Ortho Fused Patents (Class 560/119)
  • Patent number: 5200530
    Abstract: The invention relates to a new process for the reduction of 15-keto carbacyclin intermediates in the presence of cerium(III) Salts.
    Type: Grant
    Filed: July 31, 1991
    Date of Patent: April 6, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Dahl, Gabriela Buttner, Dieter Peschel
  • Patent number: 5190964
    Abstract: 5-fluorocarbacyclin derivatives of the Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH orA is --CH.sub.2 --CH.sub.2 --, trans --CH.dbd.CH-- or --C.tbd.C--,W is a free or functionally modified hydroxymethylene group or free or functionally modified ##STR2## in which the OH group can be in the .alpha.-- or .beta.-position, D is ##STR3## a C.sub.1-10 -aliphatic group (e.g., alkyl or alkenyl) which optionally can be substituted by fluorine atoms,n is 1, 2 or 3,E is a direct bond, --C.tbd.C-- or --CR.sub.6 .tbd.CR.sub.7 -- in which R.sub.6 represents a hydrogen atom or an alkyl group with 1-5 atoms and R.sub.7 represents a hydrogen atom, a halogen atom or an alkyl group with 1-5 C atoms,R.sub.4 is alkyl, cycloalkyl or optionally substituted aryl or a heterocyclic group,R.sub.5 is a free or functionally modified hydroxy groupand, when R.sub.2 is a hydrogen atom, its salts with physiologically compatible bases,have valuable pharmacological properties.
    Type: Grant
    Filed: February 15, 1990
    Date of Patent: March 2, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Martin Haberey, Claus-Steffen Sturzebecher, Michael-Harold Town
  • Patent number: 5180589
    Abstract: A pharmaceutical composition is provided which has excellent stability, when dispersed in water has a pH of at least about 9, and includes a medicament which is sensitive to a low pH environment such as pravastatin, one or more fillers such as lactose and/or microcrystalline cellulose, one or more binders, such as microcrystalline cellulose (dry binder) or polyvinylpyrrolidone (wet binder), one or more disintegrating agents such as croscarmellose sodium, one or more lubricants such as magnesium stearate and one or more basifying agents such as magnesium oxide.
    Type: Grant
    Filed: May 20, 1991
    Date of Patent: January 19, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Yatindra M. Joshi, Pierina Chiesa, Nemichand B. Jain
  • Patent number: 5177104
    Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof have been found to possess activity as cell-selective HMG-CoA reductase inhibitors, thus making them useful as antihypercholesterolemic agents. In the above formula, ##STR2## R.sup.1 is hydrogen, alkyl, cycloalkyl, aryl or arylalkyl; and R.sup.2 is hydrogen, alkyl, ammonium, or alkali metal.
    Type: Grant
    Filed: April 3, 1990
    Date of Patent: January 5, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Ravi K. Varma, Sam T. Chao, Eric M. Gordon
  • Patent number: 5175338
    Abstract: An isocarbacyclin derivative represented by the following formula [VII'] ##STR1## wherein A represents, a hydrocarbylcarboxylate group, a carboxymethoxycarbonyl group, an amide group, an acyloxymethyl group or a hydroxymethyl group; R.sup.4 represents H, a methyl group or a vinyl group; R.sup.5 represents a (substituted)alkyl group, a phenyl group, a phenoxy group or a cycloalkyl group; R.sup.e22 and R.sup.e32 represent H or a hydroxyprotecting group; n is 0 or 1;and a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: December 29, 1992
    Assignee: Teijin Limited
    Inventors: Atsuo Hazato, Toshio Tanaka, Noriaki Okamura, Kiyoshi Bannai, Seizi Kurozumi, Masaaki Suzuki, Ryoji Noyori
  • Patent number: 5173487
    Abstract: Antihypercholesterolemic activity, due to competitive inhibition of HMG CoA reductase, is exhibited by a compound of the formula ##STR1## m is 0 to 3; R is selected from:(1) alkyl;(2) substituted alkyl;(3) alkoxy;(4) alkenyl;(5) cycloalkyl;(6) phenyl; and(7) substituted aryl; andR.sup.1 and R.sup.2 are as defined in the specification.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: December 22, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jeffrey O. Saunders, Eric M. Gordon
  • Patent number: 5162353
    Abstract: The invention relates to carbacyclin derivatives with general formula I: ##STR1## in which Y.sub.1 stands for the radical --CH.sub.2 --X--(CH.sub.2).sub.n --R.sub.1 or the radical ##STR2## n, 1 or 3, R.sub.1, the radical ##STR3## the radical ##STR4## R.sub.9 stands for the radical --(CH.sub.2).sub.m --R.sub.6 or the radical --(CH.sub.2).sub.m-o --[Z.sub.1 --(CH.sub.2).sub.m-p ].sub.x --[Z.sub.2 --(CH.sub.2).sub.m-q ].sub.y --R.sub.6,m=2-20,o, p, and q are less than or equal to 19,x, y=0, 1 or 2,Z.sub.1 stands for a cis--CH.dbd.CH group, a trans--CH.dbd.CH group of a --C.dbd.C group, and each of these groups must be separated at least by a methylene group from the C-9 carbon atom of the carbacyclin bicyclic compound,Z.sub.2 stands for oxygen, sulfur, an NH or an N methyl group,R.sub.6 stands for amino, methylamino, hydroxy, carboxy or mercapto,X an oxygen atom or a methylene group,Y.sub.2 hydrogen or fluorine,A a --CH.sub.2 --CH.sub.2, trans--CH.dbd.CH or --C.dbd.
    Type: Grant
    Filed: August 21, 1990
    Date of Patent: November 10, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher
  • Patent number: 5159104
    Abstract: A process is disclosed, for the formation of simvastatin, which comprises the sequential acylation of a diol lactone to form a bis acylated intermediate followed by selective deacylation and lactone ring closure to form simvastatin.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: October 27, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Rebecca L. Dabora, Gregory L. Tewalt
  • Patent number: 5157042
    Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, ##STR2## or a heterocyclic residue; or R.sub.1 is NHR.sub.3 wherein R.sub.3 is an acid residue (acyl) or R.sub.2 ;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR3## wherein the OH-group can be in the .alpha.- or .beta.-position; D is ##STR4## a straight-chain, saturated aliphatic group of 1-10 carbon atoms; or a branched, saturated or straight-chain or branched, unsaturated aliphatic group of 2-10 carbon atoms; all of which are substituted by fluorine atoms;n is 1, 2, or 3;E is a direct bond, --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 is hydrogen or alkyl of 1-5 carbon atoms and R.sub.7 is hydrogen, halogen or alkyl of 1-5 carbon atoms;R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group; andR.sub.
    Type: Grant
    Filed: June 10, 1991
    Date of Patent: October 20, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Gerda Mannesmann, Michael H. Town
  • Patent number: 5155229
    Abstract: Derivatives of pravastatin are provided which are useful in inhibiting cholesterol biosynthesis and in preparing radiolabeled compounds useful in the radioimmunoassay (RIA) of pravastatin and derivatives thereof. The pravastatin derivatives have the structure ##STR1## wherein R is hydroxy, lower alkylamine, arylamine, arylalkylamine or heterocyclic alkylamine such as histamine, tyramine, O-benzyltyramine, methyl tyrosinate as well as iodinated derivatives thereof.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: October 13, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Richard A. DiPietro, Jan-I Tu, Noor Z. Turabi
  • Patent number: 5153124
    Abstract: Derivatives of ML-236B carboxylic acid, its salts and esters and corresponding lactone have a hydroxy group at the 3"-position and optionally also at the 6'-position. These derivatives may be prepared by the enzymatic hydroxylation of a corresponding ML-236B compound employing an enzyme produced by a microorganism of the genus Streptomyces or Amycolata, especially Streptomyces sp. SANK 62285, Streptomyces sp. SANK 62385, Streptomyces sp. SANK 62485, Streptomyces sp. SANK 62585, Amycolata autotrophica SANK 62781, Amycolata autotrophica subsp. canberrica SANK 62882 or Amycolata autotrophica subsp. amethystina SANK 62981. These derivatives have the ability to inhibit cholesterol biosynthesis.
    Type: Grant
    Filed: August 11, 1989
    Date of Patent: October 6, 1992
    Assignee: Sankyo Company Limited
    Inventors: Kouhei Furuya, Takao Okazaki, Yoshio Tsujita, Seigo Iwado, Kiyoshi Hamano, Masao Kuroda, Jun Yoshikawa, Toshiaki Iwai, Kunio Nakano
  • Patent number: 5130306
    Abstract: Novel HMG-CoA reductase inhibitors are useful as antihypercholesterolemic agents and are represented by structural formulae (I) or (II): ##STR1## wherein position 5 of the polyhydronaphthyl ring is singly or doubly bonded to oxygen or incorporated into a C.sub.3-7 carbocyclic ring.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: July 14, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Mark E. Duggan, George D. Hartman
  • Patent number: 5116870
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors are useful as antihypercholesterolemic agents and are represented by the following general structural formula (II): ##STR1##
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: May 26, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Robert L. Smith, Wasyl Halczenko, George D. Hartman, Gerald E. Stokker, Edward S. Inamine, Otto D. Hensens, David R. Houck, Ta J. Lee
  • Patent number: 5117037
    Abstract: A cis-bicyclo[4.3.0]non-2-ene derivative of the formula: ##STR1## wherein R is a hydrogen atom, or a protecting group for a hydroxyl group, R.sup.1 is a hydrogen atom, A C.sub.1 -C.sub.12 straight or branched chain alkyl group, a substituted or unsubstituted phenyl group, a C.sub.6 -C.sub.12 aralkyl group containing a condensed aromatic ring or an aromatic hetero ring, or 1 equivalent of a cation, A is --CH.dbd.CH--CH.sub.2 --, or --CH.sub.2 --CH.sub.2 --O--, R.sup.2 is a C.sub.3 -C.sub.10 straight or branched chain alkyl group, a C.sub.1 -C.sub.3 alkyl group substituted by an aryloxy group which may be substituted, a C.sub.3 -C.sub.12 straight or branched chain alkenyl group, a C.sub.3 -C.sub.8 straight or branched chain alkynyl group, a C.sub.1 -C.sub.3 alkyl group substituted by a phenyl or phenoxy group which may be substituted, by a C.sub.1 -C.sub.6 alkoxy group or by a C.sub.5 -C.sub.8 cycloalkyl group, R.sup.3 is a hydrogen atom, a methyl group, or a vinyl group, and X is a halogen atom.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: May 26, 1992
    Assignee: Sagami Chemical Research Center Toa Eiyo Ltd.
    Inventors: Masakatsu Shibasaki, Takahashi Atsuo, Tuyoshi Aoki, Hiroyasu Sato, Shin-ichi Yamada, Michiko Kudo, Takaji Yamaguchi, Kentaro Kogi, Sen-ichi Narita
  • Patent number: 5112857
    Abstract: This invention relates to compounds of formulae I and II ##STR1## which are metabolites of tetrahydrosimvastatin and 5-hydroxy-tetrahydrosimvastatin and which are HMG-CoA reductase inhibitors.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: May 12, 1992
    Assignee: Merck & Co., Inc.
    Inventor: Stanley Vickers
  • Patent number: 5102911
    Abstract: HMG-CoA reductase inhibitors of formulae (I) and (II) are disclosed.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: April 7, 1992
    Assignee: Merck & Co, Inc.
    Inventors: Ta J. Lee, Wilbur J. Holtz
  • Patent number: 5093490
    Abstract: The invention relates to a process for the production of (+)-bicyclo[3.3.0]octan-3-one-2 carboxylic acid steroid esters of formula I ##STR1## in which X means oxygen or the radicals --O--(CH.sub.2).sub.n --O-- or --O--CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --O--,n means 2 or 3R.sub.2 means hydrogen or methyl,Y means the radicals X or X.sub.1,X.sub.1 means the radicals OCH.sub.3 or OCOR.sub.3,R.sub.3 means methyl, ethyl, phenyl, benzyl or pivalyl and the radical ##STR2## the radicals ##STR3## and X and X.sub.1 have the meanings indicated above, characterized in that D,L-bicyclo[3.3.0]octan-3-one-2 carboxylic acid esters of formula II ##STR4## in which X has the meaning indicated above and R is an alkyl group with 1-4 carbon atoms, with optically active steroids with a free 17'beta hydroxy group of formula III ##STR5## in which R.sub.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: March 3, 1992
    Assignee: Schering Aktiengesellschaft
    Inventor: Helmut Vorbrueggen
  • Patent number: 5091431
    Abstract: Compounds having an optionally-substituted purine derivative portion and a carbobicyclic or heterobicyclic portion, which compounds are useful as phosphodiesterase inhibitors, are disclosed. Also disclosed are intermediates, methods for making the inhibitors, pharmaceutical compositions and methods for treating hypertension using the compounds.
    Type: Grant
    Filed: July 18, 1990
    Date of Patent: February 25, 1992
    Assignee: Schering Corporation
    Inventors: Deen Tulshian, Ronald J. Doll
  • Patent number: 5089523
    Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable salts and tautomeric mixtures thereof possess activity as HMg-CoA reductase inhibitors, thus making them useful as antihypercholesterolemic agents. In the above formula,Z is ##STR2## R.sup.1 and R.sup.2 are each independently fluoro or hydrogen, except that at least one of R.sup.1 and R.sup.2 is fluoro;R.sup.3 is hydrogen, alkyl, cycloalkyl, aryl or arylalkyl; andR.sup.4 is hydrogen, alkyl, ammonium, alkylammonium, or alkali metal.
    Type: Grant
    Filed: May 11, 1990
    Date of Patent: February 18, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Ravi K. Varma, Sam T. Chao
  • Patent number: 5084592
    Abstract: Azulenesquaric acid dyes of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each have specified meanings are prepared from azulene derivatives of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each have specified meanings as intermediates, and used in an optical recording medium.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: January 28, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Schrott, Peter Neumann, Sibylle Brosius, Helmut Barzynski, Klaus D. Schomann, Harald Kuppelmaier
  • Patent number: 5053526
    Abstract: Disclosed is a pharmaceutical having circulation ameliorating effect and antiulcer effect containing a prostaglandin I.sub.2 analogue represented by the formula shown below or a non-toxic salt of its salt or a cyclodextrin inclusion compound thereof as the effective ingredient: ##STR1## wherein R.sup.1 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 4 to 7 carbon atoms or a phenyl group; A represents a pentyl group, a cyclopentyl group, a cyclohexyl group, a 1-methyl-3-hexynyl group, a 2-methyl-3-hexynyl group, a 1-methylhexyl group, a 2-phenethyl group, a 1,1-dimethylpentyl group, a 2-methylpentyl group, a 1-cyclohexylethyl group, a 2-methylhexyl group, a 1-methyl-3-pentynyl group or 1 2,6-dimethyl-5-heptenyl group; the double bond between the carbon atoms at 4- and 5-positions is E or Z or a mixture thereof, the asymmetric center in the substituent represented by A is R-configuration or S-configuration or a mixture thereof.
    Type: Grant
    Filed: April 16, 1990
    Date of Patent: October 1, 1991
    Assignees: Mitsubishi Kasei Corporation, Sagami Chemical Research Center
    Inventors: Masakatsu Shibasaki, Mikiko Sodeoka, Yuji Ogawa, Toshiaki Mase, Akira Ishibashi, Daijiro Horii, Toshiji Kanayama, Katsuhiko Iseki, Masaki Shinoda, Chiyoko Ishiyama, Yoshio Hayashi
  • Patent number: 5053525
    Abstract: Mevinolin-like compounds in which the lactone is opened and the hydroxyl function produced thereby is replaced by an oxo function are potent HMG-CoA reductase inhibitors possessing one less asymmetric center.
    Type: Grant
    Filed: February 13, 1986
    Date of Patent: October 1, 1991
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Ta J. Lee, Gerald E. Stokker
  • Patent number: 5051447
    Abstract: Oxime ethers of the general formula ##STR1## where R.sup.1 and R.sup.2 are hydrogen or alkyl,R.sup.3 is hydrogen, halogen, cyano, aryl or aryloxy, the aromatic ring being unsubstituted or substituted, or R.sup.3 is heteroaryl, adamantyl, fluorenyl or cycloalkyl or cycloalkenyl, these radicals being unsubstituted or substituted,X is saturated or unsaturated C.sub.1 -C.sub.12 -alkylene which is unsubstituted or substituted, andn is 0 or 1,and fungicides containing these compounds.
    Type: Grant
    Filed: July 20, 1989
    Date of Patent: September 24, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Wenderoth, Franz Schuetz, Siegbert Brand, Hubert Sauter, Eberhard Ammermann, Gisela Lorezn
  • Patent number: 5049696
    Abstract: Novel 3-hydroxy-3-methylglutaryl-Coenzyme A(HMG-CoA) reductase inhibitors, which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II) ##STR1## and pharmaceutically acceptable salts of the compound (II) in which Z is hydrogen are disclosed.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: September 17, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Ta J. Lee, Clarence S. Rooney, William F. Hoffman
  • Patent number: 5047525
    Abstract: The present application encompasses pharmaceutical preparations, characterized in that they contain as the active component a cyclodextrin clathrate of a prostaglandin of general Formula I ##STR1## wherein R.sub.1 is a hydrogen atom or a straight-chain or branched alkyl residue of up to 10 carbon atoms,R.sub.2 is an alkyl, cycloalkyl, or optionally substituted phenyl group,A and B jointly mean a direct bond orA means a straight- or branched-chain alkylene group of up to 10 carbon atoms andB means an oxygen atom, a direct bond, or a --C.tbd.C--bond, andX means a chlorine or fluorine atom.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: September 10, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Bernd Raduechel, Werner Skuballa, Olaf Loge, Johann-Wilhelm Tack
  • Patent number: 5030654
    Abstract: A series of novel spiro-substituted glutaramide derivatives have been prepared, including the pharmaceutically acceptable salts thereof and bioprecursors therefor, wherein the spiro-substituent completes a 5- or 6-membered carbocycyclic ring and is located at the carbon atom adjacent to the carbamoyl group. These particular compounds are inhibitors of the neutral endopeptidase E.C.3.4.24.11 enzyme and are therefore useful in therapy as diuretic agents for the treatment of hypertension, heart failure, renal insufficiency and other disorders. Methods for preparing these compounds from known starting materials are provided.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: July 9, 1991
    Assignee: Pfizer Inc.
    Inventors: Ian T. Barnish, John C. Danilewicz, Keith James, Gillian M. R. Samuels, Nicholas K. Terrett, Michael T. Williams, Martin J. Wythes
  • Patent number: 5028733
    Abstract: Bicyclooctane and bicycloheptane prostaglandin intermediates have been synthesized.
    Type: Grant
    Filed: December 12, 1989
    Date of Patent: July 2, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 5021453
    Abstract: Compounds of formula (I) and (II): ##STR1## are HMG-CoA reductase inhibitors.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: June 4, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Henry Joshua, Kenneth E. Wilson, Michael S. Schwartz, Ta J. Lee, Gerald E. Stokker
  • Patent number: 4983627
    Abstract: Compounds useful in treating or preventing gastrointestinal ulcers and in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, trans --CH.dbd.CHCH.sub.2 -- or --CH.sub.2 CH.sub.2 --;X is lower alkyl of 1-6 carbon atoms;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);n is an integer from 2-4;R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z);R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is trans --CH.dbd.CHCH.sub.2 --; andR.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: January 8, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Counde O'Yang, Walter Kurz, Keith A. M. Walker, Helen Y. Wu
  • Patent number: 4978775
    Abstract: This invention provides a process for producing bicyclo[3.3.0]octanes expressed by the following formula [II] ##STR1## wherein R.sub.11 represents H, a one-equivalent cation or R.sub.1, R.sub..omega.' , represents R.sub..omega.' , and R.sub.21 represents H or R.sub.2,from a thiol compound expressed by the following formula [I], ##STR2## wherein R.sub.1 represents a C.sub.1-10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted phenyl (C.sub.1-2)alkyl group or a tri(C.sub.1-7 hydrocarbyl)silyl group, Ar represents a substituted or unsubstituted aryl group, R.sub..omega. represents a substituted or unsubstituted C.sub.1-13 alkyl group or a substituted or unsubstituted C.sub.2-13 alkenyl group, and R.sub.2 represents a hydroxyl-protecting group.This process enables to obtain isocarbacyclines or synthetic intermediates therefor with industrial advantages.
    Type: Grant
    Filed: July 16, 1986
    Date of Patent: December 18, 1990
    Assignee: Teijin Limited
    Inventors: Shiro Ikegami, Yasuhiro Torizawa, Seizi Kurozumi
  • Patent number: 4976891
    Abstract: Bicyclic sulfonamido derivatives represented by the formula: ##STR1## wherein R.sub.1 is a hydrogen or lower alkyl; R.sub.2 is an alkyl, substituted or unsubstituted arly, aralkyl or hetelocycle; R.sub.3 is hydrogen or methyl; X is an alkylene or alkenylene which may be substituted by a fluorine atom or atoms and may contain an oxygen, sulfur and/or phenylene in the chain; Y is straight or branched alkylene or alkeneylene, oxygen, or sulfur; m is 0 or 1; and n is 0, 1 or 2, or their salt, said derivatives being useful as antithrombotic, anti-vasoconstricting, and anti-bronchoconstricting drugs.
    Type: Grant
    Filed: March 23, 1989
    Date of Patent: December 11, 1990
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Sanji Hagishita, Kaoru Seno, Susumu Kamata
  • Patent number: 4971987
    Abstract: The invention also relates to carbacyclin derivatives of general formula I' ##STR1## wherein R.sub.9 is an alkyl group of 1-10 carbon atoms or the group --C.dbd.C--(CH.sub.2).sub.m --R.sub.6 whereinm is 1 to 16 andR.sub.6 is hydroxy on amino.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: November 20, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Bob Nieuweboer, Claus-Steffen Stuerzebecher, Ulrich Klar
  • Patent number: 4960907
    Abstract: The invention relates to a process for the production of D,L-bicyclo[3.3.0]octane-3,7-dione-2-carboxylic acid esters of Formula I ##STR1## wherein R is methyl or ethyl, andZ isoxygen or the ketal residue ##STR2## wherein X means ethylene, trimethylene or 2,2-dimethyltrimethylene, characterized in that D,L-bicyclo[3.3.0]octane-3,7-dione-2,6-dicarboxylic acid esters of Formula II ##STR3## wherein R has the meanings given above, are partially saponified and decarboxylated in an aqueous or water-containing medium in the presence of acids, and are optionally selectively ketalized.
    Type: Grant
    Filed: July 24, 1989
    Date of Patent: October 2, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbrueggen, Konrad Krolikiewicz
  • Patent number: 4954524
    Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen or OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, ##STR2## or a heterocyclic residue; or R.sub.1 is NHR.sub.3 wherein R.sub.3 is an acid residue (acyl) or R.sub.2,n is 2, 3, 4, or 5,X is hydrogen or fluorine,A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--,W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR3## wherein the OH-group can be in the .alpha.- or .beta.-position, D is ##STR4## a straight-chain, saturated aliphatic group of 1-10 carbon atoms, a branched, saturated or a straight-chain or branched, unsaturated aliphatic group of 2-10 carbon atoms, all of which can optionally be substituted by fluorine atoms,m is 1, 2, or 3,E is a direct bond, --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 are different from each other and are hydrogen or alkyl or 1-5 carbon atoms, or are hydrogen or halogen,R.sub.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: September 4, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Gerda Mannesmann, Ekkehard Schillinger, Michael H. Town
  • Patent number: 4946864
    Abstract: Novel HMG-CoA reductase inhibitors of formulae (I) and (II) are disclosed.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: August 7, 1990
    Assignee: Merck & Co., Inc.
    Inventors: John Prugh, Albert A. Deana, Clarence S. Rooney
  • Patent number: 4940727
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors are useful as anti-hypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1##
    Type: Grant
    Filed: October 6, 1988
    Date of Patent: July 10, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Edward S. Inamine, Otto D. Hensens, David R. Houck, Ta J. Lee, Robert L. Smith, Wasyl Halczenko, George D. Hartman, Gerald E. Stokker
  • Patent number: 4933319
    Abstract: Described are substituted tetrahydroindanes defined according to the generic structure: ##STR1## wherein Z is a moiety selected from the group consisting of: ##STR2## wherein X represents chloro or bromo; wherein R.sub.1 represents:--OR.sub.3 or --O.sup..crclbar. M.sup..sym. ;wherein R.sub.3 represents hydrogen, methyl or ethyl; wherein M represents alkali metal, sodium potassium or lithium; wherein R.sub.2 represents hydrogen or the moiety: ##STR3## as well as uses of substituted tetrahydroindanes defined according to the structure: ##STR4## wherein Z' represents a moiety selected from the group consisting of: ##STR5## wherein R.sub.2 is hydrogen and wherein R.sub.1 is the moiety:--OR.sub.3 'wherein R.sub.
    Type: Grant
    Filed: October 20, 1989
    Date of Patent: June 12, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Charles E. J. Beck
  • Patent number: 4921526
    Abstract: Substituted benzoyl-bicycloalkyl-1,1,3-diones and related compounds, intermediates therefor, synthesis thereof, and the use of said diones for the control of weeds.
    Type: Grant
    Filed: November 27, 1987
    Date of Patent: May 1, 1990
    Assignee: Sandoz Ltd.
    Inventors: Shy-Fuh Lee, Gary W. Luehr, Carol R. Scott, Werner Trueb
  • Patent number: 4916162
    Abstract: Novel 3-hydroxy-3-methylglutary-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1## and pharmaceutically acceptable salts of the compounds (II) in which Z is hydrogen are disclosed.
    Type: Grant
    Filed: July 18, 1988
    Date of Patent: April 10, 1990
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Clarence S. Rooney, Ta Jyh Lee
  • Patent number: 4912251
    Abstract: The invention concerns a process for manufacturing diesters of bicyclo[3.3.0]-octane dicarboxylic acid having general formula (I), where R.sub.1 is a straight-chain or branched-chain alkyl group with 1 to 10 C atoms. The process is charaterized by the fact that a 2-cyclopentenone derivative having general formula (III), where R.sub.2 is a hydrogen atom or a straight-chain or branched-chain alkyl group with 1 to 10 C atoms, which can be substituted, if necessary, by a phenyl group, is converted in the presence of a base with a diester of aceton dicarboxylic acid having formula (IV), where R.sub.1 has the meaning given above.
    Type: Grant
    Filed: March 17, 1989
    Date of Patent: March 27, 1990
    Assignee: Schering Aktiengesellschaft
    Inventor: Werner Skuballa
  • Patent number: 4912134
    Abstract: Azulene derivatives of the following formula ##STR1## wherein R.sup.1 stands for an alkyl group of 1 to 3 carbon atoms, R.sup.2 stands for an alkyl group of 1 to 3 carbon atoms, and R.sup.3 is at the 5- or 6-position and stands for an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 9 carbon atoms or an aralkyl group of 7 to 10 carbon atoms; have antihyperlipidemic activity. Many of the compounds are also novel per se.
    Type: Grant
    Filed: March 10, 1988
    Date of Patent: March 27, 1990
    Assignee: Ajinomoto Company, Inc.
    Inventors: Masabumi Yasunami, Kahei Takase, Takashi Meguro, Katsumi Suzuki, Osamu Hiwatashi, Masaru Okutsu, Nobuo Kato, Toru Nakamura
  • Patent number: 4902840
    Abstract: Described are substituted tetrahydroindanes defined according to the generic structure: ##STR1## wherein Z is a moiety selected from the group consisting of: ##STR2## wherein X represents chloro or bromo; wherein R.sub.1 represents:--OR.sub.3 or --O.sup..sym. M.sup..crclbar. ;wherein R.sub.3 represents hydrogen, methyl or ethyl; wherein M represents alkali metal, sodium potassium or lithium; wherein R.sub.2 represents hydrogen or the moiety: ##STR3## as well as uses of substituted tetrahydroindanes defined according to the structure: ##STR4## wherein Z' represents a moiety selected from the group consisting of: ##STR5## wherein R.sub.2 is hydrogen and wherein R.sub.1 is the moiety:OR.sub.3 'wherein R.sub.
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: February 20, 1990
    Assignee: International Flavors and Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Charles E. J. Beck
  • Patent number: 4898855
    Abstract: The invention is directed to deuterated vitamin D analogs, and processes and intermediates for their preparation. The end products, that is the deuterated vitamin D analogs, are useful for the treatment osteoporosis and cutaneous inflammations such as psoriasis, and contact dermatitis.
