The Bicyclo Ring System Consists Of Two Five-membered Cyclos Patents (Class 549/465)
  • Patent number: 4364950
    Abstract: 5-cyano-prostacyclins of the formula ##STR1## wherein R.sub.1 is OR.sub.2 or NHR.sub.3 ; R.sub.2 and R.sub.3 each independently is (a) H, (b) C.sub.1-10 -alkyl, (c) C.sub.1-10 -alkyl substituted by halo, C.sub.1-4 -alkoxy or phenyl, 1-naphthyl or 2-naphthyl, each optionally substituted as defined below, (d) C.sub.4-10 -cycloalkyl, (e) C.sub.4-10 -cycloalkyl substituted by C.sub.1-4 -alkyl, (f) phenyl, 1-naphthyl or 2-naphthyl, (g) phenyl, 1-naphthyl or 2-naphthyl substituted by 1-3 halogen atoms, phenyl, 1-3 alkyl groups of 1-4 C atoms each, or a chloromethyl-, fluoromethyl-, trifluoromethyl-, carboxyl-, hydroxy- or alkoxy-group of 1-4 C atoms, or (h) an aromatic, 5- or 6-membered heterocyclic ring containing one hetero atom which is O, N or S, the remaining atoms being carbon; R.sub.3 also possibly being an acyl group of a C.sub.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: December 21, 1982
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Helmut Vorbruggen, Bernd Raduchel, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
  • Patent number: 4364951
    Abstract: Prostane derivatives of the formula ##STR1## wherein B is straight-chain or branched alkylene of 1-10 carbon atoms,A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is hydroxymethylene or a ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position, and is optionally modified by replacement of the H atom with an ether or acyl group which is conventional for such replacements in prostaglandins and which is readily cleavable at physiological pH's;D and E together are a direct bond orD is straight-chain or branched alkylene of 1-10 carbon atoms, or, such an alkylene of 4-10 carbon atoms containing a double bond in the 2- or 3- position, all of which can optionally be substituted by fluorine, 1,2-methylene, 1,1-trimethylene, or methoxy;E is oxygen, sulfur, --C.tbd.C-- or a direct bond;R.sub.2 is C.sub.1-10, C.sub.2-10 alkenyl,each of which optionally is substituted phenyl, 1-naphthyl or 2-naphthyl, each of which is substituted as defined below; C.sub.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: December 21, 1982
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Helmut Vorbrueggen, Olaf Loge, Peter Vischer, Bernd Raduchel
  • Patent number: 4359581
    Abstract: A process for preparing a 3-oxo-7-hydroxy-bicyclo[3,3,0]octan-2-ylcarboxylic acid ester of the formula ##STR1## wherein R.sub.1 is alkyl of 1-6 carbon atoms or phenalkyl of 7-10 carbon atoms andR.sub.2 is hydrogen, alkyl or 1-6 carbon atoms, phenalkyl of 7-10 carbon atoms, tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, tri-C.sub.1-4 -alkylsilyl, wherein the alkyl moieties can optionally be substituted by phenyl, or ##STR2## wherein R.sub.3 is alkyl of 1-6 carbon atoms or aryl of 6-12 carbon atoms, comprises oxidizing the corresponding 7-hydroxy-2-oxabicyclo [3,3,0]octan-3-ylideneacetic acid ester of the formula ##STR3## wherein R.sub.1 and R.sub.2 are as defined above, to form the corresponding ketone, reacting the latter with a base which opens the ether oxygen containing ring, and then reducing the resultant product to prepare the 3-oxo-7-hydroxy-bicyclo[3,3,0]octan-2-ylcarboxylic acid ester.
    Type: Grant
    Filed: June 5, 1981
    Date of Patent: November 16, 1982
    Assignee: Schering AG
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen
  • Patent number: 4349690
    Abstract: The present invention provides novel 9-deoxy-9-methylene-6-keto-PGE derivatives which are useful for platelet aggregation inhibition and gastric cyctoprotection.
