CS212760B2 - Method of preparing ergot alkaloids - Google Patents
Method of preparing ergot alkaloids Download PDFInfo
- Publication number
- CS212760B2 CS212760B2 CS782524A CS252478A CS212760B2 CS 212760 B2 CS212760 B2 CS 212760B2 CS 782524 A CS782524 A CS 782524A CS 252478 A CS252478 A CS 252478A CS 212760 B2 CS212760 B2 CS 212760B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- amino acid
- atcc
- phenylalanine
- halogen
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 229960003133 ergot alkaloid Drugs 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 235000001014 amino acid Nutrition 0.000 claims description 26
- 150000001413 amino acids Chemical class 0.000 claims description 26
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical class OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 16
- 238000000855 fermentation Methods 0.000 claims description 16
- 230000004151 fermentation Effects 0.000 claims description 16
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 16
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical group CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 15
- 229910052736 halogen Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 10
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 4
- CNMAQBJBWQQZFZ-LURJTMIESA-N (2s)-2-(pyridin-2-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=CC=N1 CNMAQBJBWQQZFZ-LURJTMIESA-N 0.000 claims description 3
- VOWKMMDXKYIBPG-YFKPBYRVSA-N (2s)-2-amino-3-(1h-pyrazol-5-yl)propanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=NN1 VOWKMMDXKYIBPG-YFKPBYRVSA-N 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 3
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 3
- -1 furylalanine Chemical compound 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000003471 mutagenic agent Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
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- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 claims description 2
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- TYYYSRHHJOVPKV-RXMQYKEDSA-N (2r)-2-amino-2-hydroxy-3-methylbutanoic acid Chemical compound CC(C)[C@@](N)(O)C(O)=O TYYYSRHHJOVPKV-RXMQYKEDSA-N 0.000 description 2
- ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 2
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- LIMAOLZSWRJOMG-HJPBWRTMSA-N dihydroergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C(C)C)C1=CC=CC=C1 LIMAOLZSWRJOMG-HJPBWRTMSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/182—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system
- C12P17/183—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system containing an indolo[4,3-F,G]quinoleine nucleus, e.g. compound containing the lysergic acid nucleus as well as the dimeric ergot nucleus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Public Health (AREA)
- Veterinary Medicine (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16096/77A GB1584464A (en) | 1977-04-19 | 1977-04-19 | Ergot alkaloids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS212760B2 true CS212760B2 (en) | 1982-03-26 |
Family
ID=10071128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS782524A CS212760B2 (en) | 1977-04-19 | 1978-04-19 | Method of preparing ergot alkaloids |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4230854A (de) |
| JP (1) | JPS53132599A (de) |
| AT (1) | AT369783B (de) |
| BE (1) | BE865921A (de) |
| CA (1) | CA1113410A (de) |
| CH (1) | CH637658A5 (de) |
| CS (1) | CS212760B2 (de) |
| DE (1) | DE2816773A1 (de) |
| DK (1) | DK145701C (de) |
| FR (1) | FR2387989A1 (de) |
| GB (1) | GB1584464A (de) |
| HU (1) | HU175173B (de) |
| IE (1) | IE46797B1 (de) |
| NL (1) | NL7804174A (de) |
| SE (1) | SE7804362L (de) |
| SU (1) | SU735154A3 (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH646166A5 (it) * | 1980-09-30 | 1984-11-15 | Linnea Sa | Procedimento di sintesi parziale della vincamina e di alcaloidi indolici correlati. |
| FR2499589B1 (fr) * | 1981-02-06 | 1985-11-15 | Richter Gedeon Vegyeszet | Procede pour regler la quantite et les proportions des alcaloides qui se forment lors de la fermentation |
| US4390625A (en) | 1981-02-06 | 1983-06-28 | Richter Gedeon Vegyeszeti Gyar Rt | Method for controlling the amount and distribution of alkaloids formed in a fermentation process |
| CH649300A5 (de) * | 1981-08-07 | 1985-05-15 | Sandoz Ag | Ergopeptinderivate, ihre herstellung und verwendung. |
| HU190141B (en) * | 1983-08-10 | 1986-08-28 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | New process for production of clavin-type rye-smut alcaloids |
| US5891885A (en) * | 1996-10-09 | 1999-04-06 | Algos Pharmaceutical Corporation | Method for treating migraine |
| EP2515654A4 (de) * | 2009-12-23 | 2013-04-24 | Map Pharmaceuticals Inc | Neue ergolinanaloga |
| MX2013015373A (es) | 2011-06-23 | 2014-02-11 | Map Pharmaceuticals Inc | Nuevos analogos de fluoroergolina. |
| CA2859173A1 (en) | 2011-12-19 | 2013-06-27 | Map Pharmaceuticals, Inc. | Novel iso-ergoline derivatives |
| US8946420B2 (en) | 2011-12-21 | 2015-02-03 | Map Pharmaceuticals, Inc. | Neuromodulatory compounds |
| US9012640B2 (en) | 2012-06-22 | 2015-04-21 | Map Pharmaceuticals, Inc. | Cabergoline derivatives |
| EP3941904A1 (de) | 2020-06-12 | 2022-01-26 | Beckley Psytech Limited | Pharmazeutische zusammensetzung mit 5-methoxyn,n-dimethyltryptamin |
| WO2022153266A1 (en) | 2021-01-15 | 2022-07-21 | Beckley Psytech Limited | Ergoline analogues |
| GB202212116D0 (en) | 2022-08-19 | 2022-10-05 | Beckley Psytech Ltd | Pharmaceutically acceptable salts and Compositions thereof |
| US12264131B2 (en) | 2022-08-19 | 2025-04-01 | Beckley Psytech Limited | Pharmaceutically acceptable salts and compositions thereof |
| US12246005B2 (en) | 2023-06-13 | 2025-03-11 | Beckley Psytech Limited | 5-methoxy-n,n-dimethyltryptamine (5-MeO-DMT) formulations |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH508628A (de) * | 1968-06-25 | 1971-06-15 | Sandoz Ag | Verfahren zur Herstellung neuer heterocyclischer Verbindungen |
| CH534683A (de) * | 1970-05-26 | 1973-03-15 | Sandoz Ag | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
| FI56386C (fi) * | 1973-07-09 | 1980-01-10 | Sandoz Ag | Foerfarande foer framstaellning av oktahydro-oxazolo(3,2-a)pyrrolo(2,1-c)pyrazin-derivat |
| HU172649B (hu) * | 1975-04-24 | 1978-11-28 | Gyogyszerkutato Intezet | Sposob poluchenija novykh biologicheski aktivnykh lizergamidov |
| CH619468A5 (de) * | 1976-01-12 | 1980-09-30 | Sandoz Ag | |
| US4124712A (en) * | 1976-09-06 | 1978-11-07 | Sandoz Ltd. | Ergot peptide alkaloid derivatives |
-
1977
- 1977-04-19 GB GB16096/77A patent/GB1584464A/en not_active Expired
-
1978
- 1978-03-21 US US05/888,750 patent/US4230854A/en not_active Expired - Lifetime
- 1978-03-21 CH CH307778A patent/CH637658A5/it not_active IP Right Cessation
- 1978-04-12 BE BE186745A patent/BE865921A/xx not_active IP Right Cessation
- 1978-04-12 FR FR7810745A patent/FR2387989A1/fr active Granted
- 1978-04-13 AT AT0260378A patent/AT369783B/de active
- 1978-04-17 JP JP4578678A patent/JPS53132599A/ja active Pending
- 1978-04-17 DK DK165778A patent/DK145701C/da not_active IP Right Cessation
- 1978-04-18 SE SE7804362A patent/SE7804362L/xx unknown
- 1978-04-18 SU SU782606999A patent/SU735154A3/ru active
- 1978-04-18 IE IE759/78A patent/IE46797B1/en unknown
- 1978-04-18 HU HU78SO1215A patent/HU175173B/hu unknown
- 1978-04-18 DE DE19782816773 patent/DE2816773A1/de not_active Withdrawn
- 1978-04-18 CA CA301,413A patent/CA1113410A/en not_active Expired
- 1978-04-19 CS CS782524A patent/CS212760B2/cs unknown
- 1978-04-19 NL NL7804174A patent/NL7804174A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53132599A (en) | 1978-11-18 |
| DK145701C (da) | 1983-07-18 |
| FR2387989B1 (de) | 1980-07-04 |
| DK165778A (da) | 1978-10-20 |
| GB1584464A (en) | 1981-02-11 |
| CH637658A5 (it) | 1983-08-15 |
| SU735154A3 (ru) | 1980-05-15 |
| HU175173B (hu) | 1980-05-28 |
| IE780759L (en) | 1978-10-19 |
| DE2816773A1 (de) | 1978-10-26 |
| ATA260378A (de) | 1982-06-15 |
| FR2387989A1 (fr) | 1978-11-17 |
| CA1113410A (en) | 1981-12-01 |
| SE7804362L (sv) | 1978-10-20 |
| IE46797B1 (en) | 1983-09-21 |
| BE865921A (fr) | 1978-07-31 |
| NL7804174A (nl) | 1978-10-23 |
| AT369783B (de) | 1983-01-25 |
| US4230854A (en) | 1980-10-28 |
| DK145701B (da) | 1983-01-31 |
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