SE466016B - Ergolinderivat och syraadditionssalter daerav - Google Patents
Ergolinderivat och syraadditionssalter daeravInfo
- Publication number
- SE466016B SE466016B SE8600786A SE8600786A SE466016B SE 466016 B SE466016 B SE 466016B SE 8600786 A SE8600786 A SE 8600786A SE 8600786 A SE8600786 A SE 8600786A SE 466016 B SE466016 B SE 466016B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- mixture
- activity
- added
- ylmethyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 title claims description 10
- 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 claims description 7
- -1 2-oxooxazolidin-3-yl group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 64
- 239000000203 mixture Substances 0.000 description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 230000000694 effects Effects 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 241000700159 Rattus Species 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 13
- 239000012312 sodium hydride Substances 0.000 description 13
- 229910000104 sodium hydride Inorganic materials 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- DEHHSXGUVDBSAH-BSLALVQMSA-N [(6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]methyl 4-methylbenzenesulfonate Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C)OS(=O)(=O)C1=CC=C(C)C=C1 DEHHSXGUVDBSAH-BSLALVQMSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 230000000767 anti-ulcer Effects 0.000 description 6
- 239000000935 antidepressant agent Substances 0.000 description 6
- 210000004556 brain Anatomy 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 230000001430 anti-depressive effect Effects 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- QHZUABXEBRGBLP-LKWYKXIFSA-N (6aR,9R,10aR)-N-[(2R,4R,9aS,9bR)-4-benzyl-9b-hydroxy-3,5-dioxo-2-propan-2-yl-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR,9R,10aR)-N-[(2R,4R,9aS,9bR)-9b-hydroxy-3,5-dioxo-2,4-di(propan-2-yl)-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR,10aR)-N-[(2S,4S,9bS)-9b-hydroxy-4-(2-methylpropyl)-3,5-dioxo-2-propan-2-yl-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)C4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2CC(CN(C)[C@@H]2C2)C(=O)N[C@@]3(C(=O)C4[C@@H](C(N5CCCC5[C@@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(C21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 QHZUABXEBRGBLP-LKWYKXIFSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229920000084 Gum arabic Polymers 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 241000978776 Senegalia senegal Species 0.000 description 4
- 239000000205 acacia gum Substances 0.000 description 4
- 235000010489 acacia gum Nutrition 0.000 description 4
- 230000003276 anti-hypertensive effect Effects 0.000 description 4
- 210000004051 gastric juice Anatomy 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 210000002784 stomach Anatomy 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 3
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- FHRSHSOEWXUORL-HDJSIYSDSA-N cetraxate Chemical compound C1C[C@@H](C[NH3+])CC[C@@H]1C(=O)OC1=CC=C(CCC([O-])=O)C=C1 FHRSHSOEWXUORL-HDJSIYSDSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 229960005384 hydralazine hydrochloride Drugs 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 3
- 229960003147 reserpine Drugs 0.000 description 3
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 3
- 230000003248 secreting effect Effects 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- AWFYPPSBLUWMFQ-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=C2 AWFYPPSBLUWMFQ-UHFFFAOYSA-N 0.000 description 2
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 description 2
- MKBBSFGKFMQPPC-UHFFFAOYSA-N 2-propyl-1h-imidazole Chemical compound CCCC1=NC=CN1 MKBBSFGKFMQPPC-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- NNDATQSUZGLGQT-BXUZGUMPSA-N 6-methylergoline Chemical compound C1=CC([C@H]2CCCN([C@@H]2C2)C)=C3C2=CNC3=C1 NNDATQSUZGLGQT-BXUZGUMPSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Chemical compound CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- UFKTZIXVYHGAES-WDBKCZKBSA-N [(6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]methanol Chemical compound C1=CC([C@H]2C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 UFKTZIXVYHGAES-WDBKCZKBSA-N 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
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- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
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- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
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- 239000003610 charcoal Substances 0.000 description 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 2
- 229960001380 cimetidine Drugs 0.000 description 2
- MFFWLPUTVHVELN-UHFFFAOYSA-N dichloromethane;propan-2-yl acetate Chemical compound ClCCl.CC(C)OC(C)=O MFFWLPUTVHVELN-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- CCQPIEFHOTZURZ-XFQXTVEOSA-N ethyl 1-[[(6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]methyl]-5-methylimidazole-4-carboxylate Chemical compound CC1=C(C(=O)OCC)N=CN1C[C@H]1CN(C)[C@H](CC=2C3=C4C=CC=C3NC=2)[C@@H]4C1 CCQPIEFHOTZURZ-XFQXTVEOSA-N 0.000 description 2
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- VLDUBDZWWNLZCU-UHFFFAOYSA-N ethyl 5-methyl-1h-imidazole-4-carboxylate Chemical compound CCOC(=O)C=1NC=NC=1C VLDUBDZWWNLZCU-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
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- 239000004615 ingredient Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
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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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3343085 | 1985-02-21 | ||
| JP29920385A JPH0699429B2 (ja) | 1985-02-21 | 1985-12-28 | エルゴリン誘導体およびその酸付加塩 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8600786D0 SE8600786D0 (sv) | 1986-02-20 |
| SE8600786L SE8600786L (sv) | 1986-08-22 |
| SE466016B true SE466016B (sv) | 1991-12-02 |
Family
ID=26372109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8600786A SE466016B (sv) | 1985-02-21 | 1986-02-20 | Ergolinderivat och syraadditionssalter daerav |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4713457A (fr) |
| AU (1) | AU591094B2 (fr) |
| BE (1) | BE904254A (fr) |
| CA (1) | CA1292736C (fr) |
| CH (1) | CH666270A5 (fr) |
| DE (1) | DE3605676C2 (fr) |
| ES (1) | ES8704502A1 (fr) |
| FR (1) | FR2577553B1 (fr) |
| GB (1) | GB2173189B (fr) |
| HU (1) | HU195655B (fr) |
| IT (1) | IT1203744B (fr) |
| NL (1) | NL8600430A (fr) |
| SE (1) | SE466016B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8714767D0 (en) * | 1987-06-24 | 1987-07-29 | Erba Farmitalia | Egoline derivatives |
| GB8617907D0 (en) * | 1986-07-22 | 1986-08-28 | Erba Farmitalia | Tetracyclic indole derivatives |
| GB8702364D0 (en) * | 1987-02-03 | 1987-03-11 | Erba Farmitalia | Ergolinyl heterocycles |
| GB9006772D0 (en) * | 1990-03-27 | 1990-05-23 | Erba Carlo Spa | 4-piperidinyl-ergoline derivatives |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH551976A (de) * | 1971-05-19 | 1974-07-31 | Sandoz Ag | Verfahren zur herstellung neuer 6-methyl-8(beta)-(ureidomethyl) ergolen-derivate. |
| CH551975A (de) * | 1971-05-19 | 1974-07-31 | Sandoz Ag | Verfahren zur herstellung neuer 6-methyl-8(beta)-(ureidomethyl) ergolen-derivate. |
| US4199579A (en) * | 1975-03-14 | 1980-04-22 | Siphar S. A. | Carbamates of 2-haloergolines and 2-haloergolenes and process for the preparation thereof |
| HU172649B (hu) * | 1975-04-24 | 1978-11-28 | Gyogyszerkutato Intezet | Sposob poluchenija novykh biologicheski aktivnykh lizergamidov |
| YU39278B (en) * | 1976-12-22 | 1984-10-31 | Lek Tovarna Farmacevtskih | Process for preparing 5-bromo nicotinic acid esters |
| DE2802023A1 (de) * | 1977-01-28 | 1978-08-03 | Sandoz Ag | Neue ergotderivate, ihre herstellung und verwendung |
| CH628049A5 (en) * | 1977-03-25 | 1982-02-15 | Sandoz Ag | Process for the preparation of ergolene derivatives |
| YU216177A (en) * | 1977-09-09 | 1984-02-29 | Rudolf Rucman | Process for preparing 2-bromo ergosine |
| US4166182A (en) * | 1978-02-08 | 1979-08-28 | Eli Lilly And Company | 6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds |
| FR2421176A1 (fr) * | 1978-03-29 | 1979-10-26 | Sandoz Sa | Nouveaux derives de l'ergot de seigle, leur preparation et leur application comme medicaments |
| YU40046B (en) * | 1978-09-04 | 1985-06-30 | Lek Tovarna Farmacevtskih | Process for preparing 2-bromo-9,10-dihydroergosine |
| YU40533B (en) * | 1978-09-04 | 1986-02-28 | Lek Tovarna Farmacevtskih | Process for preparing 2-bromoergosinine |
| AU526764B2 (en) * | 1978-09-08 | 1983-01-27 | Farmitalia Carlo Erba S.P.A. | Ergoline derivatives |
| HU180467B (en) * | 1979-07-12 | 1983-03-28 | Gyogyszerkutato Intezet | Process for producing new ergol-8-ene- and ergoline-sceleted compounds |
| GB2056437A (en) * | 1979-08-07 | 1981-03-18 | Erba Farmitalia | Secoergoline derivatives |
| ZA812103B (en) * | 1980-04-03 | 1982-04-28 | Erba Farmitalia | Ergoline derivatives |
| NL189462C (nl) * | 1980-04-03 | 1993-04-16 | Erba Carlo Spa | Ergolinederivaten met antiprolactinische en/of antihypertensieve eigenschappen en farmaceutische preparaat daarvan. |
| DE3101535A1 (de) * | 1981-01-14 | 1982-08-12 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue (2-halogen-ergolinyl)-n'.n'-diethyl-harnstoffderivate, verfahren zu ihrer herstellung und deren verwendung als arzneimittel |
| CH645894A5 (en) * | 1981-02-24 | 1984-10-31 | Sandoz Ag | Ergoline derivatives, their preparation and use |
| GB2112382B (en) * | 1981-11-06 | 1985-03-06 | Erba Farmitalia | Ergoline derivatives |
| GB2120242A (en) * | 1982-04-30 | 1983-11-30 | Erba Farmitalia | Ergoline derivatives |
| HU190105B (en) * | 1983-06-03 | 1986-08-28 | Gyogyszerkutato Intezet | Process for production of pirazolyl-methyl-ergolin- derivatives and their acid additional salts |
| DE3309493A1 (de) * | 1983-03-14 | 1984-09-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Neue ergolin-derivate, verfahren zu ihrer herstellung sowie verwendung als arzneimittel |
| GB8311679D0 (en) * | 1983-04-28 | 1983-06-02 | Erba Farmitalia | Ergoline derivatives |
| PH21123A (en) * | 1983-04-28 | 1987-07-27 | Erba Farmitalia | Ergoline derivatives |
-
1986
- 1986-02-12 GB GB08603442A patent/GB2173189B/en not_active Expired
- 1986-02-13 AU AU53465/86A patent/AU591094B2/en not_active Ceased
- 1986-02-19 CA CA000502188A patent/CA1292736C/fr not_active Expired - Lifetime
- 1986-02-20 BE BE0/216288A patent/BE904254A/fr not_active IP Right Cessation
- 1986-02-20 IT IT47672/86A patent/IT1203744B/it active
- 1986-02-20 HU HU86711A patent/HU195655B/hu not_active IP Right Cessation
- 1986-02-20 CH CH682/86A patent/CH666270A5/de not_active IP Right Cessation
- 1986-02-20 SE SE8600786A patent/SE466016B/sv not_active IP Right Cessation
- 1986-02-20 NL NL8600430A patent/NL8600430A/nl not_active Application Discontinuation
- 1986-02-21 DE DE3605676A patent/DE3605676C2/de not_active Expired - Fee Related
- 1986-02-21 FR FR868602440A patent/FR2577553B1/fr not_active Expired - Lifetime
- 1986-02-21 US US06/831,676 patent/US4713457A/en not_active Expired - Fee Related
- 1986-02-21 ES ES552258A patent/ES8704502A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB8603442D0 (en) | 1986-03-19 |
| SE8600786L (sv) | 1986-08-22 |
| HUT40121A (en) | 1986-11-28 |
| DE3605676A1 (de) | 1986-09-18 |
| BE904254A (fr) | 1986-06-16 |
| AU591094B2 (en) | 1989-11-30 |
| FR2577553A1 (fr) | 1986-08-22 |
| US4713457A (en) | 1987-12-15 |
| DE3605676C2 (de) | 1998-04-09 |
| ES8704502A1 (es) | 1987-04-16 |
| NL8600430A (nl) | 1986-09-16 |
| ES552258A0 (es) | 1987-04-16 |
| GB2173189B (en) | 1988-04-27 |
| CH666270A5 (de) | 1988-07-15 |
| GB2173189A (en) | 1986-10-08 |
| CA1292736C (fr) | 1991-12-03 |
| FR2577553B1 (fr) | 1991-06-21 |
| HU195655B (en) | 1988-06-28 |
| IT8647672A0 (it) | 1986-02-20 |
| IT1203744B (it) | 1989-02-23 |
| SE8600786D0 (sv) | 1986-02-20 |
| AU5346586A (en) | 1986-08-28 |
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