ES2085497T3 - Procedimiento para la preparacion del acido 1,2,3,4-tetrahidroisoquinolin-3-carboxilico racemico y opticamente activo, asi como de sus precursores. - Google Patents
Procedimiento para la preparacion del acido 1,2,3,4-tetrahidroisoquinolin-3-carboxilico racemico y opticamente activo, asi como de sus precursores.Info
- Publication number
- ES2085497T3 ES2085497T3 ES92100996T ES92100996T ES2085497T3 ES 2085497 T3 ES2085497 T3 ES 2085497T3 ES 92100996 T ES92100996 T ES 92100996T ES 92100996 T ES92100996 T ES 92100996T ES 2085497 T3 ES2085497 T3 ES 2085497T3
- Authority
- ES
- Spain
- Prior art keywords
- acid
- sub
- tetrahydroisokinoline
- organic
- organic acid
- 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 - Lifetime
Links
- 239000002253 acid Substances 0.000 title abstract 8
- 238000000034 method Methods 0.000 title abstract 2
- 239000002243 precursor Substances 0.000 title 1
- 230000001131 transforming effect Effects 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 238000007127 saponification reaction Methods 0.000 abstract 2
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 abstract 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- 241001282138 Antigonia capros Species 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
SE DESCRIBE UN PROCEDIMIENTO PARA FABRICAR 3-ACIDO ORGANICO DE 1, 2, 3, 4 -TETRAHIDROISOQUINOLINA, RACEMICO Y OPTICAMENTE ACTIVO, SEGUN EL CUAL SE CICLIZAN EN AMBIENTE BASICO DIHALO-O-XILILENOS CON DIALQUILESTERES DE ACIDO N-ACILAMIDOMALONICO DE LA FORMULA (CO SUB 2 R ELEVADO 1) SUB 2 CHNHCOR (AL CUADRADO) , EN LA CUAL SIGNIFICAN R ELEVADO 1 (C SUB 1-C SUB 4)-ALQUILO Y R (AL CUADRADO) H, (C SUB 1-C SUB 4)-ALQUILO O (C SUB 6-C SUB 12)-ARILO, A ESTERES DE ACIDO DICARBOXILICO, DESCARBOXILANDOLOS MEDIANTE SAPONIFICACION BASICA Y EL SUBSIGUIENTE TRATAMIENTO ACIDO Y TRANSFORMANDOLOS POSTERIORMENTE EN AMBIENTE ACIDO EN 3-ACIDO ORGANICO DE (D, L)-1, 2, 3, 4 -TETRAHIDROISOQUINOLINA. O BIEN SE CICLIZAN, EN AMBIENTE BASICO, DIHALO-O -XILILENOS EN ESTERES DE ACIDO DICARBOXILICO, TRANSFORMANDOLOS DIRECTAMENTE, SIN AISLAMIENTO Y POR PROCEDIMIENTO DE RECIPIENTE UNICO, EN 3-ACIDO ORGANICO DE (D, L)-1, 2, 3, 4-TETRAHIDROISOQUINOLINA, Y, DADO EL CASO, SOMETIENDO A REACCION EL 3-ACIDO ORGANICO RACEMICO DE 1,2, 3, 4 -TETRAHIDROISOQUINOLINA CON (-)-METANOL Y CON ACIDO P-TOLUOLSULFONICO, TRANSFORMANDOLO EN (-)-MENTILESTER DE 3-ACIDO ORGANICO DE (D) O (L)-1, 2, 3, 4-TETRAHIDROISOQUINOLINA, SEPARANDO A CONTINUACION CROMATOGRAFICAMENTE POR COLUMNAS, LOS DIAESTEREOMEROS QUE SE SAPONIFICAN BASICAMENTE EN 3-ACIDO ORGANICO DE (D) O (L)-1, 2, 3, 4 -TETRAHIDROISOQUINOLINA, O ESTERIZANDO EL 3-ACIDO ORGANICO DE (D, L)-1, 2 , 3, 4-TETRAHIDROISOQUINOLINA MEDIANTE ALCOHOL BENCILICO O ACIDO P-TOLUOLSULFONICO; TRANSFORMANDOLO CON D(-)-ACIDO MANDELICO EN (D)-MANDELATO DE ESTER BENCILICO DE 3-ACIDO ORGANICO DE (D)-1, 2, 3, 4 -TETRAHIDROISOQUINOLINA Y EN (D)-MANDELATO DE ESTER BENCILICO DE 3-ACIDO ORGANICO DE (L)-1, 2, 3, 4-TETRAHIDROISOQUINOLINA O TRANSFORMANDOLO CON L(+)-ACIDO MANDELICO EN (L)-MANDELATO DE ESTER BENCILICO DE 3-ACIDO ORGANICO DE (D)-1, 2, 3, 4-TETRAHIDROISOQUINOLINA Y EN (L)-MANDELATO DE ESTER BENCILICO DE 3-ACIDO ORGANICO DE (L)-1, 2, 3, 4 -TETRAHIDROISOQUINOLINA. A CONTINUACION, LOS COMPUESTOS OBTENIDOS SE SEPARAN EN LAS ANTIPODAS OPTICAS MEDIANTE CRISTALIZACION FRACCIONADA EN UN DISOLVENTE INERTE, LIBERANDO MEDIANTE SAPONIFICACION BASICA LOS ENATIOMEROS DEL 3-ACIDO ORGANICO DE (D) O DE (L)-1, 2, 3, 4 -TETRAHIDROISOQUINOLINA, RECUPERANDOSE EL REACTIVO AUXILIAR QUIRAL.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4102017 | 1991-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2085497T3 true ES2085497T3 (es) | 1996-06-01 |
Family
ID=6423604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES92100996T Expired - Lifetime ES2085497T3 (es) | 1991-01-24 | 1992-01-22 | Procedimiento para la preparacion del acido 1,2,3,4-tetrahidroisoquinolin-3-carboxilico racemico y opticamente activo, asi como de sus precursores. |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5252738A (es) |
| EP (1) | EP0496369B1 (es) |
| JP (1) | JP3187905B2 (es) |
| KR (1) | KR100225829B1 (es) |
| AR (1) | AR247554A1 (es) |
| AT (1) | ATE136299T1 (es) |
| AU (1) | AU645654B2 (es) |
| CA (1) | CA2059908C (es) |
| DE (1) | DE59205884D1 (es) |
| DK (1) | DK0496369T3 (es) |
| ES (1) | ES2085497T3 (es) |
| FI (1) | FI101963B1 (es) |
| GR (1) | GR3019556T3 (es) |
| HU (1) | HU213273B (es) |
| IE (1) | IE74136B1 (es) |
| MX (1) | MX9200288A (es) |
| NO (1) | NO178763C (es) |
| TW (1) | TW224454B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW224454B (es) * | 1991-01-24 | 1994-06-01 | Hoechst Ag | |
| GB2266529A (en) * | 1992-05-01 | 1993-11-03 | Merck Sharp & Dohme | Tetrahydroisoquinoline derivatives |
| WO1997017050A2 (en) * | 1995-11-09 | 1997-05-15 | Monsanto Company | An improved method for preparation of substituted tetrahydroisoquinolines |
| DE10320197A1 (de) * | 2002-12-20 | 2004-07-08 | Degussa Ag | Umhüllte Persauerstoffverbindungen mit kontrollierter Freisetzung, Verfahren zu ihrer Herstellung und ihrer Verwendung |
| FR3007751A1 (fr) | 2013-06-28 | 2015-01-02 | Solvay | Melanges de sels de sodium et de leur utilisation |
| CN111254180B (zh) * | 2018-11-30 | 2023-04-28 | 浙江大学 | 一种酶法拆分制备(s)-1,2,3,4-四氢异喹啉-3-甲酸的方法 |
| CN111254170B (zh) * | 2018-11-30 | 2023-04-28 | 浙江大学 | 一种多酶耦合制备(s)-1,2,3,4-四氢异喹啉-3-甲酸的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5187290A (en) * | 1985-03-22 | 1993-02-16 | E. R. Squibb & Sons, Inc. | Acylaminoalkanoyl urethanes or thiourethanes |
| US4912221A (en) * | 1988-10-27 | 1990-03-27 | Occidental Chemical Corporation | Chiral 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and precursors and preparation thereof |
| TW224454B (es) * | 1991-01-24 | 1994-06-01 | Hoechst Ag | |
| US5236934A (en) * | 1992-08-26 | 1993-08-17 | E. I. Du Pont De Nemours And Company | 1,2,3,4-tetrahydroisoquinolines useful in the treatment of CNS disorders |
-
1991
- 1991-08-13 TW TW080106363A patent/TW224454B/zh not_active IP Right Cessation
-
1992
- 1992-01-21 US US07/822,930 patent/US5252738A/en not_active Expired - Lifetime
- 1992-01-22 ES ES92100996T patent/ES2085497T3/es not_active Expired - Lifetime
- 1992-01-22 AT AT92100996T patent/ATE136299T1/de not_active IP Right Cessation
- 1992-01-22 DE DE59205884T patent/DE59205884D1/de not_active Expired - Lifetime
- 1992-01-22 EP EP92100996A patent/EP0496369B1/de not_active Expired - Lifetime
- 1992-01-22 AR AR92321665A patent/AR247554A1/es active
- 1992-01-22 FI FI920269A patent/FI101963B1/fi active
- 1992-01-22 DK DK92100996.5T patent/DK0496369T3/da active
- 1992-01-23 NO NO920313A patent/NO178763C/no not_active IP Right Cessation
- 1992-01-23 KR KR1019920000894A patent/KR100225829B1/ko not_active Expired - Lifetime
- 1992-01-23 MX MX9200288A patent/MX9200288A/es unknown
- 1992-01-23 JP JP00982592A patent/JP3187905B2/ja not_active Expired - Lifetime
- 1992-01-23 IE IE920207A patent/IE74136B1/en not_active IP Right Cessation
- 1992-01-23 AU AU10394/92A patent/AU645654B2/en not_active Expired
- 1992-01-23 CA CA002059908A patent/CA2059908C/en not_active Expired - Lifetime
- 1992-01-24 HU HU9200231A patent/HU213273B/hu unknown
-
1993
- 1993-06-15 US US08/076,772 patent/US5359074A/en not_active Expired - Lifetime
-
1996
- 1996-04-04 GR GR960400851T patent/GR3019556T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2059908A1 (en) | 1992-07-25 |
| HU9200231D0 (en) | 1992-04-28 |
| DK0496369T3 (da) | 1996-07-29 |
| IE74136B1 (en) | 1997-07-02 |
| JP3187905B2 (ja) | 2001-07-16 |
| TW224454B (es) | 1994-06-01 |
| FI101963B (fi) | 1998-09-30 |
| HU213273B (en) | 1997-04-28 |
| CA2059908C (en) | 2002-09-10 |
| MX9200288A (es) | 1992-07-01 |
| FI101963B1 (fi) | 1998-09-30 |
| KR100225829B1 (ko) | 1999-10-15 |
| EP0496369A1 (de) | 1992-07-29 |
| DE59205884D1 (de) | 1996-05-09 |
| NO920313L (no) | 1992-07-27 |
| NO920313D0 (no) | 1992-01-23 |
| KR920014782A (ko) | 1992-08-25 |
| FI920269A7 (fi) | 1992-07-25 |
| NO178763C (no) | 1996-05-29 |
| US5359074A (en) | 1994-10-25 |
| IE920207A1 (en) | 1992-07-29 |
| AU1039492A (en) | 1992-07-30 |
| GR3019556T3 (en) | 1996-07-31 |
| AU645654B2 (en) | 1994-01-20 |
| AR247554A1 (es) | 1995-01-31 |
| NO178763B (no) | 1996-02-19 |
| ATE136299T1 (de) | 1996-04-15 |
| JPH04334370A (ja) | 1992-11-20 |
| HUT63835A (en) | 1993-10-28 |
| FI920269A0 (fi) | 1992-01-22 |
| EP0496369B1 (de) | 1996-04-03 |
| US5252738A (en) | 1993-10-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
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