OA11833A - Heteroaryl-substituted quinolin-2-one derivatives useful as anticancer agents. - Google Patents

Heteroaryl-substituted quinolin-2-one derivatives useful as anticancer agents. Download PDF

Info

Publication number: OA11833A
Authority: OA; OAPI
Prior art keywords: methyl; chloro; phenyl; cr13r14; formula
Prior art date: 1999-02-11

Application number

OA1200100212A

Other languages

English (en)

Inventor

Bingwei Vera Yang

Original Assignee

Pfizer Prod Inc

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.)

1999-02-11

Filing date

2000-02-04

Publication date

2005-08-23

2000-02-04 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2005-08-23 Publication of OA11833A publication Critical patent/OA11833A/en

Links

LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title description 18
239000002246 antineoplastic agent Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 317
238000000034 method Methods 0.000 claims abstract description 113
230000002159 abnormal effect Effects 0.000 claims abstract description 23
241000124008 Mammalia Species 0.000 claims abstract description 22
230000010261 cell growth Effects 0.000 claims abstract description 19
230000002194 synthesizing effect Effects 0.000 claims abstract description 9
-1 hydroxy, amino Chemical group 0.000 claims description 128
125000003118 aryl group Chemical group 0.000 claims description 109
125000001424 substituent group Chemical group 0.000 claims description 78
125000004093 cyano group Chemical group *C#N 0.000 claims description 67
125000000217 alkyl group Chemical group 0.000 claims description 61
229910052739 hydrogen Inorganic materials 0.000 claims description 51
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 50
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 50
229910052799 carbon Inorganic materials 0.000 claims description 47
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 38
239000000203 mixture Substances 0.000 claims description 38
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 37
125000004122 cyclic group Chemical group 0.000 claims description 29
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
239000002904 solvent Substances 0.000 claims description 26
125000003342 alkenyl group Chemical group 0.000 claims description 24
239000003112 inhibitor Substances 0.000 claims description 22
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 17
239000003795 chemical substances by application Substances 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
239000003153 chemical reaction reagent Substances 0.000 claims description 15
101100460702 Aspergillus sp. (strain MF297-2) notH gene Proteins 0.000 claims description 13
229920006395 saturated elastomer Polymers 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
238000001959 radiotherapy Methods 0.000 claims description 5
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 3
230000001235 sensitizing effect Effects 0.000 claims description 3
230000000903 blocking effect Effects 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
230000019491 signal transduction Effects 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 14
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
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101710151806 72 kDa type IV collagenase Proteins 0.000 claims 1
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239000000543 intermediate Substances 0.000 abstract description 47
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230000002401 inhibitory effect Effects 0.000 abstract description 20
150000003839 salts Chemical class 0.000 abstract description 16
239000008194 pharmaceutical composition Substances 0.000 abstract description 8
239000012453 solvate Substances 0.000 abstract 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 92
125000000623 heterocyclic group Chemical group 0.000 description 86
239000007787 solid Substances 0.000 description 70
125000005843 halogen group Chemical group 0.000 description 51
239000000243 solution Substances 0.000 description 48
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
125000000753 cycloalkyl group Chemical group 0.000 description 36
239000011541 reaction mixture Substances 0.000 description 27
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229910052943 magnesium sulfate Inorganic materials 0.000 description 23
235000019341 magnesium sulphate Nutrition 0.000 description 23
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
230000000694 effects Effects 0.000 description 12
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
125000002883 imidazolyl group Chemical group 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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108010014186 ras Proteins Proteins 0.000 description 9
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230000012010 growth Effects 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 6
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102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 6
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230000000973 chemotherapeutic effect Effects 0.000 description 6
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FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
VVFIVMKKDHRTTO-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-[(6-chloropyridin-3-yl)-hydroxy-(3-methylimidazol-4-yl)methyl]-1h-quinolin-2-one Chemical compound CN1C=NC=C1C(O)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)NC2=CC=1)C1=CC=C(Cl)N=C1 VVFIVMKKDHRTTO-UHFFFAOYSA-N 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
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Classifications

- 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
- A—HUMAN NECESSITIES
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- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- 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
- 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
- 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

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
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Communicable Diseases (AREA)
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Vascular Medicine (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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OA1200100212A 1999-02-11 2000-02-04 Heteroaryl-substituted quinolin-2-one derivatives useful as anticancer agents. OA11833A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US11970299P	1999-02-11	1999-02-11

Publications (1)

Publication Number	Publication Date
OA11833A true OA11833A (en)	2005-08-23

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OA1200100212A OA11833A (en)	1999-02-11	2000-02-04	Heteroaryl-substituted quinolin-2-one derivatives useful as anticancer agents.

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US (3)	US6258824B1 (id)
EP (1)	EP1150973B1 (id)
JP (3)	JP4090200B2 (id)
KR (1)	KR20010102073A (id)
CN (1)	CN1340051A (id)
AP (1)	AP2001002241A0 (id)
AR (1)	AR028985A1 (id)
AT (1)	ATE297916T1 (id)
AU (1)	AU2124800A (id)
BG (1)	BG105860A (id)
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CA (1)	CA2362394C (id)
CO (1)	CO5140097A1 (id)
CZ (1)	CZ20012910A3 (id)
DE (1)	DE60020812T2 (id)
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EA (1)	EA200100766A1 (id)
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HR (1)	HRP20010574A2 (id)
HU (1)	HUP0105231A3 (id)
ID (1)	ID29584A (id)
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IS (1)	IS5997A (id)
MA (1)	MA26718A1 (id)
NO (1)	NO20013909L (id)
OA (1)	OA11833A (id)
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SK (1)	SK11002001A3 (id)
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TR (2)	TR200201297T2 (id)
WO (1)	WO2000047574A1 (id)
ZA (1)	ZA200106520B (id)

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HN2000000019A (es)	2001-07-30
IL144307A0 (en)	2002-05-23
DE60020812T2 (de)	2006-05-04
HUP0105231A3 (en)	2003-01-28
WO2000047574A1 (en)	2000-08-17
HK1042096A1 (zh)	2002-08-02
SK11002001A3 (sk)	2002-05-09
EA200100766A1 (ru)	2002-02-28
JP2005002124A (ja)	2005-01-06
US6258824B1 (en)	2001-07-10
US20020120145A1 (en)	2002-08-29
PA8490601A1 (es)	2002-07-30
US6710209B2 (en)	2004-03-23
US6388092B2 (en)	2002-05-14
EP1150973A1 (en)	2001-11-07
CN1340051A (zh)	2002-03-13
CZ20012910A3 (cs)	2002-02-13
BG105860A (en)	2002-03-29
AR028985A1 (es)	2003-06-04
CA2362394A1 (en)	2000-08-17
EE200100425A (et)	2002-12-16
TR200201297T2 (tr)	2002-06-21
IS5997A (is)	2001-07-10
ES2243228T3 (es)	2005-12-01
JP2004182741A (ja)	2004-07-02
JP2002536444A (ja)	2002-10-29
DE60020812D1 (de)	2005-07-21
ID29584A (id)	2001-09-06
ATE297916T1 (de)	2005-07-15
CA2362394C (en)	2006-01-17
ZA200106520B (en)	2002-08-26
AU2124800A (en)	2000-08-29
HUP0105231A2 (hu)	2002-04-29
JP4216740B2 (ja)	2009-01-28
NO20013909L (no)	2001-10-08
PL349839A1 (en)	2002-09-23
NO20013909D0 (no)	2001-08-10
HRP20010574A2 (en)	2002-12-31
US20020019530A1 (en)	2002-02-14
BR0008202A (pt)	2002-02-19
AP2001002241A0 (en)	2001-09-30
JP4090200B2 (ja)	2008-05-28
TR200201296T2 (tr)	2002-07-22
PE20001464A1 (es)	2000-12-20
TNSN00028A1 (fr)	2005-11-10
MA26718A1 (fr)	2004-12-20
SV2001000020A (es)	2001-11-08
EP1150973B1 (en)	2005-06-15
KR20010102073A (ko)	2001-11-15
CO5140097A1 (es)	2002-03-22
GT200000014A (es)	2001-08-03
DZ3009A1 (fr)	2004-03-27

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