FR2460949A1 - Nouveaux derives de l'ergol-8-ene et de l'ergoline, procede de preparation de ces derives et medicaments les contenant - Google Patents
Nouveaux derives de l'ergol-8-ene et de l'ergoline, procede de preparation de ces derives et medicaments les contenant Download PDFInfo
- Publication number
- FR2460949A1 FR2460949A1 FR8015360A FR8015360A FR2460949A1 FR 2460949 A1 FR2460949 A1 FR 2460949A1 FR 8015360 A FR8015360 A FR 8015360A FR 8015360 A FR8015360 A FR 8015360A FR 2460949 A1 FR2460949 A1 FR 2460949A1
- Authority
- FR
- France
- Prior art keywords
- acid
- ergoline
- ene
- methyl
- general formula
- 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.)
- Granted
Links
- 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 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000003814 drug Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 39
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- 238000000034 method Methods 0.000 claims description 17
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- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
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- 241001331845 Equus asinus x caballus Species 0.000 claims description 2
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- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
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- 239000000047 product Substances 0.000 description 7
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 5
- 230000001430 anti-depressive effect Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 102000015554 Dopamine receptor Human genes 0.000 description 4
- 108050004812 Dopamine receptor Proteins 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
- 229940005513 antidepressants Drugs 0.000 description 4
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- KPJZHOPZRAFDTN-ZRGWGRIASA-N (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)CC)C2)=C3C2=CN(C)C3=C1 KPJZHOPZRAFDTN-ZRGWGRIASA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
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- 239000008346 aqueous phase Substances 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229960001186 methysergide Drugs 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000013558 reference substance Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- IUJDSEJGGMCXSG-UHFFFAOYSA-N Thiopental Chemical compound CCCC(C)C1(CC)C(=O)NC(=S)NC1=O IUJDSEJGGMCXSG-UHFFFAOYSA-N 0.000 description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 229960002802 bromocriptine Drugs 0.000 description 2
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 2
- 239000002036 chloroform fraction Substances 0.000 description 2
- 229960004704 dihydroergotamine Drugs 0.000 description 2
- HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine 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]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 description 2
- 239000012156 elution solvent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
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- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WGZBEDCLEXJQGW-IAQYHMDHSA-N (6ar,9r)-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CN(C)C3=C1 WGZBEDCLEXJQGW-IAQYHMDHSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
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- 241000699670 Mus sp. Species 0.000 description 1
- YSEXMKHXIOCEJA-FVFQAYNVSA-N Nicergoline Chemical compound C([C@@H]1C[C@]2([C@H](N(C)C1)CC=1C3=C2C=CC=C3N(C)C=1)OC)OC(=O)C1=CN=CC(Br)=C1 YSEXMKHXIOCEJA-FVFQAYNVSA-N 0.000 description 1
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- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229960004650 metergoline Drugs 0.000 description 1
- WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
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- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79GO1452A HU180467B (en) | 1979-07-12 | 1979-07-12 | Process for producing new ergol-8-ene- and ergoline-sceleted compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2460949A1 true FR2460949A1 (fr) | 1981-01-30 |
| FR2460949B1 FR2460949B1 (en, 2012) | 1983-01-21 |
Family
ID=10996898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8015360A Granted FR2460949A1 (fr) | 1979-07-12 | 1980-07-10 | Nouveaux derives de l'ergol-8-ene et de l'ergoline, procede de preparation de ces derives et medicaments les contenant |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4299836A (en, 2012) |
| JP (1) | JPS5653677A (en, 2012) |
| AU (1) | AU532293B2 (en, 2012) |
| BE (1) | BE884171A (en, 2012) |
| CA (1) | CA1149801A (en, 2012) |
| CH (1) | CH644120A5 (en, 2012) |
| DE (1) | DE3026271A1 (en, 2012) |
| DK (1) | DK160874C (en, 2012) |
| ES (1) | ES8106536A1 (en, 2012) |
| FR (1) | FR2460949A1 (en, 2012) |
| GB (1) | GB2055370B (en, 2012) |
| HU (1) | HU180467B (en, 2012) |
| IL (1) | IL60548A (en, 2012) |
| IT (1) | IT1149840B (en, 2012) |
| NL (1) | NL8004000A (en, 2012) |
| PH (1) | PH16358A (en, 2012) |
| SE (1) | SE436880B (en, 2012) |
| SU (2) | SU1053752A3 (en, 2012) |
| ZA (1) | ZA804198B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2173189B (en) * | 1985-02-21 | 1988-04-27 | Maruko Pharmaceutical Co | Ergoline derivatives and salts thereof and pharmaceutical compositions thereof |
| DE3623438C2 (de) * | 1986-07-10 | 1998-04-09 | Schering Ag | In 2-Stellung mit radioaktivem Iod markierte Ergolinylharnstoffderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Diagnostika |
| US5242678A (en) * | 1986-07-10 | 1993-09-07 | Schering Aktiengesellschaft | BR*-diagnostics for monoamine receptors |
| DE10066158B4 (de) * | 2000-08-24 | 2007-08-09 | Neurobiotec Gmbh | Verwendung eines transdermalen therapeutischen Systems zur Behandlung des Restless-Legs-Syndroms |
| 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 |
| US7398562B2 (en) | 2004-03-10 | 2008-07-15 | Easy Rhino Designs, Inc. | Article with 3-dimensional secondary element |
| RU2274640C1 (ru) * | 2004-09-15 | 2006-04-20 | Всероссийский научно-исследовательский институт лекарственных и ароматических растений ("ВИЛАР") | СПОСОБ БРОМИРОВАНИЯ α И β-ЭРГОКРИПТИНОВ |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2293203A1 (fr) * | 1974-12-06 | 1976-07-02 | Lilly Co Eli | 6-methyl-8-(methyl substitue) ergolines |
| DE2751071A1 (de) * | 1976-11-24 | 1978-06-01 | Simes | Sulfamoyl-derivate des 8-beta-aminomethylergolins |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL128196C (en, 2012) * | 1961-05-29 |
-
1979
- 1979-07-12 HU HU79GO1452A patent/HU180467B/hu not_active IP Right Cessation
-
1980
- 1980-07-04 BE BE1/9882A patent/BE884171A/fr not_active IP Right Cessation
- 1980-07-09 PH PH24263A patent/PH16358A/en unknown
- 1980-07-10 FR FR8015360A patent/FR2460949A1/fr active Granted
- 1980-07-10 US US06/167,341 patent/US4299836A/en not_active Expired - Lifetime
- 1980-07-11 DE DE19803026271 patent/DE3026271A1/de active Granted
- 1980-07-11 CA CA000355996A patent/CA1149801A/en not_active Expired
- 1980-07-11 ES ES493335A patent/ES8106536A1/es not_active Expired
- 1980-07-11 IT IT23387/80A patent/IT1149840B/it active
- 1980-07-11 JP JP9412380A patent/JPS5653677A/ja active Granted
- 1980-07-11 ZA ZA00804198A patent/ZA804198B/xx unknown
- 1980-07-11 NL NL8004000A patent/NL8004000A/nl not_active Application Discontinuation
- 1980-07-11 CH CH533980A patent/CH644120A5/de not_active IP Right Cessation
- 1980-07-11 SE SE8005126A patent/SE436880B/sv not_active IP Right Cessation
- 1980-07-11 IL IL60548A patent/IL60548A/xx unknown
- 1980-07-11 GB GB8022824A patent/GB2055370B/en not_active Expired
- 1980-07-11 DK DK300080A patent/DK160874C/da not_active IP Right Cessation
- 1980-07-11 SU SU802949069A patent/SU1053752A3/ru active
- 1980-07-11 AU AU60349/80A patent/AU532293B2/en not_active Ceased
-
1982
- 1982-02-23 SU SU823394304A patent/SU1072806A3/ru active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2293203A1 (fr) * | 1974-12-06 | 1976-07-02 | Lilly Co Eli | 6-methyl-8-(methyl substitue) ergolines |
| DE2751071A1 (de) * | 1976-11-24 | 1978-06-01 | Simes | Sulfamoyl-derivate des 8-beta-aminomethylergolins |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5653677A (en) | 1981-05-13 |
| IT1149840B (it) | 1986-12-10 |
| FR2460949B1 (en, 2012) | 1983-01-21 |
| IT8023387A0 (it) | 1980-07-11 |
| US4299836A (en) | 1981-11-10 |
| DE3026271A1 (de) | 1981-02-12 |
| ZA804198B (en) | 1981-07-29 |
| AU532293B2 (en) | 1983-09-22 |
| SU1053752A3 (ru) | 1983-11-07 |
| ES8106536A1 (es) | 1981-10-16 |
| HU180467B (en) | 1983-03-28 |
| DE3026271C2 (en, 2012) | 1991-07-25 |
| DK300080A (da) | 1981-01-13 |
| IL60548A (en) | 1983-07-31 |
| GB2055370A (en) | 1981-03-04 |
| DK160874B (da) | 1991-04-29 |
| AU6034980A (en) | 1981-01-15 |
| JPH0210834B2 (en, 2012) | 1990-03-09 |
| PH16358A (en) | 1983-09-08 |
| DK160874C (da) | 1992-02-24 |
| SE8005126L (sv) | 1981-01-13 |
| GB2055370B (en) | 1983-05-05 |
| SE436880B (sv) | 1985-01-28 |
| CA1149801A (en) | 1983-07-12 |
| IL60548A0 (en) | 1980-09-16 |
| CH644120A5 (de) | 1984-07-13 |
| NL8004000A (nl) | 1981-01-14 |
| BE884171A (fr) | 1981-01-05 |
| SU1072806A3 (ru) | 1984-02-07 |
| ES493335A0 (es) | 1981-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |