JP5394252B2 - 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 - Google Patents
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 Download PDFInfo
- Publication number
- JP5394252B2 JP5394252B2 JP2009541988A JP2009541988A JP5394252B2 JP 5394252 B2 JP5394252 B2 JP 5394252B2 JP 2009541988 A JP2009541988 A JP 2009541988A JP 2009541988 A JP2009541988 A JP 2009541988A JP 5394252 B2 JP5394252 B2 JP 5394252B2
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- JP
- Japan
- Prior art keywords
- phenyl
- methanone
- pyrrolidin
- propyl
- dichloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- SNOJOKOVTYPHMC-UHFFFAOYSA-N di(piperidin-1-yl)methanone Chemical class C1CCCCN1C(=O)N1CCCCC1 SNOJOKOVTYPHMC-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 224
- 150000001875 compounds Chemical class 0.000 claims description 155
- 125000003545 alkoxy group Chemical group 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 230000036506 anxiety Effects 0.000 claims description 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 3
- 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 description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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- GQXDSRFXFNBSKC-UHFFFAOYSA-N tert-butyl 2-propylpyrrolidine-1-carboxylate Chemical compound CCCC1CCCN1C(=O)OC(C)(C)C GQXDSRFXFNBSKC-UHFFFAOYSA-N 0.000 description 1
- DYJGUUKOAUAHFN-UHFFFAOYSA-N tert-butyl 3-(3,3-dimethylbutyl)-3-[(5-fluoro-1-benzothiophen-3-yl)-hydroxymethyl]pyrrolidine-1-carboxylate Chemical compound C=1SC2=CC=C(F)C=C2C=1C(O)C1(CCC(C)(C)C)CCN(C(=O)OC(C)(C)C)C1 DYJGUUKOAUAHFN-UHFFFAOYSA-N 0.000 description 1
- LREDKVKVSWXYEO-UHFFFAOYSA-N tert-butyl 3-(3,3-dimethylbutyl)-3-formylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)CCC1(C=O)CCN(C(=O)OC(C)(C)C)C1 LREDKVKVSWXYEO-UHFFFAOYSA-N 0.000 description 1
- VVTAVOCTUQTUHN-UHFFFAOYSA-N tert-butyl 3-(3,4-dichlorobenzoyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1C(=O)C1=CC=C(Cl)C(Cl)=C1 VVTAVOCTUQTUHN-UHFFFAOYSA-N 0.000 description 1
- QNUOCVPSXWKAHB-UHFFFAOYSA-N tert-butyl 3-(4,5-dichlorothiophene-2-carbonyl)-3-propylpyrrolidine-1-carboxylate Chemical compound C=1C(Cl)=C(Cl)SC=1C(=O)C1(CCC)CCN(C(=O)OC(C)(C)C)C1 QNUOCVPSXWKAHB-UHFFFAOYSA-N 0.000 description 1
- TUQKDGXDEZIHOE-UHFFFAOYSA-N tert-butyl 3-[methoxy(methyl)carbamoyl]azepine-1-carboxylate Chemical compound CON(C)C(=O)C1=CN(C(=O)OC(C)(C)C)C=CC=C1 TUQKDGXDEZIHOE-UHFFFAOYSA-N 0.000 description 1
- NQGXVXHYGRAABB-UHFFFAOYSA-N tert-butyl 3-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate Chemical compound CON(C)C(=O)C1CCCN(C(=O)OC(C)(C)C)C1 NQGXVXHYGRAABB-UHFFFAOYSA-N 0.000 description 1
- VIFFMJWKRWQLIO-UHFFFAOYSA-N tert-butyl 3-benzyl-3-(3,4-dichlorobenzoyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C(=O)C=1C=C(Cl)C(Cl)=CC=1)CC1=CC=CC=C1 VIFFMJWKRWQLIO-UHFFFAOYSA-N 0.000 description 1
- PGJSGFSRMUBINE-UHFFFAOYSA-N tert-butyl 3-benzyl-3-(3-cyano-1h-indole-5-carbonyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C(=O)C=1C=C2C(C#N)=CNC2=CC=1)CC1=CC=CC=C1 PGJSGFSRMUBINE-UHFFFAOYSA-N 0.000 description 1
- AVKNDBTUXZCLNM-UHFFFAOYSA-N tert-butyl 3-benzyl-3-[1-tri(propan-2-yl)silylindole-5-carbonyl]pyrrolidine-1-carboxylate Chemical compound C=1C=C2N([Si](C(C)C)(C(C)C)C(C)C)C=CC2=CC=1C(=O)C1(CC=2C=CC=CC=2)CCN(C(=O)OC(C)(C)C)C1 AVKNDBTUXZCLNM-UHFFFAOYSA-N 0.000 description 1
- CFLSSKGYTDGVHE-UHFFFAOYSA-N tert-butyl 3-formyl-3-(oxan-4-ylmethyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C=O)CC1CCOCC1 CFLSSKGYTDGVHE-UHFFFAOYSA-N 0.000 description 1
- MENILFUADYEXNU-UHFFFAOYSA-N tert-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1C(=O)CC2CCC1N2C(=O)OC(C)(C)C MENILFUADYEXNU-UHFFFAOYSA-N 0.000 description 1
- QBHNPPQDCJSKOJ-UHFFFAOYSA-N tert-butyl 4-(1h-indole-5-carbonyl)-4-phenylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C=1C=CC=CC=1)C(=O)C1=CC=C(NC=C2)C2=C1 QBHNPPQDCJSKOJ-UHFFFAOYSA-N 0.000 description 1
- GVLQDRIRKOSYEG-UHFFFAOYSA-N tert-butyl 4-(5-fluoro-1h-indole-2-carbonyl)-4-propylpiperidine-1-carboxylate Chemical compound C=1C2=CC(F)=CC=C2NC=1C(=O)C1(CCC)CCN(C(=O)OC(C)(C)C)CC1 GVLQDRIRKOSYEG-UHFFFAOYSA-N 0.000 description 1
- FUAVJSBNGZUHQN-UHFFFAOYSA-N tert-butyl 4-(hydroxymethyl)-4-propyl-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound CCCC1(CO)CCC2CCC1N2C(=O)OC(C)(C)C FUAVJSBNGZUHQN-UHFFFAOYSA-N 0.000 description 1
- RKLBYZHXXUDLPI-UHFFFAOYSA-N tert-butyl 4-(methoxymethylcarbamoyl)piperidine-1-carboxylate Chemical compound COCNC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 RKLBYZHXXUDLPI-UHFFFAOYSA-N 0.000 description 1
- WSMMFDBWZUXWNM-UHFFFAOYSA-N tert-butyl 4-[(3,4-dichlorophenyl)-hydroxymethyl]-4-propyl-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1CC(N2C(=O)OC(C)(C)C)CCC2C1(CCC)C(O)C1=CC=C(Cl)C(Cl)=C1 WSMMFDBWZUXWNM-UHFFFAOYSA-N 0.000 description 1
- FNNDNBVULYWFBD-UHFFFAOYSA-N tert-butyl 4-[1-(benzenesulfonyl)-5-fluoroindole-2-carbonyl]-4-propylpiperidine-1-carboxylate Chemical compound C=1C2=CC(F)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(=O)C1(CCC)CCN(C(=O)OC(C)(C)C)CC1 FNNDNBVULYWFBD-UHFFFAOYSA-N 0.000 description 1
- KTOHDQVSDBRNCL-UHFFFAOYSA-N tert-butyl 4-[[1-(benzenesulfonyl)-5-fluoroindol-2-yl]-hydroxymethyl]-4-propylpiperidine-1-carboxylate Chemical compound C=1C2=CC(F)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(O)C1(CCC)CCN(C(=O)OC(C)(C)C)CC1 KTOHDQVSDBRNCL-UHFFFAOYSA-N 0.000 description 1
- YNEHGSUPEHZJIP-UHFFFAOYSA-N tert-butyl 4-propyl-4-(quinoline-2-carbonyl)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=NC=1C(=O)C1(CCC)CCN(C(=O)OC(C)(C)C)CC1 YNEHGSUPEHZJIP-UHFFFAOYSA-N 0.000 description 1
- ZCSIWLWIAHYNOI-UHFFFAOYSA-N tert-butyl 4-propyl-4-(quinoline-2-carbonyl)piperidine-1-carboxylate (4-propylpiperidin-4-yl)-quinolin-2-ylmethanone Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)(C(=O)C1=NC2=CC=CC=C2C=C1)CCC.C(CC)C1(CCNCC1)C(=O)C1=NC2=CC=CC=C2C=C1 ZCSIWLWIAHYNOI-UHFFFAOYSA-N 0.000 description 1
- LUNFBLBGFLEXHS-UHFFFAOYSA-N tert-butyl 5-[1-[(2-methylpropan-2-yl)oxycarbonyl]-2-propylpyrrolidine-2-carbonyl]indole-1-carboxylate Chemical compound C=1C=C2N(C(=O)OC(C)(C)C)C=CC2=CC=1C(=O)C1(CCC)CCCN1C(=O)OC(C)(C)C LUNFBLBGFLEXHS-UHFFFAOYSA-N 0.000 description 1
- RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 1
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- MYXKPFMQWULLOH-UHFFFAOYSA-M tetramethylazanium;hydroxide;pentahydrate Chemical compound O.O.O.O.O.[OH-].C[N+](C)(C)C MYXKPFMQWULLOH-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005304 thiadiazolidinyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000006090 thiamorpholinyl sulfone group Chemical group 0.000 description 1
- 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 208000028394 ureteral disease Diseases 0.000 description 1
- 201000001988 urethral stricture Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- NAUWTFJOPJWYOT-UHFFFAOYSA-N vanoxerine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)OCCN1CCN(CCCC=2C=CC=CC=2)CC1 NAUWTFJOPJWYOT-UHFFFAOYSA-N 0.000 description 1
- 229950007136 vanoxerine Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960004688 venlafaxine Drugs 0.000 description 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Pyridine Compounds (AREA)
- Seasonings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87596906P | 2006-12-19 | 2006-12-19 | |
| US60/875,969 | 2006-12-19 | ||
| US99956107P | 2007-10-19 | 2007-10-19 | |
| US60/999,561 | 2007-10-19 | ||
| PCT/EP2007/063736 WO2008074703A1 (en) | 2006-12-19 | 2007-12-11 | Heteroaryl pyrrolidinyl and piperidinyl ketone derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010513379A JP2010513379A (ja) | 2010-04-30 |
| JP2010513379A5 JP2010513379A5 (enExample) | 2010-10-14 |
| JP5394252B2 true JP5394252B2 (ja) | 2014-01-22 |
Family
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| EP2297096A2 (en) * | 2008-06-18 | 2011-03-23 | F. Hoffmann-La Roche AG | Aryl ketone as mri |
| EP2974724A1 (en) * | 2009-02-09 | 2016-01-20 | Sunovion Pharmaceuticals Inc. | Pyrrolidine triple reuptake inhibitors |
| JP5992192B2 (ja) * | 2012-03-30 | 2016-09-14 | 三井金属鉱業株式会社 | パラジウム触媒 |
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| CN105102448B (zh) | 2013-02-28 | 2018-03-06 | 百时美施贵宝公司 | 作为rock1和rock2抑制剂的苯基吡唑衍生物 |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| CN110642880B (zh) * | 2019-10-11 | 2021-12-31 | 长沙麓兴生物科技有限公司 | 一种氮未取代吡唑和吲唑类硼酸的制备方法 |
| CN114014792B (zh) * | 2021-12-15 | 2024-01-26 | 沈阳海诺威医药科技有限公司 | 一种7-(4-溴苯甲酰基)-1,3-二氢-2h-吲哚-2-酮的制备方法 |
| WO2023161533A1 (en) | 2022-02-28 | 2023-08-31 | Noema Pharma Ag | Triple uptake inhibitor for the treatment of atypical depression |
| CN116751157B (zh) * | 2023-06-21 | 2025-09-12 | 上海再启生物技术有限公司 | 一种2-(2-氨基-5-溴-苯甲酰基)吡啶的放大制备方法 |
| TW202525282A (zh) | 2023-08-28 | 2025-07-01 | 瑞士商諾埃瑪製藥公司 | 使用三重再攝取抑制劑治療行為免疫-代謝叢集病症或疾病之方法 |
| TW202515540A (zh) * | 2023-08-30 | 2025-04-16 | 瑞士商諾埃瑪製藥公司 | 使用三重再攝取抑制劑治療睡眠障礙之方法 |
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| WO2025146469A1 (en) * | 2024-01-05 | 2025-07-10 | Noema Pharma Ag | Treatment for the symptoms of menopause and perimenopause |
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