CH641803A5 - 2-azaergolines et 2-aza-8(ou 9)ergolenes, et composition pharmaceutique les contenant. - Google Patents
2-azaergolines et 2-aza-8(ou 9)ergolenes, et composition pharmaceutique les contenant. Download PDFInfo
- Publication number
- CH641803A5 CH641803A5 CH605979A CH605979A CH641803A5 CH 641803 A5 CH641803 A5 CH 641803A5 CH 605979 A CH605979 A CH 605979A CH 605979 A CH605979 A CH 605979A CH 641803 A5 CH641803 A5 CH 641803A5
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- CH
- Switzerland
- Prior art keywords
- methyl
- alkyl
- acid
- formula
- group
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- ZFOZPCILROUMEK-LDYMZIIASA-N (2R,7R)-6,10,11-triazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),9(16),11,13-tetraene Chemical class C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=NNC3=C1 ZFOZPCILROUMEK-LDYMZIIASA-N 0.000 claims description 7
- 239000012954 diazonium Substances 0.000 claims description 7
- DAVNRFCJMIONPO-UHFFFAOYSA-N elymoclavine Natural products C1=CC(C2C=C(CO)CN(C2C2)C)=C3C2=CNC3=C1 DAVNRFCJMIONPO-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 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 group 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 description 6
- 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 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 4
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- 229940079593 drug Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- RHGUXDUPXYFCTE-ZWNOBZJWSA-N ergoline Chemical class C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=CNC3=C1 RHGUXDUPXYFCTE-ZWNOBZJWSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 2
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- 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 claims 2
- 229930013930 alkaloid Natural products 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 230000002196 ecbolic effect Effects 0.000 claims 2
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- 239000002863 oxytocic agent Substances 0.000 claims 2
- VUEGRGTYEAPQFU-CYBMUJFWSA-N (6ar)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline Chemical class C1=CC(C2=CCCN[C@@H]2C2)=C3C2=CNC3=C1 VUEGRGTYEAPQFU-CYBMUJFWSA-N 0.000 claims 1
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- NESVMZOPWPCFAU-UHFFFAOYSA-N Ergoclavinine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)CC(C)C)C)C2)=C3C2=CNC3=C1 NESVMZOPWPCFAU-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
- 241000628997 Flos Species 0.000 claims 1
- 241000605411 Lloydia Species 0.000 claims 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 claims 1
- NOFOWWRHEPHDCY-DAUURJMHSA-N Methylergonovine Maleate Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)CC)C2)=C3C2=CNC3=C1 NOFOWWRHEPHDCY-DAUURJMHSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 102000003946 Prolactin Human genes 0.000 claims 1
- 108010057464 Prolactin Proteins 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- YDOTUXAWKBPQJW-NSLWYYNWSA-N alpha-ergocryptine 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=CNC3=C1 YDOTUXAWKBPQJW-NSLWYYNWSA-N 0.000 claims 1
- 229950001817 alpha-ergocryptine Drugs 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- IAOSEBXZNXDPEE-UKRRQHHQSA-N elymoclavine Chemical compound C1=CC=C2[C@H]3C=C(CO)CN(C)[C@@H]3CC3=CN=C1[C]32 IAOSEBXZNXDPEE-UKRRQHHQSA-N 0.000 claims 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 claims 1
- OWEUDBYTKOYTAD-MKTPKCENSA-N ergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@@H]1C=C2C3=CC=CC4=NC=C([C]34)C[C@H]2N(C)C1)C(C)C)C1=CC=CC=C1 OWEUDBYTKOYTAD-MKTPKCENSA-N 0.000 claims 1
- HEFIYUQVAZFDEE-UHFFFAOYSA-N ergocristinine Natural products N12C(=O)C(C(C)C)(NC(=O)C3C=C4C=5C=CC=C6NC=C(C=56)CC4N(C)C3)OC2(O)C2CCCN2C(=O)C1CC1=CC=CC=C1 HEFIYUQVAZFDEE-UHFFFAOYSA-N 0.000 claims 1
- 229960001405 ergometrine Drugs 0.000 claims 1
- NESVMZOPWPCFAU-ZPRCMDFASA-N ergosine 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)C2)=C3C2=CNC3=C1 NESVMZOPWPCFAU-ZPRCMDFASA-N 0.000 claims 1
- 229960003133 ergot alkaloid Drugs 0.000 claims 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 claims 1
- 229960004943 ergotamine Drugs 0.000 claims 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
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)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Psychology (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 |
|---|---|---|---|
| US06/021,055 US4201862A (en) | 1979-03-16 | 1979-03-16 | 2-Azaergolines and 2-aza-8(or 9)-ergolenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH641803A5 true CH641803A5 (fr) | 1984-03-15 |
Family
ID=21802089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH605979A CH641803A5 (fr) | 1979-03-16 | 1979-06-28 | 2-azaergolines et 2-aza-8(ou 9)ergolenes, et composition pharmaceutique les contenant. |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4201862A (en, 2012) |
| EP (1) | EP0016274B1 (en, 2012) |
| JP (1) | JPS55124782A (en, 2012) |
| AR (1) | AR222178A1 (en, 2012) |
| AT (1) | AT371465B (en, 2012) |
| AU (1) | AU528075B2 (en, 2012) |
| BE (1) | BE877263A (en, 2012) |
| CA (2) | CA1107275A (en, 2012) |
| CH (1) | CH641803A5 (en, 2012) |
| CS (1) | CS213380B2 (en, 2012) |
| DD (1) | DD144671A5 (en, 2012) |
| DE (1) | DE2964803D1 (en, 2012) |
| DK (1) | DK268379A (en, 2012) |
| EG (1) | EG14250A (en, 2012) |
| ES (1) | ES8202341A1 (en, 2012) |
| FI (1) | FI66381C (en, 2012) |
| FR (1) | FR2451375A1 (en, 2012) |
| GB (1) | GB2044247B (en, 2012) |
| GR (1) | GR72397B (en, 2012) |
| HU (1) | HU181678B (en, 2012) |
| IE (1) | IE48360B1 (en, 2012) |
| IL (1) | IL57667A (en, 2012) |
| LU (1) | LU81437A1 (en, 2012) |
| NZ (1) | NZ190832A (en, 2012) |
| PH (1) | PH15302A (en, 2012) |
| PL (1) | PL128622B1 (en, 2012) |
| PT (1) | PT69832A (en, 2012) |
| RO (1) | RO76166A (en, 2012) |
| SU (1) | SU1005662A3 (en, 2012) |
| YU (1) | YU154679A (en, 2012) |
| ZA (1) | ZA793246B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL65269A0 (en) * | 1981-03-24 | 1982-05-31 | Lilly Co Eli | 6-substituted hexahydroindazolo or hexahydroisoindolo isoquinolines |
| GB2112382B (en) * | 1981-11-06 | 1985-03-06 | Erba Farmitalia | Ergoline derivatives |
| GB8419278D0 (en) * | 1984-07-27 | 1984-08-30 | Lilly Industries Ltd | Pharmaceutical compounds |
| US4798834A (en) * | 1987-08-31 | 1989-01-17 | Eli Lilly And Company | Optionally substituted (3β-9,10-didehydro-2,3-dihydro ergoline as serotonergic function enhancement |
| JPH02111285U (en, 2012) * | 1989-02-27 | 1990-09-05 | ||
| JPH0625197U (ja) * | 1992-01-14 | 1994-04-05 | 森下株式会社 | 網製輸送袋 |
| WO2023182288A1 (ja) | 2022-03-22 | 2023-09-28 | 国立大学法人京都大学 | シャルコー・マリー・ツース病の治療または予防薬 |
-
1979
- 1979-03-16 US US06/021,055 patent/US4201862A/en not_active Expired - Lifetime
- 1979-06-26 AU AU48413/79A patent/AU528075B2/en not_active Ceased
- 1979-06-26 NZ NZ190832A patent/NZ190832A/xx unknown
- 1979-06-26 BE BE1/9434A patent/BE877263A/xx not_active IP Right Cessation
- 1979-06-26 FR FR7916420A patent/FR2451375A1/fr active Granted
- 1979-06-26 IL IL57667A patent/IL57667A/xx unknown
- 1979-06-26 HU HU79EI861A patent/HU181678B/hu unknown
- 1979-06-26 DK DK268379A patent/DK268379A/da not_active Application Discontinuation
- 1979-06-27 RO RO7997971A patent/RO76166A/ro unknown
- 1979-06-27 CA CA330,695A patent/CA1107275A/en not_active Expired
- 1979-06-27 LU LU81437A patent/LU81437A1/xx unknown
- 1979-06-27 PT PT69832A patent/PT69832A/pt unknown
- 1979-06-27 PH PH22703A patent/PH15302A/en unknown
- 1979-06-28 EP EP79301249A patent/EP0016274B1/en not_active Expired
- 1979-06-28 JP JP8340879A patent/JPS55124782A/ja active Granted
- 1979-06-28 YU YU01546/79A patent/YU154679A/xx unknown
- 1979-06-28 SU SU792786204A patent/SU1005662A3/ru active
- 1979-06-28 CS CS794481A patent/CS213380B2/cs unknown
- 1979-06-28 GR GR59462A patent/GR72397B/el unknown
- 1979-06-28 FI FI792044A patent/FI66381C/fi not_active IP Right Cessation
- 1979-06-28 CH CH605979A patent/CH641803A5/fr not_active IP Right Cessation
- 1979-06-28 DE DE7979301249T patent/DE2964803D1/de not_active Expired
- 1979-06-28 GB GB7922529A patent/GB2044247B/en not_active Expired
- 1979-06-28 AT AT0452379A patent/AT371465B/de not_active IP Right Cessation
- 1979-06-29 DD DD79213991A patent/DD144671A5/de unknown
- 1979-06-29 ZA ZA793246A patent/ZA793246B/xx unknown
- 1979-06-29 PL PL1979216720A patent/PL128622B1/pl unknown
- 1979-06-29 AR AR277116A patent/AR222178A1/es active
- 1979-06-29 ES ES482092A patent/ES8202341A1/es not_active Expired
- 1979-08-08 IE IE1212/79A patent/IE48360B1/en unknown
-
1980
- 1980-02-13 EG EG84/80A patent/EG14250A/xx active
-
1982
- 1982-08-18 CA CA000409720A patent/CA1142176B/en not_active Expired
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |