Chalcogen Attached Directly To Ring Sulfur Of The Hetero Ring By Nonionic Bonding Patents (Class 549/53)
  • Patent number: 5863936
    Abstract: Methods and compositions for treating cancer and other diseases in which inhibition of telomerase activity can ameliorate disease symptoms or prevent or treat the disease relate to compounds characterized by the following structure: ##STR1## and their pharmaceutically acceptable salts. Y is selected from the group consisting of oxygen, sulfur, sulfonyl, sulfinyl, and --NR.sub.7 --. R.sub.1 is --TR.sub.8, where T is --C(X.sub.1)-- or --SO.sub.2 --, and R.sub.8 is selected from the group consisting of --OR.sub.9, --NHNHSO.sub.2 R.sub.9, --NHNHC(X.sub.2)OR.sub.9, --NR.sub.9 R.sub.10, --NHNHC(X.sub.2)NR.sub.9 R.sub.10, --NHCR.sub.9 R.sub.10 C(X.sub.2)NR.sub.11 R.sub.12, --NHC(X.sub.2)NR.sub.9 R.sub.10, and the piperazinyl moiety shown below: ##STR2## where n is 0 or 1, and Q.sub.n, for n=1, is --SO.sub.2 --, --C(X.sub.2)-- or --C(X.sub.2)NR.sub.10 --. R.sub.2 -R.sub.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: January 26, 1999
    Assignee: Geron Corporation
    Inventors: Federico C.A. Gaeta, Adam A. Galan, Elaine C. Stracker
  • Patent number: 5849798
    Abstract: Novel pharmaceutically/cosmetically-active polyaromatic heterocyclic compounds have the structural formula (I): ##STR1## in which Z is a divalent radical selected from among --O--, --S-- or --Nr'-- and Ar is either a radical having the following structural formula (II): ##STR2## or a radical having the following structural formula (III): ##STR3## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: December 15, 1998
    Assignee: Centre International De Recherches Dermatologiques Galderma
    Inventors: Bruno Charpentier, Philippe Diaz, Philippe Nedoncelle
  • Patent number: 5789436
    Abstract: A compound represented by formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom, a lower alkyl group or an acyl group; R.sub.2 and R.sub.3, which may be the same or different, each represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted alkenyl group; R.sub.4 represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted alkenyl group, or R.sub.4 forms a double bond between the carbon atom to which R.sub.3 is bonded and the adjacent carbon atom to form a benzothiophene skeleton, or R.sub.3 and R.sub.4 are taken together to form a 5- to 8-membered spiro ring which may contain a hetero atom, e.g., oxygen, sulfur or nitrogen; and n represents an integer of 0 to 2, or a pharmaceutically acceptable salt thereof. The compound of formula (I) exhibits an inhibitory action on the oxidative modification of LDL and is useful as therapeutics of arteriosclerosis.
    Type: Grant
    Filed: October 9, 1996
    Date of Patent: August 4, 1998
    Assignee: Chugai Seiyak Kabushiki Kaisha
    Inventors: Yoshiaki Kato, Akira Ishikawa, Kunio Tamura
  • Patent number: 5747540
    Abstract: Compounds such as ##STR1## or pharmaceutically acceptable salts thereof, are HIV protease inhibitors. These compounds are useful in the prevention or treatment of infection by HIV and in the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.
    Type: Grant
    Filed: October 21, 1996
    Date of Patent: May 5, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Craig A. Coburn, Randall W. Hungate, Richard C. A. Isaacs, Joseph P. Vacca, Mary Beth Young
  • Patent number: 5712304
    Abstract: New benzothiophenecarboxamide S-oxides of the formula (I) ##STR1## in which R.sup.1 represents optionally substituted alkyl, or represents alkenyl or alkinyl, or represents in each case optionally substituted cycloalkyl or cycloalkylalkyl, or represents in each case optionally substituted aralkyl, aralkenyl, aralkinyl or aryl andR.sup.2 represents hydrogen or optionally substituted alkyl, orR.sup.1 and R.sup.2 together with the nitrogen atom to which they are bonded represent an optionally substituted heterocycle,R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another in each case represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, andR.sup.1 represents hydrogen or halogen,a process for their preparation, and their use as microbicides in plant protection and in the protection of materials.New intermediates for the preparation of substances of the formula (I).
    Type: Grant
    Filed: November 14, 1995
    Date of Patent: January 27, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Ludwig Elbe, Reinhard Lantzsch, Ralf Tiemann, Heinz-Wilhelm Dehne, Martin Kugler, Wilfried Paulus, Heinrich Schrage
  • 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: 5684031
    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 about 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 is hydrogen or straight, branched or cyclic alkyl, aryl or C(.dbd.NH)--NHR.sub.4 ; and(f) R.sub.2, R.sub.3, and R.sub.4, are independently hydrogen, straight, branched or cyclic alkyl having from one to 10 carbon atoms, or aryl; R.sub.2 and R.sub.3 can be bonded together to form a ring having 5 or 6 atoms.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 4, 1997
    Assignee: The Procter & Gamble Company
    Inventors: John Michael Janusz, James Madison Ridgeway, II
  • Patent number: 5684041
    Abstract: A compound having the structure: ##STR1## wherein (a) n is from 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 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 O or S; and(f) R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen, straight, branched or cyclic alkyl having from 1 to 10 carbon atoms, aryl, heterocyclyl, heteroaryl, hydroxy, or alkoxy; or R1, R2 or R3 may be bonded to form one or more rings each ring having from 3 to about 7 atoms wherein from 1 to 3 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: November 4, 1997
    Assignee: The Procter & Gamble Company
    Inventor: Michael Wiard Scherz
  • Patent number: 5646121
    Abstract: The present invention relates to novel pseudopeptides with antiviral activity of the general formula (I) ##STR1## in which the substituents have the meaning given in the description, to a process for their preparation, and to their use as antiviral agents, especially against cytomegaloviruses.
    Type: Grant
    Filed: September 7, 1994
    Date of Patent: July 8, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Habich, Thomas-J. Schulze, Jurgen Reefschlager, Jutta Hansen, Rainer Neumann, Gert Streissle, Arnold Paessens
  • Patent number: 5637719
    Abstract: The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: June 10, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Michael Philbin
  • Patent number: 5633231
    Abstract: The present invention relates to valine-containing, substituted pseudopeptides of the general formula (I) ##STR1## in which the substituents have the meaning given in the description, to processes for their preparation, and to their use as anti-viral agents, in particular against cytomegaloviruses.
    Type: Grant
    Filed: September 7, 1994
    Date of Patent: May 27, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Habich, Thomas J. Schulze, Jurgen Reefschlager, Jutta Hansen, Rainer Neumann, Gert Streissle, Arnold Paessens
  • Patent number: 5591833
    Abstract: Colorants and compositions useful as a fugitive or permanent colorant for a variety of substrates, or as intermediates for their manufacture, and having one or more improved properties of enhanced aqueous washability, compatibility with and non-extractibility from thermoplastic resins, or reactivity with resins having reactive functionality, said composition having the formula C(Z).sub.
    Type: Grant
    Filed: August 10, 1993
    Date of Patent: January 7, 1997
    Assignee: Milliken Research Corporation
    Inventors: John B. Hines, David J. Moody, Edward W. Kluger
  • Patent number: 5567827
    Abstract: The subject of the invention is 4-hydroxyphenylthio derivatives of general formula: ##STR1## in which: R.sub.1 and R.sub.2, which are identical or different, each represent hydrogen, a methyl or ethyl radical or a halogen atom,R represents a (C.sub.1 -C.sub.6) alkyl, (C.sub.3 -C.sub.6) cycloalkyl or phenyl radical,R.sub.3 represents hydrogen or a halogen atom,X represents --O--, --S-- or --NR.sub.4 -- in which R.sub.4 represents hydrogen or a (C.sub.1 -C.sub.4) alkyl group,useful as synthetic intermediates, especially for the preparation of aminoalkoxyphenylsulphonyl derivatives which are pharmaceutically active compounds.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 22, 1996
    Assignee: Elf Sanofi
