JP2015506993A5 - - Google Patents
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- Publication number
- JP2015506993A5 JP2015506993A5 JP2014556989A JP2014556989A JP2015506993A5 JP 2015506993 A5 JP2015506993 A5 JP 2015506993A5 JP 2014556989 A JP2014556989 A JP 2014556989A JP 2014556989 A JP2014556989 A JP 2014556989A JP 2015506993 A5 JP2015506993 A5 JP 2015506993A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkoxy
- indazole
- alkyl
- hydroxy
- 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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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000001931 aliphatic group Chemical group 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 208000035475 disorder Diseases 0.000 claims description 14
- -1 phenyl group Carboxamide compounds Chemical class 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 201000000980 schizophrenia Diseases 0.000 claims description 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 208000020925 Bipolar disease Diseases 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 208000020401 Depressive disease Diseases 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 201000009032 substance abuse Diseases 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
- 208000019022 Mood disease Diseases 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 231100000736 substance abuse Toxicity 0.000 claims description 4
- 208000011117 substance-related disease Diseases 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 claims description 3
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 3
- 208000029742 colonic neoplasm Diseases 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 208000032839 leukemia Diseases 0.000 claims description 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 230000002611 ovarian Effects 0.000 claims description 3
- 230000002018 overexpression Effects 0.000 claims description 3
- 201000002528 pancreatic cancer Diseases 0.000 claims description 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- DITBWPUMEUDVLU-UHFFFAOYSA-N 1h-indazole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NNC2=C1 DITBWPUMEUDVLU-UHFFFAOYSA-N 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 208000024714 major depressive disease Diseases 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 201000009916 Postpartum depression Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 208000025748 atypical depressive disease Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 208000012672 seasonal affective disease Diseases 0.000 claims 2
- 208000001495 Disorganized Schizophrenia Diseases 0.000 claims 1
- 208000036755 Schizophrenia simple Diseases 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 206010007776 catatonia Diseases 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 208000024732 dysthymic disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000003995 melancholia Diseases 0.000 claims 1
- 230000036651 mood Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000003368 psychostimulant agent Substances 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 208000002320 spinal muscular atrophy Diseases 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000001107 psychogenic effect Effects 0.000 description 1
- 210000001032 spinal nerve Anatomy 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12156292.0 | 2012-02-21 | ||
| EP12156292 | 2012-02-21 | ||
| PCT/EP2013/052400 WO2013124158A1 (en) | 2012-02-21 | 2013-02-07 | 1h-indazole-3-carboxamide compounds as glycogen synthase kinase 3 beta inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015506993A JP2015506993A (ja) | 2015-03-05 |
| JP2015506993A5 true JP2015506993A5 (https=) | 2017-01-05 |
| JP6141331B2 JP6141331B2 (ja) | 2017-06-07 |
Family
ID=47739223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014556989A Active JP6141331B2 (ja) | 2012-02-21 | 2013-02-07 | グリコーゲンシンターゼキナーゼ３ベータ阻害剤としての１ｈ−インダゾール−３−カルボキサミド化合物 |
Country Status (26)
| Country | Link |
|---|---|
| US (3) | US9611249B2 (https=) |
| EP (1) | EP2817302B1 (https=) |
| JP (1) | JP6141331B2 (https=) |
| KR (1) | KR20140130124A (https=) |
| CN (1) | CN104093712B (https=) |
| AR (1) | AR090086A1 (https=) |
| AU (1) | AU2013224302B2 (https=) |
| BR (1) | BR112014018655B1 (https=) |
| CA (1) | CA2860250C (https=) |
| CY (1) | CY1117469T1 (https=) |
| DK (1) | DK2817302T3 (https=) |
| EA (1) | EA024939B1 (https=) |
| ES (1) | ES2564961T3 (https=) |
| GE (1) | GEP20166489B (https=) |
| HR (1) | HRP20160125T1 (https=) |
| HU (1) | HUE026893T2 (https=) |
| IL (1) | IL233824A (https=) |
| ME (1) | ME02353B (https=) |
| MX (1) | MX351287B (https=) |
| PL (1) | PL2817302T3 (https=) |
| RS (1) | RS54567B1 (https=) |
| SG (2) | SG10201701649YA (https=) |
| SI (1) | SI2817302T1 (https=) |
| SM (1) | SMT201600053B (https=) |
| UA (1) | UA112564C2 (https=) |
| WO (1) | WO2013124158A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS54539B1 (sr) * | 2012-02-21 | 2016-06-30 | Aziende Chimiche Riunite Angelini Francesco - A.C.R.A.F. - S.P.A. | Upotreba 1h-indazol-3-karboksamidnih jedinjenja kao inhibitora kinaze 3-beta glikogen sintetaze |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| JP6064062B2 (ja) | 2013-03-15 | 2017-01-18 | ファイザー・インク | Ａｍｐｋを活性化させるインダゾール化合物 |
| MX2016012208A (es) | 2014-03-20 | 2017-01-26 | Samumed Llc | Indazol-3-carboxamidas 5-substituidas y preparacion y uso de las mismas. |
| MY199070A (en) | 2016-06-01 | 2023-10-12 | Bayer Pharma AG | Substituted indazoles useful for treatment and prevention of allergic and/or inflammatory diseaes in animals |
| US20190298705A1 (en) * | 2016-06-08 | 2019-10-03 | Glaxosmithkline Intellectual Property Development Limited | Chemical Compounds |
| AU2019224075A1 (en) | 2018-02-23 | 2020-09-10 | Samumed, Llc | 5-heteroaryl substituted indazole-3-carboxamides and preparation and use thereof |
| PT3790873T (pt) * | 2018-05-07 | 2022-05-11 | Acraf | Compostos de 1h-indazole-3-carboxamida como inibidores da glicogénio sintase cinase 3 beta |
| CN112351819B (zh) | 2018-06-05 | 2023-11-10 | 开动疗法公司 | 治疗恶性淋巴增生性疾病的方法 |
| AU2019339355A1 (en) | 2018-09-13 | 2021-05-13 | Bristol-Myers Squibb Company | Indazole carboxamides as kinase inhibitors |
| KR102906523B1 (ko) | 2018-09-13 | 2025-12-30 | 브리스톨-마이어스 스큅 컴퍼니 | 수용체-상호작용 단백질 키나제 1 (ripk1) 억제제로서의 1h-인다졸 카르복스아미드 |
| WO2022125377A1 (en) * | 2020-12-08 | 2022-06-16 | Disarm Therapeutics, Inc. | Benzopyrazole inhibitors of sarm1 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ257545A (en) | 1992-11-05 | 1997-01-29 | Smithkline Beecham Plc | Heterocyclic (especially piperidine) derivatives and pharmaceutical compositions |
| IT1291569B1 (it) * | 1997-04-15 | 1999-01-11 | Angelini Ricerche Spa | Indazolammidi come agenti serotoninergici |
| US20060135516A1 (en) * | 2002-08-10 | 2006-06-22 | Astex Technology, Ltd. | 3-(Carbonyl) 1h-indazole compounds as cyclin dependent kinases (cdk) inhibitors |
