BRPI0417769B8 - método sintético para a aquilação redutiva na posição c-3 de indóis - Google Patents
método sintético para a aquilação redutiva na posição c-3 de indóisInfo
- Publication number
- BRPI0417769B8 BRPI0417769B8 BRPI0417769A BRPI0417769A BRPI0417769B8 BR PI0417769 B8 BRPI0417769 B8 BR PI0417769B8 BR PI0417769 A BRPI0417769 A BR PI0417769A BR PI0417769 A BRPI0417769 A BR PI0417769A BR PI0417769 B8 BRPI0417769 B8 BR PI0417769B8
- Authority
- BR
- Brazil
- Prior art keywords
- indoles
- reductive alkylation
- synthetic method
- alkylation
- indole
- Prior art date
Links
- 150000002475 indoles Chemical group 0.000 title abstract 3
- 238000005932 reductive alkylation reaction Methods 0.000 title abstract 3
- 238000010189 synthetic method Methods 0.000 title 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- 239000002841 Lewis acid Substances 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- -1 indole compound Chemical class 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 229910052990 silicon hydride Inorganic materials 0.000 abstract 1
- 125000001424 substituent group Chemical group 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
metodologia sintética para a aquilação redutiva na posição c-3 de indóis. a presente invenção refere-se a um processo para a alquilação redutiva na posição c-3 de um composto de indol em que o indol é tratado com um aldeído na presença de um ácido de lewis e um agente de redução de hidreto de silício. o processo é útil para a alquilação na posição c-3 dos indóis que contêm substituintes sensíveis a ácido na posição n-1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52979703P | 2003-12-16 | 2003-12-16 | |
| PCT/US2004/041989 WO2005058820A1 (en) | 2003-12-16 | 2004-12-15 | A synthetic methodology for the reductive alkylation at the c-3 position of indoles |
| US11/014,657 US7282594B2 (en) | 2003-12-16 | 2004-12-16 | Synthetic methodology for the reductive alkylation at the C-3 position of indoles |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| BRPI0417769A BRPI0417769A (pt) | 2007-04-17 |
| BRPI0417769A8 BRPI0417769A8 (pt) | 2018-05-08 |
| BRPI0417769B1 BRPI0417769B1 (pt) | 2019-12-17 |
| BRPI0417769B8 true BRPI0417769B8 (pt) | 2021-05-25 |
Family
ID=34700047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0417769A BRPI0417769B8 (pt) | 2003-12-16 | 2004-12-15 | método sintético para a aquilação redutiva na posição c-3 de indóis |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7282594B2 (pt) |
| EP (1) | EP1697320B1 (pt) |
| JP (1) | JP5121232B2 (pt) |
| KR (2) | KR20120082477A (pt) |
| CN (1) | CN1914170B (pt) |
| AR (1) | AR046895A1 (pt) |
| AU (1) | AU2004299462B2 (pt) |
| BR (1) | BRPI0417769B8 (pt) |
| CA (1) | CA2549120C (pt) |
| CR (1) | CR8446A (pt) |
| EC (1) | ECSP066648A (pt) |
| EG (1) | EG24473A (pt) |
| GT (1) | GT200400266A (pt) |
| HN (1) | HN2004000536A (pt) |
| IL (1) | IL176147A (pt) |
| MX (1) | MXPA06006669A (pt) |
| NI (1) | NI200600132A (pt) |
| NO (1) | NO20062757L (pt) |
| PA (1) | PA8620101A1 (pt) |
| PE (1) | PE20051012A1 (pt) |
| RU (1) | RU2352560C2 (pt) |
| SG (1) | SG147487A1 (pt) |
| TW (1) | TW200526576A (pt) |
| UA (1) | UA84445C2 (pt) |
| WO (1) | WO2005058820A1 (pt) |
| ZA (1) | ZA200604966B (pt) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7605156B2 (en) | 2001-12-03 | 2009-10-20 | Wyeth | Methods for the use of inhibitors of cytosolic phospholipase A2 |
| US7713964B2 (en) | 2001-12-03 | 2010-05-11 | Wyeth Llc | Methods for treating asthmatic conditions |
| TW200510305A (en) | 2003-07-25 | 2005-03-16 | Wyeth Corp | Process for the preparation of CPLA2 inhibitors |
| US7582771B2 (en) * | 2003-09-03 | 2009-09-01 | Wyeth | Process for the synthesis of cPLA2 inhibitors |
| US7342119B2 (en) * | 2003-09-30 | 2008-03-11 | Wyeth Holdings Corporation | Process for the synthesis of a CPLA2 inhibitor |
| AR053410A1 (es) * | 2004-08-19 | 2007-05-09 | Wyeth Corp | Proceso para la sintesis de indoles n-alquilados c-2, c-3 sustituidos. compuestos intermediarios |
| GT200600228A (es) * | 2005-05-27 | 2006-12-26 | Inhibidores de la fosfolipasa a2 citosolica | |
| TW200826932A (en) * | 2006-10-31 | 2008-07-01 | Wyeth Corp | Semi-solid formulations of phospholipase enzyme inhibitors |
| EP2104498A2 (en) * | 2006-10-31 | 2009-09-30 | Wyeth | Liquid formulations of phospholipase enzyme inhibitors |
| CN111087340B (zh) * | 2019-11-29 | 2021-12-07 | 上海应用技术大学 | 一种维拉佐酮中间体的制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9317764D0 (en) * | 1993-08-26 | 1993-10-13 | Pfizer Ltd | Therapeutic compound |
| GB9609641D0 (en) * | 1996-05-09 | 1996-07-10 | Pfizer Ltd | Compounds useful in therapy |
| US6797708B2 (en) | 2001-12-03 | 2004-09-28 | Wyeth | Inhibitors of cytosolic phospholipase A2 |
| US7101875B2 (en) | 2001-12-03 | 2006-09-05 | Wyeth | Methods for treating arthritic disorders |
| US7605156B2 (en) | 2001-12-03 | 2009-10-20 | Wyeth | Methods for the use of inhibitors of cytosolic phospholipase A2 |
| US6984735B2 (en) | 2001-12-03 | 2006-01-10 | Wyeth | Process for making an aldehyde |
| US6635771B2 (en) | 2001-12-03 | 2003-10-21 | Wyeth | N-benzhydryl indole compounds |
| TWI334778B (en) * | 2001-12-03 | 2010-12-21 | Wyeth Corp | Inhibitors of cytosolic phospholipase a2 |
| US7713964B2 (en) | 2001-12-03 | 2010-05-11 | Wyeth Llc | Methods for treating asthmatic conditions |
| US20040182785A1 (en) * | 2002-10-23 | 2004-09-23 | Rigel Technology Corporation | Animal plasma process by precipitation |
| TW200510305A (en) | 2003-07-25 | 2005-03-16 | Wyeth Corp | Process for the preparation of CPLA2 inhibitors |
| US7582771B2 (en) | 2003-09-03 | 2009-09-01 | Wyeth | Process for the synthesis of cPLA2 inhibitors |
| US7342119B2 (en) * | 2003-09-30 | 2008-03-11 | Wyeth Holdings Corporation | Process for the synthesis of a CPLA2 inhibitor |
| AR053410A1 (es) | 2004-08-19 | 2007-05-09 | Wyeth Corp | Proceso para la sintesis de indoles n-alquilados c-2, c-3 sustituidos. compuestos intermediarios |
| GT200600228A (es) | 2005-05-27 | 2006-12-26 | Inhibidores de la fosfolipasa a2 citosolica |
-
2004
- 2004-12-05 HN HN2004000536A patent/HN2004000536A/es unknown
- 2004-12-10 PE PE2004001237A patent/PE20051012A1/es not_active Application Discontinuation
- 2004-12-14 GT GT200400266A patent/GT200400266A/es unknown
- 2004-12-15 EP EP04814200.4A patent/EP1697320B1/en active Active
- 2004-12-15 JP JP2006545820A patent/JP5121232B2/ja not_active Expired - Fee Related
- 2004-12-15 TW TW093138860A patent/TW200526576A/zh unknown
- 2004-12-15 RU RU2006125447/04A patent/RU2352560C2/ru active
- 2004-12-15 NI NI200600132A patent/NI200600132A/es unknown
- 2004-12-15 MX MXPA06006669A patent/MXPA06006669A/es active IP Right Grant
- 2004-12-15 AU AU2004299462A patent/AU2004299462B2/en not_active Ceased
- 2004-12-15 SG SG200808109-3A patent/SG147487A1/en unknown
- 2004-12-15 UA UAA200607900A patent/UA84445C2/ru unknown
- 2004-12-15 KR KR1020127016929A patent/KR20120082477A/ko not_active Application Discontinuation
- 2004-12-15 CN CN2004800416736A patent/CN1914170B/zh active Active
- 2004-12-15 WO PCT/US2004/041989 patent/WO2005058820A1/en active Application Filing
- 2004-12-15 BR BRPI0417769A patent/BRPI0417769B8/pt not_active IP Right Cessation
- 2004-12-15 KR KR1020067014252A patent/KR101194592B1/ko active IP Right Grant
- 2004-12-15 PA PA20048620101A patent/PA8620101A1/es unknown
- 2004-12-15 CA CA2549120A patent/CA2549120C/en active Active
- 2004-12-15 AR ARP040104672A patent/AR046895A1/es unknown
- 2004-12-16 US US11/014,657 patent/US7282594B2/en active Active
-
2006
- 2006-06-06 IL IL176147A patent/IL176147A/en active IP Right Grant
- 2006-06-08 CR CR8446A patent/CR8446A/es not_active Application Discontinuation
- 2006-06-13 NO NO20062757A patent/NO20062757L/no not_active Application Discontinuation
- 2006-06-14 EG EGNA2006000557 patent/EG24473A/xx active
- 2006-06-15 ZA ZA2006/04966A patent/ZA200604966B/en unknown
- 2006-06-16 EC EC2006006648A patent/ECSP066648A/es unknown
-
2007
- 2007-10-15 US US11/872,193 patent/US7709661B2/en active Active
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Owner name: WYETH (US) Free format text: A FIM DE ATENDER A TRANSFERENCIA, REQUERIDA ATRAVES DA PETICAO NO 20130073204/RJ DE 30/08/2013, E NECESSARIO ESCLARECER A DIVERGENCIA ENTRE O NOME DO TITULAR DO PEDIDO E O NOME DA EMPRESA QUE CONSTA NO DOCUMENTO DE CESSAO. |
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| B25D | Requested change of name of applicant approved |
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| B25A | Requested transfer of rights approved |
Owner name: ZIARCO INC (US) |
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| B07D | Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette] | ||
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