    Inventors: Jean Gubin, Henri Inion
  • Patent number: 5547980
    Abstract: Bicyclic sulfones of the formula I ##STR1## in which Y is a halogen atom,Z is a halogen atom or hydrogen,m and n, that are different and represent an integer 0 or 1,A and B each represent hydrogen or together represent a valency bond,X.sub.1 and X.sub.2 each represent NR.sub.1 R.sub.2 or, if A and B represent a valency bond, one of the two residues X.sub.1 or X.sub.2 represents hydrogen and the other represents NR.sub.1 R.sub.2,R.sub.1 denotes a C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl or a benzyl residue substituted if desired, by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or hydroxy andR.sub.2 denotes hydrogen or a residue from the definition of R.sub.1 orR.sub.1 and R.sub.2 together with the nitrogen atom form a heterocyclic ring which if desired, contains further heteroatoms and/or can be substituted by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: August 20, 1996
    Assignee: Boehringer Mannheim GmbH
    Inventors: Walter-Gunar Friebe, Erhard Reinholz, Henning Wilhelms
  • Patent number: 5532254
    Abstract: A method for modulating calcium channels, increasing the density of calcium channels in vascular and cardiac tissue with no changes in inotropic or pressor response, comprising administering to a warm-blooded animal in need thereof a pharmaceutically-effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, C.sub.1 -C.sub.4 alkyl, --CO--(C.sub.1 -C.sub.6 alkyl), or --CH.sub.2 Ar, --CO--Ar, wherein Ar is phenyl or substituted phenyl;R.sup.2 is selected from the group consisting of pyrrolidine, hexamethylenemino, and piperidino; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 2, 1996
    Assignee: Eli Lilly and Company
    Inventor: Nancy L. Bowling
  • Patent number: 5510491
    Abstract: This invention relates to compounds of the formula: ##STR1## wherein R is an electron withdrawing group; R.sub.1 is H or COZ;X.sub.1 and X.sub.2 are independently H, lower alkyl,aryl, aryl lower-alkyl or polystyrene orR and X.sub.1 taken together with the carbon atoms to which they are attached form a ring containing from 4 to 15 ring carbon atoms and may contain up to 2 heteroatoms, wherein the heteroatoms are O, S, or N; andZ is an amino acid residue, a peptide residue or a leaving group. The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is also directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: April 23, 1996
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Michael Philbin
  • Patent number: 5508431
    Abstract: The subject of the invention is 4-hydroxyphenylthio derivatives of general formula: ##STR1## in which: R.sub.1 and R.sub.2, which are identical or different, each represent hydrogen, a methyl or ethyl radical or a halogen atom,R represents a (C.sub.1 -C.sub.6) alkyl, (C.sub.3 -C.sub.6) cycloalkyl or phenyl radical,R.sub.3 represents hydrogen or a halogen atom,X represents --O--, --S-- or --NR.sub.4 -- in which R.sub.4 represents hydrogen or a (C.sub.1 -C.sub.4) alkyl group, useful as synthetic intermediates, especially for the preparation of aminoalkoxyphenylsulphonyl derivatives which are pharmaceutically active compounds.
    Type: Grant
    Filed: September 8, 1994
    Date of Patent: April 16, 1996
    Assignee: Elf Sanofi
    Inventors: Jean Gubin, Henri Inion
  • Patent number: 5498630
    Abstract: A method of controlling Take-All disease of plants by applying a fungicide of the formula ##STR1## wherein Z1 and Z2 are C and are part of an aromatic ring which is benzothiophene; andA is selected from --C(X)-amine wherein the amine is an unsubstituted, monosubstituted or disubstituted amino radical, --C(O)--SR.sub.3, --NH--C(X)R.sub.4, and --C(.dbd.NR.sub.3)--XR.sub.7 ;B is --W.sub.m --Q(R.sub.2).sub.3 or selected from O-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R.sub.4 ;Q is C, Si, Ge, or Sn;W is --C(R.sub.3).sub.p H.sub.(2-p) --; or when Q is C, W is selected from --C(R.sub.3).sub.p H(.sub.2-p), --N(R.sub.3).sub.m H(.sub.1-m)--, --S(O)p--, and --O--;X is 0 or S;n is 0, 1, 2, or 3;m is 0 or 1;p is 0, 1, or 2;each R and R.sub.2 is independently defined herein;R.sub.3 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; andR.sub.7 is C.sub.1 -C.sub.
    Type: Grant
    Filed: November 16, 1994
    Date of Patent: March 12, 1996
    Assignee: Monsanto Company
    Inventors: Dennis P. Phillion, Diane S. Braccolino, Matthew J. Graneto, Wendell G. Phillips, Karey A. Van Sant, Daniel M. Walker, Sai C. Wong
  • Patent number: 5482962
    Abstract: This invention relates to N,N'-disubstituted-N,N'-diacylhydrazines which are useful as insecticides, compositions containing those compounds and methods of their use. This invention also relates to the production of intermediates useful in the production of such compounds.The compounds of this invention may be represented by the formula ##STR1## wherein R.sup.1 is cyano or H,R.sup.2 is branched alkyl,B is aryl or substituted aryl,R.sup.a is H or a variety of substituents, andZ forms a fused 5-member heterocyclic ring.
    Type: Grant
    Filed: July 22, 1994
    Date of Patent: January 9, 1996
    Assignee: Rohm and Haas Company
    Inventor: Robert E. Hormann
  • Patent number: 5441722
    Abstract: This invention concerns the short synthesis of 5,6-dihydro-(S)-4-(ethylamino)-(S)-6-[C.sup.3 H.sub.3 ]-4H-thieno [2,3-b]thiopyran-2-sulfonamide 7,7-dioxide and related non-radioactive and radioactive compounds. The key step is the regioselective and stereo-controlled methylation of the C-6 (.alpha.-sulfone) carbanion in the presence of the monoprotected sulfonamide anion.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: August 15, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Wai-Si Eng, Donald H. Burns, Gerald S. Ponticello, Harold G. Selnick
  • Patent number: 5374644
    Abstract: Compounds of formula: ##STR1## and stereoisomers thereof, wherein X, Y and Z, which are the same or different, are hydrogen, halogen, hydroxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aralkyl, optionally substituted arylalkoxy, optionally substituted aryloxyalkyl, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, cyano, --CO.sub.2 R.sup.1, --CONR.sup.2 R.sup.3, or --COR.sup.
    Type: Grant
    Filed: December 31, 1991
    Date of Patent: December 20, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Ian T. Streeting
  • Patent number: 5356926
    Abstract: 3-Alkyloxy-, aryloxy-, or arylalkyloxybenzo[b]-thiophene-2-carboxamides are described as agents which block leukocyte adherence to vascular endothelium and, as such, are effective therapeutic agents for treating inflammatory diseases. Certain of these compounds are novel and methods of preparation are also described.
    Type: Grant
    Filed: February 9, 1993
    Date of Patent: October 18, 1994
    Assignee: Warner-Lambert Company
    Inventors: Diane H. Boschelli, David T. Connor, Clifford D. Wright
  • Patent number: 5352781
    Abstract: The process of the invention comprises reacting a C-22-halo-23,24-bisnorsteroid or C-22-halo-23,24-bisnor-9,10-secosteroid with a nickel complex of an electron withdrawing alkene of the formula ##STR1## wherein R.sub.1 is hydrogen, hydroxycarbonyl, lower alkoxycarbonyl, lower alkylcarbonyl or unsubstituted or substituted lower alkyl, and R.sub.2 is hydroxyl, lower alkoxy, or unsubstituted or substituted lower alkyl, to yield a C-25 or C-26 precursor of the formula ##STR2## which is appropriately functionalized for conversion into the corresponding steroid or secosteroid by treatment as hereinafter described.
    Type: Grant
    Filed: March 19, 1993
    Date of Patent: October 4, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George P. Yiannikouros, Percy S. Manchand
  • 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: 5288749
    Abstract: The present invention provides tertiary and secondary amine compounds of the formula ##STR1## and the pharmaceutically acceptable salts thereof which are antagonists for alpha-2 adrenoreceptors and which inhibit serotonin (5-hydroxytryptamine, 5-HT) uptake.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: February 22, 1994
    Assignee: Abbott Laboratories
    Inventors: Michael D. Meyer, John F. DeBernardis, Rajnandan Prasad, Kevin B. Sippy, Karin R. Tietje
  • Patent number: 5268388
    Abstract: Certain substituted semicarbazones, including all geometric and stereoisomers thereof, agricultural compositions containing them and their use as arthropodicides.
    Type: Grant
    Filed: November 2, 1992
    Date of Patent: December 7, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John P. Daub, George P. Lahm, Bradford S. Marlin
  • Patent number: 5244893
    Abstract: New compounds of the formula (I) ##STR1## in which R.sup.1 -R.sup.6 have the meanings given in the description, their preparation and use in plant protection, the protection of materials and in the field of human and veterinary medicine.Formula (I) gives a definition of the compounds which can be prepared by analogous processes, for example from suitable benzothiophene derivatives by oxidation.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: September 14, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Ludwig Elbe, Dieter Berg, Heinz-Wilhelm Dehne, Stefan Dutzmann, Georg-Wilhelm Ludwig, Manfred Plempel
  • Patent number: 5221754
    Abstract: This invention relates to compounds of the formula: ##STR1## wherein R is an electron withdrawing group;R.sub.1 is H or COZ;X.sub.1 and X.sub.2 are independently H, lower alkyl, aryl, aryl lower-alkyl or polystyrene or R and X.sub.1 taken together with the carbon atoms to which they are attached form a ring containing from 4 to 15 ring carbon atoms and may contain up to 2 heteroatoms, wherein the heteroatoms are O, S, or N; andZ is an amino acid residue, a peptide residue or a leaving group. The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is also directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.
    Type: Grant
    Filed: September 14, 1992
    Date of Patent: June 22, 1993
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Michael Philbin
  • Patent number: 5220027
    Abstract: This invention provides azamethine compounds represented by the formula (I): ##STR1## wherein X represents ##STR2## R.sub.1 to R.sub.4 represent independently a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, ##STR3## R.sub.5 and R.sub.6 represent independently a hydrogen atom or an alkyl group which may be substituted by a hydroxyl group; R.sub.7 represents a hydrogen atom, an alkyl group, an alkyoxyl group, a hydroxyl group, a halogen atom, a nitro group, a cyano group, ##STR4## wherein -A represents ##STR5## and R and R' represent independently a hydrogen atom or an alkyl group; and R.sub.10 to R.sub.12 represent independently a hydrogen atom or an alkyl group, a process for producing such compounds, and a medium for recording optical information using these compounds.
    Type: Grant
    Filed: April 12, 1991
    Date of Patent: June 15, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takeshi Hioki, Kiyoteru Kojima, Jun Tomioka
  • Patent number: 5208259
    Abstract: The invention concerns a diaryl ether heterocycle of the formula I, or a pharmaceutically-acceptable salt thereof, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is optionally substituted phenylene, or a 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is (1-4C)alkylene and X.sup.2 is oxy, thio, sulphinyl, sulphonyl or imino.The invention also concerns processes for the manufacture of a diaryl ether heterocycle of the formula I, or a pharmaceutically-acceptable salt thereof, and pharmaceutical compositions containing said heterocycle. The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: July 3, 1990
    Date of Patent: May 4, 1993
    Assignees: Imperial Chemical Industries, ICI Pharma
    Inventors: Thomas G. C. Bird, Philip N. Edwards
  • Patent number: 5208253
    Abstract: 3-Alkyloxy-, aryloxy-, or arylalkyloxy-benzo[b]thiophene-2-carboxamides are described as agents which block leukocyte adherence to vascular endothelium and, as such, are effective therapeutic agents for treating inflammatory diseases. Certain of these compounds are novel and methods of preparation are also described.
    Type: Grant
    Filed: February 24, 1992
    Date of Patent: May 4, 1993
    Assignee: Warner-Lambert Company
    Inventors: Diane H. Boschelli, David T. Connor, Clifford D. Wright
  • Patent number: 5182393
    Abstract: The process of the invention comprises reacting a C-22-halo-23,24-bisnorsteroid or C-22-halo-23,24-bisnor-9,10-secosteroid with a nickel complex of an electron withdrawing alkene of the formula ##STR1## wherein R.sub.1 is hydrogen, hydroxycarbonyl, lower alkoxycarbonyl, lower alkylcarbonyl or unsubstituted or substituted lower alkyl, and R.sub.2 is hydroxyl, lower alkoxy, or unsubstituted or substituted lower alkyl,to yield a C-25 or C-26 precursor of the formula ##STR2## which is appropriately functionalized for conversion into the corresponding steroid or secosteroid by treatment as hereinafter described.
    Type: Grant
    Filed: March 11, 1992
    Date of Patent: January 26, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George P. Yiannikouros, Percy S. Manchand
  • Patent number: 5169860
    Abstract: This invention provides the use of certain benzofuransulfonamide, benzothiophenesulfonamide, and indolesulfonamide derivatives in the treatment of susceptible neoplasms in mammals. Also provided are certain novel benzofuransulfonamide and benzothiophenesulfonamide derivatives and their pharmaceutical formulations.
    Type: Grant
    Filed: March 13, 1992
    Date of Patent: December 8, 1992
    Assignee: Eli Lilly and Company
    Inventors: Fariborz Mohamadi, Michael M. Spees
  • Patent number: 5164387
    Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, acyl, lower alkyl or --CHO, --CH.sub.2 OR.sup.10, --COR.sup.7 or OR.sup.13 ; R.sup.2, R.sup.3 and R.sup.4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R.sup.5 and R .sup.6 are, independently, hydrogen or lower-alkyl; R.sup.7 is hydroxy, lower-alkoxy or NR.sup.8 R.sup.9 ; R.sup.8 and R.sup.9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, >CR.sup.14 R.sup.15, --O--, --S--, >SO.sub.2 or >NR.sup.18 ; R.sup.10 and R.sup.18 are, independently, hydrogen, lower-alkyl or acyl; M is --C(R.sup.11)=C(R.sup.12)--, --CONH-- or --NH--CO--; R.sup.11, R.sup.12, R.sup.14 and R.sup.15 are, independently, hydrogen or lower-alkyl, R.sup.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: November 17, 1992
    Assignee: Hoffmann-LaRoche Inc.
    Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
  • Patent number: 5147889
    Abstract: Benzo[b]thiophene derivatives of formula ##STR1## their tautomers and salts, in which the index n is 0, 1 or 2, alk is lower alkylene, Ar is phenyl, naphthyl or a monocyclic, five- or six-membered heteroaryl radical, wherein the aromatic radical is unsubstituted or is mono- or poly-substituted by lower alkyl, halo-lower alkyl, halogen and/or nitro, and the ring A is unsubstituted or is mono- or poly-substituted by lower alkyl, lower alkoxy, lower alkylthio, lower alkanesulfinyl, lower alkanesulfonyl, halo-lower alkyl, halogen and/or by nitro, can be used, for example, as active ingredients in medicaments.
    Type: Grant
    Filed: June 27, 1991
    Date of Patent: September 15, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Pier G. Ferrini
  • Patent number: 5136054
    Abstract: This invention provides azamethine compounds represented by the formula (I): ##STR1## (wherein X represents ##STR2## Y represents C.dbd.O, C.dbd.C(CN).sub.2 or SO.sub.2 ; R.sub.1 to R.sub.4 represent independently a hydrogen atom, an alkyl group which may be substituted, an alkoxyl group which may be substituted, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group which may be substituted, --A--R or ##STR3## R.sub.5 and R.sub.6 represent independently a hydrogen atom, an alkyl group which may be substituted, an aryl group which may be substituted or a cyclohexyl group; R.sub.5 and R.sub.6 may be combined to form a ring or may form a ring with a hetero atom; R.sub.7 and R.sub.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: August 4, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takeshi Hioki, Kiyoteru Kojima, Jun Tomioka
  • Patent number: 5136049
    Abstract: The present invention relates to compounds of formula (I): ##STR1## in which A represents the same or different heteroaryl radicals and substituted heteroaryl radicals; B represents dihydroheteroarenediylidene radicals or substituted dihydroheteroarenediylidene radicals or radicals obtainable from these radicals by oxidation on at least one hetero atom; and R' and R" represent the same or different radicals, in particular hydrogen atoms, C.sub.1 - to C.sub.4 -alkyl radicals or radicals A, or cyano radicals, halogen atoms, radicals of the formula --COOR, or --OR, wherein R is a C.sub.1 - to C.sub.4 -alkyl radical, processes for preparing the same and polymers prepared therefrom.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: August 4, 1992
    Assignee: Wacker-Chemie GmbH
    Inventors: Michael Hanack, Gunter Hieber
  • Patent number: 5128486
    Abstract: A sulpholene compound and more particularly 4,4-dimethyl-2,2-dioxo-1,2,4,5,6,7-hexahydro-benzo[c]thiophene. These compounds are prepared by bringing myrcene sulphone into contact with a strong acid. The compounds of the present invention can be used as synthesis intermediates in the preparation of vitamin A.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: July 7, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventor: Jean-Pierre Duchesne
  • Patent number: 5124499
    Abstract: A sulpholene compound and more particularly 4,4-dimethyl-2,2-dioxo-1,2,4,5,6,7-hexahydro-benzo[c]thiophene. These compounds are prepared by bringing myrcene sulphone into contact with a strong acid. The compounds of the present invention can be used as synthesis intermediates in the preparation of vitamin A.
    Type: Grant
    Filed: August 2, 1991
    Date of Patent: June 23, 1992
    Assignee: Rhone-Poulene Nutrition Animale
    Inventor: Jean-Pierre Duchesne
  • Patent number: 5112852
    Abstract: The present invention relates to allenyl amines, more specifically, .beta.-ethenylidene(substituted) ethanamines, possessing antihypertensive activity, and having the general formula ##STR1## wherein n is the integer 0, 1 or 2; each X independently is a substituent selected from the group consisting of loweralkyl, halo, --O--(loweralkyl), --S--(loweralkyl), --SO--(loweralkyl), --SO.sub.2 --(loweralkyl), CO.sub.2 R and CH.sub.2 OR, wherein R is loweralkyl and each loweralkyl group is from 1 to about 6 carbon atoms, or the pharmaceutically-acceptable addition salts thereof. These compounds are prepared by a novel reaction of a protected N,N-bis(trimethylsilyl)-4-methoxy-2-butynylamine compound with a metallo-organic compound, with subsequent removal of the silyl protecting groups to provide the desired compound.
    Type: Grant
    Filed: April 21, 1989
    Date of Patent: May 12, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: James R. McCarthy, Thomas M. Bargar, Charlotte L. Barney, Donald P. Matthews, Robert J. Broersma
  • Patent number: 5082953
    Abstract: A sulpholene compound and more particularly 4,4-dimethyl-2,2-dioxo-1,2,4,5,6,7-hexahydro-benzo[c]thiophene. These compounds are prepared by bringing myrcene sulphone into contact with a strong acid. The compounds of the present invention can be used as synthesis intermediates in the preparation of vitamin A.
    Type: Grant
    Filed: March 4, 1991
    Date of Patent: January 21, 1992
    Assignee: Rhone Poulenc Nutrition Animale
    Inventor: Jean-Pierre Duchesne
  • Patent number: 5071841
    Abstract: The present invention provides a sulfur-containing heterocyclic compound of the formula (I) ##STR1## wherein ring A is a benzene ring which may be substituted; R is a hydrogen atom or a hydrocarbon group which may be substituted; B is a carboxyl group which may be esterified or amidated; X is --CH(OH)-- or --CO--; k is 0 or 1; and k' is 0, 1 or 2 or a pharmaceutically acceptable salt thereof.Also, it provides a process for producing the compound (I) or a salt thereof and a pharmaceutical preparation for use in the treatment of osteoporosis comprising the compound (I) or salt thereof.The compounds (I) and salts thereof show excellent bone resorption inhibitory activity.
    Type: Grant
    Filed: December 28, 1989
    Date of Patent: December 10, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Takashi Sohda, Masao Tsuda, Iwao Yamazaki
  • Patent number: 5051421
    Abstract: Benzo[b]thiophene derivatives of formula ##STR1## their tautomers and salts, in which the index n is 0, 1 or 2, alk is lower alkylene, Ar is phenyl, naphthyl or a monocyclic, five- or six-membered heteroaryl radical, wherein the aromatic radical is unsubstituted or is mono- or poly-substituted by lower alkyl, halo-lower alkyl, halogen and/or by nitro, and the ring A is unsubstituted or is mono- or poly-substituted by lower alkyl, lower alkoxy, lower alkylthio, lower alkanesulfinyl, lower alkanesulfonyl, halo-lower alkyl, halogen and/or by nitro, can be used, for example, as active ingredients in medicaments.
    Type: Grant
    Filed: January 18, 1990
    Date of Patent: September 24, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Pier G. Ferrini
  • Patent number: 5037825
    Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, acyl, lower-alkyl or --CHO, --CH.sub.2 OR.sup.10, --COR.sup.7 or OR.sup.13 ; R.sup.2, R.sup.3 and R.sup.4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R.sup.5 and R.sup.6 are, independently, hydrogen or lower-alkyl; R.sup.7 is hydroxy, lower-alkoxy or NR.sup.8 R.sup.9 ; R.sup.8 and R.sup.9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, >CR.sup.14 R.sup.15, --O--, --S--, >SO, >SO.sub.2 or >NR.sup.18 ; R.sup.10 and R.sup.18 are, independently, hydrogen, lower-alkyl or acyl; M is --C(R.sup.11).dbd.C(R.sup.12)--, --CONH-- or --NH--CO--; R.sup.11, R.sup.12, R.sup.14 and R.sup.15 are, independently, hydrogen or lower-alkyl, R.sup.
    Type: Grant
    Filed: July 10, 1989
    Date of Patent: August 6, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
  • Patent number: 4791123
    Abstract: There are provided new alkane and alkoxyalkane derivatives of the general formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
    Type: Grant
    Filed: January 22, 1987
    Date of Patent: December 13, 1988
    Assignee: Schering Akt.
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles
  • Patent number: 4636575
    Abstract: Compounds of formula II and X ##STR1## wherein X is O, S, SO.sub.2, methylene, isopropylidene or NCOR.sub.7 where R.sub.7 is alkyl or phenyl, Y is a direct bond or methylene, n is 1 or 2, R.sub.4 is alkyl, phenyl, naphthyl, cycloalkyl, aralkyl, camphoryl, CF.sub.3, CCl.sub.3, F or NH.sub.2 ; or is alkylene, phenylene or naphthylene, R.sub.5 is hydrogen or halogen, R.sub.6 is hydrogen, alkyl, phenyl or cyano, R.sub.8 is substituted phenyl, substituted naphthyl, anthryl or phenanthryl, R.sub.9 is alkyl R.sub.10 is alkyl or substituted phenyl, and R.sub.11 is alkyl, substituted phenyl, naphthyl, camphoryl, alkylene, phenylene or naphthylene, are latent curing catalysts for acid-curable stoving lacquers. They are distinguished by satisfactory solubility in the acid-curable resin systems, can be stored virtually indefinitely in the dark and, when exposed to shortwave light, make it possible to cure the resins by acid catalysts at a relatively low temperature.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: January 13, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Kirchmayr
  • Patent number: 4617407
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.
    Type: Grant
    Filed: August 30, 1984
    Date of Patent: October 14, 1986
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Joshua Rokach
  • Patent number: 4595692
    Abstract: Bicycloheptane substituted ether prostaglandin analogs are provided having the structural formula ##STR1## wherein X is O or ##STR2## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: June 17, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Masami Nakane
  • Patent number: 4588742
    Abstract: Thiabicycloheptane substituted prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
    Type: Grant
    Filed: February 20, 1985
    Date of Patent: May 13, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Masami Nakane
  • Patent number: 4548948
    Abstract: Compounds of formula (I): ##STR1## wherein: Ar is phenyl optionally substituted in the o-, m- or p-position by C.sub.1-4 alkyl, C.sub.1-4 alkoxy, trifluoromethyl, bromo, chloro or fluoro,pyrryl optionally N-substituted by C.sub.1-4 alkyl,2-furyl or 2-thienyl either optionally substituted in the 3-, 4- or 5-position by methyl, chloro or bromo, or3-furyl or 3-thienyl;X is oxygen, sulphur, sulphoxide or sulphone, Y is methylene, R.sub.1 and R.sub.3 are hydrogen or C.sub.1-4 alkyl, and R.sub.2 is hydrogen, C.sub.1-4 alkyl, fluoro, chloro or bromo, or X is methylene, Y is oxygen, R.sub.1 and R.sub.3 are both hydrogen, and R.sub.2 is hydrogen, fluoro, chloro or bromo; andR.sub.4 is hydrogen or C.sub.1-4 alkyl, or a salt thereof, have analgesic and/or anti-inflammatory activity.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: October 22, 1985
    Assignee: Beecham Group p.l.c.
    Inventors: Robert W. Ward, Stephen A. Smith, Roger E. Markwell