ES2203988T3 - Compuestos de pirimidinona y composiciones farmaceuticas que los contienen. - Google Patents

Compuestos de pirimidinona y composiciones farmaceuticas que los contienen.

Info

Publication number
ES2203988T3
ES2203988T3 ES98954482T ES98954482T ES2203988T3 ES 2203988 T3 ES2203988 T3 ES 2203988T3 ES 98954482 T ES98954482 T ES 98954482T ES 98954482 T ES98954482 T ES 98954482T ES 2203988 T3 ES2203988 T3 ES 2203988T3
Authority
ES
Spain
Prior art keywords
group
alkoxy
alkyl
compounds
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.)
Expired - Lifetime
Application number
ES98954482T
Other languages
English (en)
Inventor
Deirdre Mary Bernadette Smithkline Hickey
Robert John Smithkline Beecham Ife
Colin Andrew SmithKline Beecham LEACH
Ivan Leo SmithKline Beecham PINTO
Roderick Alan Smithkline Beecham Porter
Stephen Allan SmithKline Beecham SMITH
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.)
SmithKline Beecham Ltd
Original Assignee
SmithKline Beecham Ltd
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
Priority claimed from GBGB9723352.2A external-priority patent/GB9723352D0/en
Priority claimed from GBGB9723358.9A external-priority patent/GB9723358D0/en
Application filed by SmithKline Beecham Ltd filed Critical SmithKline Beecham Ltd
Application granted granted Critical
Publication of ES2203988T3 publication Critical patent/ES2203988T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • 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
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • 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
    • A61P9/10—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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—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
    • C07D405/02—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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Diabetes (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Rheumatology (AREA)
  • Psychiatry (AREA)
  • Vascular Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Urology & Nephrology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Hospice & Palliative Care (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Compuestos de la **fórmula** en la que: Z es un enlace y R1 es halógeno; o Z es CR3R4, donde R3 y R4 son cada uno hidrógeno o un alquilo C(1-4), o R3 y R4 junto con el átomo de carbono que interviene, forman un anillo cicloalquilo C(3-6); y R1 es un grupo arilo o heteroarilo, opcionalmente sustituido con 1, 2, 3 o 4 sustituyentes seleccionados entre alquilo C(1-18), alcoxi C(1-18), tioalquilo C(1-18), alcoxi C(1-18)-arilo, oxo, hidroxi, halógeno, CN, COR5, COOR5, CONR5R6, NR5COR6, SO2NR5R6, NR5SO2R6, NR5R6, monofluoro-alquilo C(1-4) a perfluoro-alquilo C(1-4) y monofluoro-alcoxi C(1-4) a perfluoro-alcoxi C(1-4); X es O o S; Y es un grupo de fórmula -A1-A2-A3- en la que A1 y A3 representan cada uno un enlace o un grupo alquileno C(1-10) de cadena lineal o ramificada y A2 representa un enlace o es O, S, SO, SO2, CO, C=CH2, CH=CH, CC, CONH, NHCO o CR5R6, a condición de que cuando A2 es O, S, SO, SO2 o CONH, A3 contiene como mínimo dos átomos de carbono que unen el grupo A2 y el grupo CH2 de lafórmula (I).
ES98954482T 1997-11-06 1998-10-23 Compuestos de pirimidinona y composiciones farmaceuticas que los contienen. Expired - Lifetime ES2203988T3 (es)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GBGB9723352.2A GB9723352D0 (en) 1997-11-06 1997-11-06 Novel compounds
GBGB9723358.9A GB9723358D0 (en) 1997-11-06 1997-11-06 Novel compounds
GB9723358 1997-11-06
GB9723352 1997-11-06

Publications (1)

Publication Number Publication Date
ES2203988T3 true ES2203988T3 (es) 2004-04-16

Family

ID=26312554

Family Applications (1)

Application Number Title Priority Date Filing Date
ES98954482T Expired - Lifetime ES2203988T3 (es) 1997-11-06 1998-10-23 Compuestos de pirimidinona y composiciones farmaceuticas que los contienen.

Country Status (9)

Country Link
US (2) US6417192B1 (es)
EP (1) EP1028955B1 (es)
JP (1) JP2001522844A (es)
AR (1) AR016666A1 (es)
AU (1) AU1157599A (es)
CA (1) CA2309177A1 (es)
DE (1) DE69816471T2 (es)
ES (1) ES2203988T3 (es)
WO (1) WO1999024420A1 (es)

