RU2015140619A - Соль производного пиразолохинолина и ее кристалл - Google Patents
Соль производного пиразолохинолина и ее кристалл Download PDFInfo
- Publication number
- RU2015140619A RU2015140619A RU2015140619A RU2015140619A RU2015140619A RU 2015140619 A RU2015140619 A RU 2015140619A RU 2015140619 A RU2015140619 A RU 2015140619A RU 2015140619 A RU2015140619 A RU 2015140619A RU 2015140619 A RU2015140619 A RU 2015140619A
- Authority
- RU
- Russia
- Prior art keywords
- acid
- dimethylpyridin
- quinolin
- pyrazolo
- tetrahydrofuran
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims 4
- 239000013078 crystal Substances 0.000 title 1
- -1 2-methoxy-3,5-dimethylpyridin-4-yl Chemical group 0.000 claims 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- CKJDCNZBABIEBZ-HNNXBMFYSA-N 7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-[(3S)-oxolan-3-yl]-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound COC1=NC=C(C)C(C=2C=C3NC(=O)C=4C=NN(C=4C3=CC=2)[C@@H]2COCC2)=C1C CKJDCNZBABIEBZ-HNNXBMFYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 229940098895 maleic acid Drugs 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 229960001367 tartaric acid Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/145—Maleic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (7)
1. Соль (S)-7-(2-метокси-3,5-диметилпиридин-4-ил)-1-(тетрагидрофуран-3-ил)-1H-пиразоло[4,3-c]хинолин-4(5H)-она и кислоты, выбранной из группы, состоящей из хлористоводородной кислоты, бромистоводородной кислоты, серной кислоты, азотной кислоты, фосфорной кислоты, малоновой кислоты, малеиновой кислоты, винной кислоты, метансульфокислоты, бензолсульфокислоты и толуолсульфокислоты.
2. Мономалеат (S)-7-(2-метокси-3,5-диметилпиридин-4-ил)-1-(тетрагидрофуран-3-ил)-1H-пиразоло[4,3-c]хинолин-4(5H)-она.
3. Монобензолсульфонат (S)-7-(2-метокси-3,5-диметилпиридин-4-ил)-1-(тетрагидрофуран-3-ил)-1H-пиразоло[4,3-c]хинолин-4(5H)-она.
4. Соль по п. 1 в кристаллической форме.
5. Мономалеат (S)-7-(2-метокси-3,5-диметилпиридин-4-ил)-1-(тетрагидрофуран-3-ил)-1H-пиразоло[4,3-c]хинолин-4(5H)-она, в кристаллической форме имеющий дифракционный пик при угле дифракции (2θ±0,2°), равном 10,1° при анализе методом рентгеновской порошковой дифракции.
6. Монобензолсульфоната (S)-7-(2-метокси-3,5-диметилпиридин-4-ил)-1-(тетрагидрофуран-3-ил)-1H-пиразоло[4,3-c]хинолин-4(5H)-она, в кристаллической форме имеющий дифракционный пик при угле дифракции (2θ±0,2°), равном 9,9° при анализе методом рентгеновской порошковой дифракции.
7. Фармацевтическая композиция, включающая соль по п. 1 в качестве активного ингредиента.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013-079639 | 2013-04-05 | ||
| JP2013079639 | 2013-04-05 | ||
| PCT/JP2014/059853 WO2014163147A1 (ja) | 2013-04-05 | 2014-04-03 | ピラゾロキノリン誘導体の塩およびその結晶 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2015140619A true RU2015140619A (ru) | 2017-05-11 |
| RU2015140619A3 RU2015140619A3 (ru) | 2018-03-26 |
| RU2655171C2 RU2655171C2 (ru) | 2018-05-24 |
Family
ID=51658438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015140619A RU2655171C2 (ru) | 2013-04-05 | 2014-04-03 | Соль производного пиразолохинолина и ее кристалл |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9573947B2 (ru) |
| EP (1) | EP2982675B1 (ru) |
| JP (1) | JP5666755B1 (ru) |
| KR (1) | KR101997955B1 (ru) |
| CN (1) | CN105121440B (ru) |
| AU (1) | AU2014250392B2 (ru) |
| BR (1) | BR112015024393A2 (ru) |
| CA (1) | CA2907971C (ru) |
| ES (1) | ES2645149T3 (ru) |
| MX (1) | MX359843B (ru) |
| RU (1) | RU2655171C2 (ru) |
| SG (1) | SG11201507897SA (ru) |
| WO (1) | WO2014163147A1 (ru) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017090716A1 (ja) * | 2015-11-26 | 2017-06-01 | 持田製薬株式会社 | ピラゾール誘導体の結晶 |
| CA3061884A1 (en) | 2017-06-01 | 2019-10-29 | Eisai R&D Management Co., Ltd. | Lewy body disease therapeutic agent containing pyrazoloquinoline derivative |
| EP3632439B1 (en) | 2017-06-01 | 2024-03-27 | Eisai R&D Management Co., Ltd. | Dementia therapeutic agent combining pyrazoloquinoline derivative and donepezil |
| JP7293129B2 (ja) * | 2017-06-01 | 2023-06-19 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Ｐｄｅ９阻害剤を含む医薬組成物 |
