RU2015138797A - Конвергентные способы получения макролидных антибактериальных агентов - Google Patents
Конвергентные способы получения макролидных антибактериальных агентов Download PDFInfo
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- RU2015138797A RU2015138797A RU2015138797A RU2015138797A RU2015138797A RU 2015138797 A RU2015138797 A RU 2015138797A RU 2015138797 A RU2015138797 A RU 2015138797A RU 2015138797 A RU2015138797 A RU 2015138797A RU 2015138797 A RU2015138797 A RU 2015138797A
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- 238000000034 method Methods 0.000 title claims 29
- 239000003242 anti bacterial agent Substances 0.000 title 1
- 239000003120 macrolide antibiotic agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 102
- 150000003839 salts Chemical class 0.000 claims 50
- 238000005266 casting Methods 0.000 claims 23
- 239000003795 chemical substances by application Substances 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000006239 protecting group Chemical group 0.000 claims 6
- 150000001412 amines Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000007800 oxidant agent Substances 0.000 claims 4
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 239000012351 deprotecting agent Substances 0.000 claims 3
- 238000010511 deprotection reaction Methods 0.000 claims 3
- 239000012025 fluorinating agent Substances 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000006242 amine protecting group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- VTJCSBJRQLZNHE-CSMHCCOUSA-N desosamine Chemical compound C[C@@H](O)C[C@H](N(C)C)[C@@H](O)C=O VTJCSBJRQLZNHE-CSMHCCOUSA-N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 230000001681 protective effect Effects 0.000 claims 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical group FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 2
- GGRWVWTZLKVQNI-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) hydrogen sulfate Chemical compound OS(=O)(=O)OC1=C(F)C(F)=C(F)C(F)=C1F GGRWVWTZLKVQNI-UHFFFAOYSA-N 0.000 claims 1
- 238000005675 Corey-Kim oxidation reaction Methods 0.000 claims 1
- ZOYWWAGVGBSJDL-UHFFFAOYSA-N D-desosamine Natural products CC1CC(N(C)C)C(O)C(O)O1 ZOYWWAGVGBSJDL-UHFFFAOYSA-N 0.000 claims 1
- -1 HOBt Chemical compound 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000006809 Jones oxidation reaction Methods 0.000 claims 1
- 229910019093 NaOCl Inorganic materials 0.000 claims 1
- 238000006859 Swern oxidation reaction Methods 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000006184 cosolvent Substances 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
- 230000000640 hydroxylating effect Effects 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 1
- RLKHFSNWQCZBDC-UHFFFAOYSA-N n-(benzenesulfonyl)-n-fluorobenzenesulfonamide Chemical group C=1C=CC=CC=1S(=O)(=O)N(F)S(=O)(=O)C1=CC=CC=C1 RLKHFSNWQCZBDC-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000012363 selectfluor Substances 0.000 claims 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylene diamine Substances C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361786914P | 2013-03-15 | 2013-03-15 | |
| US61/786,914 | 2013-03-15 | ||
| PCT/US2014/029932 WO2014145210A1 (en) | 2013-03-15 | 2014-03-15 | Convergent processes for preparing macrolide antibacterial agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2015138797A true RU2015138797A (ru) | 2017-04-24 |
| RU2015138797A3 RU2015138797A3 (enExample) | 2018-02-28 |
Family
ID=51537907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015138797A RU2015138797A (ru) | 2013-03-15 | 2014-03-15 | Конвергентные способы получения макролидных антибактериальных агентов |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US9751908B2 (enExample) |
| EP (1) | EP2968384A4 (enExample) |
| JP (1) | JP6675973B2 (enExample) |
| KR (1) | KR20160020403A (enExample) |
| CN (1) | CN105188712A (enExample) |
| AU (1) | AU2014233240B2 (enExample) |
| BR (1) | BR112015023670A2 (enExample) |
| CA (1) | CA2907085A1 (enExample) |
| HK (2) | HK1218864A1 (enExample) |
| MX (1) | MX356772B (enExample) |
| RU (1) | RU2015138797A (enExample) |
| WO (1) | WO2014145210A1 (enExample) |
| ZA (1) | ZA201507551B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2772254A3 (en) | 2003-03-10 | 2015-03-11 | Optimer Pharmaceuticals, Inc. | Novel Antibacterial Agents |
| JP5698979B2 (ja) | 2007-10-25 | 2015-04-08 | センプラ ファーマシューティカルズ，インコーポレイテッド | マクロライド系抗菌剤の調製プロセス |
| EP2358379B1 (en) | 2008-10-24 | 2015-12-16 | Cempra Pharmaceuticals, Inc. | Biodefenses using triazole-containing macrolides |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| EP2475253B1 (en) | 2009-09-10 | 2016-10-26 | Cempra Pharmaceuticals, Inc. | Methods for treating malaria, tuberculosis and mac diseases |
| RU2608390C2 (ru) | 2010-05-20 | 2017-01-18 | Семпра Фармасьютикалз, Инк. | Способы получения макролидов и кетолидов, и промежуточных соединений для их получения |
| WO2012034058A1 (en) | 2010-09-10 | 2012-03-15 | Cempra Pharmaceuticals, Inc. | Hydrogen bond forming fluoro ketolides for treating diseases |
| JP6208742B2 (ja) | 2012-03-27 | 2017-10-04 | センプラ ファーマシューティカルズ，インコーポレイテッド | マクロライド抗生物質を投与するための非経口製剤 |
| US9861616B2 (en) | 2013-03-14 | 2018-01-09 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| US9751908B2 (en) | 2013-03-15 | 2017-09-05 | Cempra Pharmaceuticals, Inc. | Convergent processes for preparing macrolide antibacterial agents |
| BR112015025159A2 (pt) | 2013-04-04 | 2017-07-18 | Harvard College | macrolídeos e métodos de sua preparação e uso |
| JP2017531663A (ja) | 2014-10-08 | 2017-10-26 | プレジデント アンド フェローズ オブ ハーバード カレッジ | １４員ケトライドならびにそれらの調製および使用の方法 |
| CN104650166B (zh) * | 2014-11-17 | 2017-12-05 | 广东东阳光药业有限公司 | 一种大环内酯的制备方法 |
| WO2016144833A1 (en) * | 2015-03-06 | 2016-09-15 | Cempra Pharmaceuticals, Inc. | Processes for preparing fluoroketolides |
| WO2016154591A1 (en) | 2015-03-25 | 2016-09-29 | President And Fellows Of Harvard College | Macrolides with modified desosamine sugars and uses thereof |
| CN106554381A (zh) * | 2015-09-25 | 2017-04-05 | 苏州鹏旭医药科技有限公司 | 酮内酯类抗生素中间体及其制备方法和应用 |
| CN105503976B (zh) * | 2015-12-04 | 2018-02-06 | 浙江京新药业股份有限公司 | 一种索利霉素中间体 |
| EP3190122A1 (en) | 2016-01-08 | 2017-07-12 | LEK Pharmaceuticals d.d. | A novel synthetic pathway towards solithromycin and purification thereof |
| CN106432383A (zh) * | 2016-09-14 | 2017-02-22 | 重庆两江药物研发中心有限公司 | 索利霉素及其中间体的制备方法 |
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2014
- 2014-03-15 US US14/774,843 patent/US9751908B2/en not_active Expired - Fee Related
- 2014-03-15 CA CA2907085A patent/CA2907085A1/en not_active Abandoned
- 2014-03-15 BR BR112015023670A patent/BR112015023670A2/pt not_active Application Discontinuation
- 2014-03-15 HK HK16106891.9A patent/HK1218864A1/zh unknown
- 2014-03-15 WO PCT/US2014/029932 patent/WO2014145210A1/en not_active Ceased
- 2014-03-15 EP EP14763625.2A patent/EP2968384A4/en not_active Withdrawn
- 2014-03-15 HK HK16108554.3A patent/HK1220394A1/zh unknown
- 2014-03-15 RU RU2015138797A patent/RU2015138797A/ru not_active Application Discontinuation
- 2014-03-15 KR KR1020157026223A patent/KR20160020403A/ko not_active Withdrawn
- 2014-03-15 MX MX2015012465A patent/MX356772B/es active IP Right Grant
- 2014-03-15 AU AU2014233240A patent/AU2014233240B2/en not_active Ceased
- 2014-03-15 CN CN201480025203.4A patent/CN105188712A/zh active Pending
- 2014-03-15 JP JP2016503284A patent/JP6675973B2/ja not_active Expired - Fee Related
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2015
- 2015-10-12 ZA ZA2015/07551A patent/ZA201507551B/en unknown
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2018
- 2018-02-20 US US15/899,844 patent/US20190023731A1/en not_active Abandoned
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2019
- 2019-10-11 US US16/600,146 patent/US20200040024A1/en not_active Abandoned
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| MX2015012465A (es) | 2016-05-31 |
| ZA201507551B (en) | 2017-11-29 |
| EP2968384A4 (en) | 2017-02-15 |
| JP6675973B2 (ja) | 2020-04-08 |
| EP2968384A1 (en) | 2016-01-20 |
| CN105188712A (zh) | 2015-12-23 |
| WO2014145210A1 (en) | 2014-09-18 |
| HK1220394A1 (zh) | 2017-05-05 |
| BR112015023670A2 (pt) | 2017-07-18 |
| CA2907085A1 (en) | 2014-09-18 |
| US20160046660A1 (en) | 2016-02-18 |
| HK1218864A1 (zh) | 2017-03-17 |
| US20200040024A1 (en) | 2020-02-06 |
| US20190023731A1 (en) | 2019-01-24 |
| AU2014233240B2 (en) | 2018-08-09 |
| AU2014233240A1 (en) | 2015-10-01 |
| JP2016514699A (ja) | 2016-05-23 |
| MX356772B (es) | 2018-06-13 |
| KR20160020403A (ko) | 2016-02-23 |
| US9751908B2 (en) | 2017-09-05 |
| RU2015138797A3 (enExample) | 2018-02-28 |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
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