BG64596B1 - Бензо[с]хинолизинови производни, тяхното получаване и използване като инхибитори на 5 алфа-редуктази - Google Patents

Бензо[с]хинолизинови производни, тяхното получаване и използване като инхибитори на 5 алфа-редуктази Download PDF

Info

Publication number: BG64596B1
Authority: BG; Bulgaria
Prior art keywords: alkyl; benzo; group; phenyl; quinolizin
Prior art date: 1996-02-09

Application number

BG102661A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG102661A (en

Inventor

Antonio Guarna

Mario Serio

Original Assignee

Applied Research Systems Ars Holding N.V.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-02-09

Filing date

1998-07-30

Publication date

2005-08-31

1998-07-30 Application filed by Applied Research Systems Ars Holding N.V. filed Critical Applied Research Systems Ars Holding N.V.

1999-04-30 Publication of BG102661A publication Critical patent/BG102661A/xx

2005-08-31 Publication of BG64596B1 publication Critical patent/BG64596B1/bg

Links

238000002360 preparation method Methods 0.000 title claims abstract description 11
125000005605 benzo group Chemical group 0.000 title abstract 2
239000002677 5-alpha reductase inhibitor Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 53
238000000034 method Methods 0.000 claims abstract description 7
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 7
150000002148 esters Chemical class 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 58
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 47
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 34
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
229920006395 saturated elastomer Polymers 0.000 claims description 23
125000001624 naphthyl group Chemical group 0.000 claims description 22
BEWYHVAWEKZDPP-UHFFFAOYSA-N camphane Natural products C1CC2(C)CCC1C2(C)C BEWYHVAWEKZDPP-UHFFFAOYSA-N 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 20
-1 phenylamino, naphthylamino Chemical group 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 18
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 17
125000003342 alkenyl group Chemical group 0.000 claims description 17
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 16
125000000304 alkynyl group Chemical group 0.000 claims description 16
125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 16
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 15
WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 15
239000004914 cyclooctane Substances 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 14
108010044467 Isoenzymes Proteins 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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 claims description 4
UOGFZJRMCBHRQU-UHFFFAOYSA-N 10ah-benzo[c]quinolizine Chemical class N12C=CC=CC2=CC=C2C1C=CC=C2 UOGFZJRMCBHRQU-UHFFFAOYSA-N 0.000 claims description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
125000003368 amide group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 4
125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
210000002307 prostate Anatomy 0.000 claims description 4
125000006239 protecting group Chemical group 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
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 description 3
150000001540 azides Chemical class 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
229910052731 fluorine Inorganic materials 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 claims description 3
230000009466 transformation Effects 0.000 claims description 3
DTNKWSQCGOMAKM-UHFFFAOYSA-N 1,2,4,4a-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3CCC(=O)CC3C=CC2=C1 DTNKWSQCGOMAKM-UHFFFAOYSA-N 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 description 2
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 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
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 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
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 description 2
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 description 2
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 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
201000004384 Alopecia Diseases 0.000 claims description 2
206010060862 Prostate cancer Diseases 0.000 claims description 2
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
206010000496 acne Diseases 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
230000006315 carbonylation Effects 0.000 claims description 2
238000005810 carbonylation reaction Methods 0.000 claims description 2
230000003676 hair loss Effects 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
235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
239000012279 sodium borohydride Substances 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
XETQTCAMTVHYPO-UHFFFAOYSA-N Isocamphan von ungewisser Konfiguration Natural products C1CC2C(C)(C)C(C)C1C2 XETQTCAMTVHYPO-UHFFFAOYSA-N 0.000 claims 5
229930006742 bornane Natural products 0.000 claims 5
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 3
239000000546 pharmaceutical excipient Substances 0.000 claims 2
NKHRICCAJWEYLV-UHFFFAOYSA-N 1-methyl-1,2,4,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3C(C)CC(=O)CC3=CCC2=C1 NKHRICCAJWEYLV-UHFFFAOYSA-N 0.000 claims 1
CSKZKSFYFDVLFS-UHFFFAOYSA-N 1-phenyl-4,4a-dihydrobenzo[f]quinolizin-3-one Chemical compound C=1C(=O)CC2C=CC3=CC=CC=C3N2C=1C1=CC=CC=C1 CSKZKSFYFDVLFS-UHFFFAOYSA-N 0.000 claims 1
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 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 claims 1
206010020880 Hypertrophy Diseases 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
239000000047 product Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 6
125000000753 cycloalkyl group Chemical group 0.000 description 6
230000007170 pathology Effects 0.000 description 6
239000002904 solvent Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
239000013078 crystal Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-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
229960003473 androstanolone Drugs 0.000 description 3
239000008346 aqueous phase Substances 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
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239000011541 reaction mixture Substances 0.000 description 3
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ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
0 CC*(CC*)(*CC1)C(C(*)C2*)C1NC2=O Chemical compound CC*(CC*)(*CC1)C(C(*)C2*)C1NC2=O 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
208000004403 Prostatic Hyperplasia Diseases 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
SHALBPKEGDBVKK-VOTSOKGWSA-N danishefsky's diene Chemical compound CO\C=C\C(=C)O[Si](C)(C)C SHALBPKEGDBVKK-VOTSOKGWSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
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125000001424 substituent group Chemical group 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
210000001519 tissue Anatomy 0.000 description 2
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 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
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
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
244000304337 Cuminum cyminum Species 0.000 description 1
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229960000583 acetic acid Drugs 0.000 description 1
WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
125000006193 alkinyl group Chemical group 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
230000036621 balding Effects 0.000 description 1
NQRJJOIOVAOHLP-UHFFFAOYSA-N benzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3C=CC(=O)C=C3C=CC2=C1 NQRJJOIOVAOHLP-UHFFFAOYSA-N 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
125000004369 butenyl group Chemical group C(=CCC)* 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
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000013020 embryo development Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000011067 equilibration Methods 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
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
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
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
238000004519 manufacturing process Methods 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000001333 moisturizer Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
UMRZSTCPUPJPOJ-UHFFFAOYSA-N norbornane Chemical compound C1CC2CCC1C2 UMRZSTCPUPJPOJ-UHFFFAOYSA-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
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
230000003389 potentiating effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 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
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
150000003431 steroids Chemical class 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
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
238000011200 topical administration Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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 Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Reproductive Health (AREA)
Dermatology (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Gynecology & Obstetrics (AREA)
Pregnancy & Childbirth (AREA)
Urology & Nephrology (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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Plural Heterocyclic Compounds (AREA)

BG102661A 1996-02-09 1998-07-30 Бензо[с]хинолизинови производни, тяхното получаване и използване като инхибитори на 5 алфа-редуктази BG64596B1 (bg)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number	Publication Date
BG102661A BG102661A (en)	1999-04-30
BG64596B1 true BG64596B1 (bg)	2005-08-31

Family

ID=11351478

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG102661A BG64596B1 (bg)	1996-02-09	1998-07-30	Бензо[с]хинолизинови производни, тяхното получаване и използване като инхибитори на 5 алфа-редуктази

Country Status (25)

Country	Link
US (3)	US6303622B1 (pl)
EP (1)	EP0880520B1 (pl)
JP (1)	JP2000504680A (pl)
KR (1)	KR100480448B1 (pl)
CN (1)	CN1116296C (pl)
AT (1)	ATE237614T1 (pl)
AU (1)	AU711886C (pl)
BG (1)	BG64596B1 (pl)
CZ (1)	CZ298061B6 (pl)
DE (1)	DE69720966T2 (pl)
DK (1)	DK0880520T3 (pl)
EA (1)	EA000975B1 (pl)
EE (1)	EE04058B1 (pl)
ES (1)	ES2192263T3 (pl)
HU (1)	HUP9900509A3 (pl)
IL (2)	IL125628A0 (pl)
IT (1)	IT1286545B1 (pl)
MX (1)	MX9806229A (pl)
NO (2)	NO320155B1 (pl)
NZ (1)	NZ331256A (pl)
PL (1)	PL187618B1 (pl)
PT (1)	PT880520E (pl)
SK (1)	SK283299B6 (pl)
UA (1)	UA67724C2 (pl)
WO (1)	WO1997029107A1 (pl)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
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
US6723850B1 (en) *	1998-08-03	2004-04-20	Applied Research Systems Ars Holding N.V.	Process for the synthesis of (1-H)-benzo[c]quinolizin-3-ones derivatives
AP2007004244A0 (en)	2005-05-10	2007-12-31	Intermune Inc	Method of modulating stress-activated protein kinase system
JP5463034B2 (ja) *	2005-05-20	2014-04-09	アラントス・フアーマシユーテイカルズ・ホールデイング・インコーポレイテツド	ピリミジン若しくはトリアジン縮合二環式メタロプロテアーゼ阻害薬
US20070155738A1 (en)	2005-05-20	2007-07-05	Alantos Pharmaceuticals, Inc.	Heterobicyclic metalloprotease inhibitors
EP2296653B1 (en)	2008-06-03	2016-01-27	Intermune, Inc.	Compounds and methods for treating inflammatory and fibrotic disorders
AR092742A1 (es)	2012-10-02	2015-04-29	Intermune Inc	Piridinonas antifibroticas
RU2692485C2 (ru)	2014-04-02	2019-06-25	Интермьюн, Инк.	Противофиброзные пиридиноны
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

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3455929A (en) *	1966-08-15	1969-07-15	Bristol Myers Co	Esters of 1,4-dihydroquinoline-n-carboxylic acids and thione acids
FR1534278A (fr) *	1966-08-15	1968-07-26	Bristol Myers Co	Procédé de fabrication de 1, 4-dihydroquinoléine-n-carboxylates d'alcoyle
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 EE EE9800233A patent/EE04058B1/xx not_active IP Right Cessation
- 1997-02-07 DE DE69720966T patent/DE69720966T2/de not_active Expired - Fee Related
- 1997-02-07 WO PCT/EP1997/000552 patent/WO1997029107A1/en not_active Ceased
- 1997-02-07 PL PL97328123A patent/PL187618B1/pl not_active IP Right Cessation
- 1997-02-07 SK SK1044-98A patent/SK283299B6/sk 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 EA EA199800701A patent/EA000975B1/ru unknown
- 1997-02-07 HU HU9900509A patent/HUP9900509A3/hu unknown
- 1997-02-07 KR KR10-1998-0705848A patent/KR100480448B1/ko not_active Expired - Fee Related
- 1997-02-07 CZ CZ0228998A patent/CZ298061B6/cs not_active IP Right Cessation
- 1997-02-07 US US09/117,583 patent/US6303622B1/en not_active Expired - Fee Related
- 1997-02-07 IL IL12562897A patent/IL125628A0/xx active IP Right Grant
- 1997-02-07 PT PT97903230T patent/PT880520E/pt unknown
- 1997-02-07 DK DK97903230T patent/DK0880520T3/da active
- 1997-02-07 AT AT97903230T patent/ATE237614T1/de not_active IP Right Cessation
- 1997-02-07 AU AU17672/97A patent/AU711886C/en not_active Ceased
- 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 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
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

Publication number	Publication date
CN1116296C (zh)	2003-07-30
US6303622B1 (en)	2001-10-16
EE04058B1 (et)	2003-06-16
EP0880520A1 (en)	1998-12-02
AU711886C (en)	2002-10-17
CZ298061B6 (cs)	2007-06-06
US20010047098A1 (en)	2001-11-29
CZ228998A3 (cs)	1998-10-14
HUP9900509A2 (hu)	1999-06-28
PL187618B1 (pl)	2004-08-31
EE9800233A (et)	1998-12-15
ES2192263T3 (es)	2003-10-01
NO983444D0 (no)	1998-07-24
SK283299B6 (sk)	2003-05-02
EA000975B1 (ru)	2000-08-28
JP2000504680A (ja)	2000-04-18
ITFI960019A0 (pl)	1996-02-09
ITFI960019A1 (it)	1997-08-09
KR19990082126A (ko)	1999-11-15
KR100480448B1 (ko)	2005-08-31
DE69720966T2 (de)	2004-05-19
IT1286545B1 (it)	1998-07-15
EP0880520B1 (en)	2003-04-16
UA67724C2 (en)	2004-07-15
US6555549B2 (en)	2003-04-29
MX9806229A (es)	1998-11-30
EA199800701A1 (ru)	1999-02-25
BG102661A (en)	1999-04-30
US6552034B2 (en)	2003-04-22
NO320155B1 (no)	2005-11-07
WO1997029107A1 (en)	1997-08-14
NO20045132L (no)	1998-07-24
HK1018783A1 (en)	2000-01-07
US20010044542A1 (en)	2001-11-22
NO983444L (no)	1998-07-24
PT880520E (pt)	2003-07-31
DK0880520T3 (da)	2003-08-11
IL125628A0 (en)	1999-04-11
AU1767297A (en)	1997-08-28
ATE237614T1 (de)	2003-05-15
HUP9900509A3 (en)	1999-11-29
PL328123A1 (en)	1999-01-18
SK104498A3 (en)	1998-12-02
DE69720966D1 (de)	2003-05-22
CN1210536A (zh)	1999-03-10
NZ331256A (en)	1999-06-29
AU711886B2 (en)	1999-10-21
IL125628A (en)	2006-10-31

Publication	Publication Date	Title
EP0995743B1 (fr)	2003-04-02	Dérivés de dihydro- et tétrahydroquinoléine en tant qu'antioxydant médical
EA002146B1 (ru)	2001-12-24	Производные амида гетероарил-гексановой кислоты, их получение и их применение в качестве селективных ингибиторов связывания mip-1-альфа с его рецептором ccr1
CH644607A5 (fr)	1984-08-15	Octahydro-pyrazolo(3,4-g)quinoleines.
EP0266576A2 (en)	1988-05-11	1-Tert-alkyl-substituted naphthyridine and quinoline carboxylic acids as antibacterial agents
EP0880520B1 (en)	2003-04-16	Benzo [c]quinolizine derivatives, their preparation and use as 5-alpha-reductases inhibitors
KR19990064356A (ko)	1999-07-26	류코트리엔 생합성 억제제로서의 대칭성 비스-헤테로아릴메톡시페닐알킬 카복실레이트
Kunitomo et al.	1983	Structure and synthesis of menisporphine, a new type of isoquinoline alkaloid: Alkaloids of menispermum dauricum DC.(9)
CZ2001434A3 (cs)	2001-08-15	Způsob výroby chinolizin-3-onových derivátů
JPH10512899A (ja)	1998-12-08	Ｎ−アセチルアルデエミンの類似体、それらの調製及び使用方法
JP2005530691A (ja)	2005-10-13	新規なチロインジシンとその関連プロセス、薬学的組成物および方法
EP1066284B1 (en)	2005-08-31	Benzo(c)quinolizine derivatives and their use as 5 alpha-reductases inhibitors
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