JP2018503661A5 - - Google Patents
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- Publication number
- JP2018503661A5 JP2018503661A5 JP2017540175A JP2017540175A JP2018503661A5 JP 2018503661 A5 JP2018503661 A5 JP 2018503661A5 JP 2017540175 A JP2017540175 A JP 2017540175A JP 2017540175 A JP2017540175 A JP 2017540175A JP 2018503661 A5 JP2018503661 A5 JP 2018503661A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutically acceptable
- solvate
- stereoisomer
- acceptable salt
- alkyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 82
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 41
- 239000012453 solvate Substances 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 230000000926 neurological effect Effects 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- -1 piperidine compound Chemical class 0.000 claims description 5
- RVIIAZDTPXSBSA-INIZCTEOSA-N (2S)-2-amino-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-3-phenylpropanamide Chemical compound N[C@H](C(=O)NC=1N=NN(C=1)CC1=C(C=CC=C1F)F)CC1=CC=CC=C1 RVIIAZDTPXSBSA-INIZCTEOSA-N 0.000 claims description 4
- LNUWYMZWRDCHDJ-GFCCVEGCSA-N (3R)-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]morpholine-3-carboxamide Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)NC(=O)[C@@H]1NCCOC1 LNUWYMZWRDCHDJ-GFCCVEGCSA-N 0.000 claims description 4
- CPMYTQMQHAYCBW-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-4-pyrrolidin-1-yltriazole Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)N1CCCC1 CPMYTQMQHAYCBW-UHFFFAOYSA-N 0.000 claims description 4
- BDDGNXKWJXXPMI-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-N,N-dimethyltriazol-4-amine Chemical compound FC1=C(CN2N=NC(=C2)N(C)C)C(=CC=C1)F BDDGNXKWJXXPMI-UHFFFAOYSA-N 0.000 claims description 4
- ZKGWDRDIXBWEBX-UHFFFAOYSA-N 4-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]morpholine Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)N1CCOCC1 ZKGWDRDIXBWEBX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 201000006517 essential tremor Diseases 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- WRWGTYNZFVAKNT-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-n-methyltriazol-4-amine Chemical compound N1=NC(NC)=CN1CC1=C(F)C=CC=C1F WRWGTYNZFVAKNT-UHFFFAOYSA-N 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- GMDPTANAUWLYIS-SNVBAGLBSA-N (2R)-2-amino-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-3-hydroxypropanamide Chemical compound N[C@@H](C(=O)NC=1N=NN(C=1)CC1=C(C=CC=C1F)F)CO GMDPTANAUWLYIS-SNVBAGLBSA-N 0.000 claims description 2
- MWJUGFJHNNOBOI-LLVKDONJSA-N (2R)-2-amino-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-3-methoxypropanamide Chemical compound N[C@@H](C(=O)NC=1N=NN(C=1)CC1=C(C=CC=C1F)F)COC MWJUGFJHNNOBOI-LLVKDONJSA-N 0.000 claims description 2
- RVIIAZDTPXSBSA-MRXNPFEDSA-N (2R)-2-amino-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-3-phenylpropanamide Chemical compound N[C@@H](C(=O)NC=1N=NN(C=1)CC1=C(C=CC=C1F)F)CC1=CC=CC=C1 RVIIAZDTPXSBSA-MRXNPFEDSA-N 0.000 claims description 2
- LNUWYMZWRDCHDJ-LBPRGKRZSA-N (3S)-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]morpholine-3-carboxamide Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)NC(=O)[C@H]1NCCOC1 LNUWYMZWRDCHDJ-LBPRGKRZSA-N 0.000 claims description 2
- ZGWGCYNBPYSZSZ-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-N-ethyltriazol-4-amine Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)NCC ZGWGCYNBPYSZSZ-UHFFFAOYSA-N 0.000 claims description 2
- LGUYVJLSFSVQCS-UHFFFAOYSA-N 1-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]pyrrolidin-2-one Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)N1C(CCC1)=O LGUYVJLSFSVQCS-UHFFFAOYSA-N 0.000 claims description 2
- KYKWHQKFTYMZPB-UHFFFAOYSA-N 1-benzyl-N,N-dimethyltriazol-4-amine Chemical compound C(C1=CC=CC=C1)N1N=NC(=C1)N(C)C KYKWHQKFTYMZPB-UHFFFAOYSA-N 0.000 claims description 2
- NNOBBZLWKCXSBK-UHFFFAOYSA-N 2-[[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]amino]ethanol Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)NCCO NNOBBZLWKCXSBK-UHFFFAOYSA-N 0.000 claims description 2
- NRNXAAXFDBUNIO-UHFFFAOYSA-N 3-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-1,3-oxazolidin-2-one Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)N1C(OCC1)=O NRNXAAXFDBUNIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- OMFJOFLCNIPYCO-UHFFFAOYSA-N N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-3-pyridin-3-ylpropanamide Chemical compound FC1=C(CN2N=NC(=C2)NC(CCC=2C=NC=CC=2)=O)C(=CC=C1)F OMFJOFLCNIPYCO-UHFFFAOYSA-N 0.000 claims description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 208000005809 status epilepticus Diseases 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 5
- 0 *N(*)c1c[n](Cc2ccccc2)nn1 Chemical compound *N(*)c1c[n](Cc2ccccc2)nn1 0.000 description 1
- ZUASMCSOQJBASC-UHFFFAOYSA-N 1-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]imidazolidin-2-one Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)N1C(NCC1)=O ZUASMCSOQJBASC-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562110415P | 2015-01-30 | 2015-01-30 | |
| US62/110,415 | 2015-01-30 | ||
| US201562259314P | 2015-11-24 | 2015-11-24 | |
| US62/259,314 | 2015-11-24 | ||
| PCT/US2016/015740 WO2016123533A1 (en) | 2015-01-30 | 2016-01-29 | Substituted triazoles and methods relating thereto |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018503661A JP2018503661A (ja) | 2018-02-08 |
| JP2018503661A5 true JP2018503661A5 (OSRAM) | 2019-03-14 |
| JP6728198B2 JP6728198B2 (ja) | 2020-07-22 |
Family
ID=55305123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017540175A Active JP6728198B2 (ja) | 2015-01-30 | 2016-01-29 | 置換トリアゾールおよびそれに関する方法 |
Country Status (22)
| Country | Link |
|---|---|
| US (4) | US9718789B2 (OSRAM) |
| EP (1) | EP3250563B1 (OSRAM) |
| JP (1) | JP6728198B2 (OSRAM) |
| KR (1) | KR102575601B1 (OSRAM) |
| CN (1) | CN107406420B (OSRAM) |
| AU (1) | AU2016211292B2 (OSRAM) |
| BR (1) | BR112017016488A2 (OSRAM) |
| CA (1) | CA2975474C (OSRAM) |
| CY (1) | CY1125082T1 (OSRAM) |
| DK (1) | DK3250563T3 (OSRAM) |
| ES (1) | ES2905878T3 (OSRAM) |
| HR (1) | HRP20220327T1 (OSRAM) |
| HU (1) | HUE058156T2 (OSRAM) |
| IL (1) | IL253705B (OSRAM) |
| LT (1) | LT3250563T (OSRAM) |
| MX (1) | MX378932B (OSRAM) |
| PL (1) | PL3250563T3 (OSRAM) |
| PT (1) | PT3250563T (OSRAM) |
| RS (1) | RS62862B1 (OSRAM) |
| RU (1) | RU2718049C2 (OSRAM) |
| SI (1) | SI3250563T1 (OSRAM) |
| WO (1) | WO2016123533A1 (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA40281B1 (fr) | 2014-06-03 | 2018-11-30 | Idorsia Pharmaceuticals Ltd | Composés de pyrazole et leur utilisation en tant qu' agents de blocage des canaux calciques de type t |
| WO2016041892A1 (en) | 2014-09-15 | 2016-03-24 | Actelion Pharmaceuticals Ltd | Triazole compounds as t-type calcium channel blockers |
| CN107406420B (zh) | 2015-01-30 | 2020-11-06 | 纽罗克里生物科学有限公司 | 取代的三唑及与其相关的方法 |
| LT3554490T (lt) | 2016-12-16 | 2022-04-25 | Idorsia Pharmaceuticals Ltd | Farmacinis derinys, apimantis t tipo kalcio kanalo blokatorių |
