RU2520766C2 - Применение соединений 4-(пирролидин-1-ил)хинолина для уничтожения клинически латентных микроорганизмов - Google Patents
Применение соединений 4-(пирролидин-1-ил)хинолина для уничтожения клинически латентных микроорганизмов Download PDFInfo
- Publication number
- RU2520766C2 RU2520766C2 RU2009146828/15A RU2009146828A RU2520766C2 RU 2520766 C2 RU2520766 C2 RU 2520766C2 RU 2009146828/15 A RU2009146828/15 A RU 2009146828/15A RU 2009146828 A RU2009146828 A RU 2009146828A RU 2520766 C2 RU2520766 C2 RU 2520766C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- phenylpyrrolidin
- quinolin
- formula
- alkyl
- Prior art date
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- 244000005700 microbiome Species 0.000 title claims description 49
- KMHBJKGSMYLCDP-UHFFFAOYSA-N 4-pyrrolidin-1-ylquinoline Chemical class C1CCCN1C1=CC=NC2=CC=CC=C12 KMHBJKGSMYLCDP-UHFFFAOYSA-N 0.000 title abstract description 9
- 230000008030 elimination Effects 0.000 title 1
- 238000003379 elimination reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 124
- 239000003814 drug Substances 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 22
- 230000001580 bacterial effect Effects 0.000 claims abstract description 16
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 10
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 10
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 7
- 208000031888 Mycoses Diseases 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 326
- 125000001424 substituent group Chemical group 0.000 claims description 140
- -1 chloro, phenoxy, benzyloxy, 4-methanesulfonylbenzyloxy, 4-methoxybenzyloxy, 2-phenylethoxy, 5-methylisoxazol-3-ylmethoxy, benzylamino Chemical group 0.000 claims description 136
- 125000000217 alkyl group Chemical group 0.000 claims description 107
- 229910052736 halogen Inorganic materials 0.000 claims description 89
- 150000002367 halogens Chemical class 0.000 claims description 87
- 239000000203 mixture Substances 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 239000004599 antimicrobial Substances 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 229910052757 nitrogen Chemical group 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 230000000699 topical effect Effects 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
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- 229910052760 oxygen Inorganic materials 0.000 claims description 15
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- 239000002671 adjuvant Substances 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
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- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims description 10
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
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- WPVXJFDLBMEEAM-UHFFFAOYSA-N 4-(3-benzylpyrrolidin-1-yl)-2-methyl-6-phenoxyquinoline Chemical compound C=12C=C(OC=3C=CC=CC=3)C=CC2=NC(C)=CC=1N(C1)CCC1CC1=CC=CC=C1 WPVXJFDLBMEEAM-UHFFFAOYSA-N 0.000 claims description 6
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
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- DGMPVYSXXIOGJY-UHFFFAOYSA-N Fusaric acid Chemical compound CCCCC1=CC=C(C(O)=O)N=C1 DGMPVYSXXIOGJY-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
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- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
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- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims description 4
