ES8505988A1 - Sorbinil prepn. by optical resolution with amino:pinane derivs. - Google Patents
Sorbinil prepn. by optical resolution with amino:pinane derivs.Info
- Publication number
- ES8505988A1 ES8505988A1 ES534921A ES534921A ES8505988A1 ES 8505988 A1 ES8505988 A1 ES 8505988A1 ES 534921 A ES534921 A ES 534921A ES 534921 A ES534921 A ES 534921A ES 8505988 A1 ES8505988 A1 ES 8505988A1
- Authority
- ES
- Spain
- Prior art keywords
- salt
- sorbinil
- pinane
- soln
- iia
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Prepn. of sorbinil (I), or its pharmaceutically acceptable cationic salt, comprises (i) crystallising the (-)-3-aminomethyl pinane salt (IIa) of (I) from a soln. of racemic hydantoin of formula (III), and (ii) converting (IIa) to (I) or its salt. Alternatively, (a) either the (+)-3-aminomethyl pinane salt (IIb) or the (-)-2-amino-2-norpinane salt (IV) of the enantiomer of sorbinil is crystallised from a soln. of the racemic hydantoin of formula (III), (b) a concentrate of sorbinil is isolated from the mother liquor, (c) the quinine salt (V) of (I) is crystallised from a soln. of the concentrate and (d) the quinine salt is converted to (I) or its salt. Also claimed are chiral amine salts of (I), i.e. (IIa), (IIb), (IV) and (V). (I) is a potent aldose reductase inhibitor, esp. useful in controlling the chronic complications of diabetes mellitus. Process gives good yields with much lower solvent vols., and avoids the use of a highly toxic resolving agent (brucine). The efficacy of the process is further enhanced by isolating and recycling the undesired enantiomer via 6-fluoro-4-chromanone.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44068682A | 1982-11-10 | 1982-11-10 | |
| US06/440,641 US4435578A (en) | 1982-11-10 | 1982-11-10 | Sorbinil by optical resolution of precursor 6-fluoro-4-ureidochroman-4-carboxylic acid |
| US06/440,657 US4431828A (en) | 1982-11-10 | 1982-11-10 | Regeneration of 6-fluoro-4-chromanone from by-products in the synthesis of sorbinil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES534921A0 ES534921A0 (en) | 1985-06-16 |
| ES8505988A1 true ES8505988A1 (en) | 1985-06-16 |
Family
ID=27412063
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES527118A Expired ES8506040A1 (en) | 1982-11-10 | 1983-11-08 | Sorbinil prepn. by optical resolution with amino:pinane derivs. |
| ES534921A Expired ES8505988A1 (en) | 1982-11-10 | 1984-08-06 | Sorbinil prepn. by optical resolution with amino:pinane derivs. |
| ES534920A Expired ES8600269A1 (en) | 1982-11-10 | 1984-08-06 | Sorbinil prepn. by optical resolution with amino:pinane derivs. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES527118A Expired ES8506040A1 (en) | 1982-11-10 | 1983-11-08 | Sorbinil prepn. by optical resolution with amino:pinane derivs. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES534920A Expired ES8600269A1 (en) | 1982-11-10 | 1984-08-06 | Sorbinil prepn. by optical resolution with amino:pinane derivs. |
Country Status (16)
| Country | Link |
|---|---|
| KR (1) | KR870000867B1 (en) |
| AU (1) | AU540399B2 (en) |
| BG (1) | BG44206A3 (en) |
| CS (1) | CS266560B2 (en) |
| DD (1) | DD213924A5 (en) |
| DK (1) | DK512683A (en) |
| ES (3) | ES8506040A1 (en) |
| FI (1) | FI77247C (en) |
| GR (1) | GR79017B (en) |
| IL (2) | IL70165A (en) |
| NO (1) | NO161916C (en) |
| NZ (1) | NZ206189A (en) |
| PL (1) | PL139713B1 (en) |
| PT (1) | PT77617B (en) |
| SU (1) | SU1209030A3 (en) |
| YU (2) | YU44867B (en) |
-
1983
- 1983-11-07 YU YU2203/83A patent/YU44867B/en unknown
- 1983-11-07 PT PT77617A patent/PT77617B/en not_active IP Right Cessation
- 1983-11-07 GR GR72904A patent/GR79017B/el unknown
- 1983-11-08 PL PL1983244460A patent/PL139713B1/en unknown
- 1983-11-08 FI FI834088A patent/FI77247C/en not_active IP Right Cessation
- 1983-11-08 KR KR1019830005294A patent/KR870000867B1/en not_active IP Right Cessation
- 1983-11-08 IL IL70165A patent/IL70165A/en unknown
- 1983-11-08 DD DD83256455A patent/DD213924A5/en not_active IP Right Cessation
- 1983-11-08 NZ NZ206189A patent/NZ206189A/en unknown
- 1983-11-08 ES ES527118A patent/ES8506040A1/en not_active Expired
- 1983-11-09 CS CS838271A patent/CS266560B2/en unknown
- 1983-11-09 DK DK512683A patent/DK512683A/en not_active Application Discontinuation
- 1983-11-09 AU AU21105/83A patent/AU540399B2/en not_active Ceased
- 1983-11-09 BG BG8362988A patent/BG44206A3/en unknown
- 1983-11-09 NO NO834086A patent/NO161916C/en unknown
- 1983-11-09 SU SU833659625A patent/SU1209030A3/en active
-
1984
- 1984-08-06 ES ES534921A patent/ES8505988A1/en not_active Expired
- 1984-08-06 ES ES534920A patent/ES8600269A1/en not_active Expired
-
1985
- 1985-09-09 YU YU1409/85A patent/YU43883B/en unknown
-
1987
- 1987-02-23 IL IL81648A patent/IL81648A0/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES534920A0 (en) | 1985-09-16 |
| AU2110583A (en) | 1984-05-17 |
| FI834088A0 (en) | 1983-11-08 |
| ES527118A0 (en) | 1985-06-16 |
| CS827183A2 (en) | 1989-04-14 |
| KR870000867B1 (en) | 1987-04-30 |
| SU1209030A3 (en) | 1986-01-30 |
| NO161916B (en) | 1989-07-03 |
| PL139713B1 (en) | 1987-02-28 |
| ES8506040A1 (en) | 1985-06-16 |
| ES534921A0 (en) | 1985-06-16 |
| DK512683A (en) | 1984-05-11 |
| NZ206189A (en) | 1987-06-30 |
| PT77617A (en) | 1983-12-01 |
| PL244460A1 (en) | 1985-03-26 |
| FI834088A (en) | 1984-05-11 |
| KR840006806A (en) | 1984-12-03 |
| NO161916C (en) | 1989-10-11 |
| DD213924A5 (en) | 1984-09-26 |
| GR79017B (en) | 1984-10-02 |
| YU140985A (en) | 1986-04-30 |
| YU43883B (en) | 1989-12-31 |
| NO834086L (en) | 1984-05-11 |
| BG44206A3 (en) | 1988-10-14 |
| DK512683D0 (en) | 1983-11-09 |
| ES8600269A1 (en) | 1985-09-16 |
| IL81648A0 (en) | 1987-09-16 |
| AU540399B2 (en) | 1984-11-15 |
| FI77247B (en) | 1988-10-31 |
| PT77617B (en) | 1986-05-12 |
| CS266560B2 (en) | 1990-01-12 |
| FI77247C (en) | 1989-02-10 |
| YU220383A (en) | 1988-02-29 |
| IL70165A (en) | 1987-12-20 |
| YU44867B (en) | 1991-04-30 |
| IL70165A0 (en) | 1984-02-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19970203 |