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* Cited by examiner, † Cited by third party
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US6559155B1 (en) 1998-08-21 2003-05-06 Smithkline Beecham P.L.C. Pyrimidinone derivatives for the treatment of atherosclerosis
GB9910079D0 (en) * 1999-05-01 1999-06-30 Smithkline Beecham Plc Novel compounds
US6953803B1 (en) 1999-05-01 2005-10-11 Smithkline Beecham P.L.C. Pyrimidine compounds
GB9910378D0 (en) * 1999-05-05 1999-06-30 Smithkline Beecham Plc Novel compounds
ATE333446T1 (de) 2000-02-16 2006-08-15 Smithkline Beecham Plc Pyrimidin-4-onderivat als ldl-pla2 inhibitor
GB0024808D0 (en) * 2000-10-10 2000-11-22 Smithkline Beecham Plc Novel compounds
GB0024807D0 (en) 2000-10-10 2000-11-22 Smithkline Beecham Plc Novel compounds
GB0119793D0 (en) * 2001-08-14 2001-10-03 Smithkline Beecham Plc Novel compounds
GB0127143D0 (en) * 2001-11-10 2002-01-02 Smithkline Beecham Novel compounds
GB0127139D0 (en) * 2001-11-10 2002-01-02 Smithkline Beecham Novel compounds
GB0208279D0 (en) * 2002-04-10 2002-05-22 Glaxo Group Ltd Novel compounds
GB0208280D0 (en) * 2002-04-10 2002-05-22 Glaxo Group Ltd Novel compounds
KR101690390B1 (ko) 2007-05-11 2016-12-27 토마스 제퍼슨 유니버시티 신경변성 질환 및 장애의 치료 및 예방 방법
EA018101B1 (ru) 2007-05-11 2013-05-30 Дзе Трастиз Оф Дзе Юниверсити Оф Пенсильвания Способы лечения кожных язв
US8691866B2 (en) 2008-12-10 2014-04-08 The General Hospital Corporation HIF inhibitors and use thereof
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AU2011340690C1 (en) 2010-12-06 2016-03-10 Glaxo Group Limited Pyrimidinone compounds for use in the treatment of diseases or conditions mediated by Lp - PLA2
JP2013544854A (ja) * 2010-12-06 2013-12-19 グラクソ グループ リミテッド 化合物
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EP2948452B1 (en) 2013-01-25 2017-08-09 GlaxoSmithKline Intellectual Property Development Limited 2,3-dihydroimidazol[1,2-c]pyrimidin-5(1h)-one based lipoprotein-associated phospholipase a2 (lp-pla2) inhibitors
KR20150108896A (ko) 2013-01-25 2015-09-30 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 Lp-pla2의 억제제로서의 비시클릭 피리미돈 화합물
CN105008365B (zh) 2013-01-25 2017-03-15 葛兰素史密斯克莱知识产权发展有限公司 化合物
WO2016012917A1 (en) 2014-07-22 2016-01-28 Glaxosmithkline Intellectual Property Development Limited 1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidine derivatives useful in the treatment of diseases and disorders mediated by lp-pla2
WO2016012916A1 (en) 2014-07-22 2016-01-28 Glaxosmithkline Intellectual Property Development Limited 1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidine derivatives useful in the treatment of diseases and disorders mediated by lp-pla2
DK3287443T3 (da) * 2015-04-24 2022-02-07 Shionogi & Co 6-leddet heterocyklisk derivat og farmaceutisk sammensætning, som omfatter dette
EP3133065A1 (en) 2015-08-21 2017-02-22 Merck Patent GmbH Compounds for optically active devices
JP6692113B2 (ja) * 2016-10-21 2020-05-13 塩野義製薬株式会社 ６員複素環誘導体を含有する医薬組成物
EP3363793A1 (en) 2017-02-15 2018-08-22 Merck Patent GmbH Hydrophobic compounds for optically active devices
CN107382726A (zh) * 2017-08-02 2017-11-24 东南大学成贤学院 一种(e)‑2‑(甲氧基亚甲基)‑4‑芳基正丁酯的制备方法
WO2021089032A1 (zh) 2019-11-09 2021-05-14 上海赛默罗生物科技有限公司 三环二氢咪唑并嘧啶酮衍生物、其制备方法、药物组合物和用途
KR20230041041A (ko) 2020-07-15 2023-03-23 에이엠오 아일랜드 광학적으로 활성인 장치
CN115304620A (zh) 2021-05-07 2022-11-08 上海赛默罗生物科技有限公司 嘧啶酮衍生物、其制备方法、药物组合物和用途

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Also Published As

Publication number Publication date
WO1999024420A1 (en) 1999-05-20
EP1028955B1 (en) 2003-07-16
CA2309177A1 (en) 1999-05-20
EP1028955A1 (en) 2000-08-23
DE69816471D1 (de) 2003-08-21
AU1157599A (en) 1999-05-31
DE69816471T2 (de) 2004-05-27
JP2001522844A (ja) 2001-11-20
AR016666A1 (es) 2001-07-25
US6417192B1 (en) 2002-07-09
US20020120139A1 (en) 2002-08-29

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