CA2846758C - Triazolopyridine compounds as pde10a inhibitors - Google Patents
Triazolopyridine compounds as pde10a inhibitors Download PDFInfo
- Publication number
- CA2846758C CA2846758C CA2846758A CA2846758A CA2846758C CA 2846758 C CA2846758 C CA 2846758C CA 2846758 A CA2846758 A CA 2846758A CA 2846758 A CA2846758 A CA 2846758A CA 2846758 C CA2846758 C CA 2846758C
- Authority
- CA
- Canada
- Prior art keywords
- pyridin
- methyl
- triazolo
- pyrazole
- amide
- 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.)
- Expired - Fee Related
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- 229940123773 Phosphodiesterase 10A inhibitor Drugs 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 172
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 239000003814 drug Substances 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 65
- 208000035475 disorder Diseases 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 47
- -1 2-Methyl-4-(pyrrolidine-1-carbonyl)-2H-pyrazole-3-carboxylic acid (2-phenyl-[1 ,2,4]triazolo[ 1 ,5-a]pyridin-6-yl)-amide 4-(Azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid Chemical compound 0.000 claims description 43
- JOJAUJFFLWQSGY-UHFFFAOYSA-N 2-methylpyrazole-3,4-dicarboxylic acid Chemical compound CN1N=CC(C(O)=O)=C1C(O)=O JOJAUJFFLWQSGY-UHFFFAOYSA-N 0.000 claims description 39
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- 208000028017 Psychotic disease Diseases 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 238000011282 treatment Methods 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical group 0.000 claims description 22
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 17
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
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- 125000003545 alkoxy group Chemical group 0.000 claims description 11
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- 125000006413 ring segment Chemical group 0.000 claims description 8
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- WESMGXSTLGHHBV-UHFFFAOYSA-N 4-(3-fluoroazetidine-1-carbonyl)-2-methylpyrazole-3-carboxylic acid;2-methyl-4-(morpholine-4-carbonyl)-n-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)pyrazole-3-carboxamide Chemical compound CN1N=CC(C(=O)N2CC(F)C2)=C1C(O)=O.C1=CC2=NC(C=3C=CC=CC=3)=NN2C=C1NC(=O)C=1N(C)N=CC=1C(=O)N1CCOCC1 WESMGXSTLGHHBV-UHFFFAOYSA-N 0.000 claims 1
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Psychology (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Addiction (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11181752.4 | 2011-09-19 | ||
| EP11181752 | 2011-09-19 | ||
| PCT/EP2012/068203 WO2013041472A1 (en) | 2011-09-19 | 2012-09-17 | Triazolopyridine compounds as pde10a inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2846758A1 CA2846758A1 (en) | 2013-03-28 |
| CA2846758C true CA2846758C (en) | 2017-09-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2846758A Expired - Fee Related CA2846758C (en) | 2011-09-19 | 2012-09-17 | Triazolopyridine compounds as pde10a inhibitors |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US8946427B2 (OSRAM) |
| EP (1) | EP2758396B1 (OSRAM) |
| JP (1) | JP2014526533A (OSRAM) |
| KR (1) | KR101584925B1 (OSRAM) |
| CN (1) | CN103827114B (OSRAM) |
| AU (1) | AU2012311713A1 (OSRAM) |
| BR (1) | BR112014006248A2 (OSRAM) |
| CA (1) | CA2846758C (OSRAM) |
| CL (1) | CL2014000641A1 (OSRAM) |
| CO (1) | CO6900144A2 (OSRAM) |
| EA (1) | EA201490599A1 (OSRAM) |
| ES (1) | ES2626801T3 (OSRAM) |
| IL (1) | IL231403A0 (OSRAM) |
| MX (1) | MX2014003025A (OSRAM) |
| PE (1) | PE20141553A1 (OSRAM) |
| PH (1) | PH12014500499A1 (OSRAM) |
| SG (1) | SG11201400759RA (OSRAM) |
| UA (1) | UA108711C2 (OSRAM) |
| WO (1) | WO2013041472A1 (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2757882B1 (en) | 2011-09-22 | 2020-11-04 | Merck Sharp & Dohme Corp. | Imidazopyridyl compounds as aldosterone synthase inhibitors |
| EP2757883B1 (en) | 2011-09-22 | 2021-01-13 | Merck Sharp & Dohme Corp. | Triazolopyridyl compounds as aldosterone synthase inhibitors |
| CA2909477A1 (en) | 2013-04-30 | 2014-11-06 | F. Hoffmann-La Roche Ag | Pd-catalyzed coupling of pyrazole amides |
| TWI652014B (zh) | 2013-09-13 | 2019-03-01 | 美商艾佛艾姆希公司 | 雜環取代之雙環唑殺蟲劑 |
| EP3176168A4 (en) * | 2014-07-30 | 2018-05-02 | Mochida Pharmaceutical Co., Ltd. | Pyrazole derivative manufacturing method |
| EP3176167A4 (en) * | 2014-07-30 | 2018-03-28 | Mochida Pharmaceutical Co., Ltd. | Pyrazole derivative manufacturing method |
| WO2016144351A1 (en) | 2015-03-11 | 2016-09-15 | E. I. Du Pont De Nemours And Company | Heterocycle-substituted bicyclic azole pesticides |
| CN107743486B (zh) | 2015-03-12 | 2021-04-09 | Fmc公司 | 杂环取代的二环唑杀有害生物剂 |
| BR112018007034B1 (pt) | 2015-10-08 | 2022-10-11 | Fmc Corporation | Composto, composição, método para controlar uma praga de invertebrados e semente revestida |
| BR112020003481B1 (pt) * | 2017-08-22 | 2023-12-05 | Bayer Aktiengesellschaft | Derivados de heterocicleno, seus usos, formulação agroquímica, e métodos para controlar pragas animais e para proteger sementes ou uma planta germinativa de pragas |
| CN113906024B (zh) | 2019-05-27 | 2023-10-20 | 日本农药株式会社 | 交联部有氮原子的缩合杂环化合物或其盐类及含该化合物的农业园艺用杀虫剂及其使用方法 |
| AR119140A1 (es) | 2019-06-13 | 2021-11-24 | Pi Industries Ltd | Compuestos heterocíclicos fusionados y su uso como agentes de control de plagas |
| CN110396157B (zh) * | 2019-08-07 | 2021-07-30 | 广州市建筑科学研究院有限公司 | 缓释型聚羧酸纳米减水剂及其制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6355653B1 (en) * | 1999-09-06 | 2002-03-12 | Hoffmann-La Roche Inc. | Amino-triazolopyridine derivatives |
| JP2007508241A (ja) | 2003-07-31 | 2007-04-05 | バイエル・フアーマシユーチカルズ・コーポレーシヨン | Ｐｄｅ１０ａ阻害剤を用いる糖尿病および関連障害の処置方法 |
| NL2000397C2 (nl) * | 2006-01-05 | 2007-10-30 | Pfizer Prod Inc | Bicyclische heteroarylverbindingen als PDE10 inhibitoren. |
| JPWO2010035745A1 (ja) * | 2008-09-25 | 2012-02-23 | 杏林製薬株式会社 | ヘテロ環ビアリール誘導体及びそれらを有効成分とするｐｄｅ阻害剤 |
| WO2010059836A1 (en) * | 2008-11-20 | 2010-05-27 | Decode Genetics Ehf | Substituted aza-bridged bicyclics for cardiovascular and cns disease |
| US8685967B2 (en) * | 2009-04-07 | 2014-04-01 | Merck Sharp & Dohme Corp. | Substituted triazolopyridines and analogs thereof |
| PL2480546T3 (pl) * | 2009-09-24 | 2015-05-29 | Hoffmann La Roche | Pochodne imidazopirydyny i imidazopirymidyny jako inhibitory fosfodiesterazy 10A |
| CN102696239B (zh) | 2009-11-24 | 2020-08-25 | 诺基亚技术有限公司 | 一种设备 |
| TWI487705B (zh) * | 2009-12-17 | 2015-06-11 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之雜芳香族芳基三唑衍生物 |
| TWI485151B (zh) * | 2009-12-17 | 2015-05-21 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之雜芳香族苯基咪唑衍生物 |
| TW201200516A (en) * | 2009-12-17 | 2012-01-01 | Lundbeck & Co As H | Phenylimidazole derivatives comprising an ethynylene linker as PDE10A enzyme inhibitors |
-
2012
- 2012-09-17 EA EA201490599A patent/EA201490599A1/ru unknown
- 2012-09-17 CA CA2846758A patent/CA2846758C/en not_active Expired - Fee Related
- 2012-09-17 EP EP12759445.5A patent/EP2758396B1/en not_active Not-in-force
- 2012-09-17 PH PH1/2014/500499A patent/PH12014500499A1/en unknown
- 2012-09-17 PE PE2014000366A patent/PE20141553A1/es not_active Application Discontinuation
- 2012-09-17 AU AU2012311713A patent/AU2012311713A1/en not_active Abandoned
- 2012-09-17 CN CN201280045398.XA patent/CN103827114B/zh not_active Expired - Fee Related
- 2012-09-17 UA UAA201404029A patent/UA108711C2/uk unknown
- 2012-09-17 WO PCT/EP2012/068203 patent/WO2013041472A1/en not_active Ceased
- 2012-09-17 BR BR112014006248A patent/BR112014006248A2/pt not_active IP Right Cessation
- 2012-09-17 KR KR1020147009588A patent/KR101584925B1/ko not_active Expired - Fee Related
- 2012-09-17 SG SG11201400759RA patent/SG11201400759RA/en unknown
- 2012-09-17 JP JP2014531187A patent/JP2014526533A/ja active Pending
- 2012-09-17 ES ES12759445.5T patent/ES2626801T3/es active Active
- 2012-09-17 MX MX2014003025A patent/MX2014003025A/es active IP Right Grant
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2014
- 2014-03-05 CO CO14047250A patent/CO6900144A2/es unknown
- 2014-03-06 IL IL231403A patent/IL231403A0/en unknown
- 2014-03-17 CL CL2014000641A patent/CL2014000641A1/es unknown
- 2014-03-18 US US14/218,275 patent/US8946427B2/en not_active Expired - Fee Related
- 2014-12-16 US US14/572,312 patent/US9227970B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN103827114A (zh) | 2014-05-28 |
| US8946427B2 (en) | 2015-02-03 |
| UA108711C2 (uk) | 2015-05-25 |
| US9227970B2 (en) | 2016-01-05 |
| AU2012311713A1 (en) | 2014-03-13 |
| JP2014526533A (ja) | 2014-10-06 |
| KR20140075716A (ko) | 2014-06-19 |
| US20140303141A1 (en) | 2014-10-09 |
| MX2014003025A (es) | 2014-05-28 |
| CO6900144A2 (es) | 2014-03-20 |
| PH12014500499A1 (en) | 2014-04-14 |
| KR101584925B1 (ko) | 2016-01-12 |
| EP2758396A1 (en) | 2014-07-30 |
| PE20141553A1 (es) | 2014-10-30 |
| IL231403A0 (en) | 2014-04-30 |
| ES2626801T3 (es) | 2017-07-26 |
| SG11201400759RA (en) | 2014-07-30 |
| US20150099735A1 (en) | 2015-04-09 |
| EA201490599A1 (ru) | 2014-07-30 |
| NZ621597A (en) | 2015-04-24 |
| CA2846758A1 (en) | 2013-03-28 |
| CN103827114B (zh) | 2016-08-24 |
| CL2014000641A1 (es) | 2014-11-14 |
| WO2013041472A1 (en) | 2013-03-28 |
| EP2758396B1 (en) | 2017-03-29 |
| BR112014006248A2 (pt) | 2017-04-11 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20140226 |
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| MKLA | Lapsed |
Effective date: 20190917 |