SI21096B - Carboxylic acid derivatives that inhibit the binding of integrins to,their receptors - Google Patents

Carboxylic acid derivatives that inhibit the binding of integrins to,their receptors Download PDF

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Publication number
SI21096B
SI21096B SI200100288A SI200100288A SI21096B SI 21096 B SI21096 B SI 21096B SI 200100288 A SI200100288 A SI 200100288A SI 200100288 A SI200100288 A SI 200100288A SI 21096 B SI21096 B SI 21096B
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Slovenia
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amino
chlorobenzyl
oxo
carbonyl
hydroxy
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SI200100288A
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Slovenian (sl)
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SI21096A1 (en
Inventor
Ronald J Biediger
Qi Chen
George W Holland
Jamal M Kassir
Wen Li
Robert V Market
Ian L Scott
Chengde Wu
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Encysive Pharmaceuticals Inc
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Priority claimed from US09/973,142 external-priority patent/US6972296B2/en
Application filed by Encysive Pharmaceuticals Inc filed Critical Encysive Pharmaceuticals Inc
Publication of SI21096A1 publication Critical patent/SI21096A1/en
Publication of SI21096B publication Critical patent/SI21096B/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
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    • C07—ORGANIC CHEMISTRY
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    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/22—Nitrogen and oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
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    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

A method for the inhibition of the binding of alpha4beta1 integrin to its receptors, for example VCAM-1 (vascular cell adhesion molecule-1) and fibronectin; compounds that inhibit this binding; pharmaceutically active compositions comprising such compounds; and to the use of such compounds either as above, or in formulations for the control or prevention of diseases states in which alpha4beta1 is involved.

Claims (6)

Patentni zahtevki 1. Spojina, izbrana iz skupine, v kateri so (3S)-3-[({[l-(2-klorobenzil)-4-hidroksi-5-metil-2-okso-l,2-dihidropiridin-3-il]amino}karbonil)amino]-3-(4-metilfenil)propanojska kislina; (3S)-3-[({[l-(2-klorobenzil)-4-hidroksi-2-okso-2,5,6,7-tetrahidro-lH-ciklopenta[b]piridin-3-il]amino}karbonil)amino]-3-(4-metilfenil)propanojska kislina; in (3 S)-3-[( {[ 1 -(2-klorobenzil)-4-hidroksi-5-metil-2-okso-1,2-dihidropiridin-3-il]amino}karbonil)amino]-3-(3-dietilamino)fenil]propanojska kislina; in njihove farmacevtsko sprejemljive soli.A compound selected from the group consisting of (3S) -3 - [({[1- (2-chlorobenzyl) -4-hydroxy-5-methyl-2-oxo-1,2-dihydropyridin- -yl] amino} carbonyl) amino] -3- (4-methylphenyl) propanoic acid; (3S) -3 - [({[1- (2-chlorobenzyl) -4-hydroxy-2-oxo-2,5,6,7-tetrahydro-1H-cyclopenta [b] pyridin-3-yl] amino} carbonyl) amino] -3- (4-methylphenyl) propanoic acid; and (3S) -3 - [({[1- (2-chlorobenzyl) -4-hydroxy-5-methyl-2-oxo- 1,2-dihydropyridin-3- yl] amino} carbonyl) amino] -3 - (3-diethylamino) phenyl] propanoic acid; and pharmaceutically acceptable salts thereof. 2.2. (3 S)-3-[({[ 1 -(2-klorobenzil)-4-hidroksi-5-metil-2-okso-1,2-dihidropiridin-3-il]amino}karbonil)amino]-3-(4-metilfenil)propanojska kislina in njene farmacevtsko sprejemljive soli. 3. (3S)-3-[({[l-(2-klorobenzil)-4-hidroksi-2-okso-2,5,6,7-tetrahidro-lH-ciklopenta[b]piridin-3-il]amino}karbonil)amino]-3-(4-metilfenil)propanojska kislina in njene farmacevtsko sprejemljive soli.(3S) -3 - [({[1- (2-chlorobenzyl) -4-hydroxy-5-methyl-2-oxo- 1,2- dihydropyridin-3- yl] amino} carbonyl) amino] (4-methylphenyl) propanoic acid and its pharmaceutically acceptable salts. 3 (3S) -3 - [({[1- (2-chlorobenzyl) -4-hydroxy-2-oxo-2,5,6,7-tetrahydro-1H-cyclopenta [b] pyridin-3-yl] amino} carbonyl) amino] -3- (4-methylphenyl) propanoic acid and its pharmaceutically acceptable salts. 4. (3S)-3-[( {[ 1 -(2-klorobenzil)-4-hidroksi-5-metil-2-okso-1,2-dihidropiridin-3-il]amino}karbonil)amino]-3-(3-dietilamino)fenil]propanojska kislina in njene farmacevtsko sprejemljive soli.4 - (3S) -3 - [({[1- (2-chlorobenzyl) -4-hydroxy-5-methyl-2-oxo- 1,2- dihydropyridin-3- yl] amino} carbonyl) amino] -3 - (3-diethylamino) phenyl] propanoic acid and its pharmaceutically acceptable salts. 5. Farmacevtski sestavek, označen s tem, da obsega spojino po katerem koli od zahtevkov 1 do 4 in farmacevtsko sprejemljiv nosilec. 2 % · • ·A pharmaceutical composition comprising a compound according to any one of claims 1 to 4 and a pharmaceutically acceptable carrier. 2% 6. Spojina po katerem koli od zahtevkov 1 do 4 za uporabo pri zdravljenju bolezni, izbrane iz skupine, v kateri so astma, ateroskleroza, revmatoidni artritis, alergija, multipla skleroza, lupus, vnetna črevesna bolezen, zavrnitev presadka, kontaktna hipersenzibilnost, diabetes tipa I, levkemija in možganski rak.A compound according to any one of claims 1 to 4 for use in the treatment of a disease selected from the group consisting of asthma, atherosclerosis, rheumatoid arthritis, allergy, multiple sclerosis, lupus, inflammatory bowel disease, graft rejection, contact hypersensitivity, type of diabetes I, leukemia and brain cancer.
SI200100288A 2001-10-09 2001-11-05 Carboxylic acid derivatives that inhibit the binding of integrins to,their receptors SI21096B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US09/973,142 US6972296B2 (en) 1999-05-07 2001-10-09 Carboxylic acid derivatives that inhibit the binding of integrins to their receptors

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SI21096A1 SI21096A1 (en) 2003-06-30
SI21096B true SI21096B (en) 2012-05-31

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CN (2) CN101475526B (en)
CA (1) CA2366800C (en)
HK (1) HK1135376A1 (en)
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CA2513493A1 (en) * 2002-11-08 2004-05-27 Schering Corporation Combination products with carboxylic acid derivatives that inhibit the binding of integrins to their receptors and other therapeutic compounds
WO2008109991A1 (en) * 2007-03-09 2008-09-18 University Health Network Inhibitors of carnitine palmitoyltransferase and treating cancer
US8680282B2 (en) 2007-08-01 2014-03-25 University Health Network Cyclic inhibitors of carnitine palmitoyltransferase and treating cancer
MX2011011326A (en) * 2009-04-27 2012-02-13 Elan Pharm Inc Pyridinone antagonists of alpha-4 integrins.
US10875875B2 (en) * 2017-04-26 2020-12-29 Aviara Pharmaceuticals, Inc. Propionic acid derivatives and methods of use thereof
CN118591535A (en) * 2021-12-27 2024-09-03 西藏海思科制药有限公司 Propionic acid derivative and application thereof in medicine
WO2024051819A1 (en) * 2022-09-09 2024-03-14 西藏海思科制药有限公司 Propionic acid derivative and use thereof in medicine

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DE2614189A1 (en) * 1976-04-02 1977-10-20 Hoechst Ag Analgesic, antiinflammatory and antipyretic thiazolyl-urea derivs. - prepd. by reacting an isocyanato-carboxylic acid cpd. with an amino-or hydrazino-thiazole
AU636853B2 (en) * 1988-08-23 1993-05-13 Nutrasweet Company, The Substituted aryl ureas as high potency sweeteners
FR2659653B1 (en) * 1990-03-13 1992-05-22 Rhone Poulenc Sante DERIVATIVES OF UREA, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING THEM.
HUT68769A (en) * 1991-05-07 1995-07-28 Merck & Co Inc FIBRINOGéN RECEPTOR ANTAGONIST COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM AS EFFECTIVE SUBSTANCE
EP0691953B1 (en) * 1993-03-31 2000-08-02 G.D. Searle & Co. 1-amidinophenyl-pyrrolidones/ piperidinones as platelet aggregation inhibitors
US5610296A (en) * 1994-12-05 1997-03-11 G. D. Searle & Co. Process for the preparation of amidino phenyl pyrrolidine beta-alanine urea analogs
AU3563799A (en) * 1998-04-16 1999-11-01 Texas Biotechnology Corporation Compounds that inhibit the binding of integrins to their receptors
DK1176956T3 (en) * 1999-05-07 2008-05-26 Encysive Pharmaceuticals Inc Carboxylic acid derivatives which inhibit the binding of integrins to their receptors

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SG161741A1 (en) 2010-06-29
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CN100491353C (en) 2009-05-27
CN101475526B (en) 2011-05-25
HK1135376A1 (en) 2010-06-04
SI21096A1 (en) 2003-06-30
PL223151B1 (en) 2016-10-31
SG107574A1 (en) 2004-12-29
CN1412181A (en) 2003-04-23
CA2366800A1 (en) 2003-04-10
CA2366800C (en) 2010-08-10
CN101475526A (en) 2009-07-08
PL356532A1 (en) 2003-04-22

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