HUP9902043A2 - Process for the preparation of [s-(r*,r*)]-3-methyl-2-(3-oxo-3h-benzo[d]isothiazol-2-yl)pentanoic acid and [s-(r*,r*)], l-2-(2-(2-(1-carboxy-2-methylbutylcarbamoyl)phenyldisulfonyl)benzoyl-amino)-3-methylpentanoic acid - Google Patents
Process for the preparation of [s-(r*,r*)]-3-methyl-2-(3-oxo-3h-benzo[d]isothiazol-2-yl)pentanoic acid and [s-(r*,r*)], l-2-(2-(2-(1-carboxy-2-methylbutylcarbamoyl)phenyldisulfonyl)benzoyl-amino)-3-methylpentanoic acidInfo
- Publication number
- HUP9902043A2 HUP9902043A2 HU9902043A HUP9902043A HUP9902043A2 HU P9902043 A2 HUP9902043 A2 HU P9902043A2 HU 9902043 A HU9902043 A HU 9902043A HU P9902043 A HUP9902043 A HU P9902043A HU P9902043 A2 HUP9902043 A2 HU P9902043A2
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- oxo
- acid
- isothiazol
- carboxy
- Prior art date
Links
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- LBEMXJWGHIEXRA-UHFFFAOYSA-N 2-[(2-carboxyphenyl)disulfanyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(O)=O LBEMXJWGHIEXRA-UHFFFAOYSA-N 0.000 abstract 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 abstract 1
- 229930182844 L-isoleucine Natural products 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229960000310 isoleucine Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
A találmány tárgya eljárás az[S-(R*,R*)]-3-metil-2-(3-őxő-3H-benző[d]izőitazől-2-il)-pentánsav előállítására. A találmány szerintiúgy járnak el, hőgy 2,2'-ditiő-szalicilsavat halőgénező szerrelreagáltatnak, majd a kapőtt 2,2'-ditiő-bisz-benzőil-halőgenidettetrahidrőfűránban vagy tethahidrőfűrán és valamely bázis elegyében L-izőleűcinnal reagáltatják, majd a kapőtt[S-(R*,R*)],L-2-(2-[2-(1-karbőxi-2-metil-bűtil-karbamő- il)-fenil-diszűlfőnil]-benziől-aminő)-3-metil-pentánsavat reagáltatják halőgénőxidáló reagenssel, és így[S-(R*,R*]-3-metil-2-(3-őxő-3H-benző[d]zőtiazől-2-il)-pentánsavatállítanak elő. A találmány szerinti eljárással nyert vegyületgyógyszerészetben alkalmazható. ŕThe subject of the invention is a process for the preparation of [S-(R*,R*)]-3-methyl-2-(3-oxo-3H-benz[d]isoyl-2-yl)-pentanoic acid. According to the invention, they proceed as follows: 2,2'-dithiosalicylic acid is reacted with a halogenizing agent, then the obtained 2,2'-dithio-bis-benzoylhalogenide is reacted with L-isoleucine in a mixture of tetrahydrofuran or tetrahydrofuran and a base, and then the obtained [S- (R*,R*)],L-2-(2-[2-(1-Carboxy-2-methyl-butyl-carbamoyl)-phenyl-disulfonyl]-benzylamino)-3-methylpentanoic acid are reacted with a halogen oxidizing reagent and thus [S-(R*,R*]-3-methyl-2-(3-oxo-3H-benz[d]isothiazol-2-yl)-pentanoic acid is produced. applicable
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US874595P | 1995-12-15 | 1995-12-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP9902043A2 true HUP9902043A2 (en) | 1999-11-29 |
| HUP9902043A3 HUP9902043A3 (en) | 2000-03-28 |
Family
ID=21733413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9902043A HUP9902043A3 (en) | 1995-12-15 | 1996-11-27 | Process for the preparation of [s-(r |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0874835A1 (en) |
| JP (1) | JP2000505067A (en) |
| KR (1) | KR20000064403A (en) |
| CN (1) | CN1208407A (en) |
| AU (1) | AU1083597A (en) |
| BG (1) | BG102470A (en) |
| BR (1) | BR9612020A (en) |
| CA (1) | CA2233553A1 (en) |
| CZ (1) | CZ182498A3 (en) |
| HU (1) | HUP9902043A3 (en) |
| IL (1) | IL123903A0 (en) |
| NO (1) | NO982709D0 (en) |
| NZ (1) | NZ323803A (en) |
| PL (1) | PL327135A1 (en) |
| SK (1) | SK81798A3 (en) |
| WO (1) | WO1997022598A1 (en) |
| ZA (1) | ZA9610479B (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9304903D0 (en) * | 1993-03-10 | 1993-04-28 | Zeneca Ltd | Compounds,preparation and use |
| US5734081A (en) * | 1994-08-05 | 1998-03-31 | Warner-Lambert Company | Arylthio compounds |
| US5463122A (en) * | 1994-08-05 | 1995-10-31 | Warner-Lambert Company | Arylthio compounds |
-
1996
- 1996-11-27 EP EP96940880A patent/EP0874835A1/en not_active Withdrawn
- 1996-11-27 WO PCT/US1996/018929 patent/WO1997022598A1/en not_active Application Discontinuation
- 1996-11-27 BR BR9612020A patent/BR9612020A/en not_active Application Discontinuation
- 1996-11-27 CN CN96199009A patent/CN1208407A/en active Pending
- 1996-11-27 HU HU9902043A patent/HUP9902043A3/en unknown
- 1996-11-27 KR KR1019980704461A patent/KR20000064403A/en not_active Application Discontinuation
- 1996-11-27 CZ CZ981824A patent/CZ182498A3/en unknown
- 1996-11-27 JP JP9522815A patent/JP2000505067A/en active Pending
- 1996-11-27 PL PL96327135A patent/PL327135A1/en unknown
- 1996-11-27 CA CA002233553A patent/CA2233553A1/en not_active Abandoned
- 1996-11-27 SK SK817-98A patent/SK81798A3/en unknown
- 1996-11-27 AU AU10835/97A patent/AU1083597A/en not_active Abandoned
- 1996-11-27 NZ NZ323803A patent/NZ323803A/en unknown
- 1996-11-27 IL IL12390396A patent/IL123903A0/en unknown
- 1996-12-12 ZA ZA9610479A patent/ZA9610479B/en unknown
-
1998
- 1998-05-20 BG BG102470A patent/BG102470A/en unknown
- 1998-06-12 NO NO982709A patent/NO982709D0/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1997022598A1 (en) | 1997-06-26 |
| NO982709L (en) | 1998-06-12 |
| NZ323803A (en) | 1999-02-25 |
| JP2000505067A (en) | 2000-04-25 |
| PL327135A1 (en) | 1998-11-23 |
| NO982709D0 (en) | 1998-06-12 |
| CN1208407A (en) | 1999-02-17 |
| HUP9902043A3 (en) | 2000-03-28 |
| BR9612020A (en) | 1999-06-29 |
| CA2233553A1 (en) | 1997-06-26 |
| IL123903A0 (en) | 1998-10-30 |
| AU1083597A (en) | 1997-07-14 |
| CZ182498A3 (en) | 1998-09-16 |
| SK81798A3 (en) | 1998-11-04 |
| KR20000064403A (en) | 2000-11-06 |
| EP0874835A1 (en) | 1998-11-04 |
| BG102470A (en) | 1999-08-31 |
| ZA9610479B (en) | 1998-06-09 |
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