| GB0218625D0 (en) | 2002-08-10 | 2002-09-18 | Astex Technology Ltd | Pharmaceutical compounds |
| ITMI20030287A1 (it) | 2003-02-18 | 2004-08-19 | Acraf | Indazolammidi dotate di attivita' analgesica metodo, per |
| ITMI20030972A1 (it) | 2003-05-15 | 2004-11-16 | Acraf | Indazolo dotato di attivita' analgesica, metodo per prepararlo e composizione farmaceutica che lo comprende. |
| WO2005014554A1 (en) * | 2003-08-08 | 2005-02-17 | Astex Therapeutics Limited | 1h-indazole-3-carboxamide compounds as mapkap kinase modulators |
| GB0414438D0 (en) * | 2004-06-28 | 2004-07-28 | Syngenta Participations Ag | Chemical compounds |
| AR052559A1 (es) * | 2005-01-21 | 2007-03-21 | Astex Therapeutics Ltd | Derivados de pirazol para inhibir cdk's y gsk's |
| EP1692939A1 (en) * | 2005-02-19 | 2006-08-23 | Bayer CropScience S.A. | Pesticidal substituted piperidines |
| JP5451602B2 (ja) * | 2007-06-08 | 2014-03-26 | アッヴィ・インコーポレイテッド | キナーゼ阻害薬としての５−ヘテロアリール置換インダゾール類 |
| UA99927C2 (uk) | 2007-11-12 | 2012-10-25 | Ацьенде Кимике Риуните Анджелини Франческо А.Чи.Р.А.Ф. С.П.А. | Медикамент, який є активним при невропатичному болі |
| US8377968B2 (en) * | 2008-06-02 | 2013-02-19 | Zalicus Pharmaceuticals, Ltd. | N-piperidinyl acetamide derivatives as calcium channel blockers |
| TW201040191A (en) | 2009-03-27 | 2010-11-16 | Abbott Gmbh & Co Kg | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
| US7947728B1 (en) | 2009-11-11 | 2011-05-24 | Hoffmann-La Roche Inc. | Indole and indazole analogs as glycogen synthase activators |
-
2013
- 2013-02-07 CA CA2860250A patent/CA2860250C/en active Active
- 2013-02-07 WO PCT/EP2013/052400 patent/WO2013124158A1/en not_active Ceased
- 2013-02-07 ME MEP-2016-29A patent/ME02353B/me unknown
- 2013-02-07 KR KR20147022708A patent/KR20140130124A/ko not_active Ceased
- 2013-02-07 RS RS20160132A patent/RS54567B1/sr unknown
- 2013-02-07 GE GEAP201313563A patent/GEP20166489B/en unknown
- 2013-02-07 ES ES13704910.2T patent/ES2564961T3/es active Active
- 2013-02-07 PL PL13704910T patent/PL2817302T3/pl unknown
- 2013-02-07 CN CN201380007411.7A patent/CN104093712B/zh active Active
- 2013-02-07 JP JP2014556989A patent/JP6141331B2/ja active Active
- 2013-02-07 US US14/373,100 patent/US9611249B2/en active Active
- 2013-02-07 EP EP13704910.2A patent/EP2817302B1/en active Active
- 2013-02-07 MX MX2014009297A patent/MX351287B/es active IP Right Grant
- 2013-02-07 BR BR112014018655-3A patent/BR112014018655B1/pt active IP Right Grant
- 2013-02-07 SI SI201330134T patent/SI2817302T1/sl unknown
- 2013-02-07 SG SG10201701649YA patent/SG10201701649YA/en unknown
- 2013-02-07 HU HUE13704910A patent/HUE026893T2/en unknown
- 2013-02-07 DK DK13704910.2T patent/DK2817302T3/en active
- 2013-02-07 SG SG11201403602WA patent/SG11201403602WA/en unknown
- 2013-02-07 HR HRP20160125TT patent/HRP20160125T1/hr unknown
- 2013-02-07 AU AU2013224302A patent/AU2013224302B2/en active Active
- 2013-02-07 EA EA201491449A patent/EA024939B1/ru unknown
- 2013-02-19 AR ARP130100502A patent/AR090086A1/es active IP Right Grant
- 2013-07-02 UA UAA201406961A patent/UA112564C2/uk unknown
-
2014
- 2014-07-27 IL IL233824A patent/IL233824A/en active IP Right Grant
-
2016
- 2016-02-23 SM SM201600053T patent/SMT201600053B/xx unknown
- 2016-03-15 CY CY20161100219T patent/CY1117469T1/el unknown
-
2017
- 2017-02-22 US US15/439,172 patent/US10160746B2/en active Active
- 2017-03-07 US US15/451,966 patent/US20170174657A1/en not_active Abandoned
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