JP2011515381A5 - - Google Patents
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- Publication number
- JP2011515381A5 JP2011515381A5 JP2011500259A JP2011500259A JP2011515381A5 JP 2011515381 A5 JP2011515381 A5 JP 2011515381A5 JP 2011500259 A JP2011500259 A JP 2011500259A JP 2011500259 A JP2011500259 A JP 2011500259A JP 2011515381 A5 JP2011515381 A5 JP 2011515381A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- methanol
- imidazo
- thien
- furan
- 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.)
- Granted
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- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 260
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 140
- -1 CONRaRb Inorganic materials 0.000 claims 69
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 40
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 39
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 36
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 32
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 21
- 229910003827 NRaRb Inorganic materials 0.000 claims 19
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 18
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 12
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 9
- 150000003840 hydrochlorides Chemical class 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 238000002360 preparation method Methods 0.000 claims 7
- 230000002265 prevention Effects 0.000 claims 7
- 125000004429 atom Chemical group 0.000 claims 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 claims 5
- 125000002541 furyl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 238000003786 synthesis reaction Methods 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 3
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 3
- 229940047889 isobutyramide Drugs 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000006557 (C2-C5) alkylene group Chemical group 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000003927 aminopyridines Chemical class 0.000 claims 2
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 150000001638 boron Chemical class 0.000 claims 2
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 claims 2
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004001 thioalkyl group Chemical group 0.000 claims 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical class [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000034799 Tauopathies Diseases 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005529 alkyleneoxy group Chemical group 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 229960003966 nicotinamide Drugs 0.000 claims 1
- 235000005152 nicotinamide Nutrition 0.000 claims 1
- 239000011570 nicotinamide Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 201000006152 substance dependence Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 claims 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 Cc1nc(Cl)c[n]1C=C(*)C=C* Chemical compound Cc1nc(Cl)c[n]1C=C(*)C=C* 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0801585 | 2008-03-21 | ||
| FR0801585A FR2928924B1 (fr) | 2008-03-21 | 2008-03-21 | Derives polysubstitues de 6-heteroaryle-imidazo°1,2-a! pyridines, leur preparation et leur application en therapeutique |
| PCT/FR2009/000298 WO2009144392A1 (fr) | 2008-03-21 | 2009-03-20 | DÉRIVÉS POLYSUBSTITUES DE 6-HETEROARYLE-IMIDAZO[1,2-α]PYRIDINES, LEUR PRÉPARATION ET LEUR APPLICATION EN THÉRAPEUTIQUE |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011515381A JP2011515381A (ja) | 2011-05-19 |
| JP2011515381A5 true JP2011515381A5 (https=) | 2012-03-08 |
| JP5508384B2 JP5508384B2 (ja) | 2014-05-28 |
Family
ID=39764971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011500259A Expired - Fee Related JP5508384B2 (ja) | 2008-03-21 | 2009-03-20 | ６−ヘテロアリールイミダゾ［ｌ，２−ａ］−ピリジンの多置換誘導体、並びにこれらの調製および治療的使用 |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US8088765B2 (https=) |
| EP (1) | EP2262804B1 (https=) |
| JP (1) | JP5508384B2 (https=) |
| KR (1) | KR20100124830A (https=) |
| CN (2) | CN103145747B (https=) |
| AR (1) | AR070995A1 (https=) |
| AU (1) | AU2009253232B2 (https=) |
| BR (1) | BRPI0910309A2 (https=) |
| CA (1) | CA2719118C (https=) |
| CL (1) | CL2009000699A1 (https=) |
| CO (1) | CO6300864A2 (https=) |
| EA (1) | EA201071111A1 (https=) |
| FR (1) | FR2928924B1 (https=) |
| IL (1) | IL208247A0 (https=) |
| MA (1) | MA32248B1 (https=) |
| ME (1) | ME01112B (https=) |
| MX (1) | MX2010010268A (https=) |
| NZ (1) | NZ588083A (https=) |
| PE (1) | PE20091694A1 (https=) |
| PH (1) | PH12012501817A1 (https=) |
| TW (1) | TW200942541A (https=) |
| UY (1) | UY31730A (https=) |
| WO (1) | WO2009144392A1 (https=) |
| ZA (1) | ZA201006725B (https=) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2928922B1 (fr) * | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives de 2-aryl-6-phenyl-imidazo°1,2-a!pyridines polysubstitues, 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 |
| BRPI0914772A2 (pt) | 2008-06-25 | 2015-10-20 | Envivo Pharmaceuticals Inc | compostos heterocíclicos 1,2-dissubstituídos |
| TWI453207B (zh) * | 2008-09-08 | 2014-09-21 | Signal Pharm Llc | 胺基三唑并吡啶，其組合物及使用其之治療方法 |
| CN105125547A (zh) | 2009-05-07 | 2015-12-09 | 费瑞姆医药有限公司 | 苯氧基甲基杂环化合物 |
| FR2953520B1 (fr) * | 2009-12-04 | 2011-11-25 | Sanofi Aventis | Derives de diphenyl-pyrazolopyridines, leur preparation et leur application en therapeutique |
| TWI429628B (zh) * | 2010-03-29 | 2014-03-11 | Univ Taipei Medical | 吲哚基或吲哚啉基羥肟酸化合物 |
| MY170236A (en) | 2010-10-06 | 2019-07-11 | Glaxosmithkline Llc | Benzimidazole derivatives as pi3 kinase inhibitors |
| US8975276B2 (en) * | 2011-06-29 | 2015-03-10 | Bristol-Myers Squibb Company | Inhibitors of PDE10 |
| CN103214481B (zh) * | 2012-01-21 | 2016-08-03 | 中国科学院上海药物研究所 | 新型咪唑并[1,2-a]吡啶类化合物、其制备方法、包含此类化合物的药物组合物及其用途 |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG10202004618TA (en) | 2015-11-19 | 2020-06-29 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| MA44075A (fr) | 2015-12-17 | 2021-05-19 | Incyte Corp | Dérivés de n-phényl-pyridine-2-carboxamide et leur utilisation en tant que modulateurs des interactions protéine/protéine pd-1/pd-l1 |
| AU2016379372A1 (en) | 2015-12-22 | 2018-08-02 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| AR108396A1 (es) | 2016-05-06 | 2018-08-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| WO2017205464A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| HUE060256T2 (hu) | 2016-06-20 | 2023-02-28 | Incyte Corp | Heterociklusos vegyületek mint immunmodulátorok |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018044783A1 (en) | 2016-08-29 | 2018-03-08 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| CN106631970A (zh) * | 2016-12-14 | 2017-05-10 | 贵州大学 | 一种6‑苯甲酰基‑1h‑吲哚的制备方法 |
| LT3558990T (lt) | 2016-12-22 | 2022-12-27 | Incyte Corporation | Tetrahidroimidazo[4,5-c]piridino dariniai kaip pd-l1 internalizavimo induktoriai |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| ES2874756T3 (es) | 2016-12-22 | 2021-11-05 | Incyte Corp | Derivados de triazolo[1,5-A]piridina como inmunomoduladores |
| US20180179202A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| JP7101678B2 (ja) | 2016-12-22 | 2022-07-15 | インサイト・コーポレイション | 免疫調節剤としての複素環式化合物 |
| SMT202500157T1 (it) | 2018-03-30 | 2025-05-12 | Incyte Corp | Composti eterociclici come immunomodulatori |
| HUE061503T2 (hu) | 2018-05-11 | 2023-07-28 | Incyte Corp | Tetrahidro-imidazo[4,5-C]piridin-származékok mint PD-L1 immunmodulátorok |
| 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 |
| PE20221038A1 (es) | 2019-09-30 | 2022-06-17 | Incyte Corp | Compuestos de pirido[3,2-d] pirimidina como inmunomoduladores |
| CA3160131A1 (en) | 2019-11-11 | 2021-05-20 | Incyte Corporation | Salts and crystalline forms of a pd-1/pd-l1 inhibitor |
| KR20230014706A (ko) * | 2020-04-24 | 2023-01-30 | 더 리전츠 오브 더 유니버시티 오브 캘리포니아 | Nurr1 수용체 조절제 및 이의 용도 |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| CR20230230A (es) | 2020-11-06 | 2023-07-27 | Incyte Corp | Proceso para hacer un inhibidor de pd-1/pdl1 y sales y formas cristalinas del mismo |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
| EP4370516A1 (en) * | 2021-07-16 | 2024-05-22 | Sanofi | 6h-imidazo[1,2-a]pyrrolo[2,3-e]pyridine derivatives for use in therapy |
| JP2024525791A (ja) | 2021-07-16 | 2024-07-12 | サノフイ | 治療に使用するためのイミダゾ［１，２－ｂ］［１，２，４］トリアゾール誘導体 |
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|---|---|---|---|---|
| DK1603570T5 (da) | 2003-02-26 | 2013-12-09 | Sugen Inc | Aminoheteroarylforbindelser som proteinkinaseinhibitorer |
| 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 |
| EP2137158A4 (en) * | 2007-02-28 | 2012-04-18 | Methylgene Inc | LOW-MOLECULAR INHIBITORS OF PROTEINARGININE METHYLTRANSFERASES (PRMTS) |
| FR2928922B1 (fr) | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives de 2-aryl-6-phenyl-imidazo°1,2-a!pyridines polysubstitues, 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 |
| 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 |
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2008
- 2008-03-21 FR FR0801585A patent/FR2928924B1/fr active Active
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2009
- 2009-03-19 AR ARP090100988A patent/AR070995A1/es not_active Application Discontinuation
- 2009-03-19 PE PE2009000414A patent/PE20091694A1/es not_active Application Discontinuation
- 2009-03-20 CN CN201310049249.7A patent/CN103145747B/zh not_active Expired - Fee Related
- 2009-03-20 KR KR1020107023402A patent/KR20100124830A/ko not_active Withdrawn
- 2009-03-20 BR BRPI0910309A patent/BRPI0910309A2/pt active Search and Examination
- 2009-03-20 CL CL2009000699A patent/CL2009000699A1/es unknown
- 2009-03-20 PH PH1/2012/501817A patent/PH12012501817A1/en unknown
- 2009-03-20 NZ NZ588083A patent/NZ588083A/en not_active IP Right Cessation
- 2009-03-20 AU AU2009253232A patent/AU2009253232B2/en not_active Ceased
- 2009-03-20 ME MEP-2010-150A patent/ME01112B/me unknown
- 2009-03-20 TW TW098109256A patent/TW200942541A/zh unknown
- 2009-03-20 WO PCT/FR2009/000298 patent/WO2009144392A1/fr not_active Ceased
- 2009-03-20 JP JP2011500259A patent/JP5508384B2/ja not_active Expired - Fee Related
- 2009-03-20 CN CN200980118584.XA patent/CN102036989B/zh not_active Expired - Fee Related
- 2009-03-20 CA CA2719118A patent/CA2719118C/fr not_active Expired - Fee Related
- 2009-03-20 EP EP09754042.1A patent/EP2262804B1/fr active Active
- 2009-03-20 UY UY0001031730A patent/UY31730A/es not_active Application Discontinuation
- 2009-03-20 MX MX2010010268A patent/MX2010010268A/es active IP Right Grant
- 2009-03-20 EA EA201071111A patent/EA201071111A1/ru unknown
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2010
- 2010-09-14 US US12/881,820 patent/US8088765B2/en not_active Expired - Fee Related
- 2010-09-19 IL IL208247A patent/IL208247A0/en unknown
- 2010-09-20 ZA ZA2010/06725A patent/ZA201006725B/en unknown
- 2010-09-20 CO CO10115913A patent/CO6300864A2/es not_active Application Discontinuation
- 2010-10-19 MA MA33274A patent/MA32248B1/fr unknown
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2011
- 2011-11-08 US US13/291,660 patent/US8598166B2/en not_active Expired - Fee Related
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