    Type: Grant
    Filed: September 14, 1987
    Date of Patent: February 6, 1990
    Assignee: Hoffman-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Bernard M. Hennessy, Milan R. Uskokovic
  • Patent number: 4894336
    Abstract: Process for the production of optically active (+)-bicyclo[3.3.0]octanol derivatives of formula (+)-I, in which R.sub.1 and R.sub.2 represent jointly an oxygen atom or the double-bond residue --O--X--O-- with X as a straight or branched-chain alkylene with 1-7 C-atoms, or R.sub.1 and R.sub.2 represent separately the residue OR.sub.5 with R.sub.5 as a straight or branched-chain alkyl with 1-7 C-atoms, and R.sub.3 the residue COOZ with Z as a hydrogen atom, straight or branched chain alkyl with 1-7 C atoms, cycloalkyl with 3-6 C atoms, phenyl or aralkyl with 7-10 atoms or R.sub.3 is the residue --(CH.sub.2).sub.n --O--COR.sub.4 with n having the meaning 1-4 and R.sub.4 as a straight or branched-chain alkyl with 1-7 C atoms, cycloalkyl with 3-6 C atoms, phenyl or aralkyl with 7-10 C atoms. The process is characterized in that racemic 3.alpha.-cyloxy-cis-bicyclo[3.3.0]-octane derivatives of formula (+)-II, wherein R.sub.1, R.sub.2 R.sub.3 and R.sub.
    Type: Grant
    Filed: July 13, 1988
    Date of Patent: January 16, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Karl Petzoldt, Helmut Dahl, Werner Skuballa
  • Patent number: 4889947
    Abstract: Sunscreen compositions are described which contain certain substituted naphthalenylidenes which act as UV filters when incorporated in a carrier in amounts ranging from 0.1-50% by weight.
    Type: Grant
    Filed: July 28, 1988
    Date of Patent: December 26, 1989
    Assignee: ICI Americas Inc.
    Inventors: Charalambos J. Phalangas, Thomas P. Cleary
  • Patent number: 4886788
    Abstract: Cyclodextrin clathrates of carbacyclin analogs of general Formula I ##STR1## wherein R.sub.1 is hydrogen, alkyl or alkenyl of up to 10 carbon atoms,A is a --CH.sub.2 CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C-- group,W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position,D is ##STR3## alkylene, or unsaturated alkylene each of which can optionally be substituted by fluorine atoms,m is 1, 2 or 3,E is a direct bond, a --C.tbd.C-- group, or --CR.sub.4 .dbd.CR.sub.5 -- group, wherein R.sub.4 is hydrogen or an alkyl group of 1-5 carbon atoms, and R.sub.5 is hydrogen or an alkyl group of 1-5 carbon atoms, and R.sub.5 is hydrogen, halogen, or an alkyl group of 1-5 carbon atoms,R.sub.2 is alkyl or alkenyl of up to 10 carbon atoms, cycloalkyl of 3-10 carbon atoms or an optionally substituted aryl group of 6-10 carbon atoms, or a heterocyclic group, andR.sub.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: December 12, 1989
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Helmut Vorbrueggen, Helmut Dahl, Claus-Steffen Stuerzebecher, Karl-Heinz Thierauch
  • Patent number: 4885314
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) or (II): ##STR1## and pharmaceutically acceptable salts thereof the compounds of the formula (II) in which R.sup.1 is hydrogen are disclosed.
    Type: Grant
    Filed: September 1, 1988
    Date of Patent: December 5, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Kamlesh P. Vyas, Hanumath P. Kari
  • Patent number: 4876279
    Abstract: Novel 3-hydroxy-3-methylglutaryl-Coenzyme A(HMG-CoA) reductase inhibitors, which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II) ##STR1## and pharmaceutically acceptable salts of the compound (II) in which Z is hydrogen are disclosed.
    Type: Grant
    Filed: May 26, 1988
    Date of Patent: October 24, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Ta J. Lee, William F. Hoffman, Clarence S. Rooney
  • Patent number: 4866090
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1##
    Type: Grant
    Filed: January 7, 1988
    Date of Patent: September 12, 1989
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Robert L. Smith, Ta J. Lee
  • Patent number: 4866093
    Abstract: The dihydro-M-4 and dihydro-IsoM-4 hydroxy carboxylic acids of the formula (II): ##STR1## wherein one of R.sup.1 represents a hydrogen atom and the other represents a hydroxy group and wherein the structure shown as ##STR2## represents a structure of formula ##STR3## and the salts and esters of said acids. The invention also provides pharmaceutical compositions containing said acids, salts and/or esters which are useful for inhibiting cholesterol biosynthesis in the liver.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: September 12, 1989
    Assignee: Sankyo Company Limited
    Inventors: Akira Terahara, Minoru Tanaka