JP2018108997A5 - - Google Patents
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- Publication number
- JP2018108997A5 JP2018108997A5 JP2018001678A JP2018001678A JP2018108997A5 JP 2018108997 A5 JP2018108997 A5 JP 2018108997A5 JP 2018001678 A JP2018001678 A JP 2018001678A JP 2018001678 A JP2018001678 A JP 2018001678A JP 2018108997 A5 JP2018108997 A5 JP 2018108997A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- chloro
- pharmaceutically acceptable
- prodrug
- acceptable salt
- 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
- -1 amino, hydroxyl Chemical group 0.000 claims description 175
- 150000003839 salts Chemical class 0.000 claims description 92
- 239000000651 prodrug Substances 0.000 claims description 88
- 229940002612 prodrug Drugs 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 86
- 239000001257 hydrogen Substances 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 150000002431 hydrogen Chemical group 0.000 claims description 33
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 2
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 102100037652 Kynurenine 3-monooxygenase Human genes 0.000 claims description 2
- 108010033242 Kynurenine 3-monooxygenase Proteins 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 2
- 230000000626 neurodegenerative effect Effects 0.000 claims description 2
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- INFKWNUZDNIJDQ-KYDCKOQZSA-N CC(Cc1cc(C([C@@H](C2)[C@H]2C(O)=O)=O)c2)COc1c2Cl Chemical compound CC(Cc1cc(C([C@@H](C2)[C@H]2C(O)=O)=O)c2)COc1c2Cl INFKWNUZDNIJDQ-KYDCKOQZSA-N 0.000 description 1
- BPQDTVIIWUGOJZ-VJCKSVEBSA-N CC(Cc1cc(C([C@@H](C2)[C@H]2C(O)=O)=O)c2)Oc1c2Cl Chemical compound CC(Cc1cc(C([C@@H](C2)[C@H]2C(O)=O)=O)c2)Oc1c2Cl BPQDTVIIWUGOJZ-VJCKSVEBSA-N 0.000 description 1
- KSIQRBJGSITOLR-TWELXNIESA-N CC(Oc1cc(C([C@@H](C2)[C@H]2C(O)=O)=O)c2)Oc1c2Cl Chemical compound CC(Oc1cc(C([C@@H](C2)[C@H]2C(O)=O)=O)c2)Oc1c2Cl KSIQRBJGSITOLR-TWELXNIESA-N 0.000 description 1
- CMTXOMMPDQBUPO-YUMQZZPRSA-N OC([C@@H](C1)[C@H]1C(c1cc(Cl)c2OCCOc2c1)=O)=O Chemical compound OC([C@@H](C1)[C@H]1C(c1cc(Cl)c2OCCOc2c1)=O)=O CMTXOMMPDQBUPO-YUMQZZPRSA-N 0.000 description 1
- JWUSMOIXSPWZAO-BQBZGAKWSA-N OC([C@@H](C1)[C@H]1C(c1cc(Cl)c2OCOc2c1)=O)=O Chemical compound OC([C@@H](C1)[C@H]1C(c1cc(Cl)c2OCOc2c1)=O)=O JWUSMOIXSPWZAO-BQBZGAKWSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261620953P | 2012-04-05 | 2012-04-05 | |
| US61/620,953 | 2012-04-05 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015504581A Division JP6275690B2 (ja) | 2012-04-05 | 2013-03-13 | キヌレニン−３−モノオキシゲナーゼインヒビターおよびその医薬組成物ならびにこれらの使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018108997A JP2018108997A (ja) | 2018-07-12 |
| JP2018108997A5 true JP2018108997A5 (enExample) | 2018-12-20 |
| JP6622824B2 JP6622824B2 (ja) | 2019-12-18 |
Family
ID=49300915
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015504581A Active JP6275690B2 (ja) | 2012-04-05 | 2013-03-13 | キヌレニン−３−モノオキシゲナーゼインヒビターおよびその医薬組成物ならびにこれらの使用方法 |
| JP2018001678A Active JP6622824B2 (ja) | 2012-04-05 | 2018-01-10 | キヌレニン−３−モノオキシゲナーゼインヒビターおよびその医薬組成物ならびにこれらの使用方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015504581A Active JP6275690B2 (ja) | 2012-04-05 | 2013-03-13 | キヌレニン−３−モノオキシゲナーゼインヒビターおよびその医薬組成物ならびにこれらの使用方法 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US9822058B2 (enExample) |
| EP (2) | EP2833879A4 (enExample) |
| JP (2) | JP6275690B2 (enExample) |
| KR (1) | KR20150000882A (enExample) |
| CN (1) | CN104244939A (enExample) |
| AR (1) | AR090601A1 (enExample) |
| AU (1) | AU2013243898A1 (enExample) |
| BR (1) | BR112014024693A2 (enExample) |
| CA (1) | CA2868321A1 (enExample) |
| EA (1) | EA201491606A1 (enExample) |
| ES (1) | ES2972419T3 (enExample) |
| HK (1) | HK1206264A1 (enExample) |
| IL (1) | IL234884A0 (enExample) |
| MX (1) | MX2014011946A (enExample) |
| PH (1) | PH12014502218A1 (enExample) |
| SG (1) | SG11201406311UA (enExample) |
| TW (1) | TW201402537A (enExample) |
| WO (1) | WO2013151707A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2750677T (pt) | 2011-08-30 | 2017-07-03 | Chdi Foundation Inc | Inibidores de quinurenina-3-monooxigenase, composições farmacêuticas e métodos de utilização dos mesmos |
| WO2013033068A1 (en) | 2011-08-30 | 2013-03-07 | Stephen Martin Courtney | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| US9822058B2 (en) | 2012-04-05 | 2017-11-21 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| WO2015047982A2 (en) * | 2013-09-26 | 2015-04-02 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| US9938252B2 (en) | 2013-09-26 | 2018-04-10 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| GB201322512D0 (en) * | 2013-12-19 | 2014-02-05 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| JP2017520610A (ja) | 2014-07-17 | 2017-07-27 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | Ｈｉｖ関連障害を治療するための方法及び組成物 |
| WO2016027757A1 (ja) * | 2014-08-18 | 2016-02-25 | 国立大学法人大阪大学 | 新規２－アミノベンゾイル誘導体 |
| GB201507753D0 (en) * | 2015-05-06 | 2015-06-17 | Biolipox Ab | New compounds and uses |
| EP3291810B1 (en) * | 2015-05-07 | 2022-08-10 | CHDI Foundation, Inc. | Histone deacetylase inhibitors and compositions and methods of use thereof |
| EP3291809B1 (en) | 2015-05-07 | 2021-08-25 | CHDI Foundation, Inc. | Histone deacetylase inhibitors and compositions and methods of use thereof |
| GB201508857D0 (en) * | 2015-05-22 | 2015-07-01 | Glaxosmithkline Ip Dev Ltd | Compounds |
| GB201508864D0 (en) * | 2015-05-22 | 2015-07-01 | Glaxosmithkline Ip Dev Ltd | Compounds |
| MX2019004181A (es) | 2016-10-13 | 2019-10-30 | Juno Therapeutics Inc | Métodos y composiciones de inmunoterapia que implican moduladores de la ruta metabólica de triptófano. |
| US11911376B2 (en) | 2020-03-30 | 2024-02-27 | The Regents Of The University Of Colorado | Methods for preventing and treating retinal damage |
| US12029718B2 (en) | 2021-11-09 | 2024-07-09 | Cct Sciences, Llc | Process for production of essentially pure delta-9-tetrahydrocannabinol |
| CN113816887A (zh) * | 2021-08-31 | 2021-12-21 | 华中科技大学 | 一种氮杂环丙烷类化合物及其制备方法 |
| CN119143707B (zh) * | 2024-11-20 | 2025-01-28 | 山东第一医科大学(山东省医学科学院) | 一种螺旋-2(3h)-呋喃酮分子及其制备方法和应用 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US228550A (en) * | 1880-06-08 | Peters | ||
| DE3124699A1 (de) | 1981-06-24 | 1983-01-13 | Basf Ag, 6700 Ludwigshafen | Neue 2-aryl-3,4-diaza-bicyclo(4.n.0.)alken-(2)-one-(5),verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3535170A1 (de) | 1985-10-02 | 1987-04-16 | Basf Ag | Verwendung von 2-aryl-3,4-diaza-bicyclo(4.n.0)alken-(2)-onen-(5) zur behandlung der herzinsuffizienz |
| GB8712466D0 (en) | 1987-05-27 | 1987-07-01 | Roussel Lab Ltd | Chemical compounds |
| GB8908846D0 (en) | 1989-04-19 | 1989-06-07 | Roussel Lab Ltd | Chemical compounds |
| US6334997B1 (en) | 1994-03-25 | 2002-01-01 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| AU707748B2 (en) | 1994-03-25 | 1999-07-22 | Isotechnika Inc. | Enhancement of the efficacy of drugs by deuteration |
| GB9522617D0 (en) | 1995-11-03 | 1996-01-03 | Pharmacia Spa | 4-Phenyl-4-oxo-butenoic acid derivatives with kynurenine-3-hydroxylase inhibiting activity |
| GB9522615D0 (en) | 1995-11-03 | 1996-01-03 | Pharmacia Spa | 4-Phenyl-4-oxo-butanoic acid derivatives with kynurenine-3-hydroxylase inhibiting activity |
| GB9705031D0 (en) * | 1997-03-11 | 1997-04-30 | Pharmacia & Upjohn Spa | 2-substituted benzoyl-cycloalkyl-1-carboxylic acid derivatives |
| GB9714303D0 (en) * | 1997-07-07 | 1997-09-10 | Pharmacia & Upjohn Spa | 5-(3-phenyl-3-oxo-propyl)-1H-tetrazole derivatives |
| DE19952147A1 (de) * | 1999-10-29 | 2001-05-03 | Boehringer Ingelheim Pharma | Neue Cyclopropane, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US6777437B2 (en) * | 2001-03-29 | 2004-08-17 | Bristol-Myers Squibb Company | Cyclopropylindole derivatives as selective serotonin reuptake inhibitors |
| US20040077616A1 (en) | 2002-10-22 | 2004-04-22 | Bennani Youssef L. | Spirocyclopropyl amides and acids and their therapeutic applications |
| EP1424333A1 (en) * | 2002-11-28 | 2004-06-02 | Newron Pharmaceuticals S.p.A. | Halothenoyl-cyclopropane-1-carboxylic acid derivatives |
| CA2524125A1 (en) | 2003-04-29 | 2004-11-11 | Oscient Pharmaceuticals | Antibiotic tetrahydro-.beta.-carboline derivatives |
| EP1475385A1 (en) | 2003-05-05 | 2004-11-10 | Newron Pharmaceuticals S.p.A. | Glycoside derivatives of 2-(3,4-dichlorobenzoyl)-cycopropane-1-carboxylic acid |
| RU2006123559A (ru) | 2003-12-04 | 2008-01-10 | Уайт (Us) | Биарилсульфонамиды в качестве ммр-ингибиторов |
| ITMI20041626A1 (it) | 2004-08-06 | 2004-11-06 | Roberto Pellicciari | Inibitori della chinurenina-ammino-trasferasi |
| JPWO2006077901A1 (ja) | 2005-01-20 | 2008-06-19 | 塩野義製薬株式会社 | Ｃｔｇｆ発現阻害剤 |
| WO2009034029A2 (de) | 2007-09-07 | 2009-03-19 | Boehringer Ingelheim International Gmbh | 1-substituierte 4 -heterocyclylpiperidine als cgrp antagonisten |
| CA2710462C (en) | 2008-02-05 | 2015-11-24 | F. Hoffmann-La Roche Ag | Pyridinones and pyridazinones |
| JP5539235B2 (ja) * | 2008-02-29 | 2014-07-02 | エボテック・アーゲー | アミド化合物、組成物およびそれらの使用 |
| WO2010011302A1 (en) * | 2008-07-22 | 2010-01-28 | Chdi, Inc. | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| PT2750677T (pt) | 2011-08-30 | 2017-07-03 | Chdi Foundation Inc | Inibidores de quinurenina-3-monooxigenase, composições farmacêuticas e métodos de utilização dos mesmos |
| US9822058B2 (en) * | 2012-04-05 | 2017-11-21 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| WO2015047982A2 (en) | 2013-09-26 | 2015-04-02 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| US9938252B2 (en) | 2013-09-26 | 2018-04-10 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
-
2013
- 2013-03-13 US US14/390,190 patent/US9822058B2/en active Active
- 2013-03-13 EA EA201491606A patent/EA201491606A1/ru unknown
- 2013-03-13 EP EP13772200.5A patent/EP2833879A4/en not_active Withdrawn
- 2013-03-13 WO PCT/US2013/031051 patent/WO2013151707A1/en not_active Ceased
- 2013-03-13 EP EP16186005.1A patent/EP3130583B1/en active Active
- 2013-03-13 HK HK15106937.6A patent/HK1206264A1/xx unknown
- 2013-03-13 AU AU2013243898A patent/AU2013243898A1/en not_active Abandoned
- 2013-03-13 KR KR1020147027810A patent/KR20150000882A/ko not_active Withdrawn
- 2013-03-13 ES ES16186005T patent/ES2972419T3/es active Active
- 2013-03-13 CN CN201380018756.2A patent/CN104244939A/zh active Pending
- 2013-03-13 JP JP2015504581A patent/JP6275690B2/ja active Active
- 2013-03-13 MX MX2014011946A patent/MX2014011946A/es unknown
- 2013-03-13 BR BR112014024693A patent/BR112014024693A2/pt not_active IP Right Cessation
- 2013-03-13 SG SG11201406311UA patent/SG11201406311UA/en unknown
- 2013-03-13 CA CA2868321A patent/CA2868321A1/en not_active Abandoned
- 2013-04-03 TW TW102112072A patent/TW201402537A/zh unknown
- 2013-04-04 AR ARP130101101A patent/AR090601A1/es unknown
-
2014
- 2014-09-29 IL IL234884A patent/IL234884A0/en unknown
- 2014-10-01 PH PH12014502218A patent/PH12014502218A1/en unknown
-
2017
- 2017-11-14 US US15/813,001 patent/US10442782B2/en active Active
-
2018
- 2018-01-10 JP JP2018001678A patent/JP6622824B2/ja active Active
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