FI92586C - Uusi stereoselektiivinen hydrausmenetelmä - Google Patents
Uusi stereoselektiivinen hydrausmenetelmä Download PDFInfo
- Publication number
- FI92586C FI92586C FI903196A FI903196A FI92586C FI 92586 C FI92586 C FI 92586C FI 903196 A FI903196 A FI 903196A FI 903196 A FI903196 A FI 903196A FI 92586 C FI92586 C FI 92586C
- Authority
- FI
- Finland
- Prior art keywords
- hydrogenation
- catalyst
- lysergol
- dihydrolysergol
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000011924 stereoselective hydrogenation Methods 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
- 238000005984 hydrogenation reaction Methods 0.000 claims description 19
- BIXJFIJYBLJTMK-UHFFFAOYSA-N Lysergol Natural products C1=CC(C2=CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-UHFFFAOYSA-N 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 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 description 14
- 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 description 12
- UFKTZIXVYHGAES-UHFFFAOYSA-N trans-dihydrolysergol Natural products C1=CC(C2CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 UFKTZIXVYHGAES-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 230000000707 stereoselective effect Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- OSKZYLPFYNARRX-UHFFFAOYSA-N methyl 7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxylate Chemical compound C1=CC(C2CC(CN(C)C2C2)C(=O)OC)=C3C2=CNC3=C1 OSKZYLPFYNARRX-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- QOTUIZVGUVLMNQ-GJLSPIEVSA-N (6aR)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR)-N-[(1S,2S,4R,7S)-2-hydroxy-5,8-dioxo-4,7-di(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR)-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide Chemical compound CC(C)[C@@H]1N2C(=O)[C@](NC(=O)C3CN(C)[C@@H]4Cc5c[nH]c6cccc(C4=C3)c56)(O[C@@]2(O)[C@@H]2CCCN2C1=O)C(C)C.CC(C)C[C@@H]1N2C(=O)[C@](NC(=O)C3CN(C)[C@@H]4Cc5c[nH]c6cccc(C4=C3)c56)(O[C@@]2(O)[C@@H]2CCCN2C1=O)C(C)C.CC(C)[C@@]1(NC(=O)C2CN(C)[C@@H]3Cc4c[nH]c5cccc(C3=C2)c45)O[C@@]2(O)[C@@H]3CCCN3C(=O)[C@H](Cc3ccccc3)N2C1=O QOTUIZVGUVLMNQ-GJLSPIEVSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 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
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 229940125722 laxative agent Drugs 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- -1 lithium aluminum hydride Chemical compound 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU893225A HU203549B (en) | 1989-06-27 | 1989-06-27 | New stereoselektive hydrogenating process for producing dihydro-lisergol |
| HU322589 | 1989-06-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI903196A0 FI903196A0 (fi) | 1990-06-26 |
| FI92586B FI92586B (fi) | 1994-08-31 |
| FI92586C true FI92586C (fi) | 1994-12-12 |
Family
ID=10963194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI903196A FI92586C (fi) | 1989-06-27 | 1990-06-26 | Uusi stereoselektiivinen hydrausmenetelmä |
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
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 |
| RU1779253C (ru) | 1992-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MM | Patent lapsed |
Owner name: RICHTER GEDEON VEGYESZETI GYOER R.T. |