Ortho Fused Patents (Class 560/119)
  • Patent number: 4859701
    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: November 6, 1987
    Date of Patent: August 22, 1989
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masabumi Yasunami, Kahei Takase, Takashi Meguro, Katsumi Suzuki, Osamu Hiwatashi, Masaru Okutsu, Nobuo Kato, Toru Nakamura
  • Patent number: 4851436
    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## wherein: n is 1 to 5;R is hydrogen or ##STR2## R.sup.1 is hydrogen or methyl; R.sup.2 is hydrogen or methyl; andR.sup.3 is hydrogen, C.sub.1-5 alkyl or C.sub.1-5 alkyl substituted with a member of the group consisting of phenyl, dimethylamino, or acetylamino; andthe dotted lines at a, b and c represent optional double bonds and pharmaceutically acceptable salts of the compounds (II) in which R.sup.3 is hydrogen are disclosed.
    Type: Grant
    Filed: March 11, 1987
    Date of Patent: July 25, 1989
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Edward Scolnick, Robert L. Smith
  • Patent number: 4812457
    Abstract: Permeability characterized in that the carboxy group at 1-position of the prostaglandin is combined with a cell membrane permeable substance having hydroxy group or amino group through the intermediation of an ester bond to the hydroxy group or an amide bond to the amino group are novel and have improved cell membrane permeability.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: March 14, 1989
    Assignees: Research Development Corporation, Masami Tsuboshima
    Inventors: Shuh Narumiya, Osamu Hayaishi, Yoshiharu Kimura, Masami Tsuboshima
  • Patent number: 4810805
    Abstract: There are disclosed a (2-chloro-3-oxo-1-alkenyl)-bicyclo[3.3.0 octene derivative represented by the formula: ##STR1## wherein R.sup.1 represents --CH.sub.2 CH.sub.2 CH.sub.2 COOR.sup.5, --CH.sub.2 CH.sub.2 --O--CH.sub.2 COOR.sup.5, --CH.dbd.CHCH.sub.2 COOR.sup.5 or --CH.sub.2 CH.sub.2 C.tbd.C--COOR.sup.5 group where R.sup.5 in the groups represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R.sup.2 represents a hydrogen atom, an acyl group having 1 to 7 carbon atoms, a tri(1 to 7 carbon atoms)-hydrocarbylsilyl group or a group forming an acetal bonding with an oxygen atom of a hydroxy group; R.sup.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: March 7, 1989
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Masakatsu Shibasaki, Katsuhiko Iseki, Masaki Shinoda, Chiyoko Aoki, Yoshio Hayashi
  • Patent number: 4804679
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1-3 alkyl, andZ is ##STR2## wherein R.sub.7 is hydrogen, R.sub.8 or M,whereinR.sub.8 is a physiologically acceptable and hydrolyzable ester group, andM is a pharmaceutically acceptable cation,the use thereof for inhibiting cholesterol biosynthesis and lowering the blood cholesterol level and, therefore, in the treatment of hyperlipoproteinemia and atherosclerosis, pharmaceutical compositions comprising such compounds and processes for and intermediates in the synthesis of such compounds.
    Type: Grant
    Filed: August 6, 1987
    Date of Patent: February 14, 1989
    Assignee: Sandoz Pharm. Corp.
    Inventor: Paul L. Anderson
  • Patent number: 4782084
    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: June 29, 1987
    Date of Patent: November 1, 1988
    Assignee: Merck & Co., Inc.
    Inventors: Kamlesh P. Vyas, Hanumath P. Kari
  • Patent number: 4777184
    Abstract: Prostaglandin derivatives, and specifically derivatives of isocarbacyclin, have an optionally substituted methylene group as a substituent on the .alpha.-carbon atom of the .alpha.-side chain. They have a variety of physiological effects, notably a strong ability to inhibit blood platelet aggregation and a strong anti-ulcer activity.
    Type: Grant
    Filed: April 29, 1986
    Date of Patent: October 11, 1988
    Assignee: Sankyo Company Limited
    Inventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Nobuyoshi Iwata, Takeshi Oshima
  • Patent number: 4774341
    Abstract: There are disclosed a bicyclo [3.3.0]octane derivative represented by the formula: ##STR1## wherein R.sup.1 is a substituent selected from the group consisting of a hydrogen atom and a protective group of a hydroxy group;R.sup.2 is a substituent selected from the group consisting of --CH.sub.2 OR.sup.5 and ##STR2## where R.sup.5 is a substituent selected from the group consisting of a hydrogen atom and a protective group of a hydroxy group,R.sup.6 is a substituent selected from the group consisting of an alkyl group, an alkenyl group and an alkynyl group, said substituent being straight, branched or cyclic and having 5 to 10 carbon atoms,X is a substituent selected from the group consisting of a vinylene group and an acetylene group, andR.sup.7 is a substituent selected from the group consisting of an alkyl group, an alkenyl group, and an alkynyl group said substituent being straight, branched or cyclic and having 5 to 10 carbon atoms; andR.sup.3 is a substituent represented by the formula --Y--(CH.sub.2).
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: September 27, 1988
    Assignee: Sagami Chemical Research Center
    Inventors: Masakatsu Shibasaki, Mikiko Sodeoka, Yuji Ogawa
  • Patent number: 4766246
    Abstract: Sweeteners of the formula: ##STR1## and food-acceptable salts thereof, where the substituents are disclosed herein.
    Type: Grant
    Filed: August 19, 1986
    Date of Patent: August 23, 1988
    Assignee: General Foods Corporation
    Inventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
  • Patent number: 4764528
    Abstract: Novel 2,4-pentadienoic acid derivatives are disclosed. As the examples are mentioned 3-(4-carboxy-trans, trans-1,3-butadienyl)-6-exo-(3.alpha.-hydroxy-trans-1-octenyl)-7-endo-hydr oxybicyclo[3.3.0]oct-2-ene, 3-(5-carboxy-trans, trans-2,4-pentadienyl)-6-exo-(3.alpha.-hydroxy-trans-1-octenyl)-7-endo-hyd roxybicyclo[3.3.0]oct-2-ene and the like. These compounds are useful as a platelet aggregation inhibitor, especially as a thrombosis-prophylactic agent.
    Type: Grant
    Filed: March 10, 1987
    Date of Patent: August 16, 1988
    Assignee: Teruo Kabushiki Kaisha
    Inventors: Keiko Chiba, Makoto Takai, Toshio Wakabayashi
  • Patent number: 4757087
    Abstract: Carbacyclin derivatives with anti-ulcer activity comprise compounds of the general formula (I): ##STR1## (wherein R.sup.1 is selected from the group consisting of a hydrogen atom and an alkyl group having from 1 to 10 carbon atoms; R.sup.2 is selected from the group consisting of a hydrogen atom and a methyl group; and R.sup.3 is selected from the group consisting of a 3-butenyl group, a 4-pentenyl group and a 5-methyl-4-hexenyl group), and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: March 18, 1986
    Date of Patent: July 12, 1988
    Assignee: Sankyo Company Limited
    Inventors: Koichi Kojima, Shinsaku Kobayashi
  • Patent number: 4754055
    Abstract: The present invention describes allenic prostacyclin derivatives of the formula: ##STR1## wherein: n is 0, 1, or 2;R.sup.1 is hydrogen, lower alkyl, or a pharmaceutically acceptable cation;R.sup.2 is hydrogen, lower alkyl, cycloalkyl, heteroaryl, halogen, phenyl, alkylthio, phenylthio, alkylsulfinyl, phenylsulfinyl or trifluoromethyl;R.sup.3 is lower alkyl, cycloalkyl, phenyl, benzyl, cycloheteroalkyl, lower alkyl having one to eight carbons substituted with one or more fluorines or containing 1 or 2 unsaturated bonds; andcarbon 15 may be in the R or the S configuration, or a mixture of R and S.These compounds are useful for the treatment of platelet dysfunction, atherosclerosis, allergic disorders, gastric ulcers, hypertension and tumor cell metastasis. Also disclosed is the process for preparing them and the appropriate intermediates.
    Type: Grant
    Filed: September 10, 1986
    Date of Patent: June 28, 1988
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Masateru Miyano
  • Patent number: 4735966
    Abstract: Compounds useful 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--, --CH.sub.2 CH.sub.2 -- or --CH.dbd.CHCH.sub.2 --;X is lower alkoxy, hydroxy, or (2,2,2)-trifluoroethoxy;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);is an integer of 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 --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.
    Type: Grant
    Filed: August 25, 1986
    Date of Patent: April 5, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Helen Y. Wu, Walter Kurz
  • Patent number: 4736064
    Abstract: Prodrugs of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formula (I): ##STR1## and pharmaceutically acceptable salts thereof are disclosed.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: April 5, 1988
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Wasyl Halczenko, George Hartman
  • Patent number: 4736058
    Abstract: A novel prostacyclins expressed by the following formula (1) ##STR1## wherein a symbol between the 2-position and 3-position indicates single bond or double bond; G indicates --CO.sub.2 R.sup.5 or --CONR.sup.6 R.sup.7 in which R.sup.5 is a hydrogen atom, C.sub.1 -C.sub.10 alkyl group, substituted or unsubstituted alicyclic group, substituted or unsubstituted phenyl (C.sub.1 -C.sub.2) alkyl group, tri (C.sub.1 -C.sub.7) hydrocarbon-silyl group, or one equivalent cation, R.sup.6 and R.sup.7 are identical or different and each representing a hydrogen atom, or C.sub.1 -C.sub.10 alkyl group, or R.sup.6 and R.sup.7 are substituted or unsubstituted five to six-membered ring which may join together with a nitrogen atom to which they are linked and further contain a hetero atom; R.sup.1 indicates a hydrogen atom, or methyl group; R.sup.2 indicates an unsubstituted C.sub.3 -C.sub.8 alkyl group substituted or unsubstituted alicyclic group, or substituted C.sub.1 -C.sub.
    Type: Grant
    Filed: September 27, 1984
    Date of Patent: April 5, 1988
    Assignee: Teijin Limited
    Inventors: Shiro Ikegami, Seizi Kurozumi
  • Patent number: 4733003
    Abstract: Compounds of formula (I): ##STR1## [wherein X represents a hydrogen atom or a 2-methylbutyryl group, Y represents a hydrogen atom or a methyl group and R.sup.1 and R.sup.2 are the same or different and each represents an oxygen atom or a group of formula .dbd.N--OR.sup.3 (wherein R.sup.3 represents a hydrogen atom or an alkyl group)], the free hydroxy-carboxylic acids corresponding thereto and salts and esters of said acids may be prepared by oxidizing and, if necessary, oximating a corresponding ML-236A, ML-236B, MB-530A or MB-530B compound, and these compounds have valuable antihypercholesteraemic activity.
    Type: Grant
    Filed: May 6, 1986
    Date of Patent: March 22, 1988
    Assignee: Sankyo Company Limited
    Inventors: Junya Ide, Shigeki Muramatsu, Yoshio Tsujita, Msao Kuroda
  • Patent number: 4732914
    Abstract: Prostacyclin (PGI.sub.2) analogs having a 6a-carba feature, for example a compound of the formula ##STR1## said analogs having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.
    Type: Grant
    Filed: May 14, 1987
    Date of Patent: March 22, 1988
    Assignee: The Upjohn Company
    Inventor: Douglas R. Morton, Jr.
  • Patent number: 4730078
    Abstract: The present invention relates to allenic prostacyclin derivatives of the formula: ##STR1## wherein: n is 0, 1, 2R.sup.1 is hydrogen, lower alkyl, lower hydroxyalkyl, or a pharmaceutically acceptable cation;R.sup.2 is hydrogen, lower alkyl, cycloalkyl, heteroalkyl, halogen, aryl, alkylthio, phenylthio, alkylsulfinyl, phenylsulfonyl, or trifluoromethyl,R.sup.3 is a lower alkyl, a cycloalkyl, phenyl, benzyl, a cycloheteroalkyl, a lower alkyl having one to eight carbons substituted with one or more fluorines or containing 1 or 2 unsaturated bonds; and carbon 15 may be in the R or the S configuration, or a mixture of R and S with the proviso that when R.sup.1 is a lower alkyl or lower hydroxyalkyl that carbon 15 is not in the R configuration.These compounds are useful for the treatment of platelet dysfunction and atherosclerosis. Also disclosed is the process for preparing these compounds and their appropriate intermediates.
    Type: Grant
    Filed: May 13, 1987
    Date of Patent: March 8, 1988
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Masateru Miyano
  • Patent number: 4730060
    Abstract: New agents of carbacyclin derivatives are disclosed, which are represented by the following formula: ##STR1## wherein A is a --CH.dbd.CH-- or --C.tbd.C-- group. B is a substituted or unsubstituted indanyl group, substituted or unsubstituted benzodioxanyl group, substituted or unsubstituted benzodioxolanyl group or 2,3,5,6,7, 8-hexahydrobenzodioxanyl group. D is --CH.sub.2 -- or --O--. .about.OH group represents .alpha. or .beta. configuration of OH group; and ##STR2## These compounds are useful as anit-ulcer, anti-hypertensive or anti-thrombotic agents.
