KR20060009900A - 피페리디닐- 및 피페라지닐-알킬 카르바메이트 유도체,그의 제조 방법 및 그의 치료 용도 - Google Patents
피페리디닐- 및 피페라지닐-알킬 카르바메이트 유도체,그의 제조 방법 및 그의 치료 용도 Download PDFInfo
- Publication number
- KR20060009900A KR20060009900A KR1020057021049A KR20057021049A KR20060009900A KR 20060009900 A KR20060009900 A KR 20060009900A KR 1020057021049 A KR1020057021049 A KR 1020057021049A KR 20057021049 A KR20057021049 A KR 20057021049A KR 20060009900 A KR20060009900 A KR 20060009900A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- formula
- alkyl
- piperidyl
- mmol
- 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.)
- Abandoned
Links
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- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 18
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- -1 tetrahydroquinolyl Chemical group 0.000 claims description 110
- 238000000034 method Methods 0.000 claims description 70
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
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- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 9
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 9
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 9
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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- 125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 5
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- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
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- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
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- 230000001684 chronic effect Effects 0.000 claims description 3
- 150000001475 oxazolidinediones Chemical class 0.000 claims description 3
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- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- NOEGRVOHYGKMHT-UHFFFAOYSA-N 3-[1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-1,3-oxazolidine-2,4-dione Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1N1C(=O)COC1=O NOEGRVOHYGKMHT-UHFFFAOYSA-N 0.000 claims description 2
- XPHGCWXJSOTHHH-UHFFFAOYSA-N 3-[1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-5-ethyl-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(CC)OC(=O)N1C1CCN(C=2N=C3C=C(OC)C(OC)=CC3=C(N)N=2)CC1 XPHGCWXJSOTHHH-UHFFFAOYSA-N 0.000 claims description 2
- UQJGRIHEZMCSAF-UHFFFAOYSA-N 3-[1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-5-methyl-1,3-oxazolidine-2,4-dione Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1N1C(=O)OC(C)C1=O UQJGRIHEZMCSAF-UHFFFAOYSA-N 0.000 claims description 2
- PJQQQARPNFVEFZ-UHFFFAOYSA-N 3-[1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-5-propan-2-yl-1,3-oxazolidine-2,4-dione Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1N1C(=O)OC(C(C)C)C1=O PJQQQARPNFVEFZ-UHFFFAOYSA-N 0.000 claims description 2
- YNNPNUSPBVGJDW-UHFFFAOYSA-N 3-[1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-5-propyl-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(CCC)OC(=O)N1C1CCN(C=2N=C3C=C(OC)C(OC)=CC3=C(N)N=2)CC1 YNNPNUSPBVGJDW-UHFFFAOYSA-N 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
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- 208000030814 Eating disease Diseases 0.000 claims description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
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- 101000918494 Homo sapiens Fatty-acid amide hydrolase 1 Proteins 0.000 claims 1
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- 125000005348 fluorocycloalkyl group Chemical group 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 125000001072 heteroaryl group Chemical class 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
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- 238000010898 silica gel chromatography Methods 0.000 description 42
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| FR0305540A FR2854633B1 (fr) | 2003-05-07 | 2003-05-07 | Derives de piperidinyl-et piperazinyl-alkylcarbamates, leur preparation et leur application en therapeutique |
| FR03/05540 | 2003-05-07 |
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| KR20060009900A true KR20060009900A (ko) | 2006-02-01 |
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| KR1020057021049A Abandoned KR20060009900A (ko) | 2003-05-07 | 2004-05-06 | 피페리디닐- 및 피페라지닐-알킬 카르바메이트 유도체,그의 제조 방법 및 그의 치료 용도 |
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| TW (1) | TWI337607B (enExample) |
| UA (1) | UA81808C2 (enExample) |
| WO (1) | WO2004099176A1 (enExample) |
| ZA (1) | ZA200508158B (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB2397067B (en) * | 2002-12-23 | 2005-05-11 | Destiny Pharma Ltd | Porphin & azaporphin derivatives with at least one cationic-nitrogen-containing meso-substituent for use in photodynamic therapy & in vitro sterilisation |
| FR2864080B1 (fr) * | 2003-12-23 | 2006-02-03 | Sanofi Synthelabo | Derives de 1-piperazine-et-1-homopiperazine-carboxylates, leur preparation et leur application en therapeutique |
| FR2866884B1 (fr) * | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives d'aryl-et d'heteroaryl-piperidinecarboxylates, leur preparation et leur application en therapeutique |
| FR2866888B1 (fr) | 2004-02-26 | 2006-05-05 | Sanofi Synthelabo | Derives de alkylpiperazine- et alkylhomopiperazine- carboxylates, leur preparation et leur application en therapeutique |
| FR2866886B1 (fr) * | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives d'aryl-et d'heteroaryl-akylcarbamates, leur preparation et leur application en therapeutique |
| FR2866885B1 (fr) | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives de piperidinylalkylcarbamates, leur prepation et leur application en therapeutique |
| GB2415372A (en) | 2004-06-23 | 2005-12-28 | Destiny Pharma Ltd | Non photodynamical or sonodynamical antimicrobial use of porphyrins and azaporphyrins containing at least one cationic-nitrogen-containing substituent |
| TW200633990A (en) | 2004-11-18 | 2006-10-01 | Takeda Pharmaceuticals Co | Amide compound |
| EP2937341B1 (en) | 2004-12-30 | 2017-07-05 | Janssen Pharmaceutica N.V. | 4-(benzyl)-piperazine-1-carboxylic acid phenylamide derivatives and related compounds as modulators of fatty acid amide hydrolase (faah) for the treatment of anxiety, pain and other conditions |
| FR2885364B1 (fr) * | 2005-05-03 | 2007-06-29 | Sanofi Aventis Sa | Derives d'alkyl-, alkenyl-et alkynylcarbamates, leur preparation et leur application en therapeutique |
| US7541359B2 (en) | 2005-06-30 | 2009-06-02 | Janssen Pharmaceutica N.V. | N-heteroarylpiperazinyl ureas as modulators of fatty acid amide hydrolase |
| WO2008030752A2 (en) * | 2006-09-07 | 2008-03-13 | N.V. Organon | Methods for determining effective doses of fatty acid amide hydrolase inhibitors in vivo |
| EP1903037A1 (de) * | 2006-09-07 | 2008-03-26 | Bayer Schering Pharma Aktiengesellschaft | 1-(Het)aryl-3-[hetaryl-piperidin-4-yl]-thioharnstoffe als Modulatoren des EP2-Rezeptors |
| WO2008042892A2 (en) * | 2006-10-02 | 2008-04-10 | N.V. Organon | Fatty acid amide hydrolase inhibitors for energy metabolism disorders |
| US20080119549A1 (en) * | 2006-11-20 | 2008-05-22 | N.V. Organon | Metabolically-stabilized inhibitors of fatty acid amide hydrolase |
| TWI434842B (zh) * | 2008-07-14 | 2014-04-21 | Astellas Pharma Inc | Azole compounds |
| FR2934265B1 (fr) * | 2008-07-23 | 2010-07-30 | Sanofi Aventis | Derives de carbamates d'alkylthiazoles, leur preparation et leur application en therapeutique |
| FR2938537B1 (fr) * | 2008-11-14 | 2012-10-26 | Sanofi Aventis | Derives de carbamates d'alkyl-heterocycles, leur preparation et leur application en therapeutique. |
| FR2941696B1 (fr) * | 2009-02-05 | 2011-04-15 | Sanofi Aventis | Derives d'azaspiranyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique |
| EP2421848A1 (en) * | 2009-04-22 | 2012-02-29 | Janssen Pharmaceutica N.V. | Azetidinyl diamides as monoacylglycerol lipase inhibitors |
| FR2945531A1 (fr) * | 2009-05-12 | 2010-11-19 | Sanofi Aventis | Derives de 7-aza-spiro°3,5!nonane-7-carboxylates, leur preparation et leur application en therapeutique |
| US20120028931A1 (en) * | 2009-09-14 | 2012-02-02 | Recordati Ireland Limited | Heterocyclic m-glu5 antagonists |
| WO2011085216A2 (en) | 2010-01-08 | 2011-07-14 | Ironwood Pharmaceuticals, Inc. | Use of faah inhibitors for treating parkinson's disease and restless legs syndrome |
| US20130224151A1 (en) | 2010-03-31 | 2013-08-29 | United States Of America | Use of FAAH Inhibitors for Treating Abdominal, Visceral and Pelvic Pain |
| UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
| GB201017345D0 (en) | 2010-10-14 | 2010-11-24 | Proximagen Ltd | Receptor antagonists |
| MX350788B (es) * | 2012-01-06 | 2017-09-13 | Abide Therapeutics Inc | Compuestos de carbamato y preparación y uso de los mismos. |
| DE102012018115A1 (de) | 2012-09-13 | 2014-03-13 | Matthias Lehr | Aryl-N-(arylalkyl)carbamate als Hemmstoffe der Fatty Acid Amide Hydrolase |
| EP3022179B1 (en) | 2013-07-18 | 2017-11-15 | Fondazione Istituto Italiano Di Tecnologia | Phenyl carbamates and their use as inhibitors of the fatty acid amide hydrolase (faah) enzyme and modulators of the d3 dopamine receptor (d3dr) |
| DE102013016573A1 (de) | 2013-10-04 | 2015-04-09 | Matthias Lehr | 1-Tetrazolylpropan-2-one als Inhibitoren von cytosolischer Phospholipase A2 und Fatty Acid Amide Hydrolase, insbesondere geeignet zur topischen Anwendung |
| JP6927882B2 (ja) | 2015-04-02 | 2021-09-01 | プロキシマジェン,リミティド ライアビリティ カンパニー | 癌の新治療法 |
| JP2023550153A (ja) * | 2020-11-23 | 2023-11-30 | エフ. ホフマン-ラ ロシュ アーゲー | B型肝炎ウイルス感染症の処置および予防のためのn-[(1,3-ベンゾオキサゾル-2-イル)-複素環]アミド誘導体 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3235565A1 (de) * | 1982-09-25 | 1984-03-29 | Boehringer Ingelheim KG, 6507 Ingelheim | Piperidinderivate, ihre herstellung und verwendung |
| FR2761266B1 (fr) * | 1997-03-28 | 1999-07-02 | Sanofi Sa | Composition pharmaceutique formee par granulation humide pour l'administration orale d'un derive du n-piperidino-3- pyrazolecarboxamide, de ses sels et de leurs solvates |
| FR2783246B1 (fr) * | 1998-09-11 | 2000-11-17 | Aventis Pharma Sa | Derives d'azetidine, leur preparation et les medicaments les contenant |
| FR2805818B1 (fr) * | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Derives d'azetidine, leur preparation et les compositions pharmaceutiques les contenant |
| FR2816938B1 (fr) | 2000-11-22 | 2003-01-03 | Sanofi Synthelabo | Derives de 3-aroylindole, leur procede de preparation et les compositions pharmaceutiques en contenant |
| FR2843964B1 (fr) * | 2002-08-29 | 2004-10-01 | Sanofi Synthelabo | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
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