JP2008500992A5 - - Google Patents
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- Publication number
- JP2008500992A5 JP2008500992A5 JP2007513922A JP2007513922A JP2008500992A5 JP 2008500992 A5 JP2008500992 A5 JP 2008500992A5 JP 2007513922 A JP2007513922 A JP 2007513922A JP 2007513922 A JP2007513922 A JP 2007513922A JP 2008500992 A5 JP2008500992 A5 JP 2008500992A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- use according
- formula
- bromo
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 16
- 239000003814 drug Substances 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- -1 cyano, hydroxy Chemical group 0.000 claims 11
- 229940079593 drug Drugs 0.000 claims 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 8
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 241000186359 Mycobacterium Species 0.000 claims 6
- 125000004414 alkyl thio group Chemical group 0.000 claims 6
- 239000003926 antimycobacterial agent Substances 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 150000003248 quinolines Chemical class 0.000 claims 6
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000000815 N-oxide group Chemical group 0.000 claims 5
- 230000001355 anti-mycobacterial effect Effects 0.000 claims 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- QUIJNHUBAXPXFS-XLJNKUFUSA-N bedaquiline Chemical compound C1([C@H](C2=CC3=CC(Br)=CC=C3N=C2OC)[C@@](O)(CCN(C)C)C=2C3=CC=CC=C3C=CC=2)=CC=CC=C1 QUIJNHUBAXPXFS-XLJNKUFUSA-N 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- VPZIAIQZWHQVKN-UHFFFAOYSA-N 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-1,2-diphenylbutan-2-ol Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C(O)(CCN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VPZIAIQZWHQVKN-UHFFFAOYSA-N 0.000 claims 2
- TZNZMTAIOJDNJP-UHFFFAOYSA-N 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(3-fluorophenyl)-1-phenylbutan-2-ol Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C(O)(CCN(C)C)C=1C=C(F)C=CC=1)C1=CC=CC=C1 TZNZMTAIOJDNJP-UHFFFAOYSA-N 0.000 claims 2
- QUIJNHUBAXPXFS-UHFFFAOYSA-N 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C(O)(CCN(C)C)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 QUIJNHUBAXPXFS-UHFFFAOYSA-N 0.000 claims 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims 2
- 229930189077 Rifamycin Natural products 0.000 claims 2
- ZWBTYMGEBZUQTK-PVLSIAFMSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23-dioxospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(32),2,4,9,19,21,24,26,30-nonaene-28,4'-piperidine]-13-yl] acetate Chemical compound CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c4NC5(CCN(CC(C)C)CC5)N=c4c(=NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c(O)c2c(O)c3C ZWBTYMGEBZUQTK-PVLSIAFMSA-N 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 229960000885 rifabutin Drugs 0.000 claims 2
- 229960002599 rifapentine Drugs 0.000 claims 2
