RU2011140061A - Сульфонилированные тетрагидроазолопиразины и их применение в качестве лекарственных средств - Google Patents
Сульфонилированные тетрагидроазолопиразины и их применение в качестве лекарственных средств Download PDFInfo
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- RU2011140061A RU2011140061A RU2011140061/04A RU2011140061A RU2011140061A RU 2011140061 A RU2011140061 A RU 2011140061A RU 2011140061/04 A RU2011140061/04 A RU 2011140061/04A RU 2011140061 A RU2011140061 A RU 2011140061A RU 2011140061 A RU2011140061 A RU 2011140061A
- Authority
- RU
- Russia
- Prior art keywords
- pyrazin
- tetrahydropyrrolo
- methyl
- phenyl
- sulfonyl
- Prior art date
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- 239000003814 drug Substances 0.000 title claims 3
- WEXJJSPMIBHSKF-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-pyrrolo[2,3-b]pyrazine Chemical class N1CCNC2=C1C=CN2 WEXJJSPMIBHSKF-UHFFFAOYSA-N 0.000 title 1
- 229940079593 drug Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 103
- 125000003118 aryl group Chemical group 0.000 claims abstract 79
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 76
- 125000001424 substituent group Chemical group 0.000 claims abstract 70
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 57
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract 34
- 150000001875 compounds Chemical class 0.000 claims abstract 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- -1 O-aryl Chemical group 0.000 claims 158
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 99
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 77
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 66
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 48
- 125000004076 pyridyl group Chemical group 0.000 claims 38
- 125000001544 thienyl group Chemical group 0.000 claims 33
- 125000002883 imidazolyl group Chemical group 0.000 claims 29
- 125000000335 thiazolyl group Chemical group 0.000 claims 29
- 125000001425 triazolyl group Chemical group 0.000 claims 29
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 24
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 22
- 125000002947 alkylene group Chemical group 0.000 claims 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 17
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 13
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 9
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000002393 azetidinyl group Chemical group 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000004193 piperazinyl group Chemical group 0.000 claims 7
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 7
- 125000004891 1-methylpropylamino group Chemical group CC(CC)N* 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 5
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 4
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims 3
- FOZRUQXXDOKJAA-UHFFFAOYSA-N 1-(2-pyridin-4-yl-2,8-diazaspiro[4.5]decan-8-yl)-2-[[2-[2-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]ethanone Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)N1C(COCC(=O)N2CCC3(CN(CC3)C=3C=CN=CC=3)CC2)C2=CC=CN2CC1 FOZRUQXXDOKJAA-UHFFFAOYSA-N 0.000 claims 3
- UCLDBTGVFGDWOA-UHFFFAOYSA-N 2-[2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2CC3=CC=C(CN4CCCC4)C=C3CC2)C2=CC=CN2CC1 UCLDBTGVFGDWOA-UHFFFAOYSA-N 0.000 claims 3
- NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 150000001923 cyclic compounds Chemical class 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 2
- DCIBWELHZUAGFH-UHFFFAOYSA-N 1-(2,8-diazaspiro[4.5]decan-8-yl)-2-[[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCC3(CNCC3)CC2)C2=CC=CN2CC1 DCIBWELHZUAGFH-UHFFFAOYSA-N 0.000 claims 2
- ULVNEMKIZJJHCB-UHFFFAOYSA-N 1-(4-benzyl-4-hydroxypiperidin-1-yl)-2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCC(O)(CC=3C=CC=CC=3)CC2)C2=CC=CN2CC1 ULVNEMKIZJJHCB-UHFFFAOYSA-N 0.000 claims 2
- IUTRORGAVBACJD-UHFFFAOYSA-N 1-(4-benzylpiperidin-1-yl)-2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCC(CC=3C=CC=CC=3)CC2)C2=CC=CN2CC1 IUTRORGAVBACJD-UHFFFAOYSA-N 0.000 claims 2
- YQKCPMDJZDLHFF-UHFFFAOYSA-N 1-[2-[4-(dimethylamino)phenyl]azepan-1-yl]-2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2C(CCCCC2)C=2C=CC(=CC=2)N(C)C)C2=CC=CN2CC1 YQKCPMDJZDLHFF-UHFFFAOYSA-N 0.000 claims 2
- VEMYPWASWGWLOE-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC=3C=C4OCOC4=CC=3)CC2)C2=CC=CN2CC1 VEMYPWASWGWLOE-UHFFFAOYSA-N 0.000 claims 2
- HIERXYYGTIVCPF-UHFFFAOYSA-N 1-[4-(2-hydroxyethyl)piperazin-1-yl]-2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CCO)CC2)C2=CC=CN2CC1 HIERXYYGTIVCPF-UHFFFAOYSA-N 0.000 claims 2
- FLFHPIACKXUEPF-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCC(O)(CC2)C=2C=CC(Cl)=CC=2)C2=CC=CN2CC1 FLFHPIACKXUEPF-UHFFFAOYSA-N 0.000 claims 2
- JYUSLMCHEJOQLD-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)piperazin-1-yl]-2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC2)C=2C=CC(F)=CC=2)C2=CC=CN2CC1 JYUSLMCHEJOQLD-UHFFFAOYSA-N 0.000 claims 2
- OBJMXHUQZXJVOI-UHFFFAOYSA-N 1-[4-[2-(2,5-dimethylpyrrol-1-yl)ethyl]piperazin-1-yl]-2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CCN3C(=CC=C3C)C)CC2)C2=CC=CN2CC1 OBJMXHUQZXJVOI-UHFFFAOYSA-N 0.000 claims 2
- QLFKFKZRFAPHSS-UHFFFAOYSA-N 1-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]-2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCC(O)(CC2)C=2C=C(C=CC=2)C(F)(F)F)C2=CC=CN2CC1 QLFKFKZRFAPHSS-UHFFFAOYSA-N 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- QCQZQDBSTACATP-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-morpholin-4-ylpiperidin-1-yl)ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCC(CC2)N2CCOCC2)C2=CC=CN2CC1 QCQZQDBSTACATP-UHFFFAOYSA-N 0.000 claims 2
- XPGYMZMASFBCOL-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-piperidin-1-ylpiperidin-1-yl)ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCC(CC2)N2CCCCC2)C2=CC=CN2CC1 XPGYMZMASFBCOL-UHFFFAOYSA-N 0.000 claims 2
- YHJMVYHYLOJDHI-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-propan-2-ylpiperazin-1-yl)ethanone Chemical compound C1CN(C(C)C)CCN1C(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=C(C)C=CC=C1Cl YHJMVYHYLOJDHI-UHFFFAOYSA-N 0.000 claims 2
- LZXRJQRFHWELQW-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[2-(pyridin-2-ylmethyl)piperidin-1-yl]ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2C(CCCC2)CC=2N=CC=CC=2)C2=CC=CN2CC1 LZXRJQRFHWELQW-UHFFFAOYSA-N 0.000 claims 2
- MQDZBEAZGKIWHK-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[2-(pyridin-2-ylmethyl)pyrrolidin-1-yl]ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2C(CCC2)CC=2N=CC=CC=2)C2=CC=CN2CC1 MQDZBEAZGKIWHK-UHFFFAOYSA-N 0.000 claims 2
- CGRRGRGELCWJJP-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[2-(pyridin-4-ylmethyl)piperidin-1-yl]ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2C(CCCC2)CC=2C=CN=CC=2)C2=CC=CN2CC1 CGRRGRGELCWJJP-UHFFFAOYSA-N 0.000 claims 2
- SEVWKPZMYGGNNP-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(2-fluorophenyl)piperazin-1-yl]ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC2)C=2C(=CC=CC=2)F)C2=CC=CN2CC1 SEVWKPZMYGGNNP-UHFFFAOYSA-N 0.000 claims 2
- OXLBMFRQXNFTPG-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(4-fluorophenyl)piperazin-1-yl]ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC2)C=2C=CC(F)=CC=2)C2=CC=CN2CC1 OXLBMFRQXNFTPG-UHFFFAOYSA-N 0.000 claims 2
- QSQJJUODTCHKOH-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]ethanone Chemical compound C1CN(C)CCN1C1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C(=CC=CC=2C)Cl)CC1 QSQJJUODTCHKOH-UHFFFAOYSA-N 0.000 claims 2
- JWSKPNAGXDMKEH-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCC(O)(CC2)C=2C=C(C=CC=2)C(F)(F)F)C2=CC=CN2CC1 JWSKPNAGXDMKEH-UHFFFAOYSA-N 0.000 claims 2
- OUCMSXINRFXMIK-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-(2-pyrrolidin-1-ylethyl)acetamide Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)NCCN2CCCC2)C2=CC=CN2CC1 OUCMSXINRFXMIK-UHFFFAOYSA-N 0.000 claims 2
- STSWXTUJWPWIOA-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-(3-morpholin-4-ylpropyl)acetamide Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)NCCCN2CCOCC2)C2=CC=CN2CC1 STSWXTUJWPWIOA-UHFFFAOYSA-N 0.000 claims 2
- FWCHGYXIQJSEIW-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-(3-piperidin-1-ylpropyl)acetamide Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)NCCCN2CCCCC2)C2=CC=CN2CC1 FWCHGYXIQJSEIW-UHFFFAOYSA-N 0.000 claims 2
- NZUIDIXCSHAVSC-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[3-(2,6-dimethylpiperidin-1-yl)propyl]acetamide Chemical compound CC1CCCC(C)N1CCCNC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=C(C)C=CC=C1Cl NZUIDIXCSHAVSC-UHFFFAOYSA-N 0.000 claims 2
- WBTLSXSEGCADNY-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-methyl-n-(2-morpholin-4-yl-1-phenylethyl)acetamide Chemical compound CC=1C=CC=C(Cl)C=1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)N(C)C(C=1C=CC=CC=1)CN1CCOCC1 WBTLSXSEGCADNY-UHFFFAOYSA-N 0.000 claims 2
- IJXNRUNUSNQUQP-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-methyl-n-(2-piperidin-1-ylethyl)acetamide Chemical compound CC=1C=CC=C(Cl)C=1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)N(C)CCN1CCCCC1 IJXNRUNUSNQUQP-UHFFFAOYSA-N 0.000 claims 2
- PWHPVIGGKGMGFQ-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-methyl-n-[2-(4-methylpiperazin-1-yl)-1-phenylethyl]acetamide Chemical compound CC=1C=CC=C(Cl)C=1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)N(C)C(C=1C=CC=CC=1)CN1CCN(C)CC1 PWHPVIGGKGMGFQ-UHFFFAOYSA-N 0.000 claims 2
- LFHFIVMAFJTMOK-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(3,4-dihydro-2h-quinolin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2CC3=CC=C(CN4C5=CC=CC=C5CCC4)C=C3CC2)C2=CC=CN2CC1 LFHFIVMAFJTMOK-UHFFFAOYSA-N 0.000 claims 2
- WFSYCCDMOIISAP-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2CC3=CC=C(CN4CCCCC4)C=C3CC2)C2=CC=CN2CC1 WFSYCCDMOIISAP-UHFFFAOYSA-N 0.000 claims 2
- CEXMGYYTYUDNBL-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2C3=CC=C(CN4CCCC4)C=C3CCC2)C2=CC=CN2CC1 CEXMGYYTYUDNBL-UHFFFAOYSA-N 0.000 claims 2
- WIFPVZYUVBYNDK-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2CC3=CC=C(CN4CCCC4)C=C3CC2)C2=CC=CN2CC1 WIFPVZYUVBYNDK-UHFFFAOYSA-N 0.000 claims 2
- XYFUCJAAXKXCLC-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-[(dimethylamino)methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C1CCC2=CC(CN(C)C)=CC=C2C1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C(Cl)=C1 XYFUCJAAXKXCLC-UHFFFAOYSA-N 0.000 claims 2
- MGQFSDCRWIAUJL-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-[(dimethylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1CC2=CC(CN(C)C)=CC=C2CC1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C(Cl)=C1 MGQFSDCRWIAUJL-UHFFFAOYSA-N 0.000 claims 2
- LKPBLZWYIGUSRR-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-propan-2-ylpiperazin-1-yl)ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC2)C(C)C)C2=CC=CN2CC1 LKPBLZWYIGUSRR-UHFFFAOYSA-N 0.000 claims 2
- AGUWHOGDLTXFAR-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-pyridin-2-ylpiperazin-1-yl)ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC2)C=2N=CC=CC=2)C2=CC=CN2CC1 AGUWHOGDLTXFAR-UHFFFAOYSA-N 0.000 claims 2
- WJVZFRKYYWCHBT-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[2-(pyridin-2-ylmethyl)pyrrolidin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2C(CCC2)CC=2N=CC=CC=2)C2=CC=CN2CC1 WJVZFRKYYWCHBT-UHFFFAOYSA-N 0.000 claims 2
- ZDAWPBXKMLIYHW-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(6-methyl-1h-benzimidazol-2-yl)piperidin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCC(CC2)C=2NC3=CC=C(C)C=C3N=2)C2=CC=CN2CC1 ZDAWPBXKMLIYHW-UHFFFAOYSA-N 0.000 claims 2
- WCRZKDGKTKVHLB-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]ethanone Chemical compound C1=CC(OC)=CC=C1CN1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C(=CC(OC)=CC=2C)C)CC1 WCRZKDGKTKVHLB-UHFFFAOYSA-N 0.000 claims 2
- FOPYALZROPPGCG-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-(3-piperidin-1-ylpropyl)acetamide Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)NCCCN2CCCCC2)C2=CC=CN2CC1 FOPYALZROPPGCG-UHFFFAOYSA-N 0.000 claims 2
- RYFOPDDUGPGZDQ-UHFFFAOYSA-N 2-[2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2C3=CC=C(CN4CCCC4)C=C3CCC2)C2=CC=CN2CC1 RYFOPDDUGPGZDQ-UHFFFAOYSA-N 0.000 claims 2
- GHQJZCXKVYWCAY-UHFFFAOYSA-N 2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)NC(C1=CC=2)CCCC1=CC=2CN1CCCC1 GHQJZCXKVYWCAY-UHFFFAOYSA-N 0.000 claims 2
- BLEWRBPJIXYECC-UHFFFAOYSA-N 2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)NC(CC1=CC=2)CCC1=CC=2CN1CCCC1 BLEWRBPJIXYECC-UHFFFAOYSA-N 0.000 claims 2
- BZELDBADTUKMSB-UHFFFAOYSA-N 2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)NC(CC1=CC=2)CCC1=CC=2CN1CCN(C)CC1 BZELDBADTUKMSB-UHFFFAOYSA-N 0.000 claims 2
- VLTGADHTBHSFKB-UHFFFAOYSA-N 2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-methyl-n-[6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)N(C)C(CC1=CC=2)CCC1=CC=2CN1CCCCC1 VLTGADHTBHSFKB-UHFFFAOYSA-N 0.000 claims 2
- NYOOZRODXIUJNP-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(3,4-dichlorophenyl)piperazin-1-yl]ethanone Chemical compound C1=C(Cl)C(Cl)=CC=C1N1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=CC=CC=2)CC1 NYOOZRODXIUJNP-UHFFFAOYSA-N 0.000 claims 2
- COOQNGKDEBKFMT-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]ethanone Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 COOQNGKDEBKFMT-UHFFFAOYSA-N 0.000 claims 2
- OPSRVYGFFFQNOS-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]ethanone Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=CC=CC=2)CC1 OPSRVYGFFFQNOS-UHFFFAOYSA-N 0.000 claims 2
- KCFUQIOUQMLRDP-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-[(2-fluorophenyl)methyl]piperazin-1-yl]ethanone Chemical compound FC1=CC=CC=C1CN1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=CC=CC=2)CC1 KCFUQIOUQMLRDP-UHFFFAOYSA-N 0.000 claims 2
- ZTCUTJOCWBXGCG-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]ethanone Chemical compound C1=CC(OC)=CC=C1CN1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=CC=CC=2)CC1 ZTCUTJOCWBXGCG-UHFFFAOYSA-N 0.000 claims 2
- VDVIMJSGRJPNDQ-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-[(4-methylphenyl)methyl]piperazin-1-yl]ethanone Chemical compound C1=CC(C)=CC=C1CN1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=CC=CC=2)CC1 VDVIMJSGRJPNDQ-UHFFFAOYSA-N 0.000 claims 2
- IDIWYDKRGMZRFM-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]ethanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=CC=CC=2)CC1 IDIWYDKRGMZRFM-UHFFFAOYSA-N 0.000 claims 2
- YWCRAPMTSYCGSO-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[(1-benzylpiperidin-3-yl)methyl]acetamide Chemical compound C1CCN(CC=2C=CC=CC=2)CC1CNC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 YWCRAPMTSYCGSO-UHFFFAOYSA-N 0.000 claims 2
- PWJMYBVGCGMXDX-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[(1-benzylpyrrolidin-3-yl)methyl]acetamide Chemical compound C1CN(CC=2C=CC=CC=2)CC1CNC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 PWJMYBVGCGMXDX-UHFFFAOYSA-N 0.000 claims 2
- KRRKIZSEBXHBAW-UHFFFAOYSA-N 2-[2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(2-fluorophenyl)piperazin-1-yl]ethanone Chemical compound FC1=CC=CC=C1N1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C(=CC(=CC=2)C(F)(F)F)Cl)CC1 KRRKIZSEBXHBAW-UHFFFAOYSA-N 0.000 claims 2
- MVGFKSGSICXPDZ-UHFFFAOYSA-N 2-[2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(6-methyl-1h-benzimidazol-2-yl)piperidin-1-yl]ethanone Chemical compound N=1C2=CC(C)=CC=C2NC=1C(CC1)CCN1C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl MVGFKSGSICXPDZ-UHFFFAOYSA-N 0.000 claims 2
- SBCNEYDBPFXOJX-UHFFFAOYSA-N 2-[2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[2-(4-methylpiperazin-1-yl)-1-phenylethyl]acetamide Chemical compound C1CN(C)CCN1CC(C=1C=CC=CC=1)NC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl SBCNEYDBPFXOJX-UHFFFAOYSA-N 0.000 claims 2
- QVNGHIIUHJQKQB-UHFFFAOYSA-N 2-[2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[3-(2,6-dimethylpiperidin-1-yl)propyl]acetamide Chemical compound CC1CCCC(C)N1CCCNC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl QVNGHIIUHJQKQB-UHFFFAOYSA-N 0.000 claims 2
- GJKKCNIJKVNQBR-UHFFFAOYSA-N 2-[4-[2-[2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetyl]-1,4-diazepan-1-yl]pyridine-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)N1C(CC(=O)N2CCN(CCC2)C=2C(=CC=CN=2)C#N)C2=CC=CN2CC1 GJKKCNIJKVNQBR-UHFFFAOYSA-N 0.000 claims 2
- AYSKCJBWVUYALK-UHFFFAOYSA-N 2-[[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-(3-pyridin-4-yloxypyrrolidin-1-yl)ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CC(CC2)OC=2C=CN=CC=2)C2=CC=CN2CC1 AYSKCJBWVUYALK-UHFFFAOYSA-N 0.000 claims 2
- ABTZXPYNMJFEEL-UHFFFAOYSA-N 2-[[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-(4-pyridin-4-ylpiperidin-1-yl)ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCC(CC2)C=2C=CN=CC=2)C2=CC=CN2CC1 ABTZXPYNMJFEEL-UHFFFAOYSA-N 0.000 claims 2
- MQRWNERQJVZWNN-UHFFFAOYSA-N 2-[[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-[4-(pyridin-4-ylmethyl)piperidin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCC(CC=3C=CN=CC=3)CC2)C2=CC=CN2CC1 MQRWNERQJVZWNN-UHFFFAOYSA-N 0.000 claims 2
- GKFDENSNOQIQIQ-UHFFFAOYSA-N 2-[[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-[4-pyridin-3-yl-4-(2-pyrrolidin-1-ylethoxy)piperidin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCC(CC2)(OCCN2CCCC2)C=2C=NC=CC=2)C2=CC=CN2CC1 GKFDENSNOQIQIQ-UHFFFAOYSA-N 0.000 claims 2
- XQGSXYRQBMUCIR-UHFFFAOYSA-N 2-[[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-n-[1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl]acetamide Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)NC2CCN(CC2)C=2N=CC(=CC=2)C(F)(F)F)C2=CC=CN2CC1 XQGSXYRQBMUCIR-UHFFFAOYSA-N 0.000 claims 2
- GOEBLHORKBJLMR-UHFFFAOYSA-N 3-[4-[2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetyl]piperazin-1-yl]propanenitrile Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CCC#N)CC2)C2=CC=CN2CC1 GOEBLHORKBJLMR-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- WXEPWGVIJYXIGW-UHFFFAOYSA-N n-[(1-benzylpyrrolidin-3-yl)methyl]-2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)NCC2CN(CC=3C=CC=CC=3)CC2)C2=CC=CN2CC1 WXEPWGVIJYXIGW-UHFFFAOYSA-N 0.000 claims 2
- KWMCACRNIJSTDA-XVPAFAEQSA-N n-[(1r)-1-[4-[(tert-butylamino)methyl]phenyl]ethyl]-2-[2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound N([C@H](C)C=1C=CC(CNC(C)(C)C)=CC=1)C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C=C1 KWMCACRNIJSTDA-XVPAFAEQSA-N 0.000 claims 2
- WJJZLWGKBWQIHN-FDOABKJOSA-N n-[(1r)-6-[(4-fluoropiperidin-1-yl)methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(CC(=O)N[C@H]2C3=CC=C(CN4CCC(F)CC4)C=C3CCC2)C2=CC=CN2CC1 WJJZLWGKBWQIHN-FDOABKJOSA-N 0.000 claims 2
- CGSIQDNQRYTDAP-SCBLGKRXSA-N n-[(1r)-6-[(tert-butylamino)methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(CC(=O)N[C@H]2C3=CC=C(CNC(C)(C)C)C=C3CCC2)C2=CC=CN2CC1 CGSIQDNQRYTDAP-SCBLGKRXSA-N 0.000 claims 2
- TXLALCMNUWTVMG-UHFFFAOYSA-N n-[2-[4-(4,5-dihydro-1h-imidazol-2-yl)phenyl]ethyl]-2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)NCCC(C=C1)=CC=C1C1=NCCN1 TXLALCMNUWTVMG-UHFFFAOYSA-N 0.000 claims 2
- QLBWSKPLQHBFAJ-UHFFFAOYSA-N n-[6-(3,4-dihydro-2h-quinolin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1CCC2=CC=CC=C2N1CC1=CC=C(CC(NC(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C2=CC3=CC=C(C=C3C=C2)OC)CC2)C2=C1 QLBWSKPLQHBFAJ-UHFFFAOYSA-N 0.000 claims 2
- NRGVITFKPZMBAV-UHFFFAOYSA-N n-[6-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)NC2C3=CC=C(CN4CCOCC4)C=C3CCC2)=C1 NRGVITFKPZMBAV-UHFFFAOYSA-N 0.000 claims 2
- AMDJAKFFOHNRPV-UHFFFAOYSA-N n-[6-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)NC2CC3=CC=C(CN4CCOCC4)C=C3CC2)=C1 AMDJAKFFOHNRPV-UHFFFAOYSA-N 0.000 claims 2
- SRNGLSHVRGPWJF-UHFFFAOYSA-N n-[6-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)NC2C3=CC=C(CN4CCCC4)C=C3CCC2)=C1 SRNGLSHVRGPWJF-UHFFFAOYSA-N 0.000 claims 2
- CAKXBJYXKLXOCJ-UHFFFAOYSA-N n-[6-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)NC2CC3=CC=C(CN4CCCC4)C=C3CC2)=C1 CAKXBJYXKLXOCJ-UHFFFAOYSA-N 0.000 claims 2
- JGYZUTXHMZSRLP-UHFFFAOYSA-N n-[6-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1CN(C)CCN1CC1=CC=C(CC(CC2)NC(=O)CC3C4=CC=CN4CCN3S(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)C2=C1 JGYZUTXHMZSRLP-UHFFFAOYSA-N 0.000 claims 2
- BOJVQMDGKUYRDD-UHFFFAOYSA-N n-[6-[(dimethylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1CC2=CC(CN(C)C)=CC=C2CC1NC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC2=CC=C(OC)C=C2C=C1 BOJVQMDGKUYRDD-UHFFFAOYSA-N 0.000 claims 2
- CQFZOADLEINMNB-UHFFFAOYSA-N n-[6-[(tert-butylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1CC2=CC(CNC(C)(C)C)=CC=C2CC1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 CQFZOADLEINMNB-UHFFFAOYSA-N 0.000 claims 2
- ITMWTNOEIPOHLC-UHFFFAOYSA-N n-[6-[[tert-butyl(methyl)amino]methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1CCC2=CC(CN(C)C(C)(C)C)=CC=C2C1NC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC2=CC=C(OC)C=C2C=C1 ITMWTNOEIPOHLC-UHFFFAOYSA-N 0.000 claims 2
- QKUALTBSTPHOOB-UHFFFAOYSA-N n-[6-[[tert-butyl(methyl)amino]methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1CC2=CC(CN(C)C(C)(C)C)=CC=C2CC1NC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC2=CC=C(OC)C=C2C=C1 QKUALTBSTPHOOB-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- OKIXHHXHMBUKEC-UHFFFAOYSA-N 1-(4-pyridin-4-yloxypiperidin-1-yl)-2-[[2-[2-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]ethanone Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)N1C(COCC(=O)N2CCC(CC2)OC=2C=CN=CC=2)C2=CC=CN2CC1 OKIXHHXHMBUKEC-UHFFFAOYSA-N 0.000 claims 1
- WMTIJZNNLZNBQK-UHFFFAOYSA-N 1-(7-cyclopropyl-2,7-diazaspiro[4.4]nonan-2-yl)-2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CC3(CN(CC3)C3CC3)CC2)C2=CC=CN2CC1 WMTIJZNNLZNBQK-UHFFFAOYSA-N 0.000 claims 1
- UZMNYLRYKZNBHB-UHFFFAOYSA-N 1-(9-pyridin-4-yl-3,9-diazaspiro[5.5]undecan-3-yl)-2-[[2-[2-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]ethanone Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)N1C(COCC(=O)N2CCC3(CC2)CCN(CC3)C=2C=CN=CC=2)C2=CC=CN2CC1 UZMNYLRYKZNBHB-UHFFFAOYSA-N 0.000 claims 1
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- QLKSWSAYQASJNV-UHFFFAOYSA-N 2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)NC(CC1=CC=2)CCC1=CC=2CN1CCCCC1 QLKSWSAYQASJNV-UHFFFAOYSA-N 0.000 claims 1
- KSLCILLISRDOCL-UHFFFAOYSA-N 2-[2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(3,4-dihydro-1h-isoquinolin-2-yl)ethanone Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)N1C(CC(=O)N2CC3=CC=CC=C3CC2)C2=CC=CN2CC1 KSLCILLISRDOCL-UHFFFAOYSA-N 0.000 claims 1
- SVIZXBPQMQGNGL-UHFFFAOYSA-N 2-[2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-piperidin-1-ylethanone Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)N1C(CC(=O)N2CCCCC2)C2=CC=CN2CC1 SVIZXBPQMQGNGL-UHFFFAOYSA-N 0.000 claims 1
- SZUGSHSBSCVUMN-UHFFFAOYSA-N 2-[[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-(2-pyridin-4-yl-2,8-diazaspiro[4.5]decan-8-yl)ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(COCC(=O)N2CCC3(CN(CC3)C=3C=CN=CC=3)CC2)C2=CC=CN2CC1 SZUGSHSBSCVUMN-UHFFFAOYSA-N 0.000 claims 1
- QYEZODRLNXPRCS-UHFFFAOYSA-N 2-[[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-(4-pyridin-4-yloxypiperidin-1-yl)ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(COCC(=O)N2CCC(CC2)OC=2C=CN=CC=2)C2=CC=CN2CC1 QYEZODRLNXPRCS-UHFFFAOYSA-N 0.000 claims 1
- RUOZVZVHASITMK-UHFFFAOYSA-N 2-[[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-(9-pyridin-4-yl-3,9-diazaspiro[5.5]undecan-3-yl)ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(COCC(=O)N2CCC3(CC2)CCN(CC3)C=2C=CN=CC=2)C2=CC=CN2CC1 RUOZVZVHASITMK-UHFFFAOYSA-N 0.000 claims 1
- NZONMRQPFWYOPE-UHFFFAOYSA-N 2-[[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-(2-pyridin-4-yl-2,8-diazaspiro[4.5]decan-8-yl)ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCC3(CN(CC3)C=3C=CN=CC=3)CC2)C2=CC=CN2CC1 NZONMRQPFWYOPE-UHFFFAOYSA-N 0.000 claims 1
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- YVANISVMAKIGAE-UHFFFAOYSA-N 2-[[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-(9-pyridin-4-yl-3,9-diazaspiro[5.5]undecan-3-yl)ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCC3(CC2)CCN(CC3)C=2C=CN=CC=2)C2=CC=CN2CC1 YVANISVMAKIGAE-UHFFFAOYSA-N 0.000 claims 1
- GBSWYQBLWAQDGM-UHFFFAOYSA-N 2-[[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCN(CC2)C2CCN(C)CC2)C2=CC=CN2CC1 GBSWYQBLWAQDGM-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
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- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
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- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims 1
