CA2094773A1 - 2,4-dioxoimidazolidine derivatives - Google Patents

2,4-dioxoimidazolidine derivatives

Info

Publication number
CA2094773A1
CA2094773A1 CA002094773A CA2094773A CA2094773A1 CA 2094773 A1 CA2094773 A1 CA 2094773A1 CA 002094773 A CA002094773 A CA 002094773A CA 2094773 A CA2094773 A CA 2094773A CA 2094773 A1 CA2094773 A1 CA 2094773A1
Authority
CA
Canada
Prior art keywords
dioxoimidazolidine
derivatives
alkyl
hydrogen
integer
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
CA002094773A
Other languages
French (fr)
Other versions
CA2094773C (en
Inventor
Gerhard Zoller
Wolfgang Konig
Jochen Knolle
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 CA2094773A1 publication Critical patent/CA2094773A1/en
Application granted granted Critical
Publication of CA2094773C publication Critical patent/CA2094773C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C07K5/10—Tetrapeptides
    • C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
    • 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
    • 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Abstract

The present invention relates to 2,4-dioxoimidazolidine derivatives of the general formula I
(see figure I) wherein R1 is, fox example,-(CH2)n-NH-X, where n is an integer from 1 to 6 and X is, for example, hydrogen or (C1-C6)-alkyl, R2 is hydrogen or (C1-C6)-alkyl, R3 is hydrogen or phenyl, R4 is, for example, COOR5, where R5 is (C1-C28)-alkyl and Y is, for example, -(CH2)m-CO- radical where m represents an integer from 1 to 4. The compounds of the invention are useful as inhibitors of platelet aggregation, metastasis of carcinoma cells and osteoclast binding to the bone surfaces.
CA002094773A 1992-04-24 1993-04-23 2,4-dioxoimidazolidine derivatives Expired - Lifetime CA2094773C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4213634.2 1992-04-24
DE4213634A DE4213634A1 (en) 1992-04-24 1992-04-24 2,4-dioxo-imidazolidin-derivatives

Publications (2)

Publication Number Publication Date
CA2094773A1 true CA2094773A1 (en) 1993-10-25
CA2094773C CA2094773C (en) 2003-11-04

Family

ID=6457462

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002094773A Expired - Lifetime CA2094773C (en) 1992-04-24 1993-04-23 2,4-dioxoimidazolidine derivatives

Country Status (11)

