CO5021230A1 - PREPARATION PROCESS OF 4-SUBSTITUTE-1H-INDOL-3- GLIOXAMIDS - Google Patents
PREPARATION PROCESS OF 4-SUBSTITUTE-1H-INDOL-3- GLIOXAMIDSInfo
- Publication number
- CO5021230A1 CO5021230A1 CO99022883A CO99022883A CO5021230A1 CO 5021230 A1 CO5021230 A1 CO 5021230A1 CO 99022883 A CO99022883 A CO 99022883A CO 99022883 A CO99022883 A CO 99022883A CO 5021230 A1 CO5021230 A1 CO 5021230A1
- Authority
- CO
- Colombia
- Prior art keywords
- formula
- compound
- alkyl
- 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
Un proceso de preparación de un compuesto de la fórmula I o unasal o prodroga derivada del mismo farmacéuticamente aceptable En donde: R1 es seleccionado del grupo que consiste de alquilo C7 -C20 ; donde; R10 es seleccionado del grupo que consiste de halo, alquilo C1 -C10 , alcoxi C1 -C10 , -S-(alquil 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, 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; R4 es seleccionado del grupo que consiste de -CO2 H, -SO3 H, y -P(O)(OH)2 o una sal o prodroga derivadas del mismo; y R5 es seleccionado del grupo que consiste de hidrógeno, alquilo (C1 -C6 ), alcoxi (C1 -C6 ), halo alcoxi (C1 -C6 ), halo alquil (C2 -C6 ), bromo, cloro, flúor, yodo y arilo; proceso que comprende los siguientes pasos: a) Halogenación de un compuesto de fórmula X 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 SO2 Cl2 para formar un compuesto de fórmula IX - 2 -b) Hidrolización y descarboxilación de un compuesto de fórmula IX para formar un compuesto de fórmula VIII c) Alquilación de un compuesto de fórmula VIIcon un compuesto de fórmula VIIIpara formar un compuesto de fórmula VId) Aminación y deshidratación de un compuesto de fórmula VI con un amino de la fórmula R1 NH2 en presencia de un solvente que forma un azeótropo con agua para formar un compuesto de fórmula Ve) oxidación de un compuesto de fórmula Vpor calentamiento con una base y un reactivo sulfinante de la fórmula RSOX donde R es alquilo-(C1 -C6 ) o arilo o arilo substituido y X es alcoxi (C1 -C6 ), halo, o -OCO2 alquilo-(C1 -C6 ) para formar un compuesto de fórmula IVf) Alquilación de un compuesto de fórmula IV con un agente alquilante de la fórmula XCH2 R4a donde X es un grupo saliente y R4a es -CO2 R4b , -SO3 R4b , -P(O)(O R4b )2 , o -P(O)(O R4b )H, donde R4b es un grupo protector ácido, para formar un compuesto de fórmula IIIg) Reacción de un compuesto de fórmula IIIcon cloruro de oxalil y amoníaco para formar un compuesto de fórmula IIh) opcionalmente, hidrolización de un compuesto de fórmula IIpara formar un compuesto de fórmula I; yi) Opcionalmente, salificación de un compuesto de fórmula I.A process of preparing a compound of the formula I or a pharmaceutically acceptable compound or prodrug thereof wherein: R1 is selected from the group consisting of C7-C20 alkyl; where; R10 is selected from the group consisting of halo, C1-C10 alkyl, C1-C10 alkoxy, -S- (C1-C10 alkyl) and halo C1-C10 alkyl and t is an integer between 0 and 5 both included; R2 is selected from group consisting of hydrogen, halo, C1-C3 alkyl, C3-C4 cycloalkyl, C3-C4 cycloalkenyl, -O- (C1-C2 alkyl), -S- (C1-C2 alkyl), aryl, aryloxy, and HET, wherein HET corresponds to a heterocyclic ring that includes pyridine, pyrazine, pyrimidine, pyridazine, pyrrole, pyrazole, furan, thiophene, thiazole, isothiazole, oxadiazole, thiadiazole, imidazole, triazole and tetrazole; R4 is selected from the group consisting of -CO2 H, -SO3 H, and -P (O) (OH) 2 or a salt or prodrug derived therefrom; and R5 is selected from the group consisting of hydrogen, (C1-C6) alkyl, (C1-C6) alkoxy, halo (C1-C6) alkoxy, halo (C2-C6) alkyl, bromine, chlorine, fluorine, iodine and aryl ; process comprising the following steps: a) Halogenation of a compound of formula X wherein R8 is (C1-C6) alkyl, aryl or HET, wherein HET corresponds to a heterocyclic ring that includes pyridine, pyrazine, pyrimidine, pyridazine, pyrrole , pyrazole, furan, thiophene, thiazole, isothiazole, oxadiazole, thiadiazole, imidazole, triazole and tetrazole with SO2 Cl2 to form a compound of formula IX-2 -b) Hydrolyzing and decarboxylation of a compound of formula IX to form a compound of formula VIII c) Alkylation of a compound of formula VII with a compound of formula VIII to form a compound of formula VId) Amination and dehydration of a compound of formula VI with an amino of formula R1 NH2 in the presence of a solvent that forms an azeotrope with water to form a compound of formula Ve) oxidation of a compound of formula V by heating with a base and a sulphinating reagent of the formula RSOX where R is alkyl- (C1-C6) or aryl or sub aryl stituido and X is (C1-C6) alkoxy, halo, or -OCO2 alkyl- (C1-C6) to form a compound of formula IVf) Alkylation of a compound of formula IV with an alkylating agent of formula XCH2 R4a where X is a leaving group and R4a is -CO2 R4b, -SO3 R4b, -P (O) (O R4b) 2, or -P (O) (O R4b) H, where R4b is an acid protecting group, to form a compound of formula IIIg) Reaction of a compound of formula III with oxalyl chloride and ammonia to form a compound of formula IIh) optionally, hydrolyzing a compound of formula II to form a compound of formula I; and i) Optionally, salification of a compound of formula I.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10360498P | 1998-10-09 | 1998-10-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CO5021230A1 true CO5021230A1 (en) | 2001-03-27 |
Family
ID=22296053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CO99022883A CO5021230A1 (en) | 1998-10-09 | 1999-04-16 | PREPARATION PROCESS OF 4-SUBSTITUTE-1H-INDOL-3- GLIOXAMIDS |
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 |
| DK0675110T3 (en) * | 1994-04-01 | 2002-10-07 | Lilly Co Eli | 1H-indole-3-glyoxylamide sPLA2 inhibitors |
| CA2279211A1 (en) * | 1997-02-20 | 1998-08-27 | Shionogi & Co., Ltd. | Indole dicarboxylic acid derivatives |
-
1999
- 1999-04-14 DZ DZ990071A patent/DZ2771A1/en active
- 1999-04-15 JP JP2000575838A patent/JP2002527421A/en not_active Withdrawn
- 1999-04-15 SV SV1999000042A patent/SV1999000042A/en not_active Application Discontinuation
- 1999-04-15 AR ARP990101752A patent/AR015766A1/en unknown
- 1999-04-15 AU AU35644/99A patent/AU3564499A/en not_active Abandoned
- 1999-04-15 TW TW088106024A patent/TW472041B/en active
- 1999-04-15 WO PCT/US1999/008325 patent/WO2000021929A1/en not_active Application Discontinuation
- 1999-04-15 EP EP99917552A patent/EP1119549A4/en not_active Withdrawn
- 1999-04-15 PE PE1999000311A patent/PE20000429A1/en not_active Application Discontinuation
- 1999-04-15 CA CA002347718A patent/CA2347718A1/en not_active Abandoned
- 1999-04-16 CO CO99022883A patent/CO5021230A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1119549A4 (en) | 2003-01-29 |
| TW472041B (en) | 2002-01-11 |
| AU3564499A (en) | 2000-05-01 |
| PE20000429A1 (en) | 2000-05-23 |
| JP2002527421A (en) | 2002-08-27 |
| CA2347718A1 (en) | 2000-04-20 |
| EP1119549A1 (en) | 2001-08-01 |
| DZ2771A1 (en) | 2003-12-01 |
| WO2000021929A1 (en) | 2000-04-20 |
| AR015766A1 (en) | 2001-05-16 |
| SV1999000042A (en) | 2000-04-11 |
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