AU2001273062B2 - Substituted-triazolopyrimidines as anticancer agents - Google Patents

Substituted-triazolopyrimidines as anticancer agents Download PDF

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Publication number
AU2001273062B2
AU2001273062B2 AU2001273062A AU2001273062A AU2001273062B2 AU 2001273062 B2 AU2001273062 B2 AU 2001273062B2 AU 2001273062 A AU2001273062 A AU 2001273062A AU 2001273062 A AU2001273062 A AU 2001273062A AU 2001273062 B2 AU2001273062 B2 AU 2001273062B2
Authority
AU
Australia
Prior art keywords
chloro
carbon atoms
triazolo
optionally substituted
amine
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.)
Ceased
Application number
AU2001273062A
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English (en)
Other versions
AU2001273062A1 (en
Inventor
Guido Albert
Carl F. Beyer
Paul Carter
Jane E. Harris
Donald R. Kirsch
Klaus-Juergen Pees
Waldemar Pfrengle
Mark R. Schmitt
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Wyeth LLC
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Wyeth LLC
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Publication date
Application filed by Wyeth LLC filed Critical Wyeth LLC
Publication of AU2001273062A1 publication Critical patent/AU2001273062A1/en
Application granted granted Critical
Publication of AU2001273062B2 publication Critical patent/AU2001273062B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
AU2001273062A 2000-06-30 2001-06-28 Substituted-triazolopyrimidines as anticancer agents Ceased AU2001273062B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US21558500P 2000-06-30 2000-06-30
US60/215,585 2000-06-30
PCT/US2001/020672 WO2002002563A2 (en) 2000-06-30 2001-06-28 Substituted-triazolopyrimidines as anticancer agents

Publications (2)

Publication Number Publication Date
AU2001273062A1 AU2001273062A1 (en) 2002-04-11
AU2001273062B2 true AU2001273062B2 (en) 2005-11-24

Family

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Family Applications (2)

Application Number Title Priority Date Filing Date
AU2001273062A Ceased AU2001273062B2 (en) 2000-06-30 2001-06-28 Substituted-triazolopyrimidines as anticancer agents
AU7306201A Pending AU7306201A (en) 2000-06-30 2001-06-28 Substituted-triazolopyrimidines as anticancer agents

Family Applications After (1)

Application Number Title Priority Date Filing Date
AU7306201A Pending AU7306201A (en) 2000-06-30 2001-06-28 Substituted-triazolopyrimidines as anticancer agents

Country Status (24)

Country Link
US (1) US7329663B2 (https=)
EP (1) EP1307200A2 (https=)
JP (1) JP2004502691A (https=)
KR (1) KR20030013475A (https=)
CN (1) CN1592624A (https=)
AR (1) AR034553A1 (https=)
AU (2) AU2001273062B2 (https=)
BG (1) BG107277A (https=)
BR (1) BR0112038A (https=)
CA (1) CA2413802A1 (https=)
CZ (1) CZ20024150A3 (https=)
EA (1) EA006483B1 (https=)
GE (1) GEP20053688B (https=)
HK (1) HK1052646A1 (https=)
HU (1) HUP0300798A3 (https=)
IL (1) IL152869A0 (https=)
IN (1) IN2003KO00001A (https=)
MX (1) MXPA02011913A (https=)
NO (1) NO20026195L (https=)
NZ (1) NZ523807A (https=)
PL (1) PL360027A1 (https=)
SK (1) SK18412002A3 (https=)
WO (1) WO2002002563A2 (https=)
ZA (1) ZA200300793B (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2002257757B2 (en) * 2001-04-11 2008-05-08 Basf Aktiengesellschaft 5-Halogen-6-phenyl-7-fluoralkylamino-triazolopyrimidines as fungicides

Families Citing this family (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6255309B1 (en) * 1999-03-19 2001-07-03 American Cyanomid Co. Fungicidal trifluoromethylalkylamino-triazolopyrimidines
JP2004513170A (ja) * 2000-11-13 2004-04-30 ビーエーエスエフ　アクチェンゲゼルシャフト ７−（ｒ）−アミノトリアゾロピリミジン類、それらの製造及び植物病原性真菌を防除するためのそれらの使用
WO2002083677A1 (en) * 2001-04-11 2002-10-24 Basf Aktiengesellschaft 6-(2-chloro-6-fluoro-phenyl)-triazolopyrimidines
DE10121101A1 (de) * 2001-04-27 2002-10-31 Bayer Ag Triazolopyrimidine
DE10121162A1 (de) * 2001-04-30 2002-10-31 Bayer Ag Triazolopyrimidine
DE10124208A1 (de) 2001-05-18 2002-11-21 Bayer Ag Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide
US20040162286A1 (en) * 2001-07-18 2004-08-19 Tormo I Blasco Jordi Substituted 6-(2-tolyl)-triazolopyrimidines as fungicides
CA2479766A1 (en) * 2002-03-21 2003-10-02 Basf Aktiengesellschaft Fungicidal triazolopyrimidines, methods for producing the same, use thereof for combating harmful fungi and agents containing said substances
JPWO2004011467A1 (ja) * 2002-07-29 2005-12-15 北興化学工業株式会社 トリアゾロピリミジン誘導体および農園芸用殺菌剤
UA80304C2 (en) * 2002-11-07 2007-09-10 Basf Ag Substituted 6-(2-halogenphenyl)triazolopyrimidines
WO2004087705A1 (de) * 2003-03-31 2004-10-14 Basf Aktiengesellschaft 7-alkenylamino-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel
WO2004108136A1 (en) * 2003-06-04 2004-12-16 Vernalis (Cambridge) Limited Triazolo `1 , 5-a!pyrimidines and their use in medicine
DE10325133A1 (de) * 2003-06-04 2004-12-23 Bayer Cropscience Ag Triazolopyrimidine
DE10328173A1 (de) * 2003-06-24 2005-01-13 Bayer Cropscience Ag Triazolopyrimidine
DE10328171A1 (de) * 2003-06-24 2005-01-13 Bayer Cropscience Ag Triazolopyrimidine
DE10328481A1 (de) * 2003-06-25 2005-01-13 Bayer Ag Triazolopyrimidine
US7419982B2 (en) 2003-09-24 2008-09-02 Wyeth Holdings Corporation Crystalline forms of 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine salts
SI1680425T1 (sl) * 2003-09-24 2007-04-30 Wyeth Corp 6-((substituirani)fenil)triazolopirimidini kot sredstva proti raku
ES2308256T3 (es) * 2003-09-24 2008-12-01 Wyeth Holdings Corporation 6-aril-7-halo-imidazo(1,2-a)pirimidinas como agentes anticancerosos.
WO2005037837A1 (ja) * 2003-10-17 2005-04-28 Nippon Kayaku Kabushiki Kaisha 置換２−アミノ−[１，２，４]トリアゾロ[１，５−a]ピリミジン誘導体及びその用途
JP4606015B2 (ja) * 2003-11-25 2011-01-05 日本化薬株式会社 ［１，２，４］トリアゾロ［１，５−ａ］ピリミジン誘導体の新規医薬用途
MY179926A (en) 2003-12-08 2020-11-19 Wyeth Corp Process for the preparation of tubulin inhibitors
JP2007514680A (ja) * 2003-12-17 2007-06-07 ビーエーエスエフ　アクチェンゲゼルシャフト ６−（２，４，６−トリハロフェニル）トリアゾロピリミジン、その製造方法、および植物病原性真菌類を防除するためのその使用、ならびにその物質を含有している農薬
CN1894254A (zh) * 2003-12-17 2007-01-10 巴斯福股份公司 用于防治病原性真菌的6－(2,3,6－三氟苯基)三唑并嘧啶
BRPI0508717A (pt) * 2004-03-30 2007-08-07 Basf Ag compostos, processo para preparar os mesmos, agente, semente, e, processo para combater fungos nocivos fitopatogênicos
