Halogen Attached Directly Or Indirectly To The Bicyclo Ring System By Nonionic Bonding Patents (Class 549/56)
  • Patent number: 8574607
    Abstract: Compounds of the formula (I) useful as pesticides are disclosed, wherein the substituents are as defined in claim 1.
    Type: Grant
    Filed: May 21, 2010
    Date of Patent: November 5, 2013
    Assignee: Syngenta Crop Protection, Inc.
    Inventors: Jürgen Harry Schaetzer, Thomas Pitterna, Long Lu, Yaming Wu, Peter Renold, Francesca Perruccio, Jérome Yves Cassayre, Michel Mueglebach
  • Patent number: 8129425
    Abstract: The present invention makes available methods and reagents for modulating proliferation or differentiation in a cell or tissue comprising contacting the cell with a hedgehog agonist, such as the compounds depicted in FIGS. 32 and 33. In certain embodiments, the methods and reagents may be employed to correct or inhibit an aberrant or unwanted growth state, e.g., by antagonizing a normal ptc pathway or agonizing smoothened or hedgehog activity.
    Type: Grant
    Filed: April 27, 2006
    Date of Patent: March 6, 2012
    Assignee: Curis, Inc.
    Inventors: Anthony David Baxter, Edward Andrew Boyd, Maria Frank-Kamenetsky, Oivin Guicherit, Jeffery Porter, Stephen Price, Lee Rubin, John Harry Alexander Stibbard
  • Patent number: 7115653
    Abstract: The present invention makes available methods and reagents for modulating proliferation or differentiation in a cell or tissue comprising contacting the cell with a hedgehog agonist, such as the compounds depicted in FIGS. 32 and 33. In certain embodiments, the methods and reagents may be employed to correct or inhibit an aberrant or unwanted growth state, e.g., by antagonizing a normal ptc pathway or agonizing smoothened or hedgehog activity.
    Type: Grant
    Filed: September 17, 2002
    Date of Patent: October 3, 2006
    Assignee: Curis, Inc.
    Inventors: Anthony David Baxter, Edward Andrew Boyd, Maria Frank-Kamenetsky, Oivin Guicherit, Jeffery Porter, Stephen Price, Lee L. Rubin, John Harry Alexander Stibbard
  • Patent number: 6399788
    Abstract: A process for preparing a compound having PGD2 antagonism represented by the formula (I), or a pharmaceutically acceptable salt or hydrate thereof, which process comprises reacting an amino alcohol of the formula (II) or its salt with a compound of the formula (III) or its reactive derivative, oxidizing the product with halo oxoacid in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyls, reacting the product with an ylide under the conditions for Wittig reaction, and optionally deprotecting the product.
    Type: Grant
    Filed: September 29, 2000
    Date of Patent: June 4, 2002
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tsunetoshi Honma, Yoshiharu Hiramatsu, Tetsuo Okada, Makoto Kakinuma
  • Patent number: 6316487
    Abstract: The subject invention pertains to novel compounds, and compositions comprising the compounds, for the treatment of cardiac arrhythmias. The subject invention further concerns a method of making the novel compounds. The novel compounds are rapidly metabolized analogs of amiodarone, having the distinct and advantageous characteristic of being metabolized to a less lipophilic compound. The new compounds can have particular utility for treating life-threatening ventricular tachyarrhythmias, especially in patients with congestive heart failure (CHF). The product can also provide effective management for ventricular arrhythmias and supraventricular arrhythmias, including atrial fibrillation and re-entrant tachyarrhythmias involving accessory pathways.
    Type: Grant
    Filed: October 6, 2000
    Date of Patent: November 13, 2001
    Assignee: Aryx Therapeutics
    Inventors: Pascal Druzgala, Peter G. Milner
  • Patent number: 6130240
    Abstract: Described is a novel compound and method, useful for treatment of cardiac arrhythmias, especially useful in patients with congestive heart failure (CHF). A process for synthesizing the novel compound is also described.
    Type: Grant
    Filed: December 14, 1998
    Date of Patent: October 10, 2000
    Assignee: Aryx Therapeutics, Inc.
    Inventor: Pascal Druzgala
  • Patent number: 6063936
    Abstract: An aromatic carboxylic acid bicyclic sulfur compound of the following formula: ##STR1## wherein X.sup.1 is selected from the group consisting of C.sub.1 to C.sub.4 alkyl, halogen, C.sub.1 to C.sub.4 haloalkyl, C.sub.2 to C.sub.4 alkoxyalkyl, C.sub.1 to C.sub.4 alkoxy and C.sub.1 to C.sub.4 haloalkoxy; each of X.sup.2 and X.sup.3 is independently selected from the group consisting of hydrogen, C.sub.1 to C.sub.4 alkyl and C.sub.1 to C.sub.4 haloalkyl; X.sup.4 is selected from the group consisting of hydrogen, halogen, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl and C.sub.1 to C.sub.4 alkoxy; each of X.sup.5, X.sup.6, X.sup.7 and X.sup.8 is independently hydrogen or C.sub.1 to C.sub.4 alkyl; the bond between X.sup.2 and X.sup.5 is saturated or unsaturated; the bond between X.sup.5 and X.sup.7 is saturated or unsaturated; p is an integer of 0 or 1; and n is an integer of 0, 1 or 2; or a salt thereof.
    Type: Grant
    Filed: December 15, 1997
    Date of Patent: May 16, 2000
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Kazufumi Nakamura, Masashi Sakamoto, Ichiro Nasuno
  • Patent number: 5989451
    Abstract: This invention provides chiral thioindigo compounds for doping smectic liquid crystal hosts, wherein the compounds modulate a chiral bulk property of an induced chiral smectic liquid crystal phase upon irradiation at a wavelength in the visible range. Modulation of the chiral bulk property is effected by reversible trans-cis photoisomerization of the compound upon irradiation. The compounds maintain their rod-like shape in both isomeric forms, and hence do not destabilize the chiral smectic liquid crystal phase. Compounds according to the invention are useful in optical devices such as optical switches, displays, and memory.
    Type: Grant
    Filed: February 6, 1998
    Date of Patent: November 23, 1999
    Assignee: Queen's University at Kingston
    Inventors: Robert P. Lemieux, Liviu Dinescu
  • Patent number: 5986109
    Abstract: A compound of fomula XIV: ##STR1## wherein: R.sup.1a is --H or --OR.sup.7a in which R.sup.7a is a hydoxy protecting group;R.sup.2a is --H, halo, or OR.sup.8a in which R.sup.8a is a hydroxy protecting group; andR.sup.
    Type: Grant
    Filed: June 18, 1998
    Date of Patent: November 16, 1999
    Assignee: Eli Lilly and Company
    Inventors: Alan David Palkowitz, Kenneth Jeff Thrasher
  • Patent number: 5981766
    Abstract: 4,4'-Dimethyl-6,6'-dichlorothioindigo is obtained in the stable crystal modification I, distinguished by the fraction angles (2 theta):lines of high intensity: 25.99; 27.26lines of moderate intensity: 10.27; 12.48; 22.39; 23.91; 24.82; 28.87,by oxidizing 3-hydroxy-4-methyl-6-chlorothionaphthene having a mean particle size of at most 20 .mu.m.
    Type: Grant
    Filed: January 20, 1999
    Date of Patent: November 9, 1999
    Assignee: Clariant GmbH
    Inventors: Wolfgang Bauer, Uwe Baeumler, Hans Kurz, Hans-Peter Kreutzer
  • Patent number: 5981755
    Abstract: The invention concerns tachykinin antagonists. The compounds are nonpeptides which have utility in treating disorders mediated by tachykinins. Such disorders are respiratory, inflammatory, gastrointestinal, ophthalmic, allergies, pain, vascular, diseases of the central nervous system, and migraine. Methods of preparing compounds and novel intermediates are also included. The compounds are expected to be especially useful in asthma and rheumatoid arthritis.
    Type: Grant
    Filed: October 8, 1998
    Date of Patent: November 9, 1999
    Assignee: Warner-Lambert Company
    Inventors: David Christopher Horwell, William Howson, Martyn Clive Pritchard, Edward Roberts, David Charles Rees
  • Patent number: 5977098
    Abstract: The invention provides a compound of formula I: ##STR1## or a pharmaceutically acceptable salt or solvate thereof; pharmaceutical formulations containing a compound of formula I, and methods of using a compound of formula I for the inhibition of bone loss or bone resorption and for treatment of cardiovascular-related pathological conditions.
    Type: Grant
    Filed: June 30, 1998
    Date of Patent: November 2, 1999
    Assignee: Eli Lilly and Company
    Inventor: Alan David Palkowitz
  • Patent number: 5952513
    Abstract: The instant invention provides novel benzo?b!thiophene compounds, intermediates, compositions, pharmaceutical formulations, and methods of use.
    Type: Grant
    Filed: June 30, 1998
    Date of Patent: September 14, 1999
    Assignee: Eli Lilly and Company
    Inventor: Alan David Palkowitz
  • 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: 5843965
    Abstract: The instant invention provides novel benzo?b!thiophene compounds, intermediates, compositions, pharmaceutical formulations, and methods of use for the inhibition of bone loss or bone resorption and for treatment of cardiovascular-related pathological conditions.
    Type: Grant
    Filed: August 27, 1997
    Date of Patent: December 1, 1998
    Assignee: Eli Lilly and Company
    Inventor: Alan David Palkowitz
  • Patent number: 5663375
    Abstract: Pharmaceutical compounds of the formula ##STR1## in which n is 0, 1 or 2 and R.sup.1 is attached at any of the positions 7, 8, 9 or 10, and each R.sup.1 is halo, carboxy, trifluoromethyl, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, hydroxy-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkoxy, nitrogen-containing heterocyclyl, nitro, trifluoromethoxy, --COOR.sup.5 where R.sup.5 is an ester group, --COR.sup.6, --CONR.sup.6 R.sup.7 or --NR.sup.6 R.sup.7 where R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl;R.sup.2 is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R.sup.2 is furanyl optionally substituted with C.sub.1-4 alkyl;R.sup.3 is nitrile, carboxy, --COOR.sup.8 where R.sup.8 is an ester group, or --CONR.sup.9 R.sup.10 where R.sup.9 and R.sup.10 are each hydrogen or C.sub.1-4 alkyl; andR.sup.4 is --NR.sup.11 R.sup.12, --NR.sup.11 COR.sup.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: September 2, 1997
    Assignees: Eli Lilly and Company, Lilly Industries Limited
    Inventors: Michael Brunavs, Colin Peter Dell, Peter Thaddeus Gallagher, William Martin Owton, Colin William Smith
  • Patent number: 5635527
    Abstract: A novel carboxylic acid compound having a condensed ring, which is represented by the formula (I) ##STR1## wherein each symbol is as defined in the specification, a pharmacologically acceptable salt thereof, a pharmaceutical composition thereof and pharmaceutical use thereof. The novel carboxylic acid compound having a condensed ring and pharmacologically acceptable salt thereof of the present invention have superior GPIIb/IIIa antagonism in mammals inclusive of human; can be administered orally; have long life in blood and low toxicity; and show less side-effects. Accordingly, they are extremely useful for the prophylaxis and treatment of thrombotic diseases and other diseases.
    Type: Grant
    Filed: February 6, 1996
    Date of Patent: June 3, 1997
    Assignee: The Green Cross Corporation
    Inventors: Shinichiro Ono, Tomohiro Yoshida, Atsuyuki Ashimori, Keigo Kosaka, Takehiro Okada, Kazuhiro Maeda, Masahiro Eda, Fumio Mori, Yoshihisa Inoue, Hajime Ebisu, Teruaki Imada, Ruriko Ikegawa, Feng Wang, Norifumi Nakamura
  • Patent number: 5569772
    Abstract: The present invention is directed to a new process for the synthesis of 2-aryl benzo[b]thiophenes, and to novel intermediates therefor.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 29, 1996
    Assignee: Eli Lilly and Company
    Inventors: David W. Hoard, Wayne D. Luke
  • 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: 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: 5426191
    Abstract: An improved process for the preparation of 3-chlorobenzo[b]thiophene-2-carbonyl chlorides is described where a cinnamic acid is converted in the presence of thionyl chloride and a 4-N,N'-disubstituted aminopyridine in one step to the desired product.
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: June 20, 1995
    Assignee: Warner-Lambert Company
    Inventor: Jonathan Walker
  • Patent number: 5378699
    Abstract: Methods of treating an immune disease, cell proliferation, restenosis and vascular smooth muscle cells using the pharmaceutical compounds of the formula ##STR1## in which R.sup.2 is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R.sup.2 is furanyl optionally substituted with C.sub.1-4 alkyl; and salts thereof.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: January 3, 1995
    Assignees: Lilly Industries Limited, Eli Lilly and Company
    Inventors: Michael Brunavs, Colin P. Dell, Peter T. Gallagher, William M. Owton, Jai P. Singh, Colin W. Smith
  • 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: 5252749
    Abstract: The compounds of the invention having the formula: ##STR1## in which: A, which is a ring condensed with cyclopentane, represents a substituted or unsubstituted thiophene ring, Q represents an alkylene chain, R.sub.1 and R.sub.2 each represent H or an alkyl, or they form, with the nitrogen atom to which they are linked, a saturated nitrogenous heterocyclic ring containing 5 to 7 atoms, R.sub.3 and R.sub.4 each represent H, alkyl, cycloalkyl, trifluoromethyl or an optionally substituted phenyl, thienyl or furyl group or R.sub.3 and R.sub.4 together form a (C.sub.5 -C.sub.8) cycloalkyl, as well as their addition salts with an acid and their quaternary ammonium derivatives.They can be used as medicines.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: October 12, 1993
    Assignee: Elf Sanofi
    Inventors: Alain Badorc, Jean Courregelongue, Daniel Ducros, Daniel Frehel, Antonina Giudice, Claudine Serradeil-Legal
  • 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: 5180735
    Abstract: The present invention relates to a compound of the formula: ##STR1## wherein A is halogen, N(O)mR.sup.1 R.sup.2, N.sup..sym. R.sup.1 R.sup.2 R.sup.3 .multidot.X.sup..crclbar., S(O)nR.sup.1 or S.sup..sym. (O)mR.sup.1 R.sup.2 .multidot.X.sup..crclbar. where R.sup.1, R.sup.2 and R.sup.3 are each optionally substituted hydrocarbon or heterocyclic group, X.sup..crclbar. is a counter anion; m is an integer of 0 or 1; n is an integer of 0 to 2; R.sup.1 and R.sup.2 may form a nitrogen-containing or a sulfur-containing heterocyclic ring, which may further form a condensed ring, with the adjacent nitrogen atom or sulfur atom, and these nitrogen-containing or sulfur-containing heterocyclic rings may have substituents, Z is O or NR.sup.4 where R.sup.
    Type: Grant
    Filed: August 29, 1990
    Date of Patent: January 19, 1993
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shoji Kishimoto, Shogo Marui, Takeshi Fujita
  • 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: 5125954
    Abstract: The present invention relates to novel bicyclo ether derivatives, to compositions containing them, and to their method of use especially to control the growth of undesired vegetation in rice.
    Type: Grant
    Filed: November 2, 1990
    Date of Patent: June 30, 1992
    Assignee: E.I. Du Pont de Nemours and Company
    Inventors: James E. Powell, Richard B. Phillips
  • Patent number: 5112851
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 represents a group of formula ##STR2## and R.sub.2 represents hydrogen or lower alkyl, orR.sub.1 and R.sub.2 together with the carbon atom to which they are attached represent a group of formula IIg ##STR3## R.sub.4 and R.sub.5 represents independently hydrogen or lower alkyl, R.sub.3 represents hydrogen, alkyl, cycloalkyl or halogenalkyl andR.sub.6 represents a group of formula ##STR4## R.sub.1 represents a group of formula IIa to IIf as defined above, R.sub.2 and R.sub.3 together form a --(CH.sub.2)--.sub.u group wherein u stands for a whole number from 1 to 8 and R.sub.4, R.sub.5 and R.sub.6 have the meanings given above,which compounds are indicated for use as pharmaceuticals and agrochemicals.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: May 12, 1992
    Assignee: Sandoz Ltd.
    Inventors: Anton Stutz, Peter Nussbaumer
  • 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: 5110829
    Abstract: 2,2'-Thienylbenzothiophenes of the general formula I ##STR1## where R.sup.1 and R.sup.3 independently of one another are each halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, R.sup.2 is hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, n is 0, 1 or 2, and the radicals may be different when n is 2, and m is 0, 1, 2, 3 or 4, and the radicals may be different when m is 2, 3 or 4, processes for their preparation, pesticides containing them and the use thereof.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: May 5, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Reiner Kober, Hans Theobald, Uwe Kardorff, Christoph Kuenast, Peter Hofmeister, Rainer Seele, Gerhard Wagenblast
  • 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: 4853149
    Abstract: Heterocyclic liquid crystal compounds containing the structural element ##STR1## wherein M is H, CN,, NCS, halogen or an alkyl group with 1-5 C atoms,X is CR.sup.4 or N,Y is CHR.sup.4, O, S or NR.sup.5,R.sup.4 is H, alkyl with 1-15 C atoms, halogen or cyano andR.sup.5 is H or alkyl with 1-15 C atoms,with the proviso that in the case where Y=CHR.sup.4, X is N, are suitable as components of liquid crystal phases.
    Type: Grant
    Filed: October 26, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Joachim Krause, Andreas Wachtler, Bernhard Scheuble, Georg Weber
  • Patent number: 4801702
    Abstract: A process for the preparation and conditioning of organic pigments, which comprises the use of at least one tricyclodecane alcohol or tricyclodecene alcohol.
    Type: Grant
    Filed: October 30, 1986
    Date of Patent: January 31, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Fridolin Babler
  • 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: 4742077
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 represents a group of formula ##STR2## whereby R.sub.4 and R.sub.5 are the same or different and represent hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl and X represents oxygen, sulfur, imino, lower alkylimino, --(CH.sub.2)--, --(S.CH.sub.2)-- or --(O.CH.sub.2)--,R.sub.2 represents hydrogen or lower alkyl,R.sub.3 represents a group of formula ##STR3## whereby R.sub.6, R.sub.7 and R.sub.8 are the same or different and represent hydrogen or alkyl or R.sub.6 together with R.sub.7 or R.sub.7 together with R.sub.8 represent --(CH.sub.2).sub.m -- wherein m is 3 to 6,R.sub.9 represents alkyl, alkenyl, trialkylsilyl or alkyl substituted by hydroxy, lower alkoxy, lower halogenalkyl or aryl andn stands for 1, 2 or 3,which possess pharmaceutical in particular antimycotic activity as well as activity against phytopathogenic fungi.
    Type: Grant
    Filed: September 8, 1986
    Date of Patent: May 3, 1988
    Assignee: Sandoz Ltd.
    Inventor: Anton Stutz
  • Patent number: 4664693
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: A is selected from CH and N;B is selected from oxygen, sulfur, CH.sub.2 and the group N-Z wherein Z is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, benzyl and substituted benzyl;X, which may be the same or different, and X.sup.1, which be the same or different, are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.
    Type: Grant
    Filed: April 13, 1984
    Date of Patent: May 12, 1987
    Assignee: ICI Australia Limited
    Inventors: Graham J. Bird, Graeme J. Farquharson, Keith G. Watson, Murray L. Whitelaw
  • Patent number: 4663344
    Abstract: 3-Hydroxybenzo[b]thiophene derivatives, such as 2-aralkyl, 2-alkyl and 2-alkenyl-3-hydroxybenzo[b]-thiophenes, were prepared by, among other methods, ring closure of 2-(2-carboxy-phenylthio)-.alpha.-substituted acetic acids. These compounds are found to be useful in the treatment of pain, fever, inflammation, arthritic conditions, asthma, allergic disorders, skin diseases, cardiovascular disorders, psoriasis, inflammatory diseases and other prostaglandin and/or leukotriene mediated diseases.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: May 5, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Philippe L. Durette, Bruce E. Witzel, Kathleen M. Rupprecht, Allan N. Tischler, Timothy F. Gallagher
  • Patent number: 4652660
    Abstract: Process for preparing thioindigo compounds of the formula ##STR1## in which A and B denote identical or different, optionally substituted benzene rings or benzene rings to which may be joined further carbocyclic and heterocyclic rings,characterized in that compounds of the formulae ##STR2## in which A and B have the abovementioned meaning andX denotes halogen, such as bromine and preferably chlorine,are reacted in a liquid mixture of an aluminium halide, an alkali metal halide and a carboxamide or sulphonamide, and the resulting intermediate product is subsequently, if desired after prior isolation, oxidized in a manner known per se, and the batch is worked up for the compounds of the formula (I).
    Type: Grant
    Filed: July 15, 1985
    Date of Patent: March 24, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Detlef-Ingo Schutze, Klaus Wunderlich
  • Patent number: 4617403
    Abstract: Process for preparing a strong, non-flocking and rheologically excellent 4,4',7,7'-tetrachlorothioindigo pigment in high yields and high purity, which comprises(a) reacting 2,5 -dichlorophenylthioglycoloyl chloride with Friedel-Crafts catalysts in inorganic acyl halides of medium oxidation state as diluent as temperatures of -20.degree. to +50.degree. C. to 4,7-dichloro-3-oxythionaphthene,(b) oxidizing the resulting 4,7-dichloro-3-oxythionaphthene in a conventional manner to crude 4,4',7,7'-tetrachlorothioindigo, and(c) treating the crude 4,4',7,7'-tetrachlorothioindigo obtained in moist form with an aromatic solvent at 80.degree. to 180.degree. C. in the presence of an aqueous alkali solution and a surface-active compound.
    Type: Grant
    Filed: July 5, 1984
    Date of Patent: October 14, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Manfred Urban
  • Patent number: 4456762
    Abstract: The invention provides a process for the preparation of 4,7-dichloro-3-hydroxy-thionaphthene by reaction of 2,5-dichlorophenyl-thioglycolic acid chloride in dichloromethane in the presence of Friedel-Crafts catalysts.
    Type: Grant
    Filed: June 1, 1982
    Date of Patent: June 26, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Manfred Urban
  • Patent number: 4431824
    Abstract: 4,4',7,7'-Tetrachlorothioindigo pigments of high color strength are prepared by oxidizing 3-hydroxy-4,7-dichlorothionaphthene or a mixture of tetrachlorothioindigo and hydroxydichlorothionaphthene in aqueous alkaline suspension with a salt of a nitro-aromatic sulfonic acid, in the presence of a high-boiling, water-immiscible or only slightly water-miscible aromatic liquid, at from 40.degree. to 100.degree. C., and heating the organic suspension to 110.degree.-180.degree. C. Pigmentary forms of tetrachlorothioindigo are isolated which give deep colorations of high brilliance when reduced with white pigments.
    Type: Grant
    Filed: January 6, 1982
    Date of Patent: February 14, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hoch, Heinrich Hiller
  • Patent number: 4424231
    Abstract: There are described compounds of formula I, ##STR1## in which Ra, Rb, Rc, Rd, Re, Rf and Rg, which may be the same or different, each represent hydrogen, amino, hydroxy, alkoxy, alkenyloxy, halogen, acyl, alkenyl, alkyl, or alkoxy substituted by phenyl,Rh is hydrogen, alkyl or --COOH.X is a hydrocarbon chain containing from 2 to 10 carbon atoms and optionally substituted by a hydroxy group,A has no significance or represents Y, OY, or SY and Y represents a C 1 to 4 hydrocarbon chain which is optionally substituted by alkyl C 1 to 4,E and G, which may be the same or different, each represent --O--, --S-- or --CH.sub.2 --, provided that at least one of E and G is --O-- or --S--,L, together with the carbon atoms to which it is attached, forms a benzene, furan, thiophene, pyrrole, or pyran-2-one ring,and pharmaceutically acceptable derivatives thereof.
    Type: Grant
    Filed: March 19, 1982
    Date of Patent: January 3, 1984
    Assignee: Fisons Limited
    Inventors: John R. Bantick, John Fuher, David N. Hardern, Thomas B. Lee
  • Patent number: 4391627
    Abstract: Novel N-(heterocyclicaminocarbonyl)carbonyl-substituted benzothiophene- and benzofuransulfonamides are useful as herbicides. The invention also includes novel sulfonamides and sulfonyl isocyanates useful in preparing such compounds.
    Type: Grant
    Filed: June 22, 1981
    Date of Patent: July 5, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: George Levitt
  • Patent number: 4362740
    Abstract: New spiro compounds of the formula: ##STR1## wherein n is an integer of 1 to 4, and X is halogen, lower alkyl, nitro, amino which may be substituted, hydroxyl which may be substituted, acyl, carboxyl, lower alkoxycarbonyl, carbamoyl which may be substituted, sulfamoyl which may be substituted, lower alkylthio or lower alkylsulfonyl, or two of X at the 5- and 6-positions together form --CH.dbd.CH--CH.dbd.CH--, exhibit inhibitory activity to thrombocyte aggregation and are useful for the prophylaxis or treatment of cardiovascular disturbance such as thrombosis.
    Type: Grant
    Filed: September 19, 1980
    Date of Patent: December 7, 1982
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Isuke Imada, Hirosada Sugihara, Mitsuru Kawada
  • Patent number: 4332955
    Abstract: A transparent pigmentary form of 4,4',7,7'-tetrachlorothioindigo is prepared by oxidizing the leuco compound of tetrachlorothioindigo in aqueous alkaline suspension, in the presence of a dithionite, at from 20.degree. to 100.degree. C., with simultaneous exposure to shearing forces. Preferably, the oxidation is carried out in the presence of a surfactant.The pigment obtained gives brilliant, transparent full-shade colorations, while white reductions have a deep pure reddish hue.
    Type: Grant
    Filed: April 7, 1980
    Date of Patent: June 1, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hoch, Erwin Hahn, Heinrich Hiller
  • Patent number: 4304919
    Abstract: The invention relates to asymmetrical thioindigo compounds of the formula I ##STR1## wherein at least one substituent R is different from a substituent R' and preferably at most three Rs or R's are different from hydrogen, e.g. the compound (I), wherein theRs and R's in the positions 4, 6, 7, 4', 6' and 7' are hydrogen, the R in position 5 is methyl and the R' in position 5' is --(CH.sub.2) OCOCH.sub.3. These compounds can be obtained by a novel process in simple and economic manner and in high purity by reacting a compound of the formula II ##STR2## (wherein X is halogen) with corresponding thiophenols, and cyclising the unsubstituted or substituted 2-thiophenyl-carboxymethylene-benzothiophen-3-ones thereby obtained. Some of the compounds of the formula I are known per se and they are used, inter alia, as disperse, melt spinning and pigment dyes.
    Type: Grant
    Filed: July 14, 1980
    Date of Patent: December 8, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Niklaus Buhler, Hans Bosshard
  • Patent number: 4183842
    Abstract: A method for clear-coloring of linear aromatic polyesters, which comprises mixing at least one pigment selected from the group consisting of a pigment of the formula ##STR1## and pigments of the formula ##STR2## wherein X.sub.1 and X.sub.2 represent a hydrogen atom, a chlorine atom or a methyl group, and X.sub.3 represents a chlorine atom or a methyl group, with a linear aromatic polyester, and heating the mixture to the melting temperature of the polyester to dissolve or substantially dissolve the pigment in the polyester.
    Type: Grant
    Filed: July 18, 1977
    Date of Patent: January 15, 1980
    Assignee: Dainippon Ink & Chemicals, Inc.
    Inventors: Seibei Ono, Kouichi Shibuya, Hiroshi Marikawa
  • Patent number: RE37087
    Abstract: There are provided new alkane and alkoxyalkane derivatives of the general formula I in which R1, R2, R3, R4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: March 6, 2001
    Assignee: Schering Aktiengesellschaft
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles