Bicyclo Ring System Having The Hetero Ring As One Of The Cyclos Patents (Class 549/49)
  • Patent number: 5886191
    Abstract: The present application describes amidinoindoles, amidinoazoles, and analogs thereof of formula I: ##STR1## wherein W, W.sup.1, W.sup.2, and W.sup.3 are selected from CH and N, provided that one of W.sup.1 and W.sup.2 is C(C(.dbd.NH)NH.sub.2) and at most two of W, W.sup.1, W.sup.2, and W.sup.3 are N and one of J.sup.a and J.sup.b is substituted by --(CH.sub.2).sub.n --Z--A--B, which are useful as inhibitors of factor Xa or thrombin.
    Type: Grant
    Filed: August 18, 1997
    Date of Patent: March 23, 1999
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Celia Dominguez, Qi Han, Daniel Emmett Duffy, Jeongsook Maria Park, Mimi Lifen Quan, Karen Anita Rossi, Ruth Richmond Wexler
  • Patent number: 5869658
    Abstract: Described are novel photochromic indeno-fused naphthopyran compounds having certain substituents at the 2-position of the pyran ring and an alkoxy group at the number 6 carbon atom. Certain other substituents may also optionally be present at the number 5, 7, 8, 9, 10, 11, 12 or 13 carbon atoms of the compounds. These compounds may be represented by the following graphic formula: ##STR1## Also described are certain novel indeno-fused naphthols which are used to make the novel naphthopyran compounds. Further described are polymeric organic host materials that contain or that are coated with the novel naphthopyran compounds, or combinations thereof with complementary photochromic compounds, e.g., certain other naphthopyrans, benzopyrans, and spiro(indoline)type compounds.
    Type: Grant
    Filed: December 15, 1997
    Date of Patent: February 9, 1999
    Assignee: PPG Industries, Inc.
    Inventors: Jibing Lin, Barry Van Gemert
  • Patent number: 5856339
    Abstract: The present invention provides intermediate compounds and processes for the preparation of compounds of formula I ##STR1## wherein R.sup.1a is --H or --OR.sup.7a in which R.sup.7a is --H or a hydroxy protecting group;R.sup.2a is --H, halo, or --OR.sup.8a in which R.sup.8a is --H or a hydroxy protecting group;R.sup.3 is 1-piperidinyl, 1-pyrrolidino, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidino, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino;n is 2 or 3; andZ is --O-- or --S--;or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: November 3, 1995
    Date of Patent: January 5, 1999
    Assignee: Eli Lilly and Company
    Inventors: Alan David Palkowitz, Kenneth Jeff Thrasher
  • Patent number: 5843972
    Abstract: The present invention relates to certain compounds of the formula (I) the racemic-enantiomeric mixtures and optical isomers of said compounds and the pharmaceutically acceptable salts or prodrugs thereof, depicted below, which are .beta.-adrenergic receptor agonists and accordingly have utility as, inter alia, hypoglycemic and antiobesity agents. More specifically, the compounds of the instant invention are selective agonists of .beta..sub.3 -adrenergic receptor. The invention also relates to methods of use for the compounds and to pharmaceutical compositions containing them. The compounds of the present invention also possess utility for increasing lean meat deposition and/or improving the lean meat to fat ratio in animals, e.g., ungulate animals, companion animals and poultry. The compounds have the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, Y and Z are as defined in the specification.
    Type: Grant
    Filed: March 28, 1997
    Date of Patent: December 1, 1998
    Assignee: Pfizer Inc.
    Inventors: Robert L. Dow, Stephen W. Wright
  • Patent number: 5811427
    Abstract: Certain N-acetonylbenzamides and their use as fungicides are disclosed. The N-acetonylbenzamides disclosed contain a heterocyclic ring fused to an aromatic ring. These compounds are particularly effective against phytopathogenic fungi of the class Oomycetes. Also disclosed is a method for controlling phytopathogenic fungi by applying one or more of the heterocyclic N-acetonylbenzamides of the present invention, optionally with one or more additional fungicidal compounds.
    Type: Grant
    Filed: June 18, 1997
    Date of Patent: September 22, 1998
    Assignee: Rohm and Haas Company
    Inventors: Enrique Luis Michelotti, David Hamilton Young
  • Patent number: 5811582
    Abstract: Dimethyl-(3-aryl-but-3-enyl)-amine compounds, a method of preparing them, and the use of the compounds as pharmaceutical active ingredients are described.
    Type: Grant
    Filed: March 12, 1997
    Date of Patent: September 22, 1998
    Assignee: Gruenenthal GmbH
    Inventors: Helmut Heinrich Buschmann, Wolfgang Werner Alfred Strassburger, Elmar Josef Friderichs, Babette-Yvonne Koegel
  • Patent number: 5767141
    Abstract: Substituted propane derivatives, a process for their preparation and the use of the compounds for treating diseasesPropane derivatives of the formula I ##STR1## in which the radicals have the meanings stated in the description, a process for the preparation of these compounds, their use as pharmaceuticals, and pharmaceutical products are described. Also described are novel intermediates for preparing the compounds of the formula I.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: June 16, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerrit Schubert, Horst Hemmerle, Peter Below, Andreas Herling, Hans-Jorg Burger
  • Patent number: 5756769
    Abstract: A method for producing a propargylamine compound represented by the general formula (I): ##STR1## which comprises reacting a propargyl compound represented by the general formula (II): ##STR2## with an aromatic aldehyde represented by the general formula (III):ArCHO (III)and ammonia to obtain an imine compound represented by the general formula (IV): ##STR3## and hydrolyzing the resultant imine compound. It is to provide a method for producing a propargylamine compound from a propargyl compound by a simple operation without using a special facility, using ammonia as a reaction reagent, without producing a dipropatygylamine compound and a tripropargylamine compound as by-products.
    Type: Grant
    Filed: May 30, 1997
    Date of Patent: May 26, 1998
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Shinzo Seko, Akihiko Nakamura, Motoo Hazama
  • Patent number: 5750728
    Abstract: Aromatic bromomethyl compounds play a major role in the synthesis of active substances. They can be obtained in particularly pure form by the free-radical bromination of aromatic methyl compounds in the solvent chlorobenzene.
    Type: Grant
    Filed: December 11, 1996
    Date of Patent: May 12, 1998
    Assignee: Clariant GmbH
    Inventors: Adalbert Wagner, Heinz-Werner Kleemann, Dieter Regnat, Hans-Jerg Kleiner
  • Patent number: 5726319
    Abstract: There are disclosed certain compounds identified as substituted dipeptide analogs 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 increase the stature of those afflicted with a lack of a normal secretion of natural growth hormone. Growth promoting compositions containing such substituted dipeptide analogs as the active ingredient thereof are also disclosed.
    Type: Grant
    Filed: August 1, 1995
    Date of Patent: March 10, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Peter Lin, William R. Schoen, Judith M. Pisano, Matthew J. Wyvratt
  • Patent number: 5718845
    Abstract: Nonlinear optical compounds which contain a heteroaromatic ring and may further comprise a tricyanovinyl group attached to the heteroaromatic ring.
    Type: Grant
    Filed: January 18, 1995
    Date of Patent: February 17, 1998
    Assignee: Enichem S.p.A.
    Inventors: Kevin J. Drost, Pushkara Rao Varanasi, Kwan-Yue Alex Jen, Michael Anthony Drzewinski
  • Patent number: 5716979
    Abstract: The invention concerns tachykinin antagonists. The compounds are nonpeptides which have utility in treating disorders mediated by tachykinins. Such disorders are respiratory, inflammatory, gastrointestinal, ophthalmic, allergies, pain, vascular, diseases of the central nervous system, and migraine. Methods of preparing compounds and novel intermediates are also included.The compounds are expected to be especially useful in asthma and rheumatoid arthritis.
    Type: Grant
    Filed: October 8, 1996
    Date of Patent: February 10, 1998
    Assignee: Warner-Lambert Company
    Inventors: David Christopher Horwell, William Howson, Martyn Clive Pritchard, Edward Roberts, David Charles Rees
  • Patent number: 5712390
    Abstract: The present invention provides processes for preparing compounds of formula I ##STR1## and for preparing compounds of formula VII ##STR2## Also provided are processes for preparing compounds of formula VII in addition to intermediates of formula IX ##STR3## wherein R.sup.1' is --OH, or --OR.sup.3, in which R.sup.3 is a hydroxy protecting group; andZ is bromo, iodo, triflate, or --B(OH).sub.2.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: January 27, 1998
    Assignee: Eli Lilly and Company
    Inventors: Kenneth L. Hauser, Alan D. Palkowitz, Daniel J. Sall, Kenneth J. Thrasher
  • Patent number: 5686471
    Abstract: A compound having the structure: ##STR1## wherein (a) n is from about 1 to about 3;(b) X is selected from the group consisiting of O, S, SO, or SO.sub.2 ;(c) Y is independently hydrogen or straight, branched or cyclic alkyl or aralkyl having from 1 to about 3 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) R.sub.1 and R.sub.2 are each independently hydrogen or straight, branched or cyclic alkyl, unsubstituted or substituted, carboxyl, carboxamido, alkoxycarbonyl or alkylcarbonyl; and(f) Het is a heteroaryl group comprising one or more rings containing from about 5 to about 8 atoms in the rings and wherein at least one ring has at least one heteroatom selected from O, N, or S,pharmaceutical compositions comprising such compounds, and methods of treating inflammation or pain using such compounds.
    Type: Grant
    Filed: February 1, 1996
    Date of Patent: November 11, 1997
    Assignee: The Procter & Gamble Company
    Inventors: Zhuoliang Chen, John Michael Janusz
  • Patent number: 5684152
    Abstract: Carboxy-peptidyl compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophobic epidermolysis bullosa, coronary thrombosis associated with atherosclerotic plaque rupture, and aneurysmal aortic disease. This invention relates to a process of making the carboxy-peptidyl compounds of formula I.
    Type: Grant
    Filed: September 19, 1996
    Date of Patent: November 4, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Mitree M. Ponpipom, William K. Hagmann
  • Patent number: 5672583
    Abstract: Novel Carboxy-peptidyl compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophobic epidermolysis bullosa, coronary thrombosis associated with atherosclerotic plaque rupture, and aneurysmal aortic disease. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also have utility as a means for birth control by preventing ovulation or implantation.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: September 30, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Kevin Chapman, William Hagmann, Philippe Durette, Craig Esser, Ihor Kopka, Charles Caldwell
  • 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: 5620998
    Abstract: The invention relates to N-acyl-N-heterocyclylalkylamino acids of the formula ##STR1## wherein Y.sub.1 is O, S or N(R) and R is hydrogen or C.sub.1 -C.sub.7 alkyl;X.sub.1 is --CO-- or --S(O).sub.m -- and the index m is 0, 1 or 2;one of the variables X.sub.2 and X.sub.4 is C.sub.1 -C.sub.4 alkylene and the other of the variables X.sub.2 and X.sub.4 is a bond; or each of the variables X.sub.2 and X.sub.4 is a bond;X.sub.3 is C.sub.3 -C.sub.7 cycloalkylidene or the structural element --C(X.sub.a)(X.sub.b)-- and X.sub.a is hydrogen or C.sub.1 -C.sub.7 alkyl and X.sub.b is C.sub.1 -C.sub.7 alkyl;and the rings A, B and C, with the exception of the substituents indicated in the formula, and also aromatic substituents are, independently of one another, unsubstituted or mono- or poly-substituted by substituents selected from the group consisting of halogen, C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.7 alkoxy, C.sub.2 -C.sub.7 alkenyloxy, phenoxy, benzyloxy, trifluoromethyl and S(O).sub.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 15, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Tibur Schmidlin, Paul Zbinden, Peter B uhlmayer
  • 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: 5607624
    Abstract: A process for the preparation of compounds of formula I ##STR1## wherein the general symbols are as defined in claim 1, which comprises reacting a compound of formula III ##STR2## wherein the general symbols are as defined in claim 1, with a compound of formula IV[H].sub.n --R.sub.1 (IV).
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: March 4, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Nesvadba, Samuel Evans, Ralf Schmitt
  • 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: 5605896
    Abstract: This invention provides bicyclic heterocyclic derivatives and their pharmaceutically acceptable salts useful for the treatment of hypertension, urethral and lower urinary tract contractions, and other disorders. The compounds are also useful for binding .alpha..sub.1 -adrenergic and 5HT.sub.1A serotonergic receptors, in vitro or in vivo.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: February 25, 1997
    Assignee: Recordati S.A., Chemical and Pharmaceutical Company
    Inventors: Amedeo Leonardi, Gianni Motta, Carlo Riva, Rodolfo Testa
  • Patent number: 5557006
    Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth fire disclosed.
    Type: Grant
    Filed: April 20, 1995
    Date of Patent: September 17, 1996
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Hamer, Brian S. Freed, Gregory H. Merriman
  • Patent number: 5554641
    Abstract: The small nonpeptides of the instant invention are tachykinin antagonists. The compounds are highly selective and functional NK.sub.3 antagonists expected to be useful in the treatment of pain, depression, anxiety, panic, schizophrenia, neuralgia, addiction disorders, inflammatory diseases, gastrointestinal disorders, vascular disorders, and neuropathological disorders.
    Type: Grant
    Filed: March 20, 1995
    Date of Patent: September 10, 1996
    Inventors: David C. Horwell, Martyn C. Pritchard, Jennifer Raphy
  • Patent number: 5550247
    Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.
    Type: Grant
    Filed: April 20, 1995
    Date of Patent: August 27, 1996
    Assignee: Hoechst Roussel Pharmaceuticals Inc.
    Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Harner, Brian S. Freed, Gregory H. Merriman
  • Patent number: 5534640
    Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: July 9, 1996
    Assignee: Hoechst Roussel Pharmaceuticals Inc.
    Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Hamer, Brian S. Freed, Gregory H. Merriman
  • Patent number: 5525736
    Abstract: A process for the production of a 5-7 membered ring cyclic sulfonium salt compound, including a 5-7 membered ring cyclic sulfonium salt compound having a non-nucleophilic anion, is described. Members of the latter group are potentially useful as initiators for cationic polymerizations. The process comprises reacting a 1.4-, 1.5-, or 1.6-diol compound or a 5-7 membered ring cyclic ether compound with a mercapto compound and a strong protonic acid yielding the cyclic sulfonium salt compound. Some compounds described are also novel compounds per se.
    Type: Grant
    Filed: February 23, 1995
    Date of Patent: June 11, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Jan-Erik Nystrom, Per Engelhardt, Katarina Beierlein, Mikael Sellen, Bjorn Elman, Jan Vagberg, Martin Nylof
  • Patent number: 5514289
    Abstract: Novel dihydrobenzothiophenes prepared via condensation of arylthiols and carbonyl or epoxide containing reagents have been found to be effective antioxidant and antiwear additives in lubricant applications. These additives are made from relatively low cost mercaptans and carbonyl compounds in a one-step high yield reaction.
    Type: Grant
    Filed: April 13, 1995
    Date of Patent: May 7, 1996
    Assignee: Mobil Oil Corporation
    Inventors: Halou Oumar-Mahamat, Andrew G. Horodysky, Andrew Jeng
  • Patent number: 5514718
    Abstract: Compounds of formula (I), and salts and prodrugs thereof ##STR1## wherein Q.sup.1 is halo substituted phenyl; naphthyl; indolyl; benzthiophenyl; benzofuranyl; benzyl; or fluorenyl;. . is an optional covalent bond;one of X and Y is H and the other is hydroxy or C.sub.1-6 alkoxy, or X and Y are together .dbd.O or .dbd.NOR.sup.5 ;R.sup.1 and R.sup.2 are H; C.sub.1-6 alkyl optionally substituted by hydroxy, cyano, COR.sup.c, CO.sub.2 R.sup.c, CONR.sup.c R.sup.d, or NR.sup.c R.sup.d (where R.sup.c and R.sup.d are H, C.sub.1-6 alkyl or phenyl(C.sub.0-4 alkyl) optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halo and trifluoromethyl); phenyl(C.sub.1-4 alkyl) (optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halo or trifluoromethyl); COR.sup.c ; CO.sub.2 R.sup.c ; CONR.sup.c R.sup.d ; COC.sub.1-6 alkylNR.sup.c R.sup.d ; CONR.sup.c COOR.sup.d ; or SO.sub.2 R.sup.c ;R.sup.3 is H, C.sub.1-6 alkyl or C.sub.2-6 alkenyl; andR.sup.4 is phenyl optionally substituted by C.sub.1-6 alkyl, C.sub.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: May 7, 1996
    Assignee: Merck, Sharp & Dohme Limited
    Inventors: Richard T. Lewis, Kevin J. Merchant, Angus M. MacLeod
  • Patent number: 5510358
    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 treating endometriosis.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: April 23, 1996
    Assignee: Eli Lilly and Company
    Inventor: Alan D. Palkowitz
  • Patent number: 5510498
    Abstract: The present invention provides compounds of formula II ##STR1## wherein R.sup.1a is --H or --OR.sup.7 in which R.sup.7 is a hydroxy protecting group;R.sup.2a is --H, halo, or --OR.sup.8 in which R.sup.8 is a hydroxy protecting group, providing when Z is --S--, R.sup.2a is not halo;R.sup.6 is --H or a hydroxy protecting group which can be selectively removed; andZ is --O-- or --S--;or a pharmaceutically acceptable salt thereof, which are useful intermediates for the preparation of biologically active compounds.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: April 23, 1996
    Assignee: Eli Lilly and Company
    Inventor: Alan D. Palkowitz
  • Patent number: 5510357
    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, inter alia, alleviating the symptoms of post menopausal syndrome and hormonally-dependent cancer, particularly breast cancer.
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: April 23, 1996
    Assignee: Eli Lilly and Company
    Inventor: Alan D. Palkowitz
  • Patent number: 5482942
    Abstract: This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: January 9, 1996
    Assignee: American Home Products Corporation
    Inventors: Richard M. Soll, Paul J. Dollings
  • Patent number: 5480902
    Abstract: There are provided fungicidal thienyl- and furylpyrrole compounds of formula I ##STR1## Further provided are compositions and methods comprising those compounds for the protection of plants from fungal infestation and disease.
    Type: Grant
    Filed: August 31, 1993
    Date of Patent: January 2, 1996
    Assignee: American Cyanamid Company
    Inventors: Roger W. Addor, Joseph A. Furch, III, Laurelee A. Duncan
  • Patent number: 5443940
    Abstract: Disclosed herein is an optical recording material containing a photochromic compound which is expressed in the following general formula (I): ##STR1## where A represents an oxygen atom or a substituted or unsubstituted nitrogen atom, R.sub.1 represents an alkoxy group, R.sub.2 to R.sub.5 represent substituents such as a hydrogen atom, a halogen atom, a hydroxy group, a substituted or unsubstituted alkyl group and the like respectively, and B represents a substituted or unsubstituted thiophene ring, benzothiophene ring, pyrrole ring or indole ring.
    Type: Grant
    Filed: April 14, 1993
    Date of Patent: August 22, 1995
    Assignees: Sanyo Electric Co., Ltd., Kobe Natural Products & Chemicals Co., Ltd.
    Inventors: Fumio Tatezono, Toshio Harada, Masahiro Irie, Meguru Ohara
  • Patent number: 5440049
    Abstract: A compound of the formula: ##STR1## wherein R.sup.11 is hydrogen, lower alkyl, haloloweralkyl, lower alkenyl, lower alkynyl or cycloalkyl and R.sup.21 is a group selected from the group consisting of: ##STR2## wherein R.sup.3 -R.sup.5, R.sup.31, R.sup.32, R.sup.41, R.sup.42 and R.sup.51 are as defined herein, and W is chlorine or bromine, is prepared by reacting a compound of the formula:Z--CH.sub.2 --CH.dbd.CH--W (I)wherein W is as defined above and Z is a leaving group, with an amine of the formula: ##STR3## wherein R.sup.11 and R.sup.21 are as defined above.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: August 8, 1995
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • Patent number: 5436354
    Abstract: (E)-N-(3-Chloro-2-propenyl)-N-methyl-1naphthylenemethanamine and (E)-3-chloro-N-(3-chloro-2-propenyl)-N-methylbenzo[b]thiophene-7-methanami ne which are useful as intermediates in the production of enyne compounds which exhibit squalene epoxidase inhibiting activity and anti-Eumycetes activity.
    Type: Grant
    Filed: December 13, 1994
    Date of Patent: July 25, 1995
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • Patent number: 5420164
    Abstract: A cycloalkylurea compound of the formula (I): ##STR1## wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof, which compound inhibits ACAT and is useful as hypolipidemic and antiatherosclerotic medicine.
    Type: Grant
    Filed: May 3, 1993
    Date of Patent: May 30, 1995
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Tadashi Mishina, Kanou Harada, Joji Yasuoka, Hidenobu Kushuhara, Noriyoshi Izumi
  • Patent number: 5420300
    Abstract: The subject of the invention is 2-(1-bromoethyl)benzo[b]thiophene of formula: ##STR1## as well as a process for the preparation thereof, characterised in that 2-ethylbenzo[b]thiophene is reacted, in a solvent, with a brominating agent in the presence of a free radical initiator, which provides the desired compound, and the use thereof in the preparation of 2-(1-(benzyloxyamino)ethyl)benzo[b]thiophene and of N-hydroxy-N-{1-(benzo[b]thien-2-yl)ethyl}urea.No figure.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: May 30, 1995
    Assignee: Elf Sanofi
    Inventor: Jean-Robert Dormoy
  • Patent number: 5391772
    Abstract: Described is a process for converting an alcohol to an azide with S.sub.N 2 inversion using a phosphoryl azide, e.g. diphenylphosphoryl azide (DPPA). Good yields of azide in high enantiomeric excess can be achieved specifically for benzylic alcohols and alpha-hydroxy alkyl esters. The process is carried at preferably room temperature in an inert dry aprotic solvent, e.g. toluene, and in the presence of a proton acceptor, e.g. 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to afford high yields of high enantiomeric purities.
    Type: Grant
    Filed: July 8, 1993
    Date of Patent: February 21, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Andrew S. Thompson, Edward J. J. Grabowski
  • Patent number: 5372734
    Abstract: Alkylated benzothiophenes or dibenzothiophenes are high-temperature stable lubricant fluids having extreme pressure and antiwear properties, additive solubility and inherent EP/antiwear properties. These novel fluids may also be used as additives in other lubricant fluids.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: December 13, 1994
    Assignee: Mobil Oil Corporation
    Inventors: Derek A. Law, Carleton N. Rowe, Leslie R. Rudnick
  • Patent number: 5359091
    Abstract: A compound of the formula: ##STR1## wherein R.sup.11 is hydrogen, lower alkyl, haloloweralkyl, lower alkenyl, lower alkynyl or cycloalkyl; R.sup.21 is a group of the formula: ##STR2## wherein each of R.sup.3, R.sup.31, and R.sup.32 which may be the same or different, is hydrogen or lower alkyl, each of R.sup.4, R.sup.5, R.sup.41 and R.sup.51, which may be the same or different, is hydrogen, halogen, hydroxyl, lower alkyl or lower alkoxy, R.sup.42 is hydroxyl, halogen, R.sup.8 --O--, or R.sup.6 --X--Y-- wherein R.sup.6 is phenyl or thienyl which may have one or two substituents each of X and Y, which may be the same or different, is oxygen, sulfur, carbonyl, --CHR.sup.8 -- or --NR.sup.b, or X and Y together form a vinylene group or an ethynylene group, provided that when either one of X and Y is oxygen, sulfur or --NR.sup.b, the other is carbonyl or --CHR.sup.a, and R.sup.
    Type: Grant
    Filed: November 18, 1993
    Date of Patent: October 25, 1994
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • Patent number: 5328927
    Abstract: Compounds of formula (I), and salts and prodrugs thereof ##STR1## wherein Q.sup.1 is halo substituted phenyl; naphthyl; indolyl; benzthiophenyl; benzofuranyl; benzyl; or fluorenyl;. . is an optional covalent bond;one of X and Y is H and the other is hydroxy or C.sub.1-6 alkoxy, or X and Y are together .dbd.0 or .dbd.NOR.sup.5 ;R.sup.1 and R.sup.2 are H; C.sub.1-6 alkyl optionally substituted by hydroxy, cyano, COR.sup.c, CO.sub.2 R.sup.c, CONR.sup.c R.sup.d, or NR.sup.c R.sup.d (where R.sup.c and R.sup.d are H, C.sub.1-6 alkyl or phenyl(C.sub.0-4 alkyl) optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halo and trifluoromethyl); phenyl(C.sub.1-4 alkyl) (optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halo or trifluoromethyl); COR.sup.c ; CO.sub.2 R.sup.c ; CONR.sup.c R.sup.d ; COC.sub.1-6 alkylNR.sup.c R.sup.d ; CONR.sup.c COOR.sup.d ; or SO.sub.2 R.sup.c ;R.sup.3 is H, C.sub.1-6 alkyl or C.sub.2-6 alkenyl; andR.sup.4 is phenyl optionally substituted by C.sub.1-6 alkyl, C.sub.
    Type: Grant
    Filed: February 24, 1993
    Date of Patent: July 12, 1994
    Assignee: Merck Sharpe & Dohme, Ltd.
    Inventors: Richard T. Lewis, Kevin J. Merchant, Angus M. MacLeod
  • Patent number: 5302724
    Abstract: This invention provides certain sulfonamide compounds, formulations and method of use of certain sulfonamide compounds in treating susceptible neoplasms.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: April 12, 1994
    Assignee: Eli Lilly and Company
    Inventors: J. Jeffry Howbert, Fariborz Mohamadi, Michael M. Spees
  • Patent number: 5296612
    Abstract: A process for producing an enyne derivative, and intermediate, which is useful for preparing compounds showing strong inhibiting activities against squalane epoxidase of Eumycetes and strong anti-cholesterol activities. The process comprises reacting a compound of the formula: ##STR1## wherein W is a halogen atom, with an acetylene derivative, in the presence of a palladium catalyst, to obtain a compound of the formula: ##STR2## and, if necessary, N-alkylating this compound.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: March 22, 1994
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • Patent number: 5292894
    Abstract: A process for the preparation of benzo[b]thiophenes of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 independently denote hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro, cyano, halo, C.sub.1 -C.sub.4 alkylcarbonyl, benzoyl, C.sub.1 -C.sub.4 alkylcarbonylamino, benzoylamino,N-(C.sub.1 -C.sub.4 alkyl)phenylamino, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, phenylsulfonyl, aminosulfonyl, aminocarbonyl, C.sub.1 -C.sub.4 phenylalkyl and nitrobenzyl or R.sup.1 +R.sup.2 or R.sup.2 +R.sup.3 or R.sup.3 +R.sup.4 denote a butadienediyl chain optionally substituted by R.sup.1 to R.sup.4, in whicha) thiophenols of the general formula II ##STR2## in which the substituents R.sup.1 to R.sup.4 have the aforementioned meanings, are reacted with chloroacetaldehyde at a temperature ranging from 0.degree. to 150.degree. C. andb) the resulting (arylthio)acetaldehydes of the general formula III ##STR3## in which the substituents R.sup.
    Type: Grant
    Filed: February 17, 1993
    Date of Patent: March 8, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ebel, Juergen Schroeder
  • Patent number: 5266705
    Abstract: A process for production of 2-acetylbenzo[b]thiophene represented by the formula (I): ##STR1## comprising the steps of: (1) reacting 2-halogenobenzaldehyde represented by the formula (II): ##STR2## wherein X represents a halogen atom, with a compound represented by the formula (III):H.sub.i S.sub.j M.sub.kwherein M represents an alkali metal, i represents zero or 1, j represents an integer of at least 1, and k represents an integer of 1 or 2, and preferably also with sulfur; and(2) reacting the reaction product with a monohalogenoacetone represented by the formula (IV) ##STR3## wherein X.sup.1 represents a halogen atom.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: November 30, 1993
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Naoto Yazawa, Yoshinori Saito, Hidetaka Hiyoshi
  • Patent number: 5258360
    Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, wherein R.sup.1 and R.sup.2, which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, --NR.sup.3 --, or --CR.sup.4 R.sup.5 --; X, Y and Z.sup.1, which are the same or different, are, for example, hydrogen, halogen, hydroxy, optionally substituted alkyl, cycloalkyl or aryl among other possible substituents or X and Y when they are in adjacent positions on the ring optionally form a fused ring; and R, R.sup.3 -R.sup.12 are, for example, hydrogen or optionally substituted alkyl among other possible substituents provided R.sup.4 and R.sup.5 are not both hydrogen. The compounds are useful in agriculture, especially as fungicides but also as insecticides and plant growth regulators.
    Type: Grant
    Filed: July 21, 1992
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul deFraine, Christopher R. A. Godfrey, Kevin Beautement
  • Patent number: RE34770
    Abstract: Amine derivatives having the general formula (I): ##STR1## wherein X is selected from the group consisting of ##STR2## Y is selected from the group consisting of ##STR3## R.sup.1 is hydrogen atom or an alkyl group; R.sup.2 is hydrogen atom or an alkyl group; R.sup.3 is hydrogen atom, a halogen atom or an alkyl group; R.sup.4 is hydrogen atom, an alkyl group, a cycloalkyl group, a halogenated alkyl group or a halogen atom; R.sup.5 is hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, nitro group or hydroxy group; R.sup.5 is attached to an arbitrary position of X, and R.sup.3 or R.sup.4 is attached to an arbitrary position of Y.The amine derivatives (I) are useful as fungicides.
    Type: Grant
    Filed: May 21, 1993
    Date of Patent: November 1, 1994
    Assignee: Kaken Pharmaceutical Co., Ltd.
    Inventors: Tetsuya Maeda, Toshiyuki Yamamoto, Mituo Takase, Kazuya Sasaki, Tadashi Arika, Mamoru Yokoo, Rieko Hashimoto, Kouji Amemiya, Sakae Koshikawa