CS208164B2 - Method of making the d-2-halogene-6-methyl-8-kyan/carboxamido/methylergolines - Google Patents
Method of making the d-2-halogene-6-methyl-8-kyan/carboxamido/methylergolines Download PDFInfo
- Publication number
- CS208164B2 CS208164B2 CS735239A CS523973A CS208164B2 CS 208164 B2 CS208164 B2 CS 208164B2 CS 735239 A CS735239 A CS 735239A CS 523973 A CS523973 A CS 523973A CS 208164 B2 CS208164 B2 CS 208164B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- ergoline
- formula
- compounds
- compound
- Prior art date
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- 125000005518 carboxamido group Chemical group 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 11
- 150000007513 acids Chemical class 0.000 claims abstract description 8
- 239000000460 chlorine Substances 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- ZYACKOKSHZQYDS-NTVGDFDMSA-N (6ar,10ar)-9-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline Chemical class C1=CC([C@@H]2[C@H](NCC(C2)C)C2)=C3C2=CNC3=C1 ZYACKOKSHZQYDS-NTVGDFDMSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 34
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- 108010057464 Prolactin Proteins 0.000 abstract description 20
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- 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 description 10
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- 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
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 abstract 1
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- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
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- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000002622 gonadotropin Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000003400 hallucinatory effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical class CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 239000000960 hypophysis hormone Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 230000001294 luteotrophic effect Effects 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
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical class COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 108700029318 rat female Proteins 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 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
- 239000003981 vehicle Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 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
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS776672A CS208165B2 (cs) | 1972-07-21 | 1977-10-13 | Způsob výroby D-6-methyl-8-mesyIoxymethylergoIinu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27390272A | 1972-07-21 | 1972-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS208164B2 true CS208164B2 (en) | 1981-08-31 |
Family
ID=23045910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS735239A CS208164B2 (en) | 1972-07-21 | 1973-07-20 | Method of making the d-2-halogene-6-methyl-8-kyan/carboxamido/methylergolines |
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 |
| DE3587860D1 (de) * | 1984-04-09 | 1994-07-28 | 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 SE SE7309781A patent/SE393111B/xx unknown
- 1973-07-12 IL IL48288A patent/IL48288A/en unknown
- 1973-07-13 DE DE2335750A patent/DE2335750C3/de not_active Expired
- 1973-07-13 DE DE2365974A patent/DE2365974A1/de not_active Withdrawn
- 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 CH CH391276A patent/CH580626A5/xx not_active IP Right Cessation
- 1973-07-20 IE IE1238/73A patent/IE37936B1/xx unknown
- 1973-07-20 BG BG028443A patent/BG22400A3/xx unknown
- 1973-07-20 CH CH391176A patent/CH578563A5/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 CH CH391076A patent/CH580625A5/xx not_active IP Right Cessation
- 1973-07-20 FR FR7326708A patent/FR2193606B1/fr not_active Expired
- 1973-07-20 BG BG26855A patent/BG21411A3/xx unknown
- 1973-07-20 JP JP8074973A patent/JPS576431B2/ja not_active Expired
- 1973-07-20 RO RO7300083213A patent/RO63792A/ro unknown
- 1973-07-20 ES ES417078A patent/ES417078A1/es not_active Expired
- 1973-07-20 SU SU731948966A patent/SU645581A3/ru active
- 1973-07-20 BG BG024148A patent/BG21410A3/xx unknown
- 1973-07-20 RO RO7375548A patent/RO71305A/ro unknown
- 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 CH CH1067873A patent/CH581135A5/xx not_active IP Right Cessation
- 1973-07-20 CS CS735239A patent/CS208164B2/cs unknown
-
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 ES442885A patent/ES442885A1/es not_active Expired
- 1975-11-21 ES ES442886A patent/ES442886A1/es not_active Expired
-
1976
- 1976-04-07 ES ES446789A patent/ES446789A1/es not_active Expired
- 1976-10-15 SE SE7611467A patent/SE410603B/xx unknown
- 1976-10-15 SE SE7611466A patent/SE410459B/xx unknown
-
1981
- 1981-08-07 JP JP56123937A patent/JPS5813541B2/ja not_active Expired
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