DE2700276A1 - Ergolin-derivate, verfahren zu ihrer herstellung und arzneimittel - Google Patents
Ergolin-derivate, verfahren zu ihrer herstellung und arzneimittelInfo
- Publication number
- DE2700276A1 DE2700276A1 DE19772700276 DE2700276A DE2700276A1 DE 2700276 A1 DE2700276 A1 DE 2700276A1 DE 19772700276 DE19772700276 DE 19772700276 DE 2700276 A DE2700276 A DE 2700276A DE 2700276 A1 DE2700276 A1 DE 2700276A1
- Authority
- DE
- Germany
- Prior art keywords
- pyridyl
- methoxy
- dimethylergoline
- methyl
- methanamine
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 210000001772 blood platelet Anatomy 0.000 description 5
- 210000004623 platelet-rich plasma Anatomy 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229960003642 nicergoline Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- AQHJXELXFBINLL-UHFFFAOYSA-N 1h-pyridine-2-thione;sodium Chemical compound [Na].SC1=CC=CC=N1 AQHJXELXFBINLL-UHFFFAOYSA-N 0.000 description 1
- 150000003930 2-aminopyridines Chemical class 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BPYHGTCRXDWOIQ-UHFFFAOYSA-N 3-nitropyridin-2-amine Chemical compound NC1=NC=CC=C1[N+]([O-])=O BPYHGTCRXDWOIQ-UHFFFAOYSA-N 0.000 description 1
- BRBUBVKGJRPRRD-UHFFFAOYSA-N 4,6-dimethylpyridin-2-amine Chemical compound CC1=CC(C)=NC(N)=C1 BRBUBVKGJRPRRD-UHFFFAOYSA-N 0.000 description 1
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 1
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
- BHQUBONFIYNJDA-UHFFFAOYSA-N 5-nitro-1h-pyridine-2-thione Chemical compound [O-][N+](=O)C1=CC=C(S)N=C1 BHQUBONFIYNJDA-UHFFFAOYSA-N 0.000 description 1
- UGSBCCAHDVCHGI-UHFFFAOYSA-N 5-nitropyridin-2-amine Chemical compound NC1=CC=C([N+]([O-])=O)C=N1 UGSBCCAHDVCHGI-UHFFFAOYSA-N 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- RRLHMJHRFMHVNM-BQVXCWBNSA-N [(2s,3r,6r)-6-[5-[5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxypentoxy]-2-methyl-3,6-dihydro-2h-pyran-3-yl] acetate Chemical compound C1=C[C@@H](OC(C)=O)[C@H](C)O[C@H]1OCCCCCOC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 RRLHMJHRFMHVNM-BQVXCWBNSA-N 0.000 description 1
- XMVAISYXWMEOTD-MQVPCNEGSA-N [(6ar,9r,10as)-10a-methoxy-4,7-dimethyl-6a,8,9,10-tetrahydro-6h-indolo[4,3-fg]quinoline-9-yl]methyl 4-methylbenzenesulfonate Chemical compound C([C@@H]1C[C@]2([C@H](N(C)C1)CC=1C3=C2C=CC=C3N(C)C=1)OC)OS(=O)(=O)C1=CC=C(C)C=C1 XMVAISYXWMEOTD-MQVPCNEGSA-N 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- RICLFGYGYQXUFH-UHFFFAOYSA-N buspirone hydrochloride Chemical compound [H+].[Cl-].C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 RICLFGYGYQXUFH-UHFFFAOYSA-N 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000001 effect on platelet aggregation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 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
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 238000005303 weighing Methods 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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 |
|---|---|---|---|
| GB738/76A GB1513322A (en) | 1976-01-09 | 1976-01-09 | Heterocyclic ergoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2700276A1 true DE2700276A1 (de) | 1977-08-18 |
Family
ID=9709660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772700276 Withdrawn DE2700276A1 (de) | 1976-01-09 | 1977-01-05 | Ergolin-derivate, verfahren zu ihrer herstellung und arzneimittel |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4089862A (enExample) |
| JP (1) | JPS5287199A (enExample) |
| CH (1) | CH627466A5 (enExample) |
| DE (1) | DE2700276A1 (enExample) |
| FR (1) | FR2337725A1 (enExample) |
| GB (1) | GB1513322A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4753949A (en) * | 1985-06-21 | 1988-06-28 | Richter Gedeon Vegyeszeti Gyar Rt. | 2-chloronicergoline having antihypoxic activity |
| US4980475A (en) * | 1984-03-27 | 1990-12-25 | I D B Holding S.P.A. | Process for the preparation of N-10 alpha-methoxyl-lumilysergol and esters, thereof, and intermediates for their preparation |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU526764B2 (en) * | 1978-09-08 | 1983-01-27 | Farmitalia Carlo Erba S.P.A. | Ergoline derivatives |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3014909A (en) * | 1961-12-26 | New basically substituted g-methyx- | ||
| NL278401A (enExample) * | 1961-05-29 | |||
| CH463524A (de) * | 1965-08-16 | 1968-10-15 | Sandoz Ag | Verfahren zur Herstellung von neuen Lysergsäurederivaten |
| NL7303428A (enExample) * | 1972-03-17 | 1973-09-19 | ||
| CA990287A (en) * | 1972-09-26 | 1976-06-01 | Sandoz Patents Limited | 13-bromo-lysergic acid compounds |
| US3996228A (en) * | 1973-12-21 | 1976-12-07 | Societa' Farmaceutici Italia S.P.A. | Pyrimidinoaminoethyl ergoline derivatives |
| US4004011A (en) * | 1974-04-16 | 1977-01-18 | Sandoz Ltd. | 3-Pyridylamine substituted ergolines |
-
1976
- 1976-01-09 GB GB738/76A patent/GB1513322A/en not_active Expired
-
1977
- 1977-01-04 US US05/756,725 patent/US4089862A/en not_active Expired - Lifetime
- 1977-01-05 DE DE19772700276 patent/DE2700276A1/de not_active Withdrawn
- 1977-01-07 FR FR7700336A patent/FR2337725A1/fr active Granted
- 1977-01-07 JP JP71077A patent/JPS5287199A/ja active Pending
- 1977-01-07 CH CH21177A patent/CH627466A5/de not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980475A (en) * | 1984-03-27 | 1990-12-25 | I D B Holding S.P.A. | Process for the preparation of N-10 alpha-methoxyl-lumilysergol and esters, thereof, and intermediates for their preparation |
| US4753949A (en) * | 1985-06-21 | 1988-06-28 | Richter Gedeon Vegyeszeti Gyar Rt. | 2-chloronicergoline having antihypoxic activity |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2337725A1 (fr) | 1977-08-05 |
| FR2337725B1 (enExample) | 1980-03-14 |
| GB1513322A (en) | 1978-06-07 |
| CH627466A5 (de) | 1982-01-15 |
| JPS5287199A (en) | 1977-07-20 |
| US4089862A (en) | 1978-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: FARMITALIA CARLO ERBA S.P.A., 20159 MILANO, IT |
|
| 8141 | Disposal/no request for examination |