SU724085A3 - Способ получени 6-метил-8нитрометилэрголина или его солей - Google Patents
Способ получени 6-метил-8нитрометилэрголина или его солей Download PDFInfo
- Publication number
- SU724085A3 SU724085A3 SU762379565A SU2379565A SU724085A3 SU 724085 A3 SU724085 A3 SU 724085A3 SU 762379565 A SU762379565 A SU 762379565A SU 2379565 A SU2379565 A SU 2379565A SU 724085 A3 SU724085 A3 SU 724085A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- compound
- reacting
- methyl
- soch
- salts
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 8
- ILTXSGSVTRVBSQ-SKNXHYNKSA-N (6ar,10ar)-7-methyl-9-(nitromethyl)-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2CC(C[N+]([O-])=O)CN([C@@H]2C2)C)=C3C2=CNC3=C1 ILTXSGSVTRVBSQ-SKNXHYNKSA-N 0.000 title 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 8
- 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 class 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 abstract description 4
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- DEHHSXGUVDBSAH-NMPNHXORSA-N [(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]methyl 4-methylbenzenesulfonate Chemical compound CN([C@H]1[C@@H](C=2C=CC=C3NC=C(C=23)C1)C1)CC1COS(=O)(=O)C1=CC=C(C)C=C1 DEHHSXGUVDBSAH-NMPNHXORSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 5
- -1 methanesulphonyloxy Chemical group 0.000 abstract description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 102000003946 Prolactin Human genes 0.000 abstract 1
- 108010057464 Prolactin Proteins 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229940097325 prolactin Drugs 0.000 abstract 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07D457/02—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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (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)
Description
снг«02
N-СНз
или его солей, заключающийс в том, что 6метил-8- (п-толуолсульфонилоксиметил) -эрголин подвергают взаимодействию с нитритом натри в органическом растворителе при температуре от 0°С до 100° С с последующим выделением целевого продукта в свободном виде или в виде соли.
В качестве растворител обычно используют диметилформамид или диметилсульфоксид.
В качестве кислот, используемых дл получени солей, могут быть использованы следующие: сол на , серна , фосфорна , бромйстбводородка , иодистоводородна , азотна , а также органические кислоты, такие как метансульфокислота , малонова , бензойна , малёинова и др.
Пример 1. Раствор, состо щий из 1,07 г D-6-метил-8-(п-толуолсульфонилоксиметил )-зрголина и 25 мл диметилсульфоксида, содержащий Г,5 нитрита натри , перемешивают в атмосфере азота при 25°С в течение 46 час. Реакци6н1 ю смесь наливают в 100 мл воды и Из нее зкстрагируют в этилацетат водонерастворимый продукт. Органические экстракты комб1шируют, промывают водным насыщенным раствором хлористого натри , высушивают и из них под пониженным давлением экстрагируют растворитель, благодар чему получают продукт в виде пены. Пену помещают на хроматографическую колонку, содержащую 50 г флоризила и элюируют хлороформом. Элюатные фракции
В которых с помощью тонкослойной хроматографии было установлено содержание требуемого продукта, комбинируют и из них под пониженным давлением удал ют растворитель, в результате получают 75 млг 0-6-метил-8-нитрометилэрголина . Т. пл. 263-265°С (разл). Найдено,%: С 67,09; Н 6,81; N 14,93,
C.sHjgNsOz
Вычислено,%: С 67,35; Н 6,71; N 14,73.
Пример 2. Раствор, 2 г 0-6-метил-8-нитрометилэрголина , полученного аналогично примеру 1, перемешивают в 50 мл простого диэтилового эфира при одновременном барботировании реакционной смеси избыточным количеством хлористого водорода. Реакционную смесь отфильтровывают, в результате чего получают 0-6-метил-8-нитрометш1эрголин в виде белого кристаллического твердого вещества.
Claims (1)
- Формула изобретениСпособ получени 6-метил-8-нитрометилэрголина формулы „снгыоN-CHjннили его солей, отличающийс тем, что 6-метил-8-(п-толуолсульфонилоксиметил )-эрголИн подвергают взаимодействию с нитритом натри в органическом растворителе при температуре от 0°С до 100° С с последующим вьщелением целевого продукта в свободном виде или в виде соли.Источники информации, прин тые во внимание при экспертизе 1. Патент США N 3324133, кл. 260-285.7, 1967..
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/530,318 US3985752A (en) | 1974-12-06 | 1974-12-06 | 6-Methyl-8-(substituted) methylergolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU724085A3 true SU724085A3 (ru) | 1980-03-25 |
Family
ID=24113213
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752194455A SU685155A3 (ru) | 1974-12-06 | 1975-12-04 | Способ получени 6-метил-8 (замещенных)-метилэрголинов или их солей |
| SU752194702A SU694075A3 (ru) | 1974-12-06 | 1975-12-04 | Способ получени 6-метил-8/замещенных/метилэрголинов или их солей |
| SU762379565A SU724085A3 (ru) | 1974-12-06 | 1976-07-12 | Способ получени 6-метил-8нитрометилэрголина или его солей |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752194455A SU685155A3 (ru) | 1974-12-06 | 1975-12-04 | Способ получени 6-метил-8 (замещенных)-метилэрголинов или их солей |
| SU752194702A SU694075A3 (ru) | 1974-12-06 | 1975-12-04 | Способ получени 6-метил-8/замещенных/метилэрголинов или их солей |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US3985752A (ru) |
| JP (2) | JPS5946235B2 (ru) |
| AR (2) | AR207664A1 (ru) |
| AT (2) | AT348141B (ru) |
| AU (1) | AU498226B2 (ru) |
| BE (1) | BE836308A (ru) |
| BG (3) | BG33435A3 (ru) |
| CA (2) | CA1062252A (ru) |
| CH (2) | CH617197A5 (ru) |
| CS (2) | CS200483B2 (ru) |
| DD (2) | DD123748A5 (ru) |
| DE (1) | DE2554000A1 (ru) |
| DK (2) | DK142321B (ru) |
| ES (3) | ES443276A1 (ru) |
| FR (1) | FR2293203A1 (ru) |
| GB (1) | GB1526835A (ru) |
| GR (2) | GR60026B (ru) |
| HU (3) | HU173847B (ru) |
| IE (1) | IE42372B1 (ru) |
| IL (1) | IL48573A (ru) |
| MX (1) | MX3113E (ru) |
| NL (1) | NL7514058A (ru) |
| PH (1) | PH12630A (ru) |
| PL (3) | PL102198B1 (ru) |
| RO (2) | RO65456A (ru) |
| SE (2) | SE421423B (ru) |
| SU (3) | SU685155A3 (ru) |
| YU (2) | YU304775A (ru) |
| ZA (1) | ZA757624B (ru) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| HU180467B (en) * | 1979-07-12 | 1983-03-28 | Gyogyszerkutato Intezet | Process for producing new ergol-8-ene- and ergoline-sceleted compounds |
| 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 |
| JPH02174820A (ja) * | 1988-12-27 | 1990-07-06 | Sekisui Chem Co Ltd | トイレット |
| AU2635599A (en) * | 1999-03-17 | 2000-10-04 | Eugen Eigenmann | Use of prolactin inhibitors for the treatment of fertility problems in animal species |
| DE10053397A1 (de) | 2000-10-20 | 2002-05-02 | Schering Ag | Verwendung eines dopaminergen Wirkstoffes zur Behandlung von dopaminerg behandelbaren Erkrankungen |
| US20070243240A9 (en) * | 2000-08-24 | 2007-10-18 | Fred Windt-Hanke | Transdermal therapeutic system |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695752C3 (de) * | 1966-07-29 | 1974-06-06 | Societa Farmaceutici Italia, Mailand (Italien) | 1 ,ö-Dimethyl-ebeta-N-carbobenzoxyaminomethyl-2,3-dihydro-1 Oalpha-ergolin und ein Verfahren zu seiner Herstellung |
| BE712054A (ru) * | 1967-03-16 | 1968-07-15 |
-
1974
- 1974-12-06 US US05/530,318 patent/US3985752A/en not_active Expired - Lifetime
-
1975
- 1975-01-01 AR AR261511A patent/AR207664A1/es active
- 1975-01-01 AR AR261512A patent/AR208104A1/es active
- 1975-11-20 CS CS757859A patent/CS200483B2/cs unknown
- 1975-11-20 CS CS757860A patent/CS199609B2/cs unknown
- 1975-11-27 GB GB48901/75A patent/GB1526835A/en not_active Expired
- 1975-11-28 PH PH17816A patent/PH12630A/en unknown
- 1975-11-28 GR GR49484A patent/GR60026B/el unknown
- 1975-11-28 MX MX004193U patent/MX3113E/es unknown
- 1975-11-28 GR GR49483A patent/GR60025B/el unknown
- 1975-11-30 IL IL48573A patent/IL48573A/xx unknown
- 1975-12-01 DE DE19752554000 patent/DE2554000A1/de not_active Withdrawn
- 1975-12-02 AU AU87182/75A patent/AU498226B2/en not_active Expired
- 1975-12-02 NL NL7514058A patent/NL7514058A/xx not_active Application Discontinuation
- 1975-12-02 CA CA240,915A patent/CA1062252A/en not_active Expired
- 1975-12-02 CA CA240,916A patent/CA1062253A/en not_active Expired
- 1975-12-03 JP JP50144581A patent/JPS5946235B2/ja not_active Expired
- 1975-12-03 SE SE7513641A patent/SE421423B/xx not_active IP Right Cessation
- 1975-12-03 YU YU03047/75A patent/YU304775A/xx unknown
- 1975-12-03 SE SE7513640A patent/SE421422B/xx not_active IP Right Cessation
- 1975-12-03 YU YU03048/75A patent/YU304875A/xx unknown
- 1975-12-04 CH CH1580275A patent/CH617197A5/de not_active IP Right Cessation
- 1975-12-04 ZA ZA757624A patent/ZA757624B/xx unknown
- 1975-12-04 SU SU752194455A patent/SU685155A3/ru active
- 1975-12-04 RO RO7584088A patent/RO65456A/ro unknown
- 1975-12-04 DK DK547575AA patent/DK142321B/da not_active IP Right Cessation
- 1975-12-04 PL PL1975185225A patent/PL102198B1/pl unknown
- 1975-12-04 HU HUEI000658 patent/HU173847B/hu unknown
- 1975-12-04 SU SU752194702A patent/SU694075A3/ru active
- 1975-12-04 PL PL1975208580A patent/PL106884B1/pl unknown
- 1975-12-04 RO RO7584087A patent/RO64281A/ro unknown
- 1975-12-04 HU HU75EI848A patent/HU175228B/hu unknown
- 1975-12-04 CH CH1580175A patent/CH619465A5/de not_active IP Right Cessation
- 1975-12-04 FR FR7537117A patent/FR2293203A1/fr active Granted
- 1975-12-04 PL PL1975185226A patent/PL102195B1/pl unknown
- 1975-12-04 DK DK547675A patent/DK547675A/da unknown
- 1975-12-04 HU HU75EI657A patent/HU173724B/hu unknown
- 1975-12-05 BG BG033760A patent/BG33435A3/xx unknown
- 1975-12-05 BG BG031706A patent/BG33288A3/xx unknown
- 1975-12-05 DD DD189914A patent/DD123748A5/xx unknown
- 1975-12-05 BG BG031705A patent/BG33287A3/xx unknown
- 1975-12-05 AT AT927875A patent/AT348141B/de not_active IP Right Cessation
- 1975-12-05 ES ES443276A patent/ES443276A1/es not_active Expired
- 1975-12-05 DD DD189913A patent/DD123749A5/xx unknown
- 1975-12-05 BE BE1007062A patent/BE836308A/xx not_active IP Right Cessation
- 1975-12-05 IE IE2657/75A patent/IE42372B1/en unknown
- 1975-12-05 ES ES443275A patent/ES443275A1/es not_active Expired
- 1975-12-05 AT AT927975A patent/AT347050B/de not_active IP Right Cessation
-
1976
- 1976-07-12 SU SU762379565A patent/SU724085A3/ru active
-
1977
- 1977-04-11 ES ES457709A patent/ES457709A1/es not_active Expired
-
1984
- 1984-04-24 JP JP59083605A patent/JPS6017795B2/ja not_active Expired
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