ZA200301510B - Quinazoline derivatives as kinase inhibitors. - Google Patents

Quinazoline derivatives as kinase inhibitors. Download PDF

Info

Publication number: ZA200301510B
Authority: ZA; South Africa
Prior art keywords: methoxy; quinazolin; piperazinyl; carboxamide; amended sheet
Prior art date: 2000-08-18

Application number

ZA200301510A

Other languages

English (en)

Inventor

Anjali Pandey

Robert M Scarborough

Kenji Matsuno

Michio Ichimura

Yuji Nomoto

Shinichi Ide

Eiji Tsukuda

Junko Irie

Shoji Oda

Original Assignee

Millennium Pharm Inc

Kyowa Hakko Kogyo Kk

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.)

2000-08-18

Filing date

2003-02-26

Publication date

2004-06-22

2003-02-26 Application filed by Millennium Pharm Inc, Kyowa Hakko Kogyo Kk filed Critical Millennium Pharm Inc

2004-06-22 Publication of ZA200301510B publication Critical patent/ZA200301510B/en

Links

229940043355 kinase inhibitor Drugs 0.000 title description 2
239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
-1 nitrogen-containing heterocyclic compound Chemical class 0.000 claims description 39
150000003839 salts Chemical class 0.000 claims description 39
150000001875 compounds Chemical class 0.000 claims description 30
238000000034 method Methods 0.000 claims description 23
125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 14
125000004193 piperazinyl group Chemical group 0.000 claims description 13
201000010099 disease Diseases 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
230000002401 inhibitory effect Effects 0.000 claims description 12
150000004677 hydrates Chemical class 0.000 claims description 10
229940002612 prodrug Drugs 0.000 claims description 10
239000000651 prodrug Substances 0.000 claims description 10
239000012453 solvate Substances 0.000 claims description 10
230000026731 phosphorylation Effects 0.000 claims description 8
238000006366 phosphorylation reaction Methods 0.000 claims description 8
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
206010003210 Arteriosclerosis Diseases 0.000 claims description 6
206010028980 Neoplasm Diseases 0.000 claims description 6
108091008606 PDGF receptors Proteins 0.000 claims description 6
102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 claims description 6
208000011775 arteriosclerosis disease Diseases 0.000 claims description 6
201000011510 cancer Diseases 0.000 claims description 6
206010061989 glomerulosclerosis Diseases 0.000 claims description 6
230000002792 vascular Effects 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
230000002159 abnormal effect Effects 0.000 claims description 4
230000010261 cell growth Effects 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
230000002265 prevention Effects 0.000 claims description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
239000005711 Benzoic acid Substances 0.000 claims description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims description 2
WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 claims description 2
235000010233 benzoic acid Nutrition 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000000126 substance Substances 0.000 claims 9
125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 5
208000037803 restenosis Diseases 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 2
YNQJCOMRDQJVNA-UHFFFAOYSA-N 4-[6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yl]-n-(4-naphthalen-2-yloxyphenyl)piperazine-1-carboxamide Chemical compound C1=CC=CC2=CC(OC3=CC=C(C=C3)NC(=O)N3CCN(CC3)C=3N=CN=C4C=C(C(=CC4=3)OC)OCCOC)=CC=C21 YNQJCOMRDQJVNA-UHFFFAOYSA-N 0.000 claims 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
AJYMYKJMGGNMHX-UHFFFAOYSA-N n-(4-cyanophenyl)-4-[6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yl]piperazine-1-carboxamide Chemical compound C=12C=C(OC)C(OCCOC)=CC2=NC=NC=1N(CC1)CCN1C(=O)NC1=CC=C(C#N)C=C1 AJYMYKJMGGNMHX-UHFFFAOYSA-N 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
150000003857 carboxamides Chemical class 0.000 description 16
108091000080 Phosphotransferase Proteins 0.000 description 9
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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 3
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230000000694 effects Effects 0.000 description 3
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229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Chemical class 0.000 description 3
ZQFCWMFRQFAQPO-UHFFFAOYSA-N n-(4-propan-2-yloxyphenyl)formamide Chemical compound CC(C)OC1=CC=C(NC=O)C=C1 ZQFCWMFRQFAQPO-UHFFFAOYSA-N 0.000 description 3
230000008569 process Effects 0.000 description 3
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229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 2
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239000003112 inhibitor Substances 0.000 description 2
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XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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QJNRQJGEIYYPRW-UHFFFAOYSA-N 2,3-dimethoxyquinoline Chemical class C1=CC=C2N=C(OC)C(OC)=CC2=C1 QJNRQJGEIYYPRW-UHFFFAOYSA-N 0.000 description 1
RVZMPNMUBCAPQO-UHFFFAOYSA-N 2,4-dimethoxyquinazoline Chemical class C1=CC=CC2=NC(OC)=NC(OC)=C21 RVZMPNMUBCAPQO-UHFFFAOYSA-N 0.000 description 1
MYVWRUJLVWFNKC-UHFFFAOYSA-N 4-(6,7-dimethoxyquinazolin-4-yl)-n,n-dimethylpiperazine-1-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N1CCN(C(=O)N(C)C)CC1 MYVWRUJLVWFNKC-UHFFFAOYSA-N 0.000 description 1
MPDJGCLHGADASW-UHFFFAOYSA-N 4-(6-methoxy-7-prop-2-enoxyquinazolin-4-yl)-n-(4-phenoxyphenyl)piperazine-1-carboxamide Chemical compound N1=CN=C2C=C(OCC=C)C(OC)=CC2=C1N(CC1)CCN1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 MPDJGCLHGADASW-UHFFFAOYSA-N 0.000 description 1
YDVWNTXBGIEREW-UHFFFAOYSA-N 4-(7-ethoxy-6-methoxyquinazolin-4-yl)-n-(4-phenoxyphenyl)piperazine-1-carboxamide Chemical compound C=12C=C(OC)C(OCC)=CC2=NC=NC=1N(CC1)CCN1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 YDVWNTXBGIEREW-UHFFFAOYSA-N 0.000 description 1
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
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239000004471 Glycine Substances 0.000 description 1
101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
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COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
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102000001291 MAP Kinase Kinase Kinase Human genes 0.000 description 1
108091054455 MAP kinase family Proteins 0.000 description 1
102000043136 MAP kinase family Human genes 0.000 description 1
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241000124008 Mammalia Species 0.000 description 1
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229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
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125000004414 alkyl thio group Chemical group 0.000 description 1
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IIHNRXKTMNLPSH-UHFFFAOYSA-N n-[4-(1h-indol-4-yloxy)phenyl]-4-[6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yl]piperazine-1-carboxamide Chemical compound C=12C=C(OC)C(OCCOC)=CC2=NC=NC=1N(CC1)CCN1C(=O)NC(C=C1)=CC=C1OC1=CC=CC2=C1C=CN2 IIHNRXKTMNLPSH-UHFFFAOYSA-N 0.000 description 1
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COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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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
- C07D401/14—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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
- 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
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- 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
- 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
- A61P9/02—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
- A61P9/08—Vasodilators for multiple indications
- 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
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- 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
- C07D401/12—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 chain containing hetero atoms as chain links
- 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
- C07D403/12—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 chain containing hetero atoms as chain links

