AR070993A1 - Derivados polisustituidos de 2-aril-6-fenil-imidazo[1,2-a]piridinas, composiciones farmaceuticas que los contienen, proceso de preparacion de los mismos, intermediarios de sintesis y uso de los mismos en el tratamiento o prevencion de enfermedades que implican receptores nucleares nurr-1, tales como - Google Patents
Derivados polisustituidos de 2-aril-6-fenil-imidazo[1,2-a]piridinas, composiciones farmaceuticas que los contienen, proceso de preparacion de los mismos, intermediarios de sintesis y uso de los mismos en el tratamiento o prevencion de enfermedades que implican receptores nucleares nurr-1, tales comoInfo
- Publication number
- AR070993A1 AR070993A1 ARP090100986A ARP090100986A AR070993A1 AR 070993 A1 AR070993 A1 AR 070993A1 AR P090100986 A ARP090100986 A AR P090100986A AR P090100986 A ARP090100986 A AR P090100986A AR 070993 A1 AR070993 A1 AR 070993A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- group
- aryl
- alkoxy
- nrarb
- Prior art date
Links
- 230000002265 prevention Effects 0.000 title 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 14
- 229910003827 NRaRb Inorganic materials 0.000 abstract 13
- 125000003118 aryl group Chemical group 0.000 abstract 12
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract 9
- 229910052736 halogen Inorganic materials 0.000 abstract 9
- 150000002367 halogens Chemical class 0.000 abstract 9
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 7
- 125000001424 substituent group Chemical group 0.000 abstract 7
- -1 -S (O) 2-C1-10 alkyl Chemical group 0.000 abstract 6
- 125000002947 alkylene group Chemical group 0.000 abstract 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 3
- 125000006557 (C2-C5) alkylene group Chemical group 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000005529 alkyleneoxy group Chemical group 0.000 abstract 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 abstract 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000004177 carbon cycle Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000004001 thioalkyl group Chemical group 0.000 abstract 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61P25/16—Anti-Parkinson drugs
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- General Chemical & Material Sciences (AREA)
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Abstract
Reivindicacion 1: Compuestos de la formula (1) en la que R1 representa un grupo fenilo o un grupo naftilo, pudiendo estar estos dos grupos opcionalmente sustituidos con uno o varios átomos o grupos elegidos independientemente los unos de los otros entre los átomos o grupos siguientes : halogeno, alquilo C1-10, haloalquilo C1-10, alcoxi C1-10, haloalcoxi C1-10, tioalquilo C1-10, -S(O)alquilo C1-10, -S(O)2-alquilo C1-10, hidroxilo, ciano, nitro, hidroxialquileno C1-10, NRaRb-alquileno C1-10, alcoxi C1-10-alquileno C1-10-oxi, NRaRb, CONRaRb, SO2NRaRb, NRcCORd, OC(O)NRaRb, OCO-alquilo C1-10, NRcC(O)ORe, NRcSO2Re, aril-alquileno C1-10, arilo o heteroarilo monocíclico, estando el arilo o el heteroarilo monocíclico eventualmente sustituido con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-10, halo-alquilo C1-10, alcoxi C1-10, halo-alcoxi C1-10, NRaRb, hidroxilo, oxo, nitro, ciano o OCO-alquilo C1-10; X representa de 1 a 4 sustituyentes idénticos o diferentes uno de otro, elegidos entre un hidrogeno, un halogeno, alquilo C1-10, alcoxi C1-10, NRaRb, ciano, nitro, pudiendo estar el alquilo C1-10 eventualmente sustituido con uno o varios grupos elegidos entre un halogeno, alcoxi C1-10, halo-alcoxi C1-10, NRaRb o hidroxilo; R representa en la posicion 3, 5, 7 u 8 de la imidazo[1,2-a]piridina de 1 a 4 sustituyentes idénticos o diferentes uno de otro, elegidos entre un halogeno, alquilo C1-10, halo-alquilo C1-10, alcoxi C1-10; R2 y R3 representan, independientemente uno de otro, un átomo de hidrogeno, un grupo alquilo C1-10, eventualmente sustituido con un grupo Rf; un grupo arilo, eventualmente sustituido con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-10, halo-alquilo C1-10, alcoxi C1-10, halo-alcoxi C1-10, NRaRb, hidroxilo, nitro o ciano; R2 y X pueden formar junto con los átomos de carbono a los que están unidos un ciclo carbonado de 5 a 7 átomos de carbono; R4 representa: un átomo de hidrogeno, un grupo alquilo C1-10, eventualmente sustituido con un grupo Rf; un grupo arilo, eventualmente sustituido con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-10, halo-alquilo C1-10, alcoxi C1-10, halo-alcoxi C1-10, NRaRb, hidroxilo, nitro, ciano, alquil C1-10-(CO)-, CONRaRb, NRcCORd, OC(O)NRaRb, OCO-alquilo C1-10, NRcC(O)ORe o arilo, estando el arilo eventualmente sustituido con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-10, halo-alquilo C1-10, alcoxi C1-10, halo-alcoxi C1-10, NRaRb, hidroxilo, nitro o ciano; Ra y Rb representan, independientemente uno de otro, un átomo de hidrogeno o un grupo alquilo C1-10, aril-alquileno C1-10 o arilo; o Ra y Rb forman conjuntamente, con el átomo de nitrogeno que les lleva, un grupo azetidina, pirrolidina, piperidina, azepina, morfolina, tiomorfolina, piperazina, homopiperazina, estando este grupo eventualmente sustituido con un grupo alquilo C1-10, arilo o aril-alquileno C1-10; Rc y Rd representan, independientemente uno de otro, un átomo de hidrogeno o un grupo alquilo C1-10, aril-alquileno C1-10, arilo; o Rc y Rd forman juntos un grupo alquileno C2-5; Re representa un grupo alquilo C1-10, aril-alquileno C1-10, arilo; o Rc y Re forman juntos un grupo alquileno C2-5; Rf representa un átomo de halogeno, un grupo alcoxi C1-10, halo-alcoxi C1-10, hidroxilo, ciano, NRaRb, C(O)NRaRb, NRcCORd, OC(O)NRaRb, OCO-alquilo C1-10, NRcCOORe, SO2NRaRb, NRcSO2Re, aril-alquileno C1-10, arilo, estando el arilo eventualmente sustituido con uno o varios sustituyentes elegidos entre un halogeno, un grupo alquilo C1-10, halo-alquilo C1-10, alcoxi C1-10, halo-alcoxi C1-10, NRaRb, hidroxilo, nitro, ciano o OCO-alquilo C1-10; en forma de base o de sal de adicion a un ácido.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0801581A FR2928922B1 (fr) | 2008-03-21 | 2008-03-21 | Derives de 2-aryl-6-phenyl-imidazo°1,2-a!pyridines polysubstitues, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR070993A1 true AR070993A1 (es) | 2010-05-19 |
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ID=39764952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090100986A AR070993A1 (es) | 2008-03-21 | 2009-03-19 | Derivados polisustituidos de 2-aril-6-fenil-imidazo[1,2-a]piridinas, composiciones farmaceuticas que los contienen, proceso de preparacion de los mismos, intermediarios de sintesis y uso de los mismos en el tratamiento o prevencion de enfermedades que implican receptores nucleares nurr-1, tales como |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US8507520B2 (es) |
| EP (1) | EP2262769B1 (es) |
| JP (1) | JP5508385B2 (es) |
| KR (1) | KR20100129775A (es) |
| CN (2) | CN102036959B (es) |
| AR (1) | AR070993A1 (es) |
| AU (1) | AU2009253234B2 (es) |
| BR (1) | BRPI0909415A2 (es) |
| CA (1) | CA2719125C (es) |
| CL (1) | CL2009000696A1 (es) |
| CO (1) | CO6290657A2 (es) |
| EA (1) | EA201071112A1 (es) |
| FR (1) | FR2928922B1 (es) |
| IL (1) | IL208246A0 (es) |
| MA (1) | MA32247B1 (es) |
| ME (1) | ME01029B (es) |
| MX (1) | MX2010010316A (es) |
| NZ (1) | NZ588151A (es) |
| SG (1) | SG189679A1 (es) |
| TW (1) | TW200944202A (es) |
| UY (1) | UY31728A (es) |
| WO (1) | WO2009144394A1 (es) |
| ZA (1) | ZA201006728B (es) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8426441B2 (en) * | 2007-12-14 | 2013-04-23 | Roche Palo Alto Llc | Inhibitors of bruton's tyrosine kinase |
| FR2928921B1 (fr) * | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 2-aryl-6-phenyl-imidazo°1,2-a!pyridines, leur preparation et leur application en therapeutique |
| FR2928923B1 (fr) * | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 2-heteroaryl-6-phenyl-imidazo °1,2-a!pyridines, leur preparation et leur application en therapeutiques |
| FR2928924B1 (fr) | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 6-heteroaryle-imidazo°1,2-a! pyridines, leur preparation et leur application en therapeutique |
| FR2950344B1 (fr) * | 2009-09-18 | 2011-11-25 | Sanofi Aventis | Derives de 5-phenyl-pyrazolopyridine, leur preparation et leur aplication en therapeutique. |
| FR2950345B1 (fr) * | 2009-09-18 | 2011-09-23 | Sanofi Aventis | Derives acetyleniques de 5-phenyl-pyrazolopyridine, leur preparation et leur application en therapeutique |
| US9295384B2 (en) * | 2014-05-16 | 2016-03-29 | Novartis Ag | Imaging probes and associated devices, systems, and methods utilizing lever arm actuators |
| MX2018003903A (es) * | 2015-09-29 | 2018-09-21 | Oncotherapy Science Inc | Compuesto biciclico y uso del mismo para inhibicion de suv39h2. |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| MD3377488T2 (ro) | 2015-11-19 | 2023-02-28 | Incyte Corp | Compuși heterociclici ca imunomodulatori |
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| CN106906486B (zh) * | 2017-02-22 | 2018-12-11 | 华南理工大学 | 3-溴-2-苯基-咪唑并[1,2-α]吡啶类衍生物的电化学合成方法 |
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| MX2020010321A (es) | 2018-03-30 | 2021-01-08 | Incyte Corp | Compuestos heterociclicos como inmunomoduladores. |
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| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
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|---|---|---|---|---|
| DE60039782D1 (de) * | 1999-12-06 | 2008-09-18 | Ajinomoto Kk | Amidinophenylbrenztraubensäure-derivat |
| NZ541861A (en) | 2003-02-26 | 2009-05-31 | Sugen Inc | Aminoheteroaryl compounds as protein kinase inhibitors |
| FR2903106B1 (fr) * | 2006-07-03 | 2010-07-30 | Sanofi Aventis | Utilisations de 2-benzoyl-imidazopyridines en therapeutique |
| FR2903105A1 (fr) * | 2006-07-03 | 2008-01-04 | Sanofi Aventis Sa | Derives de 2-benzoyl-imidazopyridines, leur preparation et leur application en therapeutique |
| FR2903107B1 (fr) * | 2006-07-03 | 2008-08-22 | Sanofi Aventis Sa | Derives d'imidazopyridine-2-carboxamides, leur preparation et leur application en therapeutique |
| FR2906250B1 (fr) * | 2006-09-22 | 2008-10-31 | Sanofi Aventis Sa | Derives de 2-aryl-6phenyl-imidazo(1,2-a) pyridines, leur preparation et leur application en therapeutique |
| FR2928923B1 (fr) * | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 2-heteroaryl-6-phenyl-imidazo °1,2-a!pyridines, leur preparation et leur application en therapeutiques |
| FR2928924B1 (fr) * | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 6-heteroaryle-imidazo°1,2-a! pyridines, leur preparation et leur application en therapeutique |
| FR2928921B1 (fr) * | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 2-aryl-6-phenyl-imidazo°1,2-a!pyridines, leur preparation et leur application en therapeutique |
-
2008
- 2008-03-21 FR FR0801581A patent/FR2928922B1/fr active Active
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2009
- 2009-03-19 AR ARP090100986A patent/AR070993A1/es not_active Application Discontinuation
- 2009-03-20 TW TW098109257A patent/TW200944202A/zh unknown
- 2009-03-20 NZ NZ588151A patent/NZ588151A/en not_active IP Right Cessation
- 2009-03-20 KR KR1020107023411A patent/KR20100129775A/ko not_active Application Discontinuation
- 2009-03-20 CA CA2719125A patent/CA2719125C/fr not_active Expired - Fee Related
- 2009-03-20 ME MEP-2010-155A patent/ME01029B/me unknown
- 2009-03-20 WO PCT/FR2009/000302 patent/WO2009144394A1/fr active Application Filing
- 2009-03-20 JP JP2011500261A patent/JP5508385B2/ja not_active Expired - Fee Related
- 2009-03-20 SG SG2013016563A patent/SG189679A1/en unknown
- 2009-03-20 UY UY0001031728A patent/UY31728A/es not_active Application Discontinuation
- 2009-03-20 CN CN2009801183168A patent/CN102036959B/zh not_active Expired - Fee Related
- 2009-03-20 EP EP09754044.7A patent/EP2262769B1/fr active Active
- 2009-03-20 CN CN201310047398XA patent/CN103193815A/zh active Pending
- 2009-03-20 AU AU2009253234A patent/AU2009253234B2/en not_active Ceased
- 2009-03-20 EA EA201071112A patent/EA201071112A1/ru unknown
- 2009-03-20 CL CL2009000696A patent/CL2009000696A1/es unknown
- 2009-03-20 BR BRPI0909415A patent/BRPI0909415A2/pt not_active IP Right Cessation
- 2009-03-20 MX MX2010010316A patent/MX2010010316A/es active IP Right Grant
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- 2010-09-19 IL IL208246A patent/IL208246A0/en unknown
- 2010-09-20 ZA ZA2010/06728A patent/ZA201006728B/en unknown
- 2010-09-21 CO CO10116849A patent/CO6290657A2/es not_active Application Discontinuation
- 2010-10-19 MA MA33273A patent/MA32247B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2928922A1 (fr) | 2009-09-25 |
| EP2262769B1 (fr) | 2014-11-05 |
| CO6290657A2 (es) | 2011-06-20 |
| JP5508385B2 (ja) | 2014-05-28 |
| CL2009000696A1 (es) | 2010-08-13 |
| NZ588151A (en) | 2012-07-27 |
| CA2719125A1 (fr) | 2009-12-03 |
| TW200944202A (en) | 2009-11-01 |
| KR20100129775A (ko) | 2010-12-09 |
| BRPI0909415A2 (pt) | 2019-01-15 |
| EP2262769A1 (fr) | 2010-12-22 |
| CN102036959A (zh) | 2011-04-27 |
| US20110065745A1 (en) | 2011-03-17 |
| CN102036959B (zh) | 2013-05-22 |
| WO2009144394A1 (fr) | 2009-12-03 |
| AU2009253234A1 (en) | 2009-12-03 |
| CN103193815A (zh) | 2013-07-10 |
| WO2009144394A8 (fr) | 2010-10-14 |
| ZA201006728B (en) | 2011-11-30 |
| CA2719125C (fr) | 2016-07-26 |
| MX2010010316A (es) | 2010-12-14 |
| MA32247B1 (fr) | 2011-04-01 |
| IL208246A0 (en) | 2010-12-30 |
| EA201071112A1 (ru) | 2011-04-29 |
| FR2928922B1 (fr) | 2010-04-23 |
| AU2009253234B2 (en) | 2013-07-11 |
| UY31728A (es) | 2009-11-10 |
| US8507520B2 (en) | 2013-08-13 |
| ME01029B (me) | 2012-10-20 |
| JP2011515382A (ja) | 2011-05-19 |
| SG189679A1 (en) | 2013-05-31 |
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