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| PCT/GB2008/001694 WO2008142384A1 (en) | 2007-05-17 | 2008-05-16 | Use of 4-(pyrrolidin-1-yl)quinoline compounds to kill clinically latent microorganisms |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017120225A1 (en) * | 2016-01-04 | 2017-07-13 | The Johns Hopkins University | Use of low dose emetine for inhibition of human cytomegalovirus (hcmv) |
| RU2758056C2 (ru) * | 2019-11-21 | 2021-10-26 | федеральное государственное бюджетное образовательное учреждение высшего образования "Ставропольский государственный аграрный университет" | Препарат для лечения отитов бактериальной и грибковой этиологии у собак |
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| JP2010095522A (ja) * | 2008-09-19 | 2010-04-30 | Sumitomo Chemical Co Ltd | 植物病原菌による植物病害を防除又は予防するための農業用組成物 |
| SI2552440T1 (sl) | 2010-03-30 | 2019-03-29 | Helperby Therapeutics Limited | Nove kombinacije in uporaba |
| EP2569302A1 (en) * | 2010-05-13 | 2013-03-20 | Amgen, Inc | Heteroaryloxyheterocyclyl compounds as pde10 inhibitors |
| GB201013207D0 (en) | 2010-08-05 | 2010-09-22 | Helperby Therapeutics Ltd | Novel combination |
| WO2012017215A1 (en) | 2010-08-05 | 2012-02-09 | Helperby Therapeutics Limited | Combination of a pyrroloquinoline compound and a beta-lactam antimicrobial agent, mupirocin or chlorhexidine |
| GB201015079D0 (en) | 2010-09-10 | 2010-10-27 | Helperby Therapeutics Ltd | Novel use |
| JP6804096B2 (ja) | 2015-04-11 | 2020-12-23 | ヘルパービー セラピューティクス リミテッドＨｅｌｐｅｒｂｙ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | 口腔用組成物 |
| US10329257B2 (en) | 2015-08-13 | 2019-06-25 | The Broad Institute, Inc. | Compositions and methods for treating tuberculosis |
| GB201518969D0 (en) | 2015-10-27 | 2015-12-09 | Helperby Therapeutics Ltd | Triple combination |
| KR102665309B1 (ko) * | 2016-10-27 | 2024-05-10 | 주식회사 엘지생활건강 | 코디세핀을 포함하는 구강질환 예방 또는 치료용 조성물 |
| GB201703898D0 (en) | 2017-03-10 | 2017-04-26 | Helperby Therapeautics Ltd | Method |
| RU2664177C1 (ru) * | 2017-08-07 | 2018-08-15 | федеральное государственное бюджетное образовательное учреждение высшего образования "Омский государственный медицинский университет" Министерства здравоохранения Российской Федерации (ФГБОУ ВО ОмГМУ Минздрава России) | Способ лечения абсцедирующих фурункулов верхней и нижней зон лица |
| CN111163766A (zh) * | 2017-08-17 | 2020-05-15 | 医肯纳肿瘤学公司 | Ahr抑制剂和其用途 |
| US10668046B2 (en) | 2017-12-18 | 2020-06-02 | Ansella Therapeutics, Inc. | Compositions and methods for preventing and treating conditions |
| CN110897032B (zh) * | 2019-11-19 | 2025-10-14 | 华南理工大学 | 一种发酵饲料蛋白及其制备方法与应用 |
| CN111544599B (zh) * | 2020-07-10 | 2020-12-01 | 有术肌肤管理(深圳)有限公司 | 一种用于治疗痤疮的化合物及其用于制备药物或化妆品的用途 |
| KR102461715B1 (ko) * | 2020-10-12 | 2022-11-02 | 대한민국 | 항균 및 항진균 활성을 나타내는 신균주 페니실리움 비세티 및 이의 용도 |
| CN114831924A (zh) * | 2021-03-17 | 2022-08-02 | 武汉恒信源药业有限公司 | 一种乌洛托品及其化合物的阴道局部给药制剂及用途 |
| CN113528388A (zh) * | 2021-07-19 | 2021-10-22 | 海南大学 | 珊瑚共生链霉菌、发酵生产放线菌素d的方法及应用 |
| SMT202500447T1 (it) | 2021-11-02 | 2026-01-12 | Flare Therapeutics Inc | Agonisti inversi di pparg e loro usi |
| JP2025513455A (ja) | 2022-04-22 | 2025-04-24 | 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 | 疼痛の治療のためのヘテロアリール化合物 |
| CN117323339A (zh) * | 2023-09-05 | 2024-01-02 | 中国科学院广州生物医药与健康研究院 | 偶氮丝氨酸在制备抗分枝杆菌的药物中的应用 |
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| RU2004113207A (ru) * | 2001-09-28 | 2005-05-27 | Ф.Хоффманн-Ля Рош Аг (Ch) | Хинолиновые производные в качестве антагонистов нейропептида y |
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| TW477787B (en) * | 1996-08-27 | 2002-03-01 | Pfizer | Pyrido six-membered nitrogen-containing cyclic ring derivatives having corticotropin releasing factor antagonist activity and pharmaceutical composition containing same |
| AU2002338896B2 (en) * | 2001-05-21 | 2006-04-27 | F.Hoffman-La Roche Ag | Quinoline derivatives as ligands for the neuropeptide Y receptor |
| EP1451156A4 (en) * | 2001-11-27 | 2005-05-25 | Merck & Co Inc | 4-AMINOCHINOLINVERBINDUNGEN |
| CA2489560A1 (en) * | 2002-06-27 | 2004-01-08 | Schering Aktiengesellschaft | Substituted quinoline ccr5 receptor antagonists |
| WO2004016321A2 (en) * | 2002-08-19 | 2004-02-26 | Avi Elbaz | Proprioceptive/kinesthetic apparatus and method |
| JP4602903B2 (ja) * | 2002-10-10 | 2010-12-22 | モルフォケム アクチェンゲゼルシャフト フュア コンビナトリシェ ヘミー | 抗菌活性を有する新規化合物 |
| CL2004000409A1 (es) * | 2003-03-03 | 2005-01-07 | Vertex Pharma | Compuestos derivados de 2-(cilo sustituido)-1-(amino u oxi sustituido)-quinazolina, inhibidores de canales ionicos de sodio y calcio dependientes de voltaje; composicion farmaceutica; y uso del compuesto en el tratamiento de dolor agudo, cronico, neu |
| DE102004041163A1 (de) * | 2004-08-25 | 2006-03-02 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen mit antibakterieller Aktivität |
| WO2006071875A1 (en) | 2004-12-29 | 2006-07-06 | Millennium Pharmaceuticals, Inc. | Compounds useful as chemokine receptor antagonists |
| US20060183763A1 (en) * | 2004-12-31 | 2006-08-17 | Pfizer Inc | Novel pyrrolidyl derivatives of heteroaromatic compounds |
| GB0522715D0 (en) * | 2005-11-08 | 2005-12-14 | Helperby Therapeutics Ltd | New use |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7074801B1 (en) * | 2001-04-26 | 2006-07-11 | Eisai Co., Ltd. | Nitrogen-containing condensed cyclic compound having a pyrazolyl group as a substituent group and pharmaceutical composition thereof |
| RU2004113207A (ru) * | 2001-09-28 | 2005-05-27 | Ф.Хоффманн-Ля Рош Аг (Ch) | Хинолиновые производные в качестве антагонистов нейропептида y |
| RU2298002C2 (ru) * | 2002-02-04 | 2007-04-27 | Ф. Хоффманн-Ля Рош Аг | Производные хинолина в качестве антагонистов npy |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017120225A1 (en) * | 2016-01-04 | 2017-07-13 | The Johns Hopkins University | Use of low dose emetine for inhibition of human cytomegalovirus (hcmv) |
| US11253511B2 (en) | 2016-01-04 | 2022-02-22 | The Johns Hopkins University | Use of low dose emetine for inhibition of human cytomegalovirus (HCMV) |
| RU2758056C2 (ru) * | 2019-11-21 | 2021-10-26 | федеральное государственное бюджетное образовательное учреждение высшего образования "Ставропольский государственный аграрный университет" | Препарат для лечения отитов бактериальной и грибковой этиологии у собак |
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| AU2008252636A1 (en) | 2008-11-27 |
| SI2182950T1 (en) | 2018-01-31 |
| HRP20171553T1 (hr) | 2017-12-15 |
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| IL201392A0 (en) | 2010-05-31 |
| EP2182950B8 (en) | 2017-08-23 |
| KR101599384B1 (ko) | 2016-03-03 |
| HUE034298T2 (en) | 2018-02-28 |
| BRPI0811745B1 (pt) | 2019-06-04 |
| DK2182950T3 (da) | 2017-11-06 |
| CN101795688A (zh) | 2010-08-04 |
| WO2008142384A1 (en) | 2008-11-27 |
| US20100305065A1 (en) | 2010-12-02 |
| BRPI0811745A2 (pt) | 2014-11-11 |
| EP2182950A1 (en) | 2010-05-12 |
| PL2182950T3 (pl) | 2018-01-31 |
| JP2010527346A (ja) | 2010-08-12 |
| AU2008252636B2 (en) | 2013-10-31 |
| PT2182950T (pt) | 2017-09-11 |
| RU2009146828A (ru) | 2011-06-27 |
| CN101795688B (zh) | 2015-05-20 |
| CA2684692A1 (en) | 2008-11-27 |
| JP5474768B2 (ja) | 2014-04-16 |
| CA2684692C (en) | 2016-07-05 |
| US8759348B2 (en) | 2014-06-24 |
| ES2637999T3 (es) | 2017-10-18 |
| MX2009012390A (es) | 2010-06-23 |
| EP2182950B1 (en) | 2017-07-19 |
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