DE69706407D1 - META-SUBSTITUIERTE PHENYLENDERIVATE UND IHRE VERWENDUNG ALS ALPHAvBETA3 INTERGRIN-ANTAGONISTEN ODER INHIBITOREN - Google Patents

META-SUBSTITUIERTE PHENYLENDERIVATE UND IHRE VERWENDUNG ALS ALPHAvBETA3 INTERGRIN-ANTAGONISTEN ODER INHIBITOREN

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Publication number
DE69706407D1
DE69706407D1 DE69706407T DE69706407T DE69706407D1 DE 69706407 D1 DE69706407 D1 DE 69706407D1 DE 69706407 T DE69706407 T DE 69706407T DE 69706407 T DE69706407 T DE 69706407T DE 69706407 D1 DE69706407 D1 DE 69706407D1
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Prior art keywords
intergrin
antagonists
meta
inhibitors
substituted phenylene
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Expired - Fee Related
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DE69706407T
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English (en)
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DE69706407T2 (de
Inventor
Nizal Chandrakumar
B Chen
Helen Chen
Michael Clare
F Gasiecki
A Haack
W Malecha
G Ruminski
A Russell
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GD Searle LLC
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GD Searle LLC
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
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    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
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    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/16—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of rings other than six-membered aromatic rings
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    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
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    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
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    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
    • C07C311/46—Y being a hydrogen or a carbon atom
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    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
    • C07C311/47—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
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    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/42—Y being a hetero atom
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    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
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    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
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    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
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    • C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
    • C07C49/796—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring polycyclic
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
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    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
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    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
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    • C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
    • C07D239/12—Nitrogen atoms not forming part of a nitro radical
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    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
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    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
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    • 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

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
DE69706407T 1996-03-29 1997-03-26 META-SUBSTITUIERTE PHENYLENDERIVATE UND IHRE VERWENDUNG ALS ALPHAvBETA3 INTERGRIN-ANTAGONISTEN ODER INHIBITOREN Expired - Fee Related DE69706407T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US1446496P 1996-03-29 1996-03-29
PCT/US1997/004461 WO1997036862A1 (en) 1996-03-29 1997-03-26 META-SUBSTITUTED PHENYLENE DERIVATIVES AND THEIR USE AS ALPHAvBETA3 INTEGRIN ANTAGONISTS OR INHIBITORS

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Families Citing this family (99)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU702487B2 (en) * 1995-08-30 1999-02-25 G.D. Searle & Co. Meta-guanidine, urea, thiourea or azacyclic amino benzoic acid derivatives as integrin antagonists
AU2420897A (en) * 1996-03-29 1997-10-22 G.D. Searle & Co. Meta-substituted phenylene sulphonamide derivatives
US6245809B1 (en) 1996-12-09 2001-06-12 Cor Therapeutics Inc. Integrin antagonists
WO1998042329A1 (fr) * 1997-03-21 1998-10-01 Mitsubishi Chemical Corporation Preventifs et/ou remedes destines a des affections provoquees par une neovascularisation anormale
US6455550B1 (en) 1997-08-22 2002-09-24 Hoffmann-La Roche Inc. N-alkanoylphenylalanine derivatives
ES2214728T3 (es) * 1997-08-22 2004-09-16 F. Hoffmann-La Roche Ag Derivados de n-aroilfenilalanina.
US6229011B1 (en) 1997-08-22 2001-05-08 Hoffman-La Roche Inc. N-aroylphenylalanine derivative VCAM-1 inhibitors
SK5462000A3 (en) 1997-10-31 2001-02-12 Aventis Pharma Ltd Substituted anilides
WO1999033789A1 (en) * 1997-12-23 1999-07-08 Aventis Pharma Limited SUBSTITUTED β-ALANINES
US6329372B1 (en) 1998-01-27 2001-12-11 Celltech Therapeutics Limited Phenylalanine derivatives
CA2319465C (en) * 1998-01-29 2013-03-19 Viropharma Incorporated Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
US6495580B1 (en) 1998-01-29 2002-12-17 Viropharma Incorporated Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
EP1056714B1 (de) * 1998-02-26 2004-08-11 Celltech Therapeutics Limited Phenylalaninderivate als inhibitoren von alpha4 integrinen
GB9805655D0 (en) 1998-03-16 1998-05-13 Celltech Therapeutics Ltd Chemical compounds
US6521626B1 (en) 1998-03-24 2003-02-18 Celltech R&D Limited Thiocarboxamide derivatives
CN1140511C (zh) 1998-04-09 2004-03-03 明治制果株式会社 作为整合素αvβ3拮抗剂的氨基哌啶衍生物
AU3716499A (en) * 1998-04-21 1999-11-08 Aventis Pharma Limited Substituted diamines and their use as cell adhesion inhibitors
GB9811159D0 (en) * 1998-05-22 1998-07-22 Celltech Therapeutics Ltd Chemical compounds
GB9811969D0 (en) 1998-06-03 1998-07-29 Celltech Therapeutics Ltd Chemical compounds
GB9814414D0 (en) 1998-07-03 1998-09-02 Celltech Therapeutics Ltd Chemical compounds
US6352977B1 (en) 1998-07-13 2002-03-05 Aventis Pharma Limited Substituted β-alanines
EP1133484A2 (de) * 1998-07-23 2001-09-19 AstraZeneca AB Heterocyclische derivate und ihre verwendung als integrininhibitore
GB9916374D0 (en) * 1998-07-23 1999-09-15 Zeneca Ltd Chemical compounds
GB9821061D0 (en) 1998-09-28 1998-11-18 Celltech Therapeutics Ltd Chemical compounds
GB9821222D0 (en) 1998-09-30 1998-11-25 Celltech Therapeutics Ltd Chemical compounds
US6420403B1 (en) * 1998-10-29 2002-07-16 Edwin J. Iwanowicz Inhibitors of IMPDH enzyme
GB9825652D0 (en) * 1998-11-23 1999-01-13 Celltech Therapeutics Ltd Chemical compounds
GB9826174D0 (en) 1998-11-30 1999-01-20 Celltech Therapeutics Ltd Chemical compounds
US6677360B2 (en) 1998-12-16 2004-01-13 Bayer Aktiengesellschaft Biphenyl and biphenyl-analogous compounds as integrin antagonists
US6420396B1 (en) 1998-12-16 2002-07-16 Beiersdorf Ag Biphenyl and biphenyl-analogous compounds as integrin antagonists
AP2000001924A0 (en) 1998-12-23 2000-09-30 Aventis Pharma Ltd Dihydro-benzo(1,4)oxazines and tetrahydroquinoxalines.
PL349216A1 (en) 1998-12-23 2002-07-01 Searle & Co Method of using a cyclooxygenase-2 inhibitor and a matrix metalloproteinase inhibitor as a combination therapy in the treatment of neoplasia
US6291503B1 (en) 1999-01-15 2001-09-18 Bayer Aktiengesellschaft β-phenylalanine derivatives as integrin antagonists
DE60027700T2 (de) * 1999-02-16 2007-05-03 Aventis Pharma Ltd., West Malling Bicyclische verbindungen und ihre verwendung als integrinrezeptorliganden
PL349463A1 (en) 1999-02-18 2002-07-29 Hoffmann La Roche Phenylalaninol derivatives
CZ20012980A3 (cs) 1999-02-18 2002-04-17 F. Hoffmann-La Roche Ag Thioamidové deriváty
EP1177181B1 (de) 1999-05-05 2009-01-28 Aventis Pharma Limited Substituierte bizyclische verbindungen
US6518283B1 (en) * 1999-05-28 2003-02-11 Celltech R&D Limited Squaric acid derivatives
EP1198231A1 (de) 1999-07-21 2002-04-24 American Home Products Corporation Bicyklischer antagonist selektiv für (alpha)v (beta)3 integrin
AU6316900A (en) 1999-08-05 2001-03-05 Meiji Seika Kaisha Ltd. Omega-amino-alpha-hydroxycarboxylic acid derivatives having integrin alphavbeta3antagonism
DE19937394A1 (de) * 1999-08-07 2001-02-08 Merck Patent Gmbh Fluorenderivate
DE19939980A1 (de) * 1999-08-24 2001-03-01 Merck Patent Gmbh Inhibitoren des Integrins alphavbeta¶3¶
US6534513B1 (en) 1999-09-29 2003-03-18 Celltech R&D Limited Phenylalkanoic acid derivatives
TWI262185B (en) * 1999-10-01 2006-09-21 Eisai Co Ltd Carboxylic acid derivatives having anti-hyperglycemia and anti-hyperlipemia action, and pharmaceutical composition containing the derivatives
US6849639B2 (en) 1999-12-14 2005-02-01 Amgen Inc. Integrin inhibitors and their methods of use
GB9929988D0 (en) * 1999-12-17 2000-02-09 Celltech Therapeutics Ltd Chemical compounds
WO2001046110A2 (en) * 1999-12-23 2001-06-28 The University Of Georgia Research Foundation, Inc. Chalcone and its analogs as agents for the inhibition of angiogenesis and related disease states
US6455539B2 (en) 1999-12-23 2002-09-24 Celltech R&D Limited Squaric acid derivates
AU781506B2 (en) * 2000-02-03 2005-05-26 Eisai R&D Management Co., Ltd. Integrin expression inhibitors
ATE375330T1 (de) 2000-04-17 2007-10-15 Ucb Pharma Sa Enamin-derivate als zell-adhäsionsmoleküle
GB0011817D0 (en) 2000-05-16 2000-07-05 Pharmacia & Upjohn Spa Antagonists of integrin receptors
US7049342B2 (en) 2000-05-29 2006-05-23 Kyorin Pharmaceutical Co., Ltd. Substituted phenylpropionic acid derivatives
ES2312432T3 (es) * 2000-05-29 2009-03-01 Kyorin Pharmaceutical Co., Ltd. Derivados del acido fenilpropionico sustituidos.
US6545013B2 (en) 2000-05-30 2003-04-08 Celltech R&D Limited 2,7-naphthyridine derivatives
US6403608B1 (en) 2000-05-30 2002-06-11 Celltech R&D, Ltd. 3-Substituted isoquinolin-1-yl derivatives
UY26780A1 (es) 2000-06-15 2002-01-31 Pharmacia Corp Cicloalquil avb3 antagonistas
WO2001096334A2 (en) * 2000-06-15 2001-12-20 Pharmacia Corporation Heteroarylalkanoic acids as integrin receptor antagonists
WO2002004426A1 (en) 2000-07-07 2002-01-17 Celltech R & D Limited Squaric acid derivatives containing a bicyclic heteroaromatic ring as integrin antagonists
EP1305291A1 (de) 2000-08-02 2003-05-02 Celltech R&D Limited 3-substituierte isochinolin-1-yl-derivate
CA2419580A1 (en) * 2000-08-18 2002-02-28 Genentech, Inc. Integrin receptor inhibitors
EP1332127A2 (de) * 2000-10-30 2003-08-06 Warner-Lambert Company LLC Amidin-harnstoff als serotoninrezeptorliganden und deren zusammentsetzungen, deren pharmazeutische anwendung und methoden zu deren herstellung
FR2817749A1 (fr) * 2000-12-13 2002-06-14 Aventis Pharma Sa Nouvelle utilisation des composes de la classe des chalcones
DE10064823A1 (de) * 2000-12-22 2002-06-27 Knoll Ag Integrinrezeptorliganden
ITTO20010110A1 (it) 2001-02-08 2002-08-08 Rotta Research Lab Nuovi derivati benzamidinici dotati di attivita' anti-infiammatoria ed immunosoppressiva.
US20040043988A1 (en) * 2001-06-15 2004-03-04 Khanna Ish Kurmar Cycloalkyl alkanoic acids as intergrin receptor antagonists
WO2003042190A1 (en) * 2001-11-12 2003-05-22 Pfizer Products Inc. N-alkyl-adamantyl derivatives as p2x7-receptor antagonists
PA8557501A1 (es) 2001-11-12 2003-06-30 Pfizer Prod Inc Benzamida, heteroarilamida y amidas inversas
JP2005525368A (ja) * 2002-03-04 2005-08-25 メディミューン，インコーポレーテッド インテグリンαｖβ３アンタゴニストをＨＭＧ−ＣｏＡ還元酵素阻害剤またはビスフォスフォネートと併用投与する障害の予防または治療方法
CA2478239A1 (en) * 2002-03-04 2003-09-18 Medimmune, Inc. The prevention or treatment of cancer using integrin alphavbeta3 antagonists in combination with other agents
CA2495266A1 (en) * 2002-08-09 2004-02-19 Viropharma Incorporated Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
WO2004014317A2 (en) * 2002-08-09 2004-02-19 Viropharma Incorporated Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
JP2006518333A (ja) * 2002-12-20 2006-08-10 ファルマシア・コーポレーション インテグリン受容体アンタゴニストとしてのヘテロアリールアルカン酸
BR0316876A (pt) * 2002-12-20 2005-10-25 Pharmacia Corp Compostos de tiazol e composição farmacêutica compreendendo o mesmo
WO2004058761A1 (en) * 2002-12-20 2004-07-15 Pharmacia Corporation Pyrazole compounds as integrin receptor antagonists derivatives
US7071223B1 (en) 2002-12-31 2006-07-04 Pfizer, Inc. Benzamide inhibitors of the P2X7 receptor
PA8591801A1 (es) * 2002-12-31 2004-07-26 Pfizer Prod Inc Inhibidores benzamidicos del receptor p2x7.
CA2514653A1 (en) * 2003-01-30 2004-08-12 Medimmune, Inc. Uses of integrin alphavbeta3 antagonists
DE602004005033T2 (de) * 2003-05-12 2007-08-09 Pfizer Products Inc., Groton Benzamidinhibitoren des p2x7-rezeptors
GB0401334D0 (en) * 2004-01-21 2004-02-25 Novartis Ag Organic compounds
UA87854C2 (en) 2004-06-07 2009-08-25 Мерк Энд Ко., Инк. N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators
EP1768965A1 (de) * 2004-06-29 2007-04-04 Pfizer Products Incorporated Verfahren zur herstellung von 5-[4-(2-hydroxyethyl)-3,5-dioxo-4,5-dihydro-3h-[1,2,4]-triazin-2-yl]benzamidderivaten mit p2x7-hemmender wirkung durch umsetzung des in der 4-stellung des triazins unsubstituierten derivats mit einem oxiran in gegenwart einer lewissäure
EP1763353A1 (de) * 2004-06-29 2007-03-21 Warner-Lambert Company LLC KOMBINATIONSTHERAPIEN MIT BENZAMID-HEMMERN DES P2X<SB>7</SB> REZEPTORS
WO2006003500A1 (en) * 2004-06-29 2006-01-12 Pfizer Products Inc. Method for preparing 5-`4-(2-hydroxy-propyl)-3,5-dioxo-4,5-dihydro-3h`1,2,4!triazin-2-yl!-benzamide derivatives by deprotecting the hydroxyl-protected precursers
EP1802618A1 (de) * 2004-10-14 2007-07-04 Pharmacia Corporation Biphenylverbindungen als integrinantagonisten
FR2896245B1 (fr) * 2006-01-17 2010-09-17 Univ Claude Bernard Lyon Nouveaux derives de chalcone, a activite antimitotique
IE20070935A1 (en) * 2007-12-21 2009-06-24 Trinity College Dublin Guanidine based compounds and their use in the treatment of mental and neurological disorders.
PT2222636E (pt) 2007-12-21 2013-07-16 Ligand Pharm Inc Moduladores seletivos de recetores de andrógeno (sarms) e suas utilizações
US8716226B2 (en) 2012-07-18 2014-05-06 Saint Louis University 3,5 phenyl-substituted beta amino acid derivatives as integrin antagonists
WO2014015054A1 (en) 2012-07-18 2014-01-23 Saint Louis University Beta amino acid derivatives as integrin antagonists
EP3030244B1 (de) 2013-08-07 2021-04-21 Arrowhead Pharmaceuticals, Inc. Polykonjugate zur in-vivo-verabreichung von rnai-auslösern gegen tumorzellen
EP3148587B1 (de) 2014-05-30 2021-02-24 Pfizer Inc Carbonitrilderivate als selektive androgenrezeptormodulatoren
AU2016381336A1 (en) 2015-12-30 2018-06-28 Saint Louis University Meta-azacyclic amino benzoic acid derivatives as pan integrin antagonists
CA3012133A1 (en) * 2016-02-09 2017-08-17 Inventisbio Inc. Inhibitor of indoleamine-2,3-dioxygenase (ido)
EP3589631B1 (de) 2017-03-01 2021-07-21 3M Innovative Properties Company Imidazo[4,5-c]ring-verbindungen enthaltend guanidin-substituierten benzamidgruppen
CN107652210B (zh) * 2017-09-30 2021-01-01 瑞阳（上海）新药研发有限公司 一种胍类化合物或其药学上可接受的盐、其制备方法和应用
WO2023275715A1 (en) 2021-06-30 2023-01-05 Pfizer Inc. Metabolites of selective androgen receptor modulators
CN113717133B (zh) * 2021-09-14 2023-11-17 浙江大学 3-酰胺基-n-芳基苯甲酰胺类化合物及应用
CN114394946A (zh) * 2022-02-21 2022-04-26 艾美科健（中国）生物医药有限公司 一种氟雷拉纳的合成方法
CN115232027B (zh) * 2022-08-03 2023-10-10 中国农业大学 一种n-叔丁基-n’-(2,6-二异丙基-4-苯氧基苯基)甲脒的制备方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5084466A (en) * 1989-01-31 1992-01-28 Hoffmann-La Roche Inc. Novel carboxamide pyridine compounds which have useful pharmaceutical utility
NZ239846A (en) * 1990-09-27 1994-11-25 Merck & Co Inc Sulphonamide derivatives and pharmaceutical compositions thereof
IL99537A (en) * 1990-09-27 1995-11-27 Merck & Co Inc Fibrinogen receptor antagonists and pharmaceutical preparations containing them
US5523302A (en) * 1993-11-24 1996-06-04 The Du Pont Merck Pharmaceutical Company Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists
PT656348E (pt) * 1993-12-03 2000-10-31 Hoffmann La Roche Derivados do acido acetico como medicamentos
CA2190870A1 (en) * 1994-05-27 1995-12-07 George D. Hartman Compounds for inhibiting osteoclast-mediated bone resorption
WO1996000574A1 (en) * 1994-06-29 1996-01-11 Smithkline Beecham Corporation Vitronectin receptor antagonists

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ATE204857T1 (de) 2001-09-15
CA2250464A1 (en) 1997-10-09
PT889877E (pt) 2002-02-28
WO1997036862A1 (en) 1997-10-09
ES2162676T3 (es) 2002-01-01
DE69706407T2 (de) 2002-05-29
AU2337097A (en) 1997-10-22
EP0889877A1 (de) 1999-01-13
EP0889877B1 (de) 2001-08-29
DK0889877T3 (da) 2001-10-01
US5773646A (en) 1998-06-30
JP2000506538A (ja) 2000-05-30

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