CA2093770A1 - Aspartic acid derivatives, their preparation and use - Google Patents

Aspartic acid derivatives, their preparation and use

Info

Publication number
CA2093770A1
CA2093770A1 CA002093770A CA2093770A CA2093770A1 CA 2093770 A1 CA2093770 A1 CA 2093770A1 CA 002093770 A CA002093770 A CA 002093770A CA 2093770 A CA2093770 A CA 2093770A CA 2093770 A1 CA2093770 A1 CA 2093770A1
Authority
CA
Canada
Prior art keywords
aspartic acid
acid derivatives
preparation
denotes
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002093770A
Other languages
French (fr)
Other versions
CA2093770C (en
Inventor
Otmar Klingler
Gerhard Zoller
Melitta Just
Bernd Jablonka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis Deutschland GmbH
Original Assignee
Cassella AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cassella AG filed Critical Cassella AG
Publication of CA2093770A1 publication Critical patent/CA2093770A1/en
Application granted granted Critical
Publication of CA2093770C publication Critical patent/CA2093770C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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
    • C07C279/04—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 acyclic carbon atoms of a carbon skeleton
    • C07C279/08—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 acyclic carbon atoms of a carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Abstract

Aspartic acid derivatives of the formula (see formula I) in which X denotes, for example, (see formula II) and R denotes, for example, cyclohexylamino, have useful pharmacological properties. In particular, they have the ability to inhibit the binding of fibrinogen, fibronectin and von Willebrand factor to integrin receptors. They also inhibit platelet aggregation, metastasis of carcinoma cells and osteoclast formation on bone surfaces and are useful in prophylaxis and therapy of, for example, arterial vascular diseases and in the treatment of tumors.
CA002093770A 1992-04-13 1993-04-08 Aspartic acid derivatives, their preparation and use Expired - Lifetime CA2093770C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4212304.6 1992-04-13
DE4212304A DE4212304A1 (en) 1992-04-13 1992-04-13 Aspartic acid derivatives, their preparation and use

Publications (2)

Publication Number Publication Date
CA2093770A1 true CA2093770A1 (en) 1993-10-14
CA2093770C CA2093770C (en) 2004-09-07

Family

ID=6456690

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002093770A Expired - Lifetime CA2093770C (en) 1992-04-13 1993-04-08 Aspartic acid derivatives, their preparation and use

Country Status (15)

Country Link
US (1) US5399570A (en)
EP (2) EP0565896A2 (en)
JP (1) JP3504287B2 (en)
KR (1) KR930021605A (en)
AT (1) ATE307825T1 (en)
AU (1) AU659299B2 (en)
CA (1) CA2093770C (en)
CZ (1) CZ290280B6 (en)
DE (2) DE4212304A1 (en)
ES (1) ES2250980T3 (en)
HU (1) HU218206B (en)
IL (1) IL105355A (en)
SK (1) SK282125B6 (en)
TW (1) TW267158B (en)
ZA (1) ZA932535B (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5446056A (en) * 1993-11-24 1995-08-29 The Du Pont Merck Pharmaceutical Company Isoxazoline compounds useful as fibrinogen receptor antagonists
US5494922A (en) * 1993-06-28 1996-02-27 Zeneca Limited Allophanic acid derivatives
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
US5556977A (en) * 1993-03-29 1996-09-17 Zeneca Limited Heterocyclic derivatives
US5563141A (en) * 1993-03-29 1996-10-08 Zeneca Limited Heterocyclic compounds
US5563158A (en) * 1993-12-28 1996-10-08 The Dupont Merck Pharmaceutical Company Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists
US5576334A (en) * 1993-06-28 1996-11-19 Zeneca Limited Acylurea derivatives
US5612373A (en) * 1993-06-28 1997-03-18 Zeneca Limited Certain diacyl hydrazine derivatives
US5652242A (en) * 1993-03-29 1997-07-29 Zeneca Limited Heterocyclic derivatives
US5750754A (en) * 1993-03-29 1998-05-12 Zeneca Limited Heterocyclic compounds
US5753659A (en) * 1993-03-29 1998-05-19 Zeneca Limited Heterocyclic compouds
US5811441A (en) * 1995-05-24 1998-09-22 The Dupont Merck Pharmaceutical Company Isoxazoline fibrinogen receptor antagonists
US5849736A (en) * 1993-11-24 1998-12-15 The Dupont Merck Pharmaceutical Company Isoxazoline and isoxazole fibrinogen receptor antagonists

