CH652719A5 - Ergoline derivatives, their preparation and use - Google Patents
Ergoline derivatives, their preparation and use Download PDFInfo
- Publication number
- CH652719A5 CH652719A5 CH862/83A CH86283A CH652719A5 CH 652719 A5 CH652719 A5 CH 652719A5 CH 862/83 A CH862/83 A CH 862/83A CH 86283 A CH86283 A CH 86283A CH 652719 A5 CH652719 A5 CH 652719A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compound
- acid addition
- addition salts
- compounds
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- 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 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 102000015554 Dopamine receptor Human genes 0.000 claims abstract description 3
- 108050004812 Dopamine receptor Proteins 0.000 claims abstract description 3
- 230000004936 stimulating effect Effects 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 241000700159 Rattus Species 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 230000003291 dopaminomimetic effect Effects 0.000 claims description 5
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 230000028327 secretion Effects 0.000 claims description 4
- 238000007920 subcutaneous administration Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 238000002513 implantation Methods 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- 208000027089 Parkinsonian disease Diseases 0.000 claims description 2
- 206010034010 Parkinsonism Diseases 0.000 claims description 2
- 102000003946 Prolactin Human genes 0.000 claims description 2
- 108010057464 Prolactin Proteins 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 230000001263 anti-prolactin effect Effects 0.000 claims description 2
- DCBDOYDVQJVXOH-UHFFFAOYSA-N azane;1h-indole Chemical compound N.C1=CC=C2NC=CC2=C1 DCBDOYDVQJVXOH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229960003638 dopamine Drugs 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000002474 experimental method Methods 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 229940097325 prolactin Drugs 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 210000003523 substantia nigra Anatomy 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- VBDRBXHZZQMXPV-FBBABVLZSA-N C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(CC)CC)=C3C2=CN(C(C)C)C3=C1 Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(CC)CC)=C3C2=CN(C(C)C)C3=C1 VBDRBXHZZQMXPV-FBBABVLZSA-N 0.000 abstract 1
- 238000007126 N-alkylation reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 208000031424 hyperprolactinemia Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005406 washing 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
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH862/83A CH652719A5 (en) | 1983-02-16 | 1983-02-16 | Ergoline derivatives, their preparation and use |
| HU84463A HU196399B (en) | 1983-02-16 | 1984-02-03 | Process for producing ergoline derivatives and pharmaceutical compositions comprising such compounds |
| NL8400333A NL8400333A (nl) | 1983-02-16 | 1984-02-03 | Moederkoornalkaloiden, hun bereiding en hun toepassing. |
| DE19843404400 DE3404400A1 (de) | 1983-02-16 | 1984-02-08 | Mutterkornalkoloide, ihre herstellung und verwendung |
| FR8402128A FR2540874B1 (fr) | 1983-02-16 | 1984-02-09 | Nouveaux derives de l'acide lysergique, leur preparation et leur utilisation comme medicaments |
| PL24623084A PL246230A1 (en) | 1983-02-16 | 1984-02-13 | Process for preparing ergot alkaloids |
| GB08403723A GB2135307B (en) | 1983-02-16 | 1984-02-13 | Ergot derivatives |
| IT47681/84A IT1199062B (it) | 1983-02-16 | 1984-02-14 | Derivati della segale cornuta,loro preparazione e loro impiego come medicamenti |
| FI840587A FI80034C (fi) | 1983-02-16 | 1984-02-14 | Foerfarande foer framstaellning av terapeutiskt anvaendbara mjoeldrygaalkaloider. |
| DK67284A DK67284A (da) | 1983-02-16 | 1984-02-14 | Meldroejealkaloider |
| PH30239A PH24707A (en) | 1983-02-16 | 1984-02-14 | Ergot derivatives |
| CA000447409A CA1208630A (en) | 1983-02-16 | 1984-02-14 | Ergot derivatives |
| NZ207145A NZ207145A (en) | 1983-02-16 | 1984-02-14 | Ergot derivatives and pharmaceutical compositions |
| IL70954A IL70954A (en) | 1983-02-16 | 1984-02-14 | N,n-diethyl-n'-((8 alpha)-1-ethyl(or isopropyl)-6-methylergolin-8-yl)sulfamide,their production and pharmaceutical compositions containing them |
| SE8400782A SE459970B (sv) | 1983-02-16 | 1984-02-14 | Ergolin-8-yl-sulfamid, saett att framstaella denna och en farmaceutisk komposition |
| PT78101A PT78101B (en) | 1983-02-16 | 1984-02-14 | Process for the preparation of ergot derivatives |
| GR73799A GR81770B (enrdf_load_stackoverflow) | 1983-02-16 | 1984-02-14 | |
| AT0047984A AT386410B (de) | 1983-02-16 | 1984-02-15 | Verfahren zur herstellung von neuen ergolinderivaten |
| IE353/84A IE56871B1 (en) | 1983-02-16 | 1984-02-15 | Ergot derivatives |
| JP59027989A JPS59155382A (ja) | 1983-02-16 | 1984-02-15 | 麦角アルカロイド誘導体 |
| AU24625/84A AU572822B2 (en) | 1983-02-16 | 1984-02-15 | N,n-diethyl-ergolin-8-yl-sulphamide |
| ES529759A ES8505252A1 (es) | 1983-02-16 | 1984-02-15 | Procedimiento para preparar derivados del cornezuelo del centeno |
| ZA841150A ZA841150B (en) | 1983-02-16 | 1984-02-16 | Ergot derivatives |
| US06/936,204 US4791116A (en) | 1983-02-16 | 1986-12-01 | N,N-diethyl-N'-[(8α)-1-ethyl-6-methyl-ergolin-8-yl]-sulfamide useful as prolactin secretion inhibitor, anti-parkinson agents and anti-depressant agents |
| MY270/87A MY8700270A (en) | 1983-02-16 | 1987-12-30 | Ergot derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH862/83A CH652719A5 (en) | 1983-02-16 | 1983-02-16 | Ergoline derivatives, their preparation and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH652719A5 true CH652719A5 (en) | 1985-11-29 |
Family
ID=4196915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH862/83A CH652719A5 (en) | 1983-02-16 | 1983-02-16 | Ergoline derivatives, their preparation and use |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS59155382A (enrdf_load_stackoverflow) |
| CH (1) | CH652719A5 (enrdf_load_stackoverflow) |
| ZA (1) | ZA841150B (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2656344A1 (de) * | 1975-12-23 | 1977-07-07 | Sandoz Ag | Ergolinderivate, ihre verwendung und herstellung |
-
1983
- 1983-02-16 CH CH862/83A patent/CH652719A5/de not_active IP Right Cessation
-
1984
- 1984-02-15 JP JP59027989A patent/JPS59155382A/ja active Granted
- 1984-02-16 ZA ZA841150A patent/ZA841150B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0346471B2 (enrdf_load_stackoverflow) | 1991-07-16 |
| JPS59155382A (ja) | 1984-09-04 |
| ZA841150B (en) | 1985-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |