PE20000429A1 - PROCESS TO PREPARE 4-SUBSTITUTED-1H-INDOL-3-GLIOXAMIDES - Google Patents
PROCESS TO PREPARE 4-SUBSTITUTED-1H-INDOL-3-GLIOXAMIDESInfo
- Publication number
- PE20000429A1 PE20000429A1 PE1999000311A PE00031199A PE20000429A1 PE 20000429 A1 PE20000429 A1 PE 20000429A1 PE 1999000311 A PE1999000311 A PE 1999000311A PE 00031199 A PE00031199 A PE 00031199A PE 20000429 A1 PE20000429 A1 PE 20000429A1
- Authority
- PE
- Peru
- Prior art keywords
- alkyl
- compound
- alcoxy
- halo
- group
- 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
- C07D209/10—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
-
- 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
-
- 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)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
SE REFIERE A UN PROCEDIMIENTO PARA PREPARAR 1H-INDOL-3-GLIOXAMIDAS DE FORMULA I, DONDE R1 ES ALQUILO C7-C20, GRUPO a, b, c; R10 ES HALO, ALQUILO C1-C10, ALCOXI C1-C10, ENTRE OTROS; t ES 0-5; R2 ES H, HALO, ALQUILO C1-C3, ENTRE OTROS; R4 ES -CO2H, -SO3H, PO(OH)2; R5 ES H, ALQUILO C1-C6, ALCOXI C1-C6, ENTRE OTROS; QUE COMPRENDE a)HALOGENAR R8-O-C(=O)-CH2-C(0O)-R2, R8 ES ALQUILO C1-C6, ARILO, HET CON SO2Cl2 Y FORMAR R8-O-C(=O)-CH(Cl)-C(=O)-R2; LUEGO HIDROLIZAR Y DESCARBOXILAR PARA FORMAR Cl-CH2-C(=O)-R2; LUEGO ALQUILAR UN COMPUESTO VII CON Cl-CH2-C(=O)-R2, PARA FORMAR UN COMPUESTO VI; LUEGO AMINAR Y DESHIDRATAR CON UNA AMINA R1NH2, EN UN SOLVENTE QUE FORMA UN AZEOTROPO CON AGUA PARA FORMAR UN COMPUESTO V; LUEGO OXIDAR CALENTANDO CON UNA BASE Y RSOX, R ES ALQUILO C1-C6, ARILO, X ES ALCOXI C1-C6, HALO, -OCO2(ALQUILO C1-C6) PARA FORMAR UN COMPUESTO IV; LUEGO ALQUILAR CON UN AGENTE ALQUILIZANTE XCH2R4a; X ES UN GRUPO SALIENTE; R4a ES -CO2R4b, -SO3R4b, -PO(OR4b)2, -PO(OR4b)H; R4b ES UN ACIDO PROTECTOR PARA FORMAR UN GRUPO III; LUEGO REACCIONAR CON CLORURO DE OXALILO Y AMONIACO PARA FORMAR UN COMPUESTO II; LUEGO HIDROLIZAR FORMAR COMPUESTO I Y OPCIONALMENTE SALIFICAR. EL COMPUESTO I PUEDE SER UTIL PARA INHIBIR LA LIBERACION DE ACIDOS GRASOS OCASIONADA POR sPLA2 Y TRATAR SHOCK SEPTICO, SINDROME DE DIFICULTAD RESPIRATORIA DEL ADULTOREFERS TO A PROCEDURE FOR PREPARING 1H-INDOL-3-GLYOXAMIDES OF FORMULA I, WHERE R1 IS C7-C20 ALKYL, GROUP a, b, c; R10 IS HALO, C1-C10 ALKYL, C1-C10 ALCOXY, AMONG OTHERS; t IS 0-5; R2 IS H, HALO, C1-C3 ALKYL, AMONG OTHERS; R4 IS -CO2H, -SO3H, PO (OH) 2; R5 IS H, C1-C6 ALKYL, C1-C6 ALCOXY, AMONG OTHERS; WHICH INCLUDES a) HALOGENATE R8-OC (= O) -CH2-C (0O) -R2, R8 IS C1-C6 ALKYL, ARYL, HET WITH SO2Cl2 AND FORM R8-OC (= O) -CH (Cl) -C (= O) -R2; THEN HYDROLIZE AND DECARBOXYLATE TO FORM Cl-CH2-C (= O) -R2; THEN RENT A COMPOUND VII WITH Cl-CH2-C (= O) -R2, TO FORM A COMPOUND VI; THEN AMINATE AND DEHYDRATE WITH AN AMINE R1NH2, IN A SOLVENT THAT FORMS AN AZEOTROPE WITH WATER TO FORM A COMPOUND V; THEN OXIDIZE BY HEATING WITH A BASE AND RSOX, R IS C1-C6 ALKYL, ARYL, X IS C1-C6 ALCOXY, HALO, -OCO2 (C1-C6 ALKYL) TO FORM A COMPOUND IV; THEN RENT WITH A RENTAL AGENT XCH2R4a; X IS AN OUTGOING GROUP; R4a IS -CO2R4b, -SO3R4b, -PO (OR4b) 2, -PO (OR4b) H; R4b IS A PROTECTIVE ACID TO FORM A GROUP III; THEN REACT WITH OXALYL AND AMMONIA CHLORIDE TO FORM A COMPOUND II; THEN HYDROLIZE FORM COMPOUND I AND OPTIONALLY SALIFY. COMPOUND I MAY BE USEFUL TO INHIBIT THE RELEASE OF FATTY ACIDS CAUSED BY sPLA2 AND TO TREAT SEPTIC SHOCK, RESPIRATORY DIFFICULTY SYNDROME, ADULT
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10360498P | 1998-10-09 | 1998-10-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
PE20000429A1 true PE20000429A1 (en) | 2000-05-23 |
Family
ID=22296053
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PE1999000311A PE20000429A1 (en) | 1998-10-09 | 1999-04-15 | PROCESS TO PREPARE 4-SUBSTITUTED-1H-INDOL-3-GLIOXAMIDES |
Country Status (11)
Country | Link |
---|---|
EP (1) | EP1119549A4 (en) |
JP (1) | JP2002527421A (en) |
AR (1) | AR015766A1 (en) |
AU (1) | AU3564499A (en) |
CA (1) | CA2347718A1 (en) |
CO (1) | CO5021230A1 (en) |
DZ (1) | DZ2771A1 (en) |
PE (1) | PE20000429A1 (en) |
SV (1) | SV1999000042A (en) |
TW (1) | TW472041B (en) |
WO (1) | WO2000021929A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AUPQ876400A0 (en) * | 2000-07-14 | 2000-08-03 | University Of Queensland, The | Compositions and method of using them |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6032769A (en) * | 1983-08-02 | 1985-02-19 | Sagami Chem Res Center | Preparation of 4-hydroxyindole derivative |
HUT72048A (en) * | 1994-04-01 | 1996-03-28 | Lilly Co Eli | 1h-indole-3-glyoxylamide spla2 inhibitors and pharmaceutical compositions containing these compounds |
AU6229298A (en) * | 1997-02-20 | 1998-09-09 | Shionogi & Co., Ltd. | Indole dicarboxylic acid derivatives |
-
1999
- 1999-04-14 DZ DZ990071A patent/DZ2771A1/en active
- 1999-04-15 CA CA002347718A patent/CA2347718A1/en not_active Abandoned
- 1999-04-15 PE PE1999000311A patent/PE20000429A1/en not_active Application Discontinuation
- 1999-04-15 SV SV1999000042A patent/SV1999000042A/en not_active Application Discontinuation
- 1999-04-15 AR ARP990101752A patent/AR015766A1/en unknown
- 1999-04-15 TW TW088106024A patent/TW472041B/en active
- 1999-04-15 EP EP99917552A patent/EP1119549A4/en not_active Withdrawn
- 1999-04-15 JP JP2000575838A patent/JP2002527421A/en not_active Withdrawn
- 1999-04-15 AU AU35644/99A patent/AU3564499A/en not_active Abandoned
- 1999-04-15 WO PCT/US1999/008325 patent/WO2000021929A1/en not_active Application Discontinuation
- 1999-04-16 CO CO99022883A patent/CO5021230A1/en unknown
Also Published As
Publication number | Publication date |
---|---|
EP1119549A4 (en) | 2003-01-29 |
AU3564499A (en) | 2000-05-01 |
JP2002527421A (en) | 2002-08-27 |
TW472041B (en) | 2002-01-11 |
EP1119549A1 (en) | 2001-08-01 |
DZ2771A1 (en) | 2003-12-01 |
WO2000021929A1 (en) | 2000-04-20 |
CO5021230A1 (en) | 2001-03-27 |
SV1999000042A (en) | 2000-04-11 |
AR015766A1 (en) | 2001-05-16 |
CA2347718A1 (en) | 2000-04-20 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FG | Grant, registration | ||
FD | Application declared void or lapsed |