JP2018527367A5 - - Google Patents
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- JP2018527367A5 JP2018527367A5 JP2018513579A JP2018513579A JP2018527367A5 JP 2018527367 A5 JP2018527367 A5 JP 2018527367A5 JP 2018513579 A JP2018513579 A JP 2018513579A JP 2018513579 A JP2018513579 A JP 2018513579A JP 2018527367 A5 JP2018527367 A5 JP 2018527367A5
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- Japan
- Prior art keywords
- mixture
- formula
- compound
- acid
- compounds
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims 37
- 239000000203 mixture Substances 0.000 claims 36
- 238000000034 method Methods 0.000 claims 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 14
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 8
- 239000011877 solvent mixture Substances 0.000 claims 8
- 239000003054 catalyst Substances 0.000 claims 6
- 238000002425 crystallisation Methods 0.000 claims 6
- 230000008025 crystallization Effects 0.000 claims 6
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims 3
- 239000011833 salt mixture Substances 0.000 claims 3
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 2
- OCQAXYHNMWVLRH-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 OCQAXYHNMWVLRH-UHFFFAOYSA-N 0.000 claims 2
- NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 2
- 230000002152 alkylating effect Effects 0.000 claims 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 2
- 230000000843 anti-fungal effect Effects 0.000 claims 2
- 229940121375 antifungal agent Drugs 0.000 claims 2
- 229960005070 ascorbic acid Drugs 0.000 claims 2
- 235000010323 ascorbic acid Nutrition 0.000 claims 2
- 239000011668 ascorbic acid Substances 0.000 claims 2
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 claims 2
- 235000011090 malic acid Nutrition 0.000 claims 2
- 239000001630 malic acid Substances 0.000 claims 2
- 235000002906 tartaric acid Nutrition 0.000 claims 2
- 239000011975 tartaric acid Substances 0.000 claims 2
- 150000003536 tetrazoles Chemical class 0.000 claims 2
- 238000006254 arylation reaction Methods 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 *c1cnc(C(C(c(c(F)c2)ccc2F)=O)(F)F)cc1 Chemical compound *c1cnc(C(C(c(c(F)c2)ccc2F)=O)(F)F)cc1 0.000 description 2
- UDGASIIGNCBLSI-PMERELPUSA-N N#Cc1ccc(COc(cc2)ccc2C#Cc2cnc(C([C@](C[n]3nnnc3)(c(c(F)c3)ccc3F)O)(F)F)cc2)cc1 Chemical compound N#Cc1ccc(COc(cc2)ccc2C#Cc2cnc(C([C@](C[n]3nnnc3)(c(c(F)c3)ccc3F)O)(F)F)cc2)cc1 UDGASIIGNCBLSI-PMERELPUSA-N 0.000 description 2
- LBBHRBLMMYBWEM-VGFJAJBZSA-N N#Cc1ccc(COC(C=C2)=CC=CC2C#Cc2cnc(C([C@@](C[n]3nnnc3)(c(c(F)c3)ccc3F)O)(F)F)cc2)cc1 Chemical compound N#Cc1ccc(COC(C=C2)=CC=CC2C#Cc2cnc(C([C@@](C[n]3nnnc3)(c(c(F)c3)ccc3F)O)(F)F)cc2)cc1 LBBHRBLMMYBWEM-VGFJAJBZSA-N 0.000 description 1
- JFHOATHDSUPBNY-SSEXGKCCSA-N N#Cc1ccc(COc(cc2)ccc2C#Cc2cnc(C([C@@H](c(c(F)c3)ccc3F)/[O]=C/[n]3nnnc3)(F)F)cc2)cc1 Chemical compound N#Cc1ccc(COc(cc2)ccc2C#Cc2cnc(C([C@@H](c(c(F)c3)ccc3F)/[O]=C/[n]3nnnc3)(F)F)cc2)cc1 JFHOATHDSUPBNY-SSEXGKCCSA-N 0.000 description 1
- UDGASIIGNCBLSI-SSEXGKCCSA-N N#Cc1ccc(COc(cc2)ccc2C#Cc2cnc(C([C@@](C[n]3nnnc3)(c(c(F)c3)ccc3F)O)(F)F)cc2)cc1 Chemical compound N#Cc1ccc(COc(cc2)ccc2C#Cc2cnc(C([C@@](C[n]3nnnc3)(c(c(F)c3)ccc3F)O)(F)F)cc2)cc1 UDGASIIGNCBLSI-SSEXGKCCSA-N 0.000 description 1
- RKDYIOGHCIESBV-MUUNZHRXSA-N N#Cc1ccc(COc(cc2)ccc2C#Cc2cnc(C([C@H](C[n]3nnnc3)c(ccc(F)c3)c3F)(F)F)cc2)cc1 Chemical compound N#Cc1ccc(COc(cc2)ccc2C#Cc2cnc(C([C@H](C[n]3nnnc3)c(ccc(F)c3)c3F)(F)F)cc2)cc1 RKDYIOGHCIESBV-MUUNZHRXSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562220384P | 2015-09-18 | 2015-09-18 | |
| US62/220,384 | 2015-09-18 | ||
| US201662275504P | 2016-01-06 | 2016-01-06 | |
| US62/275,504 | 2016-01-06 | ||
| PCT/US2016/052151 WO2017049096A1 (en) | 2015-09-18 | 2016-09-16 | Antifungal compound process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018527367A JP2018527367A (ja) | 2018-09-20 |
| JP2018527367A5 true JP2018527367A5 (cg-RX-API-DMAC7.html) | 2019-07-25 |
| JP6887993B2 JP6887993B2 (ja) | 2021-06-16 |
Family
ID=58289604
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018513603A Pending JP2018532719A (ja) | 2015-09-18 | 2016-09-16 | 抗真菌化合物および作製方法 |
| JP2018514436A Active JP6847458B2 (ja) | 2015-09-18 | 2016-09-16 | 抗真菌化合物のプロセス |
| JP2018513579A Expired - Fee Related JP6887993B2 (ja) | 2015-09-18 | 2016-09-16 | 抗真菌化合物調製方法 |
| JP2021083727A Pending JP2021121606A (ja) | 2015-09-18 | 2021-05-18 | 抗真菌化合物および作製方法 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018513603A Pending JP2018532719A (ja) | 2015-09-18 | 2016-09-16 | 抗真菌化合物および作製方法 |
| JP2018514436A Active JP6847458B2 (ja) | 2015-09-18 | 2016-09-16 | 抗真菌化合物のプロセス |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021083727A Pending JP2021121606A (ja) | 2015-09-18 | 2021-05-18 | 抗真菌化合物および作製方法 |
Country Status (17)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017507991A (ja) | 2014-03-19 | 2017-03-23 | ヴィアメット ファーマスーティカルズ，インコーポレイテッド | 抗真菌化合物の調製方法 |
| CA2942972A1 (en) | 2014-03-19 | 2015-09-24 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Antifungal compound process |
| BR112016021257B1 (pt) | 2014-03-19 | 2021-03-02 | Viamet Pharmaceuticals (NC), Inc. | 2-(2,4- difluorofenil-1,1-diflúor-1-(5-substituído-piridin-2-il)-3- (1h-tetrazol-1-il)propan-2-óis e processos para preparação e uso dos mesmos |
| EP3119756B9 (en) | 2014-03-19 | 2021-08-25 | Dow AgroSciences LLC | 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1h-tetrazol-1-yl)propan-2-ols and processes for their preparation |
| AU2015231216B2 (en) | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| EA201691648A1 (ru) | 2014-03-19 | 2017-01-30 | Ваймет Фармасьютикалс, Инк. | Способ получения противогрибковых соединений |
| KR102151082B1 (ko) | 2014-03-19 | 2020-09-03 | 더 유나이티드 스테이츠 오브 어메리카, 애즈 리프리젠티드 바이 더 시크리터리, 디파트먼트 오브 헬쓰 앤드 휴먼 서비시스 | 항진균 화합물 제조방법 |
| US10017494B2 (en) | 2014-03-19 | 2018-07-10 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| AU2015231275B2 (en) | 2014-03-19 | 2019-03-07 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| KR102798709B1 (ko) | 2015-09-18 | 2025-04-23 | 마이코비아 파마슈티컬즈, 인코포레이티드 | 항진균 화합물 제조 방법 |
| CN109666019B (zh) * | 2017-10-14 | 2021-04-06 | 朱允涛 | 一种氘代的氮唑醇类化合物及其制备方法和用途 |
| JP2021502402A (ja) | 2017-11-13 | 2021-01-28 | バイエル アクチェンゲゼルシャフトＢａｙｅｒ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | テトラゾリルプロピル誘導体および殺真菌剤としてのそれらの使用 |
| WO2021188404A1 (en) * | 2020-03-19 | 2021-09-23 | Assia Chemical Industries Ltd | Solid state forms of oteseconazole and process for preparation thereof |
| CA3226998A1 (en) * | 2021-07-22 | 2023-01-26 | Mycovia Pharmaceuticals, Inc. | Compositions comprising oteseconazole |
| CN114573503B (zh) * | 2022-03-28 | 2024-04-09 | 浙江天宇药业股份有限公司 | 一种制备奥特康唑中间体的方法 |
| CN114573557B (zh) * | 2022-03-28 | 2024-03-08 | 浙江天宇药业股份有限公司 | 一种奥特康唑的制备方法 |
| CN116621816B (zh) * | 2022-09-23 | 2025-07-04 | 北京莱瑞森医药科技有限公司 | 一种伏立康唑对映异构对b的拆分方法 |
| WO2024067784A1 (zh) * | 2022-09-30 | 2024-04-04 | 上海济煜医药科技有限公司 | 双环类化合物的无定形、结晶固体及其制备方法 |
| CN119798219B (zh) * | 2025-01-13 | 2025-07-18 | 长治医学院 | 一种奥特康唑的制备方法 |
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| CA2915054A1 (en) | 2013-06-12 | 2014-12-18 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| US10017494B2 (en) | 2014-03-19 | 2018-07-10 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| AU2015231270B2 (en) * | 2014-03-19 | 2019-03-07 | Viamet Pharmaceuticals (NC), Inc. | Antifungal compound process |
| AU2015231216B2 (en) | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| AU2015231275B2 (en) * | 2014-03-19 | 2019-03-07 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| EA201691648A1 (ru) | 2014-03-19 | 2017-01-30 | Ваймет Фармасьютикалс, Инк. | Способ получения противогрибковых соединений |
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| EP3119756B9 (en) | 2014-03-19 | 2021-08-25 | Dow AgroSciences LLC | 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1h-tetrazol-1-yl)propan-2-ols and processes for their preparation |
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