- WDZCUPBHRAEYDL-GZAUEHORSA-N rifapentine Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C(O)=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N(CC1)CCN1C1CCCC1 WDZCUPBHRAEYDL-GZAUEHORSA-N 0.000 claims 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- XDEHPNQRQKHQQC-UHFFFAOYSA-N 1-(6-bromo-2-methoxyquinolin-3-yl)-2-(2,3-difluorophenyl)-4-(dimethylamino)-1-phenylbutan-2-ol Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C(O)(CCN(C)C)C=1C(=C(F)C=CC=1)F)C1=CC=CC=C1 XDEHPNQRQKHQQC-UHFFFAOYSA-N 0.000 claims 1
- CLLPSOGUEAXIIW-UHFFFAOYSA-N 1-(6-bromo-2-methoxyquinolin-3-yl)-2-(2,5-difluorophenyl)-4-(dimethylamino)-1-phenylbutan-2-ol Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C(O)(CCN(C)C)C=1C(=CC=C(F)C=1)F)C1=CC=CC=C1 CLLPSOGUEAXIIW-UHFFFAOYSA-N 0.000 claims 1
- UAUNEMZTBIFYAG-UHFFFAOYSA-N 1-(6-bromo-2-methoxyquinolin-3-yl)-2-(3,5-difluorophenyl)-4-(dimethylamino)-1-phenylbutan-2-ol Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C(O)(CCN(C)C)C=1C=C(F)C=C(F)C=1)C1=CC=CC=C1 UAUNEMZTBIFYAG-UHFFFAOYSA-N 0.000 claims 1
- CFPPFXNAPDMERR-UHFFFAOYSA-N 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-1-(4-methylphenyl)-2-naphthalen-1-ylbutan-2-ol Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C(O)(CCN(C)C)C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C)C=C1 CFPPFXNAPDMERR-UHFFFAOYSA-N 0.000 claims 1
- HGUAWYGZOVFIAB-UHFFFAOYSA-N 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(2-fluorophenyl)-1-phenylbutan-2-ol Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C(O)(CCN(C)C)C=1C(=CC=CC=1)F)C1=CC=CC=C1 HGUAWYGZOVFIAB-UHFFFAOYSA-N 0.000 claims 1
- GOBOQBZOZDRXCQ-UHFFFAOYSA-N 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(methylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol Chemical compound C=1C=CC2=CC=CC=C2C=1C(O)(CCNC)C(C=1C(=NC2=CC=C(Br)C=C2C=1)OC)C1=CC=CC=C1 GOBOQBZOZDRXCQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 claims 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims 1
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 claims 1
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 claims 1
- DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 claims 1
- DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 229960004821 amikacin Drugs 0.000 claims 1
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 claims 1
- 229960004909 aminosalicylic acid Drugs 0.000 claims 1
- 229960003022 amoxicillin Drugs 0.000 claims 1
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims 1
- 229940034014 antimycobacterial agent Drugs 0.000 claims 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229960003405 ciprofloxacin Drugs 0.000 claims 1
- 229960002626 clarithromycin Drugs 0.000 claims 1
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 claims 1
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 claims 1
- 229960003324 clavulanic acid Drugs 0.000 claims 1
- WDQPAMHFFCXSNU-BGABXYSRSA-N clofazimine Chemical compound C12=CC=CC=C2N=C2C=C(NC=3C=CC(Cl)=CC=3)C(=N/C(C)C)/C=C2N1C1=CC=C(Cl)C=C1 WDQPAMHFFCXSNU-BGABXYSRSA-N 0.000 claims 1
- 229960004287 clofazimine Drugs 0.000 claims 1
- 229960003077 cycloserine Drugs 0.000 claims 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229960000285 ethambutol Drugs 0.000 claims 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229940124307 fluoroquinolone Drugs 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 229960003350 isoniazid Drugs 0.000 claims 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 239000003120 macrolide antibiotic agent Substances 0.000 claims 1
- 229940041033 macrolides Drugs 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 229960003702 moxifloxacin Drugs 0.000 claims 1
- FABPRXSRWADJSP-MEDUHNTESA-N moxifloxacin Chemical compound COC1=C(N2C[C@H]3NCCC[C@H]3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 FABPRXSRWADJSP-MEDUHNTESA-N 0.000 claims 1
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims 1
- 229960001699 ofloxacin Drugs 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 150000007660 quinolones Chemical class 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 229960001225 rifampicin Drugs 0.000 claims 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims 1
- 229960003292 rifamycin Drugs 0.000 claims 1
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical compound OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 claims 1
- BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 claims 1
- 229940081192 rifamycins Drugs 0.000 claims 1
- 229960004954 sparfloxacin Drugs 0.000 claims 1
- DZZWHBIBMUVIIW-DTORHVGOSA-N sparfloxacin Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F DZZWHBIBMUVIIW-DTORHVGOSA-N 0.000 claims 1
- 229960005322 streptomycin Drugs 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 claims 1
- 229960003231 thioacetazone Drugs 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04102402 | 2004-05-28 | ||
| EP04102402.7 | 2004-05-28 | ||
| PCT/EP2005/052371 WO2005117875A1 (en) | 2004-05-28 | 2005-05-24 | Use of substituted quinoline derivatives for the treatment of drug resistant mycobacterial diseases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012152373A Division JP5675718B2 (ja) | 2004-05-28 | 2012-07-06 | 薬剤耐性マイコバクテリア性疾患の処置のための置換キノリン誘導体の使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008500992A JP2008500992A (ja) | 2008-01-17 |
| JP2008500992A5 true JP2008500992A5 (OSRAM) | 2008-07-10 |
| JP5081617B2 JP5081617B2 (ja) | 2012-11-28 |
Family
ID=34929150
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007513922A Expired - Lifetime JP5081617B2 (ja) | 2004-05-28 | 2005-05-24 | 薬剤耐性マイコバクテリア性疾患の処置のための置換キノリン誘導体の使用 |
| JP2012152373A Expired - Lifetime JP5675718B2 (ja) | 2004-05-28 | 2012-07-06 | 薬剤耐性マイコバクテリア性疾患の処置のための置換キノリン誘導体の使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012152373A Expired - Lifetime JP5675718B2 (ja) | 2004-05-28 | 2012-07-06 | 薬剤耐性マイコバクテリア性疾患の処置のための置換キノリン誘導体の使用 |
Country Status (34)
| Country | Link |
|---|---|
| US (2) | US20070249667A1 (OSRAM) |
| EP (1) | EP1753427B1 (OSRAM) |
| JP (2) | JP5081617B2 (OSRAM) |
| KR (2) | KR20130024969A (OSRAM) |
| CN (2) | CN1976704B (OSRAM) |
| AP (1) | AP2037A (OSRAM) |
| AR (1) | AR049127A1 (OSRAM) |
| AT (1) | ATE390925T1 (OSRAM) |
| AU (1) | AU2005249231B2 (OSRAM) |
| BR (1) | BRPI0510414B1 (OSRAM) |
| CA (1) | CA2566544C (OSRAM) |
| CL (1) | CL2009001980A1 (OSRAM) |
| CY (1) | CY1110388T1 (OSRAM) |
| DE (1) | DE602005005810T2 (OSRAM) |
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| EA (1) | EA010651B1 (OSRAM) |
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| HR (1) | HRP20080307T3 (OSRAM) |
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| MX (1) | MXPA06013888A (OSRAM) |
| MY (1) | MY140611A (OSRAM) |
| NO (1) | NO338624B1 (OSRAM) |
| NZ (1) | NZ550840A (OSRAM) |
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| PT (1) | PT1753427E (OSRAM) |
| RS (1) | RS50585B (OSRAM) |
| SI (1) | SI1753427T1 (OSRAM) |
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| WO (1) | WO2005117875A1 (OSRAM) |
| ZA (1) | ZA200609899B (OSRAM) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1753427B1 (en) * | 2004-05-28 | 2008-04-02 | Janssen Pharmaceutica N.V. | Use of substituted quinoline derivatives for the treatment of drug resistant mycobacterial diseases |
| JP2006182755A (ja) * | 2004-12-24 | 2006-07-13 | Janssen Pharmaceut Nv | 潜伏性結核の処置 |
| EE05697B1 (et) * | 2005-06-08 | 2014-02-17 | Janssen Pharmaceutica N.V. | Kinoliini derivaadid kui antibakteriaalsed toimeained |
| JP5349730B2 (ja) * | 2005-06-09 | 2013-11-20 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 抗バクテリア剤としてのキノリン誘導体 |
| JO3270B1 (ar) * | 2005-06-28 | 2018-09-16 | Janssen Pharmaceutica Nv | مشتقات كوينولين بصفة عوامل مضادة للبكتيريا |
| JO2752B1 (en) * | 2005-06-28 | 2014-03-15 | شركة جانسين فارماسوتيكا ان. في | Quinoline derivatives acting as antibacterial agents |
| DK1898909T3 (en) * | 2005-06-28 | 2017-02-06 | Janssen Pharmaceutica Nv | QUINOLIN DERIVATIVES AS ANTIBACTERIAL AGENTS |
| US8686002B2 (en) | 2005-08-21 | 2014-04-01 | AbbVie Deutschland GmbH & Co. KG | Heterocyclic compounds and their use as binding partners for 5-HT5 receptors |
| UA97813C2 (uk) * | 2006-12-05 | 2012-03-26 | Янссен Фармацевтика Н.В. | Фумаратна сіль (альфа s, бета r)-6-бром-альфа-[2-(диметиламіно)етил]-2-метоксі-альфа-1-нафталеніл-бета-феніл-3-хінолінетанолу |
| JO2683B1 (en) * | 2006-12-06 | 2013-03-03 | جانسين فارماسوتيكا ان. في | Quinoline antibacterial derivatives |
| JO2685B1 (en) * | 2006-12-06 | 2013-03-03 | جانسين فارماسوتيكا ان في | Quinoline antibacterial derivatives |
| JO2725B1 (en) * | 2006-12-06 | 2013-09-15 | جانسين فارماسوتيكا ان. في | Quinoline antibacterial derivatives |
| JO2970B1 (en) | 2006-12-06 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Quinoline antibacterial derivatives |
| JO3271B1 (ar) * | 2006-12-06 | 2018-09-16 | Janssen Pharmaceutica Nv | مشتقات الكوينولين المضادة للجراثيم |
| JO2684B1 (en) * | 2006-12-06 | 2013-03-03 | جانسين فارماسوتيكا ان في | Quinoline antibacterial derivatives |
| MD4009C2 (ro) * | 2008-07-15 | 2010-08-31 | Институт Химии Академии Наук Молдовы | Utilizarea 1-metil-4-(N-metilaminobutil-4)-β-carbolinei în calitate de remediu antituberculos |
| RU2404971C2 (ru) * | 2008-12-02 | 2010-11-27 | ЗАО "Фарм-Синтез" | Новые производные хинолина, способ их получения, их применение для лечения микобактериальных инфекций, фармацевтическая композиция на их основе |
| JP2013504591A (ja) * | 2009-09-11 | 2013-02-07 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｎ−ベンジル−３−（４−クロロフェニル）−２−［メチル−［２−オキソ−２−（３，４，５−トリメトキシフェニル）アセチル］アミノ］−ｎ−［３−（４−ピリジル）−１−［２−（４−ピリジル）エチル］プロピル］プロパンアミドの組成物およびその使用 |
| CN102249935B (zh) | 2010-05-17 | 2015-05-20 | 中国人民解放军军事医学科学院毒物药物研究所 | 芳香2-丁醇类化合物及其医药用途 |
| CN104254527B (zh) | 2012-04-27 | 2017-05-31 | 詹森药业有限公司 | 抗菌的喹啉衍生物 |
| AU2013254670B2 (en) | 2012-04-27 | 2017-03-30 | Janssen Pharmaceutica Nv | Antibacterial quinoline derivatives |
| WO2016008381A1 (zh) * | 2014-07-14 | 2016-01-21 | 辰欣药业股份有限公司 | 吡啶衍生物及其作为抗分支杆菌的应用 |
| CN105330595B (zh) * | 2014-07-14 | 2019-12-10 | 上海嘉坦医药科技有限公司 | 吡啶衍生物及其作为抗分支杆菌的应用 |
| FI3250182T3 (fi) | 2015-01-27 | 2023-06-28 | Janssen Pharmaceutica Nv | Dispergoituvia koostumuksia |
| CN106279017A (zh) * | 2015-05-21 | 2017-01-04 | 重庆圣华曦药业股份有限公司 | 贝达喹啉晶型、组合物及其制备方法 |
| RU2018111482A (ru) * | 2015-10-20 | 2019-11-21 | Чжэцзян Хисунь Фармасьютикал Ко., Лтд. | Кристаллические формы бедаквилин фумарата и способы их получения |
| WO2017121323A1 (zh) * | 2016-01-13 | 2017-07-20 | 辰欣药业股份有限公司 | 一种吡啶衍生物类化合物的制备方法及其中间体和晶型 |
| CA3016068C (en) * | 2016-03-07 | 2024-02-27 | The Global Alliance For Tb Drug Development, Inc. | Antibacterial compounds and uses thereof |
| CN107243008B (zh) * | 2017-04-13 | 2021-03-30 | 中国科学院广州生物医药与健康研究院 | 吡唑并[1,5-a]吡啶类化合物的新应用及一种治疗脓肿分枝杆菌感染的组合物 |
| JP7184260B2 (ja) * | 2017-09-01 | 2022-12-06 | 学校法人北里研究所 | マイコバクテリウム・アビウム複合感染症に対する治療活性を有する新規化合物及びその製造方法 |
| WO2020047596A1 (en) * | 2018-09-04 | 2020-03-12 | Monash University | Antibacterial compounds and methods of use |
| WO2020144197A1 (en) | 2019-01-09 | 2020-07-16 | Janssen Pharmaceutica Nv | Combination in the treatment of nontuberculous mycobacterial diseases |
| US20230348436A1 (en) * | 2019-11-26 | 2023-11-02 | Nanyang Technological University | Compounds for treating tuberculosis |
| CN110804016B (zh) * | 2019-12-05 | 2022-11-04 | 福建省微生物研究所 | 抗结核分枝杆菌的二芳基喹啉衍生物 |
| KR20230107275A (ko) | 2020-11-12 | 2023-07-14 | 얀센 파마슈티카 엔.브이. | 비결핵성 마이코박테리아 질환의 치료에서 베다퀼린, 에탐부톨 및 마크롤라이드의 조합물 |
| WO2023217279A1 (zh) * | 2022-05-13 | 2023-11-16 | 广州嘉越医药科技有限公司 | 一种吡啶衍生物、中间体、制备方法和应用 |
| WO2023227123A1 (zh) * | 2022-05-27 | 2023-11-30 | 广州嘉越医药科技有限公司 | 吡啶衍生物的用途 |
| WO2023232838A1 (en) | 2022-05-31 | 2023-12-07 | Janssen Pharmaceutica Nv | Bedaquiline for use in the treatment of leprosy |
| CN120225518A (zh) * | 2022-11-15 | 2025-06-27 | 伊莱利利公司 | Ahr激动剂 |
| WO2025068448A1 (en) | 2023-09-28 | 2025-04-03 | Janssen Pharmaceutica Nv | Atp synthase inhibitors for use in the treatment of non-tuberculosis mycobacteria |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5399558A (en) * | 1993-11-24 | 1995-03-21 | Pathogenesis Corporation | Isoflavonoid antibacterial compounds, compositions and use |
| WO1998018326A1 (en) * | 1996-10-28 | 1998-05-07 | Department Of The Army, U.S. Government | Compounds, compositions and methods for treating antibiotic-resistant infections |
| US6103905A (en) * | 1997-06-19 | 2000-08-15 | Sepracor, Inc. | Quinoline-indole antimicrobial agents, uses and compositions related thereto |
| DK2301544T3 (da) * | 2002-07-25 | 2013-01-02 | Janssen Pharmaceutica Nv | Quinolinderivater som mellemprodukter til mykobakterielle inhibitorer |
| EP1753427B1 (en) * | 2004-05-28 | 2008-04-02 | Janssen Pharmaceutica N.V. | Use of substituted quinoline derivatives for the treatment of drug resistant mycobacterial diseases |
| EE05697B1 (et) * | 2005-06-08 | 2014-02-17 | Janssen Pharmaceutica N.V. | Kinoliini derivaadid kui antibakteriaalsed toimeained |
-
2005
- 2005-05-24 EP EP05743054A patent/EP1753427B1/en not_active Expired - Lifetime
- 2005-05-24 KR KR1020137002606A patent/KR20130024969A/ko not_active Ceased
- 2005-05-24 EA EA200602260A patent/EA010651B1/ru active Protection Beyond IP Right Term
- 2005-05-24 US US11/569,681 patent/US20070249667A1/en not_active Abandoned
- 2005-05-24 BR BRPI0510414-9A patent/BRPI0510414B1/pt not_active IP Right Cessation
- 2005-05-24 HR HR20080307T patent/HRP20080307T3/xx unknown
- 2005-05-24 PL PL05743054T patent/PL1753427T3/pl unknown
- 2005-05-24 PT PT05743054T patent/PT1753427E/pt unknown
- 2005-05-24 UA UAA200611048A patent/UA90267C2/ru unknown
- 2005-05-24 RS RSP-2008/0291A patent/RS50585B/sr unknown
- 2005-05-24 MX MXPA06013888A patent/MXPA06013888A/es active IP Right Grant
- 2005-05-24 NZ NZ550840A patent/NZ550840A/en not_active IP Right Cessation
- 2005-05-24 AT AT05743054T patent/ATE390925T1/de active
- 2005-05-24 JP JP2007513922A patent/JP5081617B2/ja not_active Expired - Lifetime
- 2005-05-24 ME MEP-2008-89A patent/ME01105B/me unknown
- 2005-05-24 SI SI200530294T patent/SI1753427T1/sl unknown
- 2005-05-24 WO PCT/EP2005/052371 patent/WO2005117875A1/en not_active Ceased
- 2005-05-24 DE DE602005005810T patent/DE602005005810T2/de not_active Expired - Lifetime
- 2005-05-24 DK DK05743054T patent/DK1753427T3/da active
- 2005-05-24 CA CA2566544A patent/CA2566544C/en not_active Expired - Lifetime
- 2005-05-24 KR KR1020067024974A patent/KR101371653B1/ko not_active Expired - Lifetime
- 2005-05-24 CN CN2005800170162A patent/CN1976704B/zh not_active Expired - Fee Related
- 2005-05-24 ES ES05743054T patent/ES2306146T3/es not_active Expired - Lifetime
- 2005-05-24 AU AU2005249231A patent/AU2005249231B2/en not_active Expired
- 2005-05-24 AP AP2006003828A patent/AP2037A/xx active
- 2005-05-24 CN CN2012103943126A patent/CN102908347A/zh active Pending
- 2005-05-24 JO JO200574A patent/JO2524B1/en active
- 2005-05-27 PA PA20058635201A patent/PA8635201A1/es unknown
- 2005-05-27 MY MYPI20052432A patent/MY140611A/en unknown
- 2005-05-27 AR ARP050102200A patent/AR049127A1/es unknown
- 2005-05-27 TW TW094117334A patent/TWI363625B/zh not_active IP Right Cessation
-
2006
- 2006-11-27 ZA ZA200609899A patent/ZA200609899B/xx unknown
- 2006-11-27 IL IL179630A patent/IL179630A/en active IP Right Grant
- 2006-12-28 NO NO20066041A patent/NO338624B1/no unknown
-
2008
- 2008-07-02 CY CY20081100696T patent/CY1110388T1/el unknown
-
2009
- 2009-10-20 CL CL2009001980A patent/CL2009001980A1/es unknown
-
2010
- 2010-03-08 US US12/719,221 patent/US20100168133A1/en not_active Abandoned
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2012
- 2012-07-06 JP JP2012152373A patent/JP5675718B2/ja not_active Expired - Lifetime
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