JP2019502755A5 - - Google Patents
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- Publication number
- JP2019502755A5 JP2019502755A5 JP2018553846A JP2018553846A JP2019502755A5 JP 2019502755 A5 JP2019502755 A5 JP 2019502755A5 JP 2018553846 A JP2018553846 A JP 2018553846A JP 2018553846 A JP2018553846 A JP 2018553846A JP 2019502755 A5 JP2019502755 A5 JP 2019502755A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyridin
- difluoro
- tetrazol
- piperazin
- 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
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 69
- -1 NH 2 Chemical group 0.000 claims 43
- 150000001875 compounds Chemical class 0.000 claims 42
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 42
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 35
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 31
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 21
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 201000010099 disease Diseases 0.000 claims 12
- 125000001153 fluoro group Chemical group F* 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 208000035475 disorder Diseases 0.000 claims 9
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 229940124597 therapeutic agent Drugs 0.000 claims 5
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 claims 4
- 239000002184 metal Substances 0.000 claims 4
- 241000222122 Candida albicans Species 0.000 claims 3
- 102000004190 Enzymes Human genes 0.000 claims 3
- 108090000790 Enzymes Proteins 0.000 claims 3
- DIHPVRJYXAIEQR-ZSXSBBPPSA-N FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C=1C=NC(=CC=1)C(C(F)(F)F)O)(F)F)(CN1N=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C=1C=NC(=CC=1)C(C(F)(F)F)O)(F)F)(CN1N=NN=C1)O DIHPVRJYXAIEQR-ZSXSBBPPSA-N 0.000 claims 3
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- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methyl-1-butanol Substances CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
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- CHCBEOJABAZIOY-ZSXSBBPPSA-N FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC(=NC=C1)C(C(F)(F)F)O)(F)F)(CN1N=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC(=NC=C1)C(C(F)(F)F)O)(F)F)(CN1N=NN=C1)O CHCBEOJABAZIOY-ZSXSBBPPSA-N 0.000 claims 2
- VKOOJCSMWOOQHZ-HKBQPEDESA-N FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC2=C(NC(=N2)C(F)(F)F)C=C1)(F)F)(CN1N=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC2=C(NC(=N2)C(F)(F)F)C=C1)(F)F)(CN1N=NN=C1)O VKOOJCSMWOOQHZ-HKBQPEDESA-N 0.000 claims 2
- HAWNZENDCHYEQZ-JYUUXGOASA-N FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)C(C(F)(F)F)O)(F)F)(CN1C=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)C(C(F)(F)F)O)(F)F)(CN1C=NN=C1)O HAWNZENDCHYEQZ-JYUUXGOASA-N 0.000 claims 2
- CHPQEFIJCCDEFH-FLDQDSGZSA-N FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)C(C(F)(F)F)O)(F)F)(CN1N=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)C(C(F)(F)F)O)(F)F)(CN1N=NN=C1)O CHPQEFIJCCDEFH-FLDQDSGZSA-N 0.000 claims 2
- BIFXOHAXTPHDQX-XIFFEERXSA-N FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)C(C)(C)O)(F)F)(CN1N=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)C(C)(C)O)(F)F)(CN1N=NN=C1)O BIFXOHAXTPHDQX-XIFFEERXSA-N 0.000 claims 2
- NIGBDUZMVMRPER-PMERELPUSA-N FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)F)(F)F)(CN1N=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(C1=NC=C(C=C1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)F)(F)F)(CN1N=NN=C1)O NIGBDUZMVMRPER-PMERELPUSA-N 0.000 claims 2
- IACOWBALBATJAE-YTTGMZPUSA-N FC1=C(C=CC(=C1)F)[C@](C(F)(F)C1=CC=C(C=N1)C1=CC=C(C=C1)N1CCC(CC1)C1=CC=C(C#N)C=C1)(CN1N=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(F)(F)C1=CC=C(C=N1)C1=CC=C(C=C1)N1CCC(CC1)C1=CC=C(C#N)C=C1)(CN1N=NN=C1)O IACOWBALBATJAE-YTTGMZPUSA-N 0.000 claims 2
- YTAFWBOGMBEQFX-HKBQPEDESA-N FC1=C(C=CC(=C1)F)[C@](C(F)(F)C1=CC=C(C=N1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC(=C(C#N)C=C1)F)(CN1N=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(F)(F)C1=CC=C(C=N1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC(=C(C#N)C=C1)F)(CN1N=NN=C1)O YTAFWBOGMBEQFX-HKBQPEDESA-N 0.000 claims 2
- QKWUMLTVHKNXNQ-HKBQPEDESA-N FC1=C(C=CC(=C1)F)[C@](C(F)(F)C1=CC=C(C=N1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C#N)C=C1)(CN1N=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(F)(F)C1=CC=C(C=N1)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C#N)C=C1)(CN1N=NN=C1)O QKWUMLTVHKNXNQ-HKBQPEDESA-N 0.000 claims 2
- PWJHESUJMQFMLX-PMERELPUSA-N FC1=C(C=CC(=C1)F)[C@](C(F)(F)C1=CC=C(C=N1)C1=CC=C(C=C1)N1CCN(CC1)C1=NC=C(C#N)C=C1)(CN1N=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(F)(F)C1=CC=C(C=N1)C1=CC=C(C=C1)N1CCN(CC1)C1=NC=C(C#N)C=C1)(CN1N=NN=C1)O PWJHESUJMQFMLX-PMERELPUSA-N 0.000 claims 2
- MOTYPNJIEOKQIP-PMERELPUSA-N FC1=C(C=CC(=C1)F)[C@](C(F)(F)C1=CC=C(C=N1)C1=CC=C(C=C1)N1CCN(CC1)C=1C=CC(=NC=1)C#N)(CN1N=NN=C1)O Chemical compound FC1=C(C=CC(=C1)F)[C@](C(F)(F)C1=CC=C(C=N1)C1=CC=C(C=C1)N1CCN(CC1)C=1C=CC(=NC=1)C#N)(CN1N=NN=C1)O MOTYPNJIEOKQIP-PMERELPUSA-N 0.000 claims 2
- 206010017533 Fungal infection Diseases 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- 241000228143 Penicillium Species 0.000 claims 2
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- 208000002474 Tinea Diseases 0.000 claims 2
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- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
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- 229940127089 cytotoxic agent Drugs 0.000 claims 2
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- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 229910052742 iron Inorganic materials 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 244000005700 microbiome Species 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 claims 1
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 claims 1
- CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 claims 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims 1
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 claims 1
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 claims 1
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 claims 1
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| WO2015143184A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| 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 |
| JP6606508B2 (ja) | 2014-03-19 | 2019-11-13 | マイコヴィア ファーマシューティカルズ，インコーポレイテッド | 抗真菌化合物の調製方法 |
| 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 |
| CN109970629B (zh) | 2014-03-19 | 2023-04-11 | 迈科维亚医药公司 | 抗真菌化合物的制备方法 |
| AU2015231275B2 (en) | 2014-03-19 | 2019-03-07 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| JP2017509646A (ja) | 2014-03-19 | 2017-04-06 | 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 |
| AU2015231216B2 (en) | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| CA2942936A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| CN108289457B (zh) | 2015-09-18 | 2021-08-06 | 迈科维亚医药公司 | 抗真菌化合物制备方法 |
| WO2019182743A1 (en) * | 2018-03-20 | 2019-09-26 | Innocrin Pharmaceuticals, Inc. | Compositions for the treatment of brain tumors |
| US12357615B2 (en) | 2018-10-11 | 2025-07-15 | Kembi Therapeutics Pty Ltd | Compositions for the treatment of brain tumors |
| WO2022216680A1 (en) | 2021-04-05 | 2022-10-13 | Halia Therapeutics, Inc. | Nek7 inhibitors |
| CN113444131B (zh) * | 2021-06-24 | 2022-10-21 | 鲁东大学 | N-乙酰氨基葡萄糖类化合物及其制备方法和应用 |
| US20250270193A1 (en) * | 2021-10-20 | 2025-08-28 | Ohio State Innovation Foundation | Arylimidamides for use in treatment of cancers |
| CN115466227B (zh) * | 2022-06-30 | 2024-07-19 | 杭州国瑞生物科技有限公司 | 一种3-(氯甲基)-1-甲基-1h-1,2,4-三唑盐酸盐的制备方法 |
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| US5312325A (en) | 1987-05-28 | 1994-05-17 | Drug Delivery Systems Inc | Pulsating transdermal drug delivery system |
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| US5008110A (en) | 1988-11-10 | 1991-04-16 | The Procter & Gamble Company | Storage-stable transdermal patch |
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| IL114193A (en) | 1994-06-20 | 2000-02-29 | Teva Pharma | Ophthalmic pharmaceutical compositions based on sodium alginate |
| ES2094688B1 (es) | 1994-08-08 | 1997-08-01 | Cusi Lab | Manoemulsion del tipo de aceite en agua, util como vehiculo oftalmico y procedimiento para su preparacion. |
| IT1283911B1 (it) | 1996-02-05 | 1998-05-07 | Farmigea Spa | Soluzioni oftalmiche viscosizzate con polisaccaridi della gomma di tamarindo |
| US5800807A (en) | 1997-01-29 | 1998-09-01 | Bausch & Lomb Incorporated | Ophthalmic compositions including glycerin and propylene glycol |
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