AR051753A1 - METHODS TO PREPARE INDAZOL COMPOUNDS - Google Patents
METHODS TO PREPARE INDAZOL COMPOUNDSInfo
- Publication number
- AR051753A1 AR051753A1 ARP050104567A ARP050104567A AR051753A1 AR 051753 A1 AR051753 A1 AR 051753A1 AR P050104567 A ARP050104567 A AR P050104567A AR P050104567 A ARP050104567 A AR P050104567A AR 051753 A1 AR051753 A1 AR 051753A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- formula
- compound
- substituted
- aryl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Los compuestos de la formula (1) son utiles como agentes anti-angiogénesis y como agentes para modular y/o inhibir la actividad de proteínas quinasas. Reivindicacion 1: Un método para preparar un compuesto de formula (1) o una sal o solvato de éste aceptable desde un punto de vista farmacéutico, en la que: R1 es un grupo de la formula -CH=CHR4 o -CH=NR4, y R1 está sustituido con 0 a 4 grupos R5; R2 es alquilo C1-12, cicloalquilo C3-12, heterocicloalquilo de 5 a 12 miembros, arilo C6-12, heteroarilo de 5 a 12 miembros, alcoxi C1-12, ariloxi C6-12, cicloalcoxi C3-12, -NH-alquilo C1-8, -NHarilo C6-12, -NHheteroarilo de 5 a 12 miembros, -N=CHalquilo C1-12, -NH(C=O)H, -NH(CO)R5, o -NH2, y R2 está sustituido con 0 a 4 grupos R5; cada R3 es de manera independiente H, halogeno, o alquilo C1-8, y el alquilo C1-8 está sustituido con 0 a 4 grupos R5; R4 es alquilo C1-12, cicloalquilo C3-12, heterociclilo de 5 a 12 miembros, arilo C6-12, o heteroarilo de 5 a 12 miembros, y R4 está sustituido con 0 a 4 grupos R5; cada R5 es de manera independiente halogeno, alquilo C1-8, alquenilo C2-8, alquilo C2-8, -OH, -NO2, -CN, -CO2H, -Oalquilo C1-8, arilo C6-12, arilo C6-12-alquilo C1-8, -CO2CH3, -CONH2, -OCH2CONH2, -NH2, -SO2NH2, alquilo C1-12 sustituido con halogeno, o -Oalquilo C1-12 sustituido con halogeno; que comprende: a) hacer reaccionar un compuesto de formula (2) con un compuesto de formula (3) para proporcionar un compuesto de formula (4) en el que la reaccion se produce en presencia de un catalizador y una base; W es un grupo protector; X es un grupo sustituyente activado; y R1, R2, y R3 son como se han descrito más arriba; y b) desproteger el compuesto de formula (4) para proporcionar el compuesto de formula (1).The compounds of the formula (1) are useful as anti-angiogenesis agents and as agents to modulate and / or inhibit the activity of protein kinases. Claim 1: A method for preparing a compound of formula (1) or a pharmaceutically acceptable salt or solvate thereof, wherein: R1 is a group of the formula -CH = CHR4 or -CH = NR4, and R1 is substituted with 0 to 4 R5 groups; R2 is C1-12 alkyl, C3-12 cycloalkyl, 5-12 membered heterocycloalkyl, C6-12 aryl, 5-12 membered heteroaryl, C1-12 alkoxy, C6-12 aryloxy, C3-12 cycloalkoxy, -NH-alkyl C1-8, -N C6-12aryl, -NH 5-12 membered heteroaryl, -N = CH12-12alkyl, -NH (C = O) H, -NH (CO) R5, or -NH2, and R2 is substituted with 0 to 4 R5 groups; each R3 is independently H, halogen, or C1-8 alkyl, and C1-8 alkyl is substituted with 0 to 4 R5 groups; R4 is C1-12 alkyl, C3-12 cycloalkyl, 5-12 membered heterocyclyl, C6-12 aryl, or 5-12 membered heteroaryl, and R4 is substituted with 0 to 4 R5 groups; each R5 is independently halogen, C1-8 alkyl, C2-8 alkenyl, C2-8 alkyl, -OH, -NO2, -CN, -CO2H, -C1-8 alkyl, C6-12 aryl, C6-12 aryl -C1-8 alkyl, -CO2CH3, -CONH2, -OCH2CONH2, -NH2, -SO2NH2, halogen substituted C1-12 alkyl, or halogen substituted C1-12 alkyl; comprising: a) reacting a compound of formula (2) with a compound of formula (3) to provide a compound of formula (4) in which the reaction occurs in the presence of a catalyst and a base; W is a protective group; X is an activated substituent group; and R1, R2, and R3 are as described above; and b) deprotecting the compound of formula (4) to provide the compound of formula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62457504P | 2004-11-02 | 2004-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR051753A1 true AR051753A1 (en) | 2007-02-07 |
Family
ID=35528034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP050104567A AR051753A1 (en) | 2004-11-02 | 2005-11-01 | METHODS TO PREPARE INDAZOL COMPOUNDS |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1809625A1 (en) |
| JP (1) | JP2008518901A (en) |
| KR (1) | KR20070058689A (en) |
| CN (1) | CN101044138A (en) |
| AR (1) | AR051753A1 (en) |
| AU (1) | AU2005300311A1 (en) |
| BR (1) | BRPI0517921A (en) |
| CA (1) | CA2586176A1 (en) |
| IL (1) | IL182096A0 (en) |
| MX (1) | MX2007003603A (en) |
| NO (1) | NO20072747L (en) |
| RU (1) | RU2007114112A (en) |
| TW (1) | TW200614990A (en) |
| WO (1) | WO2006048745A1 (en) |
| ZA (1) | ZA200702317B (en) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008044045A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| JP5528806B2 (en) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | Compound drug |
| FI2134702T4 (en) | 2007-04-05 | 2023-09-12 | Crystalline forms of 6-[2-(methylcarbamoyl)phenylsulfanyl]-3-e-[2-(pyridin-2-yl)ethenyl]indazole suitable for the treatment of abnormal cell growth in mammals | |
| US8354528B2 (en) * | 2007-10-25 | 2013-01-15 | Genentech, Inc. | Process for making thienopyrimidine compounds |
| EP2163544A1 (en) * | 2008-09-16 | 2010-03-17 | Pfizer, Inc. | Methods of preparing indazole compounds |
| TW201328725A (en) | 2011-09-30 | 2013-07-16 | Pfizer | Pharmaceutical compositions of N-methyl-2-3-((E)-2-pyridin-2-yl-vinyl)-1H-indazol-6-ylsulfanyl-benzamide |
| MX2014005715A (en) | 2011-11-11 | 2014-05-28 | Pfizer | N-methyl-2-[3-((e)-2-pyridin-2-yl-vinyl)-1h-indazol-6-ylsulfanyl ]-benzamide for the treatment of chronic myelogenous leukemia. |
| EP2792360A1 (en) | 2013-04-18 | 2014-10-22 | IP Gesellschaft für Management mbH | (1aR,12bS)-8-cyclohexyl-11-fluoro-N-((1-methylcyclopropyl)sulfonyl)-1a-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-1,1a,2,2b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide for use in treating HCV |
| CN103387565B (en) * | 2013-07-29 | 2014-10-29 | 苏州明锐医药科技有限公司 | Preparation method of Axitinib |
| CN103570696B (en) * | 2013-11-06 | 2016-02-24 | 湖南欧亚生物有限公司 | A kind of preparation method of Axitinib intermediate and preparing the application in Axitinib |
| WO2015067224A1 (en) | 2013-11-08 | 2015-05-14 | Zentiva, K.S. | Salts of 6-[2-(methylcarbamoyl)phenylsulfanyl]-3-e-[2-(pyridin-2-yl)ethanyl] indazole |
| ES2710211T3 (en) | 2014-02-04 | 2019-04-23 | Pfizer | Combination of a PD-1 antagonist and a VEGFR inhibitor to treat cancer |
| ES2647262T3 (en) * | 2014-03-31 | 2017-12-20 | Senju Pharmaceutical Co. Ltd | Alkynyl indazole derivative and use thereof |
| CN104072484B (en) * | 2014-07-07 | 2016-07-06 | 渤海大学 | Nitrogen-(4-(aromatic thiohydroxy)-1 hydrogen-indazole-3-base)-1-(heteroaromatic replacement) methylene imine compounds and pharmaceutically acceptable salt and its preparation method and application thereof |
| JP2017530950A (en) | 2014-08-25 | 2017-10-19 | ファイザー・インコーポレイテッド | Combination of PD-1 antagonist and ALK inhibitor for treating cancer |
| WO2016057931A1 (en) | 2014-10-10 | 2016-04-14 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
| RU2714233C2 (en) | 2015-02-26 | 2020-02-13 | Мерк Патент Гмбх | Pd-1/pd-l1 inhibitors for treating cancer |
| US9580406B2 (en) | 2015-04-28 | 2017-02-28 | Signa S.A. De C.V. | Processes for the preparation of axitinib |
| CA2989586A1 (en) | 2015-06-16 | 2016-12-22 | Pfizer, Inc. | Pd-l1 antagonist combination treatments |
| KR20190062515A (en) | 2016-10-06 | 2019-06-05 | 화이자 인코포레이티드 | Usage of Abelipab for the Treatment of Cancer |
| WO2020128893A1 (en) | 2018-12-21 | 2020-06-25 | Pfizer Inc. | Combination treatments of cancer comprising a tlr agonist |
| US20220194921A1 (en) | 2019-04-18 | 2022-06-23 | Synthon B.V. | Process for preparation of axitinib |
| CN112209861A (en) * | 2019-07-11 | 2021-01-12 | 鲁南制药集团股份有限公司 | Acixtinib intermediate compound and preparation method thereof |
| CN112442010B (en) * | 2019-08-30 | 2023-10-03 | 润佳（苏州）医药科技有限公司 | Prodrug compounds and application thereof in treating cancers |
| CN111440102B (en) * | 2020-04-26 | 2022-02-15 | 大连凯飞化学股份有限公司 | Preparation method of dithiodibenzoamide compound |
| WO2023166420A1 (en) | 2022-03-03 | 2023-09-07 | Pfizer Inc. | Multispecific antibodies and uses thereof |
| CN114591338B (en) * | 2022-03-31 | 2023-05-09 | 苏州欧康维视生物科技有限公司 | Preparation method and application of Syk and VEGFR2 double-target inhibitor |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20010306A1 (en) * | 1999-07-02 | 2001-03-29 | Agouron Pharma | INDAZOLE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM USEFUL FOR THE INHIBITION OF PROTEIN KINASE |
| CN1747950A (en) * | 2002-12-19 | 2006-03-15 | 美国辉瑞有限公司 | 2-(1h-indazole-6-ylamino)-benzamide compounds as protein kinases inhibitors useful for the treatment of ophthalmic diseases |
| EP1606283B1 (en) * | 2003-03-03 | 2008-10-08 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| WO2005094823A1 (en) * | 2004-03-30 | 2005-10-13 | Kyowa Hakko Kogyo Co., Ltd. | Flt-3 INHIBITOR |
-
2005
- 2005-10-21 KR KR1020077009804A patent/KR20070058689A/en not_active Application Discontinuation
- 2005-10-21 AU AU2005300311A patent/AU2005300311A1/en not_active Abandoned
- 2005-10-21 CA CA002586176A patent/CA2586176A1/en not_active Abandoned
- 2005-10-21 CN CNA2005800361530A patent/CN101044138A/en active Pending
- 2005-10-21 MX MX2007003603A patent/MX2007003603A/en unknown
- 2005-10-21 WO PCT/IB2005/003300 patent/WO2006048745A1/en active Application Filing
- 2005-10-21 RU RU2007114112/04A patent/RU2007114112A/en not_active Application Discontinuation
- 2005-10-21 EP EP05796299A patent/EP1809625A1/en not_active Withdrawn
- 2005-10-21 BR BRPI0517921-1A patent/BRPI0517921A/en not_active IP Right Cessation
- 2005-10-21 JP JP2007538538A patent/JP2008518901A/en not_active Withdrawn
- 2005-11-01 AR ARP050104567A patent/AR051753A1/en not_active Application Discontinuation
- 2005-11-01 TW TW094138224A patent/TW200614990A/en unknown
-
2007
- 2007-03-20 ZA ZA200702317A patent/ZA200702317B/en unknown
- 2007-03-21 IL IL182096A patent/IL182096A0/en unknown
- 2007-05-30 NO NO20072747A patent/NO20072747L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2005300311A1 (en) | 2006-05-11 |
| CA2586176A1 (en) | 2006-05-11 |
| NO20072747L (en) | 2007-07-31 |
| EP1809625A1 (en) | 2007-07-25 |
| JP2008518901A (en) | 2008-06-05 |
| KR20070058689A (en) | 2007-06-08 |
| MX2007003603A (en) | 2007-05-21 |
| IL182096A0 (en) | 2007-07-24 |
| BRPI0517921A (en) | 2008-10-21 |
| TW200614990A (en) | 2006-05-16 |
| RU2007114112A (en) | 2008-12-10 |
| ZA200702317B (en) | 2008-09-25 |
| WO2006048745A1 (en) | 2006-05-11 |
| CN101044138A (en) | 2007-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |