JP2018520104A5 - - Google Patents
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- JP2018520104A5 JP2018520104A5 JP2017560525A JP2017560525A JP2018520104A5 JP 2018520104 A5 JP2018520104 A5 JP 2018520104A5 JP 2017560525 A JP2017560525 A JP 2017560525A JP 2017560525 A JP2017560525 A JP 2017560525A JP 2018520104 A5 JP2018520104 A5 JP 2018520104A5
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- JP
- Japan
- Prior art keywords
- pharmaceutical composition
- composition according
- compound
- pharmaceutically acceptable
- compound according
- 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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- 150000001875 compounds Chemical class 0.000 claims description 30
- 208000031888 Mycoses Diseases 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- -1 4- (4-(((3R, 5R) -5-((1H-1,2,4-triazol-1-yl) methyl) -5- (2, 4-Difluorophenyl) tetrahydrofuran-3-yl) methoxy) -3-methylphenyl) piperazin-1-yl Chemical group 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 7
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 241001225321 Aspergillus fumigatus Species 0.000 claims description 6
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 6
- 229940091771 aspergillus fumigatus Drugs 0.000 claims description 6
- 241000228212 Aspergillus Species 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 claims description 4
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 4
- 108010020326 Caspofungin Proteins 0.000 claims description 4
- 229940121375 antifungal agent Drugs 0.000 claims description 4
- 239000003429 antifungal agent Substances 0.000 claims description 4
- JYIKNQVWKBUSNH-WVDDFWQHSA-N caspofungin Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3CC[C@H](O)[C@H]3C(=O)N[C@H](NCCN)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@H](O)CCN)=CC=C(O)C=C1 JYIKNQVWKBUSNH-WVDDFWQHSA-N 0.000 claims description 4
- 229960003034 caspofungin Drugs 0.000 claims description 4
- 229960004130 itraconazole Drugs 0.000 claims description 4
- 229960001589 posaconazole Drugs 0.000 claims description 4
- RAGOYPUPXAKGKH-XAKZXMRKSA-N posaconazole Chemical compound O=C1N([C@H]([C@H](C)O)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@H]3C[C@@](CN4N=CN=C4)(OC3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 RAGOYPUPXAKGKH-XAKZXMRKSA-N 0.000 claims description 4
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 claims description 4
- 229960004740 voriconazole Drugs 0.000 claims description 4
- 241000222122 Candida albicans Species 0.000 claims description 3
- 241001480003 Chaetothyriales Species 0.000 claims description 3
- 241000222290 Cladosporium Species 0.000 claims description 3
- 201000007336 Cryptococcosis Diseases 0.000 claims description 3
- 241000221204 Cryptococcus neoformans Species 0.000 claims description 3
- 241000223195 Fusarium graminearum Species 0.000 claims description 3
- 241000228150 Penicillium chrysogenum Species 0.000 claims description 3
- 241000235527 Rhizopus Species 0.000 claims description 3
- 241000223238 Trichophyton Species 0.000 claims description 3
- 241000222126 [Candida] glabrata Species 0.000 claims description 3
- 229940095731 candida albicans Drugs 0.000 claims description 3
- 208000032343 candida glabrata infection Diseases 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims description 2
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 2
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 2
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims description 2
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 2
- 229960003942 amphotericin b Drugs 0.000 claims description 2
- 125000004212 difluorophenyl group Chemical group 0.000 claims description 2
- 229960003765 fluvastatin Drugs 0.000 claims description 2
- 229960004844 lovastatin Drugs 0.000 claims description 2
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 2
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 229960002965 pravastatin Drugs 0.000 claims description 2
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims description 2
- PQMCFTMVQORYJC-UHFFFAOYSA-N 2-aminocyclohexan-1-ol Chemical compound NC1CCCCC1O PQMCFTMVQORYJC-UHFFFAOYSA-N 0.000 claims 1
- 241000228197 Aspergillus flavus Species 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- 0 Cc(cc(cc1)NCCNc(cc2)ccc2C(O*)=O)c1OC[C@@](C1)CO[C@@]1(C[n]1ncnc1)c(c(F)c1)ccc1F Chemical compound Cc(cc(cc1)NCCNc(cc2)ccc2C(O*)=O)c1OC[C@@](C1)CO[C@@]1(C[n]1ncnc1)c(c(F)c1)ccc1F 0.000 description 1
- 229940123934 Reductase inhibitor Drugs 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000006242 amine protecting group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15168637 | 2015-05-21 | ||
| EP15168637.5 | 2015-05-21 | ||
| PCT/GB2016/051467 WO2016185225A1 (en) | 2015-05-21 | 2016-05-20 | Antifungal 4-(4-(4-(((3r,5r)-5-((1 h -1,2,4-triazol-1 -yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)- 3-methylphenyl)piperazin-1 -yl )-n -(2-h yd roxycyc lo h exyl) b e nzam i d e, or a pharmaceutically acceptable salt thereof. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018520104A JP2018520104A (ja) | 2018-07-26 |
| JP2018520104A5 true JP2018520104A5 (OSRAM) | 2019-06-20 |
| JP6811727B2 JP6811727B2 (ja) | 2021-01-20 |
Family
ID=53267232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017560525A Active JP6811727B2 (ja) | 2015-05-21 | 2016-05-20 | 抗真菌性の４−（４−（４−（（（３ｒ，５ｒ）−５−（（１ｈ−１，２，４−トリアゾール−１−イル）メチル）−５−（２，４−ジフルオロフェニル）テトラヒドロフラン−３−イル）メトキシ）−３−メチルフェニル）ピペラジン−１−イル）−ｎ−（２−ヒドロキシシクロヘキシル）ベンズアミド、又はその医薬として許容し得る塩 |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US9969720B2 (OSRAM) |
| EP (1) | EP3298006B1 (OSRAM) |
| JP (1) | JP6811727B2 (OSRAM) |
| KR (1) | KR102653821B1 (OSRAM) |
| CN (1) | CN107635988B (OSRAM) |
| AU (1) | AU2016263669B2 (OSRAM) |
| CA (1) | CA2981945C (OSRAM) |
| DK (1) | DK3298006T3 (OSRAM) |
| EA (1) | EA032454B1 (OSRAM) |
| ES (1) | ES2790723T3 (OSRAM) |
| HU (1) | HUE048843T2 (OSRAM) |
| IL (1) | IL254943B (OSRAM) |
| MX (1) | MX379586B (OSRAM) |
| NZ (1) | NZ735783A (OSRAM) |
| SG (1) | SG11201708007VA (OSRAM) |
| WO (1) | WO2016185225A1 (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016185225A1 (en) * | 2015-05-21 | 2016-11-24 | Pulmocide Limited | Antifungal 4-(4-(4-(((3r,5r)-5-((1 h -1,2,4-triazol-1 -yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)- 3-methylphenyl)piperazin-1 -yl )-n -(2-h yd roxycyc lo h exyl) b e nzam i d e, or a pharmaceutically acceptable salt thereof. |
| CN109329288A (zh) * | 2018-11-09 | 2019-02-15 | 青岛农业大学 | 伏立康唑在制备用于防治植物病原菌的杀菌剂中的应用 |
| US11977085B1 (en) | 2023-09-05 | 2024-05-07 | Elan Ehrlich | Date rape drug detection device and method of using same |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1292472C (en) | 1985-12-03 | 1991-11-26 | Alfonsus Guilielmus Knaeps | Derivatives of ¬¬4-¬4-(4-phenyl-1-piperazinyl)- phenoxymethyl|-1,3-dioxolan-2-yl|methyl|-1h-imidazoles and 1h-1,2,4-triazoles |
| EP0318214B1 (en) | 1987-11-20 | 1994-12-14 | Schering Corporation | Tri- and tetra-substituted-oxetanes and -tetrahydrofurans and intermediates thereof |
| US5039676A (en) * | 1990-05-11 | 1991-08-13 | Schering Corporation | Tri- and tetra-substituted-oxetanes and tetrahydrofurans and intermediates thereof |
| HU225062B1 (en) * | 1993-12-21 | 2006-05-29 | Schering Corp | Tetrahydrofuran derivatives with antifungal- effect, pharmaceutical compositions containing them and process for their preparation |
| US5714490A (en) | 1993-12-21 | 1998-02-03 | Schering Corporation | Tetrahydrofuran antifungals |
| US5486625A (en) | 1994-07-08 | 1996-01-23 | Schering Corporation | Process for the preparation of chiral intermediates useful for the synthesis of antifungal agents |
| CZ59497A3 (en) | 1995-06-02 | 1997-08-13 | Schering Corp | Tetrahydrofuran derivative and pharmaceutical composition containing thereof |
| EP0957101A1 (en) * | 1998-05-14 | 1999-11-17 | Janssen Pharmaceutica N.V. | Water soluble azoles as broad-spectrum antifungals |
| EP1372394A1 (en) | 2001-04-03 | 2004-01-02 | Schering Corporation | Antifungal composition with enhanced bioavailability |
| EP1870405A1 (en) * | 2006-06-22 | 2007-12-26 | Bioprojet | Carbonylated (Aza)cyclohexanes as dopamine D3 receptor ligands |
| CN101402613B (zh) * | 2008-11-14 | 2013-07-24 | 中国人民解放军第二军医大学 | 取代酚氧烷基胺三唑醇类抗真菌化合物及其制备方法 |
| CN102234267A (zh) * | 2010-04-21 | 2011-11-09 | 中国科学院上海药物研究所 | 新型三氮唑类抗真菌化合物、其药物组合物及其制备方法和用途 |
| US9346791B2 (en) * | 2011-09-07 | 2016-05-24 | The Johns Hopkins University | Itraconazole analogs and use thereof |
| JP6669751B2 (ja) | 2014-12-05 | 2020-03-18 | プルモシデ リミテド | 抗真菌化合物 |
| WO2016185225A1 (en) * | 2015-05-21 | 2016-11-24 | Pulmocide Limited | Antifungal 4-(4-(4-(((3r,5r)-5-((1 h -1,2,4-triazol-1 -yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)- 3-methylphenyl)piperazin-1 -yl )-n -(2-h yd roxycyc lo h exyl) b e nzam i d e, or a pharmaceutically acceptable salt thereof. |
-
2016
- 2016-05-20 WO PCT/GB2016/051467 patent/WO2016185225A1/en not_active Ceased
- 2016-05-20 AU AU2016263669A patent/AU2016263669B2/en active Active
- 2016-05-20 DK DK16724958.0T patent/DK3298006T3/da active
- 2016-05-20 SG SG11201708007VA patent/SG11201708007VA/en unknown
- 2016-05-20 KR KR1020177033395A patent/KR102653821B1/ko active Active
- 2016-05-20 HU HUE16724958A patent/HUE048843T2/hu unknown
- 2016-05-20 NZ NZ735783A patent/NZ735783A/en unknown
- 2016-05-20 CN CN201680028971.4A patent/CN107635988B/zh active Active
- 2016-05-20 EA EA201792558A patent/EA032454B1/ru not_active IP Right Cessation
- 2016-05-20 ES ES16724958T patent/ES2790723T3/es active Active
- 2016-05-20 EP EP16724958.0A patent/EP3298006B1/en active Active
- 2016-05-20 JP JP2017560525A patent/JP6811727B2/ja active Active
- 2016-05-20 CA CA2981945A patent/CA2981945C/en active Active
- 2016-05-20 MX MX2017014814A patent/MX379586B/es unknown
- 2016-11-09 US US15/347,402 patent/US9969720B2/en active Active
-
2017
- 2017-10-09 IL IL254943A patent/IL254943B/en active IP Right Grant
-
2018
- 2018-05-04 US US15/971,316 patent/US10280155B2/en active Active
-
2019
- 2019-03-20 US US16/359,349 patent/US10513511B2/en active Active
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