CA2189131A1 - Use of pteridine derivatives as no-synthase inhibitors - Google Patents

Use of pteridine derivatives as no-synthase inhibitors

Info

Publication number
CA2189131A1
CA2189131A1 CA002189131A CA2189131A CA2189131A1 CA 2189131 A1 CA2189131 A1 CA 2189131A1 CA 002189131 A CA002189131 A CA 002189131A CA 2189131 A CA2189131 A CA 2189131A CA 2189131 A1 CA2189131 A1 CA 2189131A1
Authority
CA
Canada
Prior art keywords
synthase inhibitors
pteridine derivatives
nitric oxide
formula
pteridine
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
CA002189131A
Other languages
French (fr)
Other versions
CA2189131C (en
Inventor
Wolfgang Pfleiderer
Harald Schmidt
Rainer Henning
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.)
Verinos Operations GmbH
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2189131A1 publication Critical patent/CA2189131A1/en
Application granted granted Critical
Publication of CA2189131C publication Critical patent/CA2189131C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/99—Enzyme inactivation by chemical treatment
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D475/00—Heterocyclic compounds containing pteridine ring systems
    • C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4
    • C07D475/04—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D475/00—Heterocyclic compounds containing pteridine ring systems
    • C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
    • C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2

Abstract

The present invention relates to the use of pteridine derivatives of the formula I
(see formula I) in which X is O, NH or N-(C1-C5)-alkanoyl, R3 is the radical -OR4, -NR5R6 or -S(O)m R7, and R, R1, R2, R4, R5, R6, R7 and m have the meanings given in claim 1, which are nitric oxide synthase inhibitors, for the treatment of diseases which are caused by an increased nitric oxide level.
CA002189131A 1994-05-24 1995-05-06 Use of pteridine derivatives as no-synthase inhibitors Expired - Lifetime CA2189131C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DEP4418096.9 1994-05-24
DE4418096A DE4418096A1 (en) 1994-05-24 1994-05-24 Use of pteridine derivatives as inhibitors of NO synthase
PCT/EP1995/001731 WO1995031987A1 (en) 1994-05-24 1995-05-06 Use of pteridine derivatives as no-synthase inhibitors

Publications (2)

Publication Number Publication Date
CA2189131A1 true CA2189131A1 (en) 1995-11-30
CA2189131C CA2189131C (en) 2007-03-06

Family

ID=6518841

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002189131A Expired - Lifetime CA2189131C (en) 1994-05-24 1995-05-06 Use of pteridine derivatives as no-synthase inhibitors

Country Status (9)

