JP2010513379A5

JP2010513379A5 -

Download PDF

Info

Publication number: JP2010513379A5
Authority: JP; Japan
Prior art keywords: methanone; pyrrolidin; phenyl; propyl; indol
Prior art date: 2007-12-11
Legal status : Granted

Application number

JP2009541988A

Other languages

English (en)

Japanese (ja)

Other versions

JP5394252B2 (ja

JP2010513379A (ja

Filing date

2007-12-11

Publication date

2010-10-14

2007-12-11 Application filed filed Critical

2007-12-11 Priority claimed from PCT/EP2007/063736 external-priority patent/WO2008074703A1/en

2010-04-30 Publication of JP2010513379A publication Critical patent/JP2010513379A/ja

2010-10-14 Publication of JP2010513379A5 publication Critical patent/JP2010513379A5/ja

2014-01-22 Application granted granted Critical

2014-01-22 Publication of JP5394252B2 publication Critical patent/JP5394252B2/ja

Status Active legal-status Critical Current

2027-12-11 Anticipated expiration legal-status Critical

Links

125000000217 alkyl group Chemical group 0.000 claims 37
150000001875 compounds Chemical class 0.000 claims 29
125000003545 alkoxy group Chemical group 0.000 claims 14
-1 2,3-dihydro-indolyl Chemical group 0.000 claims 11
229910052739 hydrogen Inorganic materials 0.000 claims 10
239000001257 hydrogen Substances 0.000 claims 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
125000001475 halogen functional group Chemical group 0.000 claims 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
125000001072 heteroaryl group Chemical group 0.000 claims 5
125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
125000002947 alkylene group Chemical group 0.000 claims 4
125000004076 pyridyl group Chemical group 0.000 claims 4
125000001544 thienyl group Chemical group 0.000 claims 4
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
125000004414 alkyl thio group Chemical group 0.000 claims 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 3
125000004093 cyano group Chemical group *C#N 0.000 claims 3
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 3
125000001041 indolyl group Chemical group 0.000 claims 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
HVLPRTLORBIKNG-AWEZNQCLSA-N (3,4-dichlorophenyl)-[(3s)-3-propylpyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CCC)CCNC1 HVLPRTLORBIKNG-AWEZNQCLSA-N 0.000 claims 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
FEFGXICFKQBCRL-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-quinolin-2-ylmethanone Chemical compound C=1C=C2C=CC=CC2=NC=1C(=O)C1(CCC(C)(C)C)CCNC1 FEFGXICFKQBCRL-UHFFFAOYSA-N 0.000 claims 2
125000004442 acylamino group Chemical group 0.000 claims 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 2
125000005530 alkylenedioxy group Chemical group 0.000 claims 2
125000003118 aryl group Chemical group 0.000 claims 2
125000004104 aryloxy group Chemical group 0.000 claims 2
MVXVYAKCVDQRLW-UHFFFAOYSA-N azain Natural products C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 2
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 2
125000005605 benzo group Chemical group 0.000 claims 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
125000000000 cycloalkoxy group Chemical group 0.000 claims 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
125000000753 cycloalkyl group Chemical group 0.000 claims 2
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
125000004438 haloalkoxy group Chemical group 0.000 claims 2
125000001188 haloalkyl group Chemical group 0.000 claims 2
125000004404 heteroalkyl group Chemical group 0.000 claims 2
125000005553 heteroaryloxy group Chemical group 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims 2
125000001624 naphthyl group Chemical group 0.000 claims 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
125000003226 pyrazolyl group Chemical group 0.000 claims 2
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
150000003839 salts Chemical class 0.000 claims 2
125000003107 substituted aryl group Chemical group 0.000 claims 2
ZFICBGSDUZWVAS-UHFFFAOYSA-N (1,4-dimethylpiperidin-4-yl)-phenylmethanone Chemical compound C1CN(C)CCC1(C)C(=O)C1=CC=CC=C1 ZFICBGSDUZWVAS-UHFFFAOYSA-N 0.000 claims 1
NTWZPANNPLNQHR-UHFFFAOYSA-N (1-methylindol-5-yl)-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C=C2N(C)C=CC2=CC=1C(=O)C1(CCC)CCNCC1 NTWZPANNPLNQHR-UHFFFAOYSA-N 0.000 claims 1
UMQWMUPPGHFSCJ-UHFFFAOYSA-N (2,3-dichlorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=CC(Cl)=C(Cl)C=1C(=O)C1(CCC)CCNC1 UMQWMUPPGHFSCJ-UHFFFAOYSA-N 0.000 claims 1
ANTDDLPHSUPOOE-UHFFFAOYSA-N (2,4-dichlorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C1(CCC)CCNC1 ANTDDLPHSUPOOE-UHFFFAOYSA-N 0.000 claims 1
NTDBMPQAZINKFC-CYBMUJFWSA-N (2-amino-3,4-dichlorophenyl)-[(3r)-3-ethylpyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=C(N)C=1C(=O)[C@]1(CC)CCNC1 NTDBMPQAZINKFC-CYBMUJFWSA-N 0.000 claims 1
NTDBMPQAZINKFC-ZDUSSCGKSA-N (2-amino-3,4-dichlorophenyl)-[(3s)-3-ethylpyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=C(N)C=1C(=O)[C@@]1(CC)CCNC1 NTDBMPQAZINKFC-ZDUSSCGKSA-N 0.000 claims 1
USHBBAXBEFOYRR-UHFFFAOYSA-N (2-amino-3,4-dichlorophenyl)-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=C(N)C=1C(=O)C1(CC(C)C)CCNC1 USHBBAXBEFOYRR-UHFFFAOYSA-N 0.000 claims 1
LPLLJFFJYKVRLO-UHFFFAOYSA-N (2-benzylpyrrolidin-2-yl)-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCCN1 LPLLJFFJYKVRLO-UHFFFAOYSA-N 0.000 claims 1
CAKCAVOBRWUCLQ-UHFFFAOYSA-N (2-butylpyrrolidin-2-yl)-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CCCC)CCCN1 CAKCAVOBRWUCLQ-UHFFFAOYSA-N 0.000 claims 1
FJOCJYDQXSYPFO-UHFFFAOYSA-N (2-butylpyrrolidin-2-yl)-(1h-indol-2-yl)methanone Chemical compound C=1C2=CC=CC=C2NC=1C(=O)C1(CCCC)CCCN1 FJOCJYDQXSYPFO-UHFFFAOYSA-N 0.000 claims 1
LKUWNJZWVCDPOZ-UHFFFAOYSA-N (2-butylpyrrolidin-2-yl)-(3,4-dichlorophenyl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCCC)CCCN1 LKUWNJZWVCDPOZ-UHFFFAOYSA-N 0.000 claims 1
VTFYVELIGYQGIA-UHFFFAOYSA-N (2-propylpyrrolidin-2-yl)-(1h-pyrrolo[2,3-b]pyridin-5-yl)methanone Chemical compound C=1N=C2NC=CC2=CC=1C(=O)C1(CCC)CCCN1 VTFYVELIGYQGIA-UHFFFAOYSA-N 0.000 claims 1
ZXAGAYMXQZCNHX-UHFFFAOYSA-N (3,4-dibromophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Br)C(Br)=CC=1C(=O)C1(CCC)CCNC1 ZXAGAYMXQZCNHX-UHFFFAOYSA-N 0.000 claims 1
PRWNJZXHYVLZRV-UHFFFAOYSA-N (3,4-dichloro-2-fluorophenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=C(F)C=1C(=O)C1(CCC)CCCNC1 PRWNJZXHYVLZRV-UHFFFAOYSA-N 0.000 claims 1
CAOGDUOLYLGMGP-UHFFFAOYSA-N (3,4-dichloro-2-hydroxyphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=C(O)C=1C(=O)C1(CCC)CCNC1 CAOGDUOLYLGMGP-UHFFFAOYSA-N 0.000 claims 1
DHJOELLMAJRZOG-UHFFFAOYSA-N (3,4-dichloro-5-fluorophenyl)-(2-propylpyrrolidin-2-yl)methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCCN1 DHJOELLMAJRZOG-UHFFFAOYSA-N 0.000 claims 1
CVEJMVFCQBMODT-UHFFFAOYSA-N (3,4-dichloro-5-fluorophenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCCNC1 CVEJMVFCQBMODT-UHFFFAOYSA-N 0.000 claims 1
ROTQELJZWHYIHR-UHFFFAOYSA-N (3,4-dichloro-5-fluorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 ROTQELJZWHYIHR-UHFFFAOYSA-N 0.000 claims 1
OGJLYEMGSGPHSJ-UHFFFAOYSA-N (3,4-dichloro-5-fluorophenyl)-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCNCC1 OGJLYEMGSGPHSJ-UHFFFAOYSA-N 0.000 claims 1
BINJCVHVYJSTMI-QGZVFWFLSA-N (3,4-dichloro-5-fluorophenyl)-[(3r)-3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CCC(C)(C)C)CCNC1 BINJCVHVYJSTMI-QGZVFWFLSA-N 0.000 claims 1
LRZJHOSHAUZZIG-MRXNPFEDSA-N (3,4-dichloro-5-fluorophenyl)-[(3r)-3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CCC(C)C)CCNC1 LRZJHOSHAUZZIG-MRXNPFEDSA-N 0.000 claims 1
ROTQELJZWHYIHR-CQSZACIVSA-N (3,4-dichloro-5-fluorophenyl)-[(3r)-3-propylpyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CCC)CCNC1 ROTQELJZWHYIHR-CQSZACIVSA-N 0.000 claims 1
NPUMXBIRHSOHLD-OAHLLOKOSA-N (3,4-dichloro-5-fluorophenyl)-[(3s)-3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CC(C)C)CCNC1 NPUMXBIRHSOHLD-OAHLLOKOSA-N 0.000 claims 1
BINJCVHVYJSTMI-KRWDZBQOSA-N (3,4-dichloro-5-fluorophenyl)-[(3s)-3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CCC(C)(C)C)CCNC1 BINJCVHVYJSTMI-KRWDZBQOSA-N 0.000 claims 1
LRZJHOSHAUZZIG-INIZCTEOSA-N (3,4-dichloro-5-fluorophenyl)-[(3s)-3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CCC(C)C)CCNC1 LRZJHOSHAUZZIG-INIZCTEOSA-N 0.000 claims 1
ROTQELJZWHYIHR-AWEZNQCLSA-N (3,4-dichloro-5-fluorophenyl)-[(3s)-3-propylpyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CCC)CCNC1 ROTQELJZWHYIHR-AWEZNQCLSA-N 0.000 claims 1
NPUMXBIRHSOHLD-UHFFFAOYSA-N (3,4-dichloro-5-fluorophenyl)-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CC(C)C)CCNC1 NPUMXBIRHSOHLD-UHFFFAOYSA-N 0.000 claims 1
BINJCVHVYJSTMI-UHFFFAOYSA-N (3,4-dichloro-5-fluorophenyl)-[3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CCC(C)(C)C)CCNC1 BINJCVHVYJSTMI-UHFFFAOYSA-N 0.000 claims 1
LRZJHOSHAUZZIG-UHFFFAOYSA-N (3,4-dichloro-5-fluorophenyl)-[3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CCC(C)C)CCNC1 LRZJHOSHAUZZIG-UHFFFAOYSA-N 0.000 claims 1
QNDVPHMLVQTPGK-UHFFFAOYSA-N (3,4-dichloro-5-fluorophenyl)-[3-(oxan-4-ylmethyl)pyrrolidin-3-yl]methanone Chemical compound ClC1=C(Cl)C(F)=CC(C(=O)C2(CC3CCOCC3)CNCC2)=C1 QNDVPHMLVQTPGK-UHFFFAOYSA-N 0.000 claims 1
CKDQWZSFDCSOQU-UHFFFAOYSA-N (3,4-dichloro-5-fluorophenyl)-[4-(2-methylpropyl)piperidin-4-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CC(C)C)CCNCC1 CKDQWZSFDCSOQU-UHFFFAOYSA-N 0.000 claims 1
WMMCKKZDQDOLHU-UHFFFAOYSA-N (3,4-dichloro-5-fluorophenyl)-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CCC(C)(C)C)CCNCC1 WMMCKKZDQDOLHU-UHFFFAOYSA-N 0.000 claims 1
QZDDWWUEAABEGS-UHFFFAOYSA-N (3,4-dichloro-5-fluorophenyl)-[4-(3-methylbutyl)piperidin-4-yl]methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CCC(C)C)CCNCC1 QZDDWWUEAABEGS-UHFFFAOYSA-N 0.000 claims 1
ROWOIFGCJAXTNL-UHFFFAOYSA-N (3,4-dichloro-5-methylphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C(C)=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCCNC1 ROWOIFGCJAXTNL-UHFFFAOYSA-N 0.000 claims 1
AREPFYCXWWGMPZ-UHFFFAOYSA-N (3,4-dichlorophenyl)-(2-propylazetidin-2-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCN1 AREPFYCXWWGMPZ-UHFFFAOYSA-N 0.000 claims 1
OPUOOPOTFCXPLL-UHFFFAOYSA-N (3,4-dichlorophenyl)-(2-propylpiperidin-2-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCCCN1 OPUOOPOTFCXPLL-UHFFFAOYSA-N 0.000 claims 1
HWJCHTVVHUINLQ-UHFFFAOYSA-N (3,4-dichlorophenyl)-(2-propylpyrrolidin-2-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCCN1 HWJCHTVVHUINLQ-UHFFFAOYSA-N 0.000 claims 1
SQUZLMXRFZMGGE-UHFFFAOYSA-N (3,4-dichlorophenyl)-(3-propan-2-ylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(C(C)C)CCNC1 SQUZLMXRFZMGGE-UHFFFAOYSA-N 0.000 claims 1
LVBAQWBEQONMLF-UHFFFAOYSA-N (3,4-dichlorophenyl)-(3-propylazetidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CNC1 LVBAQWBEQONMLF-UHFFFAOYSA-N 0.000 claims 1
ZFNRTPJFVBEJML-UHFFFAOYSA-N (3,4-dichlorophenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCCNC1 ZFNRTPJFVBEJML-UHFFFAOYSA-N 0.000 claims 1
HVLPRTLORBIKNG-UHFFFAOYSA-N (3,4-dichlorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 HVLPRTLORBIKNG-UHFFFAOYSA-N 0.000 claims 1
IHEGTQQKDAJEPO-UHFFFAOYSA-N (3,4-dichlorophenyl)-(4,4-dimethoxy-2-propylpyrrolidin-2-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CC(OC)(OC)CN1 IHEGTQQKDAJEPO-UHFFFAOYSA-N 0.000 claims 1
ZURAGJXUDLADFG-UHFFFAOYSA-N (3,4-dichlorophenyl)-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCNCC1 ZURAGJXUDLADFG-UHFFFAOYSA-N 0.000 claims 1
XETLFXAXJFQYRS-UHFFFAOYSA-N (3,4-dichlorophenyl)-(5,5-dimethyl-2-propylpyrrolidin-2-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCC(C)(C)N1 XETLFXAXJFQYRS-UHFFFAOYSA-N 0.000 claims 1
RJIXBQRQCPJOHO-FDQGKXFDSA-N (3,4-dichlorophenyl)-[(1r,4r,5r)-4-(2-methylpropyl)-8-azabicyclo[3.2.1]octan-4-yl]methanone Chemical compound O=C([C@]1(CC(C)C)[C@@]2([H])CC[C@](N2)(CC1)[H])C1=CC=C(Cl)C(Cl)=C1 RJIXBQRQCPJOHO-FDQGKXFDSA-N 0.000 claims 1
YRTXUGSOVSZHJO-PSOPSSQASA-N (3,4-dichlorophenyl)-[(1r,4r,5r)-4-methyl-8-azabicyclo[3.2.1]octan-4-yl]methanone Chemical compound O=C([C@@]1(C)[C@@]2([H])CC[C@](N2)(CC1)[H])C1=CC=C(Cl)C(Cl)=C1 YRTXUGSOVSZHJO-PSOPSSQASA-N 0.000 claims 1
PYHCWORIIXOKNA-XGWLTEMNSA-N (3,4-dichlorophenyl)-[(1r,4r,5r)-4-propyl-8-azabicyclo[3.2.1]octan-4-yl]methanone Chemical compound O=C([C@@]1(CCC)[C@@]2([H])CC[C@](N2)(CC1)[H])C1=CC=C(Cl)C(Cl)=C1 PYHCWORIIXOKNA-XGWLTEMNSA-N 0.000 claims 1
YRTXUGSOVSZHJO-ZBINZKHDSA-N (3,4-dichlorophenyl)-[(1r,4s,5r)-4-methyl-8-azabicyclo[3.2.1]octan-4-yl]methanone Chemical compound O=C([C@]1(C)[C@@]2([H])CC[C@](N2)(CC1)[H])C1=CC=C(Cl)C(Cl)=C1 YRTXUGSOVSZHJO-ZBINZKHDSA-N 0.000 claims 1
PYHCWORIIXOKNA-MJEQTWJJSA-N (3,4-dichlorophenyl)-[(1r,4s,5r)-4-propyl-8-azabicyclo[3.2.1]octan-4-yl]methanone Chemical compound O=C([C@]1(CCC)[C@@]2([H])CC[C@](N2)(CC1)[H])C1=CC=C(Cl)C(Cl)=C1 PYHCWORIIXOKNA-MJEQTWJJSA-N 0.000 claims 1
UFQHROQVLQZXDY-MPYYAJLASA-N (3,4-dichlorophenyl)-[(1r,5s)-3-propyl-8-azabicyclo[3.2.1]octan-3-yl]methanone Chemical compound C([C@]1(CC[C@@](C2)(N1)[H])[H])C2(CCC)C(=O)C1=CC=C(Cl)C(Cl)=C1 UFQHROQVLQZXDY-MPYYAJLASA-N 0.000 claims 1
HWJCHTVVHUINLQ-CQSZACIVSA-N (3,4-dichlorophenyl)-[(2r)-2-propylpyrrolidin-2-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CCC)CCCN1 HWJCHTVVHUINLQ-CQSZACIVSA-N 0.000 claims 1
IZUAGEMMNNINIY-LNUXAPHWSA-N (3,4-dichlorophenyl)-[(2r)-4-hydroxy-2-propylpyrrolidin-2-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CCC)CC(O)CN1 IZUAGEMMNNINIY-LNUXAPHWSA-N 0.000 claims 1
CLWWXQUPXPXANA-JOPIAHFSSA-N (3,4-dichlorophenyl)-[(2r)-4-methoxy-2-propylpyrrolidin-2-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CCC)CC(OC)CN1 CLWWXQUPXPXANA-JOPIAHFSSA-N 0.000 claims 1
IZUAGEMMNNINIY-QMTHXVAHSA-N (3,4-dichlorophenyl)-[(2r,4r)-4-hydroxy-2-propylpyrrolidin-2-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CCC)C[C@@H](O)CN1 IZUAGEMMNNINIY-QMTHXVAHSA-N 0.000 claims 1
HWJCHTVVHUINLQ-AWEZNQCLSA-N (3,4-dichlorophenyl)-[(2s)-2-propylpyrrolidin-2-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CCC)CCCN1 HWJCHTVVHUINLQ-AWEZNQCLSA-N 0.000 claims 1
ASTQCAFHEFNUII-SBNLOKMTSA-N (3,4-dichlorophenyl)-[(2s)-4-fluoro-2-propylpyrrolidin-2-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CCC)CC(F)CN1 ASTQCAFHEFNUII-SBNLOKMTSA-N 0.000 claims 1
IZUAGEMMNNINIY-SBNLOKMTSA-N (3,4-dichlorophenyl)-[(2s)-4-hydroxy-2-propylpyrrolidin-2-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CCC)CC(O)CN1 IZUAGEMMNNINIY-SBNLOKMTSA-N 0.000 claims 1
IZUAGEMMNNINIY-YGRLFVJLSA-N (3,4-dichlorophenyl)-[(2s,4r)-4-hydroxy-2-propylpyrrolidin-2-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CCC)C[C@@H](O)CN1 IZUAGEMMNNINIY-YGRLFVJLSA-N 0.000 claims 1
GMEQNYYMPIZEGY-HNNXBMFYSA-N (3,4-dichlorophenyl)-[(3r)-3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CC(C)C)CCNC1 GMEQNYYMPIZEGY-HNNXBMFYSA-N 0.000 claims 1
IYHIZUCENFBTJG-QGZVFWFLSA-N (3,4-dichlorophenyl)-[(3r)-3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CCC(C)(C)C)CCNC1 IYHIZUCENFBTJG-QGZVFWFLSA-N 0.000 claims 1
UJJNIABVFUJPGK-MRXNPFEDSA-N (3,4-dichlorophenyl)-[(3r)-3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CCC(C)C)CCNC1 UJJNIABVFUJPGK-MRXNPFEDSA-N 0.000 claims 1
ZFNRTPJFVBEJML-OAHLLOKOSA-N (3,4-dichlorophenyl)-[(3r)-3-propylpiperidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CCC)CCCNC1 ZFNRTPJFVBEJML-OAHLLOKOSA-N 0.000 claims 1
HVLPRTLORBIKNG-CQSZACIVSA-N (3,4-dichlorophenyl)-[(3r)-3-propylpyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@]1(CCC)CCNC1 HVLPRTLORBIKNG-CQSZACIVSA-N 0.000 claims 1
GMEQNYYMPIZEGY-OAHLLOKOSA-N (3,4-dichlorophenyl)-[(3s)-3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CC(C)C)CCNC1 GMEQNYYMPIZEGY-OAHLLOKOSA-N 0.000 claims 1
IYHIZUCENFBTJG-KRWDZBQOSA-N (3,4-dichlorophenyl)-[(3s)-3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CCC(C)(C)C)CCNC1 IYHIZUCENFBTJG-KRWDZBQOSA-N 0.000 claims 1
UJJNIABVFUJPGK-INIZCTEOSA-N (3,4-dichlorophenyl)-[(3s)-3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CCC(C)C)CCNC1 UJJNIABVFUJPGK-INIZCTEOSA-N 0.000 claims 1
ZFNRTPJFVBEJML-HNNXBMFYSA-N (3,4-dichlorophenyl)-[(3s)-3-propylpiperidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)[C@@]1(CCC)CCCNC1 ZFNRTPJFVBEJML-HNNXBMFYSA-N 0.000 claims 1
KIKSPYRDONXZNC-UHFFFAOYSA-N (3,4-dichlorophenyl)-[2-(ethoxymethyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(COCC)CCCN1 KIKSPYRDONXZNC-UHFFFAOYSA-N 0.000 claims 1
BJSYIDODUVIOEA-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(2,2-dimethylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CC(C)(C)C)CCNC1 BJSYIDODUVIOEA-UHFFFAOYSA-N 0.000 claims 1
UWFMOUBXKZGALO-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(2-ethoxyethyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCOCC)CCNC1 UWFMOUBXKZGALO-UHFFFAOYSA-N 0.000 claims 1
OHXOQELCMRNMRS-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(2-methoxy-2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CC(C)(C)OC)CCNC1 OHXOQELCMRNMRS-UHFFFAOYSA-N 0.000 claims 1
GMEQNYYMPIZEGY-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CC(C)C)CCNC1 GMEQNYYMPIZEGY-UHFFFAOYSA-N 0.000 claims 1
IYHIZUCENFBTJG-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC(C)(C)C)CCNC1 IYHIZUCENFBTJG-UHFFFAOYSA-N 0.000 claims 1
MLEAIEBGMXIKJX-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(3-methoxy-3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC(C)(C)OC)CCNC1 MLEAIEBGMXIKJX-UHFFFAOYSA-N 0.000 claims 1
YSVFXULBQMKTOR-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(4,4,4-trifluorobutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCCC(F)(F)F)CCNC1 YSVFXULBQMKTOR-UHFFFAOYSA-N 0.000 claims 1
PHPXTAWQBBUSCL-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(ethoxymethyl)piperidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(COCC)CCCNC1 PHPXTAWQBBUSCL-UHFFFAOYSA-N 0.000 claims 1
URMKGDNVNFDPEN-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(ethoxymethyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(COCC)CCNC1 URMKGDNVNFDPEN-UHFFFAOYSA-N 0.000 claims 1
JFOOKHZUHUFATO-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(oxan-4-ylmethyl)pyrrolidin-3-yl]methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C1(CC2CCOCC2)CNCC1 JFOOKHZUHUFATO-UHFFFAOYSA-N 0.000 claims 1
UYINFTNVLIPILJ-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(propan-2-yloxymethyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(COC(C)C)CCNC1 UYINFTNVLIPILJ-UHFFFAOYSA-N 0.000 claims 1
IQVBMGXBFCJSNN-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-(pyrazol-1-ylmethyl)pyrrolidin-3-yl]methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C1(CN2N=CC=C2)CNCC1 IQVBMGXBFCJSNN-UHFFFAOYSA-N 0.000 claims 1
KCPKZYOCEYXBKE-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-[(1-methylcyclopropyl)methyl]pyrrolidin-3-yl]methanone Chemical compound C1CNCC1(C(=O)C=1C=C(Cl)C(Cl)=CC=1)CC1(C)CC1 KCPKZYOCEYXBKE-UHFFFAOYSA-N 0.000 claims 1
AWIIRYGYXUMSSL-UHFFFAOYSA-N (3,4-dichlorophenyl)-[3-[2-(1-methylcyclopropyl)ethyl]pyrrolidin-3-yl]methanone Chemical compound C1CNCC1(C(=O)C=1C=C(Cl)C(Cl)=CC=1)CCC1(C)CC1 AWIIRYGYXUMSSL-UHFFFAOYSA-N 0.000 claims 1
PCLYMRRSOPAQSA-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-(2-methylpropyl)piperidin-4-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CC(C)C)CCNCC1 PCLYMRRSOPAQSA-UHFFFAOYSA-N 0.000 claims 1
VZAYFZGSCLSRHK-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC(C)(C)C)CCNCC1 VZAYFZGSCLSRHK-UHFFFAOYSA-N 0.000 claims 1
NHKDQTKISYDRLT-UHFFFAOYSA-N (3,4-difluorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(F)C(F)=CC=1C(=O)C1(CCC)CCNC1 NHKDQTKISYDRLT-UHFFFAOYSA-N 0.000 claims 1
ZJFPHYCMSOPDHN-UHFFFAOYSA-N (3,5-dichlorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(=O)C1(CCC)CCNC1 ZJFPHYCMSOPDHN-UHFFFAOYSA-N 0.000 claims 1
FJQXECNKSJWGIF-UHFFFAOYSA-N (3-benzyl-1-methylpyrrolidin-3-yl)-(1h-indol-5-yl)methanone Chemical compound C1N(C)CCC1(C(=O)C=1C=C2C=CNC2=CC=1)CC1=CC=CC=C1 FJQXECNKSJWGIF-UHFFFAOYSA-N 0.000 claims 1
GZMVATBMIADACI-UHFFFAOYSA-N (3-benzylazepan-3-yl)-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCCCNC1 GZMVATBMIADACI-UHFFFAOYSA-N 0.000 claims 1
MDLYPVGOCJZPGM-UHFFFAOYSA-N (3-benzylazetidin-3-yl)-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CNC1 MDLYPVGOCJZPGM-UHFFFAOYSA-N 0.000 claims 1
JHBXYVBNWXENQD-UHFFFAOYSA-N (3-benzylpiperidin-3-yl)-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCCNC1 JHBXYVBNWXENQD-UHFFFAOYSA-N 0.000 claims 1
SAHJMWFRKFDFOZ-UHFFFAOYSA-N (3-benzylpyrrolidin-3-yl)-(1-methylindol-5-yl)methanone Chemical compound C=1C=C2N(C)C=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 SAHJMWFRKFDFOZ-UHFFFAOYSA-N 0.000 claims 1
WAJULVXRUKFJIO-UHFFFAOYSA-N (3-benzylpyrrolidin-3-yl)-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 WAJULVXRUKFJIO-UHFFFAOYSA-N 0.000 claims 1
UJJFCWQKOKAKOW-UHFFFAOYSA-N (3-benzylpyrrolidin-3-yl)-(1h-indol-4-yl)methanone Chemical compound C=1C=CC=2NC=CC=2C=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 UJJFCWQKOKAKOW-UHFFFAOYSA-N 0.000 claims 1
LWIZTBGDAFNFMW-UHFFFAOYSA-N (3-benzylpyrrolidin-3-yl)-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 LWIZTBGDAFNFMW-UHFFFAOYSA-N 0.000 claims 1
RXYDDVDRBRSJOO-UHFFFAOYSA-N (3-benzylpyrrolidin-3-yl)-(1h-indol-6-yl)methanone Chemical compound C=1C=C2C=CNC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 RXYDDVDRBRSJOO-UHFFFAOYSA-N 0.000 claims 1
WFPLHAHCHOHVGF-UHFFFAOYSA-N (3-benzylpyrrolidin-3-yl)-(1h-pyrrolo[2,3-b]pyridin-5-yl)methanone Chemical compound C=1N=C2NC=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 WFPLHAHCHOHVGF-UHFFFAOYSA-N 0.000 claims 1
DMHCJFHZKFBCCC-UHFFFAOYSA-N (3-benzylpyrrolidin-3-yl)-(2,3-dihydro-1h-indol-5-yl)methanone Chemical compound C=1C=C2NCCC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 DMHCJFHZKFBCCC-UHFFFAOYSA-N 0.000 claims 1
LYJBMFHICHSVDY-UHFFFAOYSA-N (3-benzylpyrrolidin-3-yl)-(2-methyl-1h-indol-5-yl)methanone Chemical compound C=1C=C2NC(C)=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 LYJBMFHICHSVDY-UHFFFAOYSA-N 0.000 claims 1
IKJHRTXRKHTQPC-UHFFFAOYSA-N (3-benzylpyrrolidin-3-yl)-(3,4-dichlorophenyl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C1(CC=2C=CC=CC=2)CNCC1 IKJHRTXRKHTQPC-UHFFFAOYSA-N 0.000 claims 1
ZOOYCXCRVKSAIY-UHFFFAOYSA-N (3-benzylpyrrolidin-3-yl)-(7-fluoro-1h-indol-5-yl)methanone Chemical compound C=1C=2C=CNC=2C(F)=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 ZOOYCXCRVKSAIY-UHFFFAOYSA-N 0.000 claims 1
XTXCXISZESQSCW-UHFFFAOYSA-N (3-bromo-4-chlorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(Br)=CC=1C(=O)C1(CCC)CCNC1 XTXCXISZESQSCW-UHFFFAOYSA-N 0.000 claims 1
IWKAPLSVGQUCNY-UHFFFAOYSA-N (3-butylpiperidin-3-yl)-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCCC)CCCNC1 IWKAPLSVGQUCNY-UHFFFAOYSA-N 0.000 claims 1
LVSIELCJLBNXMT-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CCCC)CCNC1 LVSIELCJLBNXMT-UHFFFAOYSA-N 0.000 claims 1
SOYJBYUDJDLOJN-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCCC)CCNC1 SOYJBYUDJDLOJN-UHFFFAOYSA-N 0.000 claims 1
SHNKOXMERGUEQO-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(1h-pyrrolo[2,3-b]pyridin-5-yl)methanone Chemical compound C=1N=C2NC=CC2=CC=1C(=O)C1(CCCC)CCNC1 SHNKOXMERGUEQO-UHFFFAOYSA-N 0.000 claims 1
GDCJLKCMSUXLSO-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(3,4-dichloro-5-fluorophenyl)methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CCCC)CCNC1 GDCJLKCMSUXLSO-UHFFFAOYSA-N 0.000 claims 1
NJISTIFKYHTOJU-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(3,4-dichlorophenyl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCCC)CCNC1 NJISTIFKYHTOJU-UHFFFAOYSA-N 0.000 claims 1
XFCPMDUMARATNL-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(3-chloro-5-fluoro-4-hydroxyphenyl)methanone Chemical compound C=1C(F)=C(O)C(Cl)=CC=1C(=O)C1(CCCC)CCNC1 XFCPMDUMARATNL-UHFFFAOYSA-N 0.000 claims 1
LPSMJCQSWXNPNB-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(4,5-dichlorothiophen-2-yl)methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)C1(CCCC)CCNC1 LPSMJCQSWXNPNB-UHFFFAOYSA-N 0.000 claims 1
XDTBLVPNFFKGOO-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(4-fluoro-1-benzothiophen-2-yl)methanone Chemical compound C=1C2=C(F)C=CC=C2SC=1C(=O)C1(CCCC)CCNC1 XDTBLVPNFFKGOO-UHFFFAOYSA-N 0.000 claims 1
WXGSKRGTLFLUOD-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(4-fluoro-1-benzothiophen-3-yl)methanone Chemical compound C=1SC2=CC=CC(F)=C2C=1C(=O)C1(CCCC)CCNC1 WXGSKRGTLFLUOD-UHFFFAOYSA-N 0.000 claims 1
XRRKSGUIQVOGAE-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(5-fluoro-1-benzothiophen-3-yl)methanone Chemical compound C=1SC2=CC=C(F)C=C2C=1C(=O)C1(CCCC)CCNC1 XRRKSGUIQVOGAE-UHFFFAOYSA-N 0.000 claims 1
UJAUYWSIBZGZNR-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(6,7-difluoro-1h-indol-5-yl)methanone Chemical compound C=1C=2C=CNC=2C(F)=C(F)C=1C(=O)C1(CCCC)CCNC1 UJAUYWSIBZGZNR-UHFFFAOYSA-N 0.000 claims 1
DTALWCMRMSTBDC-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(7-fluoro-1-benzothiophen-2-yl)methanone Chemical compound C=1C2=CC=CC(F)=C2SC=1C(=O)C1(CCCC)CCNC1 DTALWCMRMSTBDC-UHFFFAOYSA-N 0.000 claims 1
YJDDJAPLZXXVLT-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(7-fluoro-1-benzothiophen-3-yl)methanone Chemical compound C=1SC2=C(F)C=CC=C2C=1C(=O)C1(CCCC)CCNC1 YJDDJAPLZXXVLT-UHFFFAOYSA-N 0.000 claims 1
INEHYFAMZQPYDY-UHFFFAOYSA-N (3-butylpyrrolidin-3-yl)-(7-fluoro-1h-indol-5-yl)methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(CCCC)CCNC1 INEHYFAMZQPYDY-UHFFFAOYSA-N 0.000 claims 1
NHWXQJNDOAPHNE-UHFFFAOYSA-N (3-chloro-1-benzothiophen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)C1(CCC)CCNC1 NHWXQJNDOAPHNE-UHFFFAOYSA-N 0.000 claims 1
DWMPCKHRRUEIPV-UHFFFAOYSA-N (3-chloro-2-phenoxyphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=CC(Cl)=C(OC=2C=CC=CC=2)C=1C(=O)C1(CCC)CCNC1 DWMPCKHRRUEIPV-UHFFFAOYSA-N 0.000 claims 1
XIWNDCVEATVNQA-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(F)C(Cl)=CC=1C(=O)C1(CCC)CCCNC1 XIWNDCVEATVNQA-UHFFFAOYSA-N 0.000 claims 1
QWIPTXMISMYHEA-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(F)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 QWIPTXMISMYHEA-UHFFFAOYSA-N 0.000 claims 1
MRAXVYUKHVOIPV-UHFFFAOYSA-N (3-chloro-4-hydroxyphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(O)C(Cl)=CC=1C(=O)C1(CCC)CCCNC1 MRAXVYUKHVOIPV-UHFFFAOYSA-N 0.000 claims 1
CRYISKKGLZZMIK-UHFFFAOYSA-N (3-chloro-4-methoxyphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(OC)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 CRYISKKGLZZMIK-UHFFFAOYSA-N 0.000 claims 1
JMDKBGDSLJZSHO-UHFFFAOYSA-N (3-chloro-4-methylphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(C)C(Cl)=CC=1C(=O)C1(CCC)CCCNC1 JMDKBGDSLJZSHO-UHFFFAOYSA-N 0.000 claims 1
GTPHMOHUBYEMLD-UHFFFAOYSA-N (3-chloro-4-methylphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(C)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 GTPHMOHUBYEMLD-UHFFFAOYSA-N 0.000 claims 1
MZGJPVOTOHUEGK-UHFFFAOYSA-N (3-chloro-4-methylphenyl)-[3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C1=C(Cl)C(C)=CC=C1C(=O)C1(CCC(C)(C)C)CNCC1 MZGJPVOTOHUEGK-UHFFFAOYSA-N 0.000 claims 1
UMZWMGKWSBXUTE-UHFFFAOYSA-N (3-chloro-4-methylphenyl)-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C1=C(Cl)C(C)=CC=C1C(=O)C1(CCC(C)(C)C)CCNCC1 UMZWMGKWSBXUTE-UHFFFAOYSA-N 0.000 claims 1
ZIYHMLSUJFLZBK-UHFFFAOYSA-N (3-chloro-4-methylsulfanylphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(SC)C(Cl)=CC=1C(=O)C1(CCC)CCCNC1 ZIYHMLSUJFLZBK-UHFFFAOYSA-N 0.000 claims 1
FNRJICUXZMPPNH-UHFFFAOYSA-N (3-chloro-4-methylsulfonylphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(S(C)(=O)=O)C(Cl)=CC=1C(=O)C1(CCC)CCCNC1 FNRJICUXZMPPNH-UHFFFAOYSA-N 0.000 claims 1
WVEZYHRIXUSYNI-UHFFFAOYSA-N (3-chloro-4-phenoxyphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 WVEZYHRIXUSYNI-UHFFFAOYSA-N 0.000 claims 1
VQMVLUNRRKDLMX-UHFFFAOYSA-N (3-chloro-5-fluorophenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C(F)=CC(Cl)=CC=1C(=O)C1(CCC)CCCNC1 VQMVLUNRRKDLMX-UHFFFAOYSA-N 0.000 claims 1
TUGVCHXXWKRCKS-UHFFFAOYSA-N (3-chlorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=CC(Cl)=CC=1C(=O)C1(CCC)CCNC1 TUGVCHXXWKRCKS-UHFFFAOYSA-N 0.000 claims 1
JMOIWGXYYOOBHY-UHFFFAOYSA-N (3-chlorothiophen-2-yl)-(3-propylpiperidin-3-yl)methanone Chemical compound S1C=CC(Cl)=C1C(=O)C1(CCC)CCCNC1 JMOIWGXYYOOBHY-UHFFFAOYSA-N 0.000 claims 1
XCSLXLQNQWRTLV-UHFFFAOYSA-N (3-cyclopentylpyrrolidin-3-yl)-(3,4-dichlorophenyl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C1(C2CCCC2)CNCC1 XCSLXLQNQWRTLV-UHFFFAOYSA-N 0.000 claims 1
PAFFZDCOAIOJGS-UHFFFAOYSA-N (3-ethoxypyrrolidin-3-yl)-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(OCC)CCNC1 PAFFZDCOAIOJGS-UHFFFAOYSA-N 0.000 claims 1
GAWHCTCSBNGZEF-UHFFFAOYSA-N (3-fluorophenyl)-[4-(2-fluorophenyl)-1-methylpiperidin-4-yl]methanone Chemical compound C1CN(C)CCC1(C=1C(=CC=CC=1)F)C(=O)C1=CC=CC(F)=C1 GAWHCTCSBNGZEF-UHFFFAOYSA-N 0.000 claims 1
JUSZAQXCCNTRHD-UHFFFAOYSA-N (3-methyl-1-benzothiophen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound S1C2=CC=CC=C2C(C)=C1C(=O)C1(CCC)CCNC1 JUSZAQXCCNTRHD-UHFFFAOYSA-N 0.000 claims 1
CDMHCSBOTVRDIK-UHFFFAOYSA-N (3-propylpiperidin-3-yl)-(3,4,5-trichlorophenyl)methanone Chemical compound C=1C(Cl)=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCCNC1 CDMHCSBOTVRDIK-UHFFFAOYSA-N 0.000 claims 1
FNFKZYYQLOGCQA-UHFFFAOYSA-N (3-propylpiperidin-3-yl)-(3,4,5-trifluorophenyl)methanone Chemical compound C=1C(F)=C(F)C(F)=CC=1C(=O)C1(CCC)CCCNC1 FNFKZYYQLOGCQA-UHFFFAOYSA-N 0.000 claims 1
KKFNUQUQZKEVGK-UHFFFAOYSA-N (3-propylpiperidin-3-yl)-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(=O)C1(CCC)CCCNC1 KKFNUQUQZKEVGK-UHFFFAOYSA-N 0.000 claims 1
ZXMKTIRMPGEQMV-UHFFFAOYSA-N (3-propylpyrrolidin-3-yl)-(1,2,3,4-tetrahydroquinolin-6-yl)methanone Chemical compound C=1C=C2NCCCC2=CC=1C(=O)C1(CCC)CCNC1 ZXMKTIRMPGEQMV-UHFFFAOYSA-N 0.000 claims 1
DBVTVFLFPDIEBY-UHFFFAOYSA-N (3-propylpyrrolidin-3-yl)-(3,4,5-trichlorophenyl)methanone Chemical compound C=1C(Cl)=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 DBVTVFLFPDIEBY-UHFFFAOYSA-N 0.000 claims 1
ZSLSLASAYAFEBP-UHFFFAOYSA-N (3-propylpyrrolidin-3-yl)-(3,4,5-trifluorophenyl)methanone Chemical compound C=1C(F)=C(F)C(F)=CC=1C(=O)C1(CCC)CCNC1 ZSLSLASAYAFEBP-UHFFFAOYSA-N 0.000 claims 1
HPRIJZJXXMTYQJ-UHFFFAOYSA-N (3-propylpyrrolidin-3-yl)-[4-(trifluoromethoxy)phenyl]methanone Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(=O)C1(CCC)CCNC1 HPRIJZJXXMTYQJ-UHFFFAOYSA-N 0.000 claims 1
CNBTUIPRJLLZFG-UHFFFAOYSA-N (3-propylpyrrolidin-3-yl)-[7-(trifluoromethyl)-1h-indol-5-yl]methanone Chemical compound C=1C(C(F)(F)F)=C2NC=CC2=CC=1C(=O)C1(CCC)CCNC1 CNBTUIPRJLLZFG-UHFFFAOYSA-N 0.000 claims 1
WYIYLVVXHBPKCS-UHFFFAOYSA-N (3-propylpyrrolidin-3-yl)-quinolin-6-ylmethanone Chemical compound C=1C=C2N=CC=CC2=CC=1C(=O)C1(CCC)CCNC1 WYIYLVVXHBPKCS-UHFFFAOYSA-N 0.000 claims 1
BFYHFKHXEJGOGF-UHFFFAOYSA-N (3-propylpyrrolidin-3-yl)-quinolin-7-ylmethanone Chemical compound C=1C=C2C=CC=NC2=CC=1C(=O)C1(CCC)CCNC1 BFYHFKHXEJGOGF-UHFFFAOYSA-N 0.000 claims 1
OQOBHQZPXLWUFV-UHFFFAOYSA-N (4,5-dichloro-2-fluorophenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C(Cl)=C(Cl)C=C(F)C=1C(=O)C1(CCC)CCCNC1 OQOBHQZPXLWUFV-UHFFFAOYSA-N 0.000 claims 1
FTHBFIPJDZJMDI-UHFFFAOYSA-N (4,5-dichloropyridin-2-yl)-(2-propylpyrrolidin-2-yl)methanone Chemical compound C=1C(Cl)=C(Cl)C=NC=1C(=O)C1(CCC)CCCN1 FTHBFIPJDZJMDI-UHFFFAOYSA-N 0.000 claims 1
YUGUYTAVSHBDTJ-UHFFFAOYSA-N (4,5-dichloropyridin-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C(Cl)=C(Cl)C=NC=1C(=O)C1(CCC)CCNC1 YUGUYTAVSHBDTJ-UHFFFAOYSA-N 0.000 claims 1
PFGKTYZNBTWPPE-UHFFFAOYSA-N (4,5-dichloropyridin-2-yl)-[3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(Cl)=C(Cl)C=NC=1C(=O)C1(CCC(C)(C)C)CCNC1 PFGKTYZNBTWPPE-UHFFFAOYSA-N 0.000 claims 1
USVNKIXNEHOJAS-UHFFFAOYSA-N (4,5-dichlorothiophen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)C1(CCC)CCNC1 USVNKIXNEHOJAS-UHFFFAOYSA-N 0.000 claims 1
LRMQGTHTRGRPGX-UHFFFAOYSA-N (4,5-dichlorothiophen-2-yl)-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)C1(CCC)CCNCC1 LRMQGTHTRGRPGX-UHFFFAOYSA-N 0.000 claims 1
QGDGZCZIKYAEKM-ZDUSSCGKSA-N (4,5-dichlorothiophen-2-yl)-[(3r)-3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)[C@]1(CC(C)C)CCNC1 QGDGZCZIKYAEKM-ZDUSSCGKSA-N 0.000 claims 1
USVNKIXNEHOJAS-GFCCVEGCSA-N (4,5-dichlorothiophen-2-yl)-[(3r)-3-propylpyrrolidin-3-yl]methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)[C@]1(CCC)CCNC1 USVNKIXNEHOJAS-GFCCVEGCSA-N 0.000 claims 1
QGDGZCZIKYAEKM-CYBMUJFWSA-N (4,5-dichlorothiophen-2-yl)-[(3s)-3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)[C@@]1(CC(C)C)CCNC1 QGDGZCZIKYAEKM-CYBMUJFWSA-N 0.000 claims 1
USVNKIXNEHOJAS-LBPRGKRZSA-N (4,5-dichlorothiophen-2-yl)-[(3s)-3-propylpyrrolidin-3-yl]methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)[C@@]1(CCC)CCNC1 USVNKIXNEHOJAS-LBPRGKRZSA-N 0.000 claims 1
QGDGZCZIKYAEKM-UHFFFAOYSA-N (4,5-dichlorothiophen-2-yl)-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)C1(CC(C)C)CCNC1 QGDGZCZIKYAEKM-UHFFFAOYSA-N 0.000 claims 1
AIGSBZFJFSQVPD-UHFFFAOYSA-N (4,5-dichlorothiophen-2-yl)-[3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)C1(CCC(C)(C)C)CCNC1 AIGSBZFJFSQVPD-UHFFFAOYSA-N 0.000 claims 1
AOMBGORCVUVPEO-UHFFFAOYSA-N (4,5-dichlorothiophen-2-yl)-[3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)C1(CCC(C)C)CCNC1 AOMBGORCVUVPEO-UHFFFAOYSA-N 0.000 claims 1
NYCYWINZFKDIQQ-UHFFFAOYSA-N (4,5-dichlorothiophen-2-yl)-[3-(ethoxymethyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)C1(COCC)CCNC1 NYCYWINZFKDIQQ-UHFFFAOYSA-N 0.000 claims 1
KSDZCZADEVZAIX-UHFFFAOYSA-N (4,5-dichlorothiophen-2-yl)-[3-(oxan-4-ylmethyl)pyrrolidin-3-yl]methanone Chemical compound S1C(Cl)=C(Cl)C=C1C(=O)C1(CC2CCOCC2)CNCC1 KSDZCZADEVZAIX-UHFFFAOYSA-N 0.000 claims 1
PLVRLDVZLHJHLZ-UHFFFAOYSA-N (4,5-dichlorothiophen-2-yl)-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)C1(CCC(C)(C)C)CCNCC1 PLVRLDVZLHJHLZ-UHFFFAOYSA-N 0.000 claims 1
TZHAYRHCAHSZFU-UHFFFAOYSA-N (4-amino-3-chloro-5-fluorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C(F)=C(N)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 TZHAYRHCAHSZFU-UHFFFAOYSA-N 0.000 claims 1
UQXMQKOQFXMKRN-UHFFFAOYSA-N (4-amino-3-chloro-5-fluorophenyl)-(4-butylpiperidin-4-yl)methanone Chemical compound C=1C(F)=C(N)C(Cl)=CC=1C(=O)C1(CCCC)CCNCC1 UQXMQKOQFXMKRN-UHFFFAOYSA-N 0.000 claims 1
SNRGNUJTTCOZJL-UHFFFAOYSA-N (4-amino-3-chloro-5-fluorophenyl)-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C(F)=C(N)C(Cl)=CC=1C(=O)C1(CCC)CCNCC1 SNRGNUJTTCOZJL-UHFFFAOYSA-N 0.000 claims 1
QQGYDDXMJJIYOS-UHFFFAOYSA-N (4-amino-3-chloro-5-fluorophenyl)-[2-(propan-2-yloxymethyl)pyrrolidin-2-yl]methanone Chemical compound C=1C(F)=C(N)C(Cl)=CC=1C(=O)C1(COC(C)C)CCCN1 QQGYDDXMJJIYOS-UHFFFAOYSA-N 0.000 claims 1
ZNHRVBRJBDWHBJ-UHFFFAOYSA-N (4-amino-3-chloro-5-fluorophenyl)-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(N)C(Cl)=CC=1C(=O)C1(CC(C)C)CCNC1 ZNHRVBRJBDWHBJ-UHFFFAOYSA-N 0.000 claims 1
NCRGMZUOVRYODH-UHFFFAOYSA-N (4-amino-3-chloro-5-fluorophenyl)-[3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(N)C(Cl)=CC=1C(=O)C1(CCC(C)(C)C)CCNC1 NCRGMZUOVRYODH-UHFFFAOYSA-N 0.000 claims 1
FCUARUZXUCCHFT-UHFFFAOYSA-N (4-amino-3-chloro-5-fluorophenyl)-[3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C(N)C(Cl)=CC=1C(=O)C1(CCC(C)C)CCNC1 FCUARUZXUCCHFT-UHFFFAOYSA-N 0.000 claims 1
URIOSVUTKUFPPO-UHFFFAOYSA-N (4-amino-3-chloro-5-fluorophenyl)-[4-(2-methylpropyl)piperidin-4-yl]methanone Chemical compound C=1C(F)=C(N)C(Cl)=CC=1C(=O)C1(CC(C)C)CCNCC1 URIOSVUTKUFPPO-UHFFFAOYSA-N 0.000 claims 1
RTEKJIXBRXPUBE-UHFFFAOYSA-N (4-amino-3-chloro-5-fluorophenyl)-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C=1C(F)=C(N)C(Cl)=CC=1C(=O)C1(CCC(C)(C)C)CCNCC1 RTEKJIXBRXPUBE-UHFFFAOYSA-N 0.000 claims 1
LDTHWAKBVZMFAU-UHFFFAOYSA-N (4-amino-3-chloro-5-fluorophenyl)-[4-(3-methylbutyl)piperidin-4-yl]methanone Chemical compound C=1C(F)=C(N)C(Cl)=CC=1C(=O)C1(CCC(C)C)CCNCC1 LDTHWAKBVZMFAU-UHFFFAOYSA-N 0.000 claims 1
DOTVHFCLUNRJAA-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-(2-butylpyrrolidin-2-yl)methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CCCC)CCCN1 DOTVHFCLUNRJAA-UHFFFAOYSA-N 0.000 claims 1
WVZMHYCNWMCWBJ-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-(2-propylpyrrolidin-2-yl)methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CCC)CCCN1 WVZMHYCNWMCWBJ-UHFFFAOYSA-N 0.000 claims 1
SYPPAACYAFSSMA-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 SYPPAACYAFSSMA-UHFFFAOYSA-N 0.000 claims 1
YJZSDNAENMFQMH-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-(4-butylpiperidin-4-yl)methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CCCC)CCNCC1 YJZSDNAENMFQMH-UHFFFAOYSA-N 0.000 claims 1
KLFVBHDTQIGGFY-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CCC)CCNCC1 KLFVBHDTQIGGFY-UHFFFAOYSA-N 0.000 claims 1
KSKOKUBPUSATCC-OAHLLOKOSA-N (4-amino-3-chlorophenyl)-[(2r)-2-(2-methylpropyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)[C@]1(CC(C)C)CCCN1 KSKOKUBPUSATCC-OAHLLOKOSA-N 0.000 claims 1
HFJPQKBQGCFBQI-OAHLLOKOSA-N (4-amino-3-chlorophenyl)-[(2r)-2-(propan-2-yloxymethyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)[C@]1(COC(C)C)CCCN1 HFJPQKBQGCFBQI-OAHLLOKOSA-N 0.000 claims 1
KSKOKUBPUSATCC-HNNXBMFYSA-N (4-amino-3-chlorophenyl)-[(2s)-2-(2-methylpropyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)[C@@]1(CC(C)C)CCCN1 KSKOKUBPUSATCC-HNNXBMFYSA-N 0.000 claims 1
HFJPQKBQGCFBQI-HNNXBMFYSA-N (4-amino-3-chlorophenyl)-[(2s)-2-(propan-2-yloxymethyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)[C@@]1(COC(C)C)CCCN1 HFJPQKBQGCFBQI-HNNXBMFYSA-N 0.000 claims 1
APFRQKRCPYHTLD-QGZVFWFLSA-N (4-amino-3-chlorophenyl)-[(3r)-3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)[C@]1(CCC(C)(C)C)CCNC1 APFRQKRCPYHTLD-QGZVFWFLSA-N 0.000 claims 1
GOCXYVWIBZZZJG-MRXNPFEDSA-N (4-amino-3-chlorophenyl)-[(3r)-3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)[C@]1(CCC(C)C)CCNC1 GOCXYVWIBZZZJG-MRXNPFEDSA-N 0.000 claims 1
APFRQKRCPYHTLD-KRWDZBQOSA-N (4-amino-3-chlorophenyl)-[(3s)-3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)[C@@]1(CCC(C)(C)C)CCNC1 APFRQKRCPYHTLD-KRWDZBQOSA-N 0.000 claims 1
GOCXYVWIBZZZJG-INIZCTEOSA-N (4-amino-3-chlorophenyl)-[(3s)-3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)[C@@]1(CCC(C)C)CCNC1 GOCXYVWIBZZZJG-INIZCTEOSA-N 0.000 claims 1
KSKOKUBPUSATCC-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[2-(2-methylpropyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CC(C)C)CCCN1 KSKOKUBPUSATCC-UHFFFAOYSA-N 0.000 claims 1
OQKSAEPPIZZEIY-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[2-(3,3-dimethylbutyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CCC(C)(C)C)CCCN1 OQKSAEPPIZZEIY-UHFFFAOYSA-N 0.000 claims 1
HVLNUTUNBAUTNM-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[2-(3-methylbutyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CCC(C)C)CCCN1 HVLNUTUNBAUTNM-UHFFFAOYSA-N 0.000 claims 1
BGWVYTXIBKBJMR-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[2-(cyclopropylmethyl)pyrrolidin-2-yl]methanone Chemical compound C1=C(Cl)C(N)=CC=C1C(=O)C1(CC2CC2)NCCC1 BGWVYTXIBKBJMR-UHFFFAOYSA-N 0.000 claims 1
XCOHXEYAWSYCQX-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[2-(ethoxymethyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(COCC)CCCN1 XCOHXEYAWSYCQX-UHFFFAOYSA-N 0.000 claims 1
HFJPQKBQGCFBQI-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[2-(propan-2-yloxymethyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(COC(C)C)CCCN1 HFJPQKBQGCFBQI-UHFFFAOYSA-N 0.000 claims 1
PEDHMSKUDDKNDR-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CC(C)C)CCNC1 PEDHMSKUDDKNDR-UHFFFAOYSA-N 0.000 claims 1
APFRQKRCPYHTLD-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CCC(C)(C)C)CCNC1 APFRQKRCPYHTLD-UHFFFAOYSA-N 0.000 claims 1
GOCXYVWIBZZZJG-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CCC(C)C)CCNC1 GOCXYVWIBZZZJG-UHFFFAOYSA-N 0.000 claims 1
NSCJRMMXSCDYSL-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[4-(2-methylpropyl)piperidin-4-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CC(C)C)CCNCC1 NSCJRMMXSCDYSL-UHFFFAOYSA-N 0.000 claims 1
LKAVQAYVNHGSBF-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CCC(C)(C)C)CCNCC1 LKAVQAYVNHGSBF-UHFFFAOYSA-N 0.000 claims 1
FYUQJKWAYPRQTJ-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-[4-(3-methylbutyl)piperidin-4-yl]methanone Chemical compound C=1C=C(N)C(Cl)=CC=1C(=O)C1(CCC(C)C)CCNCC1 FYUQJKWAYPRQTJ-UHFFFAOYSA-N 0.000 claims 1
ZIHJVSLILCJLCK-UHFFFAOYSA-N (4-amino-3-fluorophenyl)-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C=1C=C(N)C(F)=CC=1C(=O)C1(CCC(C)(C)C)CCNCC1 ZIHJVSLILCJLCK-UHFFFAOYSA-N 0.000 claims 1
AMYIBOVCSKHSFD-UHFFFAOYSA-N (4-benzylpiperidin-4-yl)-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNCC1 AMYIBOVCSKHSFD-UHFFFAOYSA-N 0.000 claims 1
LGCPITGZBZPIIE-UHFFFAOYSA-N (4-benzylpiperidin-4-yl)-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNCC1 LGCPITGZBZPIIE-UHFFFAOYSA-N 0.000 claims 1
LMRPQUPDLBHAKF-UHFFFAOYSA-N (4-benzylpiperidin-4-yl)-(7-chloro-1h-indol-5-yl)methanone Chemical compound C=1C=2C=CNC=2C(Cl)=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNCC1 LMRPQUPDLBHAKF-UHFFFAOYSA-N 0.000 claims 1
RJKIKTJMYXMIBK-UHFFFAOYSA-N (4-benzylpiperidin-4-yl)-(7-fluoro-1h-indol-5-yl)methanone Chemical compound C=1C=2C=CNC=2C(F)=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNCC1 RJKIKTJMYXMIBK-UHFFFAOYSA-N 0.000 claims 1
JZYFYKNFOBWKAN-UHFFFAOYSA-N (4-benzylpiperidin-4-yl)-phenylmethanone Chemical compound C1CNCCC1(CC=1C=CC=CC=1)C(=O)C1=CC=CC=C1 JZYFYKNFOBWKAN-UHFFFAOYSA-N 0.000 claims 1
PYAZXWUFAFEQPI-UHFFFAOYSA-N (4-bromo-3-chloro-5-fluorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C(F)=C(Br)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 PYAZXWUFAFEQPI-UHFFFAOYSA-N 0.000 claims 1
PYXRWCWLCRHQGV-UHFFFAOYSA-N (4-bromo-3-chlorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Br)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 PYXRWCWLCRHQGV-UHFFFAOYSA-N 0.000 claims 1
HXBAGRQWNRNLGU-UHFFFAOYSA-N (4-bromo-3-methylphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Br)C(C)=CC=1C(=O)C1(CCC)CCNC1 HXBAGRQWNRNLGU-UHFFFAOYSA-N 0.000 claims 1
LESLWGRVYMFTCM-UHFFFAOYSA-N (4-butylpiperidin-4-yl)-(1h-indol-2-yl)methanone Chemical compound C=1C2=CC=CC=C2NC=1C(=O)C1(CCCC)CCNCC1 LESLWGRVYMFTCM-UHFFFAOYSA-N 0.000 claims 1
COECAEPPBFXNJR-UHFFFAOYSA-N (4-butylpiperidin-4-yl)-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCCC)CCNCC1 COECAEPPBFXNJR-UHFFFAOYSA-N 0.000 claims 1
DJWQBAFHRDZXBC-UHFFFAOYSA-N (4-butylpiperidin-4-yl)-(3,4-dichloro-5-fluorophenyl)methanone Chemical compound C=1C(F)=C(Cl)C(Cl)=CC=1C(=O)C1(CCCC)CCNCC1 DJWQBAFHRDZXBC-UHFFFAOYSA-N 0.000 claims 1
JENSTMFDAKQRIH-UHFFFAOYSA-N (4-butylpiperidin-4-yl)-(3,4-dichlorophenyl)methanone Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCCC)CCNCC1 JENSTMFDAKQRIH-UHFFFAOYSA-N 0.000 claims 1
NLVFYNNROOCGCL-UHFFFAOYSA-N (4-chloro-1h-indol-2-yl)-[3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C2=C(Cl)C=CC=C2NC=1C(=O)C1(CCC(C)(C)C)CCNC1 NLVFYNNROOCGCL-UHFFFAOYSA-N 0.000 claims 1
DNOZWCURWCSWLX-UHFFFAOYSA-N (4-chloro-2-methylphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(Cl)C=C(C)C=1C(=O)C1(CCC)CCCNC1 DNOZWCURWCSWLX-UHFFFAOYSA-N 0.000 claims 1
XCTWLMZRNKRIBY-UHFFFAOYSA-N (4-chloro-3-cyclopropylphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(C2CC2)=CC=1C(=O)C1(CCC)CCCNC1 XCTWLMZRNKRIBY-UHFFFAOYSA-N 0.000 claims 1
ZTHRMLFWIHZCTB-UHFFFAOYSA-N (4-chloro-3-ethylphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(CC)=CC=1C(=O)C1(CCC)CCNC1 ZTHRMLFWIHZCTB-UHFFFAOYSA-N 0.000 claims 1
CKNLTQAVDHYLGC-UHFFFAOYSA-N (4-chloro-3-fluorophenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(F)=CC=1C(=O)C1(CCC)CCCNC1 CKNLTQAVDHYLGC-UHFFFAOYSA-N 0.000 claims 1
SEEDRERWDJLGNF-UHFFFAOYSA-N (4-chloro-3-fluorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(F)=CC=1C(=O)C1(CCC)CCNC1 SEEDRERWDJLGNF-UHFFFAOYSA-N 0.000 claims 1
RTQFCBRLCAQKAU-UHFFFAOYSA-N (4-chloro-3-methoxyphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(OC)=CC=1C(=O)C1(CCC)CCCNC1 RTQFCBRLCAQKAU-UHFFFAOYSA-N 0.000 claims 1
JIVNUBWSOGPHBG-UHFFFAOYSA-N (4-chloro-3-methoxyphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(OC)=CC=1C(=O)C1(CCC)CCNC1 JIVNUBWSOGPHBG-UHFFFAOYSA-N 0.000 claims 1
XUMIFIXYHLZEJU-UHFFFAOYSA-N (4-chloro-3-methylphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(C)=CC=1C(=O)C1(CCC)CCCNC1 XUMIFIXYHLZEJU-UHFFFAOYSA-N 0.000 claims 1
PFHKLHQSPYMCLN-UHFFFAOYSA-N (4-chloro-3-methylphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(C)=CC=1C(=O)C1(CCC)CCNC1 PFHKLHQSPYMCLN-UHFFFAOYSA-N 0.000 claims 1
UMRQUMQDMSAALW-UHFFFAOYSA-N (4-chloro-3-methylphenyl)-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C1=C(Cl)C(C)=CC(C(=O)C2(CCC(C)(C)C)CCNCC2)=C1 UMRQUMQDMSAALW-UHFFFAOYSA-N 0.000 claims 1
RAOOMVDPLZMUFV-UHFFFAOYSA-N (4-chloro-3-phenoxyphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(OC=2C=CC=CC=2)=CC=1C(=O)C1(CCC)CCNC1 RAOOMVDPLZMUFV-UHFFFAOYSA-N 0.000 claims 1
LDPIPPINNOCUOR-UHFFFAOYSA-N (4-chloro-3-phenoxyphenyl)-[3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(OC=2C=CC=CC=2)=CC=1C(=O)C1(CCC(C)(C)C)CCNC1 LDPIPPINNOCUOR-UHFFFAOYSA-N 0.000 claims 1
AGUUQSUHPOIIJD-UHFFFAOYSA-N (4-chloro-3-phenoxyphenyl)-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C=1C=C(Cl)C(OC=2C=CC=CC=2)=CC=1C(=O)C1(CCC(C)(C)C)CCNCC1 AGUUQSUHPOIIJD-UHFFFAOYSA-N 0.000 claims 1
GAKUPPLSUUUSBY-UHFFFAOYSA-N (4-chloro-3-phenylphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(C=2C=CC=CC=2)=CC=1C(=O)C1(CCC)CCCNC1 GAKUPPLSUUUSBY-UHFFFAOYSA-N 0.000 claims 1
DVMOOIRLFKCIIF-UHFFFAOYSA-N (4-chloro-3-propan-2-yloxyphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(OC(C)C)=CC=1C(=O)C1(CCC)CCNC1 DVMOOIRLFKCIIF-UHFFFAOYSA-N 0.000 claims 1
JHEBXGHITSTDIG-UHFFFAOYSA-N (4-chloro-5-methylthiophen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C(Cl)=C(C)SC=1C(=O)C1(CCC)CCNC1 JHEBXGHITSTDIG-UHFFFAOYSA-N 0.000 claims 1
DTKHHXURZUBPJW-UHFFFAOYSA-N (4-chloronaphthalen-1-yl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(Cl)C2=CC=CC=C2C=1C(=O)C1(CCC)CCCNC1 DTKHHXURZUBPJW-UHFFFAOYSA-N 0.000 claims 1
ZYWWOKNTXBRMEK-UHFFFAOYSA-N (4-chlorophenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1(CCC)CCCNC1 ZYWWOKNTXBRMEK-UHFFFAOYSA-N 0.000 claims 1
BQGNWXPGSXEDMG-UHFFFAOYSA-N (4-chlorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1(CCC)CCNC1 BQGNWXPGSXEDMG-UHFFFAOYSA-N 0.000 claims 1
JDEDIJBHZSOGMV-UHFFFAOYSA-N (4-chlorophenyl)-[4-(2-fluorophenyl)-1-methylpiperidin-4-yl]methanone Chemical compound C1CN(C)CCC1(C=1C(=CC=CC=1)F)C(=O)C1=CC=C(Cl)C=C1 JDEDIJBHZSOGMV-UHFFFAOYSA-N 0.000 claims 1
LTUWHTYZOORDBN-UHFFFAOYSA-N (4-chlorothiophen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C(Cl)=CSC=1C(=O)C1(CCC)CCNC1 LTUWHTYZOORDBN-UHFFFAOYSA-N 0.000 claims 1
VRFGXNYOXHOWIP-UHFFFAOYSA-N (4-fluoro-1-benzothiophen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C2=C(F)C=CC=C2SC=1C(=O)C1(CCC)CCNC1 VRFGXNYOXHOWIP-UHFFFAOYSA-N 0.000 claims 1
WKOABQQTCIVTJA-UHFFFAOYSA-N (4-fluoro-1-benzothiophen-2-yl)-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C2=C(F)C=CC=C2SC=1C(=O)C1(CC(C)C)CCNC1 WKOABQQTCIVTJA-UHFFFAOYSA-N 0.000 claims 1
FEEHXQFOGKFLOP-UHFFFAOYSA-N (4-fluoro-1-benzothiophen-2-yl)-[3-(oxan-4-ylmethyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=2C(F)=CC=CC=2SC=1C(=O)C1(CC2CCOCC2)CCNC1 FEEHXQFOGKFLOP-UHFFFAOYSA-N 0.000 claims 1
JFOQVLJSSXARNQ-UHFFFAOYSA-N (4-fluoro-1h-indol-2-yl)-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C2=C(F)C=CC=C2NC=1C(=O)C1(CCC)CCNCC1 JFOQVLJSSXARNQ-UHFFFAOYSA-N 0.000 claims 1
VXWZWXJGEGFGIK-UHFFFAOYSA-N (4-fluorophenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(F)C=CC=1C(=O)C1(CCC)CCCNC1 VXWZWXJGEGFGIK-UHFFFAOYSA-N 0.000 claims 1
JNAKEFKBTDGJBP-UHFFFAOYSA-N (4-fluorophenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(F)C=CC=1C(=O)C1(CCC)CCNC1 JNAKEFKBTDGJBP-UHFFFAOYSA-N 0.000 claims 1
KNPXVKMXJJYXEH-UHFFFAOYSA-N (4-fluorophenyl)-(4-phenylpiperidin-4-yl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1(C=2C=CC=CC=2)CCNCC1 KNPXVKMXJJYXEH-UHFFFAOYSA-N 0.000 claims 1
YQMCOKQXEKZWJE-UHFFFAOYSA-N (4-fluorophenyl)-[4-(2-fluorophenyl)-1-methylpiperidin-4-yl]methanone Chemical compound C1CN(C)CCC1(C=1C(=CC=CC=1)F)C(=O)C1=CC=C(F)C=C1 YQMCOKQXEKZWJE-UHFFFAOYSA-N 0.000 claims 1
PJVWRILKIKQKAR-UHFFFAOYSA-N (4-iodophenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(I)C=CC=1C(=O)C1(CCC)CCCNC1 PJVWRILKIKQKAR-UHFFFAOYSA-N 0.000 claims 1
JPPPQYFLGUHASI-UHFFFAOYSA-N (4-methoxyphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(OC)C=CC=1C(=O)C1(CCC)CCNC1 JPPPQYFLGUHASI-UHFFFAOYSA-N 0.000 claims 1
UDOYIFXIWKFKKE-UHFFFAOYSA-N (4-methylphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(C)C=CC=1C(=O)C1(CCC)CCCNC1 UDOYIFXIWKFKKE-UHFFFAOYSA-N 0.000 claims 1
IVZZUIGVLUXXLN-UHFFFAOYSA-N (4-phenoxyphenyl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)C1(CCC)CCNC1 IVZZUIGVLUXXLN-UHFFFAOYSA-N 0.000 claims 1
ZGUQTANZJOPGPV-UHFFFAOYSA-N (4-phenylphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1(CCC)CCCNC1 ZGUQTANZJOPGPV-UHFFFAOYSA-N 0.000 claims 1
MHUKJJLIOANDGX-UHFFFAOYSA-N (4-propan-2-ylphenyl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(C(C)C)C=CC=1C(=O)C1(CCC)CCCNC1 MHUKJJLIOANDGX-UHFFFAOYSA-N 0.000 claims 1
SPOGUCVPEXSQTN-UHFFFAOYSA-N (4-propylpiperidin-4-yl)-quinolin-2-ylmethanone Chemical compound C=1C=C2C=CC=CC2=NC=1C(=O)C1(CCC)CCNCC1 SPOGUCVPEXSQTN-UHFFFAOYSA-N 0.000 claims 1
GEAHRQNLMHDCIW-UHFFFAOYSA-N (5,6-dichloropyridin-2-yl)-(2-propylpyrrolidin-2-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=NC=1C(=O)C1(CCC)CCCN1 GEAHRQNLMHDCIW-UHFFFAOYSA-N 0.000 claims 1
ZVMLGQUOGMQTRG-UHFFFAOYSA-N (5,6-dichloropyridin-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(Cl)=NC=1C(=O)C1(CCC)CCNC1 ZVMLGQUOGMQTRG-UHFFFAOYSA-N 0.000 claims 1
WQRMCOZKYZLEFO-UHFFFAOYSA-N (5,6-dichloropyridin-2-yl)-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C(Cl)C(Cl)=NC=1C(=O)C1(CC(C)C)CCNC1 WQRMCOZKYZLEFO-UHFFFAOYSA-N 0.000 claims 1
XEANEEGNRCWLML-UHFFFAOYSA-N (5-chloro-1-benzothiophen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C2=CC(Cl)=CC=C2SC=1C(=O)C1(CCC)CCNC1 XEANEEGNRCWLML-UHFFFAOYSA-N 0.000 claims 1
UBOHBOFFAYUJEO-UHFFFAOYSA-N (5-chloropyridin-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C=NC=1C(=O)C1(CCC)CCNC1 UBOHBOFFAYUJEO-UHFFFAOYSA-N 0.000 claims 1
WLOSKXSEHIAYSF-UHFFFAOYSA-N (5-chloroquinolin-2-yl)-[3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C2C(Cl)=CC=CC2=NC=1C(=O)C1(CCC(C)(C)C)CCNC1 WLOSKXSEHIAYSF-UHFFFAOYSA-N 0.000 claims 1
BJKWQGNJPNIFJE-UHFFFAOYSA-N (5-fluoro-1-benzothiophen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C2=CC(F)=CC=C2SC=1C(=O)C1(CCC)CCNC1 BJKWQGNJPNIFJE-UHFFFAOYSA-N 0.000 claims 1
KDRWWMYQSPUPAQ-UHFFFAOYSA-N (5-fluoro-1-benzothiophen-3-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1SC2=CC=C(F)C=C2C=1C(=O)C1(CCC)CCNC1 KDRWWMYQSPUPAQ-UHFFFAOYSA-N 0.000 claims 1
JVDIEDOQKJYJEQ-UHFFFAOYSA-N (5-fluoro-1-benzothiophen-3-yl)-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1SC2=CC=C(F)C=C2C=1C(=O)C1(CC(C)C)CCNC1 JVDIEDOQKJYJEQ-UHFFFAOYSA-N 0.000 claims 1
XZSHIUCSWJUPFK-UHFFFAOYSA-N (5-fluoro-1h-indol-2-yl)-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C2=CC(F)=CC=C2NC=1C(=O)C1(CCC)CCNCC1 XZSHIUCSWJUPFK-UHFFFAOYSA-N 0.000 claims 1
LBXJBFAHDMJWDW-UHFFFAOYSA-N (5-methyl-1-benzothiophen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C2=CC(C)=CC=C2SC=1C(=O)C1(CCC)CCNC1 LBXJBFAHDMJWDW-UHFFFAOYSA-N 0.000 claims 1
CHZCYIRHOMQPAJ-UHFFFAOYSA-N (6-fluoro-1-benzothiophen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C2=CC=C(F)C=C2SC=1C(=O)C1(CCC)CCNC1 CHZCYIRHOMQPAJ-UHFFFAOYSA-N 0.000 claims 1
IFBWKHRUALUUJS-UHFFFAOYSA-N (6-fluoro-1h-indol-2-yl)-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C2=CC=C(F)C=C2NC=1C(=O)C1(CCC)CCNCC1 IFBWKHRUALUUJS-UHFFFAOYSA-N 0.000 claims 1
CKDQWWDTGAHMNQ-UHFFFAOYSA-N (6-fluoro-1h-indol-5-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=2C=CNC=2C=C(F)C=1C(=O)C1(CCC)CCNC1 CKDQWWDTGAHMNQ-UHFFFAOYSA-N 0.000 claims 1
MWTPTWRUBZCIMK-UHFFFAOYSA-N (6-methoxynaphthalen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C2C=C(OC)C=CC2=CC=1C(=O)C1(CCC)CCNC1 MWTPTWRUBZCIMK-UHFFFAOYSA-N 0.000 claims 1
NXPPJMVAPODSSD-UHFFFAOYSA-N (7-chloro-1h-indol-5-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C(Cl)=C2NC=CC2=CC=1C(=O)C1(CCC)CCNC1 NXPPJMVAPODSSD-UHFFFAOYSA-N 0.000 claims 1
DMDTUVKDTFVGNE-UHFFFAOYSA-N (7-fluoro-1-benzothiophen-2-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C2=CC=CC(F)=C2SC=1C(=O)C1(CCC)CCNC1 DMDTUVKDTFVGNE-UHFFFAOYSA-N 0.000 claims 1
SIKPKEUQJDONDR-UHFFFAOYSA-N (7-fluoro-1-benzothiophen-2-yl)-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C2=CC=CC(F)=C2SC=1C(=O)C1(CC(C)C)CCNC1 SIKPKEUQJDONDR-UHFFFAOYSA-N 0.000 claims 1
IRRMDFSNGIQYJH-UHFFFAOYSA-N (7-fluoro-1-benzothiophen-2-yl)-[3-(oxan-4-ylmethyl)pyrrolidin-3-yl]methanone Chemical compound S1C=2C(F)=CC=CC=2C=C1C(=O)C1(CC2CCOCC2)CCNC1 IRRMDFSNGIQYJH-UHFFFAOYSA-N 0.000 claims 1
GDAPKYRELCAFNY-UHFFFAOYSA-N (7-fluoro-1-benzothiophen-3-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1SC2=C(F)C=CC=C2C=1C(=O)C1(CCC)CCNC1 GDAPKYRELCAFNY-UHFFFAOYSA-N 0.000 claims 1
QMSGWAINCJVQCE-UHFFFAOYSA-N (7-fluoro-1h-indol-2-yl)-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C2=CC=CC(F)=C2NC=1C(=O)C1(CCC)CCNCC1 QMSGWAINCJVQCE-UHFFFAOYSA-N 0.000 claims 1
WTCFDFPSNBMAOR-UHFFFAOYSA-N (7-fluoro-1h-indol-5-yl)-(2-propylpyrrolidin-2-yl)methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(CCC)CCCN1 WTCFDFPSNBMAOR-UHFFFAOYSA-N 0.000 claims 1
KFPHMAQEYMFMJH-UHFFFAOYSA-N (7-fluoro-1h-indol-5-yl)-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(CCC)CCCNC1 KFPHMAQEYMFMJH-UHFFFAOYSA-N 0.000 claims 1
NVHLQOKZIFFNOX-UHFFFAOYSA-N (7-fluoro-1h-indol-5-yl)-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(CCC)CCNC1 NVHLQOKZIFFNOX-UHFFFAOYSA-N 0.000 claims 1
BLKNUASSHDJVDJ-KRWDZBQOSA-N (7-fluoro-1h-indol-5-yl)-[(3r)-3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)[C@]1(CC(C)C)CCNC1 BLKNUASSHDJVDJ-KRWDZBQOSA-N 0.000 claims 1
KIMRUTAJTDBFHO-GOSISDBHSA-N (7-fluoro-1h-indol-5-yl)-[(3r)-3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)[C@]1(CCC(C)C)CCNC1 KIMRUTAJTDBFHO-GOSISDBHSA-N 0.000 claims 1
NVHLQOKZIFFNOX-MRXNPFEDSA-N (7-fluoro-1h-indol-5-yl)-[(3r)-3-propylpyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)[C@]1(CCC)CCNC1 NVHLQOKZIFFNOX-MRXNPFEDSA-N 0.000 claims 1
BLKNUASSHDJVDJ-QGZVFWFLSA-N (7-fluoro-1h-indol-5-yl)-[(3s)-3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)[C@@]1(CC(C)C)CCNC1 BLKNUASSHDJVDJ-QGZVFWFLSA-N 0.000 claims 1
KIMRUTAJTDBFHO-SFHVURJKSA-N (7-fluoro-1h-indol-5-yl)-[(3s)-3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)[C@@]1(CCC(C)C)CCNC1 KIMRUTAJTDBFHO-SFHVURJKSA-N 0.000 claims 1
KFPHMAQEYMFMJH-KRWDZBQOSA-N (7-fluoro-1h-indol-5-yl)-[(3s)-3-propylpiperidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)[C@@]1(CCC)CCCNC1 KFPHMAQEYMFMJH-KRWDZBQOSA-N 0.000 claims 1
NVHLQOKZIFFNOX-INIZCTEOSA-N (7-fluoro-1h-indol-5-yl)-[(3s)-3-propylpyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)[C@@]1(CCC)CCNC1 NVHLQOKZIFFNOX-INIZCTEOSA-N 0.000 claims 1
JAXKGNRNGKCNDY-UHFFFAOYSA-N (7-fluoro-1h-indol-5-yl)-[3-(2-methoxyethyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(CCOC)CCNC1 JAXKGNRNGKCNDY-UHFFFAOYSA-N 0.000 claims 1
BQPPVEGRBUQCRL-UHFFFAOYSA-N (7-fluoro-1h-indol-5-yl)-[3-(2-methylpropyl)piperidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(CC(C)C)CCCNC1 BQPPVEGRBUQCRL-UHFFFAOYSA-N 0.000 claims 1
BLKNUASSHDJVDJ-UHFFFAOYSA-N (7-fluoro-1h-indol-5-yl)-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(CC(C)C)CCNC1 BLKNUASSHDJVDJ-UHFFFAOYSA-N 0.000 claims 1
KIMRUTAJTDBFHO-UHFFFAOYSA-N (7-fluoro-1h-indol-5-yl)-[3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(CCC(C)C)CCNC1 KIMRUTAJTDBFHO-UHFFFAOYSA-N 0.000 claims 1
LKUCVIYUHGVGAZ-UHFFFAOYSA-N (7-fluoro-1h-indol-5-yl)-[3-(oxan-4-ylmethyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=2C=CNC=2C(F)=CC=1C(=O)C1(CC2CCOCC2)CCNC1 LKUCVIYUHGVGAZ-UHFFFAOYSA-N 0.000 claims 1
IUYBDDNJOCDFQW-UHFFFAOYSA-N (7-fluoro-1h-indol-5-yl)-[3-(propan-2-yloxymethyl)piperidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(COC(C)C)CCCNC1 IUYBDDNJOCDFQW-UHFFFAOYSA-N 0.000 claims 1
COCVPLPHVAZDAF-UHFFFAOYSA-N (7-fluoro-1h-indol-5-yl)-[3-(propan-2-yloxymethyl)pyrrolidin-3-yl]methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(COC(C)C)CCNC1 COCVPLPHVAZDAF-UHFFFAOYSA-N 0.000 claims 1
JZHVZAOQFISPAC-UHFFFAOYSA-N (7-fluoro-1h-indol-5-yl)-[3-[2-(1-methylcyclopropyl)ethyl]pyrrolidin-3-yl]methanone Chemical compound C1CNCC1(C(=O)C=1C=C2C=CNC2=C(F)C=1)CCC1(C)CC1 JZHVZAOQFISPAC-UHFFFAOYSA-N 0.000 claims 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
PPAMCHNRHVICEZ-UHFFFAOYSA-N 1,2-benzothiazol-3-yl-(3-butylpyrrolidin-3-yl)methanone Chemical compound N=1SC2=CC=CC=C2C=1C(=O)C1(CCCC)CCNC1 PPAMCHNRHVICEZ-UHFFFAOYSA-N 0.000 claims 1
AQOSFPBDMWRNSO-UHFFFAOYSA-N 1,3-benzothiazol-2-yl-(3-propylpyrrolidin-3-yl)methanone Chemical compound N=1C2=CC=CC=C2SC=1C(=O)C1(CCC)CCNC1 AQOSFPBDMWRNSO-UHFFFAOYSA-N 0.000 claims 1
FVHLAJIUSJQJCT-UHFFFAOYSA-N 1-[2-chloro-5-(3-propylpiperidine-3-carbonyl)phenyl]ethanone Chemical compound C=1C=C(Cl)C(C(C)=O)=CC=1C(=O)C1(CCC)CCCNC1 FVHLAJIUSJQJCT-UHFFFAOYSA-N 0.000 claims 1
FATMZDGAIRCIEY-UHFFFAOYSA-N 1-benzothiophen-2-yl-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)C1(CCC)CCNC1 FATMZDGAIRCIEY-UHFFFAOYSA-N 0.000 claims 1
QGMJTMGGYZGUHD-UHFFFAOYSA-N 1-benzothiophen-2-yl-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)C1(CCC)CCNCC1 QGMJTMGGYZGUHD-UHFFFAOYSA-N 0.000 claims 1
MUCOWQIQUFKAFL-LJQANCHMSA-N 1-benzothiophen-2-yl-[(3r)-3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)[C@]1(CCC(C)(C)C)CCNC1 MUCOWQIQUFKAFL-LJQANCHMSA-N 0.000 claims 1
FATMZDGAIRCIEY-MRXNPFEDSA-N 1-benzothiophen-2-yl-[(3r)-3-propylpyrrolidin-3-yl]methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)[C@]1(CCC)CCNC1 FATMZDGAIRCIEY-MRXNPFEDSA-N 0.000 claims 1
MUCOWQIQUFKAFL-IBGZPJMESA-N 1-benzothiophen-2-yl-[(3s)-3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)[C@@]1(CCC(C)(C)C)CCNC1 MUCOWQIQUFKAFL-IBGZPJMESA-N 0.000 claims 1
ATJBMMVOPZWHLD-UHFFFAOYSA-N 1-benzothiophen-2-yl-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)C1(CC(C)C)CCNC1 ATJBMMVOPZWHLD-UHFFFAOYSA-N 0.000 claims 1
MUCOWQIQUFKAFL-UHFFFAOYSA-N 1-benzothiophen-2-yl-[3-(3,3-dimethylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)C1(CCC(C)(C)C)CCNC1 MUCOWQIQUFKAFL-UHFFFAOYSA-N 0.000 claims 1
JCBUMNQGLPRYGQ-UHFFFAOYSA-N 1-benzothiophen-2-yl-[3-(ethylamino)pyrrolidin-3-yl]methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)C1(NCC)CCNC1 JCBUMNQGLPRYGQ-UHFFFAOYSA-N 0.000 claims 1
JLEVHRDXKOMKHT-UHFFFAOYSA-N 1-benzothiophen-2-yl-[3-(oxan-4-ylmethyl)pyrrolidin-3-yl]methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)C1(CC2CCOCC2)CCNC1 JLEVHRDXKOMKHT-UHFFFAOYSA-N 0.000 claims 1
XAWZAOVMAIDAMF-UHFFFAOYSA-N 1-benzothiophen-2-yl-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)C1(CCC(C)(C)C)CCNCC1 XAWZAOVMAIDAMF-UHFFFAOYSA-N 0.000 claims 1
RPLJVOWONRRKIT-UHFFFAOYSA-N 1-benzothiophen-3-yl-(3-butylpyrrolidin-3-yl)methanone Chemical compound C=1SC2=CC=CC=C2C=1C(=O)C1(CCCC)CCNC1 RPLJVOWONRRKIT-UHFFFAOYSA-N 0.000 claims 1
YNTZYCLDTDOTBO-UHFFFAOYSA-N 1-benzothiophen-3-yl-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1SC2=CC=CC=C2C=1C(=O)C1(CCC)CCNC1 YNTZYCLDTDOTBO-UHFFFAOYSA-N 0.000 claims 1
VZBNKVBBAQKYAD-UHFFFAOYSA-N 1-benzothiophen-3-yl-(4-propylpiperidin-4-yl)methanone Chemical compound C=1SC2=CC=CC=C2C=1C(=O)C1(CCC)CCNCC1 VZBNKVBBAQKYAD-UHFFFAOYSA-N 0.000 claims 1
ZPUKBLDNNGLPQO-UHFFFAOYSA-N 1-benzothiophen-3-yl-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1SC2=CC=CC=C2C=1C(=O)C1(CC(C)C)CCNC1 ZPUKBLDNNGLPQO-UHFFFAOYSA-N 0.000 claims 1
AVUFDYVSVOYGJJ-UHFFFAOYSA-N 1-benzothiophen-3-yl-[3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1SC2=CC=CC=C2C=1C(=O)C1(CCC(C)C)CCNC1 AVUFDYVSVOYGJJ-UHFFFAOYSA-N 0.000 claims 1
DXKFPZZSXXPEHG-UHFFFAOYSA-N 1-benzothiophen-3-yl-[3-(ethoxymethyl)pyrrolidin-3-yl]methanone Chemical compound C=1SC2=CC=CC=C2C=1C(=O)C1(COCC)CCNC1 DXKFPZZSXXPEHG-UHFFFAOYSA-N 0.000 claims 1
HDTFFJQXWCAMCY-UHFFFAOYSA-N 1-benzothiophen-3-yl-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C=1SC2=CC=CC=C2C=1C(=O)C1(CCC(C)(C)C)CCNCC1 HDTFFJQXWCAMCY-UHFFFAOYSA-N 0.000 claims 1
JYORPUXQPMDDTP-UHFFFAOYSA-N 1-benzothiophen-5-yl-(3-benzylpyrrolidin-3-yl)methanone Chemical compound C=1C=C2SC=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 JYORPUXQPMDDTP-UHFFFAOYSA-N 0.000 claims 1
FTQBIVFBXYAAQX-UHFFFAOYSA-N 1h-indazol-5-yl-(2-propylpyrrolidin-2-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CCC)CCCN1 FTQBIVFBXYAAQX-UHFFFAOYSA-N 0.000 claims 1
HSKQAGAIFODDIO-UHFFFAOYSA-N 1h-indazol-5-yl-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CCC)CCNC1 HSKQAGAIFODDIO-UHFFFAOYSA-N 0.000 claims 1
HXVMFBSINMZKRO-MRXNPFEDSA-N 1h-indazol-5-yl-[(2r)-2-(2-methylpropyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)[C@]1(CC(C)C)CCCN1 HXVMFBSINMZKRO-MRXNPFEDSA-N 0.000 claims 1
FTQBIVFBXYAAQX-OAHLLOKOSA-N 1h-indazol-5-yl-[(2r)-2-propylpyrrolidin-2-yl]methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)[C@@]1(CCC)CCCN1 FTQBIVFBXYAAQX-OAHLLOKOSA-N 0.000 claims 1
HXVMFBSINMZKRO-INIZCTEOSA-N 1h-indazol-5-yl-[(2s)-2-(2-methylpropyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)[C@@]1(CC(C)C)CCCN1 HXVMFBSINMZKRO-INIZCTEOSA-N 0.000 claims 1
FTQBIVFBXYAAQX-HNNXBMFYSA-N 1h-indazol-5-yl-[(2s)-2-propylpyrrolidin-2-yl]methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)[C@]1(CCC)CCCN1 FTQBIVFBXYAAQX-HNNXBMFYSA-N 0.000 claims 1
NCEIQWSDAPLEHK-UHFFFAOYSA-N 1h-indazol-5-yl-[2-(1,3-thiazol-4-ylmethyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CC=2N=CSC=2)CCCN1 NCEIQWSDAPLEHK-UHFFFAOYSA-N 0.000 claims 1
HXVMFBSINMZKRO-UHFFFAOYSA-N 1h-indazol-5-yl-[2-(2-methylpropyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CC(C)C)CCCN1 HXVMFBSINMZKRO-UHFFFAOYSA-N 0.000 claims 1
GJZUHTBRZMCTDJ-UHFFFAOYSA-N 1h-indazol-5-yl-[2-(3-methylbutyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CCC(C)C)CCCN1 GJZUHTBRZMCTDJ-UHFFFAOYSA-N 0.000 claims 1
UBRNRVMFPMXRMF-UHFFFAOYSA-N 1h-indazol-5-yl-[2-(propan-2-yloxymethyl)pyrrolidin-2-yl]methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(COC(C)C)CCCN1 UBRNRVMFPMXRMF-UHFFFAOYSA-N 0.000 claims 1
KPACIVQUOBWIMN-UHFFFAOYSA-N 1h-indol-2-yl-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C2=CC=CC=C2NC=1C(=O)C1(CCC)CCNC1 KPACIVQUOBWIMN-UHFFFAOYSA-N 0.000 claims 1
AFRINDQPTXPGEB-UHFFFAOYSA-N 1h-indol-2-yl-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C2=CC=CC=C2NC=1C(=O)C1(CCC)CCNCC1 AFRINDQPTXPGEB-UHFFFAOYSA-N 0.000 claims 1
GKBISTFUEQPKOR-POZUXBRTSA-N 1h-indol-2-yl-[(1r,4r,5r)-4-propyl-8-azabicyclo[3.2.1]octan-4-yl]methanone Chemical compound C1=CC=C2NC(C(=O)[C@@]3(CCC)[C@@]4([H])CC[C@](N4)(CC3)[H])=CC2=C1 GKBISTFUEQPKOR-POZUXBRTSA-N 0.000 claims 1
VTRCIXPMJHQKPU-UHFFFAOYSA-N 1h-indol-2-yl-[4-(2-methylpropyl)piperidin-4-yl]methanone Chemical compound C=1C2=CC=CC=C2NC=1C(=O)C1(CC(C)C)CCNCC1 VTRCIXPMJHQKPU-UHFFFAOYSA-N 0.000 claims 1
RBDKPBIPFDKJBN-UHFFFAOYSA-N 1h-indol-2-yl-[4-(3-methylbutyl)piperidin-4-yl]methanone Chemical compound C=1C2=CC=CC=C2NC=1C(=O)C1(CCC(C)C)CCNCC1 RBDKPBIPFDKJBN-UHFFFAOYSA-N 0.000 claims 1
PASJNAYLJWDQIX-UHFFFAOYSA-N 1h-indol-3-yl-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1NC2=CC=CC=C2C=1C(=O)C1(CCC)CCNC1 PASJNAYLJWDQIX-UHFFFAOYSA-N 0.000 claims 1
UBFDJWJQRZGGNS-UHFFFAOYSA-N 1h-indol-5-yl-(1-methyl-4-propylpiperidin-4-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCC)CCN(C)CC1 UBFDJWJQRZGGNS-UHFFFAOYSA-N 0.000 claims 1
PMWJXJVDUJHXHT-UHFFFAOYSA-N 1h-indol-5-yl-(2-propylpyrrolidin-2-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCC)CCCN1 PMWJXJVDUJHXHT-UHFFFAOYSA-N 0.000 claims 1
QDMBEMALFSLYSJ-UHFFFAOYSA-N 1h-indol-5-yl-(3-phenylpyrrolidin-3-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(C=2C=CC=CC=2)CCNC1 QDMBEMALFSLYSJ-UHFFFAOYSA-N 0.000 claims 1
WVEPJHRFNYVHKC-UHFFFAOYSA-N 1h-indol-5-yl-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCC)CCCNC1 WVEPJHRFNYVHKC-UHFFFAOYSA-N 0.000 claims 1
PAFPHCZHNAQWFM-UHFFFAOYSA-N 1h-indol-5-yl-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCC)CCNC1 PAFPHCZHNAQWFM-UHFFFAOYSA-N 0.000 claims 1
NPLACMCJYPWLAL-UHFFFAOYSA-N 1h-indol-5-yl-(4-phenylpiperidin-4-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(C=2C=CC=CC=2)CCNCC1 NPLACMCJYPWLAL-UHFFFAOYSA-N 0.000 claims 1
KUQHCCYYVOWQKW-UHFFFAOYSA-N 1h-indol-5-yl-(4-propylpiperidin-4-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCC)CCNCC1 KUQHCCYYVOWQKW-UHFFFAOYSA-N 0.000 claims 1
WVEPJHRFNYVHKC-QGZVFWFLSA-N 1h-indol-5-yl-[(3r)-3-propylpiperidin-3-yl]methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)[C@]1(CCC)CCCNC1 WVEPJHRFNYVHKC-QGZVFWFLSA-N 0.000 claims 1
PAFPHCZHNAQWFM-MRXNPFEDSA-N 1h-indol-5-yl-[(3r)-3-propylpyrrolidin-3-yl]methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)[C@]1(CCC)CCNC1 PAFPHCZHNAQWFM-MRXNPFEDSA-N 0.000 claims 1
WVEPJHRFNYVHKC-KRWDZBQOSA-N 1h-indol-5-yl-[(3s)-3-propylpiperidin-3-yl]methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)[C@@]1(CCC)CCCNC1 WVEPJHRFNYVHKC-KRWDZBQOSA-N 0.000 claims 1
PAFPHCZHNAQWFM-INIZCTEOSA-N 1h-indol-5-yl-[(3s)-3-propylpyrrolidin-3-yl]methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)[C@@]1(CCC)CCNC1 PAFPHCZHNAQWFM-INIZCTEOSA-N 0.000 claims 1
KQRUSJVSSJUUGL-UHFFFAOYSA-N 1h-indol-5-yl-[3-(1,3-thiazol-4-ylmethyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CC=2N=CSC=2)CCNC1 KQRUSJVSSJUUGL-UHFFFAOYSA-N 0.000 claims 1
HHCWELKPROEGBD-UHFFFAOYSA-N 1h-indol-5-yl-[3-(2-methylpropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CC(C)C)CCNC1 HHCWELKPROEGBD-UHFFFAOYSA-N 0.000 claims 1
FCWQIBQYGRELGF-UHFFFAOYSA-N 1h-indol-5-yl-[3-(3,3,3-trifluoropropyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCC(F)(F)F)CCNC1 FCWQIBQYGRELGF-UHFFFAOYSA-N 0.000 claims 1
OXTQLJSTWXJZFS-UHFFFAOYSA-N 1h-indol-5-yl-[3-(3-methylbutyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCC(C)C)CCNC1 OXTQLJSTWXJZFS-UHFFFAOYSA-N 0.000 claims 1
ZIVCVUMBNPWNTM-UHFFFAOYSA-N 1h-indol-5-yl-[3-(methoxymethyl)pyrrolidin-3-yl]methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(COC)CCNC1 ZIVCVUMBNPWNTM-UHFFFAOYSA-N 0.000 claims 1
CFFNMNCKKGSBAC-UHFFFAOYSA-N 1h-indol-5-yl-[3-[(3-methoxyphenyl)methyl]pyrrolidin-3-yl]methanone Chemical compound COC1=CC=CC(CC2(CNCC2)C(=O)C=2C=C3C=CNC3=CC=2)=C1 CFFNMNCKKGSBAC-UHFFFAOYSA-N 0.000 claims 1
LGTBDDRIZSWBDK-UHFFFAOYSA-N 1h-indol-5-yl-[3-[(4-methoxyphenyl)methyl]piperidin-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1CC1(C(=O)C=2C=C3C=CNC3=CC=2)CNCCC1 LGTBDDRIZSWBDK-UHFFFAOYSA-N 0.000 claims 1
LNDJBGBJACHZQS-UHFFFAOYSA-N 1h-indol-5-yl-[3-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1CC1(C(=O)C=2C=C3C=CNC3=CC=2)CNCC1 LNDJBGBJACHZQS-UHFFFAOYSA-N 0.000 claims 1
YCCKQBKDJWHFHZ-UHFFFAOYSA-N 1h-indol-5-yl-[4-[(3-methoxyphenyl)methyl]piperidin-4-yl]methanone Chemical compound COC1=CC=CC(CC2(CCNCC2)C(=O)C=2C=C3C=CNC3=CC=2)=C1 YCCKQBKDJWHFHZ-UHFFFAOYSA-N 0.000 claims 1
WWTVYYLJVACEPI-UHFFFAOYSA-N 1h-indol-5-yl-[4-[(4-methoxyphenyl)methyl]piperidin-4-yl]methanone Chemical compound C1=CC(OC)=CC=C1CC1(C(=O)C=2C=C3C=CNC3=CC=2)CCNCC1 WWTVYYLJVACEPI-UHFFFAOYSA-N 0.000 claims 1
HJIBDIRLSUZJTJ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-5-yl-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C2CCCC2=CC=1C(=O)C1(CCC)CCCNC1 HJIBDIRLSUZJTJ-UHFFFAOYSA-N 0.000 claims 1
DTADZLJUFZBJAH-UHFFFAOYSA-N 2-chloro-5-(3-propylpiperidine-3-carbonyl)benzonitrile Chemical compound C=1C=C(Cl)C(C#N)=CC=1C(=O)C1(CCC)CCCNC1 DTADZLJUFZBJAH-UHFFFAOYSA-N 0.000 claims 1
FJZBBDQVQPAHNA-UHFFFAOYSA-N 2-chloro-n,n-dimethyl-5-(3-propylpiperidine-3-carbonyl)benzamide Chemical compound C=1C=C(Cl)C(C(=O)N(C)C)=CC=1C(=O)C1(CCC)CCCNC1 FJZBBDQVQPAHNA-UHFFFAOYSA-N 0.000 claims 1
KKLBILMKBWHAMC-UHFFFAOYSA-N 2-chloro-n-methyl-5-(3-propylpiperidine-3-carbonyl)benzamide Chemical compound C=1C=C(Cl)C(C(=O)NC)=CC=1C(=O)C1(CCC)CCCNC1 KKLBILMKBWHAMC-UHFFFAOYSA-N 0.000 claims 1
IXBBOTZBUNWDMZ-UHFFFAOYSA-N 3-[[3-(1h-indole-5-carbonyl)pyrrolidin-3-yl]methyl]benzonitrile Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CC=2C=C(C=CC=2)C#N)CCNC1 IXBBOTZBUNWDMZ-UHFFFAOYSA-N 0.000 claims 1
125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
MBEQJNUOQFXAIF-UHFFFAOYSA-N 4-(3-propylpiperidine-3-carbonyl)benzene-1,2-dicarbonitrile Chemical compound C=1C=C(C#N)C(C#N)=CC=1C(=O)C1(CCC)CCCNC1 MBEQJNUOQFXAIF-UHFFFAOYSA-N 0.000 claims 1
NLRCHLOJBVBRNV-UHFFFAOYSA-N 4-(3-propylpiperidine-3-carbonyl)benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(=O)C1(CCC)CCCNC1 NLRCHLOJBVBRNV-UHFFFAOYSA-N 0.000 claims 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
VUYUNLZAYBCULL-UHFFFAOYSA-N 5-(3,4-dichlorobenzoyl)-5-propylpyrrolidin-3-one Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C1(CCC)CC(=O)CN1 VUYUNLZAYBCULL-UHFFFAOYSA-N 0.000 claims 1
UBFXZGVYPOIDGF-UHFFFAOYSA-N 5-(3-benzylpyrrolidine-3-carbonyl)-1,3-dihydroindol-2-one Chemical compound C=1C=C2NC(=O)CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 UBFXZGVYPOIDGF-UHFFFAOYSA-N 0.000 claims 1
GFXBWCKXIIVGDE-UHFFFAOYSA-N 5-(3-benzylpyrrolidine-3-carbonyl)-1h-indole-3-carbonitrile Chemical compound C=1C=C2NC=C(C#N)C2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCNC1 GFXBWCKXIIVGDE-UHFFFAOYSA-N 0.000 claims 1
KKIOMFVVMRZONL-UHFFFAOYSA-N 6-(3-propylpyrrolidine-3-carbonyl)-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1C(=O)C1(CCC)CCNC1 KKIOMFVVMRZONL-UHFFFAOYSA-N 0.000 claims 1
208000019901 Anxiety disease Diseases 0.000 claims 1
YDQSMHWMTMIAGX-UHFFFAOYSA-N C(CCC(=O)O)(=O)O.C(CC)C1(CNCCC1)C(=O)C1=CC=C(C=C1)C1=NNC=C1 Chemical compound C(CCC(=O)O)(=O)O.C(CC)C1(CNCCC1)C(=O)C1=CC=C(C=C1)C1=NNC=C1 YDQSMHWMTMIAGX-UHFFFAOYSA-N 0.000 claims 1
SLNOOUVFQRLQAI-GOSISDBHSA-N [(2R)-2-benzylpyrrolidin-2-yl]-phenylmethanone Chemical compound C(C1=CC=CC=C1)[C@@]1(NCCC1)C(=O)C1=CC=CC=C1 SLNOOUVFQRLQAI-GOSISDBHSA-N 0.000 claims 1
MJCKYDPFUPMINT-LJQANCHMSA-N [(3r)-3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(7-fluoro-1h-indol-5-yl)methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)[C@]1(CCC(C)(C)C)CCNC1 MJCKYDPFUPMINT-LJQANCHMSA-N 0.000 claims 1
MJCKYDPFUPMINT-IBGZPJMESA-N [(3s)-3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(7-fluoro-1h-indol-5-yl)methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)[C@@]1(CCC(C)(C)C)CCNC1 MJCKYDPFUPMINT-IBGZPJMESA-N 0.000 claims 1
ZYHPOMSWEWJZRL-UHFFFAOYSA-N [1-(benzenesulfonyl)indol-2-yl]-[4-(2-methylpropyl)piperidin-4-yl]methanone Chemical compound C=1C2=CC=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(=O)C1(CC(C)C)CCNCC1 ZYHPOMSWEWJZRL-UHFFFAOYSA-N 0.000 claims 1
RCCJEGPNBYSMDE-UHFFFAOYSA-N [1-(benzenesulfonyl)indol-2-yl]-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C=1C2=CC=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(=O)C1(CCC(C)(C)C)CCNCC1 RCCJEGPNBYSMDE-UHFFFAOYSA-N 0.000 claims 1
NKXOGAAVTXYCBU-UHFFFAOYSA-N [2-(2-cyclohexylethyl)pyrrolidin-2-yl]-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CCC2CCCCC2)CCCN1 NKXOGAAVTXYCBU-UHFFFAOYSA-N 0.000 claims 1
WMONHIUXMOXBDS-UHFFFAOYSA-N [2-(3,3-dimethylbutyl)pyrrolidin-2-yl]-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CCC(C)(C)C)CCCN1 WMONHIUXMOXBDS-UHFFFAOYSA-N 0.000 claims 1
ACZLMZFJNDNYHM-UHFFFAOYSA-N [2-(cyclobutylmethyl)pyrrolidin-2-yl]-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CC2CCC2)CCCN1 ACZLMZFJNDNYHM-UHFFFAOYSA-N 0.000 claims 1
QCCVMJVUEZILMO-UHFFFAOYSA-N [2-(cyclohexylmethyl)pyrrolidin-2-yl]-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CC2CCCCC2)CCCN1 QCCVMJVUEZILMO-UHFFFAOYSA-N 0.000 claims 1
KKYFYRTWOVEUTE-UHFFFAOYSA-N [2-(cyclopentylmethyl)pyrrolidin-2-yl]-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CC2CCCC2)CCCN1 KKYFYRTWOVEUTE-UHFFFAOYSA-N 0.000 claims 1
XMRQWYRMGDXIKE-UHFFFAOYSA-N [2-(cyclopropylmethyl)pyrrolidin-2-yl]-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CC2CC2)CCCN1 XMRQWYRMGDXIKE-UHFFFAOYSA-N 0.000 claims 1
XNHHQYVSNRQOGN-UHFFFAOYSA-N [2-(ethoxymethyl)pyrrolidin-2-yl]-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(COCC)CCCN1 XNHHQYVSNRQOGN-UHFFFAOYSA-N 0.000 claims 1
VUFHWZXUBWNORX-UHFFFAOYSA-N [3-(2-cyclohexylethyl)pyrrolidin-3-yl]-(3,4-dichlorophenyl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C1(CCC2CCCCC2)CNCC1 VUFHWZXUBWNORX-UHFFFAOYSA-N 0.000 claims 1
HPAPZWUDKFMZMC-UHFFFAOYSA-N [3-(2-cyclopropylethyl)pyrrolidin-3-yl]-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCC2CC2)CCNC1 HPAPZWUDKFMZMC-UHFFFAOYSA-N 0.000 claims 1
JXIHZLYRWFFHPQ-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(1h-indazol-5-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C(=O)C1(CCC(C)(C)C)CCNC1 JXIHZLYRWFFHPQ-UHFFFAOYSA-N 0.000 claims 1
GBLULAKVGYVWTB-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(1h-indol-2-yl)methanone Chemical compound C=1C2=CC=CC=C2NC=1C(=O)C1(CCC(C)(C)C)CCNC1 GBLULAKVGYVWTB-UHFFFAOYSA-N 0.000 claims 1
UBAFWEAUURTRJS-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CCC(C)(C)C)CCNC1 UBAFWEAUURTRJS-UHFFFAOYSA-N 0.000 claims 1
VPDGWIMMHFLNIR-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(1h-pyrrolo[3,2-b]pyridin-2-yl)methanone Chemical compound C=1C2=NC=CC=C2NC=1C(=O)C1(CCC(C)(C)C)CCNC1 VPDGWIMMHFLNIR-UHFFFAOYSA-N 0.000 claims 1
BIVOSYFAZKXJPQ-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(1h-pyrrolo[3,2-b]pyridin-5-yl)methanone Chemical compound C=1C=C2NC=CC2=NC=1C(=O)C1(CCC(C)(C)C)CCNC1 BIVOSYFAZKXJPQ-UHFFFAOYSA-N 0.000 claims 1
VTIWZRPTCWJTEC-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(4-fluoro-1-benzothiophen-2-yl)methanone Chemical compound C=1C2=C(F)C=CC=C2SC=1C(=O)C1(CCC(C)(C)C)CCNC1 VTIWZRPTCWJTEC-UHFFFAOYSA-N 0.000 claims 1
RWFQHHGIGTULSH-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(4-methylquinolin-2-yl)methanone Chemical compound N=1C2=CC=CC=C2C(C)=CC=1C(=O)C1(CCC(C)(C)C)CCNC1 RWFQHHGIGTULSH-UHFFFAOYSA-N 0.000 claims 1
OMDABHHLPRURBF-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(5-fluoro-1-benzothiophen-2-yl)methanone Chemical compound C=1C2=CC(F)=CC=C2SC=1C(=O)C1(CCC(C)(C)C)CCNC1 OMDABHHLPRURBF-UHFFFAOYSA-N 0.000 claims 1
YOWUBZTUZXLCTP-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(5-fluoro-1-benzothiophen-3-yl)methanone Chemical compound C=1SC2=CC=C(F)C=C2C=1C(=O)C1(CCC(C)(C)C)CCNC1 YOWUBZTUZXLCTP-UHFFFAOYSA-N 0.000 claims 1
NSPMSZZVYJVWRR-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(5-fluoro-1h-indol-2-yl)methanone Chemical compound C=1C2=CC(F)=CC=C2NC=1C(=O)C1(CCC(C)(C)C)CCNC1 NSPMSZZVYJVWRR-UHFFFAOYSA-N 0.000 claims 1
UZBJVBBURLGFEJ-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(7-fluoro-1-benzothiophen-2-yl)methanone Chemical compound C=1C2=CC=CC(F)=C2SC=1C(=O)C1(CCC(C)(C)C)CCNC1 UZBJVBBURLGFEJ-UHFFFAOYSA-N 0.000 claims 1
PYVJGAJSQAJKLP-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(7-fluoro-1-benzothiophen-3-yl)methanone Chemical compound C=1SC2=C(F)C=CC=C2C=1C(=O)C1(CCC(C)(C)C)CCNC1 PYVJGAJSQAJKLP-UHFFFAOYSA-N 0.000 claims 1
MJCKYDPFUPMINT-UHFFFAOYSA-N [3-(3,3-dimethylbutyl)pyrrolidin-3-yl]-(7-fluoro-1h-indol-5-yl)methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(CCC(C)(C)C)CCNC1 MJCKYDPFUPMINT-UHFFFAOYSA-N 0.000 claims 1
UOBMIAXVLCRTIG-UHFFFAOYSA-N [3-(4-fluorophenoxy)phenyl]-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=CC(OC=2C=CC(F)=CC=2)=CC=1C(=O)C1(CCC)CCNC1 UOBMIAXVLCRTIG-UHFFFAOYSA-N 0.000 claims 1
OOWSDISYPCDYPH-UHFFFAOYSA-N [3-(cyclopentylmethyl)pyrrolidin-3-yl]-(3,4-dichlorophenyl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C1(CC2CCCC2)CNCC1 OOWSDISYPCDYPH-UHFFFAOYSA-N 0.000 claims 1
XRZUNJSXLSXKNH-UHFFFAOYSA-N [3-(cyclopropylmethyl)piperidin-3-yl]-(7-fluoro-1h-indol-5-yl)methanone Chemical compound C=1C=2C=CNC=2C(F)=CC=1C(=O)C1(CC2CC2)CCCNC1 XRZUNJSXLSXKNH-UHFFFAOYSA-N 0.000 claims 1
XERSFDRKLLDZRN-UHFFFAOYSA-N [3-(cyclopropylmethyl)pyrrolidin-3-yl]-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CC2CC2)CCNC1 XERSFDRKLLDZRN-UHFFFAOYSA-N 0.000 claims 1
DPOAULJGTVJJKN-UHFFFAOYSA-N [3-(cyclopropylmethyl)pyrrolidin-3-yl]-(3,4-dichlorophenyl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C1(CC2CC2)CNCC1 DPOAULJGTVJJKN-UHFFFAOYSA-N 0.000 claims 1
DUKHQZJSWXYIHH-UHFFFAOYSA-N [3-(cyclopropylmethyl)pyrrolidin-3-yl]-(7-fluoro-1h-indol-5-yl)methanone Chemical compound C=1C=2C=CNC=2C(F)=CC=1C(=O)C1(CC2CC2)CCNC1 DUKHQZJSWXYIHH-UHFFFAOYSA-N 0.000 claims 1
PTPJPGGLNMAPEZ-UHFFFAOYSA-N [3-(ethoxymethyl)piperidin-3-yl]-(7-fluoro-1h-indol-5-yl)methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(COCC)CCCNC1 PTPJPGGLNMAPEZ-UHFFFAOYSA-N 0.000 claims 1
JOKBDWHAIJTJDQ-UHFFFAOYSA-N [3-(ethoxymethyl)pyrrolidin-3-yl]-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(COCC)CCNC1 JOKBDWHAIJTJDQ-UHFFFAOYSA-N 0.000 claims 1
HTWUTDCRXVUCMF-UHFFFAOYSA-N [3-(ethoxymethyl)pyrrolidin-3-yl]-(5-fluoro-1-benzothiophen-2-yl)methanone Chemical compound C=1C2=CC(F)=CC=C2SC=1C(=O)C1(COCC)CCNC1 HTWUTDCRXVUCMF-UHFFFAOYSA-N 0.000 claims 1
PKEWUQPHEKJOIK-UHFFFAOYSA-N [3-(ethoxymethyl)pyrrolidin-3-yl]-(7-fluoro-1h-indol-5-yl)methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(COCC)CCNC1 PKEWUQPHEKJOIK-UHFFFAOYSA-N 0.000 claims 1
YLMCLMDTVSEMCX-UHFFFAOYSA-N [3-(ethylsulfonylmethyl)pyrrolidin-3-yl]-(7-fluoro-1h-indol-5-yl)methanone Chemical compound C=1C(F)=C2NC=CC2=CC=1C(=O)C1(CS(=O)(=O)CC)CCNC1 YLMCLMDTVSEMCX-UHFFFAOYSA-N 0.000 claims 1
CYDBQDVVSAFIMK-UHFFFAOYSA-N [3-[(2-fluorophenyl)methyl]pyrrolidin-3-yl]-(1h-indol-5-yl)methanone Chemical compound FC1=CC=CC=C1CC1(C(=O)C=2C=C3C=CNC3=CC=2)CNCC1 CYDBQDVVSAFIMK-UHFFFAOYSA-N 0.000 claims 1
RNOZFQHEKGDWBK-UHFFFAOYSA-N [3-[(3,4-dichlorophenyl)methyl]pyrrolidin-3-yl]-(1h-indol-5-yl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1CC1(C(=O)C=2C=C3C=CNC3=CC=2)CNCC1 RNOZFQHEKGDWBK-UHFFFAOYSA-N 0.000 claims 1
OJDQPWDNQIQEKC-UHFFFAOYSA-N [3-[(3-fluorophenyl)methyl]piperidin-3-yl]-(1h-indol-5-yl)methanone Chemical compound FC1=CC=CC(CC2(CNCCC2)C(=O)C=2C=C3C=CNC3=CC=2)=C1 OJDQPWDNQIQEKC-UHFFFAOYSA-N 0.000 claims 1
UYJQFFOSKCKBLC-UHFFFAOYSA-N [3-[(3-fluorophenyl)methyl]pyrrolidin-3-yl]-(1h-indol-5-yl)methanone Chemical compound FC1=CC=CC(CC2(CNCC2)C(=O)C=2C=C3C=CNC3=CC=2)=C1 UYJQFFOSKCKBLC-UHFFFAOYSA-N 0.000 claims 1
JACJIXMAUKDVJE-UHFFFAOYSA-N [3-[(4-fluorophenyl)methyl]pyrrolidin-3-yl]-(1h-indol-5-yl)methanone Chemical compound C1=CC(F)=CC=C1CC1(C(=O)C=2C=C3C=CNC3=CC=2)CNCC1 JACJIXMAUKDVJE-UHFFFAOYSA-N 0.000 claims 1
MGCBHVZKRAZSAY-UHFFFAOYSA-N [3-chloro-4-(dimethylamino)phenyl]-[4-(3,3-dimethylbutyl)piperidin-4-yl]methanone Chemical compound C1=C(Cl)C(N(C)C)=CC=C1C(=O)C1(CCC(C)(C)C)CCNCC1 MGCBHVZKRAZSAY-UHFFFAOYSA-N 0.000 claims 1
YDIHKFUVPVPCGQ-UHFFFAOYSA-N [4-(2-fluorophenyl)-1-methylpiperidin-4-yl]-phenylmethanone Chemical compound C1CN(C)CCC1(C=1C(=CC=CC=1)F)C(=O)C1=CC=CC=C1 YDIHKFUVPVPCGQ-UHFFFAOYSA-N 0.000 claims 1
MTURLPAXYGPGNY-UHFFFAOYSA-N [4-(3,3-dimethylbutyl)piperidin-4-yl]-(1-methylindol-2-yl)methanone Chemical compound C=1C2=CC=CC=C2N(C)C=1C(=O)C1(CCC(C)(C)C)CCNCC1 MTURLPAXYGPGNY-UHFFFAOYSA-N 0.000 claims 1
VLAXXPWTVQQZOD-UHFFFAOYSA-N [4-(3,3-dimethylbutyl)piperidin-4-yl]-(1h-indol-2-yl)methanone Chemical compound C=1C2=CC=CC=C2NC=1C(=O)C1(CCC(C)(C)C)CCNCC1 VLAXXPWTVQQZOD-UHFFFAOYSA-N 0.000 claims 1
CADILMZWZQVAHB-UHFFFAOYSA-N [4-(3,3-dimethylbutyl)piperidin-4-yl]-(4-methylquinolin-2-yl)methanone Chemical compound N=1C2=CC=CC=C2C(C)=CC=1C(=O)C1(CCC(C)(C)C)CCNCC1 CADILMZWZQVAHB-UHFFFAOYSA-N 0.000 claims 1
BXPVDWXHLSLEIJ-UHFFFAOYSA-N [4-(3-methylbutyl)piperidin-4-yl]-(1-methylindol-2-yl)methanone Chemical compound C=1C2=CC=CC=C2N(C)C=1C(=O)C1(CCC(C)C)CCNCC1 BXPVDWXHLSLEIJ-UHFFFAOYSA-N 0.000 claims 1
AYALDIBQODLYEL-UHFFFAOYSA-N [4-(cyclopropylmethyl)piperidin-4-yl]-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)C1(CC2CC2)CCNCC1 AYALDIBQODLYEL-UHFFFAOYSA-N 0.000 claims 1
AGKIVZSVOWEBBU-UHFFFAOYSA-N [4-[(2-fluorophenyl)methyl]piperidin-4-yl]-(1h-indol-5-yl)methanone Chemical compound FC1=CC=CC=C1CC1(C(=O)C=2C=C3C=CNC3=CC=2)CCNCC1 AGKIVZSVOWEBBU-UHFFFAOYSA-N 0.000 claims 1
NJOAEERKPXTLQA-UHFFFAOYSA-N [4-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]-(1h-indol-5-yl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1CC1(C(=O)C=2C=C3C=CNC3=CC=2)CCNCC1 NJOAEERKPXTLQA-UHFFFAOYSA-N 0.000 claims 1
ZKJZBBPYVAVKIN-UHFFFAOYSA-N [4-[(3,4-difluorophenyl)methyl]piperidin-4-yl]-(1h-indol-5-yl)methanone Chemical compound C1=C(F)C(F)=CC=C1CC1(C(=O)C=2C=C3C=CNC3=CC=2)CCNCC1 ZKJZBBPYVAVKIN-UHFFFAOYSA-N 0.000 claims 1
TVGLIGMMLHJRBU-UHFFFAOYSA-N [4-[(4-fluorophenyl)methyl]piperidin-4-yl]-(1h-indol-5-yl)methanone Chemical compound C1=CC(F)=CC=C1CC1(C(=O)C=2C=C3C=CNC3=CC=2)CCNCC1 TVGLIGMMLHJRBU-UHFFFAOYSA-N 0.000 claims 1
XKYVCIZIFSCPNZ-UHFFFAOYSA-N [4-chloro-3-(methoxymethyl)phenyl]-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(COC)=CC=1C(=O)C1(CCC)CCCNC1 XKYVCIZIFSCPNZ-UHFFFAOYSA-N 0.000 claims 1
DMBWSQCLSKOBRK-UHFFFAOYSA-N [4-chloro-3-(trifluoromethyl)phenyl]-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C(Cl)C(C(F)(F)F)=CC=1C(=O)C1(CCC)CCNC1 DMBWSQCLSKOBRK-UHFFFAOYSA-N 0.000 claims 1
NFFXRNVVJFRMKB-UHFFFAOYSA-N [4-chloro-5-(4-fluorophenyl)thiophen-2-yl]-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C(Cl)=C(C=2C=CC(F)=CC=2)SC=1C(=O)C1(CCC)CCNC1 NFFXRNVVJFRMKB-UHFFFAOYSA-N 0.000 claims 1
230000036506 anxiety Effects 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
MZHVSTHRLSNXHT-UHFFFAOYSA-N n-[2-chloro-4-(3-propylpyrrolidine-3-carbonyl)phenyl]acetamide Chemical compound C=1C=C(NC(C)=O)C(Cl)=CC=1C(=O)C1(CCC)CCNC1 MZHVSTHRLSNXHT-UHFFFAOYSA-N 0.000 claims 1
VBEMGXWXVKPWOG-UHFFFAOYSA-N naphthalen-1-yl-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)C1(CCC)CCCNC1 VBEMGXWXVKPWOG-UHFFFAOYSA-N 0.000 claims 1
WQOQFJFFBGFADY-UHFFFAOYSA-N naphthalen-2-yl-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)C1(CCC)CCNC1 WQOQFJFFBGFADY-UHFFFAOYSA-N 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
JFLDPEHZOPUJKB-UHFFFAOYSA-N phenyl-(2-phenylaziridin-2-yl)methanone Chemical compound C(C1=CC=CC=C1)(=O)C1(NC1)C1=CC=CC=C1 JFLDPEHZOPUJKB-UHFFFAOYSA-N 0.000 claims 1
NDFWXXSBXFCVIJ-UHFFFAOYSA-N phenyl-(3-propylpiperidin-3-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1(CCC)CCCNC1 NDFWXXSBXFCVIJ-UHFFFAOYSA-N 0.000 claims 1
LYDYEKDUTCXXCD-UHFFFAOYSA-N phenyl-(3-propylpyrrolidin-3-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1(CCC)CCNC1 LYDYEKDUTCXXCD-UHFFFAOYSA-N 0.000 claims 1
KQXNRQAHJUXJOY-UHFFFAOYSA-N phenyl-(4-phenylpiperidin-4-yl)methanone Chemical compound C1CNCCC1(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 KQXNRQAHJUXJOY-UHFFFAOYSA-N 0.000 claims 1
125000000168 pyrrolyl group Chemical group 0.000 claims 1

JP2009541988A 2006-12-19 2007-12-11 ヘテロアリールピロリジニル及びピペリジニルケトン誘導体 Active JP5394252B2 (ja)