RU1779253C - Способ получени дигидролизергола - Google Patents
Способ получени дигидролизерголаInfo
- Publication number
- RU1779253C RU1779253C SU904830539A SU4830539A RU1779253C RU 1779253 C RU1779253 C RU 1779253C SU 904830539 A SU904830539 A SU 904830539A SU 4830539 A SU4830539 A SU 4830539A RU 1779253 C RU1779253 C RU 1779253C
- Authority
- RU
- Russia
- Prior art keywords
- hydrogenation
- pyridine
- mixture
- catalyst
- producing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 7
- BIXJFIJYBLJTMK-UHFFFAOYSA-N Lysergol Natural products C1=CC(C2=CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-UHFFFAOYSA-N 0.000 claims abstract description 6
- UFKTZIXVYHGAES-WDBKCZKBSA-N [(6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]methanol Chemical compound C1=CC([C@H]2C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 UFKTZIXVYHGAES-WDBKCZKBSA-N 0.000 claims abstract description 6
- BIXJFIJYBLJTMK-MEBBXXQBSA-N lysergol Chemical compound C1=CC(C2=C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-MEBBXXQBSA-N 0.000 claims abstract description 6
- UFKTZIXVYHGAES-UHFFFAOYSA-N trans-dihydrolysergol Natural products C1=CC(C2CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 UFKTZIXVYHGAES-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 3
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000011924 stereoselective hydrogenation Methods 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU893225A HU203549B (en) | 1989-06-27 | 1989-06-27 | New stereoselektive hydrogenating process for producing dihydro-lisergol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU1779253C true RU1779253C (ru) | 1992-11-30 |
Family
ID=10963194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU904830539A RU1779253C (ru) | 1989-06-27 | 1990-06-27 | Способ получени дигидролизергола |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5097031A (online.php) |
| JP (1) | JPH03128374A (online.php) |
| CA (1) | CA2019407C (online.php) |
| CH (1) | CH680445A5 (online.php) |
| CZ (1) | CZ281957B6 (online.php) |
| DD (1) | DD295378A5 (online.php) |
| DE (1) | DE4020475A1 (online.php) |
| FI (1) | FI92586C (online.php) |
| FR (1) | FR2648815B1 (online.php) |
| HU (1) | HU203549B (online.php) |
| IT (1) | IT1249001B (online.php) |
| NL (1) | NL9001459A (online.php) |
| RU (1) | RU1779253C (online.php) |
| YU (1) | YU124790A (online.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ530007A (en) | 2001-06-08 | 2006-02-24 | Sod Conseils Rech Applic | Somatostatin-dopamine chimeric analogues that retain both somatostatin and dopamine activity in vivo and display enhanced biological activity |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE107647T1 (de) * | 1984-04-09 | 1994-07-15 | Schering Ag | 2-substituierte ergolin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel. |
| CH658058A5 (en) * | 1984-06-21 | 1986-10-15 | Linnea Sa | Process for preparing lumilysergol derivatives |
-
1989
- 1989-06-27 HU HU893225A patent/HU203549B/hu not_active IP Right Cessation
-
1990
- 1990-06-20 CA CA002019407A patent/CA2019407C/en not_active Expired - Fee Related
- 1990-06-21 FR FR909007757A patent/FR2648815B1/fr not_active Expired - Lifetime
- 1990-06-22 US US07/542,168 patent/US5097031A/en not_active Expired - Lifetime
- 1990-06-26 YU YU01247/90A patent/YU124790A/xx unknown
- 1990-06-26 DD DD90342087A patent/DD295378A5/de not_active IP Right Cessation
- 1990-06-26 IT IT02076990A patent/IT1249001B/it active IP Right Grant
- 1990-06-26 JP JP2165835A patent/JPH03128374A/ja active Pending
- 1990-06-26 CH CH2131/90A patent/CH680445A5/de not_active IP Right Cessation
- 1990-06-26 NL NL9001459A patent/NL9001459A/nl not_active Application Discontinuation
- 1990-06-26 FI FI903196A patent/FI92586C/fi not_active IP Right Cessation
- 1990-06-27 DE DE4020475A patent/DE4020475A1/de not_active Withdrawn
- 1990-06-27 RU SU904830539A patent/RU1779253C/ru active
- 1990-06-27 CZ CS903211A patent/CZ281957B6/cs not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| E.Eichund Mitarb Planta Med, 1986, 290. I.BIol, Chem 10§, 595, 1935 I.BIoi Chem Щ, 117 1936. Патент HU N° 174577. кл С 07 D 467/02, 1984. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ281957B6 (cs) | 1997-04-16 |
| FI92586B (fi) | 1994-08-31 |
| YU124790A (en) | 1991-10-31 |
| FI903196A0 (fi) | 1990-06-26 |
| DD295378A5 (de) | 1991-10-31 |
| NL9001459A (nl) | 1991-01-16 |
| FR2648815A1 (fr) | 1990-12-28 |
| DE4020475A1 (de) | 1991-02-07 |
| CH680445A5 (online.php) | 1992-08-31 |
| CA2019407A1 (en) | 1990-12-27 |
| US5097031A (en) | 1992-03-17 |
| CA2019407C (en) | 1997-09-30 |
| IT9020769A1 (it) | 1991-12-26 |
| IT9020769A0 (it) | 1990-06-26 |
| FR2648815B1 (fr) | 1992-08-14 |
| JPH03128374A (ja) | 1991-05-31 |
| HU203549B (en) | 1991-08-28 |
| IT1249001B (it) | 1995-02-11 |
| CZ321190A3 (en) | 1997-01-15 |
| FI92586C (fi) | 1994-12-12 |
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