KR102267807B1 - 12-epi-플루로뮤틸린 - Google Patents
12-epi-플루로뮤틸린 Download PDFInfo
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- KR102267807B1 KR102267807B1 KR1020167022050A KR20167022050A KR102267807B1 KR 102267807 B1 KR102267807 B1 KR 102267807B1 KR 1020167022050 A KR1020167022050 A KR 1020167022050A KR 20167022050 A KR20167022050 A KR 20167022050A KR 102267807 B1 KR102267807 B1 KR 102267807B1
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- Prior art keywords
- amino
- methyl
- acetyl
- epi
- mutilin
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- 0 *c1ccc(CC(NCCCN)=O)cc1 Chemical compound *c1ccc(CC(NCCCN)=O)cc1 0.000 description 7
- DNUGOKVTBKQMNS-UHFFFAOYSA-N CC(C)CNCC=C Chemical compound CC(C)CNCC=C DNUGOKVTBKQMNS-UHFFFAOYSA-N 0.000 description 1
- KZEVCRGCBNESNK-UHFFFAOYSA-N CC(C)CNCCCCCCN Chemical compound CC(C)CNCCCCCCN KZEVCRGCBNESNK-UHFFFAOYSA-N 0.000 description 1
- NLGBMJGHKURYSR-UHFFFAOYSA-N CC(C)CNCCCCCCNC(N)=N Chemical compound CC(C)CNCCCCCCNC(N)=N NLGBMJGHKURYSR-UHFFFAOYSA-N 0.000 description 1
- RXRAXCXECHYZFI-UHFFFAOYSA-N CC(C)CNCCCCCCO Chemical compound CC(C)CNCCCCCCO RXRAXCXECHYZFI-UHFFFAOYSA-N 0.000 description 1
- NPTOAGPGIORAQT-UHFFFAOYSA-N CC(C)CNCCCCN Chemical compound CC(C)CNCCCCN NPTOAGPGIORAQT-UHFFFAOYSA-N 0.000 description 1
- MBUAMOKJRSMXKM-UHFFFAOYSA-N CC(C)CNCCCN Chemical compound CC(C)CNCCCN MBUAMOKJRSMXKM-UHFFFAOYSA-N 0.000 description 1
- RTHONOKQGRUZLA-UHFFFAOYSA-N CC(C)c(cc1)ccc1C(NCCCN)=O Chemical compound CC(C)c(cc1)ccc1C(NCCCN)=O RTHONOKQGRUZLA-UHFFFAOYSA-N 0.000 description 1
- KYJWQRRUVTWJHQ-UHFFFAOYSA-N CC(C)c1ccc(C(C)(NCCCN)O)cc1 Chemical compound CC(C)c1ccc(C(C)(NCCCN)O)cc1 KYJWQRRUVTWJHQ-UHFFFAOYSA-N 0.000 description 1
- OCCJEHKMAWNCRG-UHFFFAOYSA-N CC(C)c1ccc(CC(NCCN)=O)cc1 Chemical compound CC(C)c1ccc(CC(NCCN)=O)cc1 OCCJEHKMAWNCRG-UHFFFAOYSA-N 0.000 description 1
- BQWXXKIQZJQCQM-HNZWMWIHSA-N CC(CC[C@](CCC1)(C[C@@H]([C@@](C)(C2)C=C)O)[C@H]3C1=O)[C@@]3(C)[C@@H]2OC(COS(c1ccc(C)cc1)(=O)=O)=O Chemical compound CC(CC[C@](CCC1)(C[C@@H]([C@@](C)(C2)C=C)O)[C@H]3C1=O)[C@@]3(C)[C@@H]2OC(COS(c1ccc(C)cc1)(=O)=O)=O BQWXXKIQZJQCQM-HNZWMWIHSA-N 0.000 description 1
- FDESNDUXFBVGTO-BPDQFDRRSA-N C[C@H](CCC[C@H]1C(CCC[C@@H](C)[C@@H]([C@@](C)(CNCCCN)C2)O)=O)[C@@]1(C)[C@@H]2OC(CSc1c(CN)ccc(CN)c1)=O Chemical compound C[C@H](CCC[C@H]1C(CCC[C@@H](C)[C@@H]([C@@](C)(CNCCCN)C2)O)=O)[C@@]1(C)[C@@H]2OC(CSc1c(CN)ccc(CN)c1)=O FDESNDUXFBVGTO-BPDQFDRRSA-N 0.000 description 1
- ATKJFKYXLYQNGA-NNHOPPIZSA-N C[C@H](CC[C@@](CC1)([C@H]2C1=O)[C@@H](C)[C@@H]([C@@](C)(CNCc(cc1)ccc1OCCN)C1)O)[C@@]2(C)[C@@H]1OC(CSC(CC1)CCN1C(CN)=O)=O Chemical compound C[C@H](CC[C@@](CC1)([C@H]2C1=O)[C@@H](C)[C@@H]([C@@](C)(CNCc(cc1)ccc1OCCN)C1)O)[C@@]2(C)[C@@H]1OC(CSC(CC1)CCN1C(CN)=O)=O ATKJFKYXLYQNGA-NNHOPPIZSA-N 0.000 description 1
- MHAXOLPCUQUZFQ-GVZVBGTISA-N C[C@H](C[C@H]1C2)[C@@](C)([C@@H](C[C@]3(C)C/C=N/O)OC(COS(c4ccc(C)cc4)(=O)=O)=O)C1(CCC1)[C@@]21[C@@H](C)C3=O Chemical compound C[C@H](C[C@H]1C2)[C@@](C)([C@@H](C[C@]3(C)C/C=N/O)OC(COS(c4ccc(C)cc4)(=O)=O)=O)C1(CCC1)[C@@]21[C@@H](C)C3=O MHAXOLPCUQUZFQ-GVZVBGTISA-N 0.000 description 1
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- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
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- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
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- C07D473/24—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one nitrogen and one sulfur atom
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- C07D473/36—Sulfur atom
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- C07C2603/76—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members
- C07C2603/80—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members containing eight-membered rings
- C07C2603/82—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members containing eight-membered rings having three condensed rings with in total fourteen carbon atoms and having a having a [5.4.3.0(1,8)] ring structure, e.g. pleuromutiline
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| TWI762573B (zh) | 2017-02-10 | 2022-05-01 | 奧地利商納畢瓦治療有限責任公司 | 截短側耳素之純化 |
| CN107235971B (zh) * | 2017-07-31 | 2019-11-12 | 重庆华邦胜凯制药有限公司 | 一种制备瑞他莫林的新方法 |
| CN115197169B (zh) * | 2018-11-02 | 2023-07-11 | 华南农业大学 | 一种以2-氨基苯巯醇为连接基团截短侧耳素衍生物制备方法和用途 |
| WO2020210158A1 (en) * | 2019-04-06 | 2020-10-15 | The Board Of Trustees Of The University Of Illinois | Compounds that induce ferroptic cell death |
| JP7260665B2 (ja) | 2019-04-20 | 2023-04-18 | エルジー エレクトロニクス インコーポレイティド | Bdpcmに基づく映像コーディング方法、及びその装置 |
| EP4135683B9 (en) * | 2020-04-17 | 2025-12-10 | ARIVA Med GmbH | Antiviral use of pleuromutilins |
| WO2021219399A1 (en) | 2020-04-28 | 2021-11-04 | Nabriva Therapeutics GmbH | Novel 12-epi-mutilin compounds, process for preparing the same and uses thereof |
| US11351149B2 (en) | 2020-09-03 | 2022-06-07 | Pfizer Inc. | Nitrile-containing antiviral compounds |
| US11117859B1 (en) * | 2021-02-12 | 2021-09-14 | Shaanxi University Of Science And Technology | Pleuromutilin hippuric acid ester with antibacterial activity and a method of preparing the same |
| CN117500809A (zh) * | 2021-04-16 | 2024-02-02 | 纳布里瓦治疗有限责任公司 | 新的12-差向异构-莫林化合物及其用途 |
| CN116199690B (zh) * | 2023-04-28 | 2023-07-07 | 西华大学 | 嘌呤类截短侧耳素衍生物、立体异构体或药学上可接受的盐及其用途和药物组合物 |
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| WO2000071560A1 (en) | 1999-05-20 | 2000-11-30 | Smithkline Beecham Corporation | Methods of modulating activity of prokaryotic ribosomes |
| EP1832591A1 (en) | 2004-12-27 | 2007-09-12 | Kyorin Pharmaceutical Co., Ltd. | 12-position substituted mutilin derivative |
| JP2006306727A (ja) * | 2005-04-26 | 2006-11-09 | Kyorin Pharmaceut Co Ltd | ピリジン環を14位置換基に有する12位置換ムチリン誘導体 |
| GB0513058D0 (en) | 2005-06-27 | 2005-08-03 | Sandoz Ag | Organic compounds |
| EP1896404B1 (en) * | 2005-06-27 | 2014-09-17 | Nabriva Therapeutics AG | Pleuromutilin derivatives containing a hydroxyamino- or acyloxyaminocycloalkyl group |
| EP1808431A1 (en) * | 2006-01-16 | 2007-07-18 | Nabriva Therapeutics Forschungs GmbH | Mutilin derivatives and their use as pharmaceutical |
| WO2008117796A1 (ja) | 2007-03-28 | 2008-10-02 | Dainippon Sumitomo Pharma Co., Ltd. | 新規ムチリン誘導体 |
| JP2008280297A (ja) * | 2007-05-11 | 2008-11-20 | Kyorin Pharmaceut Co Ltd | 12位ヘテロ置換ムチリン誘導体 |
| EP2149571A4 (en) | 2007-05-24 | 2010-09-01 | Kyorin Seiyaku Kk | MUTILINE DERIVATIVE WITH A RINGED, HETEROCYCLIC AND AROMATIC CARBOXYLIC ACID STRUCTURE IN A SUBSTITUTE AT POSITION 14 |
| EP2014640A1 (en) * | 2007-07-13 | 2009-01-14 | Nabriva Therapeutics AG | Pleuromutilin derivatives |
| JP2009040709A (ja) * | 2007-08-08 | 2009-02-26 | Kyorin Pharmaceut Co Ltd | 12位置換ムチリン誘導体 |
| EP2159220A1 (en) | 2008-09-02 | 2010-03-03 | Nabriva Therapeutics AG | Organic compounds |
| JP2010100582A (ja) | 2008-10-24 | 2010-05-06 | Kyorin Pharmaceut Co Ltd | 14位置換基に複素芳香環カルボン酸構造を有するムチリン誘導体 |
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Non-Patent Citations (1)
| Title |
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| Monatshefte fur Chemie, Vol.117, pp.1073-1080, 1986* |
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St.27 status event code: N-4-6-H10-H13-oth-PC1903 Ip right cessation event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE Not in force date: 20240617 |