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5169930A (en) * 1990-01-05 1992-12-08 La Jolla Cancer Research Foundation Fibronectin receptor
DK0513675T3 (en) * 1991-05-13 1996-09-30 Fujisawa Pharmaceutical Co New peptide compound and method of preparation thereof
TW257757B (en) * 1993-03-03 1995-09-21 Boehringer Mannheim Gmbh
US6274705B1 (en) * 1996-05-02 2001-08-14 Aventis Pharmaceuticals Products Inc. Antithrombotic azacycloalkylalkanoyl peptides and pseudopeptides
US7001921B1 (en) 1995-01-23 2006-02-21 Biogen Idec Ma Inc. Cell adhesion inhibitors
US6306840B1 (en) 1995-01-23 2001-10-23 Biogen, Inc. Cell adhesion inhibitors
US6248713B1 (en) 1995-07-11 2001-06-19 Biogen, Inc. Cell adhesion inhibitors
AU713676B2 (en) * 1996-01-16 1999-12-09 Merck & Co., Inc. Integrin receptor antagonists
US6239108B1 (en) 1996-07-11 2001-05-29 Biogen, Inc. Cell adhesion inhibitors
DE69737769T2 (en) 1996-07-25 2008-05-15 Biogen Idec Ma Inc., Cambridge MOLECULE MODEL FOR VLA-4 INHIBITORS
US6686350B1 (en) 1996-07-25 2004-02-03 Biogen, Inc. Cell adhesion inhibitors
US5759152A (en) * 1996-10-02 1998-06-02 Mayo Foundation For Medical Education And Research Phase-aligned NMR surface coil image reconstruction
WO1999055688A1 (en) * 1998-04-27 1999-11-04 Warner-Lambert Company Substituted diarylalkyl amides as calcium channel antagonists
EA002988B1 (en) 1998-05-28 2002-12-26 Байоджен, Инк. (R)-N-[[4-[[(2-METHYLPHENYLAMINO)CARBONYL]AMINO]PHENYL]ACETYL]-L-PROPYL-3-METHYL)-BETA-ALANINE AND ITS USE AS A CELL ADHESION INHIBITOR MEDIATED BY INTEGRIN alpha4beta1 INHIBITORS
SK287075B6 (en) * 1999-08-13 2009-11-05 Biogen Idec Ma Inc. Cell adhesion inhibitors and pharmaceutical compositions comprising them
US6875743B1 (en) 2000-11-28 2005-04-05 Biogen, Inc. Cell adhesion inhibitors
DE10204789A1 (en) * 2002-02-06 2003-08-14 Merck Patent Gmbh Inhibitors of the integrin alpha¶v¶beta6
US20050192348A1 (en) * 2003-09-25 2005-09-01 David Bar-Or Methods and products which utilize N-acyl-L-aspartic acid
BRPI0509150B8 (en) * 2004-03-24 2021-05-25 Jerini Ag compounds for the inhibition of angiogenesis and the use of these
US7196112B2 (en) 2004-07-16 2007-03-27 Biogen Idec Ma Inc. Cell adhesion inhibitors
EP1853246A1 (en) * 2005-02-17 2007-11-14 Instituto del Metabolismo Celular, S.L. L-aspartic acid for the treatment of problems in connection with the fat or glucose metabolism

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4879313A (en) * 1988-07-20 1989-11-07 Mosanto Company Novel platelet-aggregation inhibitors
US5039805A (en) * 1988-12-08 1991-08-13 Hoffmann-La Roche Inc. Novel benzoic and phenylacetic acid derivatives
US5084466A (en) * 1989-01-31 1992-01-28 Hoffmann-La Roche Inc. Novel carboxamide pyridine compounds which have useful pharmaceutical utility
US5318899A (en) * 1989-06-16 1994-06-07 Cor Therapeutics, Inc. Platelet aggregation inhibitors
US4952562A (en) * 1989-09-29 1990-08-28 Rorer Pharmaceutical Corporation Anti-thrombotic peptides and pseudopeptides
JPH05500954A (en) * 1989-09-29 1993-02-25 ローヌ―プーラン　ローラー　インターナショナル（ホウルディングス）　インコーポレイテッド Antithrombotic peptides and pseudopeptides
US5051405A (en) * 1989-10-10 1991-09-24 Rhone-Poulenc Rorer Pharmaceuticals Inc. Anti-thrombotic peptides and pseudopeptides
US5086069A (en) * 1990-02-05 1992-02-04 Rorer Pharmaceutical Corporation Anti-thrombotic peptide and pseudopeptide derivatives
US5264420A (en) * 1990-09-27 1993-11-23 Merck & Co., Inc. Fibrinogen receptor antagonists
US5481021A (en) * 1991-03-06 1996-01-02 G. D. Searle & Co. Phenyl amidines derivatives useful as platelet aggregation inhibitors
US5227490A (en) * 1992-02-21 1993-07-13 Merck & Co., Inc. Fibrinogen receptor antagonists

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5652242A (en) * 1993-03-29 1997-07-29 Zeneca Limited Heterocyclic derivatives
US5728701A (en) * 1993-03-29 1998-03-17 Zeneca Limited Heterocyclic derivatives
US5556977A (en) * 1993-03-29 1996-09-17 Zeneca Limited Heterocyclic derivatives
US5563141A (en) * 1993-03-29 1996-10-08 Zeneca Limited Heterocyclic compounds
US5753659A (en) * 1993-03-29 1998-05-19 Zeneca Limited Heterocyclic compouds
US5750754A (en) * 1993-03-29 1998-05-12 Zeneca Limited Heterocyclic compounds
US5981531A (en) * 1993-06-28 1999-11-09 Zeneca Limited Acid derivatives
US5760057A (en) * 1993-06-28 1998-06-02 Zeneca Limited Certain (piperidin-4-yl-alkanoyl)carbazoyl!-carboxy-phenoxy derivatives
US5576334A (en) * 1993-06-28 1996-11-19 Zeneca Limited Acylurea derivatives
US5612373A (en) * 1993-06-28 1997-03-18 Zeneca Limited Certain diacyl hydrazine derivatives
US5494922A (en) * 1993-06-28 1996-02-27 Zeneca Limited Allophanic acid derivatives
US6114328A (en) * 1993-11-24 2000-09-05 Dupont Pharmaceuticals Company Isoxazoline and isoxazole fibrogen receptor antagonists
US5739163A (en) * 1993-11-24 1998-04-14 The Dupont Merck Pharmaceutical Company Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists
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
US5849736A (en) * 1993-11-24 1998-12-15 The Dupont Merck Pharmaceutical Company Isoxazoline and isoxazole fibrinogen receptor antagonists
US5446056A (en) * 1993-11-24 1995-08-29 The Du Pont Merck Pharmaceutical Company Isoxazoline compounds useful as fibrinogen receptor antagonists
US5563158A (en) * 1993-12-28 1996-10-08 The Dupont Merck Pharmaceutical Company Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists
US5691329A (en) * 1993-12-28 1997-11-25 The Dupont Merck Pharmaceutical Company Compounds containing basic and acidic termini useful as fibrinogen receptor antagonists
US5811441A (en) * 1995-05-24 1998-09-22 The Dupont Merck Pharmaceutical Company Isoxazoline fibrinogen receptor antagonists

Also Published As

Publication number Publication date
IL105355A0 (en) 1993-08-18
ZA932535B (en) 1993-11-04
JP3504287B2 (en) 2004-03-08
ES2250980T3 (en) 2006-04-16
EP0565896A2 (en) 1993-10-20
CA2093770C (en) 2004-09-07
EP0784058A1 (en) 1997-07-16
DE4212304A1 (en) 1993-10-14
EP0565896A3 (en) 1994-01-12
CZ49493A3 (en) 1994-02-16
JPH07109256A (en) 1995-04-25
SK33493A3 (en) 1994-02-02
KR930021605A (en) 1993-11-22
TW267158B (en) 1996-01-01
AU3683693A (en) 1993-10-14
HU9301071D0 (en) 1993-06-28
AU659299B2 (en) 1995-05-11
DE59310379D1 (en) 2005-12-01
EP0784058B8 (en) 2005-12-28
HUT64016A (en) 1993-11-29
US5399570A (en) 1995-03-21
SK282125B6 (en) 2001-11-06
IL105355A (en) 1998-03-10
ATE307825T1 (en) 2005-11-15
EP0784058B1 (en) 2005-10-26
CZ290280B6 (en) 2002-07-17
HU218206B (en) 2000-06-28

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Legal Events

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EEER Examination request
MKLA Lapsed

Effective date: 20130408

MKEC Expiry (correction)

Effective date: 20131009