JP2001522802A - 大腸ポリープを治療するためのチロシンキナーゼインヒビターとしてのキナゾリン誘導体の使用 - Google Patents
大腸ポリープを治療するためのチロシンキナーゼインヒビターとしてのキナゾリン誘導体の使用Info
- Publication number
- JP2001522802A JP2001522802A JP2000520129A JP2000520129A JP2001522802A JP 2001522802 A JP2001522802 A JP 2001522802A JP 2000520129 A JP2000520129 A JP 2000520129A JP 2000520129 A JP2000520129 A JP 2000520129A JP 2001522802 A JP2001522802 A JP 2001522802A
- Authority
- JP
- Japan
- Prior art keywords
- amino
- bromophenyl
- quinazolinyl
- carbons
- alkyl
- 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.)
- Pending
Links
- 208000022131 polyp of large intestine Diseases 0.000 title 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 title 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 241000124008 Mammalia Species 0.000 claims abstract description 8
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
- 208000014081 polyp of colon Diseases 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- -1 nitro, carboxy Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
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- 238000004519 manufacturing process Methods 0.000 claims description 6
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- VWESXNFYLQAEJY-CMDGGOBGSA-N ethyl (e)-4-[[4-(3-bromoanilino)quinazolin-6-yl]amino]-4-oxobut-2-enoate Chemical compound C12=CC(NC(=O)/C=C/C(=O)OCC)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 VWESXNFYLQAEJY-CMDGGOBGSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
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- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- YBGIIBLAQDXGRC-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-2-methylprop-2-enamide Chemical compound C12=CC(NC(=O)C(=C)C)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 YBGIIBLAQDXGRC-UHFFFAOYSA-N 0.000 claims description 3
- AMDLDOZAZPADNX-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-3-phenylprop-2-ynamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C#CC=4C=CC=CC=4)=CC=C3N=CN=2)=C1 AMDLDOZAZPADNX-UHFFFAOYSA-N 0.000 claims description 3
- PEQADGPJYFGZLE-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]cyclopent-2-ene-1-carboxamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C4C=CCC4)=CC=C3N=CN=2)=C1 PEQADGPJYFGZLE-UHFFFAOYSA-N 0.000 claims description 3
- FDWGPDCUBAYMRY-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]hexa-2,4-dienamide Chemical compound C12=CC(NC(=O)C=CC=CC)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 FDWGPDCUBAYMRY-UHFFFAOYSA-N 0.000 claims description 3
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- 208000035984 Colonic Polyps Diseases 0.000 claims 3
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- 206010051589 Large intestine polyp Diseases 0.000 claims 2
- UUOXJUPRPMFYMJ-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-3-methylbut-2-enamide Chemical compound C12=CC(NC(=O)C=C(C)C)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 UUOXJUPRPMFYMJ-UHFFFAOYSA-N 0.000 claims 2
- 239000000243 solution Substances 0.000 description 36
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
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- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 5
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 5
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- 230000000694 effects Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- IZQHULBHKPGOAP-UHFFFAOYSA-N 4-n-(3-bromophenyl)quinazoline-4,6-diamine Chemical compound C12=CC(N)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 IZQHULBHKPGOAP-UHFFFAOYSA-N 0.000 description 4
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Classifications
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96508497A | 1997-11-06 | 1997-11-06 | |
| US08/965,084 | 1997-11-06 | ||
| PCT/US1998/023549 WO1999024037A1 (en) | 1997-11-06 | 1998-11-04 | Use of quinazoline derivatives as tyrosine kinase inhibitors for treating colonic polyps |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2001522802A true JP2001522802A (ja) | 2001-11-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000520129A Pending JP2001522802A (ja) | 1997-11-06 | 1998-11-04 | 大腸ポリープを治療するためのチロシンキナーゼインヒビターとしてのキナゾリン誘導体の使用 |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1039910A1 (ko) |
| JP (1) | JP2001522802A (ko) |
| KR (1) | KR20010031813A (ko) |
| CN (1) | CN1278176A (ko) |
| AR (1) | AR016415A1 (ko) |
| AU (1) | AU1308799A (ko) |
| BR (1) | BR9814116A (ko) |
| CA (1) | CA2306155A1 (ko) |
| HU (1) | HUP0004286A3 (ko) |
| IL (1) | IL135622A0 (ko) |
| NO (1) | NO20002166L (ko) |
| NZ (1) | NZ503991A (ko) |
| PL (1) | PL340800A1 (ko) |
| WO (1) | WO1999024037A1 (ko) |
| ZA (1) | ZA9810134B (ko) |
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| US6432979B1 (en) | 1999-08-12 | 2002-08-13 | American Cyanamid Company | Method of treating or inhibiting colonic polyps and colorectal cancer |
| EP1202746B1 (en) * | 1999-08-12 | 2006-10-04 | Wyeth Holdings Corporation | Nsaid and egfr kinase inhibitor containing composition for the treatment or inhibition of colonic polyps and colorectal cancer |
| US6924285B2 (en) | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| GB0309850D0 (en) | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| BRPI0410634A (pt) | 2003-05-30 | 2006-06-13 | Astrazeneca Uk Ltd | processo |
| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| SI1746999T1 (sl) | 2004-05-06 | 2012-01-31 | Warner Lambert Co | 4-fenilamino-kinazolin-6-il-amidi |
| DE602005026865D1 (de) | 2004-12-14 | 2011-04-21 | Astrazeneca Ab | Pyrazolopyrimidinverbindungen als antitumormittel |
| WO2006071079A1 (en) * | 2004-12-29 | 2006-07-06 | Hanmi Pharm. Co., Ltd. | Quinazoline derivatives for inhibiting cancer cell growth and method for the preparation thereof |
| ATE488513T1 (de) | 2005-09-20 | 2010-12-15 | Astrazeneca Ab | 4-(1h-indazol-5-ylamino)chinazolinverbindungen als inhibitoren der erbb-rezeptortyrosinkinase zur behandlung von krebs |
| EP2061906B1 (en) | 2006-09-12 | 2011-08-31 | Genentech, Inc. | Methods and compositions for the diagnosis and treatment of lung cancer using pdgfra, kit or kdr gene as genetic marker |
| EP1921070A1 (de) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
| EA200901041A1 (ru) | 2007-02-06 | 2010-02-26 | Бёрингер Ингельхайм Интернациональ Гмбх | Бициклические гетероциклы, содержащие эти соединения лекарственные средства, их применение и способ их получения |
| US20110104166A1 (en) * | 2008-01-18 | 2011-05-05 | Stankovic Konstantina M | Methods and Compositions for Treating Polyps |
| TWI472339B (zh) | 2008-01-30 | 2015-02-11 | Genentech Inc | 包含結合至ｈｅｒ２結構域ii之抗體及其酸性變異體的組合物 |
| BRPI0907916A2 (pt) | 2008-02-07 | 2015-07-28 | Boehringer Ingelheim Int | Heterociclos espirociclos, medicamentos contendo esses compostos, e processos para preparar os mesmos |
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- 1998-11-04 JP JP2000520129A patent/JP2001522802A/ja active Pending
- 1998-11-04 IL IL13562298A patent/IL135622A0/xx unknown
- 1998-11-04 BR BR9814116-3A patent/BR9814116A/pt not_active IP Right Cessation
- 1998-11-05 ZA ZA9810134A patent/ZA9810134B/xx unknown
- 1998-11-05 AR ARP980105592A patent/AR016415A1/es unknown
-
2000
- 2000-04-27 NO NO20002166A patent/NO20002166L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999024037A1 (en) | 1999-05-20 |
| CN1278176A (zh) | 2000-12-27 |
| NO20002166L (no) | 2000-06-28 |
| CA2306155A1 (en) | 1999-05-20 |
| AU1308799A (en) | 1999-05-31 |
| AR016415A1 (es) | 2001-07-04 |
| HUP0004286A3 (en) | 2002-01-28 |
| NZ503991A (en) | 2001-11-30 |
| HUP0004286A2 (hu) | 2001-11-28 |
| PL340800A1 (en) | 2001-02-26 |
| IL135622A0 (en) | 2001-05-20 |
| NO20002166D0 (no) | 2000-04-27 |
| BR9814116A (pt) | 2000-10-03 |
| KR20010031813A (ko) | 2001-04-16 |
| ZA9810134B (en) | 2000-05-05 |
| EP1039910A1 (en) | 2000-10-04 |
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