CO5080803A1 - Proceso de preparacion de 4-substituido-1h-indol-3-glioxami- das - Google Patents
Proceso de preparacion de 4-substituido-1h-indol-3-glioxami- dasInfo
- Publication number
- CO5080803A1 CO5080803A1 CO99022895A CO99022895A CO5080803A1 CO 5080803 A1 CO5080803 A1 CO 5080803A1 CO 99022895 A CO99022895 A CO 99022895A CO 99022895 A CO99022895 A CO 99022895A CO 5080803 A1 CO5080803 A1 CO 5080803A1
- Authority
- CO
- Colombia
- Prior art keywords
- formula
- compound
- jpeg
- mfi
- emi file
- Prior art date
Links
Classifications
-
- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
-
- 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)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Un proceso de preparación de un compuesto de la fórmula I o una sal o prodroga derivada del mismo farmacéuticamente aceptable<EMI FILE="99022895_1" ID="1" IMF=JPEG >En donde:R1 es seleccionado del grupo que consiste de alquilo C7-C20;<EMI FILE="99022895_2" ID="2" IMF=JPEG >donde;R10 es seleccionado del grupo que consiste de halo, alquilo C1-C10, alcoxi C1-C10, -S-(aquil C1-C10) y halo alquilo C1-C10 y t es un entero entre 0 y 5 ambos incluidos; R2 es seleccionado del grupo que consiste de hidrógeno, halo, alquilo C1-C3, cicloalquilo C3-C4, cicloalquenilo C3-C4, -O-(alquil C1-C2), -S-(alquilo C1-C2), aril, ariloxi, y HET corresponde a un anillo heterocíclico que incluye piridina, pirazina, pirimidina, piridazina, pirazol, furano, tiofeno, tiofeno, tiazol, isotiazol, oxadiazol, imidazol, triazol y tetrazol;R4 es seleccionado del grupo que consiste de -CO2H, -SO3H, y -P(O)(OH)2 o una sal o prodroga derivadas del mismo; yR5 es seleccionado del grupo que consiste de hidrógeno, alquilo (C1-C6), alcoxi (C1-C6), halo alcoxi(C1-C6), halo alquil (C1-C6), bromo, cloro, flúor, yodo y arilo;Proceso que comprende los siguientes pasos:a) Halogenación de un compuesto de fórmula X<EMI FILE="99022895_3" ID="3" IMF=JPEG >En donde R8 es alquil (C1-C6), arilo o HET, en donde HET corresponde a un anillo heterocíclico que incluye piridina, pirazina, pirimidina, piridazina, pirrol, pirazol, furano, tiofeno, tiazol, isotiazol, oxadiazol, tiadiazol, imidazol, triazol y tetrazol;Con SO2Cl2 para formar un compuesto de fórmula IX<EMI FILE="99022895_4" ID="4" IMF=JPEG >b) Hidrolización y descarboxilación de un compuesto de fórmula IX<EMI FILE="99022895_5" ID="5" IMF=JPEG >- 2 -- 2 -Para formar un compuesto de fórmula VIII<EMI FILE="99022895_6" ID="6" IMF=JPEG >c) Alquilación de un compuesto de fórmula VII<EMI FILE="99022895_7" ID="7" IMF=JPEG >Con un compuesto de fórmula VIII<EMI FILE="99022895_8" ID="8" IMF=JPEG >Para formar un compuesto de fórmula VI<EMI FILE="99022895_9" ID="9" IMF=JPEG >d) Aminación y deshidratación de un compuesto de fórmula VI<EMI FILE="99022895_10" ID="10" IMF=JPEG >Con una amina de la fórmula R1NH2 en presencia de un solvente que formar un azeótropo con agua para formar un compuesto de formula V<EMI FILE="99022895_11" ID="11" IMF=JPEG >e) Oxidación de un compuesto de fórmula V<EMI FILE="99022895_12" ID="12" IMF=JPEG >Por el calentamiento por una base y un reactivo sulfinilante de la fórmula RSOX donde R es alquilo-( C1-C6) o arilo y X es alcoxi (C1-C6), halo, o -OCO2 alquilo(C1-C6) para formar un compuesto de fórmula IV<EMI FILE="99022895_13" ID="13" IMF=JPEG >f) Alquilación de un compuesto de fórmula IV<EMI FILE="99022895_14" ID="14" IMF=JPEG >con un agente alquilante de la fórmula XCH2R4a donde X es un grupo saliente y R4a es -CO2R4b , -SO3R4b , -P(O)(OR4b)2, o -P(O)(OR4b)H, donde R4b es un grupo protector ácido, para formar un compuesto de fórmula III<EMI FILE="99022895_15" ID="15" IMF=JPEG >g) Reacción de un compuesto de fórmula III<EMI FILE="99022895_16" ID="16" IMF=JPEG >con cloruro de oxalil y amoniaco para formar un compuesto de fórmula II<EMI FILE="99022895_17" ID="17" IMF=JPEG >h) Opcionalmente, hidrolización de un compuesto de fórmula II<EMI FILE="99022895_18" ID="18" IMF=JPEG >Para formar un compuesto de fórmula I; yi) Opcionalmente, salificación de un compuesto de fórmula I.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8211098P | 1998-04-17 | 1998-04-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CO5080803A1 true CO5080803A1 (es) | 2001-09-25 |
Family
ID=22169126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CO99022895A CO5080803A1 (es) | 1998-04-17 | 1999-04-16 | Proceso de preparacion de 4-substituido-1h-indol-3-glioxami- das |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6265591B1 (es) |
| EP (1) | EP1071663A4 (es) |
| JP (1) | JP2002512225A (es) |
| KR (1) | KR20010042741A (es) |
| CN (1) | CN1305459A (es) |
| AR (1) | AR015767A1 (es) |
| AU (1) | AU750368B2 (es) |
| BR (1) | BR9909697A (es) |
| CA (1) | CA2326515A1 (es) |
| CO (1) | CO5080803A1 (es) |
| DZ (1) | DZ2770A1 (es) |
| EA (1) | EA003582B1 (es) |
| EG (1) | EG22139A (es) |
| HK (1) | HK1039120A1 (es) |
| HR (1) | HRP20000685A2 (es) |
| HU (1) | HUP0101344A3 (es) |
| ID (1) | ID26021A (es) |
| IL (1) | IL138827A0 (es) |
| NO (1) | NO20005148L (es) |
| NZ (1) | NZ507175A (es) |
| PE (1) | PE20000430A1 (es) |
| PL (1) | PL343487A1 (es) |
| SK (1) | SK15372000A3 (es) |
| SV (1) | SV1999000043A (es) |
| TR (1) | TR200002999T2 (es) |
| WO (1) | WO1999054300A1 (es) |
| ZA (1) | ZA200005294B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1071661A4 (en) * | 1998-04-17 | 2001-08-22 | Lilly Co Eli | METHOD FOR PRODUCING 4-HYDROXYINDOL, INDAZOL AND CARBAZOL COMPOUNDS |
| US6407261B1 (en) | 1998-04-17 | 2002-06-18 | Eli Lilly And Company | Process for preparing 4-hdyroxy indole, indazole and carbazole compounds |
| DE19962300A1 (de) * | 1999-12-23 | 2001-06-28 | Asta Medica Ag | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
| US20030225149A1 (en) * | 2002-04-30 | 2003-12-04 | Blazecka Peter G. | Process for preparing highly functionalized gamma-butyrolactams and gamma-amino acids |
| NZ624963A (en) | 2009-04-29 | 2016-07-29 | Amarin Pharmaceuticals Ie Ltd | Pharmaceutical compositions comprising epa and a cardiovascular agent and methods of using the same |
| AR088377A1 (es) | 2011-10-20 | 2014-05-28 | Siena Biotech Spa | Proceso para la preparacion de 6-cloro-2,3,4,9-tetrahidro-1h-carbazol-1-carboxamida y compuestos intermedios de esta |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY112897A (en) | 1994-04-01 | 2001-10-31 | Lilly Co Eli | Ih-indole-3-glyoxylamide spla2 inhibitors |
| EP1071661A4 (en) * | 1998-04-17 | 2001-08-22 | Lilly Co Eli | METHOD FOR PRODUCING 4-HYDROXYINDOL, INDAZOL AND CARBAZOL COMPOUNDS |
-
1999
- 1999-04-14 DZ DZ990070A patent/DZ2770A1/xx active
- 1999-04-15 US US09/647,471 patent/US6265591B1/en not_active Expired - Fee Related
- 1999-04-15 PL PL99343487A patent/PL343487A1/xx not_active Application Discontinuation
- 1999-04-15 BR BR9909697-8A patent/BR9909697A/pt not_active IP Right Cessation
- 1999-04-15 AU AU35648/99A patent/AU750368B2/en not_active Ceased
- 1999-04-15 WO PCT/US1999/008332 patent/WO1999054300A1/en not_active Application Discontinuation
- 1999-04-15 EA EA200001076A patent/EA003582B1/ru not_active IP Right Cessation
- 1999-04-15 KR KR1020007011468A patent/KR20010042741A/ko not_active Application Discontinuation
- 1999-04-15 CN CN99807248A patent/CN1305459A/zh active Pending
- 1999-04-15 EP EP99917556A patent/EP1071663A4/en not_active Withdrawn
- 1999-04-15 HU HU0101344A patent/HUP0101344A3/hu unknown
- 1999-04-15 TR TR2000/02999T patent/TR200002999T2/xx unknown
- 1999-04-15 EG EG104099D patent/EG22139A/xx active
- 1999-04-15 CA CA002326515A patent/CA2326515A1/en not_active Abandoned
- 1999-04-15 SV SV1999000043A patent/SV1999000043A/es not_active Application Discontinuation
- 1999-04-15 AR ARP990101753A patent/AR015767A1/es not_active Application Discontinuation
- 1999-04-15 JP JP2000544641A patent/JP2002512225A/ja not_active Withdrawn
- 1999-04-15 ID IDW20002058A patent/ID26021A/id unknown
- 1999-04-15 NZ NZ507175A patent/NZ507175A/xx unknown
- 1999-04-15 PE PE1999000312A patent/PE20000430A1/es not_active Application Discontinuation
- 1999-04-15 SK SK1537-2000A patent/SK15372000A3/sk unknown
- 1999-04-15 IL IL13882799A patent/IL138827A0/xx unknown
- 1999-04-16 CO CO99022895A patent/CO5080803A1/es unknown
-
2000
- 2000-09-29 ZA ZA200005294A patent/ZA200005294B/en unknown
- 2000-10-13 NO NO20005148A patent/NO20005148L/no not_active Application Discontinuation
- 2000-10-17 HR HR20000685A patent/HRP20000685A2/hr not_active Application Discontinuation
-
2002
- 2002-01-23 HK HK02100522.5A patent/HK1039120A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200005294B (en) | 2001-10-01 |
| HRP20000685A2 (en) | 2001-10-31 |
| SV1999000043A (es) | 2000-05-02 |
| CA2326515A1 (en) | 1999-10-28 |
| EG22139A (en) | 2002-08-30 |
| WO1999054300A1 (en) | 1999-10-28 |
| EA200001076A1 (ru) | 2001-04-23 |
| PE20000430A1 (es) | 2000-05-24 |
| CN1305459A (zh) | 2001-07-25 |
| PL343487A1 (en) | 2001-08-27 |
| EP1071663A1 (en) | 2001-01-31 |
| AU3564899A (en) | 1999-11-08 |
| BR9909697A (pt) | 2000-12-19 |
| NO20005148D0 (no) | 2000-10-13 |
| EA003582B1 (ru) | 2003-06-26 |
| AR015767A1 (es) | 2001-05-16 |
| AU750368B2 (en) | 2002-07-18 |
| IL138827A0 (en) | 2001-10-31 |
| TR200002999T2 (tr) | 2001-01-22 |
| KR20010042741A (ko) | 2001-05-25 |
| DZ2770A1 (fr) | 2003-12-01 |
| NO20005148L (no) | 2000-11-09 |
| EP1071663A4 (en) | 2002-06-19 |
| HUP0101344A2 (hu) | 2001-09-28 |
| NZ507175A (en) | 2002-12-20 |
| US6265591B1 (en) | 2001-07-24 |
| HUP0101344A3 (en) | 2002-12-28 |
| ID26021A (id) | 2000-11-16 |
| JP2002512225A (ja) | 2002-04-23 |
| HK1039120A1 (zh) | 2002-04-12 |
| SK15372000A3 (sk) | 2001-08-06 |
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