AR013137A1 - Procedimiento para preparar 4-sustituido-1h-indol-3-glioxamidas, compuestos intermedios utilizados en dicho procedimiento y proceso para preparardichos compuestos intermedios - Google Patents
Procedimiento para preparar 4-sustituido-1h-indol-3-glioxamidas, compuestos intermedios utilizados en dicho procedimiento y proceso para preparardichos compuestos intermediosInfo
- Publication number
- AR013137A1 AR013137A1 ARP980103072A ARP980103072A AR013137A1 AR 013137 A1 AR013137 A1 AR 013137A1 AR P980103072 A ARP980103072 A AR P980103072A AR P980103072 A ARP980103072 A AR P980103072A AR 013137 A1 AR013137 A1 AR 013137A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- alkyl
- halo
- group
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/14—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom with carbocyclic rings directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Un procedimiento para la preparacion de 1H-indol-3-glioxamidas utiles para inhibir el SPLA2 y nuevos productos intermedios utiles en la preparacion detales compuestos. Un procedimiento para la preparacion de un compuesto de formula (I) o una sal farmacéuticamente aceptable o un profármaco derivadodel mismo, en el que: R1 se selecciona del grupo que consta de C7-20 alquilo y formulas (II), en las que R10 se selecciona del grupo que consta de halo,alquilo C1-10, alcoxi C1-10, -S-(alquilo C1-10) y halo alquilo C1-10, y t es un numero entero de 0 a 5 ambos inclusive; R2 se selecciona del grupo queconsta de hidrogeno, halo, alquilo C1-3, cicloalquilo C3-4, cicloalquenilo C3-4, -O-(alquilo C1-2), -S-(alquilo C1-2), arilo, ariloxi, y HET; R4 seselecciona del grupo que consta de -CO2H, -SO3H y -P(O)(OH)2 o una sal o un profármaco derivados del mismo; y R5, R6 y R7 son cada un independientementeseleccionados del grupo que consta de hidrogeno, alquilo C1-6, alcoxi C1-6,halo alcoxi C1-6, halo alquilo C2-6, bromo, cloro, fluoro, yodo y arilo;comprendiendo el procedimiento las etapas de: a) halogenar un compuesto de formula (X), en el que R8 es alquilo C1-6, arilo o HET; con SO2Cl2 paraformar un compuesto de formula (IX); b) hidrolizar y descarboxilar un compuesto de formula (IX) para formar un compuesto de formula (VIII); c) alquilar uncompuesto de formula (VII); con un compuesto de formula (VIII) para formar un compuesto de formula (VI); d)aminar ydeshidratar un compuesto de formula(VI) con una amina de formula R1NH2 en presencia de un disolvente que forma un azeotropo con agua para formar un compuesto de formula (V); e) oxidar uncompuesto de formula (V) por reflujo en un disolvente hidrocarbonado polar que tiene un punto de ebullicion de al menos 150°C y una constante dieléctrica
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5087797P | 1997-06-26 | 1997-06-26 | |
| US5089197P | 1997-06-26 | 1997-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR013137A1 true AR013137A1 (es) | 2000-12-13 |
Family
ID=26728795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP980103072A AR013137A1 (es) | 1997-06-26 | 1998-06-26 | Procedimiento para preparar 4-sustituido-1h-indol-3-glioxamidas, compuestos intermedios utilizados en dicho procedimiento y proceso para preparardichos compuestos intermedios |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5986106A (es) |
| EP (1) | EP0887342A3 (es) |
| JP (1) | JP2002506460A (es) |
| KR (1) | KR20010014167A (es) |
| CN (2) | CN1268119A (es) |
| AR (1) | AR013137A1 (es) |
| AU (1) | AU735516B2 (es) |
| BR (1) | BR9810481A (es) |
| CA (1) | CA2293459A1 (es) |
| CO (1) | CO4950517A1 (es) |
| EA (1) | EA002119B1 (es) |
| EG (1) | EG22077A (es) |
| HU (1) | HUP0003019A3 (es) |
| ID (1) | ID24356A (es) |
| IL (1) | IL133624A0 (es) |
| NO (1) | NO996432L (es) |
| NZ (1) | NZ501780A (es) |
| PE (1) | PE84199A1 (es) |
| PL (1) | PL337690A1 (es) |
| TR (1) | TR200000440T2 (es) |
| TW (1) | TW455581B (es) |
| UA (1) | UA56245C2 (es) |
| WO (1) | WO1999000360A1 (es) |
| ZA (1) | ZA985561B (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010042307A (ko) | 1998-03-31 | 2001-05-25 | 시오노 요시히코 | 피롤로[1,2-ａ]피라진 ｓＰＬＡ2 억제제 |
| US6133453A (en) * | 1998-05-15 | 2000-10-17 | Pharm-Eco Laboratories, Inc. | Method for making substituted indoles |
| JP4544446B2 (ja) | 1998-05-21 | 2010-09-15 | 塩野義製薬株式会社 | ｓＰＬＡ２阻害作用を有するピロロ［１，２−ｂ］ピリダジン誘導体 |
| DE69931963D1 (de) * | 1998-10-14 | 2006-07-27 | Shionogi & Co | Spla2-inhibitoren zur behandlung von ischämischen reperfusionsschäden |
| US6380397B1 (en) * | 1999-04-15 | 2002-04-30 | Eli Lilly And Company | Process for preparing 4-substituted-1H-indole-3-glyoxamides |
| DE19962300A1 (de) * | 1999-12-23 | 2001-06-28 | Asta Medica Ag | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
| HUP0400606A2 (hu) * | 2001-03-01 | 2004-12-28 | Ono Pharmaceutical Co., Ltd. | 2-Metil-indol-4-ecetsav és intermedierei és eljárás előállításukra |
| CN104292145A (zh) * | 2014-10-12 | 2015-01-21 | 湖南华腾制药有限公司 | 一种6-溴吲哚衍生物的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2145573A1 (de) * | 1971-09-11 | 1973-03-15 | Thiemann Chem Pharm Fab | Indol-verbindungen, derivate derselben und verfahren zu ihrer herstellung |
| JPS55127367A (en) * | 1979-03-23 | 1980-10-02 | Shiono Koryo Kk | Novel process for preparation of 4-(2-hydroxy-3- isopropylaminopropoxy)indole |
| DK1950200T3 (da) * | 1994-04-01 | 2012-04-10 | Lilly Co Eli | [[3-(2-AMINO-1,2-DIOXOETHYL)-2-ETHYL-1-(PHENYLMETHYL)-11H-INDOL-4-YL]OXY]EDDIKESYREMETHYLESTER SOM sPLA2-INHIBITOR |
| US5705501A (en) * | 1994-11-17 | 1998-01-06 | Molecular Geriatrics Corporation | Certain substituted 1-aryl-3-morpholinopropanones to treat Alzheimer's Disease |
-
1998
- 1998-06-19 TW TW087109902A patent/TW455581B/zh not_active IP Right Cessation
- 1998-06-22 EA EA200000069A patent/EA002119B1/ru not_active IP Right Cessation
- 1998-06-22 WO PCT/US1998/012173 patent/WO1999000360A1/en not_active Application Discontinuation
- 1998-06-22 HU HU0003019A patent/HUP0003019A3/hu unknown
- 1998-06-22 UA UA99127079A patent/UA56245C2/uk unknown
- 1998-06-22 NZ NZ501780A patent/NZ501780A/xx unknown
- 1998-06-22 AU AU79613/98A patent/AU735516B2/en not_active Ceased
- 1998-06-22 ID IDW991675A patent/ID24356A/id unknown
- 1998-06-22 TR TR2000/00440T patent/TR200000440T2/xx unknown
- 1998-06-22 BR BR9810481-0A patent/BR9810481A/pt not_active IP Right Cessation
- 1998-06-22 CN CN98808438A patent/CN1268119A/zh active Pending
- 1998-06-22 PE PE1998000549A patent/PE84199A1/es not_active Application Discontinuation
- 1998-06-22 PL PL98337690A patent/PL337690A1/xx unknown
- 1998-06-22 KR KR1019997012238A patent/KR20010014167A/ko not_active Application Discontinuation
- 1998-06-22 JP JP50556899A patent/JP2002506460A/ja active Pending
- 1998-06-22 IL IL13362498A patent/IL133624A0/xx unknown
- 1998-06-22 CA CA002293459A patent/CA2293459A1/en not_active Abandoned
- 1998-06-24 CO CO98035912A patent/CO4950517A1/es unknown
- 1998-06-25 EP EP98304994A patent/EP0887342A3/en not_active Withdrawn
- 1998-06-25 EG EG74498A patent/EG22077A/xx active
- 1998-06-25 ZA ZA9805561A patent/ZA985561B/xx unknown
- 1998-06-26 US US09/105,381 patent/US5986106A/en not_active Expired - Fee Related
- 1998-06-26 AR ARP980103072A patent/AR013137A1/es not_active Application Discontinuation
-
1999
- 1999-12-23 NO NO996432A patent/NO996432L/no not_active Application Discontinuation
-
2001
- 2001-09-07 CN CN01132979A patent/CN1343662A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NO996432L (no) | 2000-02-09 |
| CO4950517A1 (es) | 2000-09-01 |
| JP2002506460A (ja) | 2002-02-26 |
| PL337690A1 (en) | 2000-08-28 |
| CA2293459A1 (en) | 1999-01-07 |
| BR9810481A (pt) | 2000-09-12 |
| HUP0003019A3 (en) | 2001-02-28 |
| PE84199A1 (es) | 1999-09-11 |
| EG22077A (en) | 2002-07-31 |
| WO1999000360A1 (en) | 1999-01-07 |
| AU7961398A (en) | 1999-01-19 |
| EP0887342A2 (en) | 1998-12-30 |
| KR20010014167A (ko) | 2001-02-26 |
| TR200000440T2 (tr) | 2000-07-21 |
| EP0887342A3 (en) | 1999-01-07 |
| CN1343662A (zh) | 2002-04-10 |
| CN1268119A (zh) | 2000-09-27 |
| TW455581B (en) | 2001-09-21 |
| US5986106A (en) | 1999-11-16 |
| UA56245C2 (uk) | 2003-05-15 |
| AU735516B2 (en) | 2001-07-12 |
| HUP0003019A2 (hu) | 2001-01-29 |
| IL133624A0 (en) | 2001-04-30 |
| EA002119B1 (ru) | 2001-12-24 |
| EA200000069A1 (ru) | 2000-06-26 |
| ZA985561B (en) | 2000-01-10 |
| ID24356A (id) | 2000-07-13 |
| NZ501780A (en) | 2002-08-28 |
| NO996432D0 (no) | 1999-12-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |