SU645581A3 - Способ получени -2-галоид-6- метил-8-цианометил или -2-галоид6-метил-8-карбоксамидометилэрголинов - Google Patents
Способ получени -2-галоид-6- метил-8-цианометил или -2-галоид6-метил-8-карбоксамидометилэрголиновInfo
- Publication number
- SU645581A3 SU645581A3 SU731948966A SU1948966A SU645581A3 SU 645581 A3 SU645581 A3 SU 645581A3 SU 731948966 A SU731948966 A SU 731948966A SU 1948966 A SU1948966 A SU 1948966A SU 645581 A3 SU645581 A3 SU 645581A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- cyanomethyl
- halogen
- ergoline
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 238000005658 halogenation reaction Methods 0.000 claims description 3
- 229960002317 succinimide Drugs 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- 229960001413 acetanilide Drugs 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 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 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-Chlorosuccinimide Substances ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- -1 ergocryptin Chemical compound 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229940104869 fluorosilicate Drugs 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229950002454 lysergide Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- INOGLHRUEYDAHX-UHFFFAOYSA-N 1-chlorobenzotriazole Chemical compound C1=CC=C2N(Cl)N=NC2=C1 INOGLHRUEYDAHX-UHFFFAOYSA-N 0.000 description 1
- FOKBLPSREGFPGY-UHFFFAOYSA-N 2,4,5,6,7-pentachloroisoindole-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(=O)N(Cl)C2=O FOKBLPSREGFPGY-UHFFFAOYSA-N 0.000 description 1
- UJYGDMFEEDNVBF-UHFFFAOYSA-N Ergocorninine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)C(C)C)C(C)C)C2)=C3C2=CNC3=C1 UJYGDMFEEDNVBF-UHFFFAOYSA-N 0.000 description 1
- WVVSZNPYNCNODU-CJBNDPTMSA-N Ergometrine Natural products C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-CJBNDPTMSA-N 0.000 description 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 description 1
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
- WVVSZNPYNCNODU-XTQGRXLLSA-N Lysergic acid propanolamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-XTQGRXLLSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- WGXZDYPGLJYBJW-UHFFFAOYSA-N chloroform;propan-2-ol Chemical compound CC(C)O.ClC(Cl)Cl WGXZDYPGLJYBJW-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- XQUUDUKVJKNJNP-OGGGUQDZSA-N ergocornine Chemical compound C([C@H]1N(C)C2)C([C]34)=CN=C4C=CC=C3C1=C[C@H]2C(=O)N[C@@]1(C(C)C)C(=O)N2[C@@H](C(C)C)C(=O)N3CCC[C@H]3[C@]2(O)O1 XQUUDUKVJKNJNP-OGGGUQDZSA-N 0.000 description 1
- RHGUXDUPXYFCTE-ZWNOBZJWSA-N ergoline Chemical class C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=CNC3=C1 RHGUXDUPXYFCTE-ZWNOBZJWSA-N 0.000 description 1
- 229960001405 ergometrine Drugs 0.000 description 1
- OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 description 1
- 229960004943 ergotamine Drugs 0.000 description 1
- XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000380 hallucinogen Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 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 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| US27390272A | 1972-07-21 | 1972-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU645581A3 true SU645581A3 (ru) | 1979-01-30 |
Family
ID=23045910
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU731948966A SU645581A3 (ru) | 1972-07-21 | 1973-07-20 | Способ получени -2-галоид-6- метил-8-цианометил или -2-галоид6-метил-8-карбоксамидометилэрголинов |
| SU7402080295A SU584780A3 (ru) | 1972-07-21 | 1974-12-04 | Способ получени д-2-замещенных-6-метил-8-цианометил8-цианометилэрголинов или их солей |
| SU7502098198A SU575029A3 (ru) | 1972-07-21 | 1975-01-14 | Способ получени д -2,6-диметил-8цианметилэрголина или его солей |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402080295A SU584780A3 (ru) | 1972-07-21 | 1974-12-04 | Способ получени д-2-замещенных-6-метил-8-цианометил8-цианометилэрголинов или их солей |
| SU7502098198A SU575029A3 (ru) | 1972-07-21 | 1975-01-14 | Способ получени д -2,6-диметил-8цианметилэрголина или его солей |
Country Status (24)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1517971A (en) * | 1974-07-19 | 1978-07-19 | Sandoz Ltd | 8alpha-substituted ergoline i derivatives |
| US3968111A (en) * | 1974-12-06 | 1976-07-06 | Eli Lilly And Company | 8,8-Disubstituted-6-methylergolines and related compounds |
| US4166182A (en) * | 1978-02-08 | 1979-08-28 | Eli Lilly And Company | 6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds |
| AU526764B2 (en) * | 1978-09-08 | 1983-01-27 | Farmitalia Carlo Erba S.P.A. | Ergoline derivatives |
| ATE107647T1 (de) * | 1984-04-09 | 1994-07-15 | Schering Ag | 2-substituierte ergolin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel. |
| HU196598B (en) * | 1986-04-25 | 1988-12-28 | Richter Gedeon Vegyeszet | Process for producing 1- and/or 8-substituted 2-halogenated ergoline derivatives and pharmaceutics comprising such compounds |
| DE3620293A1 (de) * | 1986-06-16 | 1987-12-17 | Schering Ag | 1-und/oder 2-substituierte ergolinderivate |
| JPH0596382U (ja) * | 1992-05-28 | 1993-12-27 | イビデン株式会社 | ドアユニット |
-
1973
- 1973-01-01 AR AR249167A patent/AR206772A1/es active
- 1973-07-10 ZA ZA734627A patent/ZA734627B/xx unknown
- 1973-07-10 GB GB3289073A patent/GB1423065A/en not_active Expired
- 1973-07-12 IL IL42730A patent/IL42730A/en unknown
- 1973-07-12 IL IL48288A patent/IL48288A/en unknown
- 1973-07-12 SE SE7309781A patent/SE393111B/xx unknown
- 1973-07-13 DE DE2365974A patent/DE2365974A1/de not_active Withdrawn
- 1973-07-13 DE DE2335750A patent/DE2335750C3/de not_active Expired
- 1973-07-17 NL NL7309969A patent/NL7309969A/xx not_active Application Discontinuation
- 1973-07-17 YU YU1945/73A patent/YU36953B/xx unknown
- 1973-07-18 PH PH14835A patent/PH11229A/en unknown
- 1973-07-19 DK DK399873AA patent/DK140986B/da unknown
- 1973-07-19 BE BE1005246A patent/BE802531A/xx not_active IP Right Cessation
- 1973-07-19 HU HUEI485A patent/HU167274B/hu unknown
- 1973-07-20 BG BG26855A patent/BG21411A3/xx unknown
- 1973-07-20 CS CS735239A patent/CS208164B2/cs unknown
- 1973-07-20 RO RO7300083213A patent/RO63792A/ro unknown
- 1973-07-20 CH CH391076A patent/CH580625A5/xx not_active IP Right Cessation
- 1973-07-20 AT AT643473A patent/AT331425B/de not_active IP Right Cessation
- 1973-07-20 CA CA177,021A patent/CA1006159A/en not_active Expired
- 1973-07-20 BG BG024148A patent/BG21410A3/xx unknown
- 1973-07-20 IE IE1238/73A patent/IE37936B1/xx unknown
- 1973-07-20 FR FR7326708A patent/FR2193606B1/fr not_active Expired
- 1973-07-20 ES ES417078A patent/ES417078A1/es not_active Expired
- 1973-07-20 CH CH391276A patent/CH580626A5/xx not_active IP Right Cessation
- 1973-07-20 SU SU731948966A patent/SU645581A3/ru active
- 1973-07-20 CH CH391176A patent/CH578563A5/xx not_active IP Right Cessation
- 1973-07-20 RO RO7375548A patent/RO71305A/ro unknown
- 1973-07-20 CH CH1067873A patent/CH581135A5/xx not_active IP Right Cessation
- 1973-07-20 DD DD172402A patent/DD107690A5/xx unknown
- 1973-07-20 CH CH391376A patent/CH578564A5/xx not_active IP Right Cessation
- 1973-07-20 BG BG028443A patent/BG22400A3/xx unknown
- 1973-07-20 JP JP8074973A patent/JPS576431B2/ja not_active Expired
-
1974
- 1974-01-01 AR AR252738A patent/AR206887A1/es active
- 1974-12-04 SU SU7402080295A patent/SU584780A3/ru active
-
1975
- 1975-01-14 SU SU7502098198A patent/SU575029A3/ru active
- 1975-01-30 AR AR257473A patent/AR210072A1/es active
- 1975-10-13 IL IL48288A patent/IL48288A0/xx unknown
- 1975-11-21 ES ES442887A patent/ES442887A1/es not_active Expired
- 1975-11-21 ES ES442886A patent/ES442886A1/es not_active Expired
- 1975-11-21 ES ES442885A patent/ES442885A1/es not_active Expired
-
1976
- 1976-04-07 ES ES446789A patent/ES446789A1/es not_active Expired
- 1976-10-15 SE SE7611466A patent/SE410459B/xx unknown
- 1976-10-15 SE SE7611467A patent/SE410603B/xx unknown
-
1981
- 1981-08-07 JP JP56123937A patent/JPS5813541B2/ja not_active Expired
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