    Type: Grant
    Filed: June 1, 1987
    Date of Patent: March 8, 1988
    Assignee: Kotobuki Seiyaku Co. Ltd.
    Inventors: Tsuyoshi Tomiyama, Akira Tomiyama, Takashi Yanagisawa, Masayuki Yokota
  • Patent number: 4719229
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents are represented by the following structural formulae (I) and (II): ##STR1## are disclosed.
    Type: Grant
    Filed: May 13, 1987
    Date of Patent: January 12, 1988
    Assignee: Merck & Co., Inc.
    Inventors: Robert A. Reamer, Laszlo R. Treiber
  • Patent number: 4708963
    Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, a heterocyclic residue, or NHR.sub.3, wherein R.sub.3 is an acid residue or hydrogen;X is oxygen;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D is a straight-chain or branched, saturated or unsaturated aliphatic group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms, 1,2-methylene, 1,1-trimethylene;E is --C.tbd.C-- or --CR.sub.6 .dbd.CH.sub.7 -- wherein R.sub.6 and R.sub.7 are hydrogen or alkyl of 1-5 carbon atoms;R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group;R.sub.5 is free or functionally modified hydroxy and,when R.sub.
    Type: Grant
    Filed: May 28, 1985
    Date of Patent: November 24, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
  • Patent number: 4709085
    Abstract: A process for producing a cyclopropane derivative comprising contacting a diazo compound and an olefinically unsaturated compound in the presence of a catalytic amount of copper cation-exchanged perfluorinated ion exchange polymer is disclosed.
    Type: Grant
    Filed: January 5, 1987
    Date of Patent: November 24, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: William A. Nugent, Francis J. Waller
  • Patent number: 4699921
    Abstract: Disclosed is a pharmaceutical composition 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 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 a 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 in the R-configuration or the S-configuration or a mixture thereof.
    Type: Grant
    Filed: August 8, 1985
    Date of Patent: October 13, 1987
    Assignees: Mitsubishi Yuka Pharmaceutical Co., Ltd., 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: 4698363
    Abstract: Prostaglandin analogues of the formula: ##STR1## (wherein R.sup.1 represents a hydrogen atom or an aliphatic or alicyclic hydrocarbon radical, Y.sup.1 represents a carbonyl or hydroxymethylene group, A.sup.1 represents an alkylene linkage containing 1, 2 or 3 carbon atoms and optionally bearing a methyl or ethyl substituent, R.sup.2 represents a hydrogen atom or a methyl or ethyl group and R.sup.3 represents a hydrogen atom or R.sup.2 and R.sup.3 form an alkylene linkage containing 2 or 3 carbon atoms, optionally bearing a methyl or ethyl substituent, such that the symbols A.sup.1, R.sup.2 and R.sup.3, together with the carbon atoms through which they are connected, may form a cycloalkyl ring of 5, 6, 7 or 8 carbon atoms, optionally bearing one or two methyl or ethyl substituents, or A.sup.1 and R.sup.
    Type: Grant
    Filed: November 20, 1985
    Date of Patent: October 6, 1987
    Assignee: May & Baker Limited
    Inventor: Terance W. Hart
  • Patent number: 4695587
    Abstract: Tetrahydro-M-4 and tetrahydro-IsoM-4 hydroxy carboxylic acids of the formula (II): ##STR1## wherein one of R.sup.1 and R.sup.2 represents a hydrogen atom and the other represents a hydroxy group, and the salts and esters of said acids which are useful for inhibiting chloresterol biosynthesis in the liver. The invention also provides pharmaceutical compositions containing said acid(s).
    Type: Grant
    Filed: April 26, 1984
    Date of Patent: September 22, 1987
    Assignee: Sankyo Company Limited
    Inventors: Akira Terahara, Minoru Tanaka
  • Patent number: 4692464
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is (a) hydrogen, (b) C.sub.1-10 alkyl, (c) C.sub.1-10 alkyl substituted by halogen; C.sub.1-4 alkoxy; C.sub.6-10 aryl; C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group; di-C.sub.1-4 -alkylamino; or tri-C.sub.1-4 -alkylammonium, (d) C.sub.4-10 cycloalkyl, (e) C.sub.4-10 cycloalkyl substituted by C.sub.1-4 alkyl, (f) C.sub.6-10 aryl, (g) C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group, or (h) an aromatic heterocycle of 5 or 6 ring atoms one of which is O, N or S;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--;W is hydroxymethylene, RO-methylene, CH.sub.3 or CH.sub.3, ##STR2## wherein OH or OR is in the .alpha.- or .beta.
    Type: Grant
    Filed: February 26, 1982
    Date of Patent: September 8, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Gerda Mannesmann, Wolfgang Losert, Jorge Casals
  • Patent number: 4689349
    Abstract: Potent tumor inhibitors are prepared which are compounds of the formula: ##STR1## wherein Q is CO, CH(OH) or C(OH)CH.sub.3,M.sub.1 is halogen,M.sub.2 is halogen or hydrogen,c is one or twop is 0 or 1, andone of X and X' is H and the other is hydroxy-C.sup.2-9 alkyl, methoxy-C.sup.2-9 -alkyl, ethoxy-C.sup.2-9 -alkyl, oxo-C.sup.2-9 -alkyl, formyl-C.sup.2-9 -alkyl, carboxy-C.sup.2-9 -alkyl or (C.sub.1-2 -alkyl)oxycarbonyl-C.sup.2-9 -alkyl.
    Type: Grant
    Filed: March 12, 1986
    Date of Patent: August 25, 1987
    Assignee: CBD Corporation
    Inventors: Walter J. Kasha, Chantal S. Burnison
  • Patent number: 4680307
    Abstract: A compound of the formula: ##STR1## wherein X.sup.1 is a free or an esterified carboxyl group, or a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7 membered saturated heterocyclic group, Y.sup.1 is a group of the formula: ##STR3## (R.sup.6 is a hydrogen atom or C.sub.1 -C.sub.4 alkyl group), ##STR4## (R.sup.6 is as defined above), ##STR5## R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sup.1 and R.sup.2, when taken together, mean a shingle linkage to from a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.1 -C.sub.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: July 14, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Muraoka, Toshio Nakamura, Akihiko Sugie, Keiichi Ono, Michihiro Yamamoto
  • Patent number: 4678805
    Abstract: Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension, and atherosclerosis are compounds depicted in formulas (1), (2), and (3): ##STR1## wherein: Y is exo-(lower alkyl) or endo-(lower alkyl);n is 2 or 3;R.sub.1 is CH.sub.2 OH, CHO, CO.sub.2 R or CO.sub.2 H;R.sub.2 is hydrogen or methyl; andR.sub.3 is linear or branched alkyl having 5-10 carbon atoms, ##STR2## or --(CH.sub.2).sub.m -phenyl optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen,in whicha is 0, 1 or 2;b is 3-7;m is 1 or 2; andR is ##STR3## wherein X is ##STR4## in which each R.sub.4 is independently hydrogen or lower alkyl having 1-6 carbon atoms, and the pharmaceutically acceptable, non-toxic salts and esters thereof.
    Type: Grant
    Filed: July 28, 1986
    Date of Patent: July 7, 1987
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Arthur F. Kluge, Helen Y. Wu
  • Patent number: 4675435
    Abstract: A method is disclosed for the production of esters by reaction of an alkyl acyclic allylic ether such as 8-methoxy-1,6-octadiene with carbon monoxide in the presence of a halide of nickel, cobalt or iron as a catalyst and especially nickel iodide for the production of esters. Carbonylation of 8-methoxy-1,6-octadiene results in the production of methyl-3,8-nonadienoate; 2-(carbomethoxymethyl)-vinylcyclopentane; 2-(carbomethoxymethyl)-6-vinylcyclohexanone and 2-carbomethoxymethylbicyclo(3.3.0)-octan-3-one.
    Type: Grant
    Filed: July 17, 1986
    Date of Patent: June 23, 1987
    Assignee: National Distillers and Chemical Corporation
    Inventors: Ronnie M. Hanes, William D. Baugh
  • Patent number: 4668699
    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## wherein: n is 1 to 5;R is hydrogen or ##STR2## R.sup.1 is hydrogen or methyl; R.sup.2 is hydrogen or methyl; andR.sup.3 is hydrogen, C.sub.1-5 alkyl or C.sub.1-5 alkyl substituted with a member of the group consisting of phenyl, dimethylamino, or acetylamino; andthe dotted lines at a, b and c represent optional double bonds and pharmaceutically acceptable salts of the compounds (II) in which R.sup.3 is hydrogen are disclosed.
    Type: Grant
    Filed: August 5, 1985
    Date of Patent: May 26, 1987
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Robert L. Smith, Edward Scolnick
  • Patent number: 4638071
    Abstract: The following dipeptides possess a high order of sweetness: ##STR1## wherein X=O or S;R is alkyl containing 1-3 carbon atoms;R.sub.1 is cycloalkyl, cycloalkenyl, lower alkyl-substituted cycloalkyl or cycloalkenyl, bicycloalkyl, bicycloalkenyl, tricycloalkyl, cyclic ether, cyclic thioether, cyclic sulfoxides, cyclic sulfones, aryl, benzyl, alkylaryl, aromatic heterocyclic or alkyl substituted aromatic heterocyclic containing up to 10 ring carbon atoms and up to a total of 12 carbon atoms;R.sub.2, R.sub.3, R.sub.4 and R.sub.6 are each H or lower alkyl;R.sub.5 is H, lower alkyl or cycloalkyl containing 3-5 ring carbons;each n=0, 1 or 2;m=0 or 1;Z is an alkylene chain containing 0-2 carbon atoms in the principal chain and up to a total of 6 carbon atoms;and food-acceptable salts.
    Type: Grant
    Filed: December 27, 1984
    Date of Patent: January 20, 1987
    Assignee: General Foods Corporation
    Inventors: Ronald E. Barnett, Paul R. Zanno, Glenn M. Roy
  • Patent number: 4633011
    Abstract: 3a,6,6,9a-Tetramethylperhydronaphto[2,1-b]furan, a typical ambergris perfume ingredient is prepared via a novel process from 1.beta.-(2-hydroxyethyl)-perhydro-2,5,5,8a.beta.-tetramethyl-2.beta.-trans -naphthalenol by cyclization with an acidic cyclization agent in the presence of nitromethane.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: December 30, 1986
    Assignee: Firmenich SA
    Inventors: George H. Buchi, Hans Wuest
  • Patent number: 4632997
    Abstract: A method for preparing a cis-bicyclo[3.3.0]octylidene derivative represented by the formula: ##STR1## wherein R.sup.1 is a hydrogen atom or an alkyl group; R.sup.2 is a hydrogen atom or a protective group for hydroxyl group; and Y is ##STR2## where R.sup.3 is a hydrogen atom or a protective group for hydroxyl group; R.sup.4 is a hydrogen atom or a straight, branched or cyclic alkyl group, alkenyl group or alkynyl group; and X is a group represented by CH.dbd.CH or C.tbd.C,comprises carrying out the catalytic hydrogenation reaction of a (1-alkenyl)-cis-bicyclo[3.3.0]octene derivative represented by the formula: ##STR3## wherein R.sup.1, R.sup.2 and Y have the same meanings as defined above, in the presence of a metal carbonyl compound or its complex represented by the formula:Mw(CO)x(H)y(R)zwherein M is a metal element of the group VIB; R is a .pi. ligand or a phosphine ligand; w is 1 or 2; x is an integer of 3 to 6; y is 0 or 1; and z is 0 or an integer of 1 to 3.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: December 30, 1986
    Assignee: Sagami Chemical Research Center
    Inventors: Masakatsu Shibasaki, Mikiko Sodeoka, Yuji Ogawa
  • Patent number: 4628110
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: October 30, 1984
    Date of Patent: December 9, 1986
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4622418
    Abstract: Amides of .alpha.-aminodicarboxylic acids and .beta.-aminoethers are low calorie sweetners.
    Type: Grant
    Filed: April 4, 1985
    Date of Patent: November 11, 1986
    Assignee: General Foods Corporation
    Inventors: Ronald E. Barnett, Paul R. Zanno, Glenn M. Roy
  • Patent number: 4622417
    Abstract: Dipeptides of certain .alpha.-amino dicarboxylic acids and etherified hydroxy .alpha.-amino-mono-carboxylic acid esters possess a high order of sweetness. These dipeptides have the following formula: ##STR1## wherein R is alkyl containing 1-3 carbon atoms;R.sub.1 is cycloalkyl, cycloalkenyl, lower alkyl substituted cycloalkyl or cycloalkenyl, bicycloalkyl, bicycloalkenyl or tricycloalkyl containing up to 10 ring carbon atoms and up to a total of 12 carbon atoms;R.sub.2 and R.sub.4 are each H or alkyl containing 1-3 carbon atoms;R.sub.3 is H, alkyl containing 1-6 carbon atoms or cycloalkyl containing 3-5 ring carbons;n=0, 1 or 2; andm=0 or 1;and food acceptable salts thereof.
    Type: Grant
    Filed: December 27, 1984
    Date of Patent: November 11, 1986
    Assignee: General Foods Corporation
    Inventors: Ronald E. Barnett, Paul R. Zanno, Glenn M. Roy
  • Patent number: 4619782
    Abstract: Sweeteners of the formula: ##STR1## and food-acceptable salts thereof, where the substituents are disclosed herein.
    Type: Grant
    Filed: April 15, 1985
    Date of Patent: October 28, 1986
    Assignee: General Foods Corporation
    Inventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
  • Patent number: 4618626
    Abstract: Carbacyclin esters of Formula I ##STR1## wherein R.sub.1 is an unsubstituted or substituted aromatic residue,R.sub.2 is a free or functionally modified hydroxy group,R.sub.3 is an alkyl or cycloalkyl group, or an optionally substituted aryl group, or a heterocyclic group,X is an oxygen atom or the group --CH.sub.2 --,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 the group ##STR3## a straight-chain saturated alkylene group of 1-5 carbon atoms, a branched, saturated or a straight-chain or branched, unsaturated alkylene group of 2-5 carbon atoms, which groups can optionally be substituted by fluorine atoms,E is a direct bond, a --C.tbd.C--group, or a --CR.sub.4 .dbd.CR.sub.5 -- group wherein R.sub.2 and R.sub.
    Type: Grant
    Filed: September 16, 1985
    Date of Patent: October 21, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Gerda Mannesmann, Bob Nieuweboer, Michael-Harold Town
  • Patent number: 4613710
    Abstract: 3a,6,6,9a-Tetramethylperhydronaphto[2,1-b]furan, a typical ambergris perfume ingredient is prepared via a novel process from 1.beta.-(2-hydroxyethyl)-perhydro-2,5,5,8a.beta.-tetramethyl-2.beta.-trans -naphthalenol by cyclization with an acidic cyclization agent in the presence of nitromethane.
    Type: Grant
    Filed: August 8, 1984
    Date of Patent: September 23, 1986
    Assignee: Firmenich SA
    Inventors: George H. Buchi, Hans Wuest
  • Patent number: 4610805
    Abstract: Nematic liquid crystalline mixtures, which can be used in optoelectronic components. Compounds are provided which influence the characteristics of mixtures in the direction of high clarification temperatures at simultaneous favorable switching times. It has been found that compounds of the general formula ##STR1## wherein n, m=1 to 10 in nematic mixtures in quantities of 5 to 40% considerably increase the clarification points without significantly increasing the viscosity, so that favorable switching times are obtained. The new mixtures can be used for the production of optoelectronic components (displays) for watches, computers and other devices.
    Type: Grant
    Filed: January 29, 1985
    Date of Patent: September 9, 1986
    Assignee: VEB Werk fur Fernsehelektronik im VEB Kombinat Mikroelektronik
    Inventors: Michael Schellenberger, Sabine Richter, Hans-Joachim Deutscher, Horst Zaschke, Dietrich Demus
  • Patent number: 4611081
    Abstract: A novel process for intermediates in the synthesis and hypercholesterolemic compounds of the HMG-CoA reductase type of the following general formula (1): ##STR1## involving an enantioselective aldol condensation is disclosed.
    Type: Grant
    Filed: July 5, 1985
    Date of Patent: September 9, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Joseph E. Lynch, Ichiro Shinkai, Ralph P. Volante
  • Patent number: 4608388
    Abstract: Compounds useful in treating cardiovascular disorders such as thrombosis, hypertension, and atherosclerosis are compounds depicted in formulas (1), (2), and (3): ##STR1## wherein: n is 2 or 3;R.sub.1 is CH.sub.2 OH, CHO, CO.sub.2 R or CO.sub.2 H;R.sub.2 is hydrogen or methyl; andR.sub.3 is linear or branched alkyl having 5-10 carbon atoms, ##STR2## optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen,in whicha is 0, 1 or 2;b is 3-7;m is 1 or 2; andR is ##STR3## in which each R.sub.4 is independently hydrogen or lower alkyl having 1-6 carbon atoms,and the pharmaceutically acceptable, non-toxic salts and esters thereof.
