CA2306155A1 - Traitement des polypes du colon par des inhibiteurs de la tyrosine kinase a base de derives de quinazoline - Google Patents
Traitement des polypes du colon par des inhibiteurs de la tyrosine kinase a base de derives de quinazoline Download PDFInfo
- Publication number
- CA2306155A1 CA2306155A1 CA002306155A CA2306155A CA2306155A1 CA 2306155 A1 CA2306155 A1 CA 2306155A1 CA 002306155 A CA002306155 A CA 002306155A CA 2306155 A CA2306155 A CA 2306155A CA 2306155 A1 CA2306155 A1 CA 2306155A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- carbon atoms
- bromophenyl
- quinazolinyl
- 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.)
- Abandoned
Links
- 208000035984 Colonic Polyps Diseases 0.000 title claims abstract description 11
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 2
- 239000005483 tyrosine kinase inhibitor Substances 0.000 title description 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- -1 carboalkoxy 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
- 238000000034 method Methods 0.000 claims abstract description 10
- 241000124008 Mammalia Species 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- BTYYWOYVBXILOJ-UHFFFAOYSA-N N-{4-[(3-bromophenyl)amino]quinazolin-6-yl}but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 BTYYWOYVBXILOJ-UHFFFAOYSA-N 0.000 claims description 6
- DZDCQTBAAQYSND-VOTSOKGWSA-N (e)-4-[[4-(3-bromoanilino)quinazolin-6-yl]amino]-4-oxobut-2-enoic acid Chemical compound C12=CC(NC(=O)/C=C/C(=O)O)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 DZDCQTBAAQYSND-VOTSOKGWSA-N 0.000 claims description 3
- JPHUTKJINPEEPQ-DUXPYHPUSA-N (e)-n-[4-(3-bromoanilino)quinazolin-6-yl]but-2-enamide Chemical compound C12=CC(NC(=O)/C=C/C)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 JPHUTKJINPEEPQ-DUXPYHPUSA-N 0.000 claims description 3
- DZDCQTBAAQYSND-SREVYHEPSA-N (z)-4-[[4-(3-bromoanilino)quinazolin-6-yl]amino]-4-oxobut-2-enoic acid Chemical compound C12=CC(NC(=O)\C=C/C(=O)O)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 DZDCQTBAAQYSND-SREVYHEPSA-N 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
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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 3
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- 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 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
- 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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- 239000003814 drug Substances 0.000 claims 1
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- XNERWVPQCYSMLC-UHFFFAOYSA-N phenylpropiolic acid Chemical compound OC(=O)C#CC1=CC=CC=C1 XNERWVPQCYSMLC-UHFFFAOYSA-N 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- XELRMPRLCPFTBH-UHFFFAOYSA-N quinazoline-2,4-diamine Chemical compound C1=CC=CC2=NC(N)=NC(N)=C21 XELRMPRLCPFTBH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical 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)
Abstract
La présente invention concerne le traitement ou la prévention des polypes du colon chez un mammifère. Ce traitement consiste en l'administration au mammifère justifiant d'un tel traitement d'un composé représenté par la formule générale (I). Dans cette formule générale, X est phényle éventuellement substitué. R et R¿1? sont chacun indépendamment hydrogène, halogène, alkyle, alcoxy, hydroxy ou trifluorométhyle. R¿2? est hydrogène, alkyle, alcoxy, hydroxy ou trifluorométhyle. Y est un radical tel que représenté par les formules spécifiques (II), (III), (IV), (V), (VI), (VII) ou (VIII). R¿3? est indépendamment hydrogène, alkyle, carboxy, carboalcoxy, phényle, ou carboalkyle. Le "n" vaut 2 à 4. L'invention concerne également certains des sels de ces composés sous la réserve que chaque R¿3? de Y peut être identique ou différent.
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 (fr) | 1997-11-06 | 1998-11-04 | Traitement des polypes du colon par des inhibiteurs de la tyrosine kinase a base de derives de quinazoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2306155A1 true CA2306155A1 (fr) | 1999-05-20 |
Family
ID=25509419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002306155A Abandoned CA2306155A1 (fr) | 1997-11-06 | 1998-11-04 | Traitement des polypes du colon par des inhibiteurs de la tyrosine kinase a base de derives de quinazoline |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1039910A1 (fr) |
| JP (1) | JP2001522802A (fr) |
| KR (1) | KR20010031813A (fr) |
| CN (1) | CN1278176A (fr) |
| AR (1) | AR016415A1 (fr) |
| AU (1) | AU1308799A (fr) |
| BR (1) | BR9814116A (fr) |
| CA (1) | CA2306155A1 (fr) |
| HU (1) | HUP0004286A3 (fr) |
| IL (1) | IL135622A0 (fr) |
| NO (1) | NO20002166L (fr) |
| NZ (1) | NZ503991A (fr) |
| PL (1) | PL340800A1 (fr) |
| WO (1) | WO1999024037A1 (fr) |
| ZA (1) | ZA9810134B (fr) |
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|---|---|---|---|---|
| NZ517120A (en) * | 1999-08-12 | 2004-10-29 | Wyeth Corp | NSAID and EFGR kinase inhibitor containing composition for the treatment or inhibition of colonic polyps and colorectal cancer |
| US6432979B1 (en) | 1999-08-12 | 2002-08-13 | American Cyanamid Company | Method of treating or inhibiting 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 |
| WO2005049829A1 (fr) | 2003-05-30 | 2005-06-02 | Astrazeneca Uk Limited | Procede |
| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| KR100885835B1 (ko) | 2004-05-06 | 2009-02-26 | 워너-램버트 캄파니 엘엘씨 | 4-페닐아미노-퀴나졸린-6-일-아미드 |
| DE602005026865D1 (de) | 2004-12-14 | 2011-04-21 | Astrazeneca Ab | Pyrazolopyrimidinverbindungen als antitumormittel |
| WO2006071079A1 (fr) * | 2004-12-29 | 2006-07-06 | Hanmi Pharm. Co., Ltd. | Dérivés de quinazoline employés dans l'inhibition de la croissance des cellules cancéreuses et méthodes de synthèse desdits dérivés |
| DE602006018331D1 (de) | 2005-09-20 | 2010-12-30 | Astrazeneca Ab | 4-(1h-indazol-5-ylamino)chinazolinverbindungen als inhibitoren der erbb-rezeptortyrosinkinase zur behandlung von krebs |
| WO2008033782A2 (fr) | 2006-09-12 | 2008-03-20 | Genentech, Inc. | Procédés et compositions pour le diagnostic et le traitement du cancer |
| EP1921070A1 (fr) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | heterocycles bicycliques, medicaments á base de ces composes, leur usage et procédé pour leur preparation |
| BRPI0807234A2 (pt) | 2007-02-06 | 2014-06-03 | Boehringer Ingelheim Int | Heterociclos bicíclicos, composições farmacêuticas que contêm estes compostos, o uso dos mesmos e processos para a preparação dos mesmos |
| 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 |
| DK2245026T3 (da) | 2008-02-07 | 2012-10-15 | Boehringer Ingelheim Int | Spirocycliske heterocycler, lægemiddel indeholdende disse forbindelser, deres anvendelse og fremgangsmåde til deres fremstilling |
| MY183041A (en) | 2008-05-13 | 2021-02-08 | Astrazeneca Ab | Fumarate salt of 4- (3-chloro-2-fluoroanilino) -7-methoxy-6- {[1- (n-methylcarbamoylmethyl) piperidin- 4-yl] oxy}quinazoline |
| US8426430B2 (en) | 2008-06-30 | 2013-04-23 | Hutchison Medipharma Enterprises Limited | Quinazoline derivatives |
| US8648191B2 (en) | 2008-08-08 | 2014-02-11 | Boehringer Ingelheim International Gmbh | Cyclohexyloxy substituted heterocycles, pharmaceutical compositions containing these compounds and processes for preparing them |
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| BR112015022576A2 (pt) | 2013-03-14 | 2017-10-24 | Genentech Inc | produto farmacêutico e seu uso, kit e método para tratar uma disfunção hiperproliferativa |
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| US5760041A (en) * | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
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- 1998-11-04 HU HU0004286A patent/HUP0004286A3/hu unknown
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- 1998-11-04 EP EP98956600A patent/EP1039910A1/fr not_active Withdrawn
- 1998-11-04 KR KR1020007004883A patent/KR20010031813A/ko not_active Withdrawn
- 1998-11-04 PL PL98340800A patent/PL340800A1/xx unknown
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- 1998-11-04 AU AU13087/99A patent/AU1308799A/en not_active Abandoned
- 1998-11-04 NZ NZ503991A patent/NZ503991A/en unknown
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| PL340800A1 (en) | 2001-02-26 |
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| HUP0004286A2 (hu) | 2001-11-28 |
| KR20010031813A (ko) | 2001-04-16 |
| NO20002166D0 (no) | 2000-04-27 |
| NO20002166L (no) | 2000-06-28 |
| JP2001522802A (ja) | 2001-11-20 |
| NZ503991A (en) | 2001-11-30 |
| AR016415A1 (es) | 2001-07-04 |
| CN1278176A (zh) | 2000-12-27 |
| BR9814116A (pt) | 2000-10-03 |
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