RU2007105968A - Новые пиперидиновые производные для лечения депрессии - Google Patents
Новые пиперидиновые производные для лечения депрессии Download PDFInfo
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- RU2007105968A RU2007105968A RU2007105968/04A RU2007105968A RU2007105968A RU 2007105968 A RU2007105968 A RU 2007105968A RU 2007105968/04 A RU2007105968/04 A RU 2007105968/04A RU 2007105968 A RU2007105968 A RU 2007105968A RU 2007105968 A RU2007105968 A RU 2007105968A
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- Prior art keywords
- benzo
- nrc
- phenyl
- benzyl
- halogen
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- QTBCINIXWAQBGB-UHFFFAOYSA-N CNS(c1cccc(C(NCCCN2CCCCC2)=O)c1)(=O)=O Chemical compound CNS(c1cccc(C(NCCCN2CCCCC2)=O)c1)(=O)=O QTBCINIXWAQBGB-UHFFFAOYSA-N 0.000 description 1
- NYJJONQIOIDIFH-UHFFFAOYSA-N COc(ccc(C(NCCCN1CCCCC1)=O)c1)c1F Chemical compound COc(ccc(C(NCCCN1CCCCC1)=O)c1)c1F NYJJONQIOIDIFH-UHFFFAOYSA-N 0.000 description 1
- YOUZLGWWEGMNGM-UHFFFAOYSA-N COc1ccc(C(NCCCN2CCCCC2)=O)c(CCC=C)c1 Chemical compound COc1ccc(C(NCCCN2CCCCC2)=O)c(CCC=C)c1 YOUZLGWWEGMNGM-UHFFFAOYSA-N 0.000 description 1
- MOWVOVGZZORJKZ-UHFFFAOYSA-N O=C(c(cc1)cc(OC2)c1NC2=O)NCCCN1CCCCC1 Chemical compound O=C(c(cc1)cc(OC2)c1NC2=O)NCCCN1CCCCC1 MOWVOVGZZORJKZ-UHFFFAOYSA-N 0.000 description 1
- MFSIIDQPBLNEBA-UHFFFAOYSA-N O=C(c(cc1)cc2c1[s]nn2)NCCCN1CCCCC1 Chemical compound O=C(c(cc1)cc2c1[s]nn2)NCCCN1CCCCC1 MFSIIDQPBLNEBA-UHFFFAOYSA-N 0.000 description 1
- YOWRIHVWUZAOGM-UHFFFAOYSA-N O=C(c(cc1)cc2c1nn[s]2)NCCCN1CCCCC1 Chemical compound O=C(c(cc1)cc2c1nn[s]2)NCCCN1CCCCC1 YOWRIHVWUZAOGM-UHFFFAOYSA-N 0.000 description 1
- YYBGAXCSRIZACM-UHFFFAOYSA-N O=C(c1cc(F)cc(C(F)(F)F)c1)NCCCN1CCCCC1 Chemical compound O=C(c1cc(F)cc(C(F)(F)F)c1)NCCCN1CCCCC1 YYBGAXCSRIZACM-UHFFFAOYSA-N 0.000 description 1
- FNAFKFYEBNLVAG-UHFFFAOYSA-N O=C(c1cccc(Cl)c1)NCCCN1CCCCC1 Chemical compound O=C(c1cccc(Cl)c1)NCCCN1CCCCC1 FNAFKFYEBNLVAG-UHFFFAOYSA-N 0.000 description 1
- GLSBOJQPSCPOPC-UHFFFAOYSA-N Oc(cc1)ccc1-c(cc1)ccc1C(NCCCN1CCCCC1)=O Chemical compound Oc(cc1)ccc1-c(cc1)ccc1C(NCCCN1CCCCC1)=O GLSBOJQPSCPOPC-UHFFFAOYSA-N 0.000 description 1
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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Claims (10)
1. Соединение формулы I, его фармацевтически приемлемые соль, его диастереомеры, энантиомеры или их смеси:
где Ar1 выбран из С6-10арила и С2-9гетероарила, где указанные С6-10арил и С2-9гетероарил возможно замещены одной или более группами, выбранными из -R, -NO2, -OR, -Cl, -Br, -I, -F, -CF3, -OCF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3Н, -SO2R, -SO2NR, -S(=O)R, -CN, -ОН, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород, С3-6циклоалкил, С3-6гетероциклил, фенил, бензил, C1-6алкил или С2-6алкенил и где указанный R дополнительно возможно замещен одной или более группами, выбранными из метила, гидрокси и галогена, либо Ar1 представляет собой
где Ar выбран из фенила, пиридила, нафтила, бензо[1,3]диоксолила, хинолила, индолила, бензотриазолила, бензимидазолила, 2,3-дигидро-бензофуранила, бензо[1,2,3]тиадиазолила, бензотиазолила и 4Н-бензо[1,4]оксазин-3-он-ила;
R1, R2 и R3 независимо выбраны из -R, -NO2, -OR, -Cl, -Br, -I, -F, -CF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3Н, -SO2R, -SO2NR, -S(=O)R, -CN, -ОН, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород, С5-6циклоалкил, С3-5гетероциклил, фенил, бензил, С1-4алкил или С2-4алкенил и где указанный R дополнительно возможно замещен одной или более группами, выбранными из метила, гидрокси и галогена.
2. Соединение по п.1, где Ar1 представляет собой
где Ar выбран из фенила, пиридила, нафтила, бензо[1,3]диоксолила, хинолила, индолила, бензотриазолила, бензимидазолила, 2,3-дигидро-бензофуранила, бензо[1,2,3]тиадиазолила, бензотиазолила и 4Н-бензо[1,4]оксазин-3-он-ила;
R1, R2 и R3 независимо выбраны из -R, -NO2, -OR, -Cl, -Br, -I, -F, -CF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3Н, -SO2R, -SO2NR, -S(=O)R, -CN, -ОН, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород, С5-6циклоалкил, С3-5гетероциклил, фенил, бензил, С1-4алкил или С2-4алкенил и где указанный R дополнительно возможно замещен одной или более группами, выбранными из метила, гидрокси и галогена.
3. Соединение по п.1, где Ar1 выбран из фенила, 2-пиридила, 2-нафтила, бензо[1,3]диоксол-5-ила, хинол-2-ила, 1Н-индол-4-ила, 1Н-индол-7-ила, 1Н-бензотриазол-5-ила, 1Н-бензоимидазол-5-ила, 2,3-дигидро-бензофуран-5-ила, бензо[1,2,3]тиадиазол-5-ила, бензо[1,2,3]тиадиазол-6-ила, бензотиазол-6-ила и 4Н-бензо[1,4]оксазин-3-он-7-ила, где Ar1 дополнительно возможно замещен одной или более группами, выбранными из С1-4алкила, С2-4алкенила, С1-4алкокси, С1-4алкенилокси, фенокси, бензила, ацетоамино, метилсульфонила, метоксикарбонила, нитро, хлоро, фторо, метокси, этокси, изопропилокси, метилтио, циано, диметиламино, гидрокси, метиламиносульфонила, трифторметила, трифторметокси, фенила, фенокси, бензила, 4-гидрокси-фенила, диэтиламино, метилсульфонила, аминосульфонила, циклогексила, 1-пирролила, 1H-пиразол-3-ила, 5-тетразолила, 1-пиперидинила, 1-пиразолила, метилсульфонилметила, 3,5-диметил-пиразолила, пирролидин-2-он-1-ила.
5. Соединение по любому из пп.1-4 для применения в качестве лекарственного средства.
6. Применение соединения по любому из пп.1-4 в изготовлении лекарственного средства для лечения депрессии.
7. Фармацевтическая композиция, содержащая соединение по любому из пп.1-4 и фармацевтически приемлемый носитель.
8. Способ лечения депрессии у теплокровного животного, включающий стадию введения указанному животному, нуждающемуся в таком лечении, терапевтически эффективного количества соединения по любому из пп.1-4.
9. Способ получения соединения формулы I
включающий взаимодействие Ar1-СОХ или (Ar1-СО)2O с 3-(1-пиперидино)пропиламином,
где Ar1 выбран из С6-10арила и С2-9гетероарила, где указанные С6-10арил и С2-9гетероарил возможно замещены одной или более группами, выбранными из -R, -NO2, -OR, -Cl, -Br, -I, -F, -CF3, -OCF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3Н, -SO2R, -SO2NR, -S(=O)R, -CN, -ОН, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород, С3-6циклоалкил, С3-6гетероциклил, фенил, бензил, C1-6алкил или С2-6алкенил, и где указанный R дополнительно возможно замещен одной или более группами, выбранными из метила, гидрокси и галогена, и
Х выбран из -ОН и галогена.
10. Способ получения соединения формулы I
включающий объединение Ar1-СОХ или (Ar1-СО)2O с 3-(1-пиперидино)пропиламином,
где Ar1 представляет собой
где Ar выбран из фенила, пиридила, нафтила, бензо[1,3]диоксолила, хинолила, индолила, бензотриазолила, бензимидазолила, 2,3-дигидро-бензофуранила, бензо[1,2,3]тиадиазолила, бензотиазолила и 4Н-бензо[1,4]оксазин-3-он-ила;
R1, R2 и R3 независимо выбраны из -R, -NO2, -OR, -Cl, -Br, -I, -F, -CF3, -OCF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3Н, -SO2R, -SO2NR, -S(=O)R, -CN, -ОН, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород, С5-6циклоалкил, С3-5гетероциклил, фенил, бензил, С1-4алкил или С2-4алкенил и где указанный R дополнительно возможно замещен одной или более группами, выбранными из метила, гидрокси и галогена; и
Х выбран из - ОН и галогена.
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CA2627630A1 (en) * | 2005-12-20 | 2007-06-28 | Novartis Ag | Nicotinic acid derivatives as modulators of metabotropic glutamate receptors |
DE102006060598A1 (de) * | 2006-12-21 | 2008-06-26 | Merck Patent Gmbh | Tetrahydrobenzoisoxazole |
SK542007A3 (sk) * | 2007-04-20 | 2008-11-06 | Unimed Pharma, Spol. S R. O. | Substituované sulfónamidy, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie |
HUP0900281A2 (hu) * | 2009-05-05 | 2011-01-28 | Univ Szegedi | Kinurénsav-származékok, eljárás a vegyületek elõállítására, a vegyületeket tartalmazó gyógyászati készítmények és alkalmazásuk fejfájás kezelésére |
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CN103254127B (zh) * | 2013-05-28 | 2015-08-19 | 北京哈三联科技有限责任公司 | 甘氨酸重摄取抑制剂及其应用 |
WO2015138909A1 (en) | 2014-03-13 | 2015-09-17 | Proteostasis Therapeutics, Inc. | Compounds, compositions, and methods for increasing cftr activity |
CA2942387A1 (en) | 2014-03-13 | 2015-09-17 | Proteostasis Therapeutics, Inc. | Compounds, compositions and methods of increasing cftr actvity |
WO2015161011A1 (en) * | 2014-04-17 | 2015-10-22 | Merck Sharp & Dohme Corp. | Benzamide cgrp receptor antagonists |
CA2952862A1 (en) | 2014-06-19 | 2015-12-23 | Proteostasis Therapeutics, Inc. | Compounds, compositions and methods of increasing cftr activity |
CA2971855A1 (en) | 2014-12-23 | 2016-06-30 | Proteostasis Therapeutics, Inc. | Derivatives of 5-(hetero)arylpyrazol-3-carboxylic amide or 1-(hetero)aryltriazol-4-carboxylic amide useful for the treatment of inter alia cystic fibrosis |
US10344023B2 (en) | 2014-12-23 | 2019-07-09 | Proteostasis Therapeutics, Inc. | Derivatives of 3-heteroarylisoxazol-5-carboxylic amide useful for the treatment of inter alia cystic fibrosis |
MA41253A (fr) * | 2014-12-23 | 2017-10-31 | Proteostasis Therapeutics Inc | Composés, compositions et procédés pour augmenter l'activité du cftr |
US10392378B2 (en) | 2014-12-23 | 2019-08-27 | Proteostasis Therapeutics, Inc. | Derivatives of 5-phenyl- or 5-heteroarylathiazol-2-carboxylic amide useful for the treatment of inter alia cystic fibrosis |
AU2016297886B2 (en) | 2015-07-24 | 2020-12-10 | Proteostasis Therapeutics, Inc. | Compounds, compositions and methods of increasing CFTR activity |
JP6929276B2 (ja) | 2015-10-06 | 2021-09-01 | プロテオステイシス セラピューティクス,インコーポレイテッド | 化合物、医薬的に許容される塩又はその立体異性体及び医薬組成物 |
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US10899751B2 (en) | 2016-06-21 | 2021-01-26 | Proteostasis Therapeutics, Inc. | Compounds, compositions, and methods for increasing CFTR activity |
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IL117438A (en) * | 1995-03-16 | 2001-12-23 | Lilly Co Eli | Indazolecarboxamides, their preparation and pharmaceutical compositions containing them |
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- 2005-07-27 MX MX2007001225A patent/MX2007001225A/es not_active Application Discontinuation
- 2005-07-27 AU AU2005267930A patent/AU2005267930A1/en not_active Abandoned
- 2005-07-27 CA CA002576073A patent/CA2576073A1/en not_active Abandoned
- 2005-07-27 CN CNA2005800262910A patent/CN101014581A/zh active Pending
-
2007
- 2007-01-04 IL IL180546A patent/IL180546A0/en unknown
- 2007-01-24 ZA ZA200700685A patent/ZA200700685B/xx unknown
- 2007-02-28 NO NO20071137A patent/NO20071137L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
AU2005267930A1 (en) | 2006-02-09 |
CA2576073A1 (en) | 2006-02-09 |
MX2007001225A (es) | 2007-03-23 |
EP1781630A1 (en) | 2007-05-09 |
NO20071137L (no) | 2007-04-19 |
KR20070038136A (ko) | 2007-04-09 |
IL180546A0 (en) | 2007-06-03 |
CN101014581A (zh) | 2007-08-08 |
ZA200700685B (en) | 2008-09-25 |
WO2006014134A1 (en) | 2006-02-09 |
SE0401969D0 (sv) | 2004-08-02 |
JP2008508351A (ja) | 2008-03-21 |
BRPI0514036A (pt) | 2008-05-27 |
US20070191358A1 (en) | 2007-08-16 |
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