EP1751162A1 (de) * 2004-05-17 2007-02-14 Basf Aktiengesellschaft Triazolopyrimidin-verbindungen und ihre verwendung zur bekämpfung von schadpilzen
US20070249634A1 (en) * 2004-06-09 2007-10-25 Carsten Blettner Triazolopyrimidine Compounds and Use Thereof for Controlling Harmful Fungi
KR20070024646A (ko) * 2004-06-25 2007-03-02 바스프 악티엔게젤샤프트 트리아졸로피리미딘 화합물 및 그의 병원성 진균류 방제를위한 용도
CA2608890C (en) * 2005-05-20 2011-08-02 Alantos-Pharmaceuticals, Inc. Heterobicyclic metalloprotease inhibitors
US20070155738A1 (en) * 2005-05-20 2007-07-05 Alantos Pharmaceuticals, Inc. Heterobicyclic metalloprotease inhibitors
WO2007011759A2 (en) * 2005-07-15 2007-01-25 Kalypsys, Inc. Inhibitors of mitotic kinesin
WO2007075465A1 (en) * 2005-12-16 2007-07-05 Wyeth Dimers and adducts of 6-[(substituted) phenyl] triazolopyrimidines useful as anticancer agents
TW200800026A (en) * 2006-02-28 2008-01-01 Basf Ag Substituted 6-phenyl-7-amino-[1,2,4]-triazolo[1,5-a] pyrimidines and their use for controlling harmful fungi
WO2007116011A2 (de) * 2006-04-10 2007-10-18 Basf Se Substituierte triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel
JP5231829B2 (ja) 2007-02-15 2013-07-10 石原産業株式会社 ピリジル−トリアゾロピリミジン誘導体又はその塩、それらを含有する有害生物防除剤並びにそれらの製造方法
PT2188291E (pt) 2007-08-14 2012-12-20 Bayer Ip Gmbh Pirimidinas bicíclicas fundidas
WO2012047856A2 (en) 2010-10-04 2012-04-12 Institute For Hepatitis And Virus Research Novel inhibitors of secretion of hepatitis b virus antigens
EP2865671B1 (en) * 2012-06-22 2017-11-01 Sumitomo Chemical Company, Ltd Fused heterocyclic compound
CN103360398B (zh) * 2013-07-22 2015-03-25 山东大学 一种三唑并嘧啶类hiv-1逆转录酶抑制剂及其制备方法与应用
GB201504565D0 (en) 2015-03-18 2015-05-06 Takeda Pharmaceutical Novel compounds
KR101995533B1 (ko) * 2017-03-21 2019-07-02 한국화학연구원 [1,2,4]트리아졸로[4,3-a]퀴노잘린 아미노 페닐 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 포함하는 BET 단백질 관련 질환의 예방 또는 치료용 약학적 조성물
WO2022011171A1 (en) * 2020-07-08 2022-01-13 Klotho Therapeutics, Inc. Novel compounds and methods for increasing klotho gene expression
WO2020159942A1 (en) * 2019-01-29 2020-08-06 Tosk, Inc. Pyrazolopyrimidine modulators of ras gtpase
US12528796B2 (en) 2019-04-15 2026-01-20 Tosk, Inc. Modulators of RAS GTPase
WO2021211408A1 (en) * 2020-04-14 2021-10-21 The Trustees Of The University Of Pennsylvania Substituted {1,2,4,} triazolo{1,5-a} pyrimidine compounds and use in stabilizing microtubules
JP7564888B2 (ja) 2020-05-01 2024-10-09 ギリアード サイエンシーズ， インコーポレイテッド Ｃｄ７３阻害性２，４－ジオキソピリミジン化合物
US12180220B2 (en) 2020-10-14 2024-12-31 Tosk, Inc. Heteroaryl modulators of RAS GTPase
EP4422756A1 (en) 2021-10-29 2024-09-04 Gilead Sciences, Inc. Cd73 compounds
CN118475581A (zh) * 2022-01-25 2024-08-09 瑞石生物医药有限公司 一种ccr4小分子拮抗剂及其用途

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD55956A (https=) *
US4444774A (en) * 1982-07-29 1984-04-24 American Cyanamid Company 7-Heteroaryl[1,2,4]triazolo[1,5-a]pyrimidines

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE55956C (de) CH. GROOMBRIDGE und W. A. SOUTH in London, 40 New Bond Street Bremskurbel für Pferdebahn- und andere Wagen
DE61269C (de) 1891-04-01 1892-03-23 J. NEWBURG in Berlin O., Am Schlesischen Bahnhof Nr. 5 Waschmaschine
JPS5827773B2 (ja) * 1980-02-08 1983-06-11 持田製薬株式会社 癌転移抑制剤
GB8719368D0 (en) * 1987-08-15 1987-09-23 Wellcome Found Heterocyclic compounds
JPH02212488A (ja) * 1989-02-13 1990-08-23 Shinichiro Shimizu トリアゾールピリミジン誘導体
US5593996A (en) * 1991-12-30 1997-01-14 American Cyanamid Company Triazolopyrimidine derivatives
US5387747A (en) * 1992-02-24 1995-02-07 Laboratoires Upsa Triazolopyrimidine derivatives which are angiotensin II receptor antagonists, their methods of preparation and pharmaceutical compositions in which they are present
IL108747A (en) * 1993-03-04 1999-03-12 Shell Int Research Mushroom-killing preparations containing a history of 6 metamorphoses of 5 - 7 Dihalo - 1, 2 - 4 Triazlo [A-1,5] Pyrimidine Certain such new compounds and their preparation
GB9321162D0 (en) * 1993-10-13 1993-12-01 Boots Co Plc Therapeutic agents
US5869486A (en) * 1995-02-24 1999-02-09 Ono Pharmaceutical Co., Ltd. Fused pyrimidines and pyriazines as pharmaceutical compounds
US5948783A (en) * 1997-04-14 1999-09-07 American Cyanamid Company Fungicidal trifluoromethylalkylamino-triazolopyrimidines
US6117876A (en) * 1997-04-14 2000-09-12 American Cyanamid Company Fungicidal trifluorophenyl-triazolopyrimidines
US6255309B1 (en) * 1999-03-19 2001-07-03 American Cyanomid Co. Fungicidal trifluoromethylalkylamino-triazolopyrimidines
US5994360A (en) * 1997-07-14 1999-11-30 American Cyanamid Company Fungicidal 5-alkyl-triazolopyrimidines
US6020338A (en) * 1998-02-11 2000-02-01 American Cyanamid Company Fungicidal 7-alkyl-triazolopyrimidines
US6165940A (en) * 1998-09-25 2000-12-26 American Cyanamid Co. Non-aqueous suspension concentrate
FR2784380B1 (fr) * 1998-09-25 2002-09-06 American Cyanamid Co Triazolopyrimidines 7-oxy- et 7-thio-substituees fongicides
US6380202B1 (en) * 1998-09-25 2002-04-30 Basf Aktiengesellschaft Fungicidal fluoro-substituted 7-heterocyclyl-triazolopyrimidines
MY125533A (en) * 1999-12-06 2006-08-30 Bristol Myers Squibb Co Heterocyclic dihydropyrimidine compounds
JP2001322933A (ja) * 2000-05-15 2001-11-20 Ucb Sa Ｃｄ４０シグナル遮断剤
DE10121102A1 (de) * 2001-04-27 2002-11-07 Bayer Ag Triazolopyrimidine
DE10121101A1 (de) * 2001-04-27 2002-10-31 Bayer Ag Triazolopyrimidine
DE10121162A1 (de) * 2001-04-30 2002-10-31 Bayer Ag Triazolopyrimidine
US7037902B2 (en) * 2002-07-03 2006-05-02 Receptron, Inc. Affinity small molecules for the EPO receptor
SI1680425T1 (sl) * 2003-09-24 2007-04-30 Wyeth Corp 6-((substituirani)fenil)triazolopirimidini kot sredstva proti raku
US7419982B2 (en) * 2003-09-24 2008-09-02 Wyeth Holdings Corporation Crystalline forms of 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine salts

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD55956A (https=) *
US4444774A (en) * 1982-07-29 1984-04-24 American Cyanamid Company 7-Heteroaryl[1,2,4]triazolo[1,5-a]pyrimidines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2002257757B2 (en) * 2001-04-11 2008-05-08 Basf Aktiengesellschaft 5-Halogen-6-phenyl-7-fluoralkylamino-triazolopyrimidines as fungicides

Also Published As

Publication number Publication date
SK18412002A3 (sk) 2003-06-03
BR0112038A (pt) 2003-04-01
JP2004502691A (ja) 2004-01-29
EA006483B1 (ru) 2005-12-29
EP1307200A2 (en) 2003-05-07
PL360027A1 (en) 2004-09-06
CZ20024150A3 (cs) 2003-09-17
NO20026195D0 (no) 2002-12-23
IL152869A0 (en) 2003-06-24
MXPA02011913A (es) 2003-04-22
NO20026195L (no) 2003-02-27
CN1592624A (zh) 2005-03-09
ZA200300793B (en) 2004-07-20
EA200300091A1 (ru) 2003-08-28
KR20030013475A (ko) 2003-02-14
HUP0300798A3 (en) 2006-02-28
HK1052646A1 (zh) 2003-09-26
US7329663B2 (en) 2008-02-12
WO2002002563A2 (en) 2002-01-10
IN2003KO00001A (https=) 2005-12-02
HUP0300798A2 (hu) 2003-07-28
NZ523807A (en) 2004-09-24
WO2002002563A3 (en) 2003-01-03
US20020068744A1 (en) 2002-06-06
CA2413802A1 (en) 2002-01-10
AR034553A1 (es) 2004-03-03
BG107277A (bg) 2004-01-30
GEP20053688B (en) 2005-12-12
AU7306201A (en) 2002-01-14

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