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- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
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- 206010027599 migraine Diseases 0.000 claims 1
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- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 abstract 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP09003075 | 2009-03-04 | ||
| EP09003075.0 | 2009-03-04 | ||
| PCT/EP2010/001299 WO2010099938A1 (en) | 2009-03-04 | 2010-03-03 | Sulfonylated tetrahydroazolopyrazines and their use as medicinal products |
Publications (1)
| Publication Number | Publication Date |
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| RU2011140061A true RU2011140061A (ru) | 2013-04-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| US (1) | US8158628B2 (https=) |
| EP (1) | EP2403854B1 (https=) |
| JP (1) | JP2012519196A (https=) |
| CN (1) | CN102341398A (https=) |
| AR (1) | AR075539A1 (https=) |
| AU (1) | AU2010220561A1 (https=) |
| BR (1) | BRPI1010533A2 (https=) |
| CA (1) | CA2754330A1 (https=) |
| ES (1) | ES2437108T3 (https=) |
| IL (1) | IL214911A0 (https=) |
| MX (1) | MX305105B (https=) |
| PL (1) | PL2403854T3 (https=) |
| RU (1) | RU2011140061A (https=) |
| TW (1) | TW201035102A (https=) |
| WO (1) | WO2010099938A1 (https=) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2012028331A1 (en) * | 2010-09-03 | 2012-03-08 | Grünenthal GmbH | Substituted tetrahydropyrrolopyrazine derivatives |
| US8754114B2 (en) | 2010-12-22 | 2014-06-17 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| DE102011082013A1 (de) * | 2011-09-01 | 2013-03-07 | Bayer Pharma AG | 6H-Thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine |
| ES2704744T3 (es) | 2012-06-13 | 2019-03-19 | Incyte Holdings Corp | Compuestos tricíclicos sustituidos como inhibidores de FGFR |
| IN2014DN09346A (https=) | 2012-06-13 | 2015-07-17 | Hoffmann La Roche | |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| KR102179599B1 (ko) | 2012-09-25 | 2020-11-19 | 에프. 호프만-라 로슈 아게 | 이환형 유도체 |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| CN103113324B (zh) * | 2013-02-07 | 2015-08-05 | 浙江工业大学 | 一种n-磺酰基取代的四氢吡咯类化合物的制备方法 |
| AR095079A1 (es) | 2013-03-12 | 2015-09-16 | Hoffmann La Roche | Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo |
| EA035095B1 (ru) | 2013-04-19 | 2020-04-27 | Инсайт Холдингс Корпорейшн | Бициклические гетероциклы в качестве ингибиторов fgfr |
| AR098414A1 (es) | 2013-11-14 | 2016-05-26 | Bristol Myers Squibb Co | PIPERAZINAS DE PIRAZOLO SUSTITUIDO COMO INHIBIDORES DE CASEÍNA QUINASA 1 d/e |
| CN105764905B (zh) | 2013-11-26 | 2019-06-07 | 豪夫迈·罗氏有限公司 | 新的八氢-环丁二烯并[1，2-c；3，4-c’]二吡咯-2基 |
| CN106103446B (zh) | 2014-03-26 | 2019-07-30 | 豪夫迈·罗氏有限公司 | 作为自分泌运动因子(atx)和溶血磷脂酸(lpa)生产抑制剂的二环化合物 |
| WO2015144609A1 (en) | 2014-03-26 | 2015-10-01 | F. Hoffmann-La Roche Ag | Condensed [1,4]diazepine compounds as autotaxin (atx) and lysophosphatidic acid (lpa) production inhibitors |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| WO2016134294A1 (en) | 2015-02-20 | 2016-08-25 | Incyte Corporation | Bicyclic heterocycles as fgfr4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| MX373169B (es) | 2015-02-20 | 2020-04-24 | Incyte Holdings Corp | Heterociclos bicíclicos como inhibidores de receptores del factor de crecimiento fibroblástico (fgfr). |
| MA41898A (fr) | 2015-04-10 | 2018-02-13 | Hoffmann La Roche | Dérivés de quinazolinone bicyclique |
| CA2992889A1 (en) | 2015-09-04 | 2017-03-09 | F. Hoffmann-La Roche Ag | Phenoxymethyl derivatives |
| KR20180054830A (ko) | 2015-09-24 | 2018-05-24 | 에프. 호프만-라 로슈 아게 | 오토탁신(atx) 억제제로서의 이환형 화합물 |
| RU2018112230A (ru) | 2015-09-24 | 2019-10-30 | Ф. Хоффманн-Ля Рош Аг | Бициклические соединения в качестве ингибиторов atx |
| CR20180057A (es) | 2015-09-24 | 2018-04-02 | Hoffmann La Roche | Nuevos compuestos biciclicos como inhibidores duales de atx/ca. |
| AU2016328365B2 (en) | 2015-09-24 | 2020-04-23 | F. Hoffmann-La Roche Ag | New bicyclic compounds as dual ATX/CA inhibitors |
| JOP20190024A1 (ar) | 2016-08-26 | 2019-02-19 | Gilead Sciences Inc | مركبات بيروليزين بها استبدال واستخداماتها |
| WO2018167113A1 (en) | 2017-03-16 | 2018-09-20 | F. Hoffmann-La Roche Ag | New bicyclic compounds as atx inhibitors |
| SG11201908560SA (en) | 2017-03-16 | 2019-10-30 | Hoffmann La Roche | Heterocyclic compounds useful as dual atx/ca inhibitors |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| PL3759109T3 (pl) | 2018-02-26 | 2024-03-04 | Gilead Sciences, Inc. | Podstawione związki pirolizyny jako inhibitory replikacji hbv |
| MA52493A (fr) | 2018-05-04 | 2021-03-10 | Incyte Corp | Sels d'un inhibiteur de fgfr |
| CR20200590A (es) | 2018-05-04 | 2021-04-26 | Incyte Corp | Formas sólidas de un inhibidor de fgfr y procesos para prepararlas |
| WO2020185532A1 (en) | 2019-03-08 | 2020-09-17 | Incyte Corporation | Methods of treating cancer with an fgfr inhibitor |
| WO2021007269A1 (en) | 2019-07-09 | 2021-01-14 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| TWI891666B (zh) | 2019-10-14 | 2025-08-01 | 美商英塞特公司 | 作為ｆｇｆｒ抑制劑之雙環雜環 |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| BR112022010664A2 (pt) | 2019-12-04 | 2022-08-16 | Incyte Corp | Derivados de um inibidor de fgfr |
| EP4069696A1 (en) | 2019-12-04 | 2022-10-12 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| WO2021146424A1 (en) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| TW202304459A (zh) | 2021-04-12 | 2023-02-01 | 美商英塞特公司 | 包含ｆｇｆｒ抑制劑及ｎｅｃｔｉｎ－４靶向劑之組合療法 |
| WO2022261159A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| EP4352059A1 (en) | 2021-06-09 | 2024-04-17 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| CN121175287A (zh) * | 2023-03-29 | 2025-12-19 | 安道麦阿甘有限公司 | 用于制备胺中间体的方法 |
| CN119490446A (zh) * | 2024-09-23 | 2025-02-21 | 苏州艾缇克药物化学有限公司 | 一种左旋舒必利的重要中间体(S)-2-Boc-氨甲基吡咯烷的合成方法 |
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| WO2006068928A1 (en) * | 2004-12-20 | 2006-06-29 | Wyeth | Pyrrolo[1,2-a]quinoxalin-5-(4h)-yl)sulfonyls and carbonyls and their use as estrogenic agents |
| WO2007101007A2 (en) | 2006-02-23 | 2007-09-07 | Neurogen Corporation | Aryl sulfonyl heterocycles |
| US8097626B2 (en) * | 2006-04-21 | 2012-01-17 | Glaxosmithkline Llc | IL-8 receptor antagonists |
| WO2007140383A2 (en) | 2006-05-30 | 2007-12-06 | Neurogen Corporation | Spirocyclic sulfonamides and related compounds |
| EP2383267A1 (de) * | 2006-09-29 | 2011-11-02 | Grünenthal GmbH | Substituierte Sulfonamid-Derivate |
| EP2086935A1 (de) | 2006-10-16 | 2009-08-12 | Grünenthal GmbH | Substituierte sulfonamid-derivate als bradykinin 1 rezeptor modulatoren |
| EP2170350B1 (en) * | 2007-06-21 | 2013-09-11 | Cara Therapeutics, Inc. | Substituted imidazoheterocycles |
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- 2010-03-03 PL PL10708496T patent/PL2403854T3/pl unknown
- 2010-03-03 MX MX2011008864A patent/MX305105B/es active IP Right Grant
- 2010-03-03 CN CN2010800106612A patent/CN102341398A/zh active Pending
- 2010-03-03 AU AU2010220561A patent/AU2010220561A1/en not_active Abandoned
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- 2010-03-03 WO PCT/EP2010/001299 patent/WO2010099938A1/en not_active Ceased
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- 2010-03-04 AR ARP100100647A patent/AR075539A1/es not_active Application Discontinuation
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Also Published As
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| BRPI1010533A2 (pt) | 2016-03-15 |
| HK1160450A1 (en) | 2012-08-17 |
| TW201035102A (en) | 2010-10-01 |
| EP2403854A1 (en) | 2012-01-11 |
| AR075539A1 (es) | 2011-04-20 |
| MX305105B (es) | 2012-11-12 |
| US20100234387A1 (en) | 2010-09-16 |
| EP2403854B1 (en) | 2013-09-11 |
| PL2403854T3 (pl) | 2014-02-28 |
| JP2012519196A (ja) | 2012-08-23 |
| US8158628B2 (en) | 2012-04-17 |
| CA2754330A1 (en) | 2010-09-10 |
| CN102341398A (zh) | 2012-02-01 |
| AU2010220561A1 (en) | 2011-10-27 |
| IL214911A0 (en) | 2011-11-30 |
| ES2437108T3 (es) | 2014-01-08 |
| WO2010099938A1 (en) | 2010-09-10 |
| MX2011008864A (es) | 2011-09-15 |
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Legal Events
| Date | Code | Title | Description |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20140624 |