JP2019501877A5 - - Google Patents
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- Publication number
- JP2019501877A5 JP2019501877A5 JP2018526135A JP2018526135A JP2019501877A5 JP 2019501877 A5 JP2019501877 A5 JP 2019501877A5 JP 2018526135 A JP2018526135 A JP 2018526135A JP 2018526135 A JP2018526135 A JP 2018526135A JP 2019501877 A5 JP2019501877 A5 JP 2019501877A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- substituted
- heteroaryl
- amino
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 229940002612 prodrug Drugs 0.000 claims description 32
- 239000000651 prodrug Substances 0.000 claims description 32
- 229910052751 metal Inorganic materials 0.000 claims description 28
- 239000002184 metal Substances 0.000 claims description 28
- FTALBRSUTCGOEG-UHFFFAOYSA-N Riluzole Chemical group C1=C(OC(F)(F)F)C=C2SC(N)=NC2=C1 FTALBRSUTCGOEG-UHFFFAOYSA-N 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 229960004181 riluzole Drugs 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 150000003141 primary amines Chemical class 0.000 claims description 12
- 150000003335 secondary amines Chemical class 0.000 claims description 12
- 150000003512 tertiary amines Chemical class 0.000 claims description 12
- 229910052744 lithium Inorganic materials 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 229910052709 silver Inorganic materials 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 150000001413 amino acids Chemical class 0.000 claims description 9
- 150000003863 ammonium salts Chemical class 0.000 claims description 9
- 229910052791 calcium Inorganic materials 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 229910052749 magnesium Inorganic materials 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 229910052725 zinc Inorganic materials 0.000 claims description 9
- 230000002194 synthesizing effect Effects 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- -1 cyano, nitro, mercapto Chemical class 0.000 claims 24
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 10
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 125000001769 aryl amino group Chemical group 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 239000004202 carbamide Substances 0.000 claims 5
- 235000013877 carbamide Nutrition 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims 5
- 125000004986 diarylamino group Chemical group 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 229910052740 iodine Inorganic materials 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 5
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims 5
- 125000000464 thioxo group Chemical group S=* 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 239000011734 sodium Substances 0.000 description 4
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562257533P | 2015-11-19 | 2015-11-19 | |
| US62/257,533 | 2015-11-19 | ||
| PCT/US2016/062400 WO2017087594A1 (en) | 2015-11-19 | 2016-11-17 | Amine prodrugs of pharmaceutical compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019501877A JP2019501877A (ja) | 2019-01-24 |
| JP2019501877A5 true JP2019501877A5 (enExample) | 2019-12-26 |
| JP7110094B2 JP7110094B2 (ja) | 2022-08-01 |
Family
ID=58717793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018526135A Active JP7110094B2 (ja) | 2015-11-19 | 2016-11-17 | 医薬化合物のアミンプロドラッグ |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US20180318268A1 (enExample) |
| EP (1) | EP3377111B1 (enExample) |
| JP (1) | JP7110094B2 (enExample) |
| KR (1) | KR20180084049A (enExample) |
| ES (1) | ES2969792T3 (enExample) |
| IL (1) | IL259394B (enExample) |
| SG (2) | SG11201803645PA (enExample) |
| WO (1) | WO2017087594A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12295942B2 (en) | 2015-03-03 | 2025-05-13 | Biohaven Therapeutics Ltd. | Riluzole prodrugs and their use |
| DK3265448T3 (da) | 2015-03-03 | 2022-03-28 | Biohaven Therapeutics Ltd | Riluzol-prodrugs og anvendelse deraf |
| US12029731B2 (en) | 2016-08-10 | 2024-07-09 | Biohaven Therapeutics Ltd. | Acyl benzo[d]thiazol-2-amine and their methods of use |
| US20250049748A1 (en) * | 2021-12-16 | 2025-02-13 | Terran Biosciences Inc. | Analogs of 4-bromo-2,5-dimethoxyphenethylamine |
| WO2023141636A1 (en) * | 2022-01-24 | 2023-07-27 | Terran Biosciences Inc. | Prodrugs of 2-bromo-lsd (2-bromolysergic acid diethylamide) |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW354293B (en) * | 1995-06-06 | 1999-03-11 | Bristol Myers Squibb Co | Prodrugs of paclitaxel derivatives |
| GB2362646A (en) | 2000-05-26 | 2001-11-28 | Warner Lambert Co | Cyclic amino acid derivatives useful as pharmaceutical agents |
| JP2006510618A (ja) | 2002-11-18 | 2006-03-30 | ヤウポン セラピューティクス，インコーポレーテッド | ノルケタミンおよびケタミン／ノルケタミンプロドラッグの鎮痛的使用 |
| US20040176430A1 (en) * | 2002-11-21 | 2004-09-09 | Jeffrey Sterling | Propargyl-trifluoromethoxy-amino-benzothiazole derivatives |
| AU2003293423A1 (en) | 2002-12-06 | 2004-06-30 | Xenoport, Inc. | Carbidopa prodrugs and uses thereof |
| AR051475A1 (es) | 2004-11-05 | 2007-01-17 | Merck & Co Inc | Procedimiento para acido{3- [2 (r) -[(1r) - 1-[ 3,5- bis( trifluorometil)- fenil] etoxi] -3 (s) - (4- fluorfenil) morfolin -4- il]metil -5-oxo-4,5-dihidro- [1,2,4]-triazol-1-il} fosfonico |
| EP1915053A2 (en) | 2005-08-12 | 2008-04-30 | Merck & Co., Inc. | Novel 2'-c-methyl and 4'-c-methyl nucleoside derivatives |
| MX2010002932A (es) | 2007-09-17 | 2010-05-27 | Enanta Pharm Inc | Macrolidos de biarilo con puente en 6, 11. |
| US8106209B2 (en) | 2008-06-06 | 2012-01-31 | Achillion Pharmaceuticals, Inc. | Substituted aminothiazole prodrugs of compounds with anti-HCV activity |
| EP2525829A1 (en) * | 2010-01-22 | 2012-11-28 | Ascendis Pharma A/S | Dipeptide-based prodrug linkers for aromatic amine-containing drugs |
| WO2011109767A2 (en) * | 2010-03-04 | 2011-09-09 | University Of Notre Dame Du Lac | Gelatinase inhibitors and prodrugs |
| WO2013088255A1 (en) | 2011-12-15 | 2013-06-20 | Alkermes Pharma Ireland Limited | Prodrugs of secondary amine compounds |
| US9725427B2 (en) | 2012-03-16 | 2017-08-08 | Biohaven Pharmaceutical Holding Company Limited | Prodrugs of riluzole and their method of use |
| US9434704B2 (en) | 2012-05-08 | 2016-09-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological degenerative disorders |
| PT2858987T (pt) | 2012-06-11 | 2018-07-04 | Bristol Myers Squibb Co | Profármacos de ácido fosforamídico de 5-[5-fenil-4-(piridin-2-ilmetilamino)quinazolin -2-il]piridina-3-sulfonamida |
| WO2014011695A2 (en) * | 2012-07-09 | 2014-01-16 | Onyx Therapeutics, Inc. | Prodrugs of peptide epoxy ketone protease inhibitors |
-
2016
- 2016-11-17 KR KR1020187013838A patent/KR20180084049A/ko not_active Ceased
- 2016-11-17 WO PCT/US2016/062400 patent/WO2017087594A1/en not_active Ceased
- 2016-11-17 US US15/775,897 patent/US20180318268A1/en not_active Abandoned
- 2016-11-17 SG SG11201803645PA patent/SG11201803645PA/en unknown
- 2016-11-17 JP JP2018526135A patent/JP7110094B2/ja active Active
- 2016-11-17 ES ES16867091T patent/ES2969792T3/es active Active
- 2016-11-17 EP EP16867091.7A patent/EP3377111B1/en active Active
- 2016-11-17 SG SG10202112588PA patent/SG10202112588PA/en unknown
-
2018
- 2018-05-16 IL IL259394A patent/IL259394B/en unknown
-
2019
- 2019-08-19 US US16/544,166 patent/US11083711B2/en active Active
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