BR0302902A - Processo para a preparação de ácido 1- (mercaptometil) - ciclopropanoacético - Google Patents
Processo para a preparação de ácido 1- (mercaptometil) - ciclopropanoacéticoInfo
- Publication number
- BR0302902A BR0302902A BR0302902-6A BR0302902A BR0302902A BR 0302902 A BR0302902 A BR 0302902A BR 0302902 A BR0302902 A BR 0302902A BR 0302902 A BR0302902 A BR 0302902A
- Authority
- BR
- Brazil
- Prior art keywords
- mercaptomethyl
- cyclopropaneacetic acid
- acid
- amide
- preparation
- Prior art date
Links
- -1 mercaptomethyl Chemical group 0.000 title abstract 4
- 239000002253 acid Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- VFAXPOVKNPTBTM-UHFFFAOYSA-N 2-[1-(sulfanylmethyl)cyclopropyl]acetic acid Chemical compound OC(=O)CC1(CS)CC1 VFAXPOVKNPTBTM-UHFFFAOYSA-N 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- WYOMLUMUVAPMKE-UHFFFAOYSA-N 2-[1-(hydroxymethyl)cyclopropyl]acetonitrile Chemical compound N#CCC1(CO)CC1 WYOMLUMUVAPMKE-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
"PROCESSO PARA A PREPARAçãO DE áCIDO 1-(MERCAPTOMETIL)-CICLOPROPANOACéTICO". O processo da presente invenção consiste, essencialmente, de quatro etapas, a primeira etapa sendo a conversão de 1-(hidroximetil)-ciclopropanoacetonitríla para 5-oxa-spiro[2.4]hept-6-ilidenamina (também chamada no presente de "imino-éster") e sais ácidos de adição derivados, que pode ser parcialmente ou totalmente convertida para 1-(halometil)-ciclopropanoacetamida (chamada no presente de "haloamida") sob as condições da reação; os intermediários de imino-éster e haloamida não são, de preferência, isolados, mas sofrem reação in situ com a tiouréia na segunda etapa do processo para dar o intermediário inovador, a 1(carbamimidoilsulfanilmetil)-ciclopropanoacetamida, que é, de preferência, isolado na forma de um sal ácido de adição sólído e, opcionalmente, purificado antes de seguir com a reação; na terceira etapa do processo, a 1-(carbamimidoilsulfanilmetil)- ciclopropanoacetamida, ou um sal derivado, é submetida a hidrolise básica seguida de oxidação in situ para formar o dissulfeto do ácido 1-(mercaptometil)-ciclopropanoacético, um sólido que é, de preferência, isolado e purificado; na quarta e última etapa, o dissulfeto é reduzido para ácido 1 -(mercaptometil)-ciclopropanoacético.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2371048A CA2371048C (en) | 2002-02-06 | 2002-02-06 | Process for the preparation of 1-(mercaptomethyl)-cyclopropaneacetic acid |
| US10/122,541 US6512140B1 (en) | 2002-02-06 | 2002-04-15 | Process for the preparation of 1-(mercaptomethyl)-cyclopropaneacetic acid |
| PCT/CA2003/000165 WO2003066582A1 (en) | 2002-02-06 | 2003-02-05 | Process for the preparation of 1-(mercaptomethyl)-cyclopropaneacetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BR0302902A true BR0302902A (pt) | 2004-07-06 |
Family
ID=27735483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR0302902-6A BR0302902A (pt) | 2002-02-06 | 2003-02-05 | Processo para a preparação de ácido 1- (mercaptometil) - ciclopropanoacético |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1474386B1 (pt) |
| JP (1) | JP4308667B2 (pt) |
| CN (1) | CN1318400C (pt) |
| AT (1) | ATE349423T1 (pt) |
| AU (1) | AU2003244427A1 (pt) |
| BR (1) | BR0302902A (pt) |
| DE (1) | DE60310683T2 (pt) |
| WO (1) | WO2003066582A1 (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110386888A (zh) * | 2019-07-30 | 2019-10-29 | 上海红蓝医药科技有限公司 | 一种低成本、高收率的1-(巯甲基)环丙基乙酸生产工艺 |
| CN111018756A (zh) * | 2019-12-13 | 2020-04-17 | 山东益丰生化环保股份有限公司 | 一种2-2-二巯甲基-1-3-丙二硫醇的制备方法 |
| CN114181121B (zh) * | 2021-12-08 | 2024-04-26 | 江苏阿尔法药业股份有限公司 | 一种1-巯甲基环丙基乙酸的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2053209C (en) * | 1990-10-12 | 1998-12-08 | Michel L. Belley | Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists |
| CA2111372C (en) * | 1992-12-22 | 2007-01-16 | Robert N. Young | Diaryl 5,6-fusedheterocyclic acids as leukotriene antagonists |
| CA2130723C (en) * | 1993-09-03 | 2006-01-31 | Wilhelm Quittmann | Process for preparing y-mercaptocarboxylic acid derivatives |
| TW448160B (en) * | 1993-12-28 | 2001-08-01 | Merck & Co Inc | Novel dicyclohexylamine salt and process for the preparation of leukotriene antagonists |
| US5523477A (en) * | 1995-01-23 | 1996-06-04 | Merck & Co., Inc. | Process for the preparation of 1-(thiomethyl)-cyclopropaneacetic acid |
| CA2371048C (en) * | 2002-02-06 | 2011-01-04 | Delmar Chemicals Inc. | Process for the preparation of 1-(mercaptomethyl)-cyclopropaneacetic acid |
-
2003
- 2003-02-05 JP JP2003565957A patent/JP4308667B2/ja not_active Expired - Fee Related
- 2003-02-05 EP EP03737225A patent/EP1474386B1/en not_active Expired - Lifetime
- 2003-02-05 DE DE60310683T patent/DE60310683T2/de not_active Expired - Lifetime
- 2003-02-05 BR BR0302902-6A patent/BR0302902A/pt not_active Application Discontinuation
- 2003-02-05 CN CNB038033747A patent/CN1318400C/zh not_active Expired - Fee Related
- 2003-02-05 WO PCT/CA2003/000165 patent/WO2003066582A1/en not_active Ceased
- 2003-02-05 AU AU2003244427A patent/AU2003244427A1/en not_active Abandoned
- 2003-02-05 AT AT03737225T patent/ATE349423T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE349423T1 (de) | 2007-01-15 |
| JP2005517009A (ja) | 2005-06-09 |
| JP4308667B2 (ja) | 2009-08-05 |
| CN1628096A (zh) | 2005-06-15 |
| CN1318400C (zh) | 2007-05-30 |
| DE60310683T2 (de) | 2007-10-11 |
| EP1474386A1 (en) | 2004-11-10 |
| WO2003066582A1 (en) | 2003-08-14 |
| DE60310683D1 (de) | 2007-02-08 |
| AU2003244427A1 (en) | 2003-09-02 |
| EP1474386B1 (en) | 2006-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B11A | Dismissal acc. art.33 of ipl - examination not requested within 36 months of filing | ||
| B11Y | Definitive dismissal - extension of time limit for request of examination expired [chapter 11.1.1 patent gazette] |