Country Link
US (1) US5902810A (en)
EP (1) EP0760664B1 (en)
JP (1) JP4138870B2 (en)
AT (1) ATE223220T1 (en)
CA (1) CA2189131C (en)
DE (2) DE4418096A1 (en)
ES (1) ES2180633T3 (en)
PT (1) PT760664E (en)
WO (1) WO1995031987A1 (en)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0897912A1 (en) * 1993-10-21 1999-02-24 G.D. Searle & Co. Amidino derivatives useful as nitric oxide synthase inhibitors
AU712315B2 (en) * 1995-04-20 1999-11-04 G.D. Searle & Co. Cyclic amidino agents useful as nitric oxide synthase inhibitors
US5945408A (en) * 1996-03-06 1999-08-31 G.D. Searle & Co. Hydroxyanidino derivatives useful as nitric oxide synthase inhibitors
US6162806A (en) * 1996-07-31 2000-12-19 Artemis, Inc. Active oxygen scavengers containing pterin derivatives
US5922713A (en) * 1997-06-26 1999-07-13 Werner; Ernst Inhibition of nitric oxide synthase
US5981556A (en) * 1997-07-22 1999-11-09 G.D. Searle & Co. 1,3-diazolino and 1,3-diazolidino heterocycles as useful nitric oxide synthase inhibitors
DE59703603D1 (en) * 1997-10-06 2001-06-28 Ernst Werner Pteridine derivatives as NO synthase inhibitors
CA2319495A1 (en) * 1998-06-08 1999-12-16 Advanced Medicine, Inc. Multibinding inhibitors of microsomal triglyceride transferase protein
US6489323B1 (en) 1998-06-10 2002-12-03 G.D. Searle & Co. Heterobicyclic and tricyclic nitric oxide synthase inhibitors
US7276506B2 (en) 1998-12-28 2007-10-02 4 Aza Bioscience Nv Immunosuppressive effects of pteridine derivatives
AU770551B2 (en) * 1998-12-28 2004-02-26 4-Aza Bioscience Nv Immunosuppressive effects of pteridine derivatives
DE19944767A1 (en) * 1999-09-17 2001-03-29 Vasopharm Biotech Gmbh & Co Kg N-substituted 4-aminopteridines, process for their preparation and their use as medicines
US6344473B1 (en) 2000-08-07 2002-02-05 G.D. Searle & Co. Imidazoles useful as nitric oxide synthase inhibitors
WO2002076954A1 (en) * 2001-03-23 2002-10-03 Smithkline Beecham Corporation Compounds useful as kinase inhibitors for the treatment of hyperproliferative diseases
BR0315008A (en) * 2002-10-04 2005-08-09 Prana Biotechnology Ltd Neurologically Active Compounds
WO2005037286A1 (en) * 2003-03-25 2005-04-28 Vasopharm Biotech Gmbh Use of pteridine derivatives for the treatment of increased intracranial pressure and secondary ischemia
GB2405793A (en) * 2003-09-12 2005-03-16 4 Aza Bioscience Nv Pteridine derivatives for treating TNF-alpha related disorders
PL3138566T3 (en) * 2003-11-17 2022-03-07 Biomarin Pharmaceutical Inc. Treatment of phenylketonuria with bh4
AU2005306686B2 (en) 2004-11-17 2011-06-02 Biomarin Pharmaceutical Inc. Stable tablet formulation of tetrahydrobiopterin
BRPI0710737A2 (en) * 2006-04-14 2011-05-10 Prana Biotechnology Ltd use of compounds pb-10 33 useful for the treatment of age-related macular degeneration (amd) as well as said compounds
US10144736B2 (en) 2006-07-20 2018-12-04 Gilead Sciences, Inc. Substituted pteridines useful for the treatment and prevention of viral infections
ES2773931T3 (en) 2008-06-05 2020-07-15 Bausch Health Ireland Ltd Topical pharmaceutical formulations containing a low concentration of benzoyl peroxide suspended in water and a water-miscible organic solvent
US9216178B2 (en) 2011-11-02 2015-12-22 Biomarin Pharmaceutical Inc. Dry blend formulation of tetrahydrobiopterin
SI3321265T1 (en) 2015-03-04 2020-07-31 Gilead Sciences, Inc. 4,6-diamino-pyrido(3,2-d)pyrimidine compounds and their utilisation as modulators of toll-like receptors
WO2018045150A1 (en) 2016-09-02 2018-03-08 Gilead Sciences, Inc. 4,6-diamino-pyrido[3,2-d]pyrimidine derivaties as toll like receptor modulators
PT3507276T (en) 2016-09-02 2022-01-11 Gilead Sciences Inc Toll like receptor modulator compounds
TW202212339A (en) 2019-04-17 2022-04-01 美商基利科學股份有限公司 Solid forms of a toll-like receptor modulator
TW202210480A (en) 2019-04-17 2022-03-16 美商基利科學股份有限公司 Solid forms of a toll-like receptor modulator
TW202115056A (en) 2019-06-28 2021-04-16 美商基利科學股份有限公司 Processes for preparing toll-like receptor modulator compounds

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Publication number Priority date Publication date Assignee Title
US4079056A (en) * 1975-03-31 1978-03-14 The United States Of America As Represented By The Department Of Health, Education And Welfare Method of making pteridine compounds
DK426083A (en) * 1982-09-20 1984-03-21 Wellcome Found PTERINES, PROCEDURES FOR THEIR PREPARATION AND THEIR USE
DK160827C (en) * 1984-02-03 1991-10-14 Res Corp Technologies Inc PTERIDIN DERIVATIVES, PROCEDURES FOR PREPARING THEM AND PHARMACEUTICAL PREPARATION
IT1204612B (en) * 1987-05-14 1989-03-10 Bioresearch Spa PTERIDINS SUITABLE FOR THE PREPARATION OF PHARMACEUTICAL COMPOSITIONS FOR ANTI-MAGNESIC ACTIVITIES
JP2534423B2 (en) * 1991-12-26 1996-09-18 コーネル・リサーチ・ファンデーション・インコーポレイテッド Inhibitors that prevent vascular disorders resulting from overproduction of nitric oxide
JPH0656669A (en) * 1992-06-11 1994-03-01 Asahi Breweries Ltd Pterine derivative preparation having active oxygen-scavenging action
AU5704594A (en) * 1992-12-18 1994-07-19 Wellcome Foundation Limited, The Pyrimidine, pyridine, pteridinone and indazole derivatives as enzyme inhibitors
JPH0834782A (en) * 1994-05-20 1996-02-06 Nissan Chem Ind Ltd Imino-type sulfonylurea and herbicide

Also Published As

Publication number Publication date
PT760664E (en) 2003-01-31
DE59510362D1 (en) 2002-10-10
WO1995031987A1 (en) 1995-11-30
ES2180633T3 (en) 2003-02-16
EP0760664B1 (en) 2002-09-04
JP4138870B2 (en) 2008-08-27
US5902810A (en) 1999-05-11
ATE223220T1 (en) 2002-09-15
DE4418096A1 (en) 1995-11-30
JPH10504023A (en) 1998-04-14
CA2189131C (en) 2007-03-06
EP0760664A1 (en) 1997-03-12

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