WO1995009619A3 - Substituted urea and isothiourea derivatives as no synthase inhibitors - Google Patents

Substituted urea and isothiourea derivatives as no synthase inhibitors Download PDF

Info

Publication number
WO1995009619A3
WO1995009619A3 PCT/GB1994/002138 GB9402138W WO9509619A3 WO 1995009619 A3 WO1995009619 A3 WO 1995009619A3 GB 9402138 W GB9402138 W GB 9402138W WO 9509619 A3 WO9509619 A3 WO 9509619A3
Authority
WO
WIPO (PCT)
Prior art keywords
substituted urea
synthase inhibitors
isothiourea derivatives
derivatives
isothiourea
Prior art date
Application number
PCT/GB1994/002138
Other languages
French (fr)
Other versions
WO1995009619A2 (en
Inventor
Jeffrey Alan Oplinger
Barry George Shearer
Eric Cleveland Bigham
Eric Steven Furfine
Edward Patrick Garvey
Original Assignee
Wellcome Found
Jeffrey Alan Oplinger
Barry George Shearer
Eric Cleveland Bigham
Eric Steven Furfine
Edward Patrick Garvey
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 Wellcome Found, Jeffrey Alan Oplinger, Barry George Shearer, Eric Cleveland Bigham, Eric Steven Furfine, Edward Patrick Garvey filed Critical Wellcome Found
Priority to AU77056/94A priority Critical patent/AU7705694A/en
Priority to JP7510678A priority patent/JPH09504278A/en
Priority to US08/615,291 priority patent/US6090846A/en
Priority to EP94927761A priority patent/EP0723438A1/en
Publication of WO1995009619A2 publication Critical patent/WO1995009619A2/en
Publication of WO1995009619A3 publication Critical patent/WO1995009619A3/en

Links

Classifications

    • 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
    • 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
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • 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
    • A61K31/13—Amines
    • A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • A61P9/10—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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/70—Compounds containing any of the groups, e.g. isoureas
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/30—Isothioureas
    • C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/18—Nitrogen atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Neurosurgery (AREA)
  • Cardiology (AREA)
  • Biomedical Technology (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Urology & Nephrology (AREA)
  • Psychiatry (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The use of an N-substituted urea derivative for the manufacture of a medicament for the treatment of a condition where there is an advantage in inhibiting the NO synthase enzyme, in particular cerebral ischemia, and pharmaceutical formulations therefor are disclosed. Novel N-substituted urea derivatives and processes for the preparation thereof are also described.
PCT/GB1994/002138 1944-06-01 1994-10-03 Substituted urea and isothiourea derivatives as no synthase inhibitors WO1995009619A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU77056/94A AU7705694A (en) 1993-10-04 1994-10-03 Substituted urea and isothiourea derivatives as no synthase inhibitors
JP7510678A JPH09504278A (en) 1944-06-01 1994-10-03 Substituted urea and isothiourea derivatives as NO synthase inhibitors
US08/615,291 US6090846A (en) 1994-06-01 1994-10-03 Substituted urea and isothiourea derivatives as no synthase inhibitors
EP94927761A EP0723438A1 (en) 1993-10-04 1994-10-03 Substituted urea and isothiourea derivatives as no synthase inhibitors

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US13179493A 1993-10-04 1993-10-04
US131,794 1993-10-04
EP94303939.6 1994-06-01
EP94303939 1994-06-01

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US13179493A Continuation 1944-06-01 1993-10-04

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US08/615,291 A-371-Of-International US6090846A (en) 1993-10-04 1994-10-03 Substituted urea and isothiourea derivatives as no synthase inhibitors
US09/514,525 Continuation US6225305B1 (en) 1993-10-04 2000-02-28 Substituted urea and isothiorea derivatives as no synthase inhibitors

Publications (2)

Publication Number Publication Date
WO1995009619A2 WO1995009619A2 (en) 1995-04-13
WO1995009619A3 true WO1995009619A3 (en) 1995-06-15

Family

ID=26137134

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1994/002138 WO1995009619A2 (en) 1944-06-01 1994-10-03 Substituted urea and isothiourea derivatives as no synthase inhibitors

Country Status (4)

Country Link
EP (1) EP0723438A1 (en)
JP (1) JPH09504278A (en)
AU (1) AU7705694A (en)
WO (1) WO1995009619A2 (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8884062B2 (en) 2007-04-24 2014-11-11 Shionogi & Co., Ltd. Aminodihydrothiazine derivatives substituted with a cyclic group
US8895548B2 (en) 2007-04-24 2014-11-25 Shionogi & Co., Ltd. Pharmaceutical composition for treating alzheimer's disease
US8927721B2 (en) 2010-10-29 2015-01-06 Shionogi & Co., Ltd. Naphthyridine derivative
US9018219B2 (en) 2010-10-29 2015-04-28 Shionogi & Co., Ltd. Fused aminodihydropyrimidine derivative
US9273053B2 (en) 2008-06-13 2016-03-01 Shionogi & Co., Ltd. Sulfur-containing heterocyclic derivative having Beta secretase inhibitory activity
US9290466B2 (en) 2009-12-11 2016-03-22 Shionogi & Co., Ltd. Oxazine derivatives
US9540359B2 (en) 2012-10-24 2017-01-10 Shionogi & Co., Ltd. Dihydrooxazine or oxazepine derivatives having BACE1 inhibitory activity

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1823695A (en) * 1994-02-25 1995-09-11 Chugai Seiyaku Kabushiki Kaisha Delta-(s-methylisothioureido)-l-norvaline and cerebrovascular disorder remedy having nitrogen monoxide synthase inhibitor activity
JPH10500138A (en) * 1994-05-07 1998-01-06 アストラ・アクチエボラーグ Bicyclic amidine derivatives as nitric oxide synthase inhibitors
US6124351A (en) * 1994-08-18 2000-09-26 Chugai Seiyaku Kabushiki Kaisha Amino acid derivatives having a nitric oxide synthase inhibiting action
GB9418912D0 (en) * 1994-09-20 1994-11-09 Fisons Corp Pharmaceutically active compounds
WO1996018607A1 (en) 1994-12-12 1996-06-20 Chugai Seiyaku Kabushiki Kaisha Aniline derivative having the effect of inhibiting nitrogen monoxide synthase
TW397812B (en) * 1995-02-11 2000-07-11 Astra Ab Bicyclic isothiourea derivatives useful in therapy
US6140322A (en) * 1995-11-07 2000-10-31 Astra Aktiebolag Amidine and isothiourea derivatives as inhibitors of nitric oxide synthase
TW458978B (en) * 1995-11-07 2001-10-11 Astra Ab Amidine and isothiourea derivatives as inhibitors of nitric oxide synthase
US5929085A (en) * 1996-11-06 1999-07-27 Astra Aktiebolag Amidine and isothiourea derivatives, compositions containing them and their use as inhibitors of nitric oxide synthase
EP0949242A4 (en) 1996-12-24 2004-09-08 Chugai Seiyakukabushiki Kaisha Aromatic amine derivatives having nos inhibitory effect
SE9701681D0 (en) 1997-05-05 1997-05-05 Astra Ab New compounds
US6166030A (en) * 1997-05-05 2000-12-26 Astra Aktiebolag Compounds
CA2366897C (en) 1999-04-06 2009-11-17 Andrew B. Onderdonk Immunomodulatory compositions and methods of use thereof
CA2494323C (en) * 2002-08-07 2011-01-25 Neuraxon Inc. Amino benzothiazole compounds with nos inhibitory activity
US7186725B2 (en) 2003-01-03 2007-03-06 Genzyme Corporation Anti-inflammatory compositions and methods
WO2007049532A1 (en) 2005-10-25 2007-05-03 Shionogi & Co., Ltd. Aminodihydrothiazine derivative
WO2010047372A1 (en) 2008-10-22 2010-04-29 塩野義製薬株式会社 2-aminopyridin-4-one and 2-aminopyridine derivative both having bace1-inhibiting activity
JPWO2010113848A1 (en) 2009-03-31 2012-10-11 塩野義製薬株式会社 Isothiourea derivative or isourea derivative having BACE1 inhibitory action
CN103608345A (en) 2011-04-26 2014-02-26 盐野义制药株式会社 Oxazine derivative and BACE 1 inhibitor containing same
RU2503450C1 (en) * 2012-04-19 2014-01-10 Федеральное Государственное Бюджетное Учреждение "Медицинский Радиологический Научный Центр" Министерства Здравоохранения и Социального Развития Российской Федерации (ФГБУ МРНЦ Минздравсоцразвития России) Anticancer agent
WO2016105448A1 (en) * 2014-12-22 2016-06-30 Darryl Rideout Imidazoline receptor type 1 ligands for use as therapeutics
RU2699558C2 (en) * 2018-10-05 2019-09-06 Федеральное государственное бюджетное учреждение "Национальный медицинский исследовательский центр радиологии" Министерства здравоохранения Российской Федерации (ФГБУ "НМИЦ Радиологии" Минздрава России РФ) Agent for targeted therapy of malignant growths

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1532212A (en) * 1963-07-05 1968-07-12 Bayer Ag Process for manufacturing 2-phenylamino-4h-5, 6-dihydro-1, 3-thiazine derivatives
GB1178242A (en) * 1966-02-05 1970-01-21 Wellcome Found Novel Biologically Active Bis-Isothioureas
NL7703011A (en) * 1976-03-19 1977-09-21 Mcneilab Inc PROCESS FOR PREPARING 1-AZACARBOCYCLICAL 2-YLIDEEN DERIVATIVES OF GUANIDINE, PROCEDURE FOR PREPARING A PHARMACEUTICAL PREPARATION USING IT AND SUCH PREPARATION.
EP0202157A1 (en) * 1985-04-30 1986-11-20 Laboratoires Chauvin S.A. N-substituted 2-amino-thiazoles, process for their preparation and their therapeutical use
EP0392802A2 (en) * 1989-04-11 1990-10-17 Beecham Group p.l.c. Preparation of urea analogues and their use in bronchial, cerebrovascular and neuronal disorders
EP0411615A1 (en) * 1989-08-02 1991-02-06 Warner-Lambert Company 4-(N-substituted amino)-2-butynyl-1-ureas and thioureas and derivatives thereof as centrally acting muscarinic agents
EP0446699A1 (en) * 1990-02-26 1991-09-18 Merrell Pharmaceuticals Inc. Inhibitors of nitric oxide biosynthesis
WO1992014453A1 (en) * 1991-02-26 1992-09-03 Arc 1, Inc. Compositions and methods of treatment of sympathetically maintained pain

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1532212A (en) * 1963-07-05 1968-07-12 Bayer Ag Process for manufacturing 2-phenylamino-4h-5, 6-dihydro-1, 3-thiazine derivatives
GB1178242A (en) * 1966-02-05 1970-01-21 Wellcome Found Novel Biologically Active Bis-Isothioureas
NL7703011A (en) * 1976-03-19 1977-09-21 Mcneilab Inc PROCESS FOR PREPARING 1-AZACARBOCYCLICAL 2-YLIDEEN DERIVATIVES OF GUANIDINE, PROCEDURE FOR PREPARING A PHARMACEUTICAL PREPARATION USING IT AND SUCH PREPARATION.
EP0202157A1 (en) * 1985-04-30 1986-11-20 Laboratoires Chauvin S.A. N-substituted 2-amino-thiazoles, process for their preparation and their therapeutical use
EP0392802A2 (en) * 1989-04-11 1990-10-17 Beecham Group p.l.c. Preparation of urea analogues and their use in bronchial, cerebrovascular and neuronal disorders
EP0411615A1 (en) * 1989-08-02 1991-02-06 Warner-Lambert Company 4-(N-substituted amino)-2-butynyl-1-ureas and thioureas and derivatives thereof as centrally acting muscarinic agents
EP0446699A1 (en) * 1990-02-26 1991-09-18 Merrell Pharmaceuticals Inc. Inhibitors of nitric oxide biosynthesis
WO1992014453A1 (en) * 1991-02-26 1992-09-03 Arc 1, Inc. Compositions and methods of treatment of sympathetically maintained pain

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 9238, Derwent World Patents Index; AN 92-315914 *
DAWSON, V.L. ET AL: "NITRIC OXIDE MEDIATES GLUTAMATE TOXICITY IN PRIMARY CORTICAL CULTURES", PROCEEDINGS NATIONAL ACADEMY OF SCIENCES USA, vol. 88, July 1991 (1991-07-01), pages 6368 - 6371 *
MANLEY, P.W. ET AL: "STRUCTURE ACTIVITY RELATIONSHIPS OF POTASSIUM CHANNEL OPENING IN PINACIDIL-TYPE CYANOGUANIDINES, NITROETHENEDIAMINES, THIOUREAS AND UREAS", JOURNAL OF MEDICINAL CHEMISTRY, vol. 35, 1992, pages 2327 - 2340 *
RASMUSSEN, C.R. ET AL: "A VERSATILE SYNTHESIS OF NOVEL N,N,N'-TRISUBSTITUTED GUANIDINES", SYNTHESIS, vol. 6, June 1988 (1988-06-01), pages 460 - 466 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8884062B2 (en) 2007-04-24 2014-11-11 Shionogi & Co., Ltd. Aminodihydrothiazine derivatives substituted with a cyclic group
US8895548B2 (en) 2007-04-24 2014-11-25 Shionogi & Co., Ltd. Pharmaceutical composition for treating alzheimer's disease
US9273053B2 (en) 2008-06-13 2016-03-01 Shionogi & Co., Ltd. Sulfur-containing heterocyclic derivative having Beta secretase inhibitory activity
US9290466B2 (en) 2009-12-11 2016-03-22 Shionogi & Co., Ltd. Oxazine derivatives
US8927721B2 (en) 2010-10-29 2015-01-06 Shionogi & Co., Ltd. Naphthyridine derivative
US9018219B2 (en) 2010-10-29 2015-04-28 Shionogi & Co., Ltd. Fused aminodihydropyrimidine derivative
US9540359B2 (en) 2012-10-24 2017-01-10 Shionogi & Co., Ltd. Dihydrooxazine or oxazepine derivatives having BACE1 inhibitory activity

Also Published As

Publication number Publication date
EP0723438A1 (en) 1996-07-31
AU7705694A (en) 1995-05-01
JPH09504278A (en) 1997-04-28
WO1995009619A2 (en) 1995-04-13

Similar Documents

Publication Publication Date Title
WO1995009619A3 (en) Substituted urea and isothiourea derivatives as no synthase inhibitors
WO1994012165A3 (en) Enzyme inhibitors
AU6328094A (en) Saccharin derivative proteolytic enzyme inhibitors
TW225532B (en)
CA2293706A1 (en) N-substituted urea inhibitors of farnesyl-protein transferase
IE893894L (en) Pharmaceutically active cns compounds
HUP0004421A3 (en) Urea derivatives and pharmaceutical compositions containing them, use thereof for the treatment of deseases mediated by impdh enzyme
AU6194894A (en) Bile acid derivatives, processes for their preparation and the use of these compounds as medicaments
CA2216796A1 (en) Quinazoline derivatives
WO2004005286A3 (en) Viral inhibitors
EP0216539A3 (en) Novel amino acid derivatives
AU4180900A (en) Novel amide derivatives as inhibitors of matrix metalloproteinases, tnf-alpha, and aggrecanase
EP0200406A3 (en) Novel amino acid derivatives
EP0206807A3 (en) Novel amino acid derivatives
AU644621B2 (en) Pharmaceutical composition for treating or preventing retroviral infections
IE890748L (en) Peptides with pharmaceutical activity
WO1990003172A3 (en) Bile acids for treatment of viral infections
MXPA01004457A (en) Novel pyrimidine derivatives and processes for the preparation thereof.
HUT53122A (en) Process for producing renin inhibiting dipeptide urea derivatives and pharmaceutical compositions comprising same as active ingredient
AU8730991A (en) Derivatives of amino acids as inhibitors of renin, methods for their preparation, medicaments containing them and their use
AU6970394A (en) Desoxyazaphospholipid derivatives having inhibiting activity on phospholipase a2
EP1295874A3 (en) Retroviral protease inhibiting compounds
IE872218L (en) Nicotinamide derivative as a therapeutic agent
WO1998023574A8 (en) Asiatic acid derivatives and medicines for treating wounds, which contains the same
AU2001284477A1 (en) Novel crystals of N-hydroxy-2(S)-methyl-5-ethoxymethoxy -4(S)-(N-(4-phenoxyphenylcarbonyl)amino]pentanamide, process for their production and medicines containing the crystals as the active ingredient

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AU BR CA CN CZ FI GE HU JP KR KZ LT NO NZ PL RU SI SK UA US UZ

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): AU BR CA CN CZ FI GE HU JP KR KZ LT NO NZ PL RU SI SK UA US UZ

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1994927761

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 08615291

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 1994927761

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: CA

WWR Wipo information: refused in national office

Ref document number: 1994927761

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1994927761

Country of ref document: EP