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)
Abstract
1423065 D-6-Methyl-2,8-disubstituted ergoline ELI LILLY & CO 10 July 1973 [21 July 1972] 32890/73 Heading C2C Novel D-6-methyl-2,8-disubstituted ergoline compounds of the Formula (I) wherein X is halo, methyl or CN and R is CH 2 CN or CH 2 CONH 2 and their salts formed with pharmaceutically acceptable acids may be obtained (where X is halo) by reacting a compound of formula wherein R<SP>1</SP> is Cl, Br, I, O-SO 2 -CH 3 or O-SO 2 -p-tolyl; with a positive halogenating agent containing positive chlorine, bromine or iodine, to yield a compound of formula and then reacting this with an inorganic cyanide in an inert solvent. Conversion of the cyano group to the amide can be effected by well known procedures. Compounds in which X is CH 3 can be prepared by reacting D-6-methyl- 8-cyanomethyl (or 8-carboxamidomethyl)ergoline with methyl formate and ethanedithiol to form a dithioethylene acetal and desulphurizing the latter to form the 2-methyl derivative. Compounds in which X is CN can be prepared by reaction of a 2-unsubstituted ergoline with chlorosulphonylisocyanate and triethylamine. Pharmaceutical composition for inhibiting the secretion of prolactin in mammals contains as active ingredient a compound of Formula (I) or a salt thereof in forms suitable for oral or parenteral administration.
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)
| Country | Link |
|---|---|
| JP (2) | JPS576431B2 (en) |
| AR (3) | AR206772A1 (en) |
| AT (1) | AT331425B (en) |
| BE (1) | BE802531A (en) |
| BG (3) | BG22400A3 (en) |
| CA (1) | CA1006159A (en) |
| CH (5) | CH578564A5 (en) |
| CS (1) | CS208164B2 (en) |
| DD (1) | DD107690A5 (en) |
| DE (2) | DE2365974A1 (en) |
| DK (1) | DK140986B (en) |
| ES (5) | ES417078A1 (en) |
| FR (1) | FR2193606B1 (en) |
| GB (1) | GB1423065A (en) |
| HU (1) | HU167274B (en) |
| IE (1) | IE37936B1 (en) |
| IL (3) | IL42730A (en) |
| NL (1) | NL7309969A (en) |
| PH (1) | PH11229A (en) |
| RO (2) | RO63792A (en) |
| SE (3) | SE393111B (en) |
| SU (3) | SU645581A3 (en) |
| YU (1) | YU36953B (en) |
| ZA (1) | ZA734627B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1517972A (en) * | 1974-07-19 | 1978-07-19 | Sandoz Ltd | 6-methyl-8alpha-cyanomethylergoline i |
| 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 |
| EP0160842B1 (en) * | 1984-04-09 | 1994-06-22 | Schering Aktiengesellschaft | 2-Substituted ergoline derivatives, processes for their preparation, and their use as medicaments |
| 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 (en) * | 1986-06-16 | 1987-12-17 | Schering Ag | 1 AND / OR 2 SUBSTITUTED ERGOL DERIVATIVES |
| JPH0596382U (en) * | 1992-05-28 | 1993-12-27 | イビデン株式会社 | Door unit |
-
1973
- 1973-01-01 AR AR249167A patent/AR206772A1/en active
- 1973-07-10 GB GB3289073A patent/GB1423065A/en not_active Expired
- 1973-07-10 ZA ZA734627A patent/ZA734627B/en unknown
- 1973-07-12 IL IL42730A patent/IL42730A/en unknown
- 1973-07-12 SE SE7309781A patent/SE393111B/en unknown
- 1973-07-12 IL IL48288A patent/IL48288A/en unknown
- 1973-07-13 DE DE2365974A patent/DE2365974A1/en not_active Withdrawn
- 1973-07-13 DE DE2335750A patent/DE2335750C3/en not_active Expired
- 1973-07-17 YU YU1945/73A patent/YU36953B/en unknown
- 1973-07-17 NL NL7309969A patent/NL7309969A/xx not_active Application Discontinuation
- 1973-07-18 PH PH14835A patent/PH11229A/en unknown
- 1973-07-19 HU HUEI485A patent/HU167274B/hu unknown
- 1973-07-19 DK DK399873AA patent/DK140986B/en unknown
- 1973-07-19 BE BE1005246A patent/BE802531A/en not_active IP Right Cessation
- 1973-07-20 FR FR7326708A patent/FR2193606B1/fr not_active Expired
- 1973-07-20 BG BG028443A patent/BG22400A3/en unknown
- 1973-07-20 RO RO7300083213A patent/RO63792A/en unknown
- 1973-07-20 CH CH391376A patent/CH578564A5/xx not_active IP Right Cessation
- 1973-07-20 CA CA177,021A patent/CA1006159A/en not_active Expired
- 1973-07-20 BG BG024148A patent/BG21410A3/en unknown
- 1973-07-20 DD DD172402A patent/DD107690A5/xx unknown
- 1973-07-20 CH CH391176A patent/CH578563A5/xx not_active IP Right Cessation
- 1973-07-20 CH CH391276A patent/CH580626A5/xx not_active IP Right Cessation
- 1973-07-20 SU SU731948966A patent/SU645581A3/en active
- 1973-07-20 BG BG26855A patent/BG21411A3/xx unknown
- 1973-07-20 JP JP8074973A patent/JPS576431B2/ja not_active Expired
- 1973-07-20 IE IE1238/73A patent/IE37936B1/en unknown
- 1973-07-20 CH CH1067873A patent/CH581135A5/xx not_active IP Right Cessation
- 1973-07-20 RO RO7375548A patent/RO71305A/en unknown
- 1973-07-20 CS CS735239A patent/CS208164B2/en unknown
- 1973-07-20 AT AT643473A patent/AT331425B/en not_active IP Right Cessation
- 1973-07-20 CH CH391076A patent/CH580625A5/xx not_active IP Right Cessation
- 1973-07-20 ES ES417078A patent/ES417078A1/en not_active Expired
-
1974
- 1974-01-01 AR AR252738A patent/AR206887A1/en active
- 1974-12-04 SU SU7402080295A patent/SU584780A3/en active
-
1975
- 1975-01-14 SU SU7502098198A patent/SU575029A3/en active
- 1975-01-30 AR AR257473A patent/AR210072A1/en active
- 1975-10-13 IL IL48288A patent/IL48288A0/en unknown
- 1975-11-21 ES ES442885A patent/ES442885A1/en not_active Expired
- 1975-11-21 ES ES442887A patent/ES442887A1/en not_active Expired
- 1975-11-21 ES ES442886A patent/ES442886A1/en not_active Expired
-
1976
- 1976-04-07 ES ES446789A patent/ES446789A1/en not_active Expired
- 1976-10-15 SE SE7611466A patent/SE410459B/en unknown
- 1976-10-15 SE SE7611467A patent/SE410603B/en unknown
-
1981
- 1981-08-07 JP JP56123937A patent/JPS5813541B2/en 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 |