Julius Reubke, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen, Harry Strang
  • Patent number: 5101039
    Abstract: Disclosed are cis, exo- and trans-compounds of the formula I ##STR1## in which n denotes 0, 1 or 2, R.sub.1 denotes hydrogen (C.sub.1 -C.sub.6)-alkyl which can optionally be substituted by amino, (C.sub.1 -C.sub.4)-acyl- or bezoylamino, (C.sub.2 -C.sub.6)-alkenyl, (C.sub.5 -C.sub.9)-cycloalkyl, (C.sub.5 C.sub.9)-cycloalkenyl, (C.sub.5 -C.sub.7)-cycloalkyl-(C.sub.1 -C.sub.4)-alkyl, aryl or partially hydrogenated aryl, which can, in each case, be substituted by (C.sub.1 C.sub.2)-alkyl, (C.sub.1 -C.sub.2)-alkoxy or halogen, aryl-(C.sub.1 -C.sub.4)-alkyl, [which can be substituted as defined previously in the aryl radical], a monocyclic or bicyclic sulfur or nitrogen and/or nitrogen heterocyclic radical, or a side chain of naturally occurring aminoacid, R.sub.2 denotes hydrogen, (C.sub.1 -C.sub.6)-alkyl, (C.sub.2 -C.sub.6)-alkenyl or aryl-(C.sub.1 -C.sub.4)-alkyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen, X denotes (C.sub.1 -C.sub.6)-alkyl, (C.sub.2 -C.sub.
    Type: Grant
    Filed: January 23, 1990
    Date of Patent: March 31, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hansjorg Urbach, Rainer Henning, Volker Teetz, Rolf Geiger, Reinhard Becker, Holger Gaul
  • Patent number: 5098910
    Abstract: The invention relates to combinations of angiotensin-converting enzyme inhibitors with calcium antagonists, processes for their preparation and their use as medicaments.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: March 24, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Reinhard Becker, Rainer Henning, Wolfgang Ruger, Volker Teetz, Hansjorg Urbach
  • Patent number: 5047400
    Abstract: The invention relates to the compounds of general formula: ##STR1## in which: X denotes either an oxygen atom, or two hydrogen atoms;Y denotes either a hydrogen atom, or a hydroxyl group;or Y denotes an amino group on condition that X denotes two hydrogen atoms;R denotes a hydrogen atom, or a straight- or branched-chain alkyl group having 1 to 6 carbon atoms, optionally substituted with one or more hydroxy, amino, mercapto, methylthio or carboxy groups, or aryl groups such as phenyl, pyridyl or thienyl; ##STR2## denotes a polycyclic nitrogenous structure; their enantiomers, epimers and diastereoisomers, as well as their addition salts with a pharmaceutically acceptable acid or base.
    Type: Grant
    Filed: June 16, 1988
    Date of Patent: September 10, 1991
    Assignee: Adir et Cie
    Inventors: Michel Vincent, Georges Remond, Bernard Portevin, Claude Cudennec
  • Patent number: 5039334
    Abstract: Herbicidal and plant growth-regulating substituted N-aryl nitrogen heterocycles of the formula ##STR1## in which Het stands for ##STR2## where A stands for ##STR3## where R.sup.1 and R.sup.2 in each case independently of one another stand for hydrogen, halogen, halogenoalkyl or alkyl,Y.sup.1 and Y.sup.2 in each case stand for oxygen or sulphur andZ stands for hydrogen, hydroxyl or chlorine,R stands for alkyl, alkenyl, cycloalkyl, cycloalkenyl, cycloalylalkyl, or cycloalkenylalkyl, in each case optionally branched and in each case interrupted by at least one oxygen atom, andX stands for hydrogen or halogen.Intermediates of the formula ##STR4## are also new.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: August 13, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Schallner, Reiner Fischer, Albrecht Marhold, Karl-Julius Reubke, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen, Harry Strang
  • Patent number: 5017708
    Abstract: 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: Grant
    Filed: September 8, 1989
    Date of Patent: May 21, 1991
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masaru Ogata, Hiroshi Matsumoto, Sumio Shimizu, Shiro Kida
  • Patent number: 5008400
    Abstract: Disclosed are cis, exo- and trans-compounds of the formula I ##STR1## in which n denotes 0,1 or 2, R.sub.1 denotes hydrogen, (C.sub.1 -C.sub.6)-alkyl which can optionally by substituted by amino, (C.sub.1 -C.sub.4)-acyl- or bezoylamino, (C.sub.2 -C.sub.6)-alkenyl, (C.sub.5 -C.sub.9)-cycloalkyl, (C.sub.5 -C.sub.9)-cycloalkenyl, (C.sub.5 -C.sub.7)-cycloalkyl-(C.sub.1 -C.sub.4)-alkyl, aryl or partially hydrogenated aryl, which can, in each case, be substituted by (C.sub.1 -C.sub.2)-alkyl, (C.sub.2 -C.sub.2)-alkoxy or halogen, aryl-(C.sub.1 -C.sub.4)-alkyl, /which can be substituted as defined previously in the aryl radical/, a monocyclic or bicyclic sulfur or nitrogen and/or nitrogen heterocyclic radical, or a side chain of naturally occurring aminoacid, R.sub.2 denotes hydrogen, (C.sub.1 -C.sub.6)-alkyl, (C.sub.2 -C.sub.6)-alkenyl or aryl-(C.sub.1 -C.sub.4)-alkyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen, X denotes (C.sub.1 -C.sub.6)-alkyl, (C.sub.2 -C.sub.
    Type: Grant
    Filed: November 21, 1984
    Date of Patent: April 16, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hansjorg Urbach, Rainer Henning, Volker Teetz, Rolf Geiger, Reinhard Becker, Holger Gaul
  • Patent number: 4990668
    Abstract: Described is a process for preparing a racemic or chiral aryloxypropanolamine (1) or arylethanolamine (2) of the formula ##STR1## wherein Ar is aryl, substituted aryl, heteroaryl, or aralkyl and R is alkyl, substituted alkyl, aralkyl, or WB wherein W is a straight or branched chain alkylene of from 1 to about 6 carbon atoms and wherein B is --NR.sub.2 COR.sub.3, --NR.sub.2 CONR.sub.3 R.sub.4, --NR.sub.2 SO.sub.2 R.sub.3, --NR.sub.2 SO.sub.2 NR.sub.3 R.sub.4, or --NR.sub.2 COOR.sub.5, where R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, alkoxyaryl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.3 and R.sub.5 are not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.3 or --NR.sub.3 COOR.sub.5, or R.sub.3 and R.sub.4 may together with N form a 5- to 7-membered heterocyclic group.The process can be used to prepare beta-blocking agents, useful in the treatment of cardiac conditions.
    Type: Grant
    Filed: December 4, 1985
    Date of Patent: February 5, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Khuong H. X. Mai, Ghanshyam Patil, William L. Matier
  • Patent number: 4968341
    Abstract: 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: Grant
    Filed: August 16, 1988
    Date of Patent: November 6, 1990
    Assignees: 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
  • Patent number: 4853149
    Abstract: Heterocyclic liquid crystal compounds containing the structural element ##STR1## wherein M is H, CN,, NCS, halogen or an alkyl group with 1-5 C atoms,X is CR.sup.4 or N,Y is CHR.sup.4, O, S or NR.sup.5,R.sup.4 is H, alkyl with 1-15 C atoms, halogen or cyano andR.sup.5 is H or alkyl with 1-15 C atoms,with the proviso that in the case where Y=CHR.sup.4, X is N, are suitable as components of liquid crystal phases.
    Type: Grant
    Filed: October 26, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Joachim Krause, Andreas Wachtler, Bernhard Scheuble, Georg Weber
  • Patent number: 4735959
    Abstract: There are described novel carboxylic acid derivatives of the formula ##STR1## and derivatives of the formula ##STR2## and the addition salts thereof, which exhibit an effect on the intermediary metabolism. Furthermore, the compounds of Formula Ia as well as the compounds of Formula I possess blood-sugar lowering properties.
    Type: Grant
    Filed: May 14, 1985
    Date of Patent: April 5, 1988
    Assignee: Dr. Karl Thomae GmbH
    Inventors: Wolfgang Grell, Gerhart Griss, Robert Sauter, Rudolf Hurnaus, Eckhard Rupprecht, Nikolaus Kaubisch, Joachim Kahling, Bernhard Eisele
  • Patent number: 4713459
    Abstract: A novel compound of the formula, ##STR1## wherein R denotes a lower perfluoroalkyl group, l is an integer of 3 or 4, n+m is an integer of 2 or 3, provided that n may be zero, and at least one of ring A and ring B may be substituted by a lower perfluoroalkyl group, prepared by reacting the corresponding perhydro compound with fluorine is useful as a material capable of carrying oxygen in an aqueous emulsion for lifesaving a patient suffering from massive hemorrhage and for preserving internal organs in transplantation.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: December 15, 1987
    Assignee: The Green Cross Corporation
    Inventors: Kazumasa Yokoyama, Chikara Fukaya, Yoshio Tsuda, Taizo Ono, Yoshio Arakawa, Tadakazu Suyama
  • Patent number: 4691022
    Abstract: The invention relates to a process for the preparation of compounds of the formula I ##STR1## in which R represents hydrogen, alkyl or aralkyl, and R.sup.1 to R.sup.6 denote identical or different radicals hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenylalkyl, aralkyl or aryl, both being monosubstituted, disubstituted or trisubstituted in the aryl moiety by alkyl, alkoxy, hydroxyl, halogen, nitro, methylenedioxy and/or cyano, or in which two of the radicals R.sup.1 to R.sup.6, together with the carbon atom(s) bearing them form a monocyclic or bicyclic ring system, and the remaining radicals are hydrogen, which process comprises converting, with an oxidizing agent in the presence of a silver salt, a pyrrolidine derivative of the formula II into a .DELTA..sup.1 -pyrroline derivative of the formula III, reacting the latter with hydrogen cyanide or a metal cyanide to form a nitrile of the formula IV, and subjecting the latter to solvolysis with a compound of the formula ROH.
    Type: Grant
    Filed: June 21, 1984
    Date of Patent: September 1, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rainer Henning, Hansjorg Urbach
  • Patent number: 4659838
    Abstract: The invention relates to a process for resolving racemic mixtures of bicyclic imino-.alpha.-carboxylic acid esters into the components of the formula Ia and Ib ##STR1## in which R.sup.1 stands for an aliphatic, cycloaliphatic, aromatic or araliphatic radical,A denotes hydrogen and B and C together form a carbon chain or C denotes hydrogen and A and B together form a carbon chain, by crystallizing diastereoisomeric salts, which comprises preparing the salts of the racemic esters with optically active O,O-diacyltartaric acids in a suitable solvent in which only one of the two diastereoisomeric salts crystallizes in optically pure form, if desired purifying the diastereoisomeric salt by recrystallization, reprecipitation or trituration, and finally adding basec to the salt to cleave it into the pure enantiomer of the formula Ia or Ib.The invention also relates to diastereoisomeric salts of an ester of the formula Ia or Ib and a diacyltartaric acid.
    Type: Grant
    Filed: December 13, 1984
    Date of Patent: April 21, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Ulrich Lerch
  • Patent number: 4647576
    Abstract: 6-[2-(Substituted-pyrrol-1-yl)alkyl]pyran-2-ones and the corresponding ring-opened hydroxy-acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutarylcoenzyme A reductase (HMG-CoA reductase), and are thus useful hypolipidemic and hypocholesterolemic agents. Pharmaceutical compositions containing such compounds, and a method of treatment employing such pharmaceutical compositions are also disclosed.
    Type: Grant
    Filed: December 10, 1984
    Date of Patent: March 3, 1987
    Assignee: Warner-Lambert Company
    Inventors: Milton L. Hoefle, Bruce D. Roth, Charlotte D. Stratton
  • Patent number: 4632935
    Abstract: OMEGA-(Hydroxy, ether and ester) alkyl-2-Amino-Cycloalkenyl and -cycloalkyl amide compounds of the formula: ##STR1## where the wavy line bonds, m, n, p, A, R, R.sub.1, R.sub.2, X, Y and Z are as defined in the specification, e.g., 3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)-3-(3-acetyloxypropyl)cyclohexe nyl]benzamide, and pharmacologically acceptable salts thereof, are useful as analgesic drug compounds having low physical dependence liability, compared to morphine and methadone. Pharmaceutical compositions and methods for using these compounds and compositions as analgesics are disclosed. Processes for preparing this class of compounds are also disclosed.