| MX2019013383A (es) * | 2017-06-01 | 2020-02-20 | Eisai R&D Man Co Ltd | Agente terapeutico para la demencia que combina derivado de pirazoloquinolina y memantina. |
| US11530218B2 (en) | 2020-01-20 | 2022-12-20 | Incyte Corporation | Spiro compounds as inhibitors of KRAS |
| US11739102B2 (en) | 2020-05-13 | 2023-08-29 | Incyte Corporation | Fused pyrimidine compounds as KRAS inhibitors |
| WO2022047093A1 (en) | 2020-08-28 | 2022-03-03 | Incyte Corporation | Vinyl imidazole compounds as inhibitors of kras |
| US11767320B2 (en) | 2020-10-02 | 2023-09-26 | Incyte Corporation | Bicyclic dione compounds as inhibitors of KRAS |
| WO2023064857A1 (en) | 2021-10-14 | 2023-04-20 | Incyte Corporation | Quinoline compounds as inhibitors of kras |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05132484A (ja) * | 1991-04-26 | 1993-05-28 | Otsuka Pharmaceut Factory Inc | ピラゾロキノリン及びピラゾロナフチリジン誘導体 |
| PT760819E (pt) * | 1994-05-24 | 2000-11-30 | Hoffmann La Roche | Derivado dicarbonilicos triciclicos |
| WO2004014910A1 (en) * | 2002-08-07 | 2004-02-19 | Mitsubishi Pharma Corporation | Dihydropyrazolopyridine compounds |
| RU2426734C2 (ru) | 2003-10-03 | 2011-08-20 | Зм Инновейтив Пропертиз Компани | Пиразолопиридины и их аналоги |
| WO2005118583A1 (en) | 2004-05-28 | 2005-12-15 | Millennium Pharmaceuticals, Inc. | 2, 5-dihydro-pyrazolo`4, 3-c!quinolin-4-ones as chk-1 inhibitors |
| JP2006045118A (ja) | 2004-08-04 | 2006-02-16 | Mochida Pharmaceut Co Ltd | 新規ピラゾロキノロン誘導体 |
| KR20080046728A (ko) | 2005-09-15 | 2008-05-27 | 아스카 세이야쿠 가부시키가이샤 | 복소환 화합물, 그의 제조 방법 및 용도 |
| EP2103613B1 (en) | 2006-12-13 | 2016-02-17 | ASKA Pharmaceutical Co., Ltd. | Quinoxaline derivative |
| ME00954B (me) | 2007-05-11 | 2012-06-20 | Pfizer | Aminoheterociklični spojevi |
| UA105362C2 (en) | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| ES2612954T3 (es) * | 2009-03-05 | 2017-05-19 | Astellas Pharma Inc. | Compuestos de quinoxalina |
| NZ594567A (en) | 2009-03-31 | 2013-12-20 | Boehringer Ingelheim Int | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| ES2583528T3 (es) | 2010-09-07 | 2016-09-21 | Astellas Pharma Inc. | Compuesto de pirazoloquinolina |
| EP2573073B1 (en) * | 2011-09-26 | 2014-10-22 | Sanofi | Pyrazoloquinolinone derivatives, preparation thereof and therapeutic use thereof |
| JP6042060B2 (ja) | 2011-09-26 | 2016-12-14 | サノフイ | ピラゾロキノリノン誘導体、その調製および治療上の使用 |
| HUE028555T2 (en) * | 2011-10-07 | 2016-12-28 | Eisai R&D Man Co Ltd | Pyrazolinquinoline Derivatives as PDE9 Inhibitors |
-
2014
- 2014-04-03 KR KR1020157026005A patent/KR101997955B1/ko active IP Right Grant
- 2014-04-03 WO PCT/JP2014/059853 patent/WO2014163147A1/ja active Application Filing
- 2014-04-03 MX MX2015013620A patent/MX359843B/es active IP Right Grant
- 2014-04-03 US US14/778,695 patent/US9573947B2/en active Active
- 2014-04-03 ES ES14780139.3T patent/ES2645149T3/es active Active
- 2014-04-03 CA CA2907971A patent/CA2907971C/en active Active
- 2014-04-03 CN CN201480017423.2A patent/CN105121440B/zh active Active
- 2014-04-03 SG SG11201507897SA patent/SG11201507897SA/en unknown
- 2014-04-03 JP JP2014538559A patent/JP5666755B1/ja active Active
- 2014-04-03 AU AU2014250392A patent/AU2014250392B2/en active Active
- 2014-04-03 BR BR112015024393A patent/BR112015024393A2/pt not_active Application Discontinuation
- 2014-04-03 RU RU2015140619A patent/RU2655171C2/ru active
- 2014-04-03 EP EP14780139.3A patent/EP2982675B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP5666755B1 (ja) | 2015-02-12 |
| RU2015140619A3 (ru) | 2018-03-26 |
| BR112015024393A2 (pt) | 2017-10-24 |
| JPWO2014163147A1 (ja) | 2017-02-16 |
| WO2014163147A1 (ja) | 2014-10-09 |
| MX359843B (es) | 2018-10-12 |
| KR101997955B1 (ko) | 2019-07-08 |
| AU2014250392A1 (en) | 2015-10-15 |
| CA2907971A1 (en) | 2014-10-09 |
| CN105121440A (zh) | 2015-12-02 |
| CA2907971C (en) | 2020-12-29 |
| US9573947B2 (en) | 2017-02-21 |
| AU2014250392B2 (en) | 2018-03-01 |
| US20160046623A1 (en) | 2016-02-18 |
| ES2645149T3 (es) | 2017-12-04 |
| EP2982675A1 (en) | 2016-02-10 |
| EP2982675A4 (en) | 2016-08-10 |
| RU2655171C2 (ru) | 2018-05-24 |
| CN105121440B (zh) | 2017-05-24 |
| KR20150138203A (ko) | 2015-12-09 |
| EP2982675B1 (en) | 2017-08-16 |
| SG11201507897SA (en) | 2015-11-27 |
| MX2015013620A (es) | 2016-02-25 |
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