    Type: Grant
    Filed: April 23, 1981
    Date of Patent: September 14, 1982
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4349689
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: September 14, 1982
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4338249
    Abstract: 16-Fluoro-prostaglandins and pharmaceutical compositions containing the same are prepared. They are useful, for example, as anti-ulcer agents.
    Type: Grant
    Filed: April 7, 1980
    Date of Patent: July 6, 1982
    Assignee: Farmitalia Carlo Erba
    Inventors: Renato Pellegata, Carmelo Gandolfi
  • Patent number: 4338325
    Abstract: The present invention relates to PGI.sub.2 pharmacologically acceptable salts, having pharmacological activity. Particularly, the compounds described herein are useful as platelet aggregation inhibitors.
    Type: Grant
    Filed: October 27, 1980
    Date of Patent: July 6, 1982
    Assignee: The Upjohn Company
    Inventors: Roy A. Johnson, Frank H. Lincoln, John E. Pike
  • Patent number: 4337204
    Abstract: The present invention relates to PGI.sub.2 lower alkyl esters, having pharmacological activity. Particularly, the compounds described herein are useful as platelet aggregation inhibitors.
    Type: Grant
    Filed: March 27, 1981
    Date of Patent: June 29, 1982
    Assignee: The Upjohn Company
    Inventors: Roy A. Johnson, Frank H. Lincoln, John E. Pike
  • Patent number: 4330553
    Abstract: New PGI.sub.2 derivatives and a process for their preparation are disclosed of the formula (I) ##STR1## wherein Q is hydrogen, a pharmacologically acceptable cation, or lower alkyl;A is cis or trans --CH.dbd.CH--, --C.tbd.C--, or --CH.sub.2 --CH.sub.2 --;R.sup.13 is hydrogen or a C.sub.1 to C.sub.4 alkanoyl or is a blockinggroup of the formula R.sup.7 R.sup.8 R.sup.9 Si or ##STR2## wherein R.sup.7, R.sup.8 and R.sup.9 are the same or different and can be straight or branched chain alkyl groups having 1 to 4 carbon atoms and R.sup.10 and R.sup.11 are the same or different and can be hydrogen or methyl, and R.sup.12 represents methyl or ethyl, or is tetrahydropyran-2-yl;R.sup.4 is hydrogen or lower alkyl inthe .alpha. or .beta. steric position;R.sup.1 and R.sup.2 are each hydrogen or lower alkyl;Y is methylene, oxygen or an --NH-- group; andR.sup.3 is lower alkyl or phenyl which can be monosubstituted phenyl.
    Type: Grant
    Filed: November 10, 1980
    Date of Patent: May 18, 1982
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.
    Inventors: Vilmos Simonidesz, Agnes Papp nee Behr, Gabor Kovacs, Jozsef Ivanics, Julia Der nee Foldvary, Istvan Stadler, Istvan Pallagi
  • Patent number: 4328240
    Abstract: 2-oxa-bicyclic prostaglandins are provided, together with methods for their preparation and pharmaceutical and veterinary compositions containing same. The compounds have a wide range of pharmacological utilities, such as hypotensive agents, vasodilatory agents, and anti-aggregating agents.
    Type: Grant
    Filed: July 28, 1978
    Date of Patent: May 4, 1982
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Carmelo Gandolfi, Carlo Passarotti, Alessandro Andreoni, Angelo Fumagalli, Franco Faustini, Roberto Ceserani, Maria M. Usardi
  • Patent number: 4328338
    Abstract: The present invention provides 2,5-inter-o-phenylene-3,4-dinor-6,9.alpha.-epoxy-6.beta.-PGF.sub.1 amides. These compounds are useful for a wide variety of pharmacological and therapeutical purposes, e.g., as antithrombotic agents.
    Type: Grant
    Filed: July 3, 1980
    Date of Patent: May 4, 1982
    Assignee: The Upjohn Company
    Inventors: Udo F. Axen, John C. Sih