KR20100124830A - 6-헤테로아릴-이미다조［1,2-ａ］피리딘의 다중치환된 유도체, 및 그의 제법 및 치료 용도 - Google Patents
6-헤테로아릴-이미다조［1,2-ａ］피리딘의 다중치환된 유도체, 및 그의 제법 및 치료 용도 Download PDFInfo
- Publication number
- KR20100124830A KR20100124830A KR1020107023402A KR20107023402A KR20100124830A KR 20100124830 A KR20100124830 A KR 20100124830A KR 1020107023402 A KR1020107023402 A KR 1020107023402A KR 20107023402 A KR20107023402 A KR 20107023402A KR 20100124830 A KR20100124830 A KR 20100124830A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridin
- methanol
- imidazo
- thien
- group
- 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.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title description 5
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 210
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 84
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 70
- 229910003827 NRaRb Inorganic materials 0.000 claims abstract description 49
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 40
- 150000002367 halogens Chemical class 0.000 claims abstract description 40
- 125000001424 substituent group Chemical group 0.000 claims abstract description 39
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims abstract description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 125000004429 atom Chemical group 0.000 claims abstract description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 191
- -1 CONRaRb Inorganic materials 0.000 claims description 98
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 78
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000002541 furyl group Chemical group 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000000335 thiazolyl group Chemical group 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 150000003840 hydrochlorides Chemical class 0.000 claims description 16
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 11
- 229910052701 rubidium Inorganic materials 0.000 claims description 11
- 230000002265 prevention Effects 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 9
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 150000001638 boron Chemical class 0.000 claims description 9
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004001 thioalkyl group Chemical group 0.000 claims description 8
- 229910052796 boron Inorganic materials 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 150000003927 aminopyridines Chemical class 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000006557 (C2-C5) alkylene group Chemical group 0.000 claims description 4
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 4
- XONOUHCQIIFDES-UHFFFAOYSA-N 2-[2-[2-(1h-indol-6-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl]propan-2-ol Chemical compound CC(C)(O)C1=CC=NC(C2=CN3C=C(N=C3C=C2)C=2C=C3NC=CC3=CC=2)=C1 XONOUHCQIIFDES-UHFFFAOYSA-N 0.000 claims description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- ZMLNYOFVSCYQTD-UHFFFAOYSA-N [4-[2-(2-fluorophenyl)imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound S1C(CO)=NC(C2=CN3C=C(N=C3C=C2)C=2C(=CC=CC=2)F)=C1 ZMLNYOFVSCYQTD-UHFFFAOYSA-N 0.000 claims description 4
- YEFYSCWEYWAGDU-UHFFFAOYSA-N [4-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound S1C(CO)=NC(C2=CN3C=C(N=C3C=C2)C=2C=CC(Cl)=CC=2)=C1 YEFYSCWEYWAGDU-UHFFFAOYSA-N 0.000 claims description 4
- GFEZAESQIYMHBD-UHFFFAOYSA-N [5-[2-(1h-indol-6-yl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C1=CN2C=C(C=3C=C4NC=CC4=CC=3)N=C2C=C1 GFEZAESQIYMHBD-UHFFFAOYSA-N 0.000 claims description 4
- QXYFJXZJSSAPHG-UHFFFAOYSA-N [5-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C1=CN2C=C(C=3C=CC(Cl)=CC=3)N=C2C=C1 QXYFJXZJSSAPHG-UHFFFAOYSA-N 0.000 claims description 4
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 125000002944 cyanoaryl group Chemical group 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
- JAYSSVIRQJHKHU-UHFFFAOYSA-N 2-[2-[2-(1h-indazol-3-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl]propan-2-ol Chemical compound CC(C)(O)C1=CC=NC(C2=CN3C=C(N=C3C=C2)C=2C3=CC=CC=C3NN=2)=C1 JAYSSVIRQJHKHU-UHFFFAOYSA-N 0.000 claims description 3
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- UQTBWLPEAMWCEO-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-[4-(methoxymethyl)furan-2-yl]imidazo[1,2-a]pyridine Chemical compound COCC1=COC(C2=CN3C=C(N=C3C=C2)C=2C=CC(Cl)=CC=2)=C1 UQTBWLPEAMWCEO-UHFFFAOYSA-N 0.000 claims description 2
- KJRBISCCZGVXNM-UHFFFAOYSA-N 2-[2-[2-(5-methyl-1,2-oxazol-3-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl]propan-2-ol Chemical compound O1C(C)=CC(C=2N=C3C=CC(=CN3C=2)C=2N=CC=C(C=2)C(C)(C)O)=N1 KJRBISCCZGVXNM-UHFFFAOYSA-N 0.000 claims description 2
- ZRBBCMFRKYKXKL-UHFFFAOYSA-N 2-[4-[2-(1h-indol-6-yl)imidazo[1,2-a]pyridin-6-yl]-1h-pyrazol-5-yl]propan-2-ol Chemical compound CC(C)(O)C1=NNC=C1C1=CN2C=C(C=3C=C4NC=CC4=CC=3)N=C2C=C1 ZRBBCMFRKYKXKL-UHFFFAOYSA-N 0.000 claims description 2
- GUMYNFLLBMYTJJ-UHFFFAOYSA-N 2-[5-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl]propan-2-ol Chemical compound O1C(C(C)(O)C)=CC=C1C1=CN2C=C(C=3C=CC(Cl)=CC=3)N=C2C=C1 GUMYNFLLBMYTJJ-UHFFFAOYSA-N 0.000 claims description 2
- IHAFOBVVENYGCE-UHFFFAOYSA-N 2-[5-fluoro-2-[2-(1h-indol-6-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl]propan-2-ol Chemical compound C1=C(F)C(C(C)(O)C)=CC(C2=CN3C=C(N=C3C=C2)C=2C=C3NC=CC3=CC=2)=N1 IHAFOBVVENYGCE-UHFFFAOYSA-N 0.000 claims description 2
- LZHNVGYDDOOXKR-UHFFFAOYSA-N 2-fluoro-4-[6-[5-(hydroxymethyl)furan-2-yl]imidazo[1,2-a]pyridin-2-yl]-n,n-dimethylbenzamide Chemical compound C1=C(F)C(C(=O)N(C)C)=CC=C1C1=CN(C=C(C=C2)C=3OC(CO)=CC=3)C2=N1 LZHNVGYDDOOXKR-UHFFFAOYSA-N 0.000 claims description 2
- MFHSGEYIGHVTAV-UHFFFAOYSA-N 2-fluoro-4-[6-[5-(hydroxymethyl)thiophen-3-yl]imidazo[1,2-a]pyridin-2-yl]-n,n-dimethylbenzamide Chemical compound C1=C(F)C(C(=O)N(C)C)=CC=C1C1=CN(C=C(C=C2)C=3C=C(CO)SC=3)C2=N1 MFHSGEYIGHVTAV-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- JYERWXFXXGLMMU-UHFFFAOYSA-N 3-[6-[2-(hydroxymethyl)-1,3-thiazol-4-yl]imidazo[1,2-a]pyridin-2-yl]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(C=2N=C3C=CC(=CN3C=2)C=2N=C(CO)SC=2)=C1 JYERWXFXXGLMMU-UHFFFAOYSA-N 0.000 claims description 2
- BTTLGSZLRNDKSL-UHFFFAOYSA-N 3-[6-[2-(hydroxymethyl)-1,3-thiazol-4-yl]imidazo[1,2-a]pyridin-2-yl]-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(C=2N=C3C=CC(=CN3C=2)C=2N=C(CO)SC=2)=C1 BTTLGSZLRNDKSL-UHFFFAOYSA-N 0.000 claims description 2
- HJHFJHTZLHBXMS-UHFFFAOYSA-N 3-[6-[5-(hydroxymethyl)furan-2-yl]imidazo[1,2-a]pyridin-2-yl]benzonitrile Chemical compound O1C(CO)=CC=C1C1=CN2C=C(C=3C=C(C=CC=3)C#N)N=C2C=C1 HJHFJHTZLHBXMS-UHFFFAOYSA-N 0.000 claims description 2
- QWQQPSSUGSSJKW-UHFFFAOYSA-N 3-[6-[5-(hydroxymethyl)thiophen-3-yl]imidazo[1,2-a]pyridin-2-yl]benzonitrile Chemical compound S1C(CO)=CC(C2=CN3C=C(N=C3C=C2)C=2C=C(C=CC=2)C#N)=C1 QWQQPSSUGSSJKW-UHFFFAOYSA-N 0.000 claims description 2
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- MHNZGXQSZPSFEL-UHFFFAOYSA-N 4-[6-[2-(hydroxymethyl)-1,3-thiazol-4-yl]imidazo[1,2-a]pyridin-2-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN(C=C(C=C2)C=3N=C(CO)SC=3)C2=N1 MHNZGXQSZPSFEL-UHFFFAOYSA-N 0.000 claims description 2
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- BPERDCKCFHDFMF-UHFFFAOYSA-N 4-[6-[5-(hydroxymethyl)thiophen-3-yl]imidazo[1,2-a]pyridin-2-yl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=CN(C=C(C=C2)C=3C=C(CO)SC=3)C2=N1 BPERDCKCFHDFMF-UHFFFAOYSA-N 0.000 claims description 2
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- PKNBXHCBUHXRBE-UHFFFAOYSA-N [2-(2-phenylimidazo[1,2-a]pyridin-6-yl)pyridin-4-yl]methanol Chemical compound OCC1=CC=NC(C2=CN3C=C(N=C3C=C2)C=2C=CC=CC=2)=C1 PKNBXHCBUHXRBE-UHFFFAOYSA-N 0.000 claims description 2
- AYUNKYRYHNZBLK-UHFFFAOYSA-N [2-(2-quinolin-3-ylimidazo[1,2-a]pyridin-6-yl)pyridin-4-yl]methanol Chemical compound OCC1=CC=NC(C2=CN3C=C(N=C3C=C2)C=2C=C3C=CC=CC3=NC=2)=C1 AYUNKYRYHNZBLK-UHFFFAOYSA-N 0.000 claims description 2
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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- Pyridine Compounds (AREA)
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| CN102131801B (zh) | 2008-06-25 | 2015-04-08 | 福拉姆医药股份有限公司 | 1,2-二取代的杂环化合物 |
| 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 |
| SI2617420T1 (sl) | 2009-05-07 | 2016-02-29 | Forum Pharmaceuticals Inc. | Fenoksimetil heterociklične spojine |
| 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 |
| KR101594002B1 (ko) | 2010-10-06 | 2016-02-15 | 글락소스미스클라인 엘엘씨 | Ｐｉ３ 키나제 억제제로서의 벤즈이미다졸 유도체 |
| 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 |
| US20170107216A1 (en) | 2015-10-19 | 2017-04-20 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| MD3377488T2 (ro) | 2015-11-19 | 2023-02-28 | Incyte Corp | Compuși heterociclici ca imunomodulatori |
| ES2916874T3 (es) | 2015-12-17 | 2022-07-06 | Incyte Corp | Derivados de N-fenil-piridina-2-carboxamida y su uso como moduladores de la interacción proteína/proteína PD-1/PD-L1 |
| CA3009474A1 (en) | 2015-12-22 | 2017-06-29 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| ES2906460T3 (es) | 2016-05-06 | 2022-04-18 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| EP3464279B1 (en) | 2016-05-26 | 2021-11-24 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG11201811414TA (en) | 2016-06-20 | 2019-01-30 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| MA45669A (fr) | 2016-07-14 | 2019-05-22 | Incyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| US20180057486A1 (en) | 2016-08-29 | 2018-03-01 | 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 |
| WO2018119286A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| US10308644B2 (en) | 2016-12-22 | 2019-06-04 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018119236A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| EP4223369A1 (en) | 2016-12-22 | 2023-08-09 | Incyte Corporation | Immunomodulator compounds and methods of use |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| SMT202300065T1 (it) | 2018-03-30 | 2023-05-12 | Incyte Corp | Composti eterociclici come immunomodulatori |
| CN112752756B (zh) | 2018-05-11 | 2024-06-25 | 因赛特公司 | 作为PD-L1免疫调节剂的四氢-咪唑并[4,5-c]吡啶衍生物 |
| TW202115059A (zh) | 2019-08-09 | 2021-04-16 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之鹽 |
| JP7559059B2 (ja) | 2019-09-30 | 2024-10-01 | インサイト・コーポレイション | 免疫調節剤としてのピリド［３，２－ｄ］ピリミジン化合物 |
| EP4058461A1 (en) | 2019-11-11 | 2022-09-21 | Incyte Corporation | Salts and crystalline forms of a pd-1/pd-l1 inhibitor |
| US20230255934A1 (en) * | 2020-04-24 | 2023-08-17 | The Regents Of The University Of California | Nurr1 receptor modulators and uses thereof |
| IL302590A (en) | 2020-11-06 | 2023-07-01 | Incyte Corp | Process for preparing PD-1/PD-L1 inhibitor and salts and crystalline forms thereof |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
| US11760756B2 (en) | 2020-11-06 | 2023-09-19 | Incyte Corporation | Crystalline form of a PD-1/PD-L1 inhibitor |
| US20240294529A1 (en) * | 2021-07-16 | 2024-09-05 | Sanofi | 6h-imidazo[1,2-a]pyrrolo[2,3-e]pyridine derivatives for use in therapy |
| CN117916240A (zh) | 2021-07-16 | 2024-04-19 | 赛诺菲 | 用于疗法的咪唑并[1,2-b][1,2,4]三唑衍生物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| PT2476667E (pt) | 2003-02-26 | 2014-09-18 | Sugen Inc | Compostos de aminoheteroarilo como inibidores da proteína quinase |
| 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 |
| US8338437B2 (en) * | 2007-02-28 | 2012-12-25 | Methylgene Inc. | Amines as small molecule inhibitors |
| 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
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- 2009-03-20 WO PCT/FR2009/000298 patent/WO2009144392A1/fr not_active Ceased
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