    Type: Grant
    Filed: May 30, 1984
    Date of Patent: December 30, 1986
    Assignee: The Upjohn Company
    Inventor: Lester J. Kaplan
  • Patent number: 4599420
    Abstract: This invention relates to novel substituted benzamides having useful pharmacological properties, to pharmaceutical compositions containing them, to a process for their preparation and to intermediates therefor.N-(2-Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide, 1-ethyl-2(2-methoxy-5-sulphamoylbenzamidomethyl)pyrrolidine and N-[4'-(1"-benzyl)-piperidyl]-2-methoxy-4-amino-5-chlorobenzamide are well known compounds having useful pharmacological activity such as the ability to regulate the gastro-intestinal function anti-emetic activity and CNS activity.It has now been found that certain intermediates for a structurally distinct class of substituted benzamides also has useful pharmacological activity, in particular dopamine antagonist activity.
    Type: Grant
    Filed: February 25, 1983
    Date of Patent: July 8, 1986
    Assignee: Beecham Group Ltd.
    Inventors: Michael S. Hadley, Francis D. King
  • Patent number: 4591593
    Abstract: A novel compound of the formula, ##STR1## wherein R denotes a lower perfluoroalkyl group l is an integer of 3 or 4, n+m is an integer of 2 or 3, provided that n may be zero, and at least one of ring A and ring B may be substituted by a lower perfluoroalkyl group, prepared by reacting the corresponding perhydro compound with fluorine is useful as a material capable of carrying oxygen in an aqueous emulsion for lifesaving a patient suffering from massive hemorrhage and for preserving internal organs in transplantation.
    Type: Grant
    Filed: November 17, 1982
    Date of Patent: May 27, 1986
    Assignee: The Green Cross Corporation
    Inventors: Kazumasa Yokoyama, Chikara Fukaya, Yoshio Isuda, Taizo Ono, Yoshio Arakawa, Tadakazu Suyama
  • Patent number: 4560767
    Abstract: Amino-cycloalkenyl-amide compounds, e.g., (1.alpha.,6.beta.)-(.+-.)-3,4-dichloro-N-methyl-N-(6-(1-pyrrolidinyl)-3-cy clohexen-1-yl)benzeneacetamide, and tritiated derivatives thereof, are useful as analgesics and as radio labeled compounds for pharmacological and metabolism studies in animals.
    Type: Grant
    Filed: June 17, 1983
    Date of Patent: December 24, 1985
    Assignee: The Upjohn Company
    Inventors: John M. McCall, Robert A. Lahti
  • Patent number: 4546110
    Abstract: Compounds which are .beta.-farnesene derivatives obtainable as a Diels-Adler adduct of .beta.-farnesene and a dienophile or by a modification of such an adduct in a manner as defined herein are of value in pest control, particularly in the control of aphids.
    Type: Grant
    Filed: January 20, 1983
    Date of Patent: October 8, 1985
    Assignee: National Research Development Corporation
    Inventors: Glenn W. Dawson, David C. Griffiths, John A. Pickett
  • Patent number: 4544665
    Abstract: This invention concerns 1-aryl-3-azabicyclo[3.2.0]heptanes and their acid-addition salts. More particularly, this invention pertains to compositions useful for treatment of depression in warm-blooded animals.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: October 1, 1985
    Assignee: American Cyanamid Company
    Inventors: Joseph W. Epstein, Thomas C. McKenzie, William J. Fanshawe
  • Patent number: 4529597
    Abstract: 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: Grant
    Filed: April 19, 1982
    Date of Patent: July 16, 1985
    Assignee: Merck & Co., Inc.
    Inventor: James V. Heck
  • Patent number: 4503043
    Abstract: Substituted acyl derivatives of octahydro-1H-isoindole-1-carboxylic acid compounds and the pharmaceutically acceptable salts thereof are produced by acylating a suitably substituted octahydro-1H-isoindole with a suitably activated substituted carboxylic acid and when desired hydrolyzing the resulting product. The compounds of the invention, their salts and pharmaceutical compositions thereof are useful as antihypertensive agents.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: March 5, 1985
    Assignee: Warner-Lambert Company
    Inventor: Clifton J. Blankley
  • Patent number: 4499079
    Abstract: Peptides of the formula ##STR1## wherein X is various amino or imino acids or esters are useful as hypotensive agents.
    Type: Grant
    Filed: November 18, 1982
    Date of Patent: February 12, 1985
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Eric M. Gordon, Harold N. Weller, III
  • Patent number: 4428960
    Abstract: Disclosed are 3-amido-6-substituted thio-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 NH.sub.2, R.sup.1 NH, R.sup.1 is acyl; and 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: Grant
    Filed: April 19, 1982
    Date of Patent: January 31, 1984
    Assignee: Merck & Co., Inc.
    Inventor: James V. Heck