| CA3050348A1 (en) | 2017-02-06 | 2018-08-09 | Idorsia Pharmaceuticals Ltd | A novel process for the synthesis of 1-aryl-1-trifluoromethylcyclopropanes |
| KR102298546B1 (ko) * | 2018-10-18 | 2021-09-08 | 에이치케이이노엔 주식회사 | 신규한 n-(이소프로필-트리아졸릴)피리디닐)-헤테로아릴-카르복사미드 유도체 및 이의 용도 |
| CN110669017B (zh) * | 2019-10-11 | 2023-08-04 | 成都麻沸散医药科技有限公司 | 多取代三唑甲酸酯类衍生物及其用途 |
| CN115974799B (zh) * | 2021-10-14 | 2024-08-13 | 成都百裕制药股份有限公司 | 氨基甲酸酯取代的醇衍生物及其在医药上的应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL50699A0 (en) * | 1975-10-28 | 1976-12-31 | Ici America Inc | Triazole derivatives |
| TW513301B (en) * | 1999-03-01 | 2002-12-11 | Novartis Ag | Pharmaceutical composition for treatment of neuropathic pain and affective and attention disorders |
| HRP20050053A2 (en) * | 2002-09-19 | 2005-04-30 | Solvay Pharmaceuticals B.V. | 1 h-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-cb1 receptor ligands |
| EP1829867A1 (en) * | 2006-03-03 | 2007-09-05 | Laboratorios Del Dr. Esteve, S.A. | Imidazole compounds having pharmaceutical activity towards the sigma receptor |
| EP1921073A1 (en) * | 2006-11-10 | 2008-05-14 | Laboratorios del Dr. Esteve S.A. | 1,2,4-Triazole derivatives as sigma receptor inhibitors |
| EP1921071A1 (en) * | 2006-11-10 | 2008-05-14 | Laboratorios del Dr. Esteve S.A. | 1,2,3- triazole derivatives as sigma receptor inhibitors |
| GB0722077D0 (en) | 2007-11-09 | 2007-12-19 | Smithkline Beecham Corp | Compounds |
| US8742097B2 (en) | 2010-11-09 | 2014-06-03 | Hoffmann-La Roche Inc. | Triazole compounds I |
| EP2752411A1 (en) * | 2013-01-07 | 2014-07-09 | Laboratorios Del Dr. Esteve, S.A. | 1,2,3-triazole-4-amine derivatives for the treatment of sigma receptor related diseases and disorders |
| CN107406420B (zh) | 2015-01-30 | 2020-11-06 | 纽罗克里生物科学有限公司 | 取代的三唑及与其相关的方法 |
-
2016
- 2016-01-29 CN CN201680016876.2A patent/CN107406420B/zh active Active
- 2016-01-29 US US15/010,925 patent/US9718789B2/en active Active
- 2016-01-29 MX MX2017009824A patent/MX378932B/es unknown
- 2016-01-29 EP EP16703250.7A patent/EP3250563B1/en active Active
- 2016-01-29 CA CA2975474A patent/CA2975474C/en active Active
- 2016-01-29 RS RS20220093A patent/RS62862B1/sr unknown
- 2016-01-29 HU HUE16703250A patent/HUE058156T2/hu unknown
- 2016-01-29 LT LTEPPCT/US2016/015740T patent/LT3250563T/lt unknown
- 2016-01-29 HR HRP20220327TT patent/HRP20220327T1/hr unknown
- 2016-01-29 ES ES16703250T patent/ES2905878T3/es active Active
- 2016-01-29 BR BR112017016488A patent/BR112017016488A2/pt not_active Application Discontinuation
- 2016-01-29 DK DK16703250.7T patent/DK3250563T3/da active
- 2016-01-29 RU RU2017130474A patent/RU2718049C2/ru active
- 2016-01-29 AU AU2016211292A patent/AU2016211292B2/en active Active
- 2016-01-29 PL PL16703250T patent/PL3250563T3/pl unknown
- 2016-01-29 SI SI201631489T patent/SI3250563T1/sl unknown
- 2016-01-29 KR KR1020177023771A patent/KR102575601B1/ko active Active
- 2016-01-29 WO PCT/US2016/015740 patent/WO2016123533A1/en not_active Ceased
- 2016-01-29 JP JP2017540175A patent/JP6728198B2/ja active Active
- 2016-01-29 PT PT167032507T patent/PT3250563T/pt unknown
-
2017
- 2017-06-22 US US15/630,225 patent/US10138214B2/en active Active
- 2017-07-27 IL IL253705A patent/IL253705B/en active IP Right Grant
-
2018
- 2018-10-29 US US16/173,025 patent/US10738017B2/en active Active
-
2020
- 2020-06-04 US US16/892,718 patent/US11021449B2/en active Active
-
2022
- 2022-03-16 CY CY20221100210T patent/CY1125082T1/el unknown
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