GB1423065A - D-6-methyl-2,8-disubstituted ergolines - Google Patents
D-6-methyl-2,8-disubstituted ergolinesInfo
- Publication number
- GB1423065A GB1423065A GB3289073A GB3289073A GB1423065A GB 1423065 A GB1423065 A GB 1423065A GB 3289073 A GB3289073 A GB 3289073A GB 3289073 A GB3289073 A GB 3289073A GB 1423065 A GB1423065 A GB 1423065A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- ergoline
- formula
- reacting
- compounds
- 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.)
- Expired
Links
- 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
- 150000001875 compounds Chemical class 0.000 abstract 5
- 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 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 102000003946 Prolactin Human genes 0.000 abstract 1
- 108010057464 Prolactin Proteins 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 230000028327 secretion Effects 0.000 abstract 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
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27390272A | 1972-07-21 | 1972-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1423065A true GB1423065A (en) | 1976-01-28 |
Family
ID=23045910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3289073A Expired GB1423065A (en) | 1972-07-21 | 1973-07-10 | D-6-methyl-2,8-disubstituted ergolines |
Country Status (24)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1517971A (en) * | 1974-07-19 | 1978-07-19 | Sandoz Ltd | 8alpha-substituted ergoline i derivatives |
| US3968111A (en) * | 1974-12-06 | 1976-07-06 | Eli Lilly And Company | 8,8-Disubstituted-6-methylergolines and related compounds |
| 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 |
| ATE107647T1 (de) * | 1984-04-09 | 1994-07-15 | Schering Ag | 2-substituierte ergolin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel. |
| HU196598B (en) * | 1986-04-25 | 1988-12-28 | Richter Gedeon Vegyeszet | Process for producing 1- and/or 8-substituted 2-halogenated ergoline derivatives and pharmaceutics comprising such compounds |
| DE3620293A1 (de) * | 1986-06-16 | 1987-12-17 | Schering Ag | 1-und/oder 2-substituierte ergolinderivate |
| JPH0596382U (ja) * | 1992-05-28 | 1993-12-27 | イビデン株式会社 | ドアユニット |
-
1973
- 1973-01-01 AR AR249167A patent/AR206772A1/es active
- 1973-07-10 ZA ZA734627A patent/ZA734627B/xx unknown
- 1973-07-10 GB GB3289073A patent/GB1423065A/en not_active Expired
- 1973-07-12 IL IL42730A patent/IL42730A/en unknown
- 1973-07-12 IL IL48288A patent/IL48288A/en unknown
- 1973-07-12 SE SE7309781A patent/SE393111B/xx unknown
- 1973-07-13 DE DE2365974A patent/DE2365974A1/de not_active Withdrawn
- 1973-07-13 DE DE2335750A patent/DE2335750C3/de not_active Expired
- 1973-07-17 NL NL7309969A patent/NL7309969A/xx not_active Application Discontinuation
- 1973-07-17 YU YU1945/73A patent/YU36953B/xx unknown
- 1973-07-18 PH PH14835A patent/PH11229A/en unknown
- 1973-07-19 DK DK399873AA patent/DK140986B/da unknown
- 1973-07-19 BE BE1005246A patent/BE802531A/xx not_active IP Right Cessation
- 1973-07-19 HU HUEI485A patent/HU167274B/hu unknown
- 1973-07-20 BG BG26855A patent/BG21411A3/xx unknown
- 1973-07-20 CS CS735239A patent/CS208164B2/cs unknown
- 1973-07-20 RO RO7300083213A patent/RO63792A/ro unknown
- 1973-07-20 CH CH391076A patent/CH580625A5/xx not_active IP Right Cessation
- 1973-07-20 AT AT643473A patent/AT331425B/de not_active IP Right Cessation
- 1973-07-20 CA CA177,021A patent/CA1006159A/en not_active Expired
- 1973-07-20 BG BG024148A patent/BG21410A3/xx unknown
- 1973-07-20 IE IE1238/73A patent/IE37936B1/xx unknown
- 1973-07-20 FR FR7326708A patent/FR2193606B1/fr not_active Expired
- 1973-07-20 ES ES417078A patent/ES417078A1/es not_active Expired
- 1973-07-20 CH CH391276A patent/CH580626A5/xx not_active IP Right Cessation
- 1973-07-20 SU SU731948966A patent/SU645581A3/ru active
- 1973-07-20 CH CH391176A patent/CH578563A5/xx not_active IP Right Cessation
- 1973-07-20 RO RO7375548A patent/RO71305A/ro unknown
- 1973-07-20 CH CH1067873A patent/CH581135A5/xx not_active IP Right Cessation
- 1973-07-20 DD DD172402A patent/DD107690A5/xx unknown
- 1973-07-20 CH CH391376A patent/CH578564A5/xx not_active IP Right Cessation
- 1973-07-20 BG BG028443A patent/BG22400A3/xx unknown
- 1973-07-20 JP JP8074973A patent/JPS576431B2/ja not_active Expired
-
1974
- 1974-01-01 AR AR252738A patent/AR206887A1/es active
- 1974-12-04 SU SU7402080295A patent/SU584780A3/ru active
-
1975
- 1975-01-14 SU SU7502098198A patent/SU575029A3/ru active
- 1975-01-30 AR AR257473A patent/AR210072A1/es active
- 1975-10-13 IL IL48288A patent/IL48288A0/xx unknown
- 1975-11-21 ES ES442887A patent/ES442887A1/es not_active Expired
- 1975-11-21 ES ES442886A patent/ES442886A1/es not_active Expired
- 1975-11-21 ES ES442885A patent/ES442885A1/es not_active Expired
-
1976
- 1976-04-07 ES ES446789A patent/ES446789A1/es not_active Expired
- 1976-10-15 SE SE7611466A patent/SE410459B/xx unknown
- 1976-10-15 SE SE7611467A patent/SE410603B/xx unknown
-
1981
- 1981-08-07 JP JP56123937A patent/JPS5813541B2/ja not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |