OA13154A - Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them. - Google Patents
Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them. Download PDFInfo
- Publication number
- OA13154A OA13154A OA1200500280A OA1200500280A OA13154A OA 13154 A OA13154 A OA 13154A OA 1200500280 A OA1200500280 A OA 1200500280A OA 1200500280 A OA1200500280 A OA 1200500280A OA 13154 A OA13154 A OA 13154A
- Authority
- OA
- OAPI
- Prior art keywords
- substituted
- unsubstituted
- dibenzo
- carboxamide
- furan
- Prior art date
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 26
- 230000002757 inflammatory effect Effects 0.000 title claims description 14
- 208000010668 atopic eczema Diseases 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 11
- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 8
- 230000008569 process Effects 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 2
- 230000000172 allergic effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 16
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 13
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- 150000001875 compounds Chemical class 0.000 claims description 158
- -1 -OH Chemical group 0.000 claims description 74
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 36
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
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- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- IPEMCIBPDYCJLO-UHFFFAOYSA-N 5-[(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)methyl]-n-(2,4,6-trimethoxyphenyl)furan-2-carboxamide Chemical compound COC1=CC(OC)=CC(OC)=C1NC(=O)C(O1)=CC=C1CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C IPEMCIBPDYCJLO-UHFFFAOYSA-N 0.000 claims description 19
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- 230000006433 tumor necrosis factor production Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
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- 230000002485 urinary effect Effects 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7238725B2 (en) * | 2002-10-23 | 2007-07-03 | Glenmark Pharmaceuticals Ltd. | Tricyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them |
| PL378813A1 (pl) * | 2003-04-11 | 2006-05-29 | Glenmark Pharmaceuticals S.A. | Nowe związki heterocykliczne przydatne w leczeniu stanów zapalnych i zaburzeń alergicznych: sposób ich wytwarzania i kompozycje farmaceutyczne zawierające te związki |
| MX2007004400A (es) | 2004-10-13 | 2007-06-19 | Glenmark Pharmaceuticals Sa | Procedimiento para la preparacion de n-(3,5-dicloropirid-a-il)-4- ifluorometoxi-8-metanosulfonamido-dibenzo [b,d] difuran-1-carboxamida. |
| WO2006051390A1 (en) * | 2004-11-10 | 2006-05-18 | Glenmark Pharmaceuticals S.A. | Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders, pharmaceutical compositions containing them, and methods of preparing them |
| US7943634B2 (en) | 2004-12-17 | 2011-05-17 | Glenmark Pharmaceuticals S.A. | Substituted benzo[4,5]furo[3,2-c]pyridine derivatives as PDE 4 inhibitors |
| EA014956B1 (ru) * | 2004-12-17 | 2011-04-29 | ГЛЕНМАРК ФАРМАСЬЮТИКАЛС Эс.Эй. | Гетероциклические соединения, применяемые для лечения воспалительных и аллергических нарушений |
| US8119655B2 (en) * | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| RS53084B (sr) | 2006-07-05 | 2014-06-30 | Takeda Gmbh | Kombinacija inhibitora hmg-coa reduktaze rosuvastatina sa inhibitorom fosfodiesteraze 4, kao što je roflumilast, roflumilast-n-oksid za lečenje inflamatornih plućnih obolenja |
| WO2008005955A2 (en) * | 2006-07-06 | 2008-01-10 | Forest Laboratories Holdings Limited | Synthesis of heterocyclic compounds |
| CA2661850A1 (en) * | 2006-09-01 | 2008-03-06 | Kyorin Pharmaceutical Co., Ltd. | Pyrazolopyridine carboxamide derivative and phosphodiesterase (pde) inhibitor containing the same |
| WO2008029829A1 (en) * | 2006-09-06 | 2008-03-13 | Kyorin Pharmaceutical Co., Ltd. | Pyrazolopyridine derivative and phosphodiesterase (pde) inhibitor containing the same as active ingredient |
| US8263648B2 (en) * | 2006-09-11 | 2012-09-11 | Mylan Laboratories Ltd. | Diebenzofuran derivatives as inhibitors of PDE-4 and PDE-10 |
| WO2008057254A2 (en) * | 2006-10-27 | 2008-05-15 | Wyeth | Tricyclic compounds as matrix metalloproteinase inhibitors |
| WO2008065522A2 (en) * | 2006-11-29 | 2008-06-05 | Glenmark Pharmaceuticals S.A. | Process for the synthesis of 4-difluoromethoxy-8-nitro-1-formyl dibenzo[b,d] furan-an intermediate for pde iv inhibitors |
| US20100098641A1 (en) * | 2006-12-13 | 2010-04-22 | William Baker | Monophosphates as Mutual Prodrugs of Anti-Inflammatory Signal Transduction Modulators (AISTM's) and Beta-Agonists for the Treatment of Pulmonary Inflammation and Bronchoconstriction |
| MX2009008463A (es) * | 2007-02-09 | 2010-01-27 | Forest Lab Holdings Ltd | Formulaciones biodisponibles de compuestos heterociclicos. |
| US8524905B2 (en) | 2007-05-22 | 2013-09-03 | Glenmark Pharmaceuticals S.A. | Processes for preparing 6-(difluoromethoxy)[1]benzofuro[3,2-c]pyridine-9-carbaldehyde, a novel intermediate for the synthesis of PDE IV inhibitors |
| US20110171195A1 (en) * | 2007-06-15 | 2011-07-14 | Duke University | Methods and compositions for treating urinary tract infections using agents that mimic or elevate cyclic amp |
| EP2070913A1 (de) | 2007-12-14 | 2009-06-17 | CHIESI FARMACEUTICI S.p.A. | Ester-Derivate als Phosphodiesterase-Hemmer |
| WO2009147476A1 (en) * | 2008-06-02 | 2009-12-10 | Matrix Laboratories Ltd. | Novel pde inhibitors, pharmaceutical compositions containing them and processes for their preparation |
| TWI474282B (zh) * | 2008-10-03 | 2015-02-21 | Himax Tech Ltd | 深度相關的影像加強 |
| BRPI0922565A2 (pt) | 2008-12-19 | 2015-12-15 | Bristol Myers Squibb Co | compostos de carbazol carboxamida úteis como inibidores de cinase |
| WO2011132051A2 (en) * | 2010-04-19 | 2011-10-27 | Glenmark Pharmaceuticals S.A. | Tricycle compounds as phosphodiesterase-10 inhibitors |
| LT2651965T (lt) * | 2010-12-15 | 2019-01-10 | Contravir Pharmaceuticals, Inc. | Ciklosporino analogo molekulės su modifikuotomis 1 ir 3 aminorūgštimis |
| JP6225161B2 (ja) * | 2013-02-28 | 2017-11-01 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 呼吸器疾患の予防治療剤 |
| CN104177612A (zh) * | 2013-05-28 | 2014-12-03 | 韩文毅 | 一种新的非线性聚合物及其制备和用途 |
| CN104211947A (zh) * | 2013-05-31 | 2014-12-17 | 韩文毅 | 一种非线性聚合物及其制备和用途 |
| CN104211950A (zh) * | 2013-06-04 | 2014-12-17 | 韩文毅 | 一种非线性聚合物及其制备与用途 |
| CN104211949A (zh) * | 2013-06-04 | 2014-12-17 | 韩文毅 | 一种非线性聚合物及其制备与用途 |
| US20170107216A1 (en) | 2015-10-19 | 2017-04-20 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| AU2016358100B2 (en) | 2015-11-19 | 2021-05-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| TW201726623A (zh) | 2015-12-17 | 2017-08-01 | 英塞特公司 | 作為免疫調節劑之雜環化合物 |
| TWI850624B (zh) | 2015-12-22 | 2024-08-01 | 美商英塞特公司 | 作為免疫調節劑之雜環化合物 |
| RU2616617C1 (ru) * | 2016-04-12 | 2017-04-18 | Федеральное государственное бюджетное учреждение науки Институт органического синтеза им. И.Я. Постовского Уральского отделения Российской академии наук | 5-(9-этил-9Н-карбазол-3-ил)-4-[5-(9-этил-9Н-карбазол-3-ил)-тиофен-2-ил]-пиримидин |
| TW201808950A (zh) | 2016-05-06 | 2018-03-16 | 英塞特公司 | 作為免疫調節劑之雜環化合物 |
| US20170342060A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| DK3472167T3 (da) | 2016-06-20 | 2022-09-05 | Incyte Corp | Heterocykliske forbindelser som immunomodulatorer |
| EP3484866B1 (de) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclische verbindungen als immunmodulatoren |
| EP3504198B1 (de) | 2016-08-29 | 2023-01-25 | Incyte Corporation | Heterocyclische verbindungen als immunmodulatoren |
| ES2874756T3 (es) | 2016-12-22 | 2021-11-05 | Incyte Corp | Derivados de triazolo[1,5-A]piridina como inmunomoduladores |
| EP3558963B1 (de) | 2016-12-22 | 2022-03-23 | Incyte Corporation | Bicyclische heteroaromatische verbindungen als immunmodulatoren |
| IL295660A (en) | 2016-12-22 | 2022-10-01 | Incyte Corp | Benzooxazole derivatives as immunomodulators |
| EP3558973B1 (de) | 2016-12-22 | 2021-09-15 | Incyte Corporation | Pyridinderivate als immunmodulatoren |
| RS64055B1 (sr) | 2018-03-30 | 2023-04-28 | Incyte Corp | Heterociklična jedinjenja kao imunomodulatori |
| EP4219492B1 (de) | 2018-05-11 | 2024-11-27 | Incyte Corporation | Heterocyclische verbindungen als immunmodulatoren |
| CN109651232A (zh) * | 2018-12-12 | 2019-04-19 | 河北华清光电材料有限公司 | 制备4-溴咔唑及其衍生物的方法 |
| JP7665593B2 (ja) | 2019-08-09 | 2025-04-21 | インサイト・コーポレイション | Pd-1/pd-l1阻害剤の塩 |
| EP4037773A1 (de) | 2019-09-30 | 2022-08-10 | Incyte Corporation | Pyrido[3,2-d]pyrimidin-verbindungen als immunmodulatoren |
| BR112022009031A2 (pt) | 2019-11-11 | 2022-10-11 | Incyte Corp | Sais e formas cristalinas de um inibidor de pd-1/pd-l1 |
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| GB1041861A (en) | 1962-03-14 | 1966-09-07 | Organon Labor Ltd | Pyrrolidone derivatives and pharmaceutical preparations containing them |
| US3759948A (en) * | 1969-06-25 | 1973-09-18 | Merck & Co Inc | Non-steroid anti-inflammatory compounds |
| NL7008628A (de) * | 1969-06-25 | 1970-12-29 | ||
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- 2004-04-09 US US10/821,642 patent/US7223789B2/en not_active Expired - Lifetime
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