Polycyclo Ring System Having One Of The Two Rings Which Form The Spiro As One Of The Cyclos Patents (Class 546/17)
  • Patent number: 5670509
    Abstract: Compounds of the formula X-Y-Z-R.sup.1 wherein:X is ##STR1## Y is --CO-- or --SO.sub.2 --; Z is an optional substituent selected from --NH--, --O--, --CHR--, --CH.dbd.CH--, --CH.dbd., --(CH.sub.2).sub.m -- or--CHCHOH--; andR.sup.1 is --CH.sub.3 --, --CH(CH.sub.3).sub.2, or substituted phenyl are tocolytic oxytocin antagonists useful in the treatment of pre-term labor, stripping labor preparatory to Caesarean delivery and dysmenorrhea.
    Type: Grant
    Filed: April 5, 1995
    Date of Patent: September 23, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Ben E. Evans, Douglas W. Hobbs, Joseph M. Pawluczyk, Douglas J. Pettibone, Kenneth E. Rittle, Peter D. Williams
  • Patent number: 5665725
    Abstract: Piperidine compounds having the general formula (I), ##STR1## wherein R.sup.1 is a group having general formula (II), ##STR2## wherein X is CHR.sup.10, O, S, SO, SO.sub.2 or NR.sup.10, Z.sup.1 is CH.sub.2, O, or S; Z.sup.2 and Z.sup.3 are independently (CH.sub.2).sub.n, n being 0 or 1, O or S or Z.sup.1 and Z.sup.2 may together represent a group --CH.dbd.CH--; or when Z.sup.3 is (CH.sub.2).sub.n wherein n is 0, Z.sup.1 and Z.sup.2 may together represent a 3-membered divalent group; show potent sigma receptor activity. Furthermore they show effect in animal models indicative of anxiolytic properties. Accordingly they are useful as medicines for the treatment of anxiety, psychosis, epilepsy, convulsion, movement disorders, motor disturbances, amnesia, cerebrovascular diseases, senile demential of the Alzheimer type or Parkinson's disease.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: September 9, 1997
    Assignee: H. Lundbeck
    Inventors: Ejner K. Moltzen, Jens Kristian Perregaard
  • Patent number: 5658921
    Abstract: The subject invention describes Novel dimer 4-phenylpiperidine, 4-phenyl-1,2,3,6-tetrahydropyridine, or 4-phenylpiperazine compounds or dimeric spirocyclic piperidine compounds having the general Formula I: ##STR1## wherein n is 1-5;R.sup.1 to R.sup.4 are independently selected from hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulfonyl, C.sub.1-6 alkyl- or di-(C.sub.1-6 alkyl)amino, cyano, trifluoromethyl, nitro, trifluoromethylthio or trifluoromethylsulfonyloxy; R.sup.5 and R.sup.6 are independently hydrogen, or C.sub.1-6 alkyl;X is O, S, SO, SO.sub.2, CO or (CH.sub.2).sub.m, m being 0 or 1, or X is NR.sup.7, R.sup.7 being H, C.sub.1-6 alkyl, cycloalkyl, cycloalkylalkyl, phenyl, or phenylalkyl, or X is CR.sup.8 R.sup.9, wherein R.sup.8 and R.sup.9 are independently selected from the group consisting of hydroxy and the substituents defined under R.sup.7, any phenyl group being optionally substituted with one or more substituents selected from halogen, C.
    Type: Grant
    Filed: December 12, 1994
    Date of Patent: August 19, 1997
    Assignee: H. Lundbeck A/S
    Inventors: Jens Perregaard, John W. Stenberg, Ejner K. Moltzen
  • Patent number: 5656606
    Abstract: The present invention is directed to certain novel compounds identified as camphor derivatives of the general structural formula: ##STR1## wherein A, X, Y, R.sup.2a, R.sup.4, and R.sup.5 are as defined herein. These compounds promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, such as short stature in growth hormone deficient children, and to treat medical conditions which are improved by the anabolic effects of growth hormone. Growth hormone releasing compositions containing such compounds as the active ingredient thereof are also disclosed.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: August 12, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Ravi Nargund, Arthur A. Patchett
  • Patent number: 5654296
    Abstract: The compound ##STR1## wherein ring A represents a benzene ring;Ar represents an aromatic group;R.sup.1 and R.sup.2 independently represent hydrogen, acyl or hydrocarbon group or R.sup.1 and R.sup.2 taken together with the adjacent nitrogen atom represent a nitrogen-containing heterocyclic group;m represents an integer of 1 to 6;n represents an integer of 2 to 3;- - - - - represents a single bond or a double bond;X stands for --O-- or --NR.sup.3 -- in which R.sup.3 represents hydrogen, acyl or hydrocarbon group where - - - - - is a single bond or .dbd.N-- where - - - - - is a double bond has excellent GnRH receptor antagonizing activity, calcium antagonizing and monoamine-uptake inhibiting activities and and value as a prophylactic/therapeutic drug for sex hormone-dependent diseases and for central nervous system diseases.
    Type: Grant
    Filed: December 6, 1996
    Date of Patent: August 5, 1997
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kaneyoshi Kato, Yoshihiro Sugiura, Koichi Kato, Yasuo Nagai
  • Patent number: 5654299
    Abstract: The present invention concerns the novel use of aryl substituted heterocycles of formula I, set out below, which antagonize the pharmacological actions of one of ent endogenous neuropeptide tachykinins an the neurokinin 2 (NK2) receptor making them useful whenever such antagonism is desired, such as in the treatment of asthma and related conditions. The invention also provides pharmaceutical compositions containing the aryl substituted heterocycles for use in such treatment. Certain novel aryl substituted heterocycles of formula I and novel intermediates for their manufacture are also provided.
    Type: Grant
    Filed: April 18, 1994
    Date of Patent: August 5, 1997
    Assignee: Zeneca Limited
    Inventors: Ashokkumar Bhikkappa Shenvi, Robert Toms Jacobs
  • Patent number: 5633247
    Abstract: Spirocycles of general structural formula: ##STR1## are Class III antiarrhythmic agents.
    Type: Grant
    Filed: July 5, 1995
    Date of Patent: May 27, 1997
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, David A. Claremon, Jason M. Elliott, Gerald S. Ponticello, David C. Remy, Harold G. Selnick
  • Patent number: 5633248
    Abstract: A compound of the formula: ##STR1## wherein Ar.sup.1 and Ar.sup.2 independently represent an optionally substituted aromatic group; P and Q independently represent a divalent aliphatic hydrocarbon group having at least 2 carbon atoms and optionally having either oxygen or sulfur in the carbon chain; R.sup.1 and R.sup.3 independently represent --CO--R, --CONH--R (R represents a hydrocarbon group or a heterocyclic group) or a hydrocarbon group; R.sup.2 and R.sup.4 independently represent hydrogen or an alkyl group; R.sup.2 and R.sup.4 independently represent hydrogen or an alkyl group; R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4, taken together with the adjacent nitrogen atom, may form a nitrogen-containing heterocyclic group; and j represents 0 or 1, or a salt thereof, has excellent GnRH-receptor antagonizing activity and is useful as a prophylactic and therapeutic agent for hormone-dependent and other diseases.
    Type: Grant
    Filed: November 21, 1995
    Date of Patent: May 27, 1997
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kaneyoshi Kato, Yoshihiro Sugiura, Koichi Kato
  • Patent number: 5618833
    Abstract: The present invention relates to 1-benzyl-1,3-dihydroindol-2-one derivatives of the formula (I). The invention also relates to preparation of these derivatives as well as to the pharmaceutical compositions in which they are present. These derivatives have an affinity for the vasopressin and oxytocin receptors.
    Type: Grant
    Filed: July 29, 1994
    Date of Patent: April 8, 1997
    Assignee: Sanofi
    Inventors: Lo ic Foulon, Georges Garcia, Daniel Mettefeu, Claudine Serradeil-Legal, G erard Valette
  • Patent number: 5607939
    Abstract: The compound ##STR1## wherein ring A represents a benzene ring; Ar represents an aromatic group; R.sup.1 and R.sup.2 independently represent hydrogen, acyl or hydrocarbon group or R.sup.1 and R.sup.2 taken together with the adjacent nitrogen atom represent a nitrogen-containing heterocyclic group; m represents an integer of 1 to 6; n represents an integer of 2 to 3; ----- represents a single bond or a double bond; X stands for --O-- or --NR.sup.3 -- in which R.sup.3 represents hydrogen, acyl or hydrocarbon group where ----- is a single bond or .dbd.N-- where ----- is a double bond has excellent GnRH receptor antagonizing activity, calcium antagonizing and monoamine-uptake inhibiting activities and and value as a prophylactic/therapeutic drug for sex hormone-dependent diseases and for central nervous system diseases.
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: March 4, 1997
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kaneyoshi Kato, Yoshihiro Sugiura, Koichi Kato, Yasuo Nagai
  • Patent number: 5591849
    Abstract: A spiro compound represented by the formula: ##STR1## wherein ring A represents an optionally substituted aromatic ring; T represents an optionally substituted hydrogen atom or an optionally substituted hydrocarbon group; X represents --CH.sub.2 --, --CO-- or --CH(OH)--; D represents --CH.sub.2 --, --O-- or --NR-- wherein R is a hydrogen atom or an optionally substituted hydrocarbon group and m, e and f independently represent an integer from 1 to 3, or a salt thereof. The spiro compound inhibits monoamine uptake, monoamine oxidase B and/or Ca ion uptake, and is a prophylactic and therapeutic drug for a central nervous diseases.
    Type: Grant
    Filed: March 3, 1995
    Date of Patent: January 7, 1997
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kaneyoshi Kato, Jun Terauchi, Yasuo Nagai
  • Patent number: 5578593
    Abstract: There are disclosed certain novel compounds identified as spiro piperidines and homologs which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, such as short stature in growth hormone deficient children, and to treat medical conditions which are improved by the anabolic effects of growth hormone. Growth hormone releasing compositions containing such spiro compounds as the active ingredient thereof are also disclosed.
    Type: Grant
    Filed: November 3, 1993
    Date of Patent: November 26, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Meng-Hsin Chen, David B. R. Johnston, Ravi P. Nargund, Arthur A. Patchett, James R. Tata, Lihu Yang
  • Patent number: 5567624
    Abstract: A composition for determining pH of a solution comprises a fluorescent carbazine dye covalently bound to a solid support. A method of determining pH of a solution comprises placing the composition in the solution, contacting the composition with a selected wavelength of light to excite fluorescence by the carbazine dye, measuring intensities of the fluorescence at two selected wavelengths, calculating a ratio of fluorescence intensities at the two selected wavelengths, and correlating the ratio with a predetermined relationship of such ratios to pH. A fiber optic system for measuring pH of a solution with the carbazine-dye-containing composition is also disclosed.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: October 22, 1996
    Assignee: Utah Medical Products, Inc.
    Inventor: Roger E. Smith
  • Patent number: 5554752
    Abstract: 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: Grant
    Filed: March 14, 1995
    Date of Patent: September 10, 1996
    Assignee: Regents of the University of Minnesota
    Inventors: Simon M. N. Efange, Stanley M. Parsons
  • Patent number: 5554621
    Abstract: A series of non-peptidergic antagonists of NPY have been synthesized and are comprised of nitrogen heterocyclic derivatives of 4-phenyl-1,4-dihydropyridines of Formula (I). ##STR1## As antagonists of NPY-induced feeding behavior, these compounds are expected to act as effective anorexiant agents in promoting weight loss and treating eating disorders.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 10, 1996
    Assignee: Bristol-Myers Squibb Company
    Inventors: Graham S. Poindexter, Marc Bruce, Graham Johnson, Karen LeBoulluec, Jeffrey W. Noonan
  • Patent number: 5536716
    Abstract: There are disclosed certain novel compounds identified as spiro piperidines and homologs which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, such as short stature in growth hormone deficient children, and to treat medical conditions which are improved by the anabolic effects of growth hormone. Growth hormone releasing compositions containing such spiro compounds as the active ingredient thereof are also disclosed.
    Type: Grant
    Filed: November 3, 1993
    Date of Patent: July 16, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Meng-Hsin Chen, David B. R. Johnston, Ravi P. Nargund, Arthur A. Patchett, James R. Tata, Lihu Yang
  • Patent number: 5532372
    Abstract: An imide compound of the formula: ##STR1## wherein Z is a group of the formula: ##STR2## in which the substituents are defined herein, and n is an integer of 0 to 1;D is a group of the formula:--(CH.sub.2).sub.p --A--(CH.sub.2).sub.q --in which A is a non-aromatic hydrocarbon ring optionally bridged with a lower alkylene group or an oxygen atom, said non-aromatic hydrocarbon ring and said lower alkylene group being each optionally substituted with at least one lower alkyl, and p and q are each an integer of 0, 1 or 2; andAr is an aromatic group, a heterocyclic aromatic group, a benzoyl group, a phenoxy group or a phenylthio group and G is >N--, >CH-- or >COH-- or Ar is a biphenylmethylidene group and G is >C.dbd., all of the above groups being each optionally substituted with at least one of lower alkyl, lower alkoxy and halogen; and its acid addition salts, useful as an antipsycotic agent.
    Type: Grant
    Filed: August 30, 1993
    Date of Patent: July 2, 1996
    Assignee: Sumitomo Pharmaceuticals Company, Ltd.
    Inventors: Ikutaro Saji, Masayuki Muto, Norihiko Tanno, Mayumi Yoshigi
  • Patent number: 5493029
    Abstract: The present invention relates to novel benzopyran derivatives of formula (I) which have exellent effectiveness in the treatment of asthma as well as hypertension. ##STR1## wherein: R.sub.1 is --CN, --NO.sub.2, --OCX.sub.1 X.sub.2 X.sub.3, --NH.sub.2, --NHSO.sub.2 R.sup.A, ##STR2## --SO.sub.2 R.sup.C or --SO.sub.2 NR.sup.C R.sup.D wherein X.sub.1, X.sub.2 and X.sub.3 are, each independently, F, Cl or H, except for that X.sub.1, X.sub.2 and X.sub.3 may not be hydrogen atom simulaneously; R.sup.A and R.sup.B are, each independently, a hydrogen atom, or a C.sub.1-6 alkyl group or an optionally substituted phenyl group with a halogen atom, or a straight or branched C.sub.1-3 alkyl group; and R.sup.C and R.sup.D are, each independently, a hydrogen atom or a C.sub.1-6 alkyl group or an optionally substituted phenyl group with a halogen atom, or a straight or branched C.sub.1-3 alkyl group;R.sub.2 is a C.sub.1-4 straight or branched alkyl group;R.sub.3 is a C.sub.
    Type: Grant
    Filed: December 9, 1993
    Date of Patent: February 20, 1996
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Sung-Eun Yoo, Kyu Y. Yi, Nak C. Jeong, Jee H. Suh, Seon-Ju Kim, Hwa-Sup Shin, Byung H. Lee, Kyu S. Jung
  • Patent number: 5484923
    Abstract: The present invention is directed to a process of making spirocycles of general structural formula: ##STR1## where R.sub.1 is selected from the group consisting of CO--C.sub.1-3 alkyl, cyano, carboxy, carboxy C.sub.1-6 alkyl ester, carboxamide, C.sub.1-6 alkyl sulfinyl, C.sub.1-6 alkyl sulfonyl, C.sub.1-6 methanesulfonamide and halogen; R.sub.2 is selected from the group consisting of keto or alcohol, R.sub.3 is cyano, resulting in compounds which are Class III antiarrhythmic.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: January 16, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Dongwei Cai, Richard Desmond, Yao-Jun Shi, David M. Tschaen, Thomas R. Verhoeven
  • Patent number: 5457207
    Abstract: 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: Grant
    Filed: October 5, 1993
    Date of Patent: October 10, 1995
    Assignee: Regents of the University of Minnesota
    Inventors: Simon M. N. Efange, Stanley M. Parsons
  • Patent number: 5439914
    Abstract: Compounds of the general structural formula: ##STR1## or a pharmaceutically acceptable salt, hydrate or crystal form thereof, wherein;X is O or CH.sub.2R.sup.1 is H if R.sup.2 is not H or if R.sup.2 is H then R.sup.1 is ##STR2## R.sup.2 is --H if R.sup.1 is not H or if R.sup.1 is H then R.sup.2 is; ##STR3## and R.sup.3 is ##STR4## are Class HI antiarrhythmic agents.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: August 8, 1995
    Assignee: Merck & Co., Inc.
    Inventors: David A. Claremon, Gerald S. Ponticello, Harold G. Selnick
  • Patent number: 5434158
    Abstract: Disclosed are spiro-substituted azacycles of formula I ##STR1## are selective neurokinin-3 antagonists useful in the treatment of CNS disorders.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: July 18, 1995
    Assignee: Merck & Co., Inc.
    Inventor: Shrenik K. Shah
  • Patent number: 5420150
    Abstract: The invention relates to a compound selected from those of formula (I): ##STR1## in which R.sub.1, R.sub.2, R.sub.3, A and m are as defined in the description.Medicinal product which is useful for treating depression and anxiety.
    Type: Grant
    Filed: December 27, 1993
    Date of Patent: May 30, 1995
    Inventors: Gerald Guillaumet, Tchao Podona, Gerard Adam, Beatrice Guardiola, Pierre Renard
  • Patent number: 5401747
    Abstract: A method for synthesizing camptothecin and camptothecin analogs using a novel hydroxyl-containing tricyclic intermediate and the camptothecin analogs produced by the process. The camptothecin analogs are effective inhibitors of topoisomerase. I and show antileukemic and anti-tumor activity.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: March 28, 1995
    Assignee: Research Triangle Institute
    Inventors: Monroe E. Wall, Mansukh C. Wani, Allan W. Nicholas, Govindarajan Manikumar
  • Patent number: 5397783
    Abstract: The invention relates to a compound selected from those of formula (I): ##STR1## in which R.sub.1, R.sub.2, R.sub.3, A and m are as defined in the description.Medicinal product which is useful for treating depression and anxiety.
    Type: Grant
    Filed: December 27, 1993
    Date of Patent: March 14, 1995
    Assignee: Adir et Compagnie
    Inventors: Gerald Guillaumet, Tchao Podona, Gerard Adam, Beatrice Guardiola, Pierre Renard
  • Patent number: 5391741
    Abstract: There are described a novel squarylium compound represented by the formula (I): ##STR1## and an optical information recording medium using the squarylium compound in the recording layer.
    Type: Grant
    Filed: April 23, 1993
    Date of Patent: February 21, 1995
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Ikuo Shimizu, Hiroshi Toyoda, Yukiyoshi Ito, Tsutomu Sato
  • Patent number: 5382587
    Abstract: Spirocycles of the general structural formulae: ##STR1## wherein: X is O, CH.sub.2 or SO.sub.m ;R.sup.1 is AlkylSO.sub.2 NH--, AlkylO--, AlkylSO.sub.2 --, AlkylCONH--, or NO.sub.2 --;R.sup.2 is --H, --OAlkyl, or --Alkyl;R.sup.3 is --NHCOCH.sub.2 SO.sub.m Phenyl, --NHCOCH.sub.2 SO.sub.m Alkyl,--NHCOC(CH.sub.3).sub.2 OH, or NHSO.sub.2 Alkyl;R.sup.4 and R.sup.5 are --H, or --Alkyl;R.sup.6 is ##STR2## R.sup.7 is --H, --CN, --NHSO.sub.2 Alkyl, --Br, --OAlkyl, --NH.sub.2, --NO.sub.2, --NHCOAlkyl, or NHCONHAlkyl;R.sub.8 is --H, --OH, --CN, --OAlkyl, --CONHAlkyl, --NHSO.sub.2 Alkyl, --NHCOAlkyl, --SO.sub.m Alkyl, or --CO.sub.2 Alkyl;and m is 0-2; or a pharmaceutically acceptable salt, hydrate or crystal form thereof; which are Class III antiarrhythmic agents.
    Type: Grant
    Filed: June 30, 1993
    Date of Patent: January 17, 1995
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, David A. Claremon, Jason M. Elliott
  • Patent number: 5376661
    Abstract: The invention relates to a compound selected from those of formula (I): ##STR1## in which R.sub.1, R.sub.2, R.sub.3, A and m are as defined in the description.Medicinal product which is useful for treating depression and anxiety.
    Type: Grant
    Filed: March 24, 1993
    Date of Patent: December 27, 1994
    Assignee: Adir et Compagnie
    Inventors: Gerald Guillaumet, Tchao Podona, Gerard Adam, Beatrice Guardiola, Pierre Renard
  • Patent number: 5324733
    Abstract: A class of spirocyclic piperidine derivatives are selective ligands at sigma recognition sites and are therefore useful in the treatment and/or prevention of psychiatric disorders. The claimed compounds are of the formula ##STR1## wherein, A and B are hydrogen, Q is a bond, R.sup.11, R.sup.12, and R.sup.13 are as defined in the specification.
    Type: Grant
    Filed: April 22, 1993
    Date of Patent: June 28, 1994
    Assignee: Merck Sharpe & Dohme Ltd.
    Inventors: David C. Billington, Mark S. Chambers
  • Patent number: 5322944
    Abstract: Process for preparing enantiomers of general formula (I): ##STR1## where Z, R.sub.1, R.sub.2, R.sub.3 and n are defined in the description. The compounds obtained according to the invention are useful as medicinal products.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: June 21, 1994
    Assignee: Adir et Compagnie
    Inventors: Gerald Guillaumet, Claude Fugier, Jean-Claude J. Souvie, Gerard Adam, Pierre Renard, Daniel-Henri Caignard
  • Patent number: 5300511
    Abstract: The present invention relates to novel benzopyran derivatives of formula(I) which have exellent effectiveness in the treatment of asthma as well as hypertension. ##STR1## wherein R.sub.1 is --CN, --NO.sub.2, --OCX.sub.1 X.sub.2 X.sub.3, --NH.sub.2, --NHSO.sub.2 R.sup.A, ##STR2## --SO.sub.2 R.sup.C or --SO.sub.2 NR.sup.C R.sup.D wherein X.sub.1, X.sub.2 and X.sub.3 are, each independently, F, Cl or H, except for that X.sub.1, X.sub.2 and X.sub.3 may not be hydrogen atom simulaneously; R.sup.A and R.sup.B are, each independently, a hydrogen atom, or a C.sub.1-6 alkyl group or an optionally substituted phenyl group with a halogen atom, or a straight or branched C.sub.1-3 alkyl group; and R.sup.C and R.sup.D are, each independently, a hydrogen atom or a C.sub.1-6 alkyl group or an optionally substituted phenyl group with a halogen atom, or a straight or branched C.sub.1-3 alkyl group;R.sub.2 is a C.sub.1-4 straight or branched alkyl group;R.sub.3 is a C.sub.
    Type: Grant
    Filed: May 21, 1992
    Date of Patent: April 5, 1994
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Sung-Eun Yoo, Kyu Y. Yi, Nak C. Jeong, Jee H. Suh, Seon-Ju Kim, Hwa-Sup Shin, Byung H. Lee, Kyu S. Jung
  • Patent number: 5290888
    Abstract: A process for stabilizing an ethylenically unsaturated monomer or oligomer from premature polymerization is disclosed whereby a stabilizing amount of an N-hydroxy substituted hindered amine is added to said polymerizable monomer or oligomer. The ethylenically unsaturated monomer or oligomer encompass vinyl monomers or oligomers bearing at least one polymerizable moiety. The N-hydroxy substituted hindered amine inhibits premature polymerization in the liquid and/or vapor phase.
    Type: Grant
    Filed: October 2, 1992
    Date of Patent: March 1, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Leslie R. Gatechair, James L. Hyun, Peter J. Schirmann
  • Patent number: 5286865
    Abstract: 1-Hydrocarbyloxy substituted hindered amine compounds which also contain a reactive functional group such as hydroxy, amino, oxirane or carboxyl can be chemically attached to selected polymer substrates by condensation reactions to give polymers containing a chemically-bonded, non-migrating stabilizer having excellent stabilization efficacy for protecting said polymer substrate from the adverse effects of actinic light.
    Type: Grant
    Filed: June 24, 1992
    Date of Patent: February 15, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: James P. Galbo, Ramanathan Ravichandran, Peter J. Schirmann, Andrew Mar
  • Patent number: 5276026
    Abstract: Tetrahydronaphthaleneamine derivatives having the formula ##STR1## wherein R, R', R.sub.1 and R.sub.2 are as defined herein, are novel calcium channel blockers.
    Type: Grant
    Filed: January 21, 1993
    Date of Patent: January 4, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joel C. Barrish, Steven H. Spergel
  • Patent number: 5252587
    Abstract: This invention relates to novel N-derivatives of 1-deoxy nojirimycin, to the method for their preparation and to their use in the treatment of diabetes and the use against retro-viruses, particularly in the treatment of acquired immuno-deficiency syndrome (AIDS).
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: October 12, 1993
    Assignee: Merrell Dow Pharmaceuticals, Inc.
    Inventors: Brigitte Lesur, Jean-Bernard Ducep, Charles Danzin
  • Patent number: 5250691
    Abstract: Compounds having the formula ##STR1## exhibiting antibacterial activity.
    Type: Grant
    Filed: September 9, 1991
    Date of Patent: October 5, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Henner Straub, Jakob-Matthias Drossard
  • Patent number: 5221745
    Abstract: The compounds ##STR1## in which Z is ##STR2## where R.sup.4 is -H or alkyl; q is one of the integers 0, 1 or 2; Y is H.sub.2 or O; or Z, taken with R.sup.1 forms ##STR3## R.sup.1 is hydrogen or alkyl or combined with Z as described above; R.sup.2 and R.sup.3 are, independently, hydrogen, alkyl, alkoxy, aralkoxy, alkanoyloxy, hydroxy, halo, amino, mono- or dialkylamino, carbamoyl or sulfonamido or R.sup.2 and R.sup.3, taken together are methylenedioxy, ethylenedioxy or propylenedioxy; m is one of the integers 1, 2 or 3; n is one of the integers 0 or 1; or a pharmaceutically acceptable salt thereof are antipsychotic, antidepressant and anxiolytic agents useful in relieving the symptoms of these disease states.
    Type: Grant
    Filed: May 13, 1992
    Date of Patent: June 22, 1993
    Assignee: American Home Products Corp.
    Inventor: Gary P. Stack
  • Patent number: 5219860
    Abstract: A class of spirocyclic piperidine derivatives are selective ligands at sigma recognition sites and are therefore useful in the treatment and/or prevention of psychiatric disorders.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: June 15, 1993
    Assignee: Merck Sharp & Dohme Limited
    Inventors: Mark S. Chambers, David C. Billington
  • Patent number: 5206240
    Abstract: Spirocycles of general structural formula: ##STR1## are Class III antiarrhythmic agents.
    Type: Grant
    Filed: June 3, 1991
    Date of Patent: April 27, 1993
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Jason M. Elliott, David A. Claremon, Gerald S. Ponticello, David C. Remy, Harold G. Selnick
  • Patent number: 5204349
    Abstract: Compounds of the formula: ##STR1## where R.sup.1 is hydrogen or hydroxy and R.sup.2 is a substituted amino group, a substituted heterocyclic ring or a substituted alkyl. These compounds are oxytocin and vasopressin antagonists useful in the treatment of preterm labor, dysmenorrhea and for the stoppage of labor preparatory to cesarean delivery, timing of parturition, uterine hyperactivity, endometriosis, hypertension, congestive heart failure, hyponatremia and cognitive disorders. Also disclosed are pharmaceutical compositions containing these compounds, methods of their use and methods of their preparation.
    Type: Grant
    Filed: September 16, 1991
    Date of Patent: April 20, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Mark G. Bock, Ben E. Evans, Roger M. Freidinger, Kevin Gilbert, Doug W. Hobbs, James B. Hoffman, George F. Lundell, Douglas J. Pettibone
  • Patent number: 5179119
    Abstract: This invention relates to 1,3-dihydro-1-(pyridinylamino)-2H-indol-2-ones of the formula ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen, loweralkyl, aryl, arylloweralkyl or heteroarylloweralkyl selected from the group consisting of pyridinylmethyl, pyridinylethyl, thienylmethyl, thienylethyl; or R.sub.2 and R.sub.3 together form a cycloalkane ring of 4 to 6 carbons or a spiro-fused aryl cycloalkane or heterocycloalkyl selected from the group consisting of piperidine and tetrahydropyran; X and Y are independently hydrogen, halogen, hydroxy, loweralkyl, loweralkoxy, nitro, amino or trifluoromethyl; m and n are independently integers of 1 to 3, the pharmaceutically acceptable acid addition salts thereof and, where applicable the optical, geometrical and stereoisomers and racemic mixtures thereof. The compounds of this invention display utility as analgesics, anticonvulsants, for enhancing memory and for the treatment of Alzheimer's disease.
    Type: Grant
    Filed: July 26, 1991
    Date of Patent: January 12, 1993
    Assignee: Hoechst-Roussel Pharmaceuticals Incorporated
    Inventors: Richard C. Effland, David G. Wettlaufer
  • Patent number: 5136037
    Abstract: There are disclosed compounds of the formula, ##STR1## where n is 0 or 1; A is ##STR2## where X in each occurrence is independently hydrogen, halogen, loweralkyl, hydroxy, nitro, loweralkoxy, amino, cyano, trifluoromethyl or methylthio; Y in each occurrence is independently hydrogen, halogen, loweralkyl, hydroxy, nitro, loweralkoxy, amino, cyano, trifluoromethyl or methylthio; m is 1 or 2; k is 1 or 2; R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, ##STR3## or alternatively R.sub.1 +R.sub.2 taken together with the carbon atom to which they are attached form a cyclopentane, cyclohexane, cycloheptane, pyran, thiopyran, indan or piperidine ring; R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl, or alternatively R.sub.3 +R.sub.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: August 4, 1992
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Nicholas J. Hrib, John G. Jurcak
  • Patent number: 5091387
    Abstract: Disclosed are spirocyclic compounds of the formula: ##STR1## The compounds of formula I are oxytocin antagonists useful in the treatment of preterm labor and dysmenorrhea, and for the stoppage of labor preporatory to Caesarian delivery. Also disclosed are pharmaceutical compositions containing these compounds as well as methods for preparing the compounds.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: February 25, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Ben E. Evans, Douglas J. Pettibone, Roger M. Friedinger
  • Patent number: 5053511
    Abstract: This invention relates to 1,3-dihydro-1-(pyridinylamino)-2H-indol-2-ones of the formula ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen, loweralkyl, aryl, arylloweralkyl or heteroarylloweralkyl selected from the group consisting of pyridinylmethyl, pyridinylethyl, thienylmethyl, thienylethyl; or R.sub.2 and R.sub.3 together form a cycloalkane ring of 4 to 6 carbons or a spiro-fused aryl cycloalkane or heterocycloalkyl selected from the group consisting of piperidine and tetrahydropyran; X and Y are independently hydrogen, halogen, hydroxy, loweralkyl, loweralkoxy, nitro, amino or trifluoromethyl; m and n are independently integers of 1 to 3, the pharmaceutically acceptable acid addition salts thereof and, where applicable the optical, geometrical and stereoisomers and racemic mixtures thereof. The compounds of this invention display utility as analgesics, anticonvulsants, for enhancing memory and for the treatment of Alzheimer's disease.
    Type: Grant
    Filed: June 11, 1990
    Date of Patent: October 1, 1991
    Assignee: Hoechst-Roussel Pharmaceuticals Incorporated
    Inventors: Richard C. Effland, David G. Wettlaufer
  • Patent number: 5015678
    Abstract: The Michael addition products of N-hydroxy hindered amines with alpha,beta-unsaturated carbonyl compounds including derivatives of esters, amids, imides and anhydrides are effective stabilizers for protecting organic polymers from the deleterious effects of actinic light.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: May 14, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, James P. Galbo, Ramanathan Ravichandran
  • Patent number: 5006531
    Abstract: There are disclosed compounds having the formula ##STR1## where n is 0, 1, or 2;p and q are each independently 1, 2 or 3;each X and each Y are independently hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, nitro, amino, loweralkylamino, diloweralkylamino, trifluoromethyl or loweralkythio;R.sub.1 and R.sub.2 are each independently hydrogen or loweralkyl; andR.sub.3 is hydrogen, loweralkyl, loweralkylcarbonyl, arylloweralkyl or aminocarbonyl;which are useful as analgesic, antipsychotic and anticonvulsant agents.
    Type: Grant
    Filed: July 10, 1989
    Date of Patent: April 9, 1991
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Grover C. Helsley, John J. Tegeler, Kirk D. Shoger
  • Patent number: 5006537
    Abstract: This invention relates to 1,3-dihydro-1-(pyridinylamino)-2H-indol-2-ones of the formula ##STR1## where R.sub.1,R.sub.2 and R.sub.3 are independently hydrogen, loweralkyl, aryl, arylloweralkyl or heteroarylloweralkyl selected from the group consisting of pyridinylmethyl, pyridinylethyl, thienylmethyl, thienylethyl; or R.sub.2 and R.sub.3 together form a cycloalkane ring of 4 to 6 carbons or a spiro-fused aryl or heteroaryl cycloalkane; X and Y are independently hydrogen, halogen, hydroxy, loweralkyl, loweralkoxy, nitro, amino or trifluoromethyl; m and n are independently integers of 1 to 3, the pharmaceutically acceptable acid addition salts thereof and, where applicable the optical, geometrical and stereoisomers and racemic mixtures thereof. The compounds of this invention display utility as analgesics, anticonvulsants, for enhancing memory and for the treatment of Alzheimer's disease.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: April 9, 1991
    Assignee: Hoechst-Roussel Pharmaceuticals, Inc.
    Inventors: Richard C. Effland, David G. Wettlaufer
  • Patent number: 4971964
    Abstract: A pyridine derivative represented by formula (I): ##STR1## wherein the symbols are as defined in the specification, which exhibits selective, potential, and long-lasting inhibitory activity on biosynthesis of thromboxane A.sub.2 and is useful in the treatment and prevention of a broad range of diseases.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: November 20, 1990
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Koji Suzuki, Obase Hiroyuki, Akira Karasawa, Shiro Shirakura, Kubo Shizuoka, Ichiro Miki, Akio Ishii
  • Patent number: 4921955
    Abstract: The invention relates to a process for the preparation of 1,5-disubstituted imidazoles of the formula ##STR1## by alkylation of an N-cyanoformamidine of the formula IIX--NH--CH.dbd.N--CH (II)to form an N,N-disubstituted N'-cyanoformamidine of the formula ##STR2## which is cyclised under the action of bases to form a 4-aminoimidazole of the formula ##STR3## and then reduced to form the product of the formula I. The invention relates also to a special process for the reduction of the aminoimidazole V to I, and to intermediate compounds for carrying out this process and to processes for the preparation of the intermediate compounds.The meaning of the substituents X and L is explained in detail in the text.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: May 1, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Werner Topfl
  • Patent number: 4863932
    Abstract: Azadecalins and C-7 substituted decalins with squalene oxide cyclase inhibitory activity are useful as inhibitors of cholesterol synthesis and hence may be used in pharmaceuticals for regulating cholesterol levels in a mammal.
    Type: Grant
    Filed: March 11, 1988
    Date of Patent: September 5, 1989
    Assignees: Somatogenetics International, Inc., Dartmouth College
    Inventors: Michael Sinensky, Thomas A. Spencer