UA81470C2 - Fused heterocycles and uses thereof - Google Patents

Fused heterocycles and uses thereof Download PDF

Info

Publication number: UA81470C2
Authority: UA; Ukraine
Prior art keywords: optionally substituted; methyl; oxo; benzyl; propyl
Prior art date: 2003-03-07

Application number

UAA200509430A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Astrazeneca Ab

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.)

2003-03-07

Filing date

2004-04-03

Publication date

2008-01-10

2003-03-07 Priority claimed from SE0300627A external-priority patent/SE0300627D0/xx

2003-04-15 Priority claimed from SE0301138A external-priority patent/SE0301138D0/xx

2003-06-10 Priority claimed from SE0301697A external-priority patent/SE0301697D0/xx

2003-10-24 Priority claimed from SE0302826A external-priority patent/SE0302826D0/xx

2004-04-03 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2008-01-10 Publication of UA81470C2 publication Critical patent/UA81470C2/uk

Links

125000000623 heterocyclic group Chemical group 0.000 title claims description 48
238000000034 method Methods 0.000 claims abstract description 160
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238000011282 treatment Methods 0.000 claims abstract description 30
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239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
238000011321 prophylaxis Methods 0.000 claims abstract description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 80
150000003839 salts Chemical class 0.000 claims description 57
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 39
125000001424 substituent group Chemical group 0.000 claims description 37
125000003118 aryl group Chemical group 0.000 claims description 23
125000000547 substituted alkyl group Chemical group 0.000 claims description 22
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
UHBGYFCCKRAEHA-UHFFFAOYSA-N P-toluamide Chemical compound CC1=CC=C(C(N)=O)C=C1 UHBGYFCCKRAEHA-UHFFFAOYSA-N 0.000 claims description 17
125000003107 substituted aryl group Chemical group 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 15
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
125000005017 substituted alkenyl group Chemical group 0.000 claims description 10
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 7
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
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Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Epidemiology (AREA)
Dermatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Transplantation (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Ophthalmology & Optometry (AREA)
Oncology (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)

UAA200509430A 2003-03-07 2004-04-03 Fused heterocycles and uses thereof UA81470C2 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
SE0300627A SE0300627D0 (sv)	2003-03-07	2003-03-07	Novel fused heterocycles and uses therof
SE0301138A SE0301138D0 (sv)	2003-04-15	2003-04-15	Novel fused heterocycles and uses thereof
SE0301697A SE0301697D0 (sv)	2003-06-10	2003-06-10	Novel fused heterocycles and uses thereof
SE0302826A SE0302826D0 (sv)	2003-10-24	2003-10-24	Novel fused heterocycles and uses thereof
PCT/SE2004/000304 WO2004078758A1 (en)	2003-03-07	2004-03-04	Novel fused heterocycles and uses thereof

Publications (1)

Publication Number	Publication Date
UA81470C2 true UA81470C2 (en)	2008-01-10

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ID=32966643

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200509430A UA81470C2 (en)	2003-03-07	2004-04-03	Fused heterocycles and uses thereof

Country Status (24)

Country	Link
US (1)	US20060270689A1 (no)
EP (1)	EP1601673B1 (no)
JP (2)	JP3947758B2 (no)
KR (1)	KR20050107784A (no)
AR (1)	AR043487A1 (no)
AT (1)	ATE433448T1 (no)
AU (1)	AU2004218080B2 (no)
BR (1)	BRPI0408150A (no)
CA (1)	CA2518224C (no)
CY (1)	CY1109300T1 (no)
DE (1)	DE602004021477D1 (no)
DK (1)	DK1601673T3 (no)
ES (1)	ES2326647T3 (no)
IS (1)	IS8036A (no)
MX (1)	MXPA05009577A (no)
MY (1)	MY141583A (no)
NO (1)	NO20054340L (no)
NZ (1)	NZ542227A (no)
PL (1)	PL1601673T3 (no)
PT (1)	PT1601673E (no)
SI (1)	SI1601673T1 (no)
TW (1)	TW200510427A (no)
UA (1)	UA81470C2 (no)
WO (1)	WO2004078758A1 (no)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7230000B1 (en)	1999-10-27	2007-06-12	Cytokinetics, Incorporated	Methods and compositions utilizing quinazolinones
US6545004B1 (en)	1999-10-27	2003-04-08	Cytokinetics, Inc.	Methods and compositions utilizing quinazolinones
CA2475879A1 (en)	2002-02-15	2003-08-28	Cytokinetics, Inc.	Synthesis of quinazolinones
NZ537076A (en)	2002-05-09	2007-06-29	Cytokinetics Inc	Pyrimidinone compounds, compositions and methods
JP2005530785A (ja)	2002-05-09	2005-10-13	サイトキネティクス・インコーポレーテッド	化合物、組成物、及び方法
AU2003265242A1 (en)	2002-05-23	2003-12-22	Cytokinetics, Inc.	Compounds, compositions, and methods
AU2003236527A1 (en)	2002-06-14	2003-12-31	Cytokinetics, Inc.	Compounds, compositions, and methods
EP1537089A4 (en)	2002-07-23	2008-04-16	Cytokinetics Inc	CONNECTIONS, COMPOSITIONS AND PROCEDURES
AU2003277079A1 (en)	2002-09-30	2004-05-04	Cytokinetics, Inc.	Compounds, compositions, and methods
AR050920A1 (es) *	2003-03-07	2006-12-06	Astrazeneca Ab	Enantiomeros de heterociclos fusionados seleccionados y usos de los mismos
US7550590B2 (en) *	2003-03-25	2009-06-23	Takeda Pharmaceutical Company Limited	Dipeptidyl peptidase inhibitors
US7022850B2 (en)	2003-05-22	2006-04-04	Bristol-Myers Squibb Co.	Bicyclicpyrimidones and their use to treat diseases
WO2005061460A1 (en)	2003-12-08	2005-07-07	Cytokinetics, Inc.	Compounds, compositions, and methods
MX2007001953A (es) *	2004-08-18	2007-05-09	Astrazeneca Ab	Enantiomeros de pirimidonas fusionadas seleccionadas y usos en el tratamiento y prevencion del cancer.
CA2575056A1 (en) *	2004-08-18	2006-02-23	Astrazeneca Ab	Selected fused heterocyclics and uses thereof
WO2006078574A2 (en) *	2005-01-19	2006-07-27	Merck & Co., Inc.	Mitotic kinesin inhibitors
DE102005011822A1 (de) *	2005-03-15	2006-09-21	Merck Patent Gmbh	Phthalazinone
DE102005027168A1 (de)	2005-06-13	2006-12-14	Merck Patent Gmbh	Tetrahydrochinoline
AU2008265600B2 (en) *	2007-06-21	2013-10-31	Neuronascent, Inc.	Methods and compositions for stimulating neurogenesis and inhibiting neuronal degeneration using isothiazolopyrimidinones
WO2009001214A2 (en) *	2007-06-28	2008-12-31	Pfizer Products Inc.	Thieno[2,3-d]pyrimidin-4(3h)-one, isoxazolo[5,4-d]pyrimidin-4(5h)-one and isothiazolo[5,4-d]pyrimidin-4(5h)-one derivatives as calcium receptor antagonists
CN114478429B (zh) *	2020-11-13	2023-11-17	中国科学院大连化学物理研究所	一种3-烷硫基异噻唑衍生物及其合成方法

Family Cites Families (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6545004B1 (en) *	1999-10-27	2003-04-08	Cytokinetics, Inc.	Methods and compositions utilizing quinazolinones
US7230000B1 (en) *	1999-10-27	2007-06-12	Cytokinetics, Incorporated	Methods and compositions utilizing quinazolinones
PL366311A1 (en) *	2000-12-11	2005-01-24	Tularik Inc.	Cxcr3 antagonists
US6809102B2 (en) *	2001-03-29	2004-10-26	Bristol-Myers Squibb Company	Cyano-substituted dihydropyrimidine compounds and their use to treat diseases
US7060705B2 (en) *	2001-11-07	2006-06-13	Merck & Co., Inc.	Mitotic kinesin inhibitors
AU2002346471A1 (en) *	2001-11-20	2003-06-10	Cytokinetics, Inc.	Process for the racemization of chiral quinazolinones
CA2467722A1 (en) *	2001-12-06	2003-06-19	Merck & Co., Inc.	Thienopyrimidinone derivatives as mitotic kinesin inhibitors
JP4464136B2 (ja) *	2001-12-06	2010-05-19	メルク・シャープ・エンド・ドーム・コーポレイション	有糸分裂キネシン阻害薬
WO2003050122A2 (en) *	2001-12-06	2003-06-19	Merck & Co., Inc.	Mitotic kinesin inhibitors
AU2002357043B2 (en) *	2001-12-06	2008-04-24	Merck Sharp & Dohme Corp.	Mitotic kinesin inhibitors
ATE447577T1 (de) *	2001-12-06	2009-11-15	Merck & Co Inc	Mitotische kinesin-hemmer
CN100381437C (zh) *	2002-04-17	2008-04-16	赛特凯恩蒂克公司	化合物、组合物和方法
JP2005530785A (ja) *	2002-05-09	2005-10-13	サイトキネティクス・インコーポレーテッド	化合物、組成物、及び方法
NZ537076A (en) *	2002-05-09	2007-06-29	Cytokinetics Inc	Pyrimidinone compounds, compositions and methods
AU2003265242A1 (en) *	2002-05-23	2003-12-22	Cytokinetics, Inc.	Compounds, compositions, and methods
JP2005533119A (ja) *	2002-07-17	2005-11-04	サイトキネティクス・インコーポレーテッド	化合物、組成物、及び方法
US7022850B2 (en) *	2003-05-22	2006-04-04	Bristol-Myers Squibb Co.	Bicyclicpyrimidones and their use to treat diseases
US7345046B2 (en) *	2003-05-30	2008-03-18	Chiron Corporation	Heteroaryl-fused pyrimidinyl compounds as anticancer agents
KR20060069356A (ko) *	2003-06-20	2006-06-21	카이론 코포레이션	항암제로서 피리디노[1,2-α]피리미딘-4-온 화합물
JP2007507539A (ja) *	2003-10-06	2007-03-29	サイトキネティクス・インコーポレーテッド	化合物、組成物及び方法
EP1680420A4 (en) *	2003-11-07	2008-09-24	Cytokinetics Inc	COMPOUNDS, COMPOSITIONS AND METHODS
US20050158320A1 (en) *	2003-11-12	2005-07-21	Nichols M. J.	Combinations for the treatment of proliferative diseases
US7501416B2 (en) *	2004-02-06	2009-03-10	Bristol-Myers Squibb Company	Quinoxaline compounds and methods of using them
DE602005012069D1 (de) *	2004-04-06	2009-02-12	Novartis Vaccines & Diagnostic	Inhibitoren von mitotischem kinesin
US7608723B2 (en) *	2004-10-19	2009-10-27	Novartis Vaccines And Diagnostics, Inc.	Indole and benzimidazole derivatives

2004
- 2004-03-04 KR KR1020057016722A patent/KR20050107784A/ko not_active Ceased
- 2004-03-04 DK DK04717339T patent/DK1601673T3/da active
- 2004-03-04 AT AT04717339T patent/ATE433448T1/de active
- 2004-03-04 PL PL04717339T patent/PL1601673T3/pl unknown
- 2004-03-04 CA CA2518224A patent/CA2518224C/en not_active Expired - Fee Related
- 2004-03-04 JP JP2006507939A patent/JP3947758B2/ja not_active Expired - Fee Related
- 2004-03-04 WO PCT/SE2004/000304 patent/WO2004078758A1/en not_active Ceased
- 2004-03-04 EP EP04717339A patent/EP1601673B1/en not_active Expired - Lifetime
- 2004-03-04 MX MXPA05009577A patent/MXPA05009577A/es active IP Right Grant
- 2004-03-04 NZ NZ542227A patent/NZ542227A/en not_active IP Right Cessation
- 2004-03-04 SI SI200431186T patent/SI1601673T1/sl unknown
- 2004-03-04 PT PT04717339T patent/PT1601673E/pt unknown
- 2004-03-04 AU AU2004218080A patent/AU2004218080B2/en not_active Ceased
- 2004-03-04 ES ES04717339T patent/ES2326647T3/es not_active Expired - Lifetime
- 2004-03-04 US US10/548,138 patent/US20060270689A1/en not_active Abandoned
- 2004-03-04 MY MYPI20040755A patent/MY141583A/en unknown
- 2004-03-04 DE DE602004021477T patent/DE602004021477D1/de not_active Expired - Lifetime
- 2004-03-04 BR BRPI0408150-1A patent/BRPI0408150A/pt not_active IP Right Cessation
- 2004-03-05 TW TW093105906A patent/TW200510427A/zh unknown
- 2004-03-05 AR ARP040100701A patent/AR043487A1/es not_active Application Discontinuation
- 2004-04-03 UA UAA200509430A patent/UA81470C2/uk unknown
2005
- 2005-09-19 IS IS8036A patent/IS8036A/is unknown
- 2005-09-20 NO NO20054340A patent/NO20054340L/no unknown
2006
- 2006-07-25 JP JP2006201461A patent/JP2007063257A/ja active Pending
2009
- 2009-08-10 CY CY20091100845T patent/CY1109300T1/el unknown

Also Published As

Publication number	Publication date
ES2326647T3 (es)	2009-10-16
BRPI0408150A (pt)	2006-03-21
SI1601673T1 (sl)	2009-10-31
AU2004218080A1 (en)	2004-09-16
CY1109300T1 (el)	2014-07-02
ATE433448T1 (de)	2009-06-15
JP2007063257A (ja)	2007-03-15
PT1601673E (pt)	2009-07-29
KR20050107784A (ko)	2005-11-15
DK1601673T3 (da)	2009-08-24
PL1601673T3 (pl)	2009-10-30
JP2006519853A (ja)	2006-08-31
EP1601673A1 (en)	2005-12-07
AU2004218080B2 (en)	2008-01-03
NO20054340L (no)	2005-09-26
AR043487A1 (es)	2005-08-03
TW200510427A (en)	2005-03-16
CA2518224C (en)	2010-06-15
NZ542227A (en)	2008-12-24
EP1601673B1 (en)	2009-06-10
MY141583A (en)	2010-05-14
HK1084390A1 (en)	2006-07-28
IS8036A (is)	2005-09-19
DE602004021477D1 (de)	2009-07-23
JP3947758B2 (ja)	2007-07-25
US20060270689A1 (en)	2006-11-30
CA2518224A1 (en)	2004-09-16
MXPA05009577A (es)	2005-12-12
WO2004078758A1 (en)	2004-09-16

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