SU1272988A3 - Способ получени эрголинов или их физиологически приемлемых солей - Google Patents
Способ получени эрголинов или их физиологически приемлемых солей Download PDFInfo
- Publication number
- SU1272988A3 SU1272988A3 SU823470940A SU3470940A SU1272988A3 SU 1272988 A3 SU1272988 A3 SU 1272988A3 SU 823470940 A SU823470940 A SU 823470940A SU 3470940 A SU3470940 A SU 3470940A SU 1272988 A3 SU1272988 A3 SU 1272988A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- physiologically acceptable
- ergolinyl
- acid
- producing
- acceptable salts
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 5
- RHGUXDUPXYFCTE-ZWNOBZJWSA-N ergoline Chemical class C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=CNC3=C1 RHGUXDUPXYFCTE-ZWNOBZJWSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 6
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000012948 isocyanate Substances 0.000 claims abstract description 3
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- -1 alkaline earth metal carbonate Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 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 abstract description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- C07D457/06—Lysergic acid amides
-
- 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
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| DE3135305A DE3135305C2 (de) | 1981-09-03 | 1981-09-03 | Verfahren zur Herstellung von 8-Ergolinyl-harnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1272988A3 true SU1272988A3 (ru) | 1986-11-23 |
Family
ID=6141023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823470940A SU1272988A3 (ru) | 1981-09-03 | 1982-08-03 | Способ получени эрголинов или их физиологически приемлемых солей |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4748248A (enExample) |
| EP (1) | EP0074921B1 (enExample) |
| JP (1) | JPS5855483A (enExample) |
| AT (1) | ATE11289T1 (enExample) |
| AU (1) | AU555576B2 (enExample) |
| CA (1) | CA1175813A (enExample) |
| CS (1) | CS241122B2 (enExample) |
| DD (1) | DD203544A5 (enExample) |
| DE (2) | DE3135305C2 (enExample) |
| DK (1) | DK161646C (enExample) |
| ES (1) | ES515428A0 (enExample) |
| GR (1) | GR76897B (enExample) |
| HU (1) | HU186969B (enExample) |
| IE (1) | IE53437B1 (enExample) |
| IL (1) | IL66679A (enExample) |
| SU (1) | SU1272988A3 (enExample) |
| YU (1) | YU199282A (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3151912A1 (de) * | 1981-12-23 | 1983-06-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue ergolin-aminoderivate, verfahren zu ihrer herstellung und deren verwendung als arzneimittel |
| DE3309493A1 (de) * | 1983-03-14 | 1984-09-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Neue ergolin-derivate, verfahren zu ihrer herstellung sowie verwendung als arzneimittel |
| NL8503426A (nl) * | 1984-12-24 | 1986-07-16 | Sandoz Ag | 8alfa-acylamino-ergolinen, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten. |
| DE3915950A1 (de) * | 1989-05-12 | 1990-11-15 | Schering Ag | 8(alpha)-acylamino-ergoline, ihre herstellung und verwendung als arzneimittel |
| US20060171795A1 (en) * | 2005-01-28 | 2006-08-03 | Cromwell Stephen D | Substantial embedment of metallic debris |
| JP2010119349A (ja) * | 2008-11-20 | 2010-06-03 | Shinichi Okamoto | 即席のパンなどの穀物粉加工食品の製造方法 |
| BR112017015487A2 (pt) | 2015-01-20 | 2018-01-30 | Xoc Pharmaceuticals Inc | Composto; composição; método de tratamento e/ou prevenção de enxaqueca, als, doença de alzheimer, doença de parkinson, distúrbios extrapirimidais, depressão, náusea, êmese, síndrome das pernas inquietas, insônia, agressão, doença de huntington, doença cardiopulmonar, fibrogênese, hipertensão arterial pulmonar, ansiedade, dependências a drogas, distonia, parassonia ou hiperlactinemia em um indivíduo; métodos de agonização dos receptores d2, 5-ht1d, 5-ht1a e 5-ht2c, em um indivíduo; método de antagonização do receptor d3 em um indivíduo; métodos de agonização seletiva dos receptores 5 -ht1d, e 5-ht2c, método de fornecimento de atividade de antagonista funcional no receptor 5 -ht2b ou no receptor 5-ht7, ou em ambos, em um indivíduo; método de fornecimento de atividade de antagonista funcional nos receptores adrenérgicos em um indivíduo |
| CN107405346A (zh) * | 2015-01-20 | 2017-11-28 | Xoc制药股份有限公司 | 异麦角灵化合物及其用途 |
| CA3064274A1 (en) | 2017-06-01 | 2018-12-06 | Xoc Pharmaceuticals, Inc. | Ergoline derivatives for use in medicine |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3063869D1 (en) * | 1979-06-13 | 1983-07-28 | Schering Ag | (ergolin-yl)-n', n'-diethyl urea derivatives, their preparation and pharmaceutical compositions containing them |
-
1981
- 1981-09-03 DE DE3135305A patent/DE3135305C2/de not_active Expired
-
1982
- 1982-08-03 SU SU823470940A patent/SU1272988A3/ru active
- 1982-08-17 DK DK368382A patent/DK161646C/da not_active IP Right Cessation
- 1982-08-23 AT AT82730112T patent/ATE11289T1/de not_active IP Right Cessation
- 1982-08-23 EP EP82730112A patent/EP0074921B1/en not_active Expired
- 1982-08-23 DE DE8282730112T patent/DE3261963D1/de not_active Expired
- 1982-08-30 IL IL66679A patent/IL66679A/xx unknown
- 1982-08-31 DD DD82242909A patent/DD203544A5/de unknown
- 1982-08-31 AU AU87863/82A patent/AU555576B2/en not_active Ceased
- 1982-09-01 ES ES515428A patent/ES515428A0/es active Granted
- 1982-09-01 GR GR69181A patent/GR76897B/el unknown
- 1982-09-02 HU HU822824A patent/HU186969B/hu not_active IP Right Cessation
- 1982-09-02 CA CA000410636A patent/CA1175813A/en not_active Expired
- 1982-09-03 IE IE2156/82A patent/IE53437B1/en not_active IP Right Cessation
- 1982-09-03 YU YU01992/82A patent/YU199282A/xx unknown
- 1982-09-03 JP JP57152871A patent/JPS5855483A/ja active Granted
- 1982-09-03 CS CS826422A patent/CS241122B2/cs unknown
-
1985
- 1985-12-13 US US06/808,804 patent/US4748248A/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Каррер П..Курс органической химии. М.: Госхимиздат, 1960, с.163. Патент DE № 2924102, кл.с 07 D 457/12, опублик. 1980. * |
Also Published As
| Publication number | Publication date |
|---|---|
| DD203544A5 (de) | 1983-10-26 |
| DE3135305A1 (de) | 1983-03-10 |
| CS241122B2 (en) | 1986-03-13 |
| AU8786382A (en) | 1983-03-10 |
| GR76897B (enExample) | 1984-09-04 |
| US4748248A (en) | 1988-05-31 |
| DK161646C (da) | 1992-01-06 |
| JPS5855483A (ja) | 1983-04-01 |
| HU186969B (en) | 1985-10-28 |
| EP0074921B1 (en) | 1985-01-16 |
| YU199282A (en) | 1985-03-20 |
| IE822156L (en) | 1983-03-03 |
| DE3135305C2 (de) | 1983-07-21 |
| CS642282A2 (en) | 1985-07-16 |
| ES8305361A1 (es) | 1983-05-01 |
| ATE11289T1 (de) | 1985-02-15 |
| DK368382A (da) | 1983-03-04 |
| IL66679A0 (en) | 1982-12-31 |
| IE53437B1 (en) | 1988-11-09 |
| CA1175813A (en) | 1984-10-09 |
| EP0074921A1 (en) | 1983-03-23 |
| ES515428A0 (es) | 1983-05-01 |
| IL66679A (en) | 1986-04-29 |
| JPH0239511B2 (enExample) | 1990-09-05 |
| DE3261963D1 (en) | 1985-02-28 |
| DK161646B (da) | 1991-07-29 |
| AU555576B2 (en) | 1986-10-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2191647C (en) | Process improvement in the synthesis of n-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-ethylacetamide | |
| SU691089A3 (ru) | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов | |
| JPH0533711B2 (enExample) | ||
| SU1272988A3 (ru) | Способ получени эрголинов или их физиологически приемлемых солей | |
| SU1055333A3 (ru) | Способ получени алкалоидов типа лейрозина или их кислых аддитивных солей | |
| US3420844A (en) | Pyrrole-2-carboxamido-propionamidines | |
| SU516355A3 (ru) | Способ получени производных 9,10-дигидро-лизергиновой кислоты | |
| Tamura et al. | Novel syntheses of thiazolo [3, 2‐b]‐s‐triazoles | |
| GB2036744A (en) | Eburnane derivatives | |
| US3758546A (en) | Methoxy amine derivatives and process for preparing them | |
| SU532340A3 (ru) | Способ получени 3-(5нитро-1-метил2-имидазолил)- -триазоло(4,3-в) пиридазинов или их солей | |
| FI88292B (fi) | Foerfarande foer framstaellning av n-(sulfonylmetyl)formamider | |
| JPS6148839B2 (enExample) | ||
| SU922108A1 (ru) | Способ получени производных 6-метил-8 @ -гидразинометилэрголина или их солей | |
| US4062891A (en) | N-formyl-2,3,5,6-dibenzobicyclo[5.1.0]octan-4-methylamine | |
| JP2771257B2 (ja) | イミダゾール誘導体の製法 | |
| US5643438A (en) | Process for the preparation of substituted diamino-dicarboxylic acid derivatives | |
| US4189444A (en) | Process for the preparation of N,N'-disubstituted 2-naphthaleneethanimidamide and intermediates used therein | |
| US3842086A (en) | Process for the preparation of substituted or unsubstituted pyridines | |
| HU195485B (en) | Process for producing aromatic carboxylic acid derivatives and -carboxamide derivatives | |
| SU1189351A3 (ru) | Способ получени 5 @ -/2 @ -бутил/-пептидэрготалкалоида или его аддитивных солей с кислотами | |
| NO863769L (no) | Fremgangsmaate for fremstilling av 4-hydroksy-2-oksopyrrolin-1-yl-acetamid. | |
| KR840002045B1 (ko) | 세파피린 에스테르의 제조방법 | |
| US3751462A (en) | Process for preparation of substituted fluoromethanesulfonanilides | |
| SU372813A1 (ru) | Способ получения алкалоидов |