Country Link
US (1) US5397796A (en)
EP (1) EP0566919B1 (en)
JP (1) JP3793242B2 (en)
AT (1) ATE236886T1 (en)
AU (1) AU665068B2 (en)
CA (1) CA2094773C (en)
CZ (1) CZ287885B6 (en)
DE (2) DE4213634A1 (en)
ES (1) ES2194842T3 (en)
IL (1) IL105511A (en)
SK (1) SK39293A3 (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5494922A (en) * 1993-06-28 1996-02-27 Zeneca Limited Allophanic acid derivatives
US5556977A (en) * 1993-03-29 1996-09-17 Zeneca Limited Heterocyclic derivatives
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
US5563141A (en) * 1993-03-29 1996-10-08 Zeneca Limited Heterocyclic compounds
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 (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4224414A1 (en) * 1992-07-24 1994-01-27 Cassella Ag Phenylimidazolidine derivatives, their preparation and their use
DE4228717A1 (en) * 1992-08-28 1994-03-03 Cassella Ag Imidazolidine derivatives
DE4308034A1 (en) * 1993-03-13 1994-09-15 Cassella Ag New heterocycles, their preparation and their use
DE4427979A1 (en) 1993-11-15 1996-02-15 Cassella Ag Substituted 5-ring heterocycles, their preparation and their use
ES2171768T3 (en) 1996-03-20 2002-09-16 Hoechst Ag OSEA RESORTION INHIBITORS AND VITRONECTINE RECEPTORS ANTAGONISTS.
DE19622489A1 (en) * 1996-06-05 1997-12-11 Hoechst Ag Salts of 3- (2- (4- (4- (aminoimino-methyl) -phenyl) -4-methyl-2,5-dioxo-imidazolidin-1-yl) -acetylamino) -3-phenyl-propionic acid- ethyl esters
DE19629816A1 (en) 1996-07-24 1998-01-29 Hoechst Ag New cycloalkyl derivatives as inhibitors of bone resorption and vitronectin receptor antagonists
DE19629817A1 (en) * 1996-07-24 1998-01-29 Hoechst Ag New imino derivatives as inhibitors of bone resorption and vitronectin receptor antagonists
DE19647380A1 (en) * 1996-11-15 1998-05-20 Hoechst Ag 5-ring heterocycles as inhibitors of leukocyte adhesion and VLA-4 antagonists
DE19741235A1 (en) * 1997-09-18 1999-03-25 Hoechst Marion Roussel De Gmbh Novel imidazolidine derivatives, their preparation, their use and pharmaceutical compositions containing them
DE19741873A1 (en) * 1997-09-23 1999-03-25 Hoechst Marion Roussel De Gmbh New 5-ring heterocycles, their preparation, their use and pharmaceutical preparations containing them
DE19751251A1 (en) * 1997-11-19 1999-05-20 Hoechst Marion Roussel De Gmbh Substituted imidazolidine derivatives, their manufacture, their use and pharmaceutical preparations containing them
DE19821483A1 (en) 1998-05-14 1999-11-18 Hoechst Marion Roussel De Gmbh New imidazolidine derivatives useful as leukocyte adhesion and migration inhibitors and/or VLA-4 receptor antagonists for treating E.G. inflammatory and allergic disorders
DE19922462A1 (en) 1999-05-17 2000-11-23 Aventis Pharma Gmbh New phenylureidobenzyl-substituted spiro-imidazolidinedione derivatives, are inhibitors of leukocyte adhesion or migration or VLA-4 receptors, useful e.g. for treating inflammatory or allergic disease
DE10111877A1 (en) 2001-03-10 2002-09-12 Aventis Pharma Gmbh Novel imidazolidine derivatives, their preparation, their use and pharmaceutical compositions containing them
DE10137595A1 (en) * 2001-08-01 2003-02-13 Aventis Pharma Gmbh New 3-alkylaminoalkyl-imdazolidin-4-one derivatives, are VLA-4 receptor and leukocyte adhesion and/or migration inhibitors, useful e.g. for treating inflammatory, allergic, autoimmune or cardiovascular disease
EP1620092A4 (en) * 2003-05-07 2008-04-16 Cytokinetics Inc Compounds, compositions, and methods
US20060039949A1 (en) * 2004-08-20 2006-02-23 Nycz Jeffrey H Acetabular cup with controlled release of an osteoinductive formulation
US20060045902A1 (en) * 2004-09-01 2006-03-02 Serbousek Jon C Polymeric wrap for in vivo delivery of osteoinductive formulations
US20060057184A1 (en) * 2004-09-16 2006-03-16 Nycz Jeffrey H Process to treat avascular necrosis (AVN) with osteoinductive materials
US9119901B2 (en) * 2005-04-28 2015-09-01 Warsaw Orthopedic, Inc. Surface treatments for promoting selective tissue attachment to medical impants
US8414907B2 (en) 2005-04-28 2013-04-09 Warsaw Orthopedic, Inc. Coatings on medical implants to guide soft tissue healing
US20070077267A1 (en) * 2005-10-03 2007-04-05 Sdgi Holdings, Inc. Bioactive composite implants
US20070179615A1 (en) * 2006-01-31 2007-08-02 Sdgi Holdings, Inc. Intervertebral prosthetic disc
US20070179618A1 (en) * 2006-01-31 2007-08-02 Sdgi Holdings, Inc. Intervertebral prosthetic disc
US20070280986A1 (en) * 2006-06-01 2007-12-06 Carlos Gil Intra-operative coating of implants
US8133553B2 (en) * 2007-06-18 2012-03-13 Zimmer, Inc. Process for forming a ceramic layer
US8309521B2 (en) 2007-06-19 2012-11-13 Zimmer, Inc. Spacer with a coating thereon for use with an implant device
US20110230973A1 (en) * 2007-10-10 2011-09-22 Zimmer, Inc. Method for bonding a tantalum structure to a cobalt-alloy substrate
US8608049B2 (en) * 2007-10-10 2013-12-17 Zimmer, Inc. Method for bonding a tantalum structure to a cobalt-alloy substrate
US20090187256A1 (en) * 2008-01-21 2009-07-23 Zimmer, Inc. Method for forming an integral porous region in a cast implant
AU2008349523B2 (en) * 2008-01-29 2013-10-24 Zimmer, Inc. Implant device for use in an implant system
US20090198286A1 (en) * 2008-02-05 2009-08-06 Zimmer, Inc. Bone fracture fixation system
US11020160B2 (en) 2016-03-21 2021-06-01 Warsaw Orthopedic, Inc. Surgical injection system and method
US10709814B2 (en) 2016-04-22 2020-07-14 Warsaw Orthopedic, Inc. Osteoimplant comprising an insoluble fibrous polymer

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3300510A (en) * 1964-03-06 1967-01-24 American Home Prod Hydantoins
DE2714655A1 (en) * 1977-04-01 1978-10-05 Bayer Ag METHOD OF MANUFACTURING HYDANTOIN
IL57504A0 (en) * 1978-06-15 1979-10-31 Beecham Group Ltd Prostagandin analogues,their preparation and pharmaceutical compositions containing
DE4009506A1 (en) * 1990-03-24 1991-09-26 Hoechst Ag hydantoin
US5100907A (en) * 1990-05-02 1992-03-31 Lonza, Inc. Hydantoin esters
DE4126277A1 (en) * 1991-08-08 1993-02-11 Cassella Ag HYDANTO DERIVATIVES

Cited By (15)

* 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
US5753659A (en) * 1993-03-29 1998-05-19 Zeneca Limited Heterocyclic compouds
US5750754A (en) * 1993-03-29 1998-05-12 Zeneca Limited Heterocyclic compounds
US5563141A (en) * 1993-03-29 1996-10-08 Zeneca Limited Heterocyclic compounds
US5728701A (en) * 1993-03-29 1998-03-17 Zeneca Limited Heterocyclic derivatives
US5556977A (en) * 1993-03-29 1996-09-17 Zeneca Limited Heterocyclic derivatives
US5612373A (en) * 1993-06-28 1997-03-18 Zeneca Limited Certain diacyl hydrazine derivatives
US5576334A (en) * 1993-06-28 1996-11-19 Zeneca Limited Acylurea derivatives
US5494922A (en) * 1993-06-28 1996-02-27 Zeneca Limited Allophanic acid derivatives
US5760057A (en) * 1993-06-28 1998-06-02 Zeneca Limited Certain (piperidin-4-yl-alkanoyl)carbazoyl!-carboxy-phenoxy derivatives
US5981531A (en) * 1993-06-28 1999-11-09 Zeneca Limited Acid derivatives
US5849736A (en) * 1993-11-24 1998-12-15 The Dupont Merck Pharmaceutical Company Isoxazoline and isoxazole 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
AU665068B2 (en) 1995-12-14
IL105511A (en) 1997-02-18
ATE236886T1 (en) 2003-04-15
CZ287885B6 (en) 2001-03-14
US5397796A (en) 1995-03-14
EP0566919A1 (en) 1993-10-27
CZ58693A3 (en) 1994-02-16
DE59310337D1 (en) 2003-05-15
CA2094773C (en) 2003-11-04
EP0566919B1 (en) 2003-04-09
SK39293A3 (en) 1994-02-02
JP3793242B2 (en) 2006-07-05
DE4213634A1 (en) 1993-10-28
ES2194842T3 (en) 2003-12-01
JPH06116245A (en) 1994-04-26
AU3820393A (en) 1993-10-28
IL105511A0 (en) 1993-08-18

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Legal Events

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