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Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
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ZA200301510A 2000-08-18 2003-02-26 Quinazoline derivatives as kinase inhibitors. ZA200301510B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US22612200P	2000-08-18	2000-08-18

Publications (1)

Publication Number	Publication Date
ZA200301510B true ZA200301510B (en)	2004-06-22

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Application Number	Title	Priority Date	Filing Date
ZA200301510A ZA200301510B (en)	2000-08-18	2003-02-26	Quinazoline derivatives as kinase inhibitors.

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US (5)	US6982266B2 (cs)
EP (3)	EP2277877A1 (cs)
JP (1)	JP5073147B2 (cs)
KR (1)	KR100831116B1 (cs)
CN (1)	CN100358890C (cs)
AT (1)	ATE402169T1 (cs)
AU (1)	AU8544901A (cs)
BR (1)	BR0113356A (cs)
CA (1)	CA2426440C (cs)
CY (1)	CY1110460T1 (cs)
CZ (1)	CZ304061B6 (cs)
DE (1)	DE60134990D1 (cs)
DK (1)	DK1315715T3 (cs)
EA (1)	EA005809B1 (cs)
ES (1)	ES2311023T3 (cs)
HU (1)	HU228668B1 (cs)
IL (2)	IL154514A0 (cs)
MX (1)	MXPA03001359A (cs)
NO (1)	NO323782B1 (cs)
NZ (1)	NZ524461A (cs)
PT (1)	PT1315715E (cs)
SI (1)	SI1315715T1 (cs)
WO (1)	WO2002016351A1 (cs)
ZA (1)	ZA200301510B (cs)

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2001
- 2001-08-17 PT PT01964612T patent/PT1315715E/pt unknown
- 2001-08-17 BR BR0113356-0A patent/BR0113356A/pt active Search and Examination
- 2001-08-17 EP EP10182322A patent/EP2277877A1/en not_active Withdrawn
- 2001-08-17 HU HU0302615A patent/HU228668B1/hu not_active IP Right Cessation
- 2001-08-17 EP EP01964612A patent/EP1315715B1/en not_active Expired - Lifetime
- 2001-08-17 WO PCT/US2001/041752 patent/WO2002016351A1/en not_active Ceased
- 2001-08-17 ES ES01964612T patent/ES2311023T3/es not_active Expired - Lifetime
- 2001-08-17 SI SI200130872T patent/SI1315715T1/sl unknown
- 2001-08-17 AT AT01964612T patent/ATE402169T1/de active
- 2001-08-17 NZ NZ52446101A patent/NZ524461A/xx not_active IP Right Cessation
- 2001-08-17 CA CA2426440A patent/CA2426440C/en not_active Expired - Fee Related
- 2001-08-17 DE DE60134990T patent/DE60134990D1/de not_active Expired - Lifetime
- 2001-08-17 DK DK01964612T patent/DK1315715T3/da active
- 2001-08-17 EA EA200300265A patent/EA005809B1/ru not_active IP Right Cessation
- 2001-08-17 AU AU8544901A patent/AU8544901A/xx active Pending
- 2001-08-17 IL IL15451401A patent/IL154514A0/xx active IP Right Grant
- 2001-08-17 EP EP08075237A patent/EP1964839A3/en not_active Ceased
- 2001-08-17 US US10/344,736 patent/US6982266B2/en not_active Expired - Fee Related
- 2001-08-17 CN CNB018173527A patent/CN100358890C/zh not_active Expired - Fee Related
- 2001-08-17 JP JP2002521452A patent/JP5073147B2/ja not_active Expired - Fee Related
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- 2001-08-17 CZ CZ20030765A patent/CZ304061B6/cs not_active IP Right Cessation
- 2001-08-17 KR KR1020037002381A patent/KR100831116B1/ko not_active Expired - Fee Related
2003
- 2003-02-17 NO NO20030747A patent/NO323782B1/no not_active IP Right Cessation
- 2003-02-18 IL IL154514A patent/IL154514A/en not_active IP Right Cessation
- 2003-02-26 ZA ZA200301510A patent/ZA200301510B/en unknown
2005
- 2005-08-22 US US11/210,028 patent/US7560461B2/en not_active Expired - Fee Related
2008
- 2008-10-21 CY CY20081101177T patent/CY1110460T1/el unknown
2009
- 2009-05-22 US US12/471,280 patent/US8324205B2/en not_active Expired - Fee Related
2012
- 2012-11-02 US US13/667,489 patent/US20130274252A1/en not_active Abandoned
2014
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Also Published As

Publication number	Publication date
WO2002016351A1 (en)	2002-02-28
US20050101609A1 (en)	2005-05-12
CZ2003765A3 (cs)	2004-08-18
EP1964839A3 (en)	2008-11-05
US7560461B2 (en)	2009-07-14
MXPA03001359A (es)	2004-12-13
US20130274252A1 (en)	2013-10-17
US20100113468A1 (en)	2010-05-06
DK1315715T3 (da)	2008-11-17
NO323782B1 (no)	2007-07-02
CZ304061B6 (cs)	2013-09-11
US20050288297A1 (en)	2005-12-29
HU228668B1 (hu)	2013-05-28
CN100358890C (zh)	2008-01-02
EA005809B1 (ru)	2005-06-30
AU8544901A (en)	2002-03-04
HK1057206A1 (en)	2004-03-19
US6982266B2 (en)	2006-01-03
IL154514A (en)	2011-03-31
HUP0302615A3 (en)	2008-03-28
US20150133439A1 (en)	2015-05-14
ES2311023T3 (es)	2009-02-01
DE60134990D1 (de)	2008-09-04
SI1315715T1 (sl)	2008-12-31
NO20030747L (no)	2003-04-14
AU2001285449B2 (en)	2007-04-05
IL154514A0 (en)	2003-09-17
CA2426440C (en)	2011-03-15
EA200300265A1 (ru)	2003-12-25
JP2005501796A (ja)	2005-01-20
EP1315715A1 (en)	2003-06-04
KR20030082537A (ko)	2003-10-22
KR100831116B1 (ko)	2008-05-20
JP5073147B2 (ja)	2012-11-14
BR0113356A (pt)	2004-04-20
EP2277877A1 (en)	2011-01-26
NO20030747D0 (no)	2003-02-17
EP1315715B1 (en)	2008-07-23
EP1964839A2 (en)	2008-09-03
NZ524461A (en)	2004-12-24
CN1633431A (zh)	2005-06-29
US8324205B2 (en)	2012-12-04
CA2426440A1 (en)	2002-02-28
HUP0302615A2 (hu)	2003-12-29
PT1315715E (pt)	2008-10-30
CY1110460T1 (el)	2015-04-29
ATE402169T1 (de)	2008-08-15

Publication	Publication Date	Title
ZA200301510B (en)	2004-06-22	Quinazoline derivatives as kinase inhibitors.
ZA200500322B (en)	2006-07-26	INdole of benzimidazole derivatives for modulating kB kinase
EP1309569B1 (en)	2010-10-06	N-aryl-{4-[7-(alkoxy)quinazolin-4-yl]piperazinyl}carboxamide derivatives as PDGFRs inhibitors
EP1309567A2 (en)	2003-05-14	Nitrogenous heterocyclic compounds
EP1309568B1 (en)	2011-02-16	[(quinazolin-4-yl)piperazin-4-yl]thiocarboxamide compounds as inhibitors of the phosphorylation of a PDGF receptor
AU2001285449B8 (en)	2007-05-03	Quinazoline derivatives as kinase inhibitors
AU2001285449A1 (en)	2002-05-30	Quinazoline derivatives as kinase inhibitors
HK1124316A (en)	2009-07-10	Quinazoline derivatives as kinase inhibitors
HK1057206B (en)	2008-12-24	Quinazoline derivatives as kinase inhibitors
KR20050073238A (ko)	2005-07-13	몰폴린기가 치환된 퀴나졸린 유도체