GB1238348A - - Google Patents
Info
- Publication number
- GB1238348A GB1238348A GB1238348DA GB1238348A GB 1238348 A GB1238348 A GB 1238348A GB 1238348D A GB1238348D A GB 1238348DA GB 1238348 A GB1238348 A GB 1238348A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrazine
- isopropyl
- ethyl
- pyrrolo
- isobutyl
- 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- -1 benzyloxycarbonyl radical Chemical class 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- UNEBJJHVFQWTSI-UHFFFAOYSA-N 2-ethoxycarbonyl-2-phenylmethoxybutanoic acid Chemical compound C(C)OC(C(C(=O)O)(OCC1=CC=CC=C1)CC)=O UNEBJJHVFQWTSI-UHFFFAOYSA-N 0.000 abstract 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- 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 abstract 1
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical compound CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 abstract 1
- 230000000794 anti-serotonin Effects 0.000 abstract 1
- 239000003420 antiserotonin agent Substances 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- BHGHHZIMRWHYEO-UHFFFAOYSA-N diethyl 2-ethyl-2-hydroxypropanedioate Chemical compound CCOC(=O)C(O)(CC)C(=O)OCC BHGHHZIMRWHYEO-UHFFFAOYSA-N 0.000 abstract 1
- YNLVMCVYVLXNGG-UHFFFAOYSA-N diethyl 2-phenylmethoxypropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)OCC1=CC=CC=C1 YNLVMCVYVLXNGG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 abstract 1
- 230000001035 methylating effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- 230000000054 salidiuretic effect Effects 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000011877 solvent mixture Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1090067A CH520679A (de) | 1967-08-02 | 1967-08-02 | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1238348A true GB1238348A (enExample) | 1971-07-07 |
Family
ID=4368003
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1238348D Expired GB1238348A (enExample) | 1967-08-02 | 1968-07-17 | |
| GB56746/70A Expired GB1240420A (en) | 1967-08-02 | 1968-07-17 | 9,10-dihydrolysergic acid derivative |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB56746/70A Expired GB1240420A (en) | 1967-08-02 | 1968-07-17 | 9,10-dihydrolysergic acid derivative |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3652569A (enExample) |
| AT (1) | AT297008B (enExample) |
| BE (1) | BE718859A (enExample) |
| CA (1) | CA952107A (enExample) |
| CH (4) | CH520680A (enExample) |
| CY (1) | CY769A (enExample) |
| DE (1) | DE1795022C3 (enExample) |
| DK (1) | DK123482B (enExample) |
| ES (5) | ES356676A1 (enExample) |
| FI (1) | FI48274C (enExample) |
| FR (2) | FR1604602A (enExample) |
| GB (2) | GB1238348A (enExample) |
| MY (1) | MY7400292A (enExample) |
| NL (1) | NL157906B (enExample) |
| PL (2) | PL78658B1 (enExample) |
| SE (2) | SE351643B (enExample) |
| SU (1) | SU392624A3 (enExample) |
| YU (1) | YU34084B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846433A (en) * | 1969-05-06 | 1974-11-05 | Sandoz Ltd | Process for preparing ergot alkaloids |
| US4195086A (en) * | 1974-06-21 | 1980-03-25 | Sandoz Ltd. | 6-Branched chain alkyl sustituted ergot alkaloids |
| CH601321A5 (enExample) * | 1975-01-06 | 1978-07-14 | Sandoz Ag | |
| US4138565A (en) * | 1975-05-31 | 1979-02-06 | Sandoz Ltd. | Stable solutions and processes for their preparation |
| IT1157365B (it) * | 1977-10-24 | 1987-02-11 | Sandoz Ag | Medicamenti per trattare l'obesita' o ridurre il peso del corpo |
| YU41110B (en) * | 1978-07-19 | 1986-12-31 | Lek Tovarna Farmacevtskih | Process for preparing dextrorotatory ergot alcaloids acid addition salts |
| DE3303616A1 (de) * | 1982-02-12 | 1983-08-25 | Sandoz-Patent-GmbH, 7850 Lörrach | Mutterkornalkaloide, verfahren zu deren herstellung sowie diese verbindungen enthaltende pharmazeutische zubereitungen |
| DE19525137C2 (de) * | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
| SG181896A1 (en) * | 2009-12-23 | 2012-07-30 | Map Pharmaceuticals Inc | Novel ergoline analogs |
| KR20140042868A (ko) | 2011-06-23 | 2014-04-07 | 맵 파마슈티컬스, 인코포레이티드 | 신규한 플루오로에르골린 유사체 |
| EP2793580A4 (en) | 2011-12-19 | 2015-05-20 | Map Pharmaceuticals Inc | NEW DERIVATIVES OF ISO-ERGOLINE |
| AU2012355983A1 (en) | 2011-12-21 | 2015-01-22 | Map Pharmaceuticals, Inc. | Novel neuromodulatory compounds |
| US9012640B2 (en) | 2012-06-22 | 2015-04-21 | Map Pharmaceuticals, Inc. | Cabergoline derivatives |
-
1967
- 1967-08-02 CH CH1936170A patent/CH520680A/de not_active IP Right Cessation
- 1967-08-02 CH CH1936270A patent/CH520681A/de not_active IP Right Cessation
- 1967-08-02 CH CH1090067A patent/CH520679A/de not_active IP Right Cessation
- 1967-08-02 CH CH1090067A patent/CH563393A5/xx not_active IP Right Cessation
-
1968
- 1968-07-17 GB GB1238348D patent/GB1238348A/en not_active Expired
- 1968-07-17 GB GB56746/70A patent/GB1240420A/en not_active Expired
- 1968-07-23 NL NL6810435.A patent/NL157906B/xx not_active IP Right Cessation
- 1968-07-26 DK DK362968AA patent/DK123482B/da unknown
- 1968-07-26 FI FI682123A patent/FI48274C/fi active
- 1968-07-29 SE SE10291/68A patent/SE351643B/xx unknown
- 1968-07-29 SE SE7112754A patent/SE392903B/xx unknown
- 1968-07-30 DE DE1795022A patent/DE1795022C3/de not_active Expired
- 1968-07-31 PL PL1968158941A patent/PL78658B1/pl unknown
- 1968-07-31 AT AT745768A patent/AT297008B/de not_active IP Right Cessation
- 1968-07-31 PL PL1968128394A patent/PL72567B1/pl unknown
- 1968-07-31 ES ES356676A patent/ES356676A1/es not_active Expired
- 1968-07-31 BE BE718859D patent/BE718859A/xx unknown
- 1968-07-31 CA CA026,340A patent/CA952107A/en not_active Expired
- 1968-08-01 SU SU1370603A patent/SU392624A3/ru active
- 1968-08-01 YU YU1839/68A patent/YU34084B/xx unknown
- 1968-08-01 FR FR1604602D patent/FR1604602A/fr not_active Expired
- 1968-10-29 FR FR171753A patent/FR8150M/fr not_active Expired
-
1969
- 1969-09-12 ES ES371452A patent/ES371452A1/es not_active Expired
- 1969-09-12 ES ES371455A patent/ES371455A1/es not_active Expired
- 1969-09-12 ES ES371454A patent/ES371454A1/es not_active Expired
- 1969-09-12 ES ES371453A patent/ES371453A1/es not_active Expired
-
1971
- 1971-01-21 US US108641A patent/US3652569A/en not_active Expired - Lifetime
-
1974
- 1974-11-08 CY CY76974A patent/CY769A/xx unknown
- 1974-12-30 MY MY292/74A patent/MY7400292A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU392624A3 (enExample) | 1973-07-27 |
| PL72567B1 (enExample) | 1974-08-30 |
| YU34084B (en) | 1978-12-31 |
| CH520679A (de) | 1972-03-31 |
| NL157906B (nl) | 1978-09-15 |
| CH563393A5 (en) | 1975-06-30 |
| FI48274B (enExample) | 1974-04-30 |
| YU183968A (en) | 1978-06-30 |
| SE392903B (sv) | 1977-04-25 |
| FR8150M (enExample) | 1970-08-17 |
| FR1604602A (enExample) | 1972-01-03 |
| CA952107A (en) | 1974-07-30 |
| ES371452A1 (es) | 1972-03-16 |
| CH520680A (de) | 1972-03-31 |
| DK123482B (da) | 1972-06-26 |
| CH520681A (de) | 1972-03-31 |
| DE1795022C3 (de) | 1981-06-19 |
| DE1795022B2 (enExample) | 1980-08-07 |
| BE718859A (enExample) | 1969-01-31 |
| US3652569A (en) | 1972-03-28 |
| SE351643B (enExample) | 1972-12-04 |
| ES356676A1 (es) | 1970-05-01 |
| AT297008B (de) | 1972-03-10 |
| MY7400292A (en) | 1974-12-31 |
| PL78658B1 (enExample) | 1975-06-30 |
| ES371453A1 (es) | 1972-03-16 |
| NL6810435A (enExample) | 1969-02-04 |
| CY769A (en) | 1974-11-08 |
| GB1240420A (en) | 1971-07-21 |
| ES371454A1 (es) | 1972-03-16 |
| DE1795022A1 (de) | 1971-12-30 |
| ES371455A1 (es) | 1972-04-01 |
| FI48274C (fi) | 1974-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |