NO136643B - - Google Patents
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- Publication number
- NO136643B NO136643B NO4351/72A NO435172A NO136643B NO 136643 B NO136643 B NO 136643B NO 4351/72 A NO4351/72 A NO 4351/72A NO 435172 A NO435172 A NO 435172A NO 136643 B NO136643 B NO 136643B
- Authority
- NO
- Norway
- Prior art keywords
- ergoline
- dimethyl
- methyl
- pyrimidinoaminomethyl
- guanidinomethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- -1 methoxy, ethoxy, phenyl Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 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 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910002651 NO3 Inorganic materials 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000002908 adrenolytic effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 description 3
- 229960004704 dihydroergotamine Drugs 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UNELDXFWWQRODL-IUODEOHRSA-N (6ar,10ar)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2CCCN([C@@H]2C2)C)=C3C2=CN(C)C3=C1 UNELDXFWWQRODL-IUODEOHRSA-N 0.000 description 1
- ZZUFFOQIEWLWAY-UHFFFAOYSA-N 1-(thiophen-2-ylmethyl)piperazine;dihydrochloride Chemical compound Cl.Cl.C=1C=CSC=1CN1CCNCC1 ZZUFFOQIEWLWAY-UHFFFAOYSA-N 0.000 description 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- GAZRNXIMWKZADY-UHFFFAOYSA-N 3,5-dimethylpyrazole-1-carboximidamide Chemical compound CC=1C=C(C)N(C(N)=N)N=1 GAZRNXIMWKZADY-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 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 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RHGUXDUPXYFCTE-ZWNOBZJWSA-N ergoline Chemical compound C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=CNC3=C1 RHGUXDUPXYFCTE-ZWNOBZJWSA-N 0.000 description 1
- JIQJLQBLUARLNV-UHFFFAOYSA-N ethyl carbamimidothioate;hydrochloride Chemical compound Cl.CCSC(N)=N JIQJLQBLUARLNV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
- 229960003642 nicergoline Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- VFIZBHJTOHUOEK-UHFFFAOYSA-N s-ethylisothiourea Chemical compound CCSC(N)=N VFIZBHJTOHUOEK-UHFFFAOYSA-N 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003033 spasmogenic effect Effects 0.000 description 1
- 201000010653 vesiculitis Diseases 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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 |
|---|---|---|---|
| IT3193271 | 1971-12-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO136643B true NO136643B (enrdf_load_stackoverflow) | 1977-07-04 |
| NO136643C NO136643C (no) | 1977-10-12 |
Family
ID=11234509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4351/72A NO136643C (no) | 1971-12-02 | 1972-11-28 | Analogifremgangsm}te ved fremstilling av nye terapeutisk aktive ergolinderivater. |
Country Status (20)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7416120A (nl) * | 1973-12-21 | 1975-06-24 | Farmaceutici Italia | Werkwijze voor het bereiden van pyrimidinoami- nomethylergolinederivaten. |
-
0
- BE BE792188D patent/BE792188A/xx not_active IP Right Cessation
-
1972
- 1972-11-22 NL NL727215817A patent/NL153197B/xx not_active IP Right Cessation
- 1972-11-27 SU SU721851316A patent/SU617014A3/ru active
- 1972-11-27 GB GB5474372A patent/GB1357238A/en not_active Expired
- 1972-11-28 IL IL40944A patent/IL40944A/en unknown
- 1972-11-28 AT AT1011572A patent/AT321478B/de active
- 1972-11-28 NO NO4351/72A patent/NO136643C/no unknown
- 1972-11-28 CA CA157,696A patent/CA975773A/en not_active Expired
- 1972-11-28 IE IE1653/72A patent/IE37429B1/xx unknown
- 1972-11-28 AU AU49351/72A patent/AU465155B2/en not_active Expired
- 1972-11-29 FR FR7242381A patent/FR2162045A1/fr active Granted
- 1972-11-29 ZA ZA728459A patent/ZA728459B/xx unknown
- 1972-11-29 DK DK595972AA patent/DK138689B/da unknown
- 1972-11-29 SE SE7215545A patent/SE385301B/xx unknown
- 1972-11-30 CS CS8190A patent/CS173612B2/cs unknown
- 1972-11-30 JP JP11945772A patent/JPS5634597B2/ja not_active Expired
- 1972-12-01 DE DE2259012A patent/DE2259012C3/de not_active Expired
- 1972-12-01 HU HUFA933A patent/HU165530B/hu unknown
- 1972-12-01 ES ES409189A patent/ES409189A1/es not_active Expired
- 1972-12-01 CH CH1756672A patent/CH590276A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL40944A (en) | 1976-04-30 |
| NL7215817A (enrdf_load_stackoverflow) | 1973-06-05 |
| AU465155B2 (en) | 1975-09-18 |
| NO136643C (no) | 1977-10-12 |
| DE2259012C3 (de) | 1978-09-21 |
| ZA728459B (en) | 1973-09-26 |
| CA975773A (en) | 1975-10-07 |
| FR2162045A1 (en) | 1973-07-13 |
| CH590276A5 (enrdf_load_stackoverflow) | 1977-07-29 |
| DK138689C (enrdf_load_stackoverflow) | 1979-03-19 |
| JPS5634597B2 (enrdf_load_stackoverflow) | 1981-08-11 |
| HU165530B (enrdf_load_stackoverflow) | 1974-09-28 |
| FR2162045B1 (enrdf_load_stackoverflow) | 1976-06-11 |
| ES409189A1 (es) | 1976-01-01 |
| DK138689B (da) | 1978-10-16 |
| DE2259012A1 (de) | 1973-06-07 |
| CS173612B2 (enrdf_load_stackoverflow) | 1977-02-28 |
| JPS4862800A (enrdf_load_stackoverflow) | 1973-09-01 |
| AT321478B (de) | 1975-04-10 |
| SU617014A3 (ru) | 1978-07-25 |
| DE2259012B2 (de) | 1978-02-09 |
| IE37429L (en) | 1973-06-02 |
| SE385301B (sv) | 1976-06-21 |
| NL153197B (nl) | 1977-05-16 |
| AU4935172A (en) | 1974-05-30 |
| BE792188A (fr) | 1973-06-01 |
| GB1357238A (en) | 1974-06-19 |
| IL40944A0 (en) | 1973-01-30 |
| IE37429B1 (en) | 1977-07-20 |
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