SU976851A3 - Способ получени D-6- @ -пропил-8 L-метил /меркапто или оксо/ метилэрголина или его солей - Google Patents
Способ получени D-6- @ -пропил-8 L-метил /меркапто или оксо/ метилэрголина или его солей Download PDFInfo
- Publication number
- SU976851A3 SU976851A3 SU802984351A SU2984351A SU976851A3 SU 976851 A3 SU976851 A3 SU 976851A3 SU 802984351 A SU802984351 A SU 802984351A SU 2984351 A SU2984351 A SU 2984351A SU 976851 A3 SU976851 A3 SU 976851A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- propyl
- ergoline
- mixture
- combined
- methoxycarbonyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 8
- 150000003839 salts Chemical class 0.000 title claims abstract 8
- ZYACKOKSHZQYDS-NTVGDFDMSA-N (6ar,10ar)-9-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)C)C2)=C3C2=CNC3=C1 ZYACKOKSHZQYDS-NTVGDFDMSA-N 0.000 title 1
- 125000003396 thiol group Chemical class [H]S* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 102000003946 Prolactin Human genes 0.000 claims abstract 10
- 108010057464 Prolactin Proteins 0.000 claims abstract 10
- 229940097325 prolactin Drugs 0.000 claims abstract 10
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract 6
- 206010034010 Parkinsonism Diseases 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 159000000000 sodium salts Chemical class 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- -1 methoxycarbonyl ergoline Chemical compound 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 15
- 241000700159 Rattus Species 0.000 claims 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 12
- 239000011541 reaction mixture Substances 0.000 claims 11
- 239000000243 solution Substances 0.000 claims 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 10
- 239000002904 solvent Substances 0.000 claims 9
- 239000011780 sodium chloride Substances 0.000 claims 8
- 238000004809 thin layer chromatography Methods 0.000 claims 8
- 238000001704 evaporation Methods 0.000 claims 7
- 230000008020 evaporation Effects 0.000 claims 7
- 239000000284 extract Substances 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 6
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical compound O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 claims 5
- 230000008018 melting Effects 0.000 claims 5
- 238000002844 melting Methods 0.000 claims 5
- 238000002360 preparation method Methods 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 4
- 239000002024 ethyl acetate extract Substances 0.000 claims 4
- 230000005764 inhibitory process Effects 0.000 claims 4
- 239000000047 product Substances 0.000 claims 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000000908 ammonium hydroxide Substances 0.000 claims 3
- 239000000706 filtrate Substances 0.000 claims 3
- 239000010410 layer Substances 0.000 claims 3
- 239000000463 material Substances 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 229960000583 acetic acid Drugs 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003480 eluent Substances 0.000 claims 2
- 239000012362 glacial acetic acid Substances 0.000 claims 2
- 238000002347 injection Methods 0.000 claims 2
- 239000007924 injection Substances 0.000 claims 2
- 238000007918 intramuscular administration Methods 0.000 claims 2
- 238000001990 intravenous administration Methods 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 2
- XHXXWWGGXFUMAJ-UHFFFAOYSA-N methanethiol;sodium Chemical compound [Na].SC XHXXWWGGXFUMAJ-UHFFFAOYSA-N 0.000 claims 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims 2
- 239000012044 organic layer Substances 0.000 claims 2
- 238000007911 parenteral administration Methods 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 238000001953 recrystallisation Methods 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- 230000028327 secretion Effects 0.000 claims 2
- 210000002966 serum Anatomy 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 claims 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 208000019395 Lactation disease Diseases 0.000 claims 1
- 229930195725 Mannitol Natural products 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
- 241001602876 Nata Species 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- 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 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 238000004378 air conditioning Methods 0.000 claims 1
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000002026 chloroform extract Substances 0.000 claims 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 235000013305 food Nutrition 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 238000007912 intraperitoneal administration Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000002075 main ingredient Substances 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- 229950002475 mesilate Drugs 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- 239000008267 milk Substances 0.000 claims 1
- 210000004080 milk Anatomy 0.000 claims 1
- 235000013336 milk Nutrition 0.000 claims 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims 1
- 210000001577 neostriatum Anatomy 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910003446 platinum oxide Inorganic materials 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 238000005303 weighing Methods 0.000 claims 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 208000024891 symptom Diseases 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- QNFGJGPPJHGEIA-UHFFFAOYSA-N acetyl acetate;n,n-diethylethanamine Chemical compound CCN(CC)CC.CC(=O)OC(C)=O QNFGJGPPJHGEIA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- ORIBUSCBDFDAIQ-HCGVIMEBSA-N methyl (6ar,10ar)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)C(=O)OC)C2)=C3C2=CNC3=C1 ORIBUSCBDFDAIQ-HCGVIMEBSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 in position 8
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/080,768 US4246265A (en) | 1979-10-01 | 1979-10-01 | 6-n-Propyl-8α-methoxymethyl or methylmercaptomethylergolines and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU976851A3 true SU976851A3 (ru) | 1982-11-23 |
Family
ID=22159504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802984351A SU976851A3 (ru) | 1979-10-01 | 1980-10-01 | Способ получени D-6- @ -пропил-8 L-метил /меркапто или оксо/ метилэрголина или его солей |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4246265A (enExample) |
| EP (1) | EP0026671B1 (enExample) |
| JP (1) | JPS5657787A (enExample) |
| KR (1) | KR830003478A (enExample) |
| AT (1) | AT373251B (enExample) |
| AU (1) | AU529508B2 (enExample) |
| BE (1) | BE885385A (enExample) |
| BG (1) | BG34908A3 (enExample) |
| CA (1) | CA1137079A (enExample) |
| CH (1) | CH645642A5 (enExample) |
| CS (1) | CS223834B2 (enExample) |
| DD (1) | DD153372A5 (enExample) |
| DE (1) | DE3069771D1 (enExample) |
| DK (1) | DK413780A (enExample) |
| EG (1) | EG14583A (enExample) |
| ES (1) | ES8200697A1 (enExample) |
| FI (1) | FI803025A7 (enExample) |
| FR (1) | FR2466465A1 (enExample) |
| GB (1) | GB2058790B (enExample) |
| GR (1) | GR70067B (enExample) |
| HU (1) | HU181766B (enExample) |
| IE (1) | IE50429B1 (enExample) |
| IL (1) | IL61143A0 (enExample) |
| IT (1) | IT1133631B (enExample) |
| NZ (1) | NZ195053A (enExample) |
| PH (1) | PH15021A (enExample) |
| PL (1) | PL226917A1 (enExample) |
| PT (1) | PT71840B (enExample) |
| RO (1) | RO81115B (enExample) |
| SU (1) | SU976851A3 (enExample) |
| YU (1) | YU247280A (enExample) |
| ZA (1) | ZA805959B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH644606A5 (de) * | 1980-09-23 | 1984-08-15 | Sandoz Ag | Verfahren zur isomerisierung von 9,10-dihydrolysergsaeurederivaten. |
| DE3216870A1 (de) * | 1982-05-03 | 1983-11-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Pharmazeutische zubereitungen mit zytostatischer wirkung |
| US4675322A (en) * | 1984-12-10 | 1987-06-23 | Eli Lilly And Company | 1-Substituted-6-n-propyl-8β-methylthio-methylergolines |
| US4683313A (en) * | 1985-06-24 | 1987-07-28 | Eli Lilly And Company | 2-alkyl(or phenyl)thio-6-N alkyl ergolines and 4-dialkylaminotetrahydrobenz[c,d]indoles |
| US4782152A (en) * | 1985-08-16 | 1988-11-01 | Eli Lilly And Company | Decyanation of pergolide intermediate |
| US4772709A (en) * | 1985-10-01 | 1988-09-20 | Eli Lilly And Company | Process of making ketoalkanol esters of dihydrolysergic acid |
| FR2589734B1 (fr) * | 1985-11-13 | 1988-09-02 | Roussel Uclaf | Utilisation de derives de l'ergoline a l'obtention d'un medicament a visee geriatrique |
| US5668155A (en) * | 1988-05-10 | 1997-09-16 | The General Hospital Corporation | Administration of pirenzepine, methyl scopolamine and other muscarinic receptor antagonists for treatment of lipid metabolism disorders |
| DE3913756A1 (de) * | 1989-04-21 | 1990-10-25 | Schering Ag | 8(beta)-substituierte ergoline, verfahren zu ihrer herstellung und ihre verwendung |
| IT1307934B1 (it) | 1999-01-27 | 2001-11-29 | Poli Ind Chimica Spa | Processo per la preparazione di derivati alchimercaptometilergolinici. |
| US6388079B1 (en) * | 2000-08-29 | 2002-05-14 | Scinopharm Singapore Pte Ltd. | Process for preparing pergolide |
| US7019140B2 (en) | 2002-03-15 | 2006-03-28 | Antibioticos S.P.A. | Process for the synthesis of pergolide |
| US8821915B2 (en) | 2002-08-09 | 2014-09-02 | Veroscience, Llc | Therapeutic process for the treatment of the metabolic syndrome and associated metabolic disorders |
| GB0409785D0 (en) * | 2004-04-30 | 2004-06-09 | Resolution Chemicals Ltd | Preparation of cabergoline |
| US7339060B2 (en) | 2005-03-23 | 2008-03-04 | Resolution Chemicals, Ltd. | Preparation of cabergoline |
| GB0505965D0 (en) * | 2005-03-23 | 2005-04-27 | Resolution Chemicals Ltd | Preparation of cabergoline |
| US20070197576A1 (en) * | 2006-02-08 | 2007-08-23 | Resolution Chemicals Limited | Production of Cabergoline and Novel Polymorphic Form Thereof |
| MX388192B (es) | 2014-09-25 | 2025-03-19 | Boehringer Ingelheim Vetmedica Gmbh | Tratamiento de combinación y/o prevención de trastornos metabólicos en animales equinos. |
| WO2019234069A1 (en) | 2018-06-08 | 2019-12-12 | Boehringer Ingelheim Vetmedica Gmbh | Liquid pharmaceutical compositions comprising pergolide |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3901894A (en) * | 1974-06-06 | 1975-08-26 | Lilly Co Eli | 8-thiomethylergolines |
| DE2657771A1 (de) * | 1976-01-02 | 1977-07-14 | Sandoz Ag | Neue organische verbindungen, ihre verwendung und herstellung |
| US4166182A (en) * | 1978-02-08 | 1979-08-28 | Eli Lilly And Company | 6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds |
| US4202979A (en) * | 1979-01-11 | 1980-05-13 | Eli Lilly And Company | 6-Ethyl(or allyl)-8-methoxymethyl or methylmercaptomethylergolines and related compounds |
-
1979
- 1979-10-01 US US06/080,768 patent/US4246265A/en not_active Expired - Lifetime
-
1980
- 1980-09-25 ZA ZA00805959A patent/ZA805959B/xx unknown
- 1980-09-25 BE BE1/9966A patent/BE885385A/fr not_active IP Right Cessation
- 1980-09-25 NZ NZ195053A patent/NZ195053A/xx unknown
- 1980-09-25 RO RO102217A patent/RO81115B/ro unknown
- 1980-09-25 FR FR8020639A patent/FR2466465A1/fr active Granted
- 1980-09-25 GR GR62959A patent/GR70067B/el unknown
- 1980-09-25 CA CA000361035A patent/CA1137079A/en not_active Expired
- 1980-09-25 FI FI803025A patent/FI803025A7/fi not_active Application Discontinuation
- 1980-09-25 PL PL22691780A patent/PL226917A1/xx unknown
- 1980-09-26 IL IL61143A patent/IL61143A0/xx unknown
- 1980-09-26 CS CS806515A patent/CS223834B2/cs unknown
- 1980-09-26 PT PT71840A patent/PT71840B/pt unknown
- 1980-09-27 EG EG80594A patent/EG14583A/xx active
- 1980-09-29 YU YU02472/80A patent/YU247280A/xx unknown
- 1980-09-29 BG BG049173A patent/BG34908A3/xx unknown
- 1980-09-29 IT IT25004/80A patent/IT1133631B/it active
- 1980-09-29 HU HU802373A patent/HU181766B/hu unknown
- 1980-09-29 JP JP13668780A patent/JPS5657787A/ja active Pending
- 1980-09-30 CH CH730780A patent/CH645642A5/fr not_active IP Right Cessation
- 1980-09-30 AU AU62807/80A patent/AU529508B2/en not_active Ceased
- 1980-09-30 GB GB8031440A patent/GB2058790B/en not_active Expired
- 1980-09-30 PH PH24648A patent/PH15021A/en unknown
- 1980-09-30 ES ES495520A patent/ES8200697A1/es not_active Expired
- 1980-09-30 IE IE2036/80A patent/IE50429B1/en unknown
- 1980-09-30 EP EP80303447A patent/EP0026671B1/en not_active Expired
- 1980-09-30 DE DE8080303447T patent/DE3069771D1/de not_active Expired
- 1980-09-30 KR KR1019800003793A patent/KR830003478A/ko not_active Ceased
- 1980-09-30 DK DK413780A patent/DK413780A/da not_active Application Discontinuation
- 1980-09-30 AT AT0487480A patent/AT373251B/de not_active IP Right Cessation
- 1980-09-30 DD DD80224224A patent/DD153372A5/de unknown
- 1980-10-01 SU SU802984351A patent/SU976851A3/ru active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU976851A3 (ru) | Способ получени D-6- @ -пропил-8 L-метил /меркапто или оксо/ метилэрголина или его солей | |
| SU912045A3 (ru) | Способ получени 6-замещенных 8-метоксиметил-или 8-метилмеркаптометилэрголинов или их солей | |
| US4514393A (en) | New derivatives of biliary acids, process for the production thereof and pharmaceutical compositions containing the same | |
| JPS582946B2 (ja) | ８− チオメチルエルゴリンルイノ セイホウ | |
| JPS63280092A (ja) | β―Ｄ―フェニルチオキシロシドを含むオシド誘導体 | |
| AU607100B2 (en) | New androstane 17-carboxylic acid ester, process for their preparation and drugs containing them | |
| SU1308196A3 (ru) | Способ получени 5,11-дигидро-11- @ (1-метил-4-пиперидинил)-амино @ -карбонил @ -6 @ -дибенз ( @ , @ )азепин-6-она или его солей | |
| US3881017A (en) | 9-Thiaprostaglandin compositions | |
| JPH069685A (ja) | １７位にメチレンラクトン基を含有する新規なステロイド、それらの製造法及び中間体、それらの薬剤としての使用並びにそれらを含有する製薬組成物 | |
| PL131618B1 (en) | Process for preparing novel inhibitors of dipeptase | |
| FR2542743A1 (fr) | Analogues de prostaglandines a substituant 7-oxabicycloheptane, a proprietes therapeutiques | |
| Schmidlin et al. | Approaches to the Synthesis of Cytochalasans. Part 3. Synthesis of a substituted tetrahydroisoindolinone moiety possessing the same relative configuration as proxiphomin | |
| WO1989003834A1 (fr) | Derives azacyclohexyliques substitues | |
| GB2124215A (en) | Eburnane-oxime derivatives | |
| FI70027C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 1819-dinorpregn-4-en-3,20-dioner | |
| McClelland et al. | Synthesis of aryl ortho esters from benzanilide acetals | |
| KR950008970B1 (ko) | t-부틸 에르골린 유도체의 제조방법 | |
| US4762944A (en) | Butenoic acid derivatives, pharmaceutical compositions containing them and process for preparing same | |
| KR830000654B1 (ko) | 테트라하이드로-2H-벤조[c]피롤의 제조방법 | |
| US4425358A (en) | 13-Thia-prostacycline derivatives | |
| MC514A1 (fr) | Nouveaux dérivés de l'urée et leur préparation | |
| WO1981003021A1 (en) | Bis-hydroxybenzyl derivatives,processes for their preparation and pharmaceutical composition containing same | |
| GB2123413A (en) | Eburnane-oxime ethers | |
| WO1983002775A1 (en) | Ergot alkaloids, manufacturing process thereof and pharmaceutical preparations containing them | |
| SU1189351A3 (ru) | Способ получени 5 @ -/2 @ -бутил/-пептидэрготалкалоида или его аддитивных солей с кислотами |