JP2016512203A5 - - Google Patents
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- JP2016512203A5 JP2016512203A5 JP2015561914A JP2015561914A JP2016512203A5 JP 2016512203 A5 JP2016512203 A5 JP 2016512203A5 JP 2015561914 A JP2015561914 A JP 2015561914A JP 2015561914 A JP2015561914 A JP 2015561914A JP 2016512203 A5 JP2016512203 A5 JP 2016512203A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- alkyl
- compound
- composition
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 63
- 150000003839 salts Chemical class 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 14
- -1 aralkenyl Chemical group 0.000 claims description 11
- BQEUECRVCKCNDI-UHFFFAOYSA-N 4-[4-(2-fluoro-5-methylphenyl)-4-hydroxypiperidine-1-carbonyl]-n-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=CC=C(F)C(C2(O)CCN(CC2)C(=O)C=2C=CC(=CC=2)S(=O)(=O)NC=2SC=CN=2)=C1 BQEUECRVCKCNDI-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 8
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
- BFBYUBBUQICKBI-UHFFFAOYSA-N 4-[4-hydroxy-4-(4-methylphenyl)piperidine-1-carbonyl]-n-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1(O)CCN(C(=O)C=2C=CC(=CC=2)S(=O)(=O)NC=2SC=CN=2)CC1 BFBYUBBUQICKBI-UHFFFAOYSA-N 0.000 claims description 6
- 210000004369 blood Anatomy 0.000 claims description 6
- 239000008280 blood Substances 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 210000003743 erythrocyte Anatomy 0.000 claims description 5
- 208000007475 hemolytic anemia Diseases 0.000 claims description 5
- FKIRFDIHZTZLHM-UHFFFAOYSA-N 4-[4-(3-fluorophenyl)-4-hydroxypiperidine-1-carbonyl]-n-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C1CC(O)(C=2C=C(F)C=CC=2)CCN1C(=O)C(C=C1)=CC=C1S(=O)(=O)NC1=NC=CS1 FKIRFDIHZTZLHM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- XOHUEYCVLUUEJJ-UHFFFAOYSA-I 2,3-Diphosphoglycerate Chemical compound [O-]P(=O)([O-])OC(C(=O)[O-])COP([O-])([O-])=O XOHUEYCVLUUEJJ-UHFFFAOYSA-I 0.000 claims description 2
- VKTRIIOQTOLRAS-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-hydroxypiperidine-1-carbonyl]-n-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1C(=O)C(C=C1)=CC=C1S(=O)(=O)NC1=NC=CS1 VKTRIIOQTOLRAS-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 210000004027 cell Anatomy 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- BAJLNYHQTYVIOS-UHFFFAOYSA-N methyl 1-[4-[(2-methylphenyl)sulfamoyl]benzoyl]-4-phenylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)(C=2C=CC=CC=2)CCN1C(=O)C(C=C1)=CC=C1S(=O)(=O)NC1=CC=CC=C1C BAJLNYHQTYVIOS-UHFFFAOYSA-N 0.000 claims description 2
- WXRMODUITVDKEN-UHFFFAOYSA-N methyl 4-phenyl-1-[4-(phenylsulfamoyl)benzoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)(C=2C=CC=CC=2)CCN1C(=O)C(C=C1)=CC=C1S(=O)(=O)NC1=CC=CC=C1 WXRMODUITVDKEN-UHFFFAOYSA-N 0.000 claims description 2
- AUWWKKUWIICCOE-UHFFFAOYSA-N n-(4-fluorophenyl)-4-[4-hydroxy-4-(methoxymethyl)piperidine-1-carbonyl]benzenesulfonamide Chemical compound C1CC(COC)(O)CCN1C(=O)C1=CC=C(S(=O)(=O)NC=2C=CC(F)=CC=2)C=C1 AUWWKKUWIICCOE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 208000007056 sickle cell anemia Diseases 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 208000005980 beta thalassemia Diseases 0.000 claims 4
- 208000022806 beta-thalassemia major Diseases 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 108700014121 Pyruvate Kinase Deficiency of Red Cells Proteins 0.000 claims 2
- 208000035623 congenital anemia Diseases 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- 208000030760 Anaemia of chronic disease Diseases 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 206010018910 Haemolysis Diseases 0.000 claims 1
- 208000000733 Paroxysmal Hemoglobinuria Diseases 0.000 claims 1
- 102100036050 Phosphatidylinositol N-acetylglucosaminyltransferase subunit A Human genes 0.000 claims 1
- 208000008601 Polycythemia Diseases 0.000 claims 1
- 208000004622 abetalipoproteinemia Diseases 0.000 claims 1
- 208000007502 anemia Diseases 0.000 claims 1
- 208000022400 anemia due to chronic disease Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 230000008588 hemolysis Effects 0.000 claims 1
- 208000009601 hereditary spherocytosis Diseases 0.000 claims 1
- 201000003045 paroxysmal nocturnal hemoglobinuria Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 description 9
- 101001091538 Homo sapiens Pyruvate kinase PKM Proteins 0.000 description 4
- 102100034911 Pyruvate kinase PKM Human genes 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- DWOBOHJJJHTHGQ-UHFFFAOYSA-N CC(C)CC(CC1)(CCN1C(c(cc1)ccc1NS(c1c2nc(N)[s]c2ccc1)(=O)=O)=O)O Chemical compound CC(C)CC(CC1)(CCN1C(c(cc1)ccc1NS(c1c2nc(N)[s]c2ccc1)(=O)=O)=O)O DWOBOHJJJHTHGQ-UHFFFAOYSA-N 0.000 description 1
- JTGUGSWLWPKCGF-UHFFFAOYSA-N CC(C)CC(CC1)(CCN1C(c(cc1)ccc1NS(c1c2nccnc2ccc1)(=O)=O)=O)O Chemical compound CC(C)CC(CC1)(CCN1C(c(cc1)ccc1NS(c1c2nccnc2ccc1)(=O)=O)=O)O JTGUGSWLWPKCGF-UHFFFAOYSA-N 0.000 description 1
- PNHFJXKSMARJSQ-UHFFFAOYSA-N CC(C)CC(CC1)(CCN1C(c(cc1)ccc1NS(c1cccc2c1ncnc2O)(=O)=O)=O)O Chemical compound CC(C)CC(CC1)(CCN1C(c(cc1)ccc1NS(c1cccc2c1ncnc2O)(=O)=O)=O)O PNHFJXKSMARJSQ-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2013/072688 WO2014139144A1 (en) | 2013-03-15 | 2013-03-15 | Therapeutic compounds and compositions |
| CNPCT/CN2013/072688 | 2013-03-15 | ||
| PCT/CN2014/000260 WO2014139325A1 (en) | 2013-03-15 | 2014-03-13 | Therapeutic compounds and compositions |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017042775A Division JP2017105832A (ja) | 2013-03-15 | 2017-03-07 | 治療化合物および組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016512203A JP2016512203A (ja) | 2016-04-25 |
| JP2016512203A5 true JP2016512203A5 (https=) | 2017-04-13 |
| JP6374413B2 JP6374413B2 (ja) | 2018-08-15 |
Family
ID=51535825
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015561914A Expired - Fee Related JP6374413B2 (ja) | 2013-03-15 | 2014-03-13 | 治療化合物および組成物 |
| JP2017042775A Withdrawn JP2017105832A (ja) | 2013-03-15 | 2017-03-07 | 治療化合物および組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017042775A Withdrawn JP2017105832A (ja) | 2013-03-15 | 2017-03-07 | 治療化合物および組成物 |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US20160046579A1 (https=) |
| EP (1) | EP2970189B1 (https=) |
| JP (2) | JP6374413B2 (https=) |
| CN (1) | CN105121425A (https=) |
| AR (1) | AR095557A1 (https=) |
| AU (1) | AU2014231564B2 (https=) |
| BR (1) | BR112015023760A2 (https=) |
| CA (1) | CA2903067A1 (https=) |
| CL (1) | CL2015002767A1 (https=) |
| CR (1) | CR20150571A (https=) |
| ES (1) | ES2803548T3 (https=) |
| HK (1) | HK1216175A1 (https=) |
| IL (1) | IL241352A0 (https=) |
| MX (1) | MX2015012882A (https=) |
| NI (1) | NI201500140A (https=) |
| PE (1) | PE20151793A1 (https=) |
| PH (1) | PH12015502161A1 (https=) |
| RU (1) | RU2015143908A (https=) |
| SG (1) | SG11201507332SA (https=) |
| TW (1) | TW201444797A (https=) |
| WO (2) | WO2014139144A1 (https=) |
| ZA (1) | ZA201506487B (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014139144A1 (en) * | 2013-03-15 | 2014-09-18 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| RS62017B1 (sr) | 2014-09-17 | 2021-07-30 | Celgene Car Llc | Mk2 inhibitori i njihova upotreba |
| CN104817490B (zh) * | 2015-05-13 | 2017-10-13 | 北京大学 | 氨基二硫代甲酸酯类化合物及其制备方法与应用 |
| EP4006038A1 (en) | 2015-12-09 | 2022-06-01 | Cadent Therapeutics, Inc. | Thienopyrimidinone nmda receptor modulators and uses thereof |
| SMT202000534T1 (it) | 2015-12-09 | 2020-11-10 | Cadent Therapeutics Inc | Modulatori eteroaromatici del recettore nmda e loro usi |
| GB201617758D0 (en) * | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
| ES2975336T3 (es) | 2016-12-22 | 2024-07-04 | Novartis Ag | Moduladores del receptor NMDA y usos de los mismos |
| ES2747768T3 (es) * | 2017-03-20 | 2020-03-11 | Forma Therapeutics Inc | Composiciones de pirrolopirrol como activadores de quinasa de piruvato (PKR) |
| CN107298685A (zh) * | 2017-06-29 | 2017-10-27 | 上海合全药业股份有限公司 | 一种8‑(叔丁氧羰基)‑1‑氧杂‑8‑氮杂螺[4.5]癸烷‑2‑羧酸的合成方法 |
| DK3668513T3 (da) * | 2017-08-15 | 2022-01-10 | Agios Pharmaceuticals Inc | Pyruvatkinase-aktiveringsmidler til anvendelse til behandling af blodsygdomme |
| SG10202011632RA (en) | 2017-10-27 | 2021-01-28 | Boehringer Ingelheim Int | Pyridine carbonyl derivatives and therapeutic uses thereof as trpc6 inhibitors |
| EP3604288B1 (en) | 2018-08-02 | 2024-04-10 | Development Center for Biotechnology | Regioselective one-step process for synthesizing 2-hydroxyquinoxaline |
| BR112021001967A2 (pt) | 2018-08-03 | 2021-04-27 | Cadent Therapeutics, Inc. | moduladores de receptor nmda heteroaromáticos e usos dos mesmos |
| US12053458B2 (en) | 2018-09-19 | 2024-08-06 | Novo Nordisk Health Care Ag | Treating sickle cell disease with a pyruvate kinase R activating compound |
| ES2989438T3 (es) * | 2018-09-19 | 2024-11-26 | Novo Nordisk Healthcare Ag | Activación de la piruvato cinasa R |
| JP7792670B2 (ja) * | 2018-12-18 | 2025-12-26 | 株式会社デ・ウエスタン・セラピテクス研究所 | イソキノリンスルホニルクロリド酸付加塩及びその製造方法 |
| WO2021029450A1 (ko) * | 2019-08-09 | 2021-02-18 | 한국화학연구원 | 신규한 피리미딘 설폰아마이드 유도체 및 이를 유효성분으로 포함하는 암 예방 또는 치료용 약학 조성물 |
| US20220378756A1 (en) | 2019-09-19 | 2022-12-01 | Forma Therapeutics, Inc. | Activating pyruvate kinase r |
| CA3188340A1 (en) | 2020-08-13 | 2022-02-17 | Boehringer Ingelheim International Gmbh | Treatment of cognitive impairement associated with schizophrenia |
| CA3195702A1 (en) | 2020-10-13 | 2022-04-21 | Boehringer Ingelheim International Gmbh | Process of reworking |
| CN112773800B (zh) * | 2021-01-25 | 2021-10-15 | 南通大学 | 哌啶-1-二硫代甲酸-3-甲基-1，4-二氧-1，4-二氢萘-2-甲基酯的用途 |
| US11566030B2 (en) | 2021-02-08 | 2023-01-31 | Global Blood Therapeutics, Inc. | Substituted 2,6-dihydropyrrolo[3,4-c]pyrazoles as pyruvate kinase activators |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
| AU2022273980B2 (en) * | 2021-05-12 | 2026-02-19 | Boehringer Ingelheim International Gmbh | Pyridine derivatives with c-linked cyclic substituents as cgas inhibitors |
| PE20242344A1 (es) | 2021-05-12 | 2024-12-16 | Boehringer Ingelheim Int | DERIVADOS DE PIRIDINA CON SUSTITUYENTES CICLICOS LIGADOS A N COMO INHIBIDORES DE cGAS |
| KR20240124324A (ko) | 2021-12-21 | 2024-08-16 | 시노허브 파마슈티컬 씨오., 엘티디 | 비스(아자니릴리덴)설포닐 구조를 함유하는 화합물 및 약제에서의 이의 용도 |
| CN115073422A (zh) * | 2022-07-28 | 2022-09-20 | 成都普瑞熙药业有限公司 | 一种制备4-(1-甲基-1h-吡唑-5-基)哌啶及其盐的方法 |
| ES2975743A1 (es) * | 2022-11-22 | 2024-07-12 | Moehs Iberica Sl | Metodo de preparacion de mitapivat, intermedios de sintesis de mitapivat y metodos de preparacion de los mismos |
| CN121175042A (zh) | 2023-05-26 | 2025-12-19 | 赛诺哈勃药业（成都）有限公司 | 含二氮杂亚基磺酰结构化合物的药物组合物在治疗贫血相关疾病中的用途 |
| WO2025191185A1 (en) * | 2024-03-15 | 2025-09-18 | Domain Therapeutics | Azine-based compounds as par-2 inhibitors and therapeutic uses thereof |
| WO2025233901A1 (en) | 2024-05-09 | 2025-11-13 | Biohaven Therapeutics Ltd. | Activators of pyruvate kinase isoform m2 and methods for treating neurodegenerative disease |
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2013
- 2013-03-15 WO PCT/CN2013/072688 patent/WO2014139144A1/en not_active Ceased
-
2014
- 2014-03-13 CN CN201480021459.8A patent/CN105121425A/zh active Pending
- 2014-03-13 AU AU2014231564A patent/AU2014231564B2/en not_active Ceased
- 2014-03-13 MX MX2015012882A patent/MX2015012882A/es unknown
- 2014-03-13 HK HK16104168.0A patent/HK1216175A1/zh unknown
- 2014-03-13 EP EP14765650.8A patent/EP2970189B1/en active Active
- 2014-03-13 RU RU2015143908A patent/RU2015143908A/ru not_active Application Discontinuation
- 2014-03-13 PE PE2015002010A patent/PE20151793A1/es not_active Application Discontinuation
- 2014-03-13 BR BR112015023760A patent/BR112015023760A2/pt not_active IP Right Cessation
- 2014-03-13 CA CA2903067A patent/CA2903067A1/en not_active Abandoned
- 2014-03-13 US US14/776,635 patent/US20160046579A1/en not_active Abandoned
- 2014-03-13 ES ES14765650T patent/ES2803548T3/es active Active
- 2014-03-13 SG SG11201507332SA patent/SG11201507332SA/en unknown
- 2014-03-13 WO PCT/CN2014/000260 patent/WO2014139325A1/en not_active Ceased
- 2014-03-13 JP JP2015561914A patent/JP6374413B2/ja not_active Expired - Fee Related
- 2014-03-14 US US14/210,583 patent/US9108921B2/en active Active
- 2014-03-14 TW TW103109338A patent/TW201444797A/zh unknown
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