JP2006504658A5 - - Google Patents
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- JP2006504658A5 JP2006504658A5 JP2004523812A JP2004523812A JP2006504658A5 JP 2006504658 A5 JP2006504658 A5 JP 2006504658A5 JP 2004523812 A JP2004523812 A JP 2004523812A JP 2004523812 A JP2004523812 A JP 2004523812A JP 2006504658 A5 JP2006504658 A5 JP 2006504658A5
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- JP
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- Prior art keywords
- compound
- alkyl
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- hydrogen
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- 150000001875 compounds Chemical class 0.000 claims 64
- 229910052739 hydrogen Inorganic materials 0.000 claims 25
- 239000001257 hydrogen Substances 0.000 claims 25
- 125000000217 alkyl group Chemical group 0.000 claims 24
- 125000005843 halogen group Chemical group 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 16
- -1 cyano, hydroxy Chemical group 0.000 claims 15
- 125000004432 carbon atom Chemical group C* 0.000 claims 14
- 239000002253 acid Substances 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 10
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 10
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 238000003556 assay Methods 0.000 claims 7
- 125000001188 haloalkyl group Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000001624 naphthyl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 125000000815 N-oxide group Chemical group 0.000 claims 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 201000008827 tuberculosis Diseases 0.000 claims 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 125000004568 thiomorpholinyl 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
- 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 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
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 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 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
- 125000005605 benzo group Chemical group 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
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- OPCWVBOOZWPXPM-UHFFFAOYSA-N CN(C)CCC(C(C(C1)C(OC)=NC(C=C2)=C1CC2Br)c1ccccc1)(c1c(cccc2)c2ccc1)O Chemical compound CN(C)CCC(C(C(C1)C(OC)=NC(C=C2)=C1CC2Br)c1ccccc1)(c1c(cccc2)c2ccc1)O OPCWVBOOZWPXPM-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39871102P | 2002-07-25 | 2002-07-25 | |
| PCT/EP2003/050322 WO2004011436A1 (en) | 2002-07-25 | 2003-07-18 | Quinoline derivatives and their use as mycobacterial inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006504658A JP2006504658A (ja) | 2006-02-09 |
| JP2006504658A5 true JP2006504658A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2006-04-27 |
| JP4484703B2 JP4484703B2 (ja) | 2010-06-16 |
Family
ID=31188461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004523812A Expired - Lifetime JP4484703B2 (ja) | 2002-07-25 | 2003-07-18 | キノリン誘導体およびミコバクテリア抑制剤としてのそれらの使用 |
Country Status (37)
Families Citing this family (96)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ547277A (en) * | 2004-01-23 | 2009-08-28 | Janssen Pharmaceutica Nv | Substituted quinolines and their use as mycobacterial inhibitors |
| UA86952C2 (uk) * | 2004-01-23 | 2009-06-10 | Янссен Фармацевтика Н.В. | Похідні хіноліну та їх застосування як мікобактеріальних інгібіторів |
| MXPA06008596A (es) * | 2004-01-29 | 2006-08-28 | Janssen Pharmaceutica Nv | Derivados de quinolina para uso como inhibidores micobacterianos. |
| ES2306146T3 (es) * | 2004-05-28 | 2008-11-01 | Janssen Pharmaceutica Nv | Uso de derivados de quinolina sustituidos para el tratamiento de enfermedades micobacterianas resistentes a farmacos. |
| ME02935B (me) | 2004-09-28 | 2018-04-20 | Janssen Pharmaceutica Nv | Vezujući domen bakterijske atp sintaze |
| EE05394B1 (et) * | 2004-12-24 | 2011-04-15 | Janssen Pharmaceutica N.V. | Kinoliinihendid kasutamiseks latentse tuberkuloosi ravis |
| EA009779B1 (ru) * | 2004-12-24 | 2008-04-28 | Янссен Фармацевтика Н.В. | Лечение латентного туберкулёза |
| ME01445B (me) * | 2005-05-25 | 2013-12-20 | Janssen Pharmaceutica Nv | PROCES ZA PRIPREMU (ALFA S, BETA R)-6-BROMO-ALFA-[2-(DIMETILAMINO)ETIL]-2-METOKSI-ALF A-l-NAFTALENIL-BETA-FENIL-3-KINOLINETANOLA |
| CA2528849C (en) | 2005-06-08 | 2014-01-14 | Janssen Pharmaceutica N.V. | Quinoline derivatives as antibacterial agents |
| TWI380819B (zh) * | 2005-06-08 | 2013-01-01 | Janssen Pharmaceutica Nv | 用作抗細菌劑之喹啉衍生物 |
| KR101318181B1 (ko) * | 2005-06-09 | 2013-10-16 | 얀센 파마슈티카 엔.브이. | 항균제로서의 퀴놀린 유도체 |
| 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 |
| EA010601B1 (ru) * | 2005-06-09 | 2008-10-30 | Янссен Фармацевтика Н.В. | Производные хинолина в качестве антибактериальных агентов |
| 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 |
| BRPI0613999B8 (pt) * | 2005-06-28 | 2021-05-25 | Janssen Pharmaceutica Nv | uso de um composto derivado de quinolina, o referido composto, sua combinação, composição farmacêutica, uso da referida combinação, e produto |
| JO3077B1 (ar) | 2005-07-28 | 2017-03-15 | Janssen Pharmaceutica Nv | مشتقات كوينولين مضادة للبكتيريا |
| JO2837B1 (en) * | 2005-08-03 | 2014-09-15 | جانسن فارمسيتكا ان في | Quinoline derivatives acting as antibacterial agents |
| JO2952B1 (en) | 2005-08-03 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Quinoline derivatives acting as antibacterial agents |
| JO2855B1 (en) | 2005-08-03 | 2015-03-15 | شركة جانسين فارماسوتيكا ان. في | Quinoline derivatives acting 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 |
| DE102005044817A1 (de) | 2005-09-20 | 2007-03-22 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| 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 |
| JO2684B1 (en) * | 2006-12-06 | 2013-03-03 | جانسين فارماسوتيكا ان في | Quinoline antibacterial derivatives |
| JO3271B1 (ar) * | 2006-12-06 | 2018-09-16 | Janssen Pharmaceutica Nv | مشتقات الكوينولين المضادة للجراثيم |
| JO2725B1 (en) * | 2006-12-06 | 2013-09-15 | جانسين فارماسوتيكا ان. في | Quinoline antibacterial derivatives |
| JO2685B1 (en) * | 2006-12-06 | 2013-03-03 | جانسين فارماسوتيكا ان في | Quinoline antibacterial derivatives |
| JO2970B1 (en) * | 2006-12-06 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Quinoline antibacterial derivatives |
| 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 |
| 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 |
| RU2486175C2 (ru) * | 2011-09-12 | 2013-06-27 | Закрытое Акционерное Общество "Фарм-Синтез" | Производные хинолина, в частности 5,6,7-замещенные 1-(2-хлорхинолин-3-ил)-4-диметиламино-2-(нафталин-1-ил)-1-фенилбутан-2-олы, способ получения и применение соединений |
| WO2013160431A1 (en) | 2012-04-27 | 2013-10-31 | Janssen Pharmaceutica Nv | Antibacterial quinoline derivatives |
| PL2841425T3 (pl) | 2012-04-27 | 2016-10-31 | Antybakteryjne pochodne chinoliny | |
| US9572809B2 (en) | 2012-07-18 | 2017-02-21 | Spero Trinem, Inc. | Combination therapy to treat Mycobacterium diseases |
| AU2013366572B2 (en) | 2012-12-21 | 2018-08-30 | Janssen Sciences Ireland Uc | Antibacterial compounds |
| RU2530493C1 (ru) * | 2013-04-22 | 2014-10-10 | Закрытое Акционерное Общество "Фарм-Синтез" | Производные хинолина, в частности 6,7-замещенные 1-(2-хлорхинолин-3-ил)-4-диметиламино-2-(нафталин-1-ил)-1-фенилбутан-2-олы, способ их получения и применение соединений для лечения инфекционных заболеваний микобактериальной природы, в частности туберкулеза |
| CN105017147B (zh) * | 2014-04-30 | 2019-02-01 | 中国医学科学院药物研究所 | 一种回收和利用Bedaquiline立体化学异构体的方法 |
| CN105085395B (zh) * | 2014-05-07 | 2017-09-26 | 国药集团国瑞药业有限公司 | 贝达喹啉的制备方法 |
| CN105085396B (zh) * | 2014-05-07 | 2017-08-08 | 国药集团国瑞药业有限公司 | 用于制备贝达喹啉的中间体及其制备方法和应用 |
| CN105198808B (zh) * | 2014-05-27 | 2017-08-25 | 北京万生药业有限责任公司 | 一种高效生产贝达喹啉的方法 |
| CN105175329B (zh) * | 2014-06-10 | 2017-09-19 | 重庆圣华曦药业股份有限公司 | 一种贝达喹啉消旋体的合成路线及方法 |
| 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 |
| JP6362235B2 (ja) * | 2014-07-14 | 2018-07-25 | ツーセン ファーマシューティカル カンパニー リミテッド | ピリジン誘導体およびその抗マイコバクテリウムにおける使用 |
| CN105440051B (zh) * | 2014-09-19 | 2019-07-05 | 重庆医药工业研究院有限责任公司 | 一种抗结核的噻吩吡啶衍生物 |
| CZ2014708A3 (cs) | 2014-10-16 | 2016-04-27 | Zentiva, K.S. | Soli Bedaquilinu |
| CZ201534A3 (cs) | 2015-01-21 | 2016-08-03 | Zentiva, K.S. | Nové možnosti chirální resoluce bedaquilinu |
| CZ201533A3 (cs) | 2015-01-21 | 2016-08-03 | Zentiva, K.S. | Způsob izolace směsi enantiomerů |
| CZ201535A3 (cs) | 2015-01-21 | 2016-08-03 | Zentiva, K.S. | Nové možnosti chirální resoluce bedaquilinu |
| AU2016212116B2 (en) | 2015-01-27 | 2021-07-15 | Janssen Pharmaceutica Nv | Dispersible compositions |
| US10674732B2 (en) * | 2015-04-29 | 2020-06-09 | The State Of Israel, Ministry Of Agriculture & Rural Development Agricultural Research Organization | Anti-phytopathogenic compositions |
| 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 |
| CZ2015391A3 (cs) | 2015-06-09 | 2016-12-21 | Zentiva, K.S. | Sůl bedaquilinu s kyselinou citronovou |
| ES2914681T3 (es) | 2015-07-02 | 2022-06-15 | Janssen Sciences Ireland Unlimited Co | Compuestos antibacterianos |
| CN105061387A (zh) * | 2015-07-17 | 2015-11-18 | 苏州大学 | 二芳基醚类稠环类化合物、制备方法和用途 |
| CN107848978B (zh) * | 2015-07-24 | 2021-04-02 | 浙江海正药业股份有限公司 | 一种分离贝达喹啉非对映异构体a的方法 |
| CN108349898B (zh) * | 2015-10-20 | 2021-03-23 | 浙江海正药业股份有限公司 | 富马酸贝达喹啉的晶型及其制备方法 |
| 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 |
| EP3423449B1 (en) * | 2016-03-03 | 2021-04-07 | Council of Scientific and Industrial Research | Substituted aurone alkaloids as anti-mycobacterial agents |
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