    Type: Grant
    Filed: March 27, 1985
    Date of Patent: August 26, 1986
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Arthur F. Kluge, Anthony L. Willis, Counde O'Yang
  • Patent number: 4604472
    Abstract: Compounds of formula (I): ##STR1## [wherein X represents a hydrogen atom or a 2-methylbutyryl group, Y represents a hydrogen atom or a methyl group and R.sup.1 and R.sup.2 are the same or different and each represents an oxygen atom or a group of formula .dbd.N--OR.sup.3 (wherein R.sup.3 represents a hydrogen atom or an alkyl group)], the free hydroxy-carboxylic acids corresponding thereto and salts and esters of said acids may be prepared by oxidizing and, if necessary, oximating a corresponding ML-236A, ML-236B, MB-530A or MB-530B compound, and these compounds have valuable antihypercholesteraemic activity.
    Type: Grant
    Filed: July 9, 1985
    Date of Patent: August 5, 1986
    Assignee: Sankyo Company Limited
    Inventors: Junya Ide, Shigeki Muramatsu, Yoshio Tsujita, Masao Kuroda
  • Patent number: 4588823
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: September 27, 1984
    Date of Patent: May 13, 1986
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4576962
    Abstract: The 13,14-didehydro-15-oxo analogues of natural prostaglandins possess high cytoprotective activity and low diarrheogenic activity, low anti-hemostatic activity and low smooth muscle contraction activity.
    Type: Grant
    Filed: May 4, 1984
    Date of Patent: March 18, 1986
    Assignee: The Procter & Gamble Company
    Inventor: Randall S. Matthews
  • Patent number: 4564694
    Abstract: A colorless liquid crystalline compound having at least one 6-membered ring and non-cyclic end groups in the molecular skelton, said 6-membered containing two or more carbon atoms, at least one of which is directly bonded to a methylene group of a non-cyclic group having an alkoxy group at another end has a wide mesomorphic range. When said colorless liquid crystalline compound is mixed with a liquid crystal composition, the resulting mixture also has an enlarge mesomorphic range and in almost all cases has a reduced viscosity.
    Type: Grant
    Filed: February 24, 1982
    Date of Patent: January 14, 1986
    Assignees: Hitachi, Ltd., Kanto Chemical Co., Inc.
    Inventors: Yoichi Hirai, Tsunenori Fujii, Kaoru Koto, Kenji Suzuki, Masahiro Yoshida, Hisashi Okawa, Yoshiaki Okabe, Teruo Kitamura, Hisao Yokokura, Shintaroo Hattori, Akio Mukoh, Mikio Sato
  • Patent number: 4552898
    Abstract: Compounds useful in treating cardiovascular disorders are the carboxylic acids depicted in formulas (1) and (2) ##STR1## as well as their pharmaceutically acceptable, non-toxic salts and esters, wherein:n is an integer from one to four;R.sub.1 is hydroxy;R.sub.2 is hydrogen; orR.sub.1 and R.sub.2 together are an oxo group;R.sub.3 is ##STR2## wherein A is --CH.sub.2 --CH.sub.2 --; trans--CH.dbd.CH--; --C.tbd.C--; andR.sub.4 is linear or branched alkyl of one to twelve carbons, preferably 1-10 carbons, most preferably 3-8 carbons, cycloalkyl of three to eight carbons; phenyl optionally substituted with one or two identical substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, trifluoromethyl, and halo; or phenylloweralkyl optionally substituted with one or two identical substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, trifluoromethyl, and halo.
    Type: Grant
    Filed: August 19, 1983
    Date of Patent: November 12, 1985
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Tsung-Tee Li, Michael Marx
  • Patent number: 4537989
    Abstract: A compound of the formula ##STR1## wherein X.sup.1 is a free or an esterified carboxyl group, or a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7 membered saturated heterocyclic group), Y is a group of the formula: ##STR3## (R.sup.6 is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group) or ##STR4## (R.sup.6 is as defined above), R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sup.1 and R.sup.2, when taken together, mean a single linkage to form a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.1 -C.sub.
    Type: Grant
    Filed: April 15, 1983
    Date of Patent: August 27, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Akihiko Sugie, Masami Muraoka, Michihiro Yamamoto
  • Patent number: RE33033
    Abstract: .Iaddend.hypercholesterolemic compounds of the HMG-CoA reductase type of the following general formula (1): ##STR1## involving an enantioselective aldol condensation is disclosed.
    Type: Grant
    Filed: September 18, 1987
    Date of Patent: August 22, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Joseph E. Lynch, Ichiro Shinkai, Ralph P. Volante