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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- JP
- Japan
- Prior art keywords
- mixture
- formula
- compound
- acid
- compounds
- 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.)
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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 (enExample) | 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)
| Country | Link |
|---|---|
| US (4) | US10513505B2 (enExample) |
| EP (3) | EP3349586B1 (enExample) |
| JP (4) | JP2018532719A (enExample) |
| KR (3) | KR20180053393A (enExample) |
| CN (3) | CN108348511A (enExample) |
| AU (3) | AU2016323782B2 (enExample) |
| BR (2) | BR112018005198A2 (enExample) |
| CA (3) | CA2998808A1 (enExample) |
| EA (3) | EA038214B1 (enExample) |
| ES (2) | ES2858314T3 (enExample) |
| HK (3) | HK1263287A1 (enExample) |
| HU (1) | HUE053638T2 (enExample) |
| MX (3) | MX2018003284A (enExample) |
| PL (1) | PL3349586T3 (enExample) |
| TW (3) | TWI723047B (enExample) |
| WO (3) | WO2017049080A1 (enExample) |
| ZA (1) | ZA201801404B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2015231275B2 (en) | 2014-03-19 | 2019-03-07 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| JP6572234B2 (ja) | 2014-03-19 | 2019-09-04 | ヴィアメット ファーマスーティカルズ（エヌシー），インコーポレイテッド | 抗真菌化合物の調製方法 |
| EP3119753B1 (en) | 2014-03-19 | 2020-11-04 | 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 |
| BR112016020937B1 (pt) | 2014-03-19 | 2022-09-20 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Processo de preparação de compostos antifúngicos |
| WO2015143180A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| CA2942936A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| AU2015231208B2 (en) | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| CA2942231A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| KR102441243B1 (ko) | 2014-03-19 | 2022-09-07 | 브이피에스-3, 엘엘씨 | 2-(2,4-디플루오르페닐)-1,1-디플루오르-1-(5-치환된-피리딘-2-일)-3-(1h-테트라졸-1-일)프로판-2-올 및 이의 제조방법 |
| HK1263287A1 (zh) | 2015-09-18 | 2020-03-20 | Nqp 1598, Ltd. | 抗真菌化合物和制备方法 |
| 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 |
| US11213031B2 (en) | 2017-11-13 | 2022-01-04 | Bayer Aktiengesellschaft | Tetrazolylpropyl derivatives and their use as fungicides |
| WO2021188404A1 (en) * | 2020-03-19 | 2021-09-23 | Assia Chemical Industries Ltd | Solid state forms of oteseconazole and process for preparation thereof |
| EP4373490A4 (en) * | 2021-07-22 | 2025-05-21 | Mycovia Pharmaceuticals, Inc. | COMPOSITIONS COMPRISING OTESECONAZOLE |
| 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 |
| 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 |
| 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 |
| CN119855811A (zh) * | 2022-09-30 | 2025-04-18 | 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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| AU2015231275B2 (en) | 2014-03-19 | 2019-03-07 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| US9802914B2 (en) | 2014-03-19 | 2017-10-31 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| CA2942936A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| WO2015143180A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| KR102441243B1 (ko) | 2014-03-19 | 2022-09-07 | 브이피에스-3, 엘엘씨 | 2-(2,4-디플루오르페닐)-1,1-디플루오르-1-(5-치환된-피리딘-2-일)-3-(1h-테트라졸-1-일)프로판-2-올 및 이의 제조방법 |
| BR112016020937B1 (pt) * | 2014-03-19 | 2022-09-20 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Processo de preparação de compostos antifúngicos |
| AU2015231208B2 (en) | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| JP6572234B2 (ja) * | 2014-03-19 | 2019-09-04 | ヴィアメット ファーマスーティカルズ（エヌシー），インコーポレイテッド | 抗真菌化合物の調製方法 |
| EP3119753B1 (en) | 2014-03-19 | 2020-11-04 | 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 |
| CA2942231A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| DK3271347T3 (da) * | 2015-03-19 | 2022-07-18 | Mycovia Pharmaceuticals Inc | Antifungale forbindelser og fremstillingsfremgangsmåder |
| KR20180000731A (ko) | 2015-05-18 | 2018-01-03 | 비아멧 파마슈티컬즈, 인코포레이티드 | 항진균성 화합물 |
| HK1263287A1 (zh) | 2015-09-18 | 2020-03-20 | Nqp 1598, Ltd. | 抗真菌化合物和制备方法 |
| CA3005743A1 (en) | 2015-11-17 | 2017-05-26 | Dow Agrosciences Llc | 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1h-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile and processes of preparation |
| JP6963557B2 (ja) | 2015-11-17 | 2021-11-10 | コルテバ アグリサイエンス エルエルシー | ４−（（６−（２−（２，４−ジフルオロフェニル）−１，１−ジフルオロ−２−ヒドロキシ−３−（１ｈ−１，２，４−トリアゾール−１−イル）プロピル）ピリジン−３−イル）オキシ）ベンゾニトリル及び調製方法 |
| KR20180101343A (ko) | 2015-11-17 | 2018-09-12 | 다우 아그로사이언시즈 엘엘씨 | 4-((6-(2-(2,4-디플루오로페닐)-1,1-디플루오로-2-옥소에틸)피리딘-3-일)옥시)벤조니트릴 및 제조방법 |
| EP3377475A4 (en) | 2015-11-17 | 2019-04-10 | Dow Agrosciences Llc | 4 - ((6-2- (2,4-difluorophenyl) -1,1-difluoro-2-hydroxy-3- (1H-1,2,4-triazol-1-YL) PROPYL) PYRIDINE-3-YL ) OXY) BENZONITRIL AND METHOD OF PREPARING THEREOF |
| EA038421B1 (ru) | 2015-12-30 | 2021-08-26 | ВиПиЭс-3, ИНК. | Соединения, ингибирующие металлоферменты |
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