JP2008525463A5 - - Google Patents
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- JP2008525463A5 JP2008525463A5 JP2007548399A JP2007548399A JP2008525463A5 JP 2008525463 A5 JP2008525463 A5 JP 2008525463A5 JP 2007548399 A JP2007548399 A JP 2007548399A JP 2007548399 A JP2007548399 A JP 2007548399A JP 2008525463 A5 JP2008525463 A5 JP 2008525463A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- pyrrolo
- pyridin
- amino
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 316
- 125000000753 cycloalkyl group Chemical group 0.000 claims 85
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 82
- 125000003118 aryl group Chemical group 0.000 claims 73
- 125000001072 heteroaryl group Chemical group 0.000 claims 56
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 44
- 125000005843 halogen group Chemical group 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000005466 alkylenyl group Chemical group 0.000 claims 33
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 32
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 32
- 125000003710 aryl alkyl group Chemical group 0.000 claims 32
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 29
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 25
- 125000003342 alkenyl group Chemical group 0.000 claims 24
- 125000000304 alkynyl group Chemical group 0.000 claims 24
- -1 SONR 14 Inorganic materials 0.000 claims 23
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 23
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 20
- 125000001424 substituent group Chemical group 0.000 claims 20
- 229910052799 carbon Inorganic materials 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 229910052717 sulfur Inorganic materials 0.000 claims 19
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 18
- 125000003282 alkyl amino group Chemical group 0.000 claims 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims 18
- 239000008194 pharmaceutical composition Substances 0.000 claims 17
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 102000042838 JAK family Human genes 0.000 claims 7
- 108091082332 JAK family Proteins 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 150000003839 salts Chemical group 0.000 claims 7
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 5
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 208000017520 skin disease Diseases 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004442 acylamino group Chemical group 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 238000011200 topical administration Methods 0.000 claims 3
- FEIGMFOQJNOTKI-QRWLVFNGSA-N 4-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidin-1-yl]sulfonylbenzonitrile Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C1=CC=C(C#N)C=C1 FEIGMFOQJNOTKI-QRWLVFNGSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 101000844245 Homo sapiens Non-receptor tyrosine-protein kinase TYK2 Proteins 0.000 claims 2
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims 2
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims 2
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims 2
- 241000701806 Human papillomavirus Species 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 102100032028 Non-receptor tyrosine-protein kinase TYK2 Human genes 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 2
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 239000006071 cream Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 208000006454 hepatitis Diseases 0.000 claims 2
- 231100000283 hepatitis Toxicity 0.000 claims 2
- 239000006210 lotion Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000002674 ointment Substances 0.000 claims 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 230000003612 virological effect Effects 0.000 claims 2
- MOWFJFICKPVXIX-JMSVASOKSA-N (2r)-2-amino-1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidin-1-yl]propan-1-one Chemical compound C1N(C(=O)[C@H](N)C)CC[C@@H](C)[C@H]1N(C)C1=CC=NC2=C1C=CN2 MOWFJFICKPVXIX-JMSVASOKSA-N 0.000 claims 1
- GKEZBTVWYSNBFS-JMSVASOKSA-N (2r)-2-hydroxy-1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidin-1-yl]propan-1-one Chemical compound C1N(C(=O)[C@H](O)C)CC[C@@H](C)[C@H]1N(C)C1=CC=NC2=C1C=CN2 GKEZBTVWYSNBFS-JMSVASOKSA-N 0.000 claims 1
- GKEZBTVWYSNBFS-XUJVJEKNSA-N (2s)-2-hydroxy-1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidin-1-yl]propan-1-one Chemical compound C1N(C(=O)[C@@H](O)C)CC[C@@H](C)[C@H]1N(C)C1=CC=NC2=C1C=CN2 GKEZBTVWYSNBFS-XUJVJEKNSA-N 0.000 claims 1
- SISALGMRCAMPNX-PXAZEXFGSA-N (3,5-dimethyl-1,2-oxazol-4-yl)-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidin-1-yl]methanone Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)C=1C(C)=NOC=1C SISALGMRCAMPNX-PXAZEXFGSA-N 0.000 claims 1
- QOIVGBLGZCEHOA-VKJFTORMSA-N (3r)-1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carbonyl]pyrrolidine-3-carbonitrile Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)N1CC[C@@H](C#N)C1 QOIVGBLGZCEHOA-VKJFTORMSA-N 0.000 claims 1
- WQGWIHLGGWYJQT-DOMZBBRYSA-N (3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]-n-(1,3-thiazol-2-yl)piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NC1=NC=CS1 WQGWIHLGGWYJQT-DOMZBBRYSA-N 0.000 claims 1
- NWBOBJLSYDHHPY-CJNGLKHVSA-N (3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]-n-(1,3-thiazol-2-ylmethyl)piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NCC1=NC=CS1 NWBOBJLSYDHHPY-CJNGLKHVSA-N 0.000 claims 1
- APHIDOCYPDPSBT-UTKZUKDTSA-N (3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]-n-(2-phenylethyl)piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NCCC1=CC=CC=C1 APHIDOCYPDPSBT-UTKZUKDTSA-N 0.000 claims 1
- PZXWDQINAMVUGE-BEFAXECRSA-N (3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]-n-phenylpiperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NC1=CC=CC=C1 PZXWDQINAMVUGE-BEFAXECRSA-N 0.000 claims 1
- SKGZMJMHGPNKEQ-CJNGLKHVSA-N (3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]-n-thiophen-2-ylpiperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NC1=CC=CS1 SKGZMJMHGPNKEQ-CJNGLKHVSA-N 0.000 claims 1
- YFLBCJLVUIYCLX-UZLBHIALSA-N (3r,4r)-4-methyl-n-(4-methylphenyl)-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NC1=CC=C(C)C=C1 YFLBCJLVUIYCLX-UZLBHIALSA-N 0.000 claims 1
- FGPNUZCDABEMAI-DOMZBBRYSA-N (3r,4r)-n,n,4-trimethyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C[C@@H]1CCN(C(=O)N(C)C)C[C@@H]1N(C)C1=CC=NC2=C1C=CN2 FGPNUZCDABEMAI-DOMZBBRYSA-N 0.000 claims 1
- JMHJSLHSHLNXAQ-BEFAXECRSA-N (3r,4r)-n-(1,3-benzothiazol-2-ylmethyl)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C1=CC=C2SC(CNC(=O)N3CC[C@H]([C@H](C3)N(C)C=3C=4C=CNC=4N=CC=3)C)=NC2=C1 JMHJSLHSHLNXAQ-BEFAXECRSA-N 0.000 claims 1
- HTMPUZZFIGQLSK-CJNGLKHVSA-N (3r,4r)-n-(2-cyanoethyl)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C[C@@H]1CCN(C(=O)NCCC#N)C[C@@H]1N(C)C1=CC=NC2=C1C=CN2 HTMPUZZFIGQLSK-CJNGLKHVSA-N 0.000 claims 1
- RMQKUPZGKLBJTD-KUHUBIRLSA-N (3r,4r)-n-(2-fluorophenyl)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NC1=CC=CC=C1F RMQKUPZGKLBJTD-KUHUBIRLSA-N 0.000 claims 1
- YEOXKKLJNBFMOV-BEFAXECRSA-N (3r,4r)-n-(2-methoxyphenyl)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)N1C[C@H](N(C)C=2C=3C=CNC=3N=CC=2)[C@H](C)CC1 YEOXKKLJNBFMOV-BEFAXECRSA-N 0.000 claims 1
- KFFSRDOJYXCSER-QRWLVFNGSA-N (3r,4r)-n-(3-cyanophenyl)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NC1=CC=CC(C#N)=C1 KFFSRDOJYXCSER-QRWLVFNGSA-N 0.000 claims 1
- KUUCNLNWERNERX-KUHUBIRLSA-N (3r,4r)-n-(3-fluorophenyl)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NC1=CC=CC(F)=C1 KUUCNLNWERNERX-KUHUBIRLSA-N 0.000 claims 1
- VVCWMVXBEICYIX-DOMZBBRYSA-N (3r,4r)-n-(4,5-dihydro-1,3-thiazol-2-yl)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NC1=NCCS1 VVCWMVXBEICYIX-DOMZBBRYSA-N 0.000 claims 1
- LLPMAWMFAYDRRP-QRWLVFNGSA-N (3r,4r)-n-(4-cyanophenyl)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carbothioamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=S)NC1=CC=C(C#N)C=C1 LLPMAWMFAYDRRP-QRWLVFNGSA-N 0.000 claims 1
- IIEADARWBXWHEB-QRWLVFNGSA-N (3r,4r)-n-(4-cyanophenyl)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NC1=CC=C(C#N)C=C1 IIEADARWBXWHEB-QRWLVFNGSA-N 0.000 claims 1
- ZWMXUOPTTLCEJM-IERDGZPVSA-N (3r,4r)-n-(4-cyanophenyl)-n,4-dimethyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)N(C)C1=CC=C(C#N)C=C1 ZWMXUOPTTLCEJM-IERDGZPVSA-N 0.000 claims 1
- SWZLYSCPIAPNHD-KUHUBIRLSA-N (3r,4r)-n-(4-fluorophenyl)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NC1=CC=C(F)C=C1 SWZLYSCPIAPNHD-KUHUBIRLSA-N 0.000 claims 1
- VQLSQXUFHBHENZ-UZLBHIALSA-N (3r,4r)-n-benzyl-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)NCC1=CC=CC=C1 VQLSQXUFHBHENZ-UZLBHIALSA-N 0.000 claims 1
- MBOSFMVGMJNTNW-DOMZBBRYSA-N (3r,4r)-n-ethyl-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxamide Chemical compound C1N(C(=O)NCC)CC[C@@H](C)[C@H]1N(C)C1=CC=NC2=C1C=CN2 MBOSFMVGMJNTNW-DOMZBBRYSA-N 0.000 claims 1
- QOIVGBLGZCEHOA-RKVPGOIHSA-N (3s)-1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carbonyl]pyrrolidine-3-carbonitrile Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)N1CC[C@H](C#N)C1 QOIVGBLGZCEHOA-RKVPGOIHSA-N 0.000 claims 1
- IYWPLRRKDTVPEP-DOMZBBRYSA-N 1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidin-1-yl]-2-methylsulfanylethanone Chemical compound C1N(C(=O)CSC)CC[C@@H](C)[C@H]1N(C)C1=CC=NC2=C1C=CN2 IYWPLRRKDTVPEP-DOMZBBRYSA-N 0.000 claims 1
- KSEKTQWBPGEKKZ-UTKZUKDTSA-N 1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidin-1-yl]-3-phenylpropan-1-one Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)CCC1=CC=CC=C1 KSEKTQWBPGEKKZ-UTKZUKDTSA-N 0.000 claims 1
- VKTWBNDQERIDBW-UZLBHIALSA-N 1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidin-1-yl]-3-pyridin-3-ylpropan-1-one Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)CCC1=CC=CN=C1 VKTWBNDQERIDBW-UZLBHIALSA-N 0.000 claims 1
- XKVQUXSVVDPXNH-ABAIWWIYSA-N 1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidin-1-yl]ethanone Chemical compound C[C@@H]1CCN(C(C)=O)C[C@@H]1N(C)C1=CC=NC2=C1C=CN2 XKVQUXSVVDPXNH-ABAIWWIYSA-N 0.000 claims 1
- PDIFFOSTMOSXNN-YKSBVNFPSA-N 1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carbonyl]-4-phenylpiperidine-4-carbonitrile Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)N(CC1)CCC1(C#N)C1=CC=CC=C1 PDIFFOSTMOSXNN-YKSBVNFPSA-N 0.000 claims 1
- RADBTFFRUAKTLS-DYVFJYSZSA-N 1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carbonyl]azetidine-3-carbonitrile Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)N1CC(C#N)C1 RADBTFFRUAKTLS-DYVFJYSZSA-N 0.000 claims 1
- ICZQPRVERITQSO-LQUOLJLFSA-N 1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carbonyl]piperidine-3-carbonitrile Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)N1CCCC(C#N)C1 ICZQPRVERITQSO-LQUOLJLFSA-N 0.000 claims 1
- PLXNGJBMSKRBRN-BEFAXECRSA-N 1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carbonyl]piperidine-4-carbonitrile Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)N1CCC(C#N)CC1 PLXNGJBMSKRBRN-BEFAXECRSA-N 0.000 claims 1
- GVADLFFOWLMRIQ-XTUQQUOLSA-N 1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carbonyl]pyrrolidine-3,4-dicarbonitrile Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)N1CC(C#N)C(C#N)C1 GVADLFFOWLMRIQ-XTUQQUOLSA-N 0.000 claims 1
- QOIVGBLGZCEHOA-STGLDUPZSA-N 1-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carbonyl]pyrrolidine-3-carbonitrile Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)N1CCC(C#N)C1 QOIVGBLGZCEHOA-STGLDUPZSA-N 0.000 claims 1
- BYRQWLXAHZEHRO-UZLBHIALSA-N 1-[2-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidin-1-yl]-2-oxoethyl]piperidine-4-carbonitrile Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)CN1CCC(C#N)CC1 BYRQWLXAHZEHRO-UZLBHIALSA-N 0.000 claims 1
- RTFCYJRJYXFIHE-QRWLVFNGSA-N 1-[4-[(3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carbonyl]piperidin-1-yl]ethanone Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)C1CCN(C(C)=O)CC1 RTFCYJRJYXFIHE-QRWLVFNGSA-N 0.000 claims 1
- RCWISWVYKNLXHC-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound NC1=CC=NC2=C1C=CN2 RCWISWVYKNLXHC-UHFFFAOYSA-N 0.000 claims 1
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- RDAOCGJQAHJBRF-ACJLOTCBSA-N n-methyl-n-[(3r,4r)-4-methyl-1-(1,3,5-trimethylpyrazol-4-yl)sulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C=1C(C)=NN(C)C=1C RDAOCGJQAHJBRF-ACJLOTCBSA-N 0.000 claims 1
- MQBGTSZQWOGZDY-CJNGLKHVSA-N n-methyl-n-[(3r,4r)-4-methyl-1-(1-methylimidazol-4-yl)sulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C1=CN(C)C=N1 MQBGTSZQWOGZDY-CJNGLKHVSA-N 0.000 claims 1
- USQNMNIEDOOLBG-BEFAXECRSA-N n-methyl-n-[(3r,4r)-4-methyl-1-(2-methylphenyl)sulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C1=CC=CC=C1C USQNMNIEDOOLBG-BEFAXECRSA-N 0.000 claims 1
- VYBBICLKXWLMNW-UZLBHIALSA-N n-methyl-n-[(3r,4r)-4-methyl-1-(3-methylphenyl)sulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C1=CC=CC(C)=C1 VYBBICLKXWLMNW-UZLBHIALSA-N 0.000 claims 1
- DVAPCXYDQIUOOM-UZLBHIALSA-N n-methyl-n-[(3r,4r)-4-methyl-1-(4-methylphenyl)sulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C1=CC=C(C)C=C1 DVAPCXYDQIUOOM-UZLBHIALSA-N 0.000 claims 1
- FOKUEEJPJPQNMM-JPYJTQIMSA-N n-methyl-n-[(3r,4r)-4-methyl-1-(4-pyridin-2-yloxyphenyl)sulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=N1 FOKUEEJPJPQNMM-JPYJTQIMSA-N 0.000 claims 1
- DQFLAXWHEBICAH-UZLBHIALSA-N n-methyl-n-[(3r,4r)-4-methyl-1-(5-pyridin-3-ylthiophen-2-yl)sulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C(S1)=CC=C1C1=CC=CN=C1 DQFLAXWHEBICAH-UZLBHIALSA-N 0.000 claims 1
- WXWJATZJTHOOQG-BEFAXECRSA-N n-methyl-n-[(3r,4r)-4-methyl-1-(pyridin-2-ylmethylsulfonyl)piperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)CC1=CC=CC=N1 WXWJATZJTHOOQG-BEFAXECRSA-N 0.000 claims 1
- JJNKDJZHXPMSRW-BEFAXECRSA-N n-methyl-n-[(3r,4r)-4-methyl-1-(pyridin-3-ylmethylsulfonyl)piperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)CC1=CC=CN=C1 JJNKDJZHXPMSRW-BEFAXECRSA-N 0.000 claims 1
- WOZWYZCBEDGSMG-BEFAXECRSA-N n-methyl-n-[(3r,4r)-4-methyl-1-(pyridin-4-ylmethylsulfonyl)piperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)CC1=CC=NC=C1 WOZWYZCBEDGSMG-BEFAXECRSA-N 0.000 claims 1
- KJQQSHOHTAWAFU-MFKMUULPSA-N n-methyl-n-[(3r,4r)-4-methyl-1-(trifluoromethylsulfonyl)piperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C[C@@H]1CCN(S(=O)(=O)C(F)(F)F)C[C@@H]1N(C)C1=CC=NC2=C1C=CN2 KJQQSHOHTAWAFU-MFKMUULPSA-N 0.000 claims 1
- CAUSFSVTQDSQEW-WBMJQRKESA-N n-methyl-n-[(3r,4r)-4-methyl-1-[(5-methyl-1,2-oxazol-4-yl)sulfonyl]piperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C=1C=NOC=1C CAUSFSVTQDSQEW-WBMJQRKESA-N 0.000 claims 1
- YTLUJNKVCWZYJZ-IERDGZPVSA-N n-methyl-n-[(3r,4r)-4-methyl-1-[4-(1,3-oxazol-5-yl)phenyl]sulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C(C=C1)=CC=C1C1=CN=CO1 YTLUJNKVCWZYJZ-IERDGZPVSA-N 0.000 claims 1
- OSHHDOINCWXOCF-PBHICJAKSA-N n-methyl-n-[(3r,4r)-4-methyl-1-[5-(1,3-oxazol-5-yl)thiophen-2-yl]sulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C(S1)=CC=C1C1=CN=CO1 OSHHDOINCWXOCF-PBHICJAKSA-N 0.000 claims 1
- DBSKUHNPYKIAFL-RISCZKNCSA-N n-methyl-n-[(3r,4r)-4-methyl-1-methylsulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical class C[C@@H]1CCN(S(C)(=O)=O)C[C@@H]1N(C)C1=CC=NC2=C1C=CN2 DBSKUHNPYKIAFL-RISCZKNCSA-N 0.000 claims 1
- HNPHJUNDFOJTPR-CJNGLKHVSA-N n-methyl-n-[(3r,4r)-4-methyl-1-propan-2-ylsulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical class C1N(S(=O)(=O)C(C)C)CC[C@@H](C)[C@H]1N(C)C1=CC=NC2=C1C=CN2 HNPHJUNDFOJTPR-CJNGLKHVSA-N 0.000 claims 1
- DGYLSOYGPYGVPW-CJNGLKHVSA-N n-methyl-n-[(3r,4r)-4-methyl-1-propylsulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical class C1N(S(=O)(=O)CCC)CC[C@@H](C)[C@H]1N(C)C1=CC=NC2=C1C=CN2 DGYLSOYGPYGVPW-CJNGLKHVSA-N 0.000 claims 1
- PSJLRHQXOQZUSC-KDOFPFPSSA-N n-methyl-n-[(3r,4r)-4-methyl-1-pyridin-3-ylsulfonylpiperidin-3-yl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1S(=O)(=O)C1=CC=CN=C1 PSJLRHQXOQZUSC-KDOFPFPSSA-N 0.000 claims 1
- GYQLEKFEAKFSQB-BEFAXECRSA-N phenyl (3r,4r)-4-methyl-3-[methyl(1h-pyrrolo[2,3-b]pyridin-4-yl)amino]piperidine-1-carboxylate Chemical compound C([C@H]([C@H](C1)N(C)C=2C=3C=CNC=3N=CC=2)C)CN1C(=O)OC1=CC=CC=C1 GYQLEKFEAKFSQB-BEFAXECRSA-N 0.000 claims 1
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- 2005-12-20 AR ARP050105384A patent/AR054416A1/es not_active Application Discontinuation
- 2005-12-21 ES ES05854854.6T patent/ES2536331T3/es not_active Expired - Lifetime
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- 2005-12-21 CA CA2592119A patent/CA2592119C/en not_active Expired - Lifetime
- 2005-12-21 PT PT131715245T patent/PT2671882T/pt unknown
- 2005-12-21 ES ES13171524.5T patent/ES2666819T3/es not_active Expired - Lifetime
- 2005-12-21 EP EP13171524.5A patent/EP2671882B1/en not_active Expired - Lifetime
- 2005-12-21 TW TW102125796A patent/TW201414732A/zh unknown
- 2005-12-21 TW TW094145677A patent/TWI439459B/zh not_active IP Right Cessation
- 2005-12-21 ME MEP-2018-99A patent/ME03017B/me unknown
- 2005-12-21 DK DK13171524.5T patent/DK2671882T3/en active
- 2005-12-21 LT LTEP13171524.5T patent/LT2671882T/lt unknown
- 2005-12-21 WO PCT/US2005/046207 patent/WO2006069080A2/en not_active Ceased
- 2005-12-21 JP JP2007548399A patent/JP5048514B2/ja not_active Expired - Lifetime
- 2005-12-21 PL PL13171524T patent/PL2671882T3/pl unknown
- 2005-12-21 US US11/313,394 patent/US7335667B2/en active Active
- 2005-12-21 SI SI200532196T patent/SI2671882T1/en unknown
- 2005-12-21 HU HUE13171524A patent/HUE037435T2/hu unknown
- 2005-12-21 EP EP05854854.6A patent/EP1828181B1/en not_active Expired - Lifetime
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2007
- 2007-10-30 US US11/980,314 patent/US8053433B2/en active Active
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2011
- 2011-09-26 US US13/245,333 patent/US8445488B2/en not_active Expired - Lifetime
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2012
- 2012-04-23 JP JP2012097921A patent/JP5970676B2/ja not_active Expired - Lifetime
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2013
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2014
- 2014-04-17 US US14/255,092 patent/US9090611B2/en not_active Expired - Lifetime
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2015
- 2015-07-15 US US14/799,777 patent/US9580419B2/en not_active Expired - Lifetime
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2017
- 2017-01-18 US US15/409,085 patent/US9879010B2/en not_active Expired - Lifetime
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