RU2018111429A - Соли 1-(4-(2-((1-(3,4-дифторфенил)-1н-пиразол-3-ил)метокси)этил)пиперазин-1-ил)этанона - Google Patents
Соли 1-(4-(2-((1-(3,4-дифторфенил)-1н-пиразол-3-ил)метокси)этил)пиперазин-1-ил)этанона Download PDFInfo
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- RU2018111429A RU2018111429A RU2018111429A RU2018111429A RU2018111429A RU 2018111429 A RU2018111429 A RU 2018111429A RU 2018111429 A RU2018111429 A RU 2018111429A RU 2018111429 A RU2018111429 A RU 2018111429A RU 2018111429 A RU2018111429 A RU 2018111429A
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- pain
- disease
- salt
- piperazin
- pyrazol
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- 150000003839 salts Chemical class 0.000 title claims 16
- -1 2 - ((1- (3,4-DIFLUORPHENYL) -1H-PYRAZOL-3-YL) METHOXY) ETHYL Chemical class 0.000 title 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 8
- 208000004454 Hyperalgesia Diseases 0.000 claims 6
- 208000002193 Pain Diseases 0.000 claims 6
- COKUNRYWXTVUAH-UHFFFAOYSA-N 1-[4-[2-[[1-(3,4-difluorophenyl)pyrazol-3-yl]methoxy]ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCOCC1=NN(C=2C=C(F)C(F)=CC=2)C=C1 COKUNRYWXTVUAH-UHFFFAOYSA-N 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- 208000035154 Hyperesthesia Diseases 0.000 claims 3
- 206010065390 Inflammatory pain Diseases 0.000 claims 3
- 206010053552 allodynia Diseases 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 208000021722 neuropathic pain Diseases 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 1
- YJZGDOPAALDWAT-UHFFFAOYSA-N 1-[4-[2-[[1-(3,4-difluorophenyl)pyrazol-3-yl]methoxy]ethyl]piperazin-1-yl]ethanone hydrochloride Chemical group Cl.CC(=O)N1CCN(CCOCc2ccn(n2)-c2ccc(F)c(F)c2)CC1 YJZGDOPAALDWAT-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 108090001030 Lipoproteins Proteins 0.000 claims 1
- 102000004895 Lipoproteins Human genes 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 1
- 229940025084 amphetamine Drugs 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 229960004756 ethanol Drugs 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 150000002688 maleic acid derivatives Chemical class 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 108010085082 sigma receptors Proteins 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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Claims (12)
1. Кристаллическая соль 1-(4-(2-((1-(3,4-дифторфенил)-1Н-пиразол-3-ил)метокси)этил)пиперазин-1-ил)этанона.
2. Кристаллическая соль по п.1, где соль выбрана из группы, состоящей из неорганических кислот, сульфоновых кислот и органических кислот.
3. Кристаллическая соль 1-(4-(2-((1-(3,4-дифторфенил)-1Н-пиразол-3-ил)метокси)этил)пиперазин-1-ил)этанона по п.1, где указанная соль выбрана из гидрохлорида, малеата, фумарата, малоната, сукцината, оксалата и/или гидробромида.
4. Кристаллическая соль 1-(4-(2-((1-(3,4-дифторфенил)-1Н-пиразол-3-ил)метокси)этил)пиперазин-1-ил)этанона по п.1, где соль представляет собой гидрохлорид 1-(4-(2-((1-(3,4-дифторфенил)-1Н-пиразол-3-ил)метокси)этил)пиперазин-1-ил)этанона.
5. Кристаллическая соль 1-(4-(2-((1-(3,4-дифторфенил)-1Н-пиразол-3-ил)метокси)этил)пиперазин-1-ил)этанона по п.1, где соль представляет собой соль малеиновой кислоты и 1-(4-(2-((1-(3,4-дифторфенил)-1Н-пиразол-3-ил)метокси)этил)пиперазин-1-ил)этанона.
6. Фармацевтическая композиция, содержащая по меньшей мере кристаллическую соль по любому из пп. 1-5.
7. Кристаллическая соль по любому из пп. 1-5 для применения в качестве лекарственного средства.
8. Кристаллическая соль по любому из пп. 1-5 для применения при лечении и/или профилактики заболевания или состояния, опосредованного сигма-рецептором.
9. Кристаллическая соль по любому из пп. 1-5 для применения при лечении и/или профилактике заболевания, выбранного из группы, состоящей из диареи; липопротеиновых расстройств; мигрени; ожирения; артрита; гипертензии; аритмии; язвы; дефицита обучения, памяти и внимания; нарушений познавательной способности; нейродегенеративных заболеваний; демиелинизирующих заболеваний; зависимости от наркотиков и химических веществ, включая кокаин, амфетамин, этанол и никотин; поздней дискинезии; ишемического приступа; эпилепсии; инсульта; стресса; рака; психотических состояний, в частности, депрессии, тревоги или шизофрении; воспаления; или аутоиммунных заболеваний.
10. Кристаллическая соль по любому из пп. 1-5 для применения при лечении и/или профилактике заболевания, где заболевание представляет собой боль, предпочтительно невропатическую боль, воспалительную боль или другие состояния, связанные с болью, включая аллодинию и/или гипералгезию.
11. Гидрохлоридная соль по п.4 для применения при лечении и/или профилактике заболевания, где заболевание представляет собой боль, предпочтительно невропатическую боль, воспалительную боль или другие состояния, связанные с болью, включая аллодинию и/или гипералгезию.
12. Малеатная соль по п.5, для применения при лечении и/или профилактике заболевания, где заболевание представляет собой боль, предпочтительно невропатическую боль, воспалительную боль или другие состояния, связанные с болью, включая аллодинию и/или гипералгезию.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15382436.2 | 2015-09-02 | ||
| EP15382436 | 2015-09-02 | ||
| PCT/EP2016/070604 WO2017037166A1 (en) | 2015-09-02 | 2016-09-01 | 1-(4-(2-((1-(3,4-difluorophenyl)-1h-pyrazol-3-yl)methoxy)ethyl) piperazin-1-yl)ethanone salts |
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| RU2018111429A true RU2018111429A (ru) | 2019-10-03 |
| RU2018111429A3 RU2018111429A3 (ru) | 2020-02-04 |
| RU2727974C2 RU2727974C2 (ru) | 2020-07-28 |
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| JP (1) | JP6893916B2 (ru) |
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| CA (1) | CA2997359A1 (ru) |
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| EP3336085A1 (en) | 2016-12-15 | 2018-06-20 | Laboratorios del Dr. Esteve S.A. | Process and intermediate for the preparation of 1-(4-(2-((1-(3,4-difluorophenyl)-1h-pyrazol-3-yl)methoxy)ethyl)piperazin-1-yl)ethanone |
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| DE10259406A1 (de) * | 2002-12-19 | 2004-07-01 | Cognis Deutschland Gmbh & Co. Kg | Milde Detergensgemische |
| DK1781618T3 (da) * | 2004-08-27 | 2012-10-29 | Esteve Labor Dr | Sigma-receptorinhibitorer |
| US20090093405A1 (en) * | 2006-01-19 | 2009-04-09 | Ambrx, Inc. | Non-Natural Amino Acid Polypeptides Having Modified Immunogenicity |
| MY160018A (en) * | 2009-11-25 | 2017-02-15 | Esteve Labor Dr | 4-[2-[[5-methyl-1-(2-naphtalenyl)-1h-pyrazol-3-yl]oxy]ethyl]morpholine salts |
| EP2395003A1 (en) * | 2010-05-27 | 2011-12-14 | Laboratorios Del. Dr. Esteve, S.A. | Pyrazole compounds as sigma receptor inhibitors |
| MA41177A (fr) * | 2014-12-15 | 2017-10-24 | Esteve Labor Dr | Utilisation de ligands des récepteurs sigma dans l'arthrose |
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- 2016-09-01 UA UAA201803348A patent/UA124301C2/uk unknown
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- 2016-09-01 CA CA2997359A patent/CA2997359A1/en not_active Abandoned
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| ZA201801544B (en) | 2019-09-25 |
| KR20180048923A (ko) | 2018-05-10 |
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| WO2017037166A1 (en) | 2017-03-09 |
| US10640468B2 (en) | 2020-05-05 |
| US20180251430A1 (en) | 2018-09-06 |
| JP6893916B2 (ja) | 2021-06-23 |
| JP2018526365A (ja) | 2018-09-13 |
| IL257671A (en) | 2018-04-30 |
| AU2016315396B2 (en) | 2021-05-27 |
| ECSP18015275A (es) | 2018-04-30 |
| TW201713647A (zh) | 2017-04-16 |
| CO2018002429A2 (es) | 2018-07-19 |
| CN108026078A (zh) | 2018-05-11 |
| TWI752916B (zh) | 2022-01-21 |
| MA43157A (fr) | 2018-09-12 |
| RU2018111429A3 (ru) | 2020-02-04 |
| AU2016315396A1 (en) | 2018-03-22 |
| EP3344620B1 (en) | 2022-10-26 |
| CA2997359A1 (en) | 2017-03-09 |
| RU2727974C2 (ru) | 2020-07-28 |
| UA124301C2 (uk) | 2021-08-25 |
| MX2018002435A (es) | 2018-06-15 |
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