AR015766A1 - Procedimiento para preparar compuestos de 1-h-indol-3-glioxamidas-4-sustituidas, sales farmaceuticamente aceptables de los mismos y derivados prodroga dedichos compuestos. - Google Patents
Procedimiento para preparar compuestos de 1-h-indol-3-glioxamidas-4-sustituidas, sales farmaceuticamente aceptables de los mismos y derivados prodroga dedichos compuestos.Info
- Publication number
- AR015766A1 AR015766A1 ARP990101752A ARP990101752A AR015766A1 AR 015766 A1 AR015766 A1 AR 015766A1 AR P990101752 A ARP990101752 A AR P990101752A AR P990101752 A ARP990101752 A AR P990101752A AR 015766 A1 AR015766 A1 AR 015766A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compounds
- alkyl
- halo
- aryl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 22
- 238000000034 method Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000005843 halogen group Chemical group 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052740 iodine Inorganic materials 0.000 abstract 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 102000005473 Secretory Phospholipases A2 Human genes 0.000 abstract 1
- 108010031873 Secretory Phospholipases A2 Proteins 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000000651 prodrug Chemical class 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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 trata de un procedimiento para preparar compuestos de 1H-indol-3-glioxamidas utiles para inhibir SPLA2 de formula I donde R1 es seleccionado entre el grupo formado por alquilo C7-20, en donde R10 se selecciona entre halo, alquilo C1-10, alcoxi C1-10, -S-alquilo C1-10, y haloalquilo C1-10, y t es un entero de0 a 5 ambos inclusive; R2 se selecciona entre el hidrogeno, halo, alquilo C1-3, cicloalquilo C3-4, cicloalquenilo C3-4, -O(alquilo C1-2), -S(alquilo C1-2),arilo, ariloxi y Het. R4 se selecciona entre -CO2H, -SO2H, y -P(O)(OH)2 o sal o derivados de prodroga de los mismos; R5 se selecciona entre hidrogeno,-alquilo C1-6, alcoxi C1-6, halo (alcoxi C1-6), halo(alquilo C1-6), bromo, cloro, fluoro, yodo y arilo; caracterizado porque comprende las etapas de (a)halogenar un compuesto de formula X donde R8 es alquilo C1-6, arilo o Het, con SO2Cl2 para formar un compuesto de formula IX; b) hidrolizar y descarboxilar uncompuesto de la formula IX para formar compuestos de formula VIII; c)alquilar los compuestos de formula VII con compuestos de formula VIII; para formar loscompuestos de formula VI; d)aminar y deshidratar los compuestos de formula VI con aminas de formula R1NH2 en presencia de solventes que forman azeotropos conel agua para formar compuestos de formula V; e)oxidar los compuestos de formula V por calentamiento con una base y un compuesto de formula RSOX, donde R esalquilo C1-6, arilo, o arilo sustituido y X es alcoxi C1-6, halo o -OCO2 alquilo C1-6 para formar compuestos de formula IV, f) alquilar los compuestos deformula IV con agentes de alquilacion de formula XCH2R4a donde X es un grupo saliente y R4a es -CO2R4a, -SO3R4b, -P(O)(OR4b)2, o -P(O)(OR4b)H, donde R4b es ungrupo ácido protector, para formar compuestos de formula III; g)hacer reaccionar los compuestos de formula III con cloruro de oxalilo y amoníaco para formarlos compuestos de formula II; h) opcionalmente hidrolizar los compuestos de formula II para formar los compuestos de la formula I, e i)opcionalmente salificarde los compuestos de formula I obtenidos. Dichos compuestos son utilizados para inhibir la liberacion mediada por sPLA2 de ácidos grasos en estados tales
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10360498P | 1998-10-09 | 1998-10-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR015766A1 true AR015766A1 (es) | 2001-05-16 |
Family
ID=22296053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP990101752A AR015766A1 (es) | 1998-10-09 | 1999-04-15 | Procedimiento para preparar compuestos de 1-h-indol-3-glioxamidas-4-sustituidas, sales farmaceuticamente aceptables de los mismos y derivados prodroga dedichos compuestos. |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1119549A4 (es) |
| JP (1) | JP2002527421A (es) |
| AR (1) | AR015766A1 (es) |
| AU (1) | AU3564499A (es) |
| CA (1) | CA2347718A1 (es) |
| CO (1) | CO5021230A1 (es) |
| DZ (1) | DZ2771A1 (es) |
| PE (1) | PE20000429A1 (es) |
| SV (1) | SV1999000042A (es) |
| TW (1) | TW472041B (es) |
| WO (1) | WO2000021929A1 (es) |
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 (ja) * | 1983-08-02 | 1985-02-19 | Sagami Chem Res Center | ４−ヒドロキシインド−ル誘導体の製造方法 |
| SI0675110T1 (en) * | 1994-04-01 | 2002-12-31 | Eli Lilly And Company | 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/xx active
- 1999-04-15 CA CA002347718A patent/CA2347718A1/en not_active Abandoned
- 1999-04-15 EP EP99917552A patent/EP1119549A4/en not_active Withdrawn
- 1999-04-15 AR ARP990101752A patent/AR015766A1/es unknown
- 1999-04-15 WO PCT/US1999/008325 patent/WO2000021929A1/en not_active Ceased
- 1999-04-15 TW TW088106024A patent/TW472041B/zh active
- 1999-04-15 PE PE1999000311A patent/PE20000429A1/es not_active Application Discontinuation
- 1999-04-15 AU AU35644/99A patent/AU3564499A/en not_active Abandoned
- 1999-04-15 SV SV1999000042A patent/SV1999000042A/es not_active Application Discontinuation
- 1999-04-15 JP JP2000575838A patent/JP2002527421A/ja not_active Withdrawn
- 1999-04-16 CO CO99022883A patent/CO5021230A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU3564499A (en) | 2000-05-01 |
| EP1119549A4 (en) | 2003-01-29 |
| EP1119549A1 (en) | 2001-08-01 |
| WO2000021929A1 (en) | 2000-04-20 |
| CO5021230A1 (es) | 2001-03-27 |
| JP2002527421A (ja) | 2002-08-27 |
| DZ2771A1 (fr) | 2003-12-01 |
| TW472041B (en) | 2002-01-11 |
| SV1999000042A (es) | 2000-04-11 |
| PE20000429A1 (es) | 2000-05-23 |
| CA2347718A1 (en) | 2000-04-20 |
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