JP2017505304A5 - - Google Patents
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- Publication number
- JP2017505304A5 JP2017505304A5 JP2016547848A JP2016547848A JP2017505304A5 JP 2017505304 A5 JP2017505304 A5 JP 2017505304A5 JP 2016547848 A JP2016547848 A JP 2016547848A JP 2016547848 A JP2016547848 A JP 2016547848A JP 2017505304 A5 JP2017505304 A5 JP 2017505304A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- methyl
- acetyl
- mutilin
- epi
- 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
- -1 -Carbamimidoyl Chemical group 0.000 claims 342
- 229960002771 retapamulin Drugs 0.000 claims 162
- OBUUFWIMEGVAQS-UHFFFAOYSA-N Pleuromutenol Natural products CC1C(O)C(C)(C=C)CC(O)C2(C)C(C)CCC31C2C(=O)CC3 OBUUFWIMEGVAQS-UHFFFAOYSA-N 0.000 claims 156
- STZYTFJPGGDRJD-NHUWBDDWSA-N retapamulin Chemical group C([C@H]([C@@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CS[C@@H]3C[C@H]4CC[C@H](N4C)C3)C)C[C@]32[C@H]1C(=O)CC3 STZYTFJPGGDRJD-NHUWBDDWSA-N 0.000 claims 151
- 125000000217 alkyl group Chemical group 0.000 claims 88
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 25
- 125000003118 aryl group Chemical group 0.000 claims 21
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 125000005842 heteroatom Chemical group 0.000 claims 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000001931 aliphatic group Chemical group 0.000 claims 5
- 125000003277 amino group Chemical group 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical group C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 claims 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 3
- 125000003368 amide group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 244000005700 microbiome Species 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 241000588724 Escherichia coli Species 0.000 claims 1
- ZRZNJUXESFHSIO-UHFFFAOYSA-N Pleuromutilin Natural products CC1C(O)C(C)(C=C)CC(OC(=O)CO)C2(C)C(C)CCC31C2C(=O)CC3 ZRZNJUXESFHSIO-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000003725 azepanyl group Chemical group 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
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14152107 | 2014-01-22 | ||
| EP14152107.0 | 2014-01-22 | ||
| PCT/EP2015/051159 WO2015110481A1 (en) | 2014-01-22 | 2015-01-21 | 12-epi-pleuromutilins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017505304A JP2017505304A (ja) | 2017-02-16 |
| JP2017505304A5 true JP2017505304A5 (OSRAM) | 2018-03-08 |
| JP6715772B2 JP6715772B2 (ja) | 2020-07-01 |
Family
ID=49999754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016547848A Expired - Fee Related JP6715772B2 (ja) | 2014-01-22 | 2015-01-21 | １２−ｅｐｉ−プロイロムチリン |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9701628B2 (OSRAM) |
| EP (1) | EP3096751B1 (OSRAM) |
| JP (1) | JP6715772B2 (OSRAM) |
| KR (1) | KR102267807B1 (OSRAM) |
| CN (1) | CN105916499B (OSRAM) |
| BR (1) | BR112016015542B1 (OSRAM) |
| CA (1) | CA2935415C (OSRAM) |
| ES (1) | ES2861318T3 (OSRAM) |
| IL (1) | IL246454A0 (OSRAM) |
| MX (1) | MX368101B (OSRAM) |
| WO (1) | WO2015110481A1 (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN109666009B (zh) * | 2018-11-02 | 2023-02-03 | 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 |
| KR20250069688A (ko) * | 2019-04-20 | 2025-05-19 | 광동 오포 모바일 텔레커뮤니케이션즈 코포레이션 리미티드 | Bdpcm에 기반한 영상 코딩 방법 및 그 장치 |
| WO2021209596A1 (en) | 2020-04-17 | 2021-10-21 | Nabriva Therapeutics GmbH | Therapeutic 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 |
| WO2025081213A1 (en) | 2023-10-21 | 2025-04-24 | Ariva Med Gmbh | NOVEL USES OF 12-EPI-MUTILIN COMPOUNDs |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000071560A1 (en) | 1999-05-20 | 2000-11-30 | Smithkline Beecham Corporation | Methods of modulating activity of prokaryotic ribosomes |
| JPWO2006070671A1 (ja) | 2004-12-27 | 2008-06-12 | 杏林製薬株式会社 | １２位置換ムチリン誘導体 |
| 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 |
| US8222407B2 (en) | 2007-05-24 | 2012-07-17 | Kyorin Pharmaceutical Co., Ltd. | Mutilin derivative having heterocyclic aromatic ring carboxylic acid structure in substituent at 14-position |
| 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 |
-
2015
- 2015-01-21 BR BR112016015542-4A patent/BR112016015542B1/pt not_active IP Right Cessation
- 2015-01-21 KR KR1020167022050A patent/KR102267807B1/ko not_active Expired - Fee Related
- 2015-01-21 ES ES15701513T patent/ES2861318T3/es active Active
- 2015-01-21 MX MX2016008781A patent/MX368101B/es active IP Right Grant
- 2015-01-21 CN CN201580005582.5A patent/CN105916499B/zh active Active
- 2015-01-21 WO PCT/EP2015/051159 patent/WO2015110481A1/en not_active Ceased
- 2015-01-21 CA CA2935415A patent/CA2935415C/en active Active
- 2015-01-21 US US15/111,390 patent/US9701628B2/en active Active
- 2015-01-21 EP EP15701513.2A patent/EP3096751B1/en active Active
- 2015-01-21 JP JP2016547848A patent/JP6715772B2/ja not_active Expired - Fee Related
-
2016
- 2016-06-26 IL IL246454A patent/IL246454A0/en active IP Right Grant
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