CA2754330A1 - Sulfonylated tetrahydroazolopyrazines and their use as medicinal products - Google Patents

Info

Publication number

CA2754330A1

CA2754330A1 CA2754330A CA2754330A CA2754330A1 CA 2754330 A1 CA2754330 A1 CA 2754330A1 CA 2754330 A CA2754330 A CA 2754330A CA 2754330 A CA2754330 A CA 2754330A CA 2754330 A1 CA2754330 A1 CA 2754330A1

Authority

CA

Canada

Prior art keywords

tetrahydro

pyrazin

methyl

pyrrolo

phenyl

Prior art date

2009-03-04

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 229940126601 medicinal product Drugs 0.000 title claims abstract description 22
• 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 abstract description 18
• 150000001875 compounds Chemical class 0.000 claims abstract description 133
• 238000002360 preparation method Methods 0.000 claims abstract description 11
• -1 O-aryl Chemical group 0.000 claims description 380
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 278
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 184
• 125000001424 substituent group Chemical group 0.000 claims description 170
• 125000003118 aryl group Chemical group 0.000 claims description 162
• 125000001072 heteroaryl group Chemical group 0.000 claims description 154
• 125000000217 alkyl group Chemical group 0.000 claims description 140
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 116
• 239000000203 mixture Substances 0.000 claims description 107
• 125000002947 alkylene group Chemical group 0.000 claims description 104
• 125000004076 pyridyl group Chemical group 0.000 claims description 93
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 92
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
• 125000001544 thienyl group Chemical group 0.000 claims description 59
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 59
• 125000002883 imidazolyl group Chemical group 0.000 claims description 49
• 125000000335 thiazolyl group Chemical group 0.000 claims description 47
• 125000001425 triazolyl group Chemical group 0.000 claims description 47
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 42
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 40
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 38
• 229910052731 fluorine Inorganic materials 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• 229910052801 chlorine Inorganic materials 0.000 claims description 28
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
• 125000003386 piperidinyl group Chemical group 0.000 claims description 26
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 23
• 125000002393 azetidinyl group Chemical group 0.000 claims description 21
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 20
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
• 125000001624 naphthyl group Chemical group 0.000 claims description 18
• 229910052794 bromium Inorganic materials 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
• 208000002193 Pain Diseases 0.000 claims description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
• 229910052740 iodine Inorganic materials 0.000 claims description 13
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 11
• 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 description 11
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• 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 description 10
• 125000002541 furyl group Chemical group 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 201000010099 disease Diseases 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 206010061218 Inflammation Diseases 0.000 claims description 7
• 150000003839 salts Chemical class 0.000 claims description 7
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000005605 benzo group Chemical group 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 150000001923 cyclic compounds Chemical class 0.000 claims description 6
• 230000004054 inflammatory process Effects 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
• 208000008589 Obesity Diseases 0.000 claims description 5
• 206010040070 Septic Shock Diseases 0.000 claims description 5
• 125000004450 alkenylene group Chemical group 0.000 claims description 5
• 208000004296 neuralgia Diseases 0.000 claims description 5
• 208000021722 neuropathic pain Diseases 0.000 claims description 5
• 235000020824 obesity Nutrition 0.000 claims description 5
• 230000036303 septic shock Effects 0.000 claims description 5
• VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 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 description 4
• 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 description 4
• OAXWFEFKSREFQL-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)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(Cl)=CC=C1S(=O)(=O)N1C(CC(=O)NC2CC3=CC=C(CN4CCCCC4)C=C3CC2)C2=CC=CN2CC1 OAXWFEFKSREFQL-UHFFFAOYSA-N 0.000 claims description 4
• GEVJLESKEAQEKQ-UHFFFAOYSA-N 2-[2-(4-chloro-2,5-dimethylphenyl)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(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)NC2CC3=CC=C(CN4CCCCC4)C=C3CC2)=C1C GEVJLESKEAQEKQ-UHFFFAOYSA-N 0.000 claims description 4
• UREZRAMYMMZTRG-UHFFFAOYSA-N 2-[2-(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=CC(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2CC3=CC=C(CN4CCCCC4)C=C3CC2)C2=CC=CN2CC1 UREZRAMYMMZTRG-UHFFFAOYSA-N 0.000 claims description 4
• WZKUMDYNDLJDQM-UHFFFAOYSA-N 2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[5-(piperidin-1-ylmethyl)-2,3-dihydro-1h-inden-2-yl]acetamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)NC(CC1=C2)CC1=CC=C2CN1CCCCC1 WZKUMDYNDLJDQM-UHFFFAOYSA-N 0.000 claims description 4
• OBPQTQGBAZJVBW-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-1-yl]acetamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)NC(C1=CC=2)CCCC1=CC=2CN1CCCCC1 OBPQTQGBAZJVBW-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• HJVAWWSMJNMNHW-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-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 C1CC2=CC(CN3CCCCC3)=CC=C2CC1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 HJVAWWSMJNMNHW-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 208000000094 Chronic Pain Diseases 0.000 claims description 4
• 206010065390 Inflammatory pain Diseases 0.000 claims description 4
• 208000012902 Nervous system disease Diseases 0.000 claims description 4
• 208000025966 Neurological disease Diseases 0.000 claims description 4
• 208000005298 acute pain Diseases 0.000 claims description 4
• 229940121369 angiogenesis inhibitor Drugs 0.000 claims description 4
• 239000004037 angiogenesis inhibitor Substances 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 150000002391 heterocyclic compounds Chemical class 0.000 claims description 4
• 150000003840 hydrochlorides Chemical class 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• SLPWLBLUNCHOTE-UHFFFAOYSA-N n-[6-(piperidin-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(CN4CCCCC4)C=C3CC2)=C1 SLPWLBLUNCHOTE-UHFFFAOYSA-N 0.000 claims description 4
• QAKITTLOFBFJII-UHFFFAOYSA-N n-[6-[(tert-butylamino)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(CNC(C)(C)C)=CC=C2CC1NC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC2=CC=C(OC)C=C2C=C1 QAKITTLOFBFJII-UHFFFAOYSA-N 0.000 claims description 4
• 230000010410 reperfusion Effects 0.000 claims description 4
• 210000002345 respiratory system Anatomy 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• 208000009935 visceral pain Diseases 0.000 claims description 4
• 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 description 3
• SNOGRDXXCIRUDL-UHFFFAOYSA-N 1-(4-ethylpiperazin-1-yl)-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound C1CN(CC)CCN1C(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 SNOGRDXXCIRUDL-UHFFFAOYSA-N 0.000 claims description 3
• UHTGUMITQROTHR-UHFFFAOYSA-N 1-(4-hydroxy-4-pyridin-3-ylpiperidin-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=NC=CC=2)C2=CC=CN2CC1 UHTGUMITQROTHR-UHFFFAOYSA-N 0.000 claims description 3
• PWKFSBCPULESKV-UHFFFAOYSA-N 1-(4-piperidin-1-ylpiperidin-1-yl)-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)N2CCC(CC2)N2CCCCC2)=C1 PWKFSBCPULESKV-UHFFFAOYSA-N 0.000 claims description 3
• GIHLJRCRPNKBBV-UHFFFAOYSA-N 1-(4-pyridin-2-ylpiperazin-1-yl)-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)N2CCN(CC2)C=2N=CC=CC=2)=C1 GIHLJRCRPNKBBV-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• WJMWHRNCLOLWSJ-UHFFFAOYSA-N 1-[4-(2-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=CC=2)F)C2=CC=CN2CC1 WJMWHRNCLOLWSJ-UHFFFAOYSA-N 0.000 claims description 3
• HRSJOGPBNONJRI-UHFFFAOYSA-N 1-[4-(2-fluorophenyl)piperazin-1-yl]-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]ethanone Chemical compound FC1=CC=CC=C1N1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 HRSJOGPBNONJRI-UHFFFAOYSA-N 0.000 claims description 3
• MOYNISCWDJHUQX-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenyl)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=C(Cl)C(Cl)=CC=2)C2=CC=CN2CC1 MOYNISCWDJHUQX-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• QLKIIVJIELYABY-UHFFFAOYSA-N 1-[4-(5-chloro-2-methylphenyl)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=C(Cl)C=2)C)C2=CC=CN2CC1 QLKIIVJIELYABY-UHFFFAOYSA-N 0.000 claims description 3
• XCRQIQFQZPRCMQ-UHFFFAOYSA-N 2-[2-(2,3-dichlorophenyl)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 ClC1=CC=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)NC2CC3=CC=C(CN4CCCCC4)C=C3CC2)=C1Cl XCRQIQFQZPRCMQ-UHFFFAOYSA-N 0.000 claims description 3
• OVTUGESBHWZXTF-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-hydroxy-4-phenylpiperidin-1-yl)ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCC(O)(CC2)C=2C=CC=CC=2)C2=CC=CN2CC1 OVTUGESBHWZXTF-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• HHIMPRMUVCVSLQ-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-pyrimidin-2-ylpiperazin-1-yl)ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC2)C=2N=CC=CN=2)C2=CC=CN2CC1 HHIMPRMUVCVSLQ-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• OQBDLWXQDDJKPX-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(2-hydroxyethyl)piperazin-1-yl]ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CCO)CC2)C2=CC=CN2CC1 OQBDLWXQDDJKPX-UHFFFAOYSA-N 0.000 claims description 3
• SXQYNFDSGPEHMI-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(2-piperidin-1-ylethyl)piperidin-1-yl]ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCC(CCN3CCCCC3)CC2)C2=CC=CN2CC1 SXQYNFDSGPEHMI-UHFFFAOYSA-N 0.000 claims description 3
• BISNRYZCRBDNJQ-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(3-methoxyphenyl)piperazin-1-yl]ethanone Chemical compound COC1=CC=CC(N2CCN(CC2)C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C(=CC=CC=2C)Cl)=C1 BISNRYZCRBDNJQ-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• CZLNPHWGAQEQRM-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)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=C(C)C=CC=C1Cl CZLNPHWGAQEQRM-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• ULVRPWOLNMSMBL-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)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=C(C)C=CC=C1Cl ULVRPWOLNMSMBL-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• BGVWNLURYJYDTF-UHFFFAOYSA-N 2-[2-(4-chloro-2,5-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(2-fluorophenyl)piperazin-1-yl]ethanone Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)N2CCN(CC2)C=2C(=CC=CC=2)F)=C1C BGVWNLURYJYDTF-UHFFFAOYSA-N 0.000 claims description 3
• HGUWVRQPLBHTMB-UHFFFAOYSA-N 2-[2-(4-chloro-2,5-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 N=1C2=CC(C)=CC=C2NC=1C(CC1)CCN1C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC(C)=C(Cl)C=C1C HGUWVRQPLBHTMB-UHFFFAOYSA-N 0.000 claims description 3
• NFPCVUKZCDGGAD-UHFFFAOYSA-N 2-[2-(4-chloro-2,5-dimethylphenyl)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(Cl)C=C1C NFPCVUKZCDGGAD-UHFFFAOYSA-N 0.000 claims description 3
• OQJCXSRJRVXQGG-UHFFFAOYSA-N 2-[2-(4-chloro-2,5-dimethylphenyl)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(Cl)C=C1C OQJCXSRJRVXQGG-UHFFFAOYSA-N 0.000 claims description 3
• PDNZBAMLIMTXQX-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-phenylpiperazin-1-yl)ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC2)C=2C=CC=CC=2)C2=CC=CN2CC1 PDNZBAMLIMTXQX-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• FFBOPEXZYWBVFD-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[2-(piperidin-1-ylmethyl)pyrrolidin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2C(CCC2)CN2CCCCC2)C2=CC=CN2CC1 FFBOPEXZYWBVFD-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• RKACMZNHEIHCST-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(2-piperidin-1-ylethyl)piperidin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCC(CCN3CCCCC3)CC2)C2=CC=CN2CC1 RKACMZNHEIHCST-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• VMWOGLBTEHHQDR-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC2)C=2N=CC(=CC=2)C(F)(F)F)C2=CC=CN2CC1 VMWOGLBTEHHQDR-UHFFFAOYSA-N 0.000 claims description 3
• HUJLSDAXRAVHEK-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-(3-morpholin-4-ylpropyl)acetamide Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)NCCCN2CCOCC2)C2=CC=CN2CC1 HUJLSDAXRAVHEK-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• SIHGAYXDMQIVES-UHFFFAOYSA-N 2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-methyl-n-(2-piperidin-1-ylethyl)acetamide Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N(C)CCN2CCCCC2)C2=CC=CN2CC1 SIHGAYXDMQIVES-UHFFFAOYSA-N 0.000 claims description 3
• KFYZONHFDAZSFI-CSMDKSQMSA-N 2-[2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[(1r)-6-[(2,2,2-trifluoroethylamino)methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(CC(=O)N[C@H]2C3=CC=C(CNCC(F)(F)F)C=C3CCC2)C2=CC=CN2CC1 KFYZONHFDAZSFI-CSMDKSQMSA-N 0.000 claims description 3
• QNISAUSYSWKRPP-UHFFFAOYSA-N 2-[2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2C3=CC=C(CN4CCOCC4)C=C3CCC2)C2=CC=CN2CC1 QNISAUSYSWKRPP-UHFFFAOYSA-N 0.000 claims description 3
• JCXPNOWFHSWWJV-UHFFFAOYSA-N 2-[2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(morpholin-4-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2CC3=CC=C(CN4CCOCC4)C=C3CC2)C2=CC=CN2CC1 JCXPNOWFHSWWJV-UHFFFAOYSA-N 0.000 claims description 3
• LZAAJRZXEBSGCA-UHFFFAOYSA-N 2-[2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(piperidin-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(CN4CCCCC4)C=C3CCC2)C2=CC=CN2CC1 LZAAJRZXEBSGCA-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 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 description 3
• UFEKOKVFVUPSQW-UHFFFAOYSA-N 2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(morpholin-4-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=2CN1CCOCC1 UFEKOKVFVUPSQW-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
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• FRYRWCPYOJIXEW-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-hydroxy-4-phenylpiperidin-1-yl)ethanone Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 FRYRWCPYOJIXEW-UHFFFAOYSA-N 0.000 claims description 3
• YHOUKECTYHZUPL-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-phenylpiperazin-1-yl)ethanone Chemical compound C1CN(C=2C=CC=CC=2)CCN1C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 YHOUKECTYHZUPL-UHFFFAOYSA-N 0.000 claims description 3
• HSLOPZQABBOYJG-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-phenylpiperidin-1-yl)ethanone Chemical compound C1CC(C=2C=CC=CC=2)CCN1C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 HSLOPZQABBOYJG-UHFFFAOYSA-N 0.000 claims description 3
• WHNPDYFXCHJNPJ-AJZOCDQUSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]ethanone Chemical compound N1([C@@H](CCC1)CN1CCCC1)C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 WHNPDYFXCHJNPJ-AJZOCDQUSA-N 0.000 claims description 3
• FFTHSHKRQYZBKK-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-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)CC1 FFTHSHKRQYZBKK-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• OESSCGJTOJFRFS-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(4-methoxyphenyl)piperazin-1-yl]ethanone Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=CC=CC=2)CC1 OESSCGJTOJFRFS-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• MBZVVCWLBXWUOF-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-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=CC=C1 MBZVVCWLBXWUOF-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• XAHJMJOBMZIEQL-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethanone Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=CC=CC=2)CC1 XAHJMJOBMZIEQL-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• JDNNBVBVXAGBLR-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-[2-(2,5-dimethylpyrrol-1-yl)ethyl]piperazin-1-yl]ethanone Chemical compound CC1=CC=C(C)N1CCN1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=CC=CC=2)CC1 JDNNBVBVXAGBLR-UHFFFAOYSA-N 0.000 claims description 3
• ORDAUDRUWJJPGE-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]ethanone Chemical compound ClC1=CC(C(F)(F)F)=CN=C1N1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=CC=CC=2)CC1 ORDAUDRUWJJPGE-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
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• QAMLTAUKQCSVGE-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-(2-pyrrolidin-1-ylethyl)acetamide Chemical compound C1CCCN1CCNC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 QAMLTAUKQCSVGE-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• GJJVGVIYSIYIGF-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-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=CC=C1 GJJVGVIYSIYIGF-UHFFFAOYSA-N 0.000 claims description 3
• NEDYXPYISRYJLE-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-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=CC=C1 NEDYXPYISRYJLE-UHFFFAOYSA-N 0.000 claims description 3
• KFTFXZHILLFXRH-UHFFFAOYSA-N 2-[2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-pyridin-2-ylpiperazin-1-yl)ethanone Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC2)C=2N=CC=CC=2)C2=CC=CN2CC1 KFTFXZHILLFXRH-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• XWVUGFZTQNQTJL-UHFFFAOYSA-N 2-[2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-(4-methoxyphenyl)piperazin-1-yl]ethanone Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C(=CC(=CC=2)C(F)(F)F)Cl)CC1 XWVUGFZTQNQTJL-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• PQUCQDFTSSTUAN-UHFFFAOYSA-N 2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-[(2,4,6-trimethylphenyl)methyl]piperazin-1-yl]ethanone Chemical compound CC1=CC(C)=CC(C)=C1CN1CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 PQUCQDFTSSTUAN-UHFFFAOYSA-N 0.000 claims description 3
• VHAGMXYEDOCGHP-UHFFFAOYSA-N 2-[4-[2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetyl]-1,4-diazepan-1-yl]pyridine-3-carbonitrile Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CCC2)C=2C(=CC=CN=2)C#N)C2=CC=CN2CC1 VHAGMXYEDOCGHP-UHFFFAOYSA-N 0.000 claims description 3
• MAMJXQDYBXUQKM-UHFFFAOYSA-N 2-[4-[2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC2)C=2C(=CC=CN=2)C#N)C2=CC=CN2CC1 MAMJXQDYBXUQKM-UHFFFAOYSA-N 0.000 claims description 3
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• AINZYNWBCBLJES-UHFFFAOYSA-N 2-[4-[2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetyl]-1,4-diazepan-1-yl]pyridine-3-carbonitrile Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CCC2)C=2C(=CC=CN=2)C#N)C2=CC=CN2CC1 AINZYNWBCBLJES-UHFFFAOYSA-N 0.000 claims description 3
• DKGMUPZTEUTLEV-UHFFFAOYSA-N 2-[4-[2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetyl]-1,4-diazepan-1-yl]pyridine-3-carbonitrile Chemical compound C1CCN(C=2C(=CC=CN=2)C#N)CCN1C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 DKGMUPZTEUTLEV-UHFFFAOYSA-N 0.000 claims description 3
• AQROYYLPTDSWPI-UHFFFAOYSA-N 2-[4-[2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)N2CCN(CC2)C=2C(=CC=CN=2)C#N)=C1 AQROYYLPTDSWPI-UHFFFAOYSA-N 0.000 claims description 3
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• 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 description 3
• 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 description 3
• 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 description 3
• WUJVHNXFJGBUIG-UHFFFAOYSA-N 2-[[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-[3-[(4-methylpiperazin-1-yl)methyl]pyrrolidin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CC(CN3CCN(C)CC3)CC2)C2=CC=CN2CC1 WUJVHNXFJGBUIG-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• IRIHJQQQBBTYHI-UHFFFAOYSA-N 2-[[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]methoxy]-1-[4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)piperidin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCC(CC2)N2C3CC(N(C3)C)C2)C2=CC=CN2CC1 IRIHJQQQBBTYHI-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
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• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 2
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• 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
• CAKGRPXRPUWZIW-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]ethanone Chemical compound CC1=CC=CC(Cl)=C1S(=O)(=O)N1C(CC(=O)N2CCN(CC2)C=2C(=CC(=CN=2)C(F)(F)F)Cl)C2=CC=CN2CC1 CAKGRPXRPUWZIW-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
• 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
• DOFGETXVIKPXFM-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-1-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2C3=CC=C(CN4C5=CC=CC=C5CCC4)C=C3CCC2)C2=CC=CN2CC1 DOFGETXVIKPXFM-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
• LLXLZWYBSBPGSJ-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(methylaminomethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C1CCC2=CC(CNC)=CC=C2C1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C(Cl)=C1 LLXLZWYBSBPGSJ-UHFFFAOYSA-N 0.000 claims 2
• ULFCXHHTJTVHNH-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(methylaminomethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1CC2=CC(CNC)=CC=C2CC1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C(Cl)=C1 ULFCXHHTJTVHNH-UHFFFAOYSA-N 0.000 claims 2
• QLGWLNXJJHIVEA-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(morpholin-4-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(CN4CCOCC4)C=C3CCC2)C2=CC=CN2CC1 QLGWLNXJJHIVEA-UHFFFAOYSA-N 0.000 claims 2
• HEZPBCJFLJIMHS-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(morpholin-4-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(CN4CCOCC4)C=C3CC2)C2=CC=CN2CC1 HEZPBCJFLJIMHS-UHFFFAOYSA-N 0.000 claims 2
• CCFITHLLMOESSZ-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-1-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2C3=CC=C(CN4CCCCC4)C=C3CCC2)C2=CC=CN2CC1 CCFITHLLMOESSZ-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
• NFQXJTOOFDKMJC-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C1CN(C)CCN1CC1=CC=C(C(CCC2)NC(=O)CC3C4=CC=CN4CCN3S(=O)(=O)C=3C=C(Cl)C(C)=CC=3)C2=C1 NFQXJTOOFDKMJC-UHFFFAOYSA-N 0.000 claims 2
• JNAARENEAJZORF-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)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 C1CN(C)CCN1CC1=CC=C(CC(CC2)NC(=O)CC3C4=CC=CN4CCN3S(=O)(=O)C=3C=C(Cl)C(C)=CC=3)C2=C1 JNAARENEAJZORF-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
• FREKZZVYRJCPQY-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)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 ClC1=CC=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)NC2CC3=CC=C(CN4CCCCC4)C=C3CC2)=C1 FREKZZVYRJCPQY-UHFFFAOYSA-N 0.000 claims 2
• FDIYGTAVVXKDSH-UHFFFAOYSA-N 2-[2-(4-chloro-2,5-dimethylphenyl)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 C=1C(C)=C(Cl)C=C(C)C=1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)N(C)C(C=1C=CC=CC=1)CN1CCN(C)CC1 FDIYGTAVVXKDSH-UHFFFAOYSA-N 0.000 claims 2
• KDNSBWFCCSQXMT-UHFFFAOYSA-N 2-[2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C1CN(C)CCN1CC1=CC=C(C(CCC2)NC(=O)CC3C4=CC=CN4CCN3S(=O)(=O)C=3C=CC(C)=CC=3)C2=C1 KDNSBWFCCSQXMT-UHFFFAOYSA-N 0.000 claims 2
• FMAXSIFMRJNVLH-UHFFFAOYSA-N 2-[2-(4-methylphenyl)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 C1CN(C)CCN1CC1=CC=C(CC(CC2)NC(=O)CC3C4=CC=CN4CCN3S(=O)(=O)C=3C=CC(C)=CC=3)C2=C1 FMAXSIFMRJNVLH-UHFFFAOYSA-N 0.000 claims 2
• XGBVAQZETOJXKN-UHFFFAOYSA-N 2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(methylaminomethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]acetamide Chemical compound C1=C(OC)C=CC2=CC(S(=O)(=O)N3C(C4=CC=CN4CC3)CC(=O)NC3C4=CC=C(C=C4CCC3)CNC)=CC=C21 XGBVAQZETOJXKN-UHFFFAOYSA-N 0.000 claims 2
• PTTIZOOOASFPMU-UHFFFAOYSA-N 2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(methylaminomethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C1=C(OC)C=CC2=CC(S(=O)(=O)N3C(C4=CC=CN4CC3)CC(=O)NC3CC4=CC=C(C=C4CC3)CNC)=CC=C21 PTTIZOOOASFPMU-UHFFFAOYSA-N 0.000 claims 2
• OFSUQWDEBDTTSQ-UHFFFAOYSA-N 2-[2-(6-methoxynaphthalen-2-yl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-n-[6-(morpholin-4-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=2CN1CCOCC1 OFSUQWDEBDTTSQ-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
• SSKRTCMEAIJPFK-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-1-yl]acetamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)NC(C1=CC=2)CCCC1=CC=2CN1CCN(C)CC1 SSKRTCMEAIJPFK-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
• KRWBRJQVEDRPNX-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-hydroxy-4-pyridin-3-ylpiperidin-1-yl)ethanone Chemical compound C1CC(O)(C=2C=NC=CC=2)CCN1C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 KRWBRJQVEDRPNX-UHFFFAOYSA-N 0.000 claims 2
• HRIHGDGEBTUBHS-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-methyl-2-phenylpiperazin-1-yl)ethanone Chemical compound C1N(C)CCN(C(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C=2C=CC=CC=2)C1C1=CC=CC=C1 HRIHGDGEBTUBHS-UHFFFAOYSA-N 0.000 claims 2
• MVNZBZQBEWDMOD-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-morpholin-4-ylpiperidin-1-yl)ethanone Chemical compound C1CC(N2CCOCC2)CCN1C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 MVNZBZQBEWDMOD-UHFFFAOYSA-N 0.000 claims 2
• GSSUMPLQTQIGPG-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-pyrimidin-2-ylpiperazin-1-yl)ethanone Chemical compound C1CN(C=2N=CC=CN=2)CCN1C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 GSSUMPLQTQIGPG-UHFFFAOYSA-N 0.000 claims 2
• PLZILSOKVBMSCV-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]-1-(4-pyrrolidin-1-ylpiperidin-1-yl)ethanone Chemical compound C1CC(N2CCCC2)CCN1C(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC=C1 PLZILSOKVBMSCV-UHFFFAOYSA-N 0.000 claims 2
• OFZLGIIKQBQLJD-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-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=2)CC1 OFZLGIIKQBQLJD-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
• 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
• HJLQUQZARDQPGO-UHFFFAOYSA-N 2-[4-[2-[2-[3-(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 FC(F)(F)C1=CC=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)N2CCN(CCC2)C=2C(=CC=CN=2)C#N)=C1 HJLQUQZARDQPGO-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
• JHKWMJXVAXABAY-UHFFFAOYSA-N n-[(1-benzylpyrrolidin-3-yl)methyl]-2-[2-(4-chloro-2,5-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)NCC2CN(CC=3C=CC=CC=3)CC2)=C1C JHKWMJXVAXABAY-UHFFFAOYSA-N 0.000 claims 2
• DSIBLWAHXNPVGP-UHFFFAOYSA-N n-[(1-benzylpyrrolidin-3-yl)methyl]-2-[2-(4-methoxy-2,6-dimethylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(CC(=O)NCC2CN(CC=3C=CC=CC=3)CC2)C2=CC=CN2CC1 DSIBLWAHXNPVGP-UHFFFAOYSA-N 0.000 claims 2
• VZPXLRHNMVVDMT-UHFFFAOYSA-N n-[2-(4-methylpiperazin-1-yl)-1-phenylethyl]-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1CN(C)CCN1CC(C=1C=CC=CC=1)NC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 VZPXLRHNMVVDMT-UHFFFAOYSA-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
• SLICANXHZRJLAY-UHFFFAOYSA-N n-[3-(2,6-dimethylpiperidin-1-yl)propyl]-2-[2-[3-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound CC1CCCC(C)N1CCCNC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 SLICANXHZRJLAY-UHFFFAOYSA-N 0.000 claims 2
• JLSUNMJUGQPHTA-UHFFFAOYSA-N n-[6-(3,4-dihydro-2h-quinolin-1-ylmethyl)-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)NC2C3=CC=C(CN4C5=CC=CC=C5CCC4)C=C3CCC2)C2=CC=CN2CC1 JLSUNMJUGQPHTA-UHFFFAOYSA-N 0.000 claims 2
• QTAHXQURGAMONP-UHFFFAOYSA-N n-[6-(3,4-dihydro-2h-quinolin-1-ylmethyl)-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=CC=C2N1CC(C=C1CCC2)=CC=C1C2NC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC2=CC=C(OC)C=C2C=C1 QTAHXQURGAMONP-UHFFFAOYSA-N 0.000 claims 2
• CJXIJUACYWNTET-UHFFFAOYSA-N n-[6-(3,4-dihydro-2h-quinolin-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(CN4C5=CC=CC=C5CCC4)C=C3CCC2)=C1 CJXIJUACYWNTET-UHFFFAOYSA-N 0.000 claims 2
• KHHUJBAITXAEPS-UHFFFAOYSA-N n-[6-(3,4-dihydro-2h-quinolin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-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)NC2CC3=CC=C(CN4C5=CC=CC=C5CCC4)C=C3CC2)C2=CC=CN2CC1 KHHUJBAITXAEPS-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
• JQAQKNOJRSLEIJ-UHFFFAOYSA-N n-[6-(3,4-dihydro-2h-quinolin-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(CN4C5=CC=CC=C5CCC4)C=C3CC2)=C1 JQAQKNOJRSLEIJ-UHFFFAOYSA-N 0.000 claims 2
• AWXXMZPUOUPTGD-UHFFFAOYSA-N n-[6-(8-azabicyclo[3.2.1]octan-8-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2C3=CC=C(CN4C5CCC4CCC5)C=C3CCC2)C2=CC=CN2CC1 AWXXMZPUOUPTGD-UHFFFAOYSA-N 0.000 claims 2
• LCJRKSKQOXXGSH-UHFFFAOYSA-N n-[6-(8-azabicyclo[3.2.1]octan-8-ylmethyl)-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)NC2C3=CC=C(CN4C5CCC4CCC5)C=C3CCC2)C2=CC=CN2CC1 LCJRKSKQOXXGSH-UHFFFAOYSA-N 0.000 claims 2
• XESLCBPBQKVJCB-UHFFFAOYSA-N n-[6-(8-azabicyclo[3.2.1]octan-8-ylmethyl)-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 C1CCC2CCC1N2CC(C=C1CCC2)=CC=C1C2NC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC2=CC=C(OC)C=C2C=C1 XESLCBPBQKVJCB-UHFFFAOYSA-N 0.000 claims 2
• URJUHRPWRAADQI-UHFFFAOYSA-N n-[6-(8-azabicyclo[3.2.1]octan-8-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(CN4C5CCC4CCC5)C=C3CCC2)=C1 URJUHRPWRAADQI-UHFFFAOYSA-N 0.000 claims 2
• DPURYULEKFTGGU-UHFFFAOYSA-N n-[6-(8-azabicyclo[3.2.1]octan-8-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2CC3=CC=C(CN4C5CCC4CCC5)C=C3CC2)C2=CC=CN2CC1 DPURYULEKFTGGU-UHFFFAOYSA-N 0.000 claims 2
• PPAFQNAAKWGXRQ-UHFFFAOYSA-N n-[6-(8-azabicyclo[3.2.1]octan-8-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-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)NC2CC3=CC=C(CN4C5CCC4CCC5)C=C3CC2)C2=CC=CN2CC1 PPAFQNAAKWGXRQ-UHFFFAOYSA-N 0.000 claims 2
• OUKXDYJRFRXUNO-UHFFFAOYSA-N n-[6-(8-azabicyclo[3.2.1]octan-8-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 C1CCC2CCC1N2CC1=CC=C(CC(NC(=O)CC2C3=CC=CN3CCN2S(=O)(=O)C2=CC3=CC=C(C=C3C=C2)OC)CC2)C2=C1 OUKXDYJRFRXUNO-UHFFFAOYSA-N 0.000 claims 2
• QSLLOBIMLCTGRV-UHFFFAOYSA-N n-[6-(8-azabicyclo[3.2.1]octan-8-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(CN4C5CCC4CCC5)C=C3CC2)=C1 QSLLOBIMLCTGRV-UHFFFAOYSA-N 0.000 claims 2
• AGVWWAOLBIMANS-UHFFFAOYSA-N n-[6-(methylaminomethyl)-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 C1CCC2=CC(CNC)=CC=C2C1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C=C1 AGVWWAOLBIMANS-UHFFFAOYSA-N 0.000 claims 2
• STGLZMDVANGYDX-UHFFFAOYSA-N n-[6-(methylaminomethyl)-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 C1CCC2=CC(CNC)=CC=C2C1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 STGLZMDVANGYDX-UHFFFAOYSA-N 0.000 claims 2
• AMHDIJFAHBLMSR-UHFFFAOYSA-N n-[6-(methylaminomethyl)-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)=CC=C2CC1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 AMHDIJFAHBLMSR-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
• ISZNNVVWYXZYFR-UHFFFAOYSA-N n-[6-(piperidin-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(CN4CCCCC4)C=C3CCC2)=C1 ISZNNVVWYXZYFR-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
• WSIIWBIHKZPURP-UHFFFAOYSA-N n-[6-[(4-methylpiperazin-1-yl)methyl]-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 C1CN(C)CCN1CC1=CC=C(C(CCC2)NC(=O)CC3C4=CC=CN4CCN3S(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)C2=C1 WSIIWBIHKZPURP-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
• DOLOTCZSGWKJKA-UHFFFAOYSA-N n-[6-[(benzylamino)methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2C3=CC=C(CNCC=4C=CC=CC=4)C=C3CCC2)C2=CC=CN2CC1 DOLOTCZSGWKJKA-UHFFFAOYSA-N 0.000 claims 2
• YJDVECBICSVKEF-UHFFFAOYSA-N n-[6-[(benzylamino)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 C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)NC(C1=CC=2)CCCC1=CC=2CNCC1=CC=CC=C1 YJDVECBICSVKEF-UHFFFAOYSA-N 0.000 claims 2
• UTWOZIHDSNAGMD-UHFFFAOYSA-N n-[6-[(benzylamino)methyl]-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(CNCC=4C=CC=CC=4)C=C3CCC2)=C1 UTWOZIHDSNAGMD-UHFFFAOYSA-N 0.000 claims 2
• OZQCPWLWPONGKF-UHFFFAOYSA-N n-[6-[(benzylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2CC3=CC=C(CNCC=4C=CC=CC=4)C=C3CC2)C2=CC=CN2CC1 OZQCPWLWPONGKF-UHFFFAOYSA-N 0.000 claims 2
• UXZFJMVZWQMCLZ-UHFFFAOYSA-N n-[6-[(benzylamino)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 C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N1CCN2C=CC=C2C1CC(=O)NC(CC1=CC=2)CCC1=CC=2CNCC1=CC=CC=C1 UXZFJMVZWQMCLZ-UHFFFAOYSA-N 0.000 claims 2
• QKWUXARKIJXYJV-UHFFFAOYSA-N n-[6-[(benzylamino)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 FC(F)(F)C1=CC=CC(S(=O)(=O)N2C(C3=CC=CN3CC2)CC(=O)NC2CC3=CC=C(CNCC=4C=CC=CC=4)C=C3CC2)=C1 QKWUXARKIJXYJV-UHFFFAOYSA-N 0.000 claims 2
• WVWCZYFQQDYCOU-UHFFFAOYSA-N n-[6-[(butan-2-ylamino)methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1CCC2=CC(CNC(C)CC)=CC=C2C1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C(Cl)=C1 WVWCZYFQQDYCOU-UHFFFAOYSA-N 0.000 claims 2
• PEQQBZRYVIYPCM-UHFFFAOYSA-N n-[6-[(butan-2-ylamino)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 C1CCC2=CC(CNC(C)CC)=CC=C2C1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C=C1 PEQQBZRYVIYPCM-UHFFFAOYSA-N 0.000 claims 2
• LHPLRUQOVKFTOL-UHFFFAOYSA-N n-[6-[(butan-2-ylamino)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 C1=C(OC)C=CC2=CC(S(=O)(=O)N3C(C4=CC=CN4CC3)CC(=O)NC3C4=CC=C(C=C4CCC3)CNC(C)CC)=CC=C21 LHPLRUQOVKFTOL-UHFFFAOYSA-N 0.000 claims 2
• QJIVPMBGHSMGCM-UHFFFAOYSA-N n-[6-[(butan-2-ylamino)methyl]-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 C1CCC2=CC(CNC(C)CC)=CC=C2C1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 QJIVPMBGHSMGCM-UHFFFAOYSA-N 0.000 claims 2
• BZQZKANYNJKJSP-UHFFFAOYSA-N n-[6-[(butan-2-ylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1CC2=CC(CNC(C)CC)=CC=C2CC1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C(Cl)=C1 BZQZKANYNJKJSP-UHFFFAOYSA-N 0.000 claims 2
• VFNLIFUXFSFLSA-UHFFFAOYSA-N n-[6-[(butan-2-ylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-(4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1CC2=CC(CNC(C)CC)=CC=C2CC1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C=C1 VFNLIFUXFSFLSA-UHFFFAOYSA-N 0.000 claims 2
• PVXLEFNPHNDNLR-UHFFFAOYSA-N n-[6-[(butan-2-ylamino)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 C1=C(OC)C=CC2=CC(S(=O)(=O)N3C(C4=CC=CN4CC3)CC(=O)NC3CC4=CC=C(C=C4CC3)CNC(C)CC)=CC=C21 PVXLEFNPHNDNLR-UHFFFAOYSA-N 0.000 claims 2
• NSRBNZVIAGNMII-UHFFFAOYSA-N n-[6-[(butan-2-ylamino)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)CC)=CC=C2CC1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 NSRBNZVIAGNMII-UHFFFAOYSA-N 0.000 claims 2
• UOZBEGRFMHBPOR-UHFFFAOYSA-N n-[6-[(dimethylamino)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)=CC=C2C1NC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC2=CC=C(OC)C=C2C=C1 UOZBEGRFMHBPOR-UHFFFAOYSA-N 0.000 claims 2
• JJCMEJRONFAHHX-UHFFFAOYSA-N n-[6-[(dimethylamino)methyl]-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 C1CCC2=CC(CN(C)C)=CC=C2C1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 JJCMEJRONFAHHX-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
• IVDNRIJPRCINSL-UHFFFAOYSA-N n-[6-[(dimethylamino)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(CN(C)C)=CC=C2CC1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 IVDNRIJPRCINSL-UHFFFAOYSA-N 0.000 claims 2
• QBRBKOZUPFBALO-UHFFFAOYSA-N n-[6-[(tert-butylamino)methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2C3=CC=C(CNC(C)(C)C)C=C3CCC2)C2=CC=CN2CC1 QBRBKOZUPFBALO-UHFFFAOYSA-N 0.000 claims 2
• CECHBEPJQBXHHY-UHFFFAOYSA-N n-[6-[(tert-butylamino)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(CNC(C)(C)C)=CC=C2C1NC(=O)CC1C2=CC=CN2CCN1S(=O)(=O)C1=CC2=CC=C(OC)C=C2C=C1 CECHBEPJQBXHHY-UHFFFAOYSA-N 0.000 claims 2
• ITSROKXOWUNOMO-UHFFFAOYSA-N n-[6-[(tert-butylamino)methyl]-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 C1CCC2=CC(CNC(C)(C)C)=CC=C2C1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 ITSROKXOWUNOMO-UHFFFAOYSA-N 0.000 claims 2
• BCSHBOHLMKSBIH-UHFFFAOYSA-N n-[6-[(tert-butylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-(3-chloro-4-methylphenyl)sulfonyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-1-yl]acetamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1C(CC(=O)NC2CC3=CC=C(CNC(C)(C)C)C=C3CC2)C2=CC=CN2CC1 BCSHBOHLMKSBIH-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
• YOJUBVPCFJLLAH-UHFFFAOYSA-N n-[6-[[tert-butyl(methyl)amino]methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[2-(3-chloro-4-methylphenyl)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)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C(Cl)=C1 YOJUBVPCFJLLAH-UHFFFAOYSA-N 0.000 claims 2
• OLQOAUFMLWSBDX-UHFFFAOYSA-N n-[6-[[tert-butyl(methyl)amino]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 C1CCC2=CC(CN(C)C(C)(C)C)=CC=C2C1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C=C1 OLQOAUFMLWSBDX-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
• XZADDQJASRPANP-UHFFFAOYSA-N n-[6-[[tert-butyl(methyl)amino]methyl]-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 C1CCC2=CC(CN(C)C(C)(C)C)=CC=C2C1NC(=O)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 XZADDQJASRPANP-UHFFFAOYSA-N 0.000 claims 2
• ZGXWJBHAMHKBGC-UHFFFAOYSA-N n-[6-[[tert-butyl(methyl)amino]methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-(3-chloro-4-methylphenyl)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)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C(Cl)=C1 ZGXWJBHAMHKBGC-UHFFFAOYSA-N 0.000 claims 2
• SPYYXMJBODPXHY-UHFFFAOYSA-N n-[6-[[tert-butyl(methyl)amino]methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-2-[2-(4-methylphenyl)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)CC(C1=CC=CN1CC1)N1S(=O)(=O)C1=CC=C(C)C=C1 SPYYXMJBODPXHY-UHFFFAOYSA-N 0.000 claims 2
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• NLUZFMILBQFXCG-UHFFFAOYSA-N tert-butyl n-[6-(3,4-dihydro-2h-quinolin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate Chemical compound C1CCC2=CC=CC=C2N1CC1=CC=C(CC(NC(=O)OC(C)(C)C)CC2)C2=C1 NLUZFMILBQFXCG-UHFFFAOYSA-N 0.000 description 1
• FSTSYFIGTSTRTJ-UHFFFAOYSA-N tert-butyl n-[6-(8-azabicyclo[3.2.1]octan-8-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate Chemical compound C1CCC2CCC1N2CC1=CC=C(CC(NC(=O)OC(C)(C)C)CC2)C2=C1 FSTSYFIGTSTRTJ-UHFFFAOYSA-N 0.000 description 1
• IUHGCKMPBCCRBZ-UHFFFAOYSA-N tert-butyl n-[6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]carbamate Chemical compound C=1C=C2C(NC(=O)OC(C)(C)C)CCCC2=CC=1CN1CCCCC1 IUHGCKMPBCCRBZ-UHFFFAOYSA-N 0.000 description 1
• ZPKKZVPGWNGUEU-UHFFFAOYSA-N tert-butyl n-[6-(piperidine-1-carbonyl)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate Chemical compound C=1C=C2CC(NC(=O)OC(C)(C)C)CCC2=CC=1C(=O)N1CCCCC1 ZPKKZVPGWNGUEU-UHFFFAOYSA-N 0.000 description 1
• AMTAALYYJRKOPO-UHFFFAOYSA-N tert-butyl n-[6-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]carbamate Chemical compound C=1C=C2C(NC(=O)OC(C)(C)C)CCCC2=CC=1CN1CCCC1 AMTAALYYJRKOPO-UHFFFAOYSA-N 0.000 description 1
• TXFOSZNQKKGJRB-UHFFFAOYSA-N tert-butyl n-[6-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate Chemical compound C=1C=C2CC(NC(=O)OC(C)(C)C)CCC2=CC=1CN1CCCC1 TXFOSZNQKKGJRB-UHFFFAOYSA-N 0.000 description 1
• YXRIHNAXKDBKQV-UHFFFAOYSA-N tert-butyl n-[6-[(benzylamino)methyl]-1,2,3,4-tetrahydronaphthalen-1-yl]carbamate Chemical compound C=1C=C2C(NC(=O)OC(C)(C)C)CCCC2=CC=1CNCC1=CC=CC=C1 YXRIHNAXKDBKQV-UHFFFAOYSA-N 0.000 description 1
• IHMLURBWTRRRRB-UHFFFAOYSA-N tert-butyl n-[6-[(benzylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate Chemical compound C=1C=C2CC(NC(=O)OC(C)(C)C)CCC2=CC=1CNCC1=CC=CC=C1 IHMLURBWTRRRRB-UHFFFAOYSA-N 0.000 description 1
• FUIAQXGCNHBBGQ-UHFFFAOYSA-N tert-butyl n-[6-[(dimethylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate Chemical compound C1C(NC(=O)OC(C)(C)C)CCC2=CC(CN(C)C)=CC=C21 FUIAQXGCNHBBGQ-UHFFFAOYSA-N 0.000 description 1
• ZELAOLADGHTPRG-UHFFFAOYSA-N tert-butyl n-[6-[(tert-butylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate Chemical compound C1C(NC(=O)OC(C)(C)C)CCC2=CC(CNC(C)(C)C)=CC=C21 ZELAOLADGHTPRG-UHFFFAOYSA-N 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
• 150000003536 tetrazoles Chemical class 0.000 description 1
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 238000006276 transfer reaction Methods 0.000 description 1
• 150000003852 triazoles Chemical class 0.000 description 1
• 230000003827 upregulation Effects 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1