NO320155B1 - Benzo(c)kinolizinderivater, deres fremstilling, farmasoytisk sammensetning som inneholder derivatene, og anvendelse av derivatene til a fremstille et legemiddel - Google Patents
Benzo(c)kinolizinderivater, deres fremstilling, farmasoytisk sammensetning som inneholder derivatene, og anvendelse av derivatene til a fremstille et legemiddel Download PDFInfo
- Publication number
- NO320155B1 NO320155B1 NO19983444A NO983444A NO320155B1 NO 320155 B1 NO320155 B1 NO 320155B1 NO 19983444 A NO19983444 A NO 19983444A NO 983444 A NO983444 A NO 983444A NO 320155 B1 NO320155 B1 NO 320155B1
- Authority
- NO
- Norway
- Prior art keywords
- benzo
- quinolizin
- group
- tetrahydro
- methyl
- Prior art date
Links
- UOGFZJRMCBHRQU-UHFFFAOYSA-N 10ah-benzo[c]quinolizine Chemical class N12C=CC=CC2=CC=C2C1C=CC=C2 UOGFZJRMCBHRQU-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
- 239000003814 drug Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 229940079593 drug Drugs 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 48
- WZCXJNBOOQLKKD-UHFFFAOYSA-N 2,4-dihydroquinolizin-3-one Chemical compound C1=CC=CN2CC(=O)CC=C21 WZCXJNBOOQLKKD-UHFFFAOYSA-N 0.000 claims description 16
- 108010044467 Isoenzymes Proteins 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- -1 silyl enol ethers Chemical class 0.000 claims description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 201000004384 Alopecia Diseases 0.000 claims description 3
- 206010020112 Hirsutism Diseases 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 230000003676 hair loss Effects 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- SNEPAAKJPPNOQM-UHFFFAOYSA-N 4,8-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC2=CC(C)=CC=C2N2C1=C(C)C(=O)CC2 SNEPAAKJPPNOQM-UHFFFAOYSA-N 0.000 claims description 2
- DXHLMUSXIWMQGZ-UHFFFAOYSA-N 4-methyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC2=CC=CC=C2N2C1=C(C)C(=O)CC2 DXHLMUSXIWMQGZ-UHFFFAOYSA-N 0.000 claims description 2
- GIOTXVLKTZEBCV-UHFFFAOYSA-N 5,6-dihydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3C=CC(=O)C=C3CCC2=C1 GIOTXVLKTZEBCV-UHFFFAOYSA-N 0.000 claims description 2
- KUTVZPSVMLYETM-UHFFFAOYSA-N 8-chloro-1-methyl-4,4a,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound ClC1=CC=C2N3C(C)=CC(=O)CC3CCC2=C1 KUTVZPSVMLYETM-UHFFFAOYSA-N 0.000 claims description 2
- DWGUKGCMIQALCV-UHFFFAOYSA-N 8-chloro-4-methyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC2=CC(Cl)=CC=C2N2C1=C(C)C(=O)CC2 DWGUKGCMIQALCV-UHFFFAOYSA-N 0.000 claims description 2
- QZQDAVNKWYDXLA-UHFFFAOYSA-N 8-methyl-1,2,4,4a,5,6-hexahydrobenzo[f]quinolizin-3-one Chemical compound C1CC(=O)CC2CCC3=CC(C)=CC=C3N21 QZQDAVNKWYDXLA-UHFFFAOYSA-N 0.000 claims description 2
- JZEHDLKGTVQWAJ-UHFFFAOYSA-N 8-methyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC(=O)C=C2CCC3=CC(C)=CC=C3N21 JZEHDLKGTVQWAJ-UHFFFAOYSA-N 0.000 claims description 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- 230000006315 carbonylation Effects 0.000 claims description 2
- 238000005810 carbonylation reaction Methods 0.000 claims description 2
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims description 2
- 239000012434 nucleophilic reagent Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- OPJKPSOLCGGXEW-UHFFFAOYSA-N 1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3CCC(=O)C=C3CCC2=C1 OPJKPSOLCGGXEW-UHFFFAOYSA-N 0.000 claims 1
- OTIXIJWINAVPQQ-UHFFFAOYSA-N 1-methyl-1,2,4,4a,5,6-hexahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3C(C)CC(=O)CC3CCC2=C1 OTIXIJWINAVPQQ-UHFFFAOYSA-N 0.000 claims 1
- SPMRKOLVFPPPIE-UHFFFAOYSA-N 1-methyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3C(C)CC(=O)C=C3CCC2=C1 SPMRKOLVFPPPIE-UHFFFAOYSA-N 0.000 claims 1
- LNTWPSKEEYNUKK-UHFFFAOYSA-N 4,4a,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC2=CC=CC=C2N2C1CC(=O)C=C2 LNTWPSKEEYNUKK-UHFFFAOYSA-N 0.000 claims 1
- IRPKYFAHXYJVSA-UHFFFAOYSA-N 8-chloro-1,2,4,4a,5,6-hexahydrobenzo[f]quinolizin-3-one Chemical compound C1CC(=O)CC2CCC3=CC(Cl)=CC=C3N21 IRPKYFAHXYJVSA-UHFFFAOYSA-N 0.000 claims 1
- BRTGJFMJRRWDTL-UHFFFAOYSA-N 8-chloro-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC(=O)C=C2CCC3=CC(Cl)=CC=C3N21 BRTGJFMJRRWDTL-UHFFFAOYSA-N 0.000 claims 1
- MIDWATCAIIMLGJ-UHFFFAOYSA-N 8-chloro-4,4a,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC(=O)CC2CCC3=CC(Cl)=CC=C3N21 MIDWATCAIIMLGJ-UHFFFAOYSA-N 0.000 claims 1
- AJJNTDGBWHZORI-UHFFFAOYSA-N 8-methyl-4,4a,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC(=O)CC2CCC3=CC(C)=CC=C3N21 AJJNTDGBWHZORI-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 201000004240 prostatic hypertrophy Diseases 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000012047 saturated solution Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229960003473 androstanolone Drugs 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 210000002307 prostate Anatomy 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- MYAIDKISTKRVSQ-UHFFFAOYSA-N 1,2,4,4a,5,6-hexahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3CCC(=O)CC3CCC2=C1 MYAIDKISTKRVSQ-UHFFFAOYSA-N 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- SHALBPKEGDBVKK-UHFFFAOYSA-N 4-methoxybuta-1,3-dien-2-yloxy(trimethyl)silane Chemical compound COC=CC(=C)O[Si](C)(C)C SHALBPKEGDBVKK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229960003604 testosterone Drugs 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 1
- 108010029908 3-oxo-5-alpha-steroid 4-dehydrogenase Proteins 0.000 description 1
- 102000001779 3-oxo-5-alpha-steroid 4-dehydrogenase Human genes 0.000 description 1
- WCPYNROBHCBVBH-UHFFFAOYSA-N 4,8-dimethyl-4,4a,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC2=CC(C)=CC=C2N2C1C(C)C(=O)C=C2 WCPYNROBHCBVBH-UHFFFAOYSA-N 0.000 description 1
- AZJQJBOXQUMXGS-UHFFFAOYSA-N 4-methyl-1,2,4,4a,5,6-hexahydrobenzo[f]quinolizin-3-one Chemical compound C1CC2=CC=CC=C2N2C1C(C)C(=O)CC2 AZJQJBOXQUMXGS-UHFFFAOYSA-N 0.000 description 1
- FBWAJLPTZNQDAJ-UHFFFAOYSA-N 4-methyl-4,4a,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC2=CC=CC=C2N2C1C(C)C(=O)C=C2 FBWAJLPTZNQDAJ-UHFFFAOYSA-N 0.000 description 1
- POEIHRYHSHOMRL-UHFFFAOYSA-N 4-methyl-5,6-dihydrobenzo[f]quinolizin-3-one Chemical compound C1CC2=CC=CC=C2N2C1=C(C)C(=O)C=C2 POEIHRYHSHOMRL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VKAGNHCBASQZNC-UHFFFAOYSA-N 8-chloro-4-methyl-4,4a,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC2=CC(Cl)=CC=C2N2C1C(C)C(=O)C=C2 VKAGNHCBASQZNC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 101000958664 Homo sapiens Nucleus accumbens-associated protein 1 Proteins 0.000 description 1
- 101000631760 Homo sapiens Sodium channel protein type 1 subunit alpha Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 101100174763 Mus musculus Galk1 gene Proteins 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 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
- 102100028910 Sodium channel protein type 1 subunit alpha Human genes 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- JOAPBVRQZQYKMS-UHFFFAOYSA-N buta-1,3-dien-2-yloxy(trimethyl)silane Chemical compound C[Si](C)(C)OC(=C)C=C JOAPBVRQZQYKMS-UHFFFAOYSA-N 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- YAGCIXJCAUGCGI-UHFFFAOYSA-N butoxycarbonyl butyl carbonate Chemical compound CCCCOC(=O)OC(=O)OCCCC YAGCIXJCAUGCGI-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000008175 fetal development Effects 0.000 description 1
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 1
- 229960004039 finasteride Drugs 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000008011 inorganic excipient Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000000260 male genitalia Anatomy 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000008012 organic excipient Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 208000017497 prostate disease Diseases 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- XOVSRHHCHKUFKM-UHFFFAOYSA-N s-methylthiohydroxylamine Chemical compound CSN XOVSRHHCHKUFKM-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/28—Antiandrogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Pregnancy & Childbirth (AREA)
- Gynecology & Obstetrics (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT96FI000019A IT1286545B1 (it) | 1996-02-09 | 1996-02-09 | Derivati benzo(c) chinolizinici,loro preparazione ed uso come inibitori delle 5-alfa-riduttasi |
| PCT/EP1997/000552 WO1997029107A1 (en) | 1996-02-09 | 1997-02-07 | BENZO[C]QUINOLIZINE DERIVATIVES, THEIR PREPARATION AND USE AS 5α-REDUCTASES INHIBITORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO983444D0 NO983444D0 (no) | 1998-07-24 |
| NO983444L NO983444L (no) | 1998-07-24 |
| NO320155B1 true NO320155B1 (no) | 2005-11-07 |
Family
ID=11351478
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19983444A NO320155B1 (no) | 1996-02-09 | 1998-07-24 | Benzo(c)kinolizinderivater, deres fremstilling, farmasoytisk sammensetning som inneholder derivatene, og anvendelse av derivatene til a fremstille et legemiddel |
| NO20045132A NO20045132L (no) | 1996-02-09 | 2004-11-24 | Benzo(c)kinolizinderivater, deres fremstilling og anvendelse som 5alfa- reduktaseinhibitorer |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20045132A NO20045132L (no) | 1996-02-09 | 2004-11-24 | Benzo(c)kinolizinderivater, deres fremstilling og anvendelse som 5alfa- reduktaseinhibitorer |
Country Status (26)
| Country | Link |
|---|---|
| US (3) | US6303622B1 (da) |
| EP (1) | EP0880520B1 (da) |
| JP (1) | JP2000504680A (da) |
| KR (1) | KR100480448B1 (da) |
| CN (1) | CN1116296C (da) |
| AT (1) | ATE237614T1 (da) |
| AU (1) | AU711886C (da) |
| BG (1) | BG64596B1 (da) |
| CZ (1) | CZ298061B6 (da) |
| DE (1) | DE69720966T2 (da) |
| DK (1) | DK0880520T3 (da) |
| EA (1) | EA000975B1 (da) |
| EE (1) | EE04058B1 (da) |
| ES (1) | ES2192263T3 (da) |
| HK (1) | HK1018783A1 (da) |
| HU (1) | HUP9900509A3 (da) |
| IL (2) | IL125628A0 (da) |
| IT (1) | IT1286545B1 (da) |
| MX (1) | MX9806229A (da) |
| NO (2) | NO320155B1 (da) |
| NZ (1) | NZ331256A (da) |
| PL (1) | PL187618B1 (da) |
| PT (1) | PT880520E (da) |
| SK (1) | SK283299B6 (da) |
| UA (1) | UA67724C2 (da) |
| WO (1) | WO1997029107A1 (da) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITFI970193A1 (it) * | 1997-08-01 | 1999-02-01 | Applied Research Systems | Uso di derivati benzo(c) chinolizinici come regolatori della crescita delle piante e composizioni ad uso agricolo che contengono tali |
| EP0926148A1 (en) * | 1997-12-23 | 1999-06-30 | Applied Research Systems Ars Holding N.V. | Benzo (C)quinolizine derivatives, their preparation and use as 5-alphareductases inhibitors |
| TR200100286T2 (tr) | 1998-08-03 | 2001-07-23 | Applied Research Systems Ars Holding N.V. | (1H)-Benzo[C]kuinolizin-3-on türevlerinin sentezi için proses. |
| SI1928454T1 (sl) | 2005-05-10 | 2015-01-30 | Intermune, Inc. | Piridonski derivati za moduliranje s stresom aktiviranega protein kinaznega sistema |
| EA013525B1 (ru) * | 2005-05-20 | 2010-06-30 | Алантос-Фармасьютикалз Холдинг, Инк. | Гетеробициклические ингибиторы металлопротеазы и их применение |
| US20070155738A1 (en) | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| JP5627574B2 (ja) | 2008-06-03 | 2014-11-19 | インターミューン， インコーポレイテッド | 炎症性および線維性疾患を治療するための化合物および方法 |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| KR102373700B1 (ko) | 2014-04-02 | 2022-03-11 | 인터뮨, 인크. | 항섬유성 피리디논 |
| CN105001216B (zh) * | 2015-07-08 | 2017-03-01 | 中国科学院兰州化学物理研究所 | 一种喹嗪酮的制备方法 |
| CN107089980B (zh) * | 2017-05-11 | 2019-08-30 | 合肥工业大学 | 一种手性苯并[a]喹嗪-2-酮类化合物及其不对称催化合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1534278A (fr) * | 1966-08-15 | 1968-07-26 | Bristol Myers Co | Procédé de fabrication de 1, 4-dihydroquinoléine-n-carboxylates d'alcoyle |
| US3455929A (en) * | 1966-08-15 | 1969-07-15 | Bristol Myers Co | Esters of 1,4-dihydroquinoline-n-carboxylic acids and thione acids |
| US3625877A (en) * | 1968-01-08 | 1971-12-07 | Eastman Kodak Co | High-modulus polycarbonate compositions |
| SU1027166A1 (ru) * | 1981-09-11 | 1983-07-07 | Киевский Ордена Ленина Государственный Университет Им.Т.Г.Шевченко | Способ получени 1,2-полиметиленкетоцианоазагетероциклов |
| IE57014B1 (en) | 1983-03-25 | 1992-03-11 | Wyeth John & Brother Ltd | Benzoquinolizines |
-
1996
- 1996-02-09 IT IT96FI000019A patent/IT1286545B1/it active IP Right Grant
-
1997
- 1997-02-07 AT AT97903230T patent/ATE237614T1/de not_active IP Right Cessation
- 1997-02-07 HU HU9900509A patent/HUP9900509A3/hu unknown
- 1997-02-07 DK DK97903230T patent/DK0880520T3/da active
- 1997-02-07 PL PL97328123A patent/PL187618B1/pl not_active IP Right Cessation
- 1997-02-07 NZ NZ331256A patent/NZ331256A/xx unknown
- 1997-02-07 EP EP97903230A patent/EP0880520B1/en not_active Expired - Lifetime
- 1997-02-07 PT PT97903230T patent/PT880520E/pt unknown
- 1997-02-07 SK SK1044-98A patent/SK283299B6/sk not_active IP Right Cessation
- 1997-02-07 US US09/117,583 patent/US6303622B1/en not_active Expired - Fee Related
- 1997-02-07 EE EE9800233A patent/EE04058B1/xx not_active IP Right Cessation
- 1997-02-07 KR KR10-1998-0705848A patent/KR100480448B1/ko not_active IP Right Cessation
- 1997-02-07 IL IL12562897A patent/IL125628A0/xx active IP Right Grant
- 1997-02-07 EA EA199800701A patent/EA000975B1/ru unknown
- 1997-02-07 WO PCT/EP1997/000552 patent/WO1997029107A1/en active IP Right Grant
- 1997-02-07 DE DE69720966T patent/DE69720966T2/de not_active Expired - Fee Related
- 1997-02-07 JP JP9528158A patent/JP2000504680A/ja not_active Ceased
- 1997-02-07 CN CN97192097A patent/CN1116296C/zh not_active Expired - Fee Related
- 1997-02-07 CZ CZ0228998A patent/CZ298061B6/cs not_active IP Right Cessation
- 1997-02-07 AU AU17672/97A patent/AU711886C/en not_active Ceased
- 1997-02-07 ES ES97903230T patent/ES2192263T3/es not_active Expired - Lifetime
- 1997-07-02 UA UA98094739A patent/UA67724C2/uk unknown
-
1998
- 1998-07-24 NO NO19983444A patent/NO320155B1/no not_active IP Right Cessation
- 1998-07-30 BG BG102661A patent/BG64596B1/bg unknown
- 1998-08-03 IL IL125628A patent/IL125628A/en not_active IP Right Cessation
- 1998-08-03 MX MX9806229A patent/MX9806229A/es unknown
-
1999
- 1999-09-03 HK HK99103821A patent/HK1018783A1/xx not_active IP Right Cessation
-
2001
- 2001-06-25 US US09/891,088 patent/US6552034B2/en not_active Expired - Fee Related
- 2001-06-25 US US09/888,952 patent/US6555549B2/en not_active Expired - Fee Related
-
2004
- 2004-11-24 NO NO20045132A patent/NO20045132L/no not_active Application Discontinuation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO320155B1 (no) | Benzo(c)kinolizinderivater, deres fremstilling, farmasoytisk sammensetning som inneholder derivatene, og anvendelse av derivatene til a fremstille et legemiddel | |
| CA3230123A1 (en) | Spiro indoline inhibitors of kif18a | |
| CA2344694A1 (en) | Benzazine derivatives as phosphodiesterase 4 inhibitors | |
| NO169894B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive tetrahydronaftalen-forbindelser | |
| JP7182553B2 (ja) | Ｒｏｒガンマ調節剤としての三環スルホン類 | |
| CA2474850A1 (en) | Imidazo[1,2-a]pyridine derivatives | |
| CZ2001434A3 (cs) | Způsob výroby chinolizin-3-onových derivátů | |
| CA2156128A1 (en) | Substituted quinoline derivatives, a process for their preparation, and their use | |
| CN102584679B (zh) | 一类苯并咔唑酰胺类化合物、其制备方法和用途 | |
| Kavanagh et al. | Stereocontrolled preparation of bicyclic alkaloid analogues: an approach towards the kinabalurine skeleton | |
| EP1066284B1 (en) | Benzo(c)quinolizine derivatives and their use as 5 alpha-reductases inhibitors | |
| US6048869A (en) | Tricyclic compounds | |
| CA2245758C (en) | Benzo[c]quinolizine derivatives, their preparation and use as 5.alpha.-reductases inhibitors | |
| JP2002308876A (ja) | 抗菌活性を有する４−オキソキノリジン系化合物 | |
| NO801951L (no) | Fremgangsmaate ved fremstilling av nye isokinolinderivater | |
| MXPA00006219A (en) | Benzo[c]quinolizine derivatives and their use as 5 alpha-reductases inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CREP | Change of representative |
Representative=s name: ONSAGERS AS, POSTBOKS 6963 ST OLAVS PLASS, 0130 OS |
|
| MM1K | Lapsed by not paying the annual fees |