Additional Hetero Ring Attached Directly Or Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 540/596)
  • Patent number: 5698607
    Abstract: Tertiary diamines having two saturated heterocyclic rings joined by an aliphatic carbon chain, of the general formula ##STR1## in which each A is a two- to four-membered aliphatic carbon chain substituted if desired by one or more C.sub.1 -C.sub.4 -alkyl groups, are prepared in one stage by catalytic hydrogenation of the corresponding dinitriles of the general formulaN.tbd.C--A--C.tbd.N IIThe diamines preparable in accordance with the invention are particularly suitable as catalysts for the production of polyurethanes.
    Type: Grant
    Filed: January 30, 1997
    Date of Patent: December 16, 1997
    Assignee: Lonza AG
    Inventors: Josef Heveling, Andreas Gerhard, Ulrich Daum
  • Patent number: 5696154
    Abstract: Provided are brefeldin A derivatives of the formula: ##STR1## wherein one of R.sub.1 and R.sub.2 is H and the other of R.sub.1 and R.sub.2 is a substituent group having 1 to 12 carbon atoms containing a basic nitrogen atom or a quaternary ammonium group, or a salt thereof. These derivatives exhibit good antitumor activity, and are administrable to human patients without the problems associated with brefeldin A.
    Type: Grant
    Filed: June 29, 1994
    Date of Patent: December 9, 1997
    Assignees: The United States of America as represented by the Department of Health and Human Services, Starks Associates, Inc.
    Inventors: Louis Malspeis, B. Rao Vishnuvajjala, Jeffrey G. Supko, Charles Theodore Kane, Jr.
  • Patent number: 5686447
    Abstract: Novel aminoalkyloximes, precursors and processes for the preparation thereof, and methods of treating depression and obsessive compulsive disorders are described.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: November 11, 1997
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Gregory M. Shutske, Brian S. Freed, John D. Tomer, IV, R. Richard L. Hamer
  • Patent number: 5686483
    Abstract: Novel aminoalkyloximes, precursors and processes for the preparation thereof, and methods of treating depression and obsessive compulsive disorders are described.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: November 11, 1997
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Gregory M. Shutske, Brian S. Freed, John D. Tomer, IV, R. Richard L. Hamer
  • Patent number: 5686446
    Abstract: Novel aminoalkyloximes, precursors and processes for the preparation thereof, and methods of treating depression and obsessive compulsive disorders are described.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: November 11, 1997
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Gregory M. Shutske, Brian S. Freed, John D. Tomer, IV, R. Richard L. Hamer
  • Patent number: 5684021
    Abstract: Novel aminoalkyloximes, precursors and processes for the preparation thereof, and methods of treating depression and obsessive compulsive disorders are described.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: November 4, 1997
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Gregory M. Shutske, Brian S. Freed, John D. Tomer, IV, R. Richard L. Hamer
  • Patent number: 5672620
    Abstract: A compound having the structure: ##STR1## wherein (a) n is from 1 to about 3;(b) X is selected from the group consisting of O, S, SO, or SO.sub.2 ;(c) Y is independently hydrogen or straight, branched or cyclic alkyl having from 1 to about 4 carbon atoms, or the Y's are bonded together to form an alkanyl ring having from 3 to about 7 atoms;(d) Z is hydrogen or straight, branched or cyclic alkyl having from 3 to about 10 atoms other than hydrogen;(e) W is hydrogen or straight, branched or cyclic alkyl, aryl, hydroxy or alkoxy; and(f) R.sub.1 and R.sub.2 are independently hydrogen or straight, branched or cyclic alkyl having from one to 10 carbon atoms, aryl, heterocyclyl, heteroaryl, hydroxy, or alkoxy; or R.sub.1 and R.sub.2 are bonded together to form a ring having from from 3 to about 7 atoms wherein one to three atoms may be heteroatoms.pharmaceutical compositions comprising such compounds, and methods of treating inflammation or pain using such compounds.
    Type: Grant
    Filed: February 1, 1996
    Date of Patent: September 30, 1997
    Assignee: The Procter & Gamble Company
    Inventors: Michael Wiard Scherz, Laurence Ichih Wu
  • Patent number: 5668165
    Abstract: Disclosed is a method for the inhibition of binding of a ligand to an RNA, the inhibition being mediated by a small organic molecule that binds to the RNA, thereby inhibiting ligand binding. A preferred class of small organic molecules are compounds exemplified by 2,5-Bis[3-(2-N,N-dimethylaminopropylamidino)phenyl]furan.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 16, 1997
    Assignee: Scriptgen Pharmaceuticals, Inc.
    Inventors: Mark A. Wuonola, Zhe Li
  • Patent number: 5656632
    Abstract: Disclosed are compounds of the formula ##STR1## or the pharmaceutically acceptable salts thereof wherein the 6-membered A ring may be optionally substituted with up to four groups independently selected from halogen, hydroxy, lower alkyl, or lower alkoxy;Ar represents optionally substituted aryl or heteroarylZ represents carbon or nitrogen provided thatwhere Z is carbon, R.sub.11 represents hydrogen, halogen, hydroxy, lower alkyl, or lower alkoxy, or phenyl optionally substituted with one or two groups selected from hydrogen, halogen, hydroxy, lower alkyl, or lower alkoxy; andwhere Z is nitrogen, R.sub.11 represents an electron pair;R.sub.5 is hydrogen or lower alkyl;L and m represent integers;n is 0, or an integer;R.sub.12 and R.sub.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: August 12, 1997
    Assignee: Neurogen Corporation
    Inventors: Xiao-shu He, Brian de Costa, Jan W. F. Wasley
  • Patent number: 5656625
    Abstract: Certain nitrogen-containing cyclohetero cycloalkylaminoaryl compounds are described for treatment of CNS disorders such as cerebral ischemia, psychoses and convulsions. Compounds of particular interest are of the formula: ##STR1## wherein each of R.sup.1, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 is independently selected from hydrido, lower alkyl, benzyl, and haloloweralkyl;wherein each of R.sup.2, R.sup.3 and R.sup.8 through R.sup.11 is independently selected from hydrido, hydroxy, loweralkyl, benzyl, phenoxy, benzyloxy and haloloweralkyl; wherein n is an integer of from four to six; wherein m is an integer of from two to four; wherein A is selected from phenyl, naphthyl, benzothienyl, benzofuranyl and thienyl; wherein any of the foregoing A groups can be further substituted with one or more substituents independently selected from hydrido, hydroxy, loweralkyl, loweralkoxy, halo, haloloweralkyl, amino, monoloweralkylamino and diloweralkylamino; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: August 12, 1997
    Assignees: The United States of America as represented by the Department of Health and Human Services, Brown University Research Foundation
    Inventors: Wayne Bowen, Brian R. de Costa, Celia Dominguez, Xiao-Shu He, Kenner C. Rice
  • Patent number: 5643896
    Abstract: The present invention provides a compound of formula I ##STR1## wherein R.sub.1 is hydrogen, a hydroxy protecting group, or methyl;R.sub.2 and R.sub.3 are independently C.sub.1 -C.sub.6 alkyl, or R.sub.2 and R.sub.3, together with the nitrogen to which they are attached, form a heterocycle selected from the group consisting of pyrrolidino, hexamethyleneimino, morpholino, and piperidino;Z is bromo, chloro, fluoro, hydroxy, a protected hydroxy, or hydrogen; and pharmaceutically acceptable salts and solvates thereof.The present invention further provides pharmaceutical compositions containing compounds of formula I, optionally containing estrogen or progestin, and the use of such compounds alone, or in combination with estrogen or progestin, for alleviating the symptoms of post-menopausal syndrome, particularly osteoporosis, cardiovascular related pathological conditions, and estrogen-dependent cancer.
    Type: Grant
    Filed: September 22, 1995
    Date of Patent: July 1, 1997
    Assignee: Eli Lilly and Company
    Inventors: George J. Cullinan, James J. Sales
  • Patent number: 5622973
    Abstract: The present invention is directed to certain novel compounds identified as di- and tri-substituted piperidines, pyrrolidines, and hexahydro-1H-azepines of the general structural formula: ##STR1## wherein R.sub.1, R.sub.4, R.sub.5, A, X, Y, and n 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 di and tri substituted piperidines, pyrrolidines, and hexahydro-1H-azepines as the active ingredient thereof are also disclosed.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: April 22, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Gregori J. Morriello, Arthur A. Patchett, Lihu Yang
  • Patent number: 5622974
    Abstract: This invention relates to the fields of pharmaceutical and organic chemistry and provides novel 3-benzyl-benzofurans which are .alpha.-substituted with ether, thioether amino, cyano or halo that are useful for the treatment of the various medical indications associated with post-menopausal syndrome, as well as estrogen dependent diseases including cancer of the breast, uterus and cervix. The present invention further relates to intermediate compounds and processes useful for preparing the pharmaceutically active compounds of the present invention, and pharmaceutical compositions.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: April 22, 1997
    Assignee: Eli Lilly and Company
    Inventor: Brian S. Muehl
  • Patent number: 5620971
    Abstract: The present invention relates to novel compounds which possess a broad range of useful biological activities. These compounds can maintain, increase, or restore sensitivity of cells to therapeutic or prophylactic agents. They can also suppress, modify, or significantly reduce an immune response, including an autoimmune response in a mammal. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well-suited for treatment of multi-drug resistant cells, for prevention of the development of multi-drug resistance, for use in multi-drug resistant cancer therapy, and for prevention or treatment of graft rejection and various autoimmune diseases.
    Type: Grant
    Filed: March 25, 1994
    Date of Patent: April 15, 1997
    Assignee: Vertex Pharmaceuticals Incorporated
    Inventors: David M. Armistead, Jeffrey O. Saunders, Joshua S. Boger
  • Patent number: 5614639
    Abstract: The present invention provides processes for preparing 2-substituted benzo[b]thiophene compounds, some of which are useful as intermediates for preparing pharmaceutically-active compounds and others which are useful, inter alia, for the treatment of osteoporosis in postmenopausal women.
    Type: Grant
    Filed: March 31, 1995
    Date of Patent: March 25, 1997
    Assignee: Eli Lilly and Company
    Inventors: Kenneth L. Hauser, Alan D. Palkowitz, Daniel J. Sall, Kenneth J. Thrasher
  • Patent number: 5610295
    Abstract: Amide Derivatives of formula (I): R.sup.5 NR.sup.4 (CR.sub.2).sub.2 CHR.sup.3 CONR.sup.1 R.sup.2 and their pharmaceutically acceptable salts are 5-HT1A binding agents and may be used, for example, as anxiolytics. The radicals, R, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have specified meanings.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: March 11, 1997
    Assignee: John Wyeth & Brother, Ltd.
    Inventors: Ian A. Cliffe, Anderson D. Ifill
  • Patent number: 5610308
    Abstract: A process is provided for preparing intermediates of the structure ##STR1## wherein Rpg is preferably .dbd.CHC.sub.6 H.sub.5 ; and P.G. is a protecting group CBZ or BOC, wherein a protected guanylpyrazole is reacted with an azacycloalkyl, azacycloalkenyl or azaheteroalkyl derivative (such as a piperidine derivative) in the presence of a DBU catalyst. The resulting intermediate may be used as a starting material for preparing thrombin inhibitors.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: March 11, 1997
    Assignee: Bristol-Myers Squibb Company
    Inventors: Sharon D. Real, David R. Kronenthal
  • Patent number: 5610227
    Abstract: The present invention provides anionic polymerization initiators, comprising lithium amino magnesiate complexes, resulting in diene polymer and copolymer elastomers. The invention initiators have stable living ends at high polymerization temperatures and produce polymers containing a high level of tertiary amine functionality. Such polymers exhibit an increased efficiency in coupling termination reactions, and elastomers and products prepared from such polymers exhibit reduced hysteresis properties. Methods are also provided for preparing the initiators, the polymers and the elastomers.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 11, 1997
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: Thomas A. Antkowiak, James E. Hall
  • 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: 5606076
    Abstract: The present invention is directed to a process for the synthesis of 2-arylbenzo[b]thiophenes.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 25, 1997
    Assignee: Eli Lilly and Company
    Inventors: James A. Aikins, Tony Y. Zhang
  • Patent number: 5606075
    Abstract: The present invention is directed to new processes for the synthesis of 2-aryl benzo[b]thiophenes.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 25, 1997
    Assignee: Eli Lilly and Company
    Inventors: David W. Hoard, Wayne D. Luke
  • Patent number: 5602168
    Abstract: Disclosed are compounds of the formula ##STR1## or the pharmaceutically acceptable salts thereof wherein the 6-membered A ring may be optionally substituted with up to four groups independently selected from halogen, hydroxy, lower alkyl, or lower alkoxy;Ar represents optionally substituted aryl or heteroarylZ represents carbon or nitrogen provided thatwhere Z is carbon, R.sub.11 represents hydrogen, halogen, hydroxy, lower alkyl, or lower alkoxy, or phenyl optionally substituted with one or two groups selected from hydrogen, halogen, hydroxy, lower alkyl, or lower alkoxy; andwhere Z is nitrogen, R.sub.11 represents an electron pair;R.sub.5 is hydrogen or lower alkyl;L and m represent integers;n is 0, or an integer;R.sub.12 and R.sub.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: February 11, 1997
    Assignee: Neurogen Corporation
    Inventors: Xiao-shu He, Brian de Costa, Jan W. F. Wasley
  • Patent number: 5594138
    Abstract: Disclosed is a method of fluorescent detection of a nucleic acid. The method comprises contacting to the nucleic acid a bis-dicationic aryl furan compound, such as 2,5-bis[4-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl) phenyl] furan; 2,5-bis{[4-(N-isopropyl) amidino] phenyl}furan; and physiologically acceptable salts thereof, and exposing the nucleic acid to light at a frequency to induce fluorescence of the compound. A method for fluorescent detection of cytoskeleton elements, and novel bis-dicationic aryl furan compounds are also disclosed.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: January 14, 1997
    Assignees: Georgia State University Research Foundation, The University of North Carolina at Chapel Hill
    Inventors: Christine C. Dykstra, Richard R. Tidwell, David W. Boykin, W. David Wilson, Jaroslaw Spychala, Bijan P. Das, Arvind Kumar
  • Patent number: 5585374
    Abstract: Amide derivatives of formula (I) and their pharmaceutically acceptable salts (where a and b each represent 0, 1, 2 or 3 such that a+b=0, 1, 2 or 3, the dotted line represents an optional double bond, A is an optionally substituted C.sub.1-2 -alkylene chain, R is mono or bicyclic aryl or heteroaryl radical, R.sup.1 is hydrogen or lower alkyl, R.sup.2 is an aryl, aralkyl, heteroaryl or heteroarylalkyl and --CONR.sup.3 R.sup.4 represents a specified amide group) are 5-HT.sub.1A binding agents and may be used, for example, as anxiolytics.
    Type: Grant
    Filed: February 1, 1995
    Date of Patent: December 17, 1996
    Assignee: John Wyeth Brother, Limited
    Inventors: Ian A. Cliffe, Alan C. White
  • Patent number: 5583222
    Abstract: The compounds of formula I ##STR1## wherein R.sup.1 -R.sup.9, R.sup.15, A, X, Y, Z and n have the meaning given in the specification are active as protein kinase inhibitors and can be used as medicaments, particularly for the treatment of inflammatory skin disorders and alopecia.
    Type: Grant
    Filed: January 4, 1995
    Date of Patent: December 10, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Pierre Barbier, Isabelle Huber, Fernand Schneider, Josef Stadlwieser, Sven Taylor
  • Patent number: 5559128
    Abstract: The present invention is directed to certain novel compounds identified as 3-substituted piperidines of the general structural formula: ##STR1## wherein R.sup.1, R.sup.1a, R.sup.2a, R.sup.4, R.sup.5, A, X, and Y 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 these compounds as the active ingredient thereof are also disclosed.
    Type: Grant
    Filed: April 18, 1995
    Date of Patent: September 24, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Prasun K. Chakravarty, Ravi Nargund, Robert W. Marquis, Arthur A. Patchett, Lihu Yang
  • Patent number: 5552401
    Abstract: The present invention provides a compound of formula I ##STR1## wherein R.sub.1 is hydrogen, a hydroxy protecting group, or methyl;R.sub.2 and R.sub.3 are independently C.sub.1 -C.sub.6 alkyl, or R.sub.2 and R.sub.3, together with the nitrogen to which they are attached, form a heterocycle selected from the group consisting of pyrrolidino, hexamethyleneimino, morpholino, and piperidino;Z is bromo, chloro, fluoro, hydroxy, a protected hydroxy, or hydrogen; and pharmaceutically acceptable salts and solvates thereof.The present invention further provides pharmaceutical compositions containing compounds of formula I, optionally containing estrogen or progestin, and the use of such compounds alone, or in combination with estrogen or progestin, for alleviating the symptoms of post-menopausal syndrome, particularly osteoporosis, cardiovascular related pathological conditions, and estrogen-dependent cancer.
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: September 3, 1996
    Assignee: Eli Lilly and Company
    Inventors: George J. Cullinan, James J. Sales
  • Patent number: 5523309
    Abstract: The present invention provides a compound of formula I ##STR1## wherein R.sub.1 is H, OH, halo, OCO(C.sub.1 -C.sub.6 alkyl), OCO(aryl), OSO.sub.2 (C.sub.4 -C.sub.6 alkyl), OCOO(C.sub.1 -C.sub.6 alkyl), OCOO(aryl), OCONH(C.sub.1 -C.sub.6 alkyl), or OCON(C.sub.1 -C.sub.6 alkyl).sub.2 ;R.sub.2 is aryl, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, or 4-cyclohexanol;R.sub.3 is O(CH.sub.2).sub.2 or O(CH.sub.2).sub.3 ;R.sub.4 and R.sub.5 are optionally CO(CH.sub.2).sub.2 CH.sub.3, CO(CH.sub.2).sub.3 CH.sub.3 C.sub.1 -C.sub.6 alkyl, or R.sub.4 and R.sub.5 combine to form, with the nitrogen to which they are attached, piperidine, morpholine, pyrrolidine, 3-methylpyrrolidine, 3,3-dimethylpyrrolidine, 3,4-dimethylpyrrolidine, azepine, or pipecoline;R.sub.6 is >CH(C.sub.1 -C.sub.5 alkyl), >CH(C.sub.2 -C.sub.5 alkenyl), >C.dbd.CH(C.sub.1 -C.sub.5 alkyl) >CH(aryl), >C(OH)(C.sub.1 -C.sub.5 alkyl), >C(OH)(C.sub.2 -C.sub.5 alkenyl), >C(OH)aryl;and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: June 4, 1996
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Jeffrey A. Dodge
  • Patent number: 5519023
    Abstract: The invention relates to compounds of the general formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and Z are as defined in the description, their optical isomers and their addition salts with a pharmaceutically-acceptable acid or base and medicaments containing the same, useful in the treatment and prevention of stress, anxiety, and related ailments.
    Type: Grant
    Filed: July 2, 1993
    Date of Patent: May 21, 1996
    Assignee: Adir et Compagnie
    Inventors: Marc Payard, Genevieve Baziard-Mouysset, Gilbert De Saqui-Sannes, Beatrice Guardiola, Daniel-Henri Caignard, Pierre Renard, Gerard Adam
  • Patent number: 5510488
    Abstract: An improved process for the preparation of trans-6- 2-(substituted-pyrrole-1-yl)alkyl!pyran-2-ones by a novel synthesis is described where .alpha.-metalated N,N-disubstituted acetamide is converted in seven operations to the desired products, and specifically, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N, 4-diphenyl-1- 2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl!-1H-pyrrol e-3-carboxamide, as well as other valuable intermediates used in the processes and prodrugs which are bioconverted to hypolipidemic and hypocholesterolemic agents and pharmaceutical compositions of the same.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: April 23, 1996
    Assignee: Warner-Lambert Company
    Inventors: Donald E. Butler, Tung Van Le, Thomas N. Nanninga
  • Patent number: 5500443
    Abstract: A compound of formula (I): ##STR1## in which: X represents oxygen or methylene,n represents 1, 2 or 3,R.sub.1 represents hydrogen, aminocarbonyl or hydroxymethyl,R.sub.2 represents: ##STR2## in which R.sub.3 and R.sub.4 are as defined in the description, the isomers thereof and the addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same are useful in the treatment of schizophrenia.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: March 19, 1996
    Assignee: Adir et Compagnie
    Inventors: Gilbert Lavielle, Patrick Hautefaye, Olivier Muller, Mark Millan, Mauricette Brocco
  • Patent number: 5492916
    Abstract: The present invention is directed to certain novel compounds identified as di- and tri-substituted piperidines, pyrrolidines, and hexahydro-1H-azepines of the general structural formula: ##STR1## wherein R.sub.1, R.sub.4, R.sub.5, A,X,Y, and n 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 di and tri substituted piperidines, pyrrolidines, and hexahydro-1H-azepines as the active ingredient thereof are also disclosed.
    Type: Grant
    Filed: October 17, 1994
    Date of Patent: February 20, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Gregori J. Morriello, Arthur A. Patchett, Lihu Yang
  • Patent number: 5492922
    Abstract: The present invention provides pharmaceutically active compounds of formula I ##STR1## wherein R.sup.1 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), or --OSO.sub.2 (C.sub.2 -C.sub.6 alkyl);R.sup.2 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), --OSO.sub.2 (C.sub.2 -C.sub.6 alkyl), or halo, providing when Z is --S--, R.sup.2 is not halo;R.sup.3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino;n is 2 or 3; andz is --O-- or --S--;or a pharmaceutically acceptable salt thereof, for inhibiting aortal smooth muscle proliferation.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: February 20, 1996
    Assignee: Eli Lilly and Company
    Inventor: Alan D. Palkowitz
  • Patent number: 5492921
    Abstract: The present invention provides novel benzothiophene compounds of formula I ##STR1## wherein R is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --O--CO--(C.sub.1 -C.sub.6 alkyl), --O--CO--Ar in which Ar is optionally substituted phenyl, or --O--SO.sub.2 --(C.sub.4 -C.sub.6 alkyl);R.sup.1 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --O--CO--(C.sub.1 -C.sub.6 alkyl), --O--CO--Ar in which Ar is optionally substituted phenyl, --O--SO.sub.2 --(C.sub.4 -C.sub.6 alkyl) chloro or bromo;R.sup.2 is --H or --OH;n is 2 or 3; andR.sup.3 and R.sup.4 each are independently C.sub.1 -C.sub.4 alkyl, or combine to form 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof, for inhibiting aortal smooth muscle proliferation.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: February 20, 1996
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones
  • Patent number: 5491149
    Abstract: This invention relates to substituted dihydroxypropylamines, a process to prepare intermediates useful for the synthesis of these compounds, compositions comprising such compounds, and a method of treating retroviral infection.
    Type: Grant
    Filed: August 26, 1994
    Date of Patent: February 13, 1996
    Assignee: The Du Pont Merck Pharmaceutical Company
    Inventor: Prabhakar K. Jadhav
  • Patent number: 5488058
    Abstract: The present invention provides pharmaceutically active compounds of formula I ##STR1## wherein R.sup.1 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), or --OSO.sub.2 (C.sub.2 -C.sub.6 alkyl);R.sup.2 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), --OSO.sub.2 (C.sub.2 -C.sub.6 alkyl), or halo, providing when Z is --S--, R.sup.2 is not halo;R.sup.3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino;n is 2 or 3; andz is --O-- or --S--;or a pharmaceutically acceptable salt thereof, for inhibiting restenosis.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: January 30, 1996
    Assignee: Eli Lilly and Company
    Inventor: Alan D. Palkowitz
  • Patent number: 5482949
    Abstract: The present invention relates to sulfonate derivatives of 3-aroylbenzo[b]thiophenes, pharmaceutical formulations containing these compounds and methods of using such compounds for inhibiting the loss of bone, lowering serum cholesterol levels and therapeutically treating hormone dependent mammalian breast and uterine carcinoma.
    Type: Grant
    Filed: March 19, 1993
    Date of Patent: January 9, 1996
    Assignee: Eli Lilly and Company
    Inventors: Larry J. Black, Henry U. Bryant, George J. Cullinan
  • Patent number: 5478934
    Abstract: Disclosed are compounds of the formula: ##STR1## wherein: A represents arylalkyl, aryl or heteroaryl; X is nitrogen or CH; and R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent organic or inorganic substituents;and the pharmaceutically acceptable salts thereof; useful for treating disorders of the central nervous system.
    Type: Grant
    Filed: November 23, 1994
    Date of Patent: December 26, 1995
    Inventors: Jun Yuan, Jan W. F. Wasley
  • Patent number: 5476934
    Abstract: A nitrogen-containing perfluoroalkanoyl peroxide is provided which is represented by the formula: ##STR1## wherein Rf.sub.1 and Rf.sub.2 independently stand for an alkyl group of 1 to 5 carbon atoms, provided that Rf.sub.1 and Rf.sub.2 are joined to each other in one of the three patterns of union, 1) direct union, 2) union through the medium of an oxygen atom or 3) union through the medium of a nitrogen atom to form one of the three rings, i.e. five-membered ring, six-membered ring or seven-membered ring.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: December 19, 1995
    Assignee: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventors: Haruhiko Fukaya, Takashi Abe, Eiji Hayashi, Yoshio Hayakawa
  • Patent number: 5470849
    Abstract: This invention relates to a method of inhibiting platelet aggregation, and compounds which are mimics of the peptide sequence Arg-Gly-Asp.
    Type: Grant
    Filed: April 30, 1993
    Date of Patent: November 28, 1995
    Assignee: SmithKline Beecham Corp.
    Inventors: James F. Callahan, William F. Huffman
  • Patent number: 5470981
    Abstract: An improved process for the preparation of trans-6-[2-(substituted-pyrrole-1-yl)alkyl]pyran-2-ones by a novel synthesis is described where .alpha.-metalated N,N-disubstituted acetamide is converted in seven operations to the desired products, and specifically, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahy dro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H pyrrole-3-carboxamide, as well as other valuable intermediates used in the processes and prodrugs which are bioconverted to hypolipidemic and hypocholesterolemic agents and pharmaceutical compositions of the same.
    Type: Grant
    Filed: January 18, 1995
    Date of Patent: November 28, 1995
    Assignee: Warner-Lambert Company
    Inventors: Donald E. Butler, Tung V. Le, Thomas N. Nanninga
  • Patent number: 5446060
    Abstract: The present invention relates to compounds of formula: ##STR1## in which A is selected from pyrrolidino, piperidino, morpholino, 1-imidazolyl, hexamethylenimino and 1-piperazinyl groups, these groups being unsubstituted or it being possible for them to contain 1 or 2 substituents selected from C.sub.1 -C.sub.3 alkyl and C.sub.1 -C.sub.3 hydroxyalkyl groups, and the addition salts of these compounds with pharmaceutically acceptable acids.These compounds are usable in therapy as peripheral vasodilators.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: August 29, 1995
    Assignee: Laboratoire L. Lafon
    Inventor: Louis Lafon
  • Patent number: 5423998
    Abstract: Amino-derivative (poly)peroxycarboxylic acids which have the formula: ##STR1## wherein the symbols have the following meanings: R, R.sub.1, and R.sub.2, which may be equal to or different from one another, represent hydrogen atoms, alkyl groups or groups selected from R, R.sub.1 and R.sub.2, which taken together with the nitrogen atom to which they are linked, give rise to an aliphatic heterocyclic group, all of them being optionally substituted;A represents a (cyclo)alkylene group, an arylene group which may also be condensed with cycloaliphatic groups, a cycloalkylene-alkylene or an alkylene-cycloalkylene group, an arylene-alkylene or an alkylene-arylene group, which may be condensed with cyclo-aliphatic groups, wherein said alkylene group may also be interrupted by --CONR.sub.3 groups, wherein R.sub.3 represents a hydrogen atom or an alkyl or aryl group;X.sup.- represents HSO.sub.4.sup.- or CH.sub.3 SO.sub.3.sup.- ; a process for their preparation; and their use as bleaching agents.
    Type: Grant
    Filed: April 13, 1993
    Date of Patent: June 13, 1995
    Assignee: Ausimont S.r.l.
    Inventors: Carlo Venturello, Claudio Cavallotti
  • Patent number: 5424455
    Abstract: A heterocyclic compound of the formula, ##STR1## wherein A and B are each hydrogen, halogen, alkyl or alkoxy, R.sup.1 is alkylene having upto 6 carbon atoms, X is direct linkage or divalent group such as --O--, --S--and the like, T and U are each hydrogen or alkyl, l is 0 or 1 to 3, Q is 5-, 6- or 7- membered saturated or unsaturated heterocyclic residue, and Y is hydrogen, halogen, alkyl, alkoxy or ##STR2## and B are taken together with each other to form methylene-dioxy, which is useful for dyeing or printing hydrophobic fiber materials with superior dyeability to give a dyed or printed product of a red color excellent in fastness properties, particularly those such as washing fastness.
    Type: Grant
    Filed: July 28, 1993
    Date of Patent: June 13, 1995
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Jun Yamamoto, Yasuyoshi Ueda, Junichi Sekihachi, Yosuke Yamamoto, Takashi Omura
  • Patent number: 5420132
    Abstract: A compound of formula (I): ##STR1## wherein: X represents O, S or H.sub.2,R and R' each represents hydrogen or together form a bond,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the description.useful in the treatment or prevention of disorders involving oxidative processes.
    Type: Grant
    Filed: May 6, 1994
    Date of Patent: May 30, 1995
    Assignee: Adir et Compagnie
    Inventors: Gerald Guillaumet, Gerard Coudert, Valerie Thiery, Gerard Adam, Jean-Guy Bizot-Espiard, Bruno Pfeiffer, Pierre Renard
  • Patent number: 5385930
    Abstract: The invention relates to compounds of the formula I: ##STR1## in which R.sub.1 is as defined in the description, their optical isomers and their addition salts with a pharmaceutically-acceptable acid or base, and medicinal products which are useful for treating Central Nervous System disorders.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: January 31, 1995
    Assignee: Adir et Compagnie
    Inventors: Gerald Guillaumet, Gerard Coudert, Tchao Podona, Beatrice Guardiola-Lemaitre, Pierre Renard, Gerard Adam, Daniel Henri-Caignard
  • Patent number: 5382590
    Abstract: Compounds of formula: ##STR1## in which R.sub.1 represents a hydrogen atom or an alkyl, alkoxycarbonyl or an unsubstituted or substituted phenyl radical,R.sub.2 represents a hydrogen atom or an unsubstituted or substituted alkyl radical,R.sub.3 represents an alkyl, phenylalkyl, indanyl, cycloalkylalkyl or an unsubstituted or substituted phenyl radical, orR.sub.2 and R.sub.3 form a heterocycle together with the nitrogen atom to which they are attached, andR.sub.4 represents an unsubstituted or substituted phenyl radical, a naphthyl, indolyl or quinolyl radical or a phenylamino radical in which the phenyl ring is unsubstituted or substituted, their preparation and medicaments containing them.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: January 17, 1995
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Jean-Dominique Bourzat, Marc Capet, Claude Cotrel, Claude Guyon, Franco Manfre, Gerard Roussel
  • Patent number: 5378713
    Abstract: Substituted thienopyrans and processes for preparing the thienopyrans are disclosed. The thienopyrans are useful as antihypertensive agents; antianginals are peripheral antivasoconstrictive agents.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: January 3, 1995
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Jeffery B. Press, Pauline Sanfilippo, James J. McNally, Robert Falotico
  • Patent number: 5347002
    Abstract: A nitrogen-containing perfluoroalkanoyl peroxide is provided which is represented by the formula: ##STR1## wherein Rf.sub.1 and Rf.sub.2 independently stand for an alkyl group of 1 to 5 carbon atoms, provided that Rf.sub.1 and Rf.sub.2 are joined to each other in one of the three patterns of union, 1) direct union, 2) union through the medium of an oxygen atom or 3) union through the medium of a nitrogen atom to form one of the three rings, i.e. five-membered ring, six-membered ring or seven-membered ring.
    Type: Grant
    Filed: June 21, 1993
    Date of Patent: September 13, 1994
    Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventors: Haruhiko Fukaya, Takashi Abe, Eiji Hayashi, Yoshio Hayakawa
  • Patent number: 5346908
    Abstract: Certain nitrogen-containing cyclohetero cycloalkylaminoaryl compounds are described for treatment of CNS disorders such as cerebral ischemia, psychoses and convulsions. Compounds of particular interest are of the formula: ##STR1## wherein each of R.sup.1, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 is independently selected from hydrido, lower alkyl, benzyl, and haloloweralkyl; wherein each of R.sup.2, R.sup.3 and R.sup.8 through R.sup.11 is independently selected from hydrido, hydroxy, loweralkyl, benzyl, phenoxy, benzyloxy and haloloweralkyl; wherein n is an integer of from four to six; wherein m is an integer of from two to four; wherein A is selected from phenyl, naphthyl, benzothienyl, benzofuranyl and thienyl; wherein any of the foregoing A groups can be further substituted with one or more substituents independently selected from hydrido, hydroxy, loweralkyl, loweralkoxy, halo, haloloweralkyl, amino, monoloweralkylamino and diloweralkylamino; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: September 13, 1994
    Assignees: National Institutes of Health, Brown University
    Inventors: Wayne Bowen, Brian R. de Costa, Celia Dominguez, Xiao-Shu He, Kenner C. Rice