AR077667A1 - Procedimiento para la preparacion de 1- bencil-3 hidroximetil -1h- indazol - Google Patents
Procedimiento para la preparacion de 1- bencil-3 hidroximetil -1h- indazolInfo
- Publication number
- AR077667A1 AR077667A1 ARP100102815A ARP100102815A AR077667A1 AR 077667 A1 AR077667 A1 AR 077667A1 AR P100102815 A ARP100102815 A AR P100102815A AR P100102815 A ARP100102815 A AR P100102815A AR 077667 A1 AR077667 A1 AR 077667A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- alkyl group
- preparation
- benzyl
- react
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- AKQDXNFPEFHRLS-UHFFFAOYSA-N (1-benzylindazol-3-yl)methanol Chemical compound C12=CC=CC=C2C(CO)=NN1CC1=CC=CC=C1 AKQDXNFPEFHRLS-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
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
-
- 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
- C07D401/12—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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La presente se refiere a un procedimiento para la preparacion de 1-bencil-3-hidroximetil-1H-indazol segun la formula (2), que se va a utilizar en un procedimiento subsiguiente para la preparacion de 1-bencil-3-hidroximetil-1H-indazol segun la formula (1). Reivindicacion 1: Procedimiento para la preparacion de 1-bencil-3-hidroximetil-1H-indazol representado por la formula (2) en la que R1 y R2, que pueden ser iguales o diferentes, son hidrogeno o un grupo alquilo C1-6; R3, R4 y R8, que pueden ser iguales o diferentes, pueden ser hidrogeno, un grupo alquilo C1-5, alcoxi C1-3 y un átomo de halogeno, R5 puede ser hidrogeno, un grupo alquilo C1-5, alcoxi C1-3, un átomo de halogeno, o junto con R6 y R7 pueden formar un anillo de 5 o 6 átomos de carbono y, R6 y R7, que pueden ser iguales o diferentes, pueden ser hidrogeno, un grupo alquilo C1-5, o uno de entre R6 y R7 junto con R5 pueden formar un anillo de 5 o 6 átomos de carbono, en la que: a) un 1-bencil-3-halogeno-1H-indazol de formula (3) en la que X es un átomo de halogeno seleccionado de entre yodo y bromo, preferentemente yodo, se produce para reaccionar con un haluro de alquil-magnesio de formula RMgX' en la que R es un grupo alquilo C1-6 y X' es un átomo de halogeno seleccionado de entre bromo y cloro, preferentemente cloro, para formar el compuesto intermedio (4); b) dicho compuesto intermedio (4) se produce para reaccionar con un compuesto carbonilo de formula R1-CO-R2, para formar un compuesto de formula (2) o alternativamente a b); b') dicho compuesto intermedio (4) se produce para reaccionar con una amida de formula R'Rö-N-CO-R1, en la que R' y Rö, que pueden ser iguales o diferentes, son un grupo alquilo C1-3, para formar un compuesto intermedio (8) que se produce para reaccionar con un agente reductor del grupo carbonilo para formar un compuesto de formula (2).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09425314 | 2009-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR077667A1 true AR077667A1 (es) | 2011-09-14 |
Family
ID=41353924
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP100102815A AR077667A1 (es) | 2009-08-03 | 2010-08-02 | Procedimiento para la preparacion de 1- bencil-3 hidroximetil -1h- indazol |
| ARP100102816A AR077668A1 (es) | 2009-08-03 | 2010-08-02 | Procedimiento para la preparacion de 1-bencil-3-hidroximetil-1h-indazol |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP100102816A AR077668A1 (es) | 2009-08-03 | 2010-08-02 | Procedimiento para la preparacion de 1-bencil-3-hidroximetil-1h-indazol |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US8350052B2 (es) |
| EP (2) | EP2462118B1 (es) |
| JP (3) | JP5640086B2 (es) |
| KR (2) | KR101735577B1 (es) |
| CN (3) | CN106518769A (es) |
| AR (2) | AR077667A1 (es) |
| AU (1) | AU2010280828B2 (es) |
| BR (2) | BR112012002130A2 (es) |
| CA (2) | CA2765461C (es) |
| DK (2) | DK2462118T3 (es) |
| EA (2) | EA019672B1 (es) |
| ES (2) | ES2480278T3 (es) |
| GE (2) | GEP20135878B (es) |
| HK (2) | HK1165408A1 (es) |
| IL (2) | IL216854A (es) |
| MX (2) | MX2012001519A (es) |
| PL (2) | PL2462118T3 (es) |
| PT (2) | PT2462119E (es) |
| SG (2) | SG176950A1 (es) |
| SI (2) | SI2462119T1 (es) |
| UA (2) | UA106886C2 (es) |
| WO (2) | WO2011015501A1 (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5509100B2 (ja) * | 2008-03-07 | 2014-06-04 | アジェンデ・キミケ・リウニテ・アンジェリニ・フランチェスコ・ア・チ・エレ・ア・エフェ・ソシエタ・ペル・アチオニ | 新規な１−ベンジル−３−ヒドロキシメチルインダゾール誘導体及びそのＭＣＰ−１，ＣＸ３ＣＲ１及びｐ４０の発現に基づく疾病の治療への使用 |
| RU2645344C2 (ru) * | 2012-05-18 | 2018-02-21 | Санофи | Производные пиразола и их применение в качестве lpar5 антагонистов |
| JP2015521183A (ja) | 2012-05-18 | 2015-07-27 | サノフイ | ピリジン誘導体および病理学的血栓形成に関連する状態の治療へのその使用 |
| CN104876872B (zh) * | 2015-04-24 | 2017-07-07 | 昆明理工大学 | 一种制备1‑叔丁氧基羰基‑3‑羟甲基吲唑的方法及应用 |
| WO2016203313A1 (en) * | 2015-06-16 | 2016-12-22 | Translatum Medicus, Inc. | Compositions and methods for treating and diagnosing ocular disorders |
| CA3144861A1 (en) | 2019-06-25 | 2020-12-30 | Translatum Medicus, Inc. | Processes of making 2-((1-benzyl-1h-indazol-3-yl)methoxy)-2-methylpropanoic acid and its derivatives |
| CN113929627A (zh) * | 2021-10-19 | 2022-01-14 | 吕梁学院 | 一种宾达利的合成方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB860303A (en) | 1958-06-20 | 1961-02-01 | Ici Ltd | Pharmaceutical compositions comprising ª‡-aryloxy-aliphatic carboxylic acids and/or ª |
| GB8707051D0 (en) * | 1986-04-15 | 1987-04-29 | Ici America Inc | Heterocyclic carboxamides |
| IT1230441B (it) * | 1989-02-07 | 1991-10-23 | Acraf | Eteri della serie dell'indazolo |
| IT1253703B (it) | 1991-04-22 | 1995-08-23 | Angelini Francesco Ist Ricerca | Uso di acidi metossi alcanoici dell'indazolo per preparare un farmaco attivo nel trattamento di malattie autoimmunitarie |
| JP3159614B2 (ja) * | 1994-11-28 | 2001-04-23 | 三井化学株式会社 | クロロアルキルアミン塩酸塩の製造法 |
| IT1276031B1 (it) | 1995-10-31 | 1997-10-24 | Angelini Ricerche Spa | Composizione farmaceutica per il trattamento delle malattie autoimmuni |
| IT1293795B1 (it) * | 1997-07-28 | 1999-03-10 | Angelini Ricerche Spa | Farmaco attivo nel ridurre la produzione di proteina mcp-1 |
| JP2001081080A (ja) * | 1999-09-14 | 2001-03-27 | Nissan Chem Ind Ltd | ４（５）−クロロメチル−２−フェニル−１，２，３−トリアゾール誘導体の製造法 |
| GB0028367D0 (en) * | 2000-11-21 | 2001-01-03 | Celltech Chiroscience Ltd | Chemical compounds |
| JP2006137718A (ja) | 2004-11-12 | 2006-06-01 | Astellas Pharma Inc | インドール若しくはインダゾール誘導体 |
| DK1906965T3 (en) * | 2005-06-22 | 2015-08-03 | Chemocentryx Inc | Azaindazol compounds and methods of use thereof |
| US7777035B2 (en) * | 2005-06-22 | 2010-08-17 | Chemocentryx, Inc. | Azaindazole compounds and methods of use |
| US7858645B2 (en) * | 2006-11-01 | 2010-12-28 | Hoffmann-La Roche Inc. | Indazole derivatives |
| ITMI20062254A1 (it) | 2006-11-24 | 2008-05-25 | Acraf | Uso di un acido metossi-alcanoico dell'indazolo per preparare una composizione farmaceutca |
| US20090047246A1 (en) * | 2007-02-12 | 2009-02-19 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
| AU2008256940A1 (en) * | 2007-05-25 | 2008-12-04 | Elan Pharmaceuticals, Inc. | Pyrazolopyrrolidines as inhibitors of gamma secretase |
| MX2010009411A (es) * | 2008-02-29 | 2010-11-30 | Array Biopharma Inc | Compuestos del inhibidor de raf y métodos de uso de los mismos. |
| BRPI0907976A2 (pt) * | 2008-03-07 | 2015-08-04 | Acraf | Composto, composição farmacêutica, uso de um composto, e, método para tratar ou prevenir doenças |
-
2010
- 2010-07-28 PL PL10735298T patent/PL2462118T3/pl unknown
- 2010-07-28 KR KR1020127002338A patent/KR101735577B1/ko active IP Right Grant
- 2010-07-28 AU AU2010280828A patent/AU2010280828B2/en not_active Ceased
- 2010-07-28 CN CN201610870938.8A patent/CN106518769A/zh active Pending
- 2010-07-28 SG SG2011095023A patent/SG176950A1/en unknown
- 2010-07-28 EA EA201270237A patent/EA019672B1/ru not_active IP Right Cessation
- 2010-07-28 PT PT107393449T patent/PT2462119E/pt unknown
- 2010-07-28 PL PL10739344T patent/PL2462119T3/pl unknown
- 2010-07-28 UA UAA201115299A patent/UA106886C2/uk unknown
- 2010-07-28 SI SI201030729T patent/SI2462119T1/sl unknown
- 2010-07-28 MX MX2012001519A patent/MX2012001519A/es active IP Right Grant
- 2010-07-28 UA UAA201115300A patent/UA106988C2/uk unknown
- 2010-07-28 SG SG2011093309A patent/SG176885A1/en unknown
- 2010-07-28 ES ES10739344.9T patent/ES2480278T3/es active Active
- 2010-07-28 DK DK10735298.1T patent/DK2462118T3/da active
- 2010-07-28 SI SI201030728T patent/SI2462118T1/sl unknown
- 2010-07-28 GE GEAP201012610A patent/GEP20135878B/en unknown
- 2010-07-28 JP JP2012523288A patent/JP5640086B2/ja not_active Expired - Fee Related
- 2010-07-28 WO PCT/EP2010/060937 patent/WO2011015501A1/en active Application Filing
- 2010-07-28 CA CA2765461A patent/CA2765461C/en not_active Expired - Fee Related
- 2010-07-28 CN CN2010800344095A patent/CN102471282A/zh active Pending
- 2010-07-28 CA CA2766235A patent/CA2766235C/en not_active Expired - Fee Related
- 2010-07-28 BR BR112012002130A patent/BR112012002130A2/pt not_active Application Discontinuation
- 2010-07-28 GE GEAP201012611A patent/GEP20135879B/en unknown
- 2010-07-28 EP EP10735298.1A patent/EP2462118B1/en not_active Not-in-force
- 2010-07-28 DK DK10739344.9T patent/DK2462119T3/da active
- 2010-07-28 EP EP10739344.9A patent/EP2462119B1/en not_active Not-in-force
- 2010-07-28 JP JP2012523289A patent/JP6200153B2/ja not_active Expired - Fee Related
- 2010-07-28 US US13/381,137 patent/US8350052B2/en not_active Expired - Fee Related
- 2010-07-28 CN CN201080034391.9A patent/CN102471281B/zh not_active Expired - Fee Related
- 2010-07-28 WO PCT/EP2010/060941 patent/WO2011015502A1/en active Application Filing
- 2010-07-28 US US13/377,588 patent/US8354544B2/en not_active Expired - Fee Related
- 2010-07-28 MX MX2012001520A patent/MX2012001520A/es active IP Right Grant
- 2010-07-28 PT PT107352981T patent/PT2462118E/pt unknown
- 2010-07-28 KR KR1020127001575A patent/KR101736301B1/ko active IP Right Grant
- 2010-07-28 EA EA201270236A patent/EA019060B1/ru not_active IP Right Cessation
- 2010-07-28 ES ES10735298.1T patent/ES2481393T3/es active Active
- 2010-07-28 BR BRBR112012001731-4A patent/BR112012001731A2/pt not_active Application Discontinuation
- 2010-08-02 AR ARP100102815A patent/AR077667A1/es unknown
- 2010-08-02 AR ARP100102816A patent/AR077668A1/es unknown
-
2011
- 2011-12-08 IL IL216854A patent/IL216854A/en not_active IP Right Cessation
- 2011-12-20 IL IL217097A patent/IL217097A/en not_active IP Right Cessation
-
2012
- 2012-06-18 HK HK12105913.9A patent/HK1165408A1/xx not_active IP Right Cessation
- 2012-06-18 HK HK12105914.8A patent/HK1165409A1/xx not_active IP Right Cessation
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2015
- 2015-06-09 JP JP2015116951A patent/JP2015205900A/ja active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |