Halogen Patents (Class 562/472)
  • Patent number: 7385082
    Abstract: The invention relates to a method for the preparation of de 1,3-diphenylprop-2-en-1-one substituted on one of the two phenyl groups by a carboxyalkyloxy group or a carboxyalkylthio group.
    Type: Grant
    Filed: July 8, 2004
    Date of Patent: June 10, 2008
    Assignee: GENFIT
    Inventors: Jean-François Delhomel, Karine Caumont-Bertrand
  • Publication number: 20080064748
    Abstract: The invention relates to substituted enaminones of Formula I and their derivatives and the discovery that these compounds modulate the effect of ?-aminobutyric acid (GABA) on the GABAA receptor complex in a therapeutically relevant fashion and may be used to ameliorate CNS disorders amenable to modulation of the GABAA receptor complex.
    Type: Application
    Filed: May 5, 2005
    Publication date: March 13, 2008
    Inventors: Derk J. Hogenkamp, Timothy B.C. Johnstone, Kelvin W. Gee
  • Patent number: 7323591
    Abstract: Therapeutic compounds, methods, and compositions are disclosed herein. These compounds have prostaglandin EP2 activity, and are useful to treat and/or prevent glaucoma and/or ocular hypertension in a mammal.
    Type: Grant
    Filed: January 4, 2007
    Date of Patent: January 29, 2008
    Assignee: Allergan, Inc.
    Inventors: David W. Old, Todd S. Gac, Vinh X. Ngo
  • Patent number: 7301050
    Abstract: The invention features 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs, compositions containing them, and methods of using them as PPAR delta modulators to treat or inhibit the progression of, for example, dyslipidemia.
    Type: Grant
    Filed: September 16, 2004
    Date of Patent: November 27, 2007
    Assignee: Janssen Pharmaceutical N.V.
    Inventors: Gee-Hong Kuo, Rui Zhang, Aihua Wang, Alan R. DeAngelis
  • Patent number: 7087644
    Abstract: The invention relates to compounds of formula (I) as well as the salts and stereoisomers thereof wherein the several variable groups are as defined in the specification and claims. Processes for making these materials, pharmaceutical compositions containing them, and methods for using them for treatment of cardiovascular disorders are also disclosed and claimed.
    Type: Grant
    Filed: August 31, 2000
    Date of Patent: August 8, 2006
    Assignee: Bayer Aktiengesellschaft
    Inventors: Cristina Alonso-Alija, Markus Heil, Dietmar Flubacher, Paul Naab, Josef Pernerstorfer, Johannes-Peter Stasch, Frank Wunder, Klaus Dembowsky, Elisabeth Perzborn, Elke Stahl
  • Patent number: 7005538
    Abstract: This invention relates to novel compounds which are thyroid receptor ligands, preferably antagonists, and to methods for using such compounds in the treatment of cardiac arrhythmias, thyrotoxicosis and subclinical hyperthyrodism.
    Type: Grant
    Filed: November 16, 2000
    Date of Patent: February 28, 2006
    Assignee: Karo Bio AB
    Inventors: Johan Malm, Chris Litten, Theresa Apelqvist, Asa Hedfors, Peter Brandt, Karin Edvinsson, Sandra Gordon
  • Patent number: 6884820
    Abstract: Compounds of the formula where the variables have the meaning defined in the specification are capable of reducing serum glucose levels in diabetic mammals without the undesirable side effect of reducing serum thyroxine levels.
    Type: Grant
    Filed: April 3, 2003
    Date of Patent: April 26, 2005
    Assignee: Allergan, Inc.
    Inventors: Richard L. Beard, Haiqing Yuan, Roshantha A. Chandratratna
  • Patent number: 6869967
    Abstract: Novel compounds of the general formula (I), the use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds and methods of treatment employing these compounds and compositions. The present compounds may be useful in the treatment and/or prevention of conditions mediated by Peroxisome Proliferator-Activated Receptors (PPAR), in particular the PPAR? suptype.
    Type: Grant
    Filed: July 18, 2002
    Date of Patent: March 22, 2005
    Assignee: Novo Nordisk A/S
    Inventors: Lone Jeppesen, Paul Stanley Bury, John Patrick Mogensen, Ingrid Pettersson, Per Sauerberg
  • Patent number: 6864287
    Abstract: The present invention relates to the compounds of the general formula (I) and their salts and stereoisomers for the production of medicaments for the treatment of cardiovascular disorders.
    Type: Grant
    Filed: August 31, 2000
    Date of Patent: March 8, 2005
    Assignee: Bayer Aktiengesellschaft
    Inventors: Cristina Alonso-Alija, Markus Heil, Dietmar Flubacher, Paul Naab, Johannes-Peter Stasch, Frank Wunder, Klaus Dembowsky, Elisabeth Perzborn, Elke Stahl
  • Patent number: 6835848
    Abstract: The present invention relates to a new and industrially advantageous one-pot process for the preparation of alkyl 3-cyclopropyl amino-2-[2,4-dibromo-3-(difluoromethoxy) benzoyl]-2-propenoates of in which R represents methyl or ethyl, which are valuable intermediates for the production of highly active antibacterial quinolone medicaments.
    Type: Grant
    Filed: January 6, 2003
    Date of Patent: December 28, 2004
    Assignees: Ranbaxy Laboratories Limited, Toyama Chemical Co., Ltd.
    Inventors: Prosenjit Bose, Naresh Kumar, Taro Kiyoto
  • Patent number: 6716877
    Abstract: A method for treating a patient having congestive heart failure by administering a therapeutically effective amount of 3′,3,5-triiodothyropropionic acid (TRIPROP) or 3,5,3′,5′-tetraiodothyropropionic acid (TETRAPROP). Also described is a method to lower cholesterol blood levels of a patient by administering a therapeutically effective amounts of TRIPROP or TETRAPROP.
    Type: Grant
    Filed: February 18, 2003
    Date of Patent: April 6, 2004
    Assignee: The Arizona Board of Regents on behalf of the University of Arizona
    Inventor: Eugene Morkin
  • Patent number: 6492424
    Abstract: Novel glucocorticoid and thyroid receptor ligands as provided which have the general formula (I): in which R1 is an aliphatic hydrocarbon, an aromatic hydrocarbon, carboxylic acid or ester thereof, alkenyl carboxylic acid or ester thereof, hydroxy, halogen, or cyano, or a pharmaceutically acceptable salt thereof. R2 and R3 are the same or different, and are hydrogen, halogen, alkyl of 1 to 4 carbons, or cycloalkyl of 3 to 5 carbons, at least one of R2 and R3 being other than hydrogen. X is carbonyl or methylene. R4 is an aliphatic, aromatic or heteroaromatic. Y is hydroxyl, methoxy, amino, or alkyl amino. n is an integer from 0 to 4. A method for treating diseases associated with metabolism dysfunction or which are dependent on the expression of a glucocorticoid or thyroid receptor gene such as diabetes, hypercholesterolemia, or obesity using these compounds is also disclosed.
    Type: Grant
    Filed: April 9, 2001
    Date of Patent: December 10, 2002
    Assignee: Karo Bio AB
    Inventors: Theresa Apelqvist, Patrick Goede, Erik Holmgren
  • Patent number: 6337306
    Abstract: Phenoxyacetic acid derivatives of the formula: wherein R1, R2, Xn and A are as defined herein, and a process for preparing the derivatives. The derivatives are used as herbicides.
    Type: Grant
    Filed: November 5, 1999
    Date of Patent: January 8, 2002
    Assignee: Rhone-Poulenc Agro
    Inventors: Norio Sasaki, Atsushi Go, Hideshi Mukaida, Yukiko Oe
  • Patent number: 6316666
    Abstract: A method for producing phenylenedioxydiacetic acids of high purity at high yield from crude phenylenedioxydiacetic acids which mainly contains phenylenedioxydiacetic acids represented by the following general formula (I): wherein, R represents a hologen, carboxyl group or hydrocarbon group having 1-4 carbon atoms, and n represents an integer from 0 to 3, wherein an alkaline aqueous solution of the crude phenylenedioxydiacetic acids is mixed with a mineral acid to precipitate the phenylenedioxydiacetic acids, wherein at least 10% by weight of the alkaline aqueous solution is mixed with a mineral acid at 0 to 50° C.; and, after completion of the mixing, the temperature of the mixture is kept at 80 to 110° C.
    Type: Grant
    Filed: February 2, 2000
    Date of Patent: November 13, 2001
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Junji Morimoto, Takashi Kamikawa, Hiroshi Ueda
  • Patent number: 6274385
    Abstract: The present invention relates to a process of coding and identifying individual members of a chemical combinatorial library synthesized on a plurality of solid supports which undergo mix and split synthesis. The process provides for tagging the solid supports with a coding identifier that is attached to the solid support and which can be decoded by infrared or raman spectroscopy when directly attached to the support.
    Type: Grant
    Filed: August 9, 1999
    Date of Patent: August 14, 2001
    Assignee: Abbott Laboratories
    Inventors: Jill Edie Hochlowski, Thomas J. Sowin, Daniel W. Norbeck, Anne-Laure Marie Grillot, Rolf E. Swenson
  • Patent number: 6093799
    Abstract: A substrate for solid phase synthesis of the formula: ##STR1## is disclosed. Also disclosed are processes for preparing the substrate and intermediates useful therein. Among the novel intermediates are compounds of the formula: ##STR2## wherein t is 0 or 1; n is 3-20; R is OH, an activated ester or the residue of a solid support having a plurality of amino functionalities; A is --O-- or --NH-- and Q is hydrogen or a protecting group for an amine or alcohol.
    Type: Grant
    Filed: October 20, 1999
    Date of Patent: July 25, 2000
    Assignee: Pharmacopeia, Inc.
    Inventors: Ge Li, Sian Louise Griffiths, Edward McDonald, Libo Xu
  • Patent number: 6048895
    Abstract: The invention provides novel PGF analogs. In particular, the present invention relates to compounds having a structure according to the following formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, X, and Z are as defined. This invention also includes optical isomers, diastereomers and enantiomers of the formula above, and pharmaceutically-acceptable salts, biohydrolyzable amides, esters, and imides thereof.The compounds of the present invention are useful for the treatment of a variety of diseases and conditions, such as bone disorders and glaucoma. Accordingly, the invention further provides pharmaceutical compositions comprising these compounds. The invention still further provides methods of treatment for bone disorders and glaucoma using theses compounds or the compositions containing them.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: April 11, 2000
    Assignee: The Procter & Gamble Company
    Inventors: John August Wos, Mitchell Anthony deLong, Jack S. Amburgey, Jr., Haiyan George Dai, Biswanath De, David Lindsey Soper
  • Patent number: 6008321
    Abstract: A substrate for solid phase synthesis of the formula: ##STR1## is disclosed. Also disclosed are processes for preparing the substrate and intermediates useful therein. Among the novel intermediates are compounds of the formula: ##STR2## wherein t is 0 or 1; n is 3-20; R is OH, an activated ester or the residue of a solid support having a plurality of amino functionalities; A is --O-- or --NH-- and Q is hydrogen or a protecting group for an amine or alcohol.
    Type: Grant
    Filed: March 16, 1998
    Date of Patent: December 28, 1999
    Assignee: Pharmacopeia, Inc.
    Inventors: Ge Li, Sian Louise Griffiths, Edward McDonald, Libo Xu
  • Patent number: 5985927
    Abstract: Medicinal products for the selective control of tumor tissue and a method for control of such tumor tissue by administration of such product to a host. The products comprise: (a) two different compounds having a pH below 7 when the compounds are present in a protonated form, such compounds having the formula set forth below and (b) a pharmaceutically acceptable inert medicinal product carrier. The compounds have the following ##STR1## wherein R.sub.1 is hydrogen or a moiety which completes an ester group or an ether group, R.sub.2 is independently selected from the group consisting of an amino group, hydroxyl, an ester group, an ether group and a halogen, and n is an integer of 1 to 4.
    Type: Grant
    Filed: February 17, 1998
    Date of Patent: November 16, 1999
    Inventor: Werner Kreutz
  • Patent number: 5985920
    Abstract: A fluorine-containing prostaglandin derivative of the formula (1) (or a salt thereof) and a medicine containing it, particularly, a preventive or therapeutic medicine for an eye disease: ##STR1## wherein A is a vinylene group or the like, R.sup.1 is an aryloxyalkyl group or the like, R.sup.2 and R.sup.3 are hydrogen atoms or the like, and Z is OR.sup.4 (wherein OR.sup.4 is a hydrogen atom or an alkyl group) or the like.
    Type: Grant
    Filed: August 3, 1998
    Date of Patent: November 16, 1999
    Assignees: Asahi Glass Company Ltd., Santen Pharmaceutical Co., Ltd.
    Inventors: Eiichi Shirasawa, Masaaki Kageyama, Tadashi Nakajima, Takashi Nakano, Nobuaki Mori, Hideshi Sasakura, Yasushi Matsumura, Yoshitomi Morizawa
  • Patent number: 5766610
    Abstract: Novel pharmaceutically/cosmetically-active polycyclic aromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a)-(e): ##STR2## 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: April 26, 1995
    Date of Patent: June 16, 1998
    Assignee: Centre International De Recherches Dermatologiques Galderma
    Inventor: Jean-Michel Bernardon
  • Patent number: 5512595
    Abstract: New substituted phenoxyisobutyric acids and esters that can be used as medicaments and correspond to the formula: ##STR1## wherein X, A, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and Z are as defined in the description.Those compounds and their physiologically tolerable salts can be used therapeutically.
    Type: Grant
    Filed: April 19, 1994
    Date of Patent: April 30, 1996
    Assignee: Adir et Compagnie
    Inventors: Gilbert Regnier, Claude Guillonneau, Jean-Paul Vilaine, Albert Lenaers, Christine Breugnot
  • Patent number: 5453443
    Abstract: Compounds having the formula I: ##STR1## are inhibitors of the PLA.sub.2 s enzymes. These compounds are useful as anti-allergic, anti-asthmatic, they are also useful in treating various inflammatory diseases such as rheumatoid arthritis, osteoarthritis, bursitis, psoriasis; immunoinflammatory disorders such as contact dermatitis, irritable bowel disease and the like.
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: September 26, 1995
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Helene Perrier, Petpiboon Prasit, Ian Street, Zhaoyin Wang
  • Patent number: 5332857
    Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.
    Type: Grant
    Filed: July 6, 1992
    Date of Patent: July 26, 1994
    Assignee: Pfizer Inc.
    Inventors: Peter A. McCarthy, Frederick J. Walker
  • Patent number: 5290812
    Abstract: Phenoxyalkylcarboxylic acid derivatives represented by the following formula (I) ##STR1## having a strong and selective leukotriene antagonistic action and useful for prophylaxis and therapy of allergic diseases as asthma and processes of preparing the same.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: March 1, 1994
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Mitsuo Ohashi, Toshio Tanaka, Norihisa Ishikawa, Tetsuya Kishi
  • Patent number: 5183925
    Abstract: The invention relates to leukotriene-B.sub.4 derivatives of formula I, ##STR1## in which n=1-10,R.sub.1 means radical CH.sub.2 OH, radical COOR.sub.4, radical CONHR.sub.5 or radical CONR.sub.6 R.sub.7,A means a cis, trans or trans, trans--CH.dbd.CH--CH.dbd.CH group or tetramethylene group,B means an alkylene group with up to 10 C atoms,D means a direct compound, oxygen, sulfur, a --C.tbd.C group or a --CH.dbd.CR.sub.8 group,B and D together mean a direct bond,R.sub.2 means a hydrogen atom or an acid radical of an organic acid with 1-15 C atoms andR.sub.3 means a hydrogen atom, an optionally substituted alkyl radical with 1-10 C atoms,a cycloalkyl radical with 3-10 C atoms, an optionally substituted aryl radical with 6-10 C atoms or a 5-6 member heterocyclic radical and if R.sub.4 means a hydrogen atom, their salts with physiologically compatible bases and their cyclodextrin clathrates, process for their production and their pharmaceutical use.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: February 2, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Rolalnd Ederdt
  • Patent number: 5167696
    Abstract: A compound of formula (I): ##STR1## in which Ar is an optionally substituted aryl or heterocyclic ring system; W is O or NR.sup.1 where R.sup.1 is hydrogen or lower alkyl;A is .dbd.CH or >CH.sub.2 and G is .dbd.C--R.sup.2, >CR.sup.3 R.sup.4 or >C.dbd.R.sup.5 such that --G--A-- is --CR.sup.2 .dbd.CH--, where R.sup.2 is H or CR.sup.6 R.sup.7 XR.sup.8 ; or --G--A-- is CR.sup.3 R.sup.4 --CH.sub.2 where CR.sup.3 R.sup.4 is CH--CR.sup.6 R.sup.7 XR.sup.8, CH--OCR.sup.6 R.sup.7 XR.sup.8, C(R.sup.9)OCOR.sup.10, CR.sup.9 R.sup.10, C(R.sup.9)OR.sup.10, C(OR.sup.9)OR.sup.10, or CH--CH.sub.2 (CO.sub.2 R.sup.11); or --G--A-- is --CR.sup.5 --CH.sub.2 -- where R.sup.5 is .dbd.CR.sup.7 XR.sup.8, .dbd.NOCR.sup.6 R.sup.7 XR.sup.8, .dbd.NOR.sup.11 or .dbd.NOCOR.sup.11 ;X is (CH.sub.2).sub.n, CH.dbd.CH, CH(OR.sup.20)CH.sub.2, or COCH.sub.2 ;n is 0, 1 or 2;R.sup.6 and R.sup.7 are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR.sup.9 R.sup.10, or R.sup.6 and R.sup.
    Type: Grant
    Filed: February 7, 1991
    Date of Patent: December 1, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ewan J. T. Chrystal, John E. D. Barton, David Cartwright
  • Patent number: 5166377
    Abstract: The invention concerns novel 4-phenyl-1,3-dioxan-5-ylalkenoic acid derivatives of the formula I having cis relative stereochemistry at positions 4 and 5 of the dioxane ring and wherein Ra and Rb are variously hydrogen, alkyl, halogenoalkyl, alkenyl, and optionally substituted aryl or arylalkyl, Rc is hydroxy, alkoxy or alkanesulphonamido, n is 1 or 2, A is ethylene or vinylene, Y is (2-5C)polymethylene optionally substituted by alkyl, and benzene ring B is optionally substituted phenyl, or, when Rc is hydroxy, a salt thereof. The acid derivatives antagonize one or more of the actions of thromboxane A.sub.2 (TXA.sub.2) and are expected to be of value in those disease conditions in which TXA.sub.2 is involved. The invention also provides pharmaceutical compositions containing an acid derivative of formula I, and processes for their chemical production.
    Type: Grant
    Filed: February 9, 1988
    Date of Patent: November 24, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Andrew G. Brewster, Peter W. R. Caulkett
  • Patent number: 5151545
    Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.
    Type: Grant
    Filed: March 27, 1990
    Date of Patent: September 29, 1992
    Assignee: Pfizer Inc.
    Inventors: Peter A. McCarthy, Frederick J. Walker
  • Patent number: 5145992
    Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 can be hydrogen, alkyl, alkoxy, halo, phenyl, substituted phenyl, or hydroxy; A can be S, O or --CH.sub.2 --; and Alk is straight or branched chain alkylene, with a base in an aprotic solvent, then reacting the resulting alkoxide with a monohaloacetic acid ester to give an alkoxyacetate followed by reaction of the alkoxyacetate with a hydrogen halide, organic acid or Lewis acid in nitromethane to give the corresponding .alpha.-alkoxyacetic acid which then may be recovered or may optionally be converted to the corresponding salt by contracting the .alpha.-alkoxyacetic acid with a base.
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: September 8, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 5098613
    Abstract: This invention provides benzene derivatives, pharmaceutical formulations of those derivatives, and a method of using the derivatives for the treatment of inflammation in mammals.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: March 24, 1992
    Assignee: Eli Lilly and Company
    Inventors: Nancy G. Bollinger, Theodore Goodson, Jr., David K. Herron
  • Patent number: 5043257
    Abstract: Azo dyes of the formula ##STR1## where X is alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, X' is hydrogen, alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, Y and Y' are independently of each other hydrogen or halogen, Z is hydrogen, alkyl or alkoxy or alkylthio each of 1 to 4 carbon atoms, or halogen, M is a 1-, 2- or 3-valent metal cation, ammonium or an organic ammonium compound, m is 1, 2 or 3 and n is 2 to 10, are suitable for use as image dyes in photographic silver dye bleach materials.The dyes of the invention can also be used to dye textile materials.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: August 27, 1991
    Assignee: Ilford Limited
    Inventors: Kurt Baettig, Gerald C. Jan
  • Patent number: 5041638
    Abstract: An alkenoic acid derivative of the formula ##STR1## in which X and Y are identical or different and represent sulfur, sulfoxide, sulfone, an alkylene chain, --SCH.sub.2 --, or oxygen or a direct bond,W represents --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,o represents a number 1 to 5,A and B are identical or different and represent carboxyl, carboxymethylene, tetrazolyl or tetrazolylmethylene, or --CO.sub.2 R.sup.9 or --CH.sub.2 CO.sub.2 R.sup.9 or --CONR.sup.10 R.sup.11 or nitrilen represents a number 1 to 10,m represents a number 0 to 7,T and Z are identical or different and represent oxygen or a direct bond andR.sup.2, R.sup.3, R.sup.8 are identical or different and represent hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, trifluoromethoxy, cyano or nitro andR.sup.9 is lower alkyl and R.sup.10 and R.sup.11 are hydrogen, lower alkyl, alkylsulfonyl or arylsulfonyl or together are an alkylene chain to form a ringand pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: May 9, 1989
    Date of Patent: August 20, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ulrich Rosentreter, Harold C. Kluender, Trevor S. Abram, Peter Norman, Steven R. Tudhope
  • Patent number: 5021602
    Abstract: Novel compounds have at least one perfluorocyclobutane ring and at least two functional groups suitable for forming condensation polymers. Preferably the compounds have a structures represented by Formula II: ##STR1## wherein R and R' independently represent optionally inertly substituted groups; X and X' represent any molecular structures which link R and R' with the perfluorocyclobutane ring; n and n' are the number of G and G' groups, respectively; and G and G' independently represent any reactive functional groups or any groups convertible into reactive functional groups. The compound are preferably prepared by a process of thermally dimerizing trifluorovinyl compound to form a compounds of Formula IG.sub.n --R--X--CF.dbd.CF.sub.2wherein G represents G or G' in Formula II; X represents X or X' of Formual II; and n represents n or n' of Formula II, to form a compound having a perfluorocyclobutane group.
    Type: Grant
    Filed: June 9, 1989
    Date of Patent: June 4, 1991
    Assignee: The Dow Chemical Company
    Inventors: Katherine S. Clement, David A. Babb, Bobby R. Ezzell
  • Patent number: 5013864
    Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula R--OH wherein R is alkyl, substituted alkyl, or cycloalkyl, or cycloalkyl alkyl with a base in an aprotic organic solvent to give an alkoxide followed by removal of the organic solvent and reaction of the alkoxide with a salt of a monohaloacetic acid in a polar aprotic solvent such as DMSO to give the corresponding alkoxyacetate salt which then may be recovered or may optionally be converted to the corresponding acid by contacting the alkoxy acetate salt with an acid.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: May 7, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Arthur L. Campbell, Richard A. Mueller, John S. Ng, Richard A. Partis
  • Patent number: 5004832
    Abstract: Compounds are described of formula ##STR1## in which: Ar represents an aryl, possibly substituted;R represents a C.sub.1 -C.sub.4 alkyl;R' represents a hydroxyl, an alkoxy, an amino group possibly mono or di-alkyl substituted, or an O.sup.-- M.sup.+ group where M.sup.+ represents the cation of an alkaline metal;X represents a hydrogen, chlorine, bromine or iodine atom, a hydroxyl, or an acyloxy, alkylsulphonyloxy or arylsulphonyloxy group.The compounds of formula I can be easily transformed into alpha-arylalkanoic acids of formula ##STR2## in which Ar and R have the aforesaid meanings.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: April 2, 1991
    Assignee: Zambon S.p.A.
    Inventors: Graziano Castaldi, Claudio Giordano
  • Patent number: 4983629
    Abstract: 11-Haloprostane derivatives of general Formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--group,B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or a --C.tbd.C--group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: January 8, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
  • Patent number: 4937379
    Abstract: A process is described for preparing alpha-arylalkanoic acids, which comprises preparing and subsequently rearranging ketals of formula ##STR1## (in which Ar, R, R.sub.1, R.sub.2 and R.sub.4 have the meanings given in the description).The ketals of formula II are prepared from the corresponding alpha-hydroxyketals.The rearrangement reaction is conducted under mild conditions.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: June 26, 1990
    Assignee: Zambon S.p.A.
    Inventors: Claudio Giordano, Marco Villa
  • Patent number: 4933367
    Abstract: This invention relates to carboxylic acid derivatives and their use thereof. The compounds are useful in treatment of various diseases such as diabetes, prediabetic conditions, adipositas ailments or atherosclerosis.
    Type: Grant
    Filed: March 12, 1987
    Date of Patent: June 12, 1990
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hans P. Wolff, Ernst-Christian Witte, Hans-Frieder Kuhnle
  • Patent number: 4917817
    Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; -X- denotes ##STR2## denotes a single bond, ##STR3## n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.
    Type: Grant
    Filed: July 21, 1988
    Date of Patent: April 17, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
  • Patent number: 4870104
    Abstract: 11-Haloprostane derivatives of general formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH-group,B is a --CH.sub.2 --CH.sub.2 -- or trans-CH.dbd.CH-- or a --C.tbd.C-group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C-bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.
    Type: Grant
    Filed: November 12, 1986
    Date of Patent: September 26, 1989
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
  • Patent number: 4849530
    Abstract: The invention relates to novel crystalline salts of aryloxypropanolamines with diphenylacetic acid, a process for their preparation and the use of these salts for the preparation of chemically pure aryloxy-propanolamines or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: July 18, 1989
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: Gerhard Zol, Gerhard Pfarrhofer
  • Patent number: 4845264
    Abstract: A novel phenoxycarboxylic acid of formula (I) is disclosed. The compound is effective as herbicide for eradicating broad-leaved weeds. A combination of the phenoxycarboxylic acid and a N-phosphonomethylglycine or a glufosinate which is known as a herbicide is very effective for eradicating both broad-leaved weeds and narrow-leaved weeds.
    Type: Grant
    Filed: March 1, 1988
    Date of Patent: July 4, 1989
    Assignee: Teijin Limited
    Inventors: Shizuo Azuma, Toshiyuki Hiramatsu, Koji Nakagawa, Yataro Ichikawa
  • Patent number: 4837342
    Abstract: A prostacyclin analogue having the formula: ##STR1## wherein R.sup.1 is --CO.sub.2 R.sup.5 (wherein R.sup.5 is a hydrogen atom, a straight chain or branched alkyl group having from 1 to 12 carbon atoms, an aralkyl group having from 7 to 12 carbon atoms, a cycloalkyl group having from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, or one equivalent of a cation), or --CONR.sup.6 R.sup.7 (wherein each of R.sup.6 and R.sup.7 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, or R.sup.6 and R.sup.7 together with the adjacent nitrogen atom, form a 5- or 6-membered substituted or unsubstituted hetero ring which may contain a hetero atom other than said nitrogen atom); A is --CH.sub.2 CH.sub.2 CH.sub.2 --, CH.sub.2 --O--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --O--CH.sub.2 -- or --CH.dbd.CHCH.sub.2 CH.sub. 2 --; B is trans --CH.dbd.CH-- or --C.
    Type: Grant
    Filed: February 13, 1987
    Date of Patent: June 6, 1989
    Assignees: Sagami Chemical Research Center, Toa Eiyo Ltd.
    Inventors: Masakatsu Shibasaki, Atsuo Takahashi, Tuyoshi Aoki, Kentaro Kogi, Yozo Nishimiya, Takeshi Nara, Takashi Yamaguchi
  • Patent number: 4814497
    Abstract: Particulate aluminum is intimately mixed with an aromatic material that contains at least one ar-halo substituent having an atomic number above 20 and at least one side-chain halo substituent having an atomic number below 20 in the presence of an aqueous alkali or alkaline earth metal hydroxide so as to effect selective removal of the ar-halo substituent.
    Type: Grant
    Filed: May 12, 1986
    Date of Patent: March 21, 1989
    Assignee: Ethyl Corporation
    Inventor: K. Pushpananda A. Senaratne
  • Patent number: 4808750
    Abstract: Novel fluorophenoxyphenoxypropionates and derivatives thereof possess herbicidal activity selectively in the presence of broadleaf crops. Preemergent and postemergent applications are contemplated.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: February 28, 1989
    Assignee: The Dow Chemical Company
    Inventors: Richard B. Rogers, B. Clifford Gerwick, III
  • Patent number: 4804777
    Abstract: Process for the preparation of an aryloxyacetic acid by oxidation of aryloxyethanol of the formula: ##STR1## wherein m represents 1 or 2,n represents the numeral which results from the difference between 6 and m and R either individually or independently of one another represents hydrogen, alkyl, cycloalky, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen, alkylcarbonyl, arylcarbonyl, carboxyl or nitro, or represents a benzene ring fused to the phenyl ring, in an aqueous alkaline reaction medium at a temperature in the range of 0.degree. C. to the boiling point of the reaction medium in the presence of a catalytic amount of a catalyst comprised of palladium, silver and optionally antimony, and carbon to form the corresponding alkali metal ester and contacting the alkali metal with a mineral acid.
    Type: Grant
    Filed: October 9, 1987
    Date of Patent: February 14, 1989
    Assignee: Eastman Kodak Company
    Inventors: Charles E. Sumner, Jr., Eric J. Fugate
  • Patent number: 4789744
    Abstract: A process for the effective analytical or preparative resolution of the enantiomers of 2-(4-aryloxyphenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof which comprises converting a racemic or partially resolved mixture of said 2-(4-aryloxyphenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof to a pair of diastereomeric terpene esters by reaction with an optically active terpene alcohol and separating the diastereomers of the terpene ester by liquid chromatography with a silica column.
    Type: Grant
    Filed: August 5, 1987
    Date of Patent: December 6, 1988
    Assignee: The Dow Chemical Company
    Inventor: John W. Russell
  • Patent number: 4789685
    Abstract: 9-fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.- position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.
    Type: Grant
    Filed: January 20, 1987
    Date of Patent: December 6, 1988
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
  • Patent number: 4786731
    Abstract: A method for the chromatographic resolution and analysis of the enantiomers of 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof which comprises converting a racemic or partially resolved mixture of said 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof to a pair of diastereomeric 2-amino-1-alkanol derivatives by reaction with an optically active 2-amino-1-alkanol, and analyzing the diastereomeric mixture by gas chromatography.
    Type: Grant
    Filed: August 5, 1987
    Date of Patent: November 22, 1988
    Assignee: The Dow Chemical Company
    Inventor: John W. Russell