CA2641817A1 - Novel dual nk2/nk3-antagonists, pharmaceutical compositions comprising them and processes for their preparation - Google Patents
Novel dual nk2/nk3-antagonists, pharmaceutical compositions comprising them and processes for their preparation Download PDFInfo
- Publication number
- CA2641817A1 CA2641817A1 CA002641817A CA2641817A CA2641817A1 CA 2641817 A1 CA2641817 A1 CA 2641817A1 CA 002641817 A CA002641817 A CA 002641817A CA 2641817 A CA2641817 A CA 2641817A CA 2641817 A1 CA2641817 A1 CA 2641817A1
- Authority
- CA
- Canada
- Prior art keywords
- butyl
- phenyl
- methyl
- amino
- 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.)
- Abandoned
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- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 19
- 230000008569 process Effects 0.000 title claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 239000005557 antagonist Substances 0.000 title abstract description 11
- 230000009977 dual effect Effects 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 272
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 126
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 98
- -1 alkenylenearyl Chemical group 0.000 claims description 83
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
- 239000000126 substance Substances 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 27
- 101800000399 Neurokinin A Proteins 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 102400000097 Neurokinin A Human genes 0.000 claims description 20
- HEAUFJZALFKPBA-YRVBCFNBSA-N Neurokinin A Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CC=1NC=NC=1)C(C)O)C1=CC=CC=C1 HEAUFJZALFKPBA-YRVBCFNBSA-N 0.000 claims description 20
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- 102000005962 receptors Human genes 0.000 claims description 20
- 108020003175 receptors Proteins 0.000 claims description 20
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- NHXYSAFTNPANFK-HDMCBQFHSA-N Neurokinin B Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCSC)NC(=O)[C@@H](N)CC(O)=O)C1=CC=CC=C1 NHXYSAFTNPANFK-HDMCBQFHSA-N 0.000 claims description 17
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 17
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- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 238000011321 prophylaxis Methods 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
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- ISKNLVLNYHXEGD-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[furan-2-carbonyl(methyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CO1 ISKNLVLNYHXEGD-UHFFFAOYSA-N 0.000 claims description 7
- 102000015605 Neurokinin NK2 receptors Human genes 0.000 claims description 7
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- 102000019299 Neurokinin NK3 receptors Human genes 0.000 claims description 7
- 108050006653 Neurokinin NK3 receptors Proteins 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims description 6
- AQIDXHLJCYRPJC-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[(2-hydroxybenzoyl)-methylamino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=C1O AQIDXHLJCYRPJC-UHFFFAOYSA-N 0.000 claims description 6
- PZRSKQUTNSUOBV-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[(3,4-difluorobenzoyl)-methylamino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(F)C(F)=C1 PZRSKQUTNSUOBV-UHFFFAOYSA-N 0.000 claims description 6
- NJUNKHMZPFXNSI-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[(4-fluorobenzoyl)-methylamino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(F)C=C1 NJUNKHMZPFXNSI-UHFFFAOYSA-N 0.000 claims description 6
- ATSHWBFDWIFQNI-UHFFFAOYSA-N 1-[4-[(3-chloro-4-fluorobenzoyl)-methylamino]-3-(3,4-dichlorophenyl)butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(F)C(Cl)=C1 ATSHWBFDWIFQNI-UHFFFAOYSA-N 0.000 claims description 6
- ZLQJRGKTSNBQCK-UHFFFAOYSA-N 1-[4-[(3-cyanonaphthalene-1-carbonyl)-methylamino]-3-(3,4-dichlorophenyl)butyl]-n,n-dimethyl-4-pyrrolidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCC2)CCN1CCC(CN(C)C(=O)C=1C2=CC=CC=C2C=C(C=1)C#N)C1=CC=C(Cl)C(Cl)=C1 ZLQJRGKTSNBQCK-UHFFFAOYSA-N 0.000 claims description 6
- POHZDXGDXKNKJX-UHFFFAOYSA-N 1-[4-[benzoyl(methyl)amino]-3-(3,4-dichlorophenyl)butyl]-n-methyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=C1 POHZDXGDXKNKJX-UHFFFAOYSA-N 0.000 claims description 6
- NJHBAQCHVHPCOB-UHFFFAOYSA-N 1-[4-[cyclohexanecarbonyl(methyl)amino]-3-(3,4-dichlorophenyl)butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1CCCCC1 NJHBAQCHVHPCOB-UHFFFAOYSA-N 0.000 claims description 6
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- CWWARWOPSKGELM-SARDKLJWSA-N methyl (2s)-2-[[(2s)-2-[[2-[[(2s)-2-[[(2s)-2-[[(2s)-5-amino-2-[[(2s)-5-amino-2-[[(2s)-1-[(2s)-6-amino-2-[[(2s)-1-[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-5 Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)OC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 CWWARWOPSKGELM-SARDKLJWSA-N 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- HLXKKGDHXINWAL-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[(2,4-difluorobenzoyl)-methylamino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(F)C=C1F HLXKKGDHXINWAL-UHFFFAOYSA-N 0.000 claims description 5
- USGBVEBYQBIMFO-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[(2,5-difluorobenzoyl)-methylamino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC(F)=CC=C1F USGBVEBYQBIMFO-UHFFFAOYSA-N 0.000 claims description 5
- JJNRYXZYKYOVAZ-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[(4-methoxybenzoyl)-methylamino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)N(C)CC(C=1C=C(Cl)C(Cl)=CC=1)CCN1CCC(C(=O)N(C)C)(N2CCCCC2)CC1 JJNRYXZYKYOVAZ-UHFFFAOYSA-N 0.000 claims description 5
- RVVBQLRRKVKPIE-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl-(2-pyridin-3-ylacetyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)CC1=CC=CN=C1 RVVBQLRRKVKPIE-UHFFFAOYSA-N 0.000 claims description 5
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- SQEBKKMWSZSPPQ-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl-[3-(2,2,2-trifluoroethoxy)benzoyl]amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC(OCC(F)(F)F)=C1 SQEBKKMWSZSPPQ-UHFFFAOYSA-N 0.000 claims description 4
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- UENPGHVNWMRGPN-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[(2,6-difluorobenzoyl)-methylamino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=C(F)C=CC=C1F UENPGHVNWMRGPN-UHFFFAOYSA-N 0.000 claims description 3
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- POYKNBSQLAIBPQ-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[(4-hydroxybenzoyl)-methylamino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(O)C=C1 POYKNBSQLAIBPQ-UHFFFAOYSA-N 0.000 claims description 3
- NBHODWMMSRZYNF-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl(1h-pyrrole-2-carbonyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CN1 NBHODWMMSRZYNF-UHFFFAOYSA-N 0.000 claims description 3
- WLSCFIWETRGJCC-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl(oxane-4-carbonyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1CCOCC1 WLSCFIWETRGJCC-UHFFFAOYSA-N 0.000 claims description 3
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- MRBFWUSXMMJGRD-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl-(4-sulfamoylbenzoyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(S(N)(=O)=O)C=C1 MRBFWUSXMMJGRD-UHFFFAOYSA-N 0.000 claims description 3
- GXQXFWULROAHLX-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl-(5-methyl-1-phenyltriazole-4-carbonyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C(=C1C)N=NN1C1=CC=CC=C1 GXQXFWULROAHLX-UHFFFAOYSA-N 0.000 claims description 3
- PATGUBJUZWICCR-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl-[2-(methylamino)benzoyl]amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound CNC1=CC=CC=C1C(=O)N(C)CC(C=1C=C(Cl)C(Cl)=CC=1)CCN1CCC(C(=O)N(C)C)(N2CCCCC2)CC1 PATGUBJUZWICCR-UHFFFAOYSA-N 0.000 claims description 3
- OZOAQCHYVAUWGK-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl-[2-(trifluoromethyl)benzoyl]amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=C1C(F)(F)F OZOAQCHYVAUWGK-UHFFFAOYSA-N 0.000 claims description 3
- BZNJRPIKQVZUAU-UHFFFAOYSA-N 1-[4-[(2-bromobenzoyl)-methylamino]-3-(3,4-dichlorophenyl)butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=C1Br BZNJRPIKQVZUAU-UHFFFAOYSA-N 0.000 claims description 3
- MOIVBKGSTMFXOW-UHFFFAOYSA-N 1-[4-[(4-cyanobenzoyl)-methylamino]-3-(3,4-dichlorophenyl)butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(C#N)C=C1 MOIVBKGSTMFXOW-UHFFFAOYSA-N 0.000 claims description 3
- NFGHUAQKWYREFV-UHFFFAOYSA-N 1-[4-[1-benzofuran-5-carbonyl(methyl)amino]-3-(3,4-dichlorophenyl)butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(CN(C)C(=O)C=1C=C2C=COC2=CC=1)C1=CC=C(Cl)C(Cl)=C1 NFGHUAQKWYREFV-UHFFFAOYSA-N 0.000 claims description 3
- ZWPHABBLIHQXHO-UHFFFAOYSA-N 2-[[2-(3,4-dichlorophenyl)-4-[4-(dimethylcarbamoyl)-4-piperidin-1-ylpiperidin-1-yl]butyl]-methylcarbamoyl]benzoic acid Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=C1C(O)=O ZWPHABBLIHQXHO-UHFFFAOYSA-N 0.000 claims description 3
- KEIXILUEKCYJIH-UHFFFAOYSA-N 6-chloro-n-[2-(3,4-dichlorophenyl)-4-[4-(dimethylcarbamoyl)-4-piperidin-1-ylpiperidin-1-yl]butyl]-n-methylpyridine-3-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(Cl)N=C1 KEIXILUEKCYJIH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000002346 iodo group Chemical group I* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- GWAHPRGIRSJCPS-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)-4-[4-(dimethylcarbamoyl)-4-piperidin-1-ylpiperidin-1-yl]butyl]-n-methyl-1h-indole-5-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(CN(C)C(=O)C=1C=C2C=CNC2=CC=1)C1=CC=C(Cl)C(Cl)=C1 GWAHPRGIRSJCPS-UHFFFAOYSA-N 0.000 claims description 3
- ZBLUBMLVQXGFMP-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)-4-[4-(dimethylcarbamoyl)-4-piperidin-1-ylpiperidin-1-yl]butyl]-n-methylpyridine-2-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=N1 ZBLUBMLVQXGFMP-UHFFFAOYSA-N 0.000 claims description 3
- GLCBGODLYDGAPF-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)-4-[4-[1-(dimethylcarbamoyl)cyclohexyl]piperazin-1-yl]butyl]-n-methylbenzamide Chemical compound C1CN(CCC(CN(C)C(=O)C=2C=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)CCN1C1(C(=O)N(C)C)CCCCC1 GLCBGODLYDGAPF-UHFFFAOYSA-N 0.000 claims description 3
- HUTMEBZJFJTMFM-UHFFFAOYSA-N tert-butyl n-[2-(3,4-dichlorophenyl)-4-[4-(dimethylcarbamoyl)-4-piperidin-1-ylpiperidin-1-yl]butyl]-n-methylcarbamate Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(CN(C)C(=O)OC(C)(C)C)C1=CC=C(Cl)C(Cl)=C1 HUTMEBZJFJTMFM-UHFFFAOYSA-N 0.000 claims description 3
- PJELUVDAJNLYKU-UHFFFAOYSA-N tert-butyl n-[4-[[2-(3,4-dichlorophenyl)-4-[4-(dimethylcarbamoyl)-4-piperidin-1-ylpiperidin-1-yl]butyl]-methylcarbamoyl]phenyl]carbamate Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(NC(=O)OC(C)(C)C)C=C1 PJELUVDAJNLYKU-UHFFFAOYSA-N 0.000 claims description 3
- GKBOTAQMRIUENV-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[(2-fluorobenzoyl)-methylamino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=C1F GKBOTAQMRIUENV-UHFFFAOYSA-N 0.000 claims description 2
- BUWVVOWXRXTJSV-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[1h-imidazole-5-carbonyl(methyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CNC=N1 BUWVVOWXRXTJSV-UHFFFAOYSA-N 0.000 claims description 2
- WUBUXMPHKIJDHW-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[2,2-dimethylpropanoyl(methyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(CN(C)C(=O)C(C)(C)C)C1=CC=C(Cl)C(Cl)=C1 WUBUXMPHKIJDHW-UHFFFAOYSA-N 0.000 claims description 2
- INRHCGFGGNNBJV-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[3,3-diphenylpropanoyl(methyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 INRHCGFGGNNBJV-UHFFFAOYSA-N 0.000 claims description 2
- GNEZEAFZMBXBMM-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl(naphthalene-1-carbonyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(CN(C)C(=O)C=1C2=CC=CC=C2C=CC=1)C1=CC=C(Cl)C(Cl)=C1 GNEZEAFZMBXBMM-UHFFFAOYSA-N 0.000 claims description 2
- IVWCXLNRKNYXFG-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl(naphthalene-2-carbonyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(CN(C)C(=O)C=1C=C2C=CC=CC2=CC=1)C1=CC=C(Cl)C(Cl)=C1 IVWCXLNRKNYXFG-UHFFFAOYSA-N 0.000 claims description 2
- DKVJPZMSTIEZSZ-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl(thiophene-3-carbonyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C=1C=CSC=1 DKVJPZMSTIEZSZ-UHFFFAOYSA-N 0.000 claims description 2
- YLXMAZNXIKGYDG-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl-(4-methylbenzoyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(C)C=C1 YLXMAZNXIKGYDG-UHFFFAOYSA-N 0.000 claims description 2
- ZBVVVKXTGQRZSJ-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl-(4-oxochromene-2-carbonyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(CN(C)C(=O)C=1OC2=CC=CC=C2C(=O)C=1)C1=CC=C(Cl)C(Cl)=C1 ZBVVVKXTGQRZSJ-UHFFFAOYSA-N 0.000 claims description 2
- NKBYAOBJGJDBNC-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl-(4-phenylbenzoyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 NKBYAOBJGJDBNC-UHFFFAOYSA-N 0.000 claims description 2
- JLECATDJURPVEP-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl-(5-methyl-1-benzothiophene-2-carbonyl)amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(CN(C)C(=O)C=1SC2=CC=C(C)C=C2C=1)C1=CC=C(Cl)C(Cl)=C1 JLECATDJURPVEP-UHFFFAOYSA-N 0.000 claims description 2
- PJVDQOZUVNVTPB-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenyl)-4-[methyl-[4-(trifluoromethyl)benzoyl]amino]butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(C(F)(F)F)C=C1 PJVDQOZUVNVTPB-UHFFFAOYSA-N 0.000 claims description 2
- BDBOPQIYKOUMCD-UHFFFAOYSA-N 1-[4-[(2,6-dichlorobenzoyl)-methylamino]-3-(3,4-dichlorophenyl)butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=C(Cl)C=CC=C1Cl BDBOPQIYKOUMCD-UHFFFAOYSA-N 0.000 claims description 2
- XJRNUYYVKUOIKP-UHFFFAOYSA-N 1-[4-[(4-chloro-3-sulfamoylbenzoyl)-methylamino]-3-(3,4-dichlorophenyl)butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 XJRNUYYVKUOIKP-UHFFFAOYSA-N 0.000 claims description 2
- PXOMYJBTKZJHMB-UHFFFAOYSA-N 1-[4-[(4-chlorobenzoyl)-methylamino]-3-(3,4-dichlorophenyl)butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=C(Cl)C=C1 PXOMYJBTKZJHMB-UHFFFAOYSA-N 0.000 claims description 2
- OXWJTWWEOADQNN-UHFFFAOYSA-N 1-[4-[[3,5-bis(trifluoromethyl)benzoyl]-methylamino]-3-(3,4-dichlorophenyl)butyl]-n,n-dimethyl-4-piperidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OXWJTWWEOADQNN-UHFFFAOYSA-N 0.000 claims description 2
- BLJAQJGDGYEULO-UHFFFAOYSA-N 1-[4-[benzoyl(methyl)amino]-3-(3,4-dichlorophenyl)butyl]-N-methyl-N-propan-2-yl-4-pyrrolidin-1-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C(C)C)(N2CCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=C1 BLJAQJGDGYEULO-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- CQQMQYCKERICON-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)-4-[4-(dimethylcarbamoyl)-4-piperidin-1-ylpiperidin-1-yl]butyl]-5-(4-methoxyphenyl)-n-methyl-1,3-oxazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)N(C)CC(CCN2CCC(CC2)(N2CCCCC2)C(=O)N(C)C)C=2C=C(Cl)C(Cl)=CC=2)N=CO1 CQQMQYCKERICON-UHFFFAOYSA-N 0.000 claims description 2
- VSQYKIGUANUIRW-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)-4-[4-(dimethylcarbamoyl)-4-piperidin-1-ylpiperidin-1-yl]butyl]-n-methylpyrazine-2-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CN=CC=N1 VSQYKIGUANUIRW-UHFFFAOYSA-N 0.000 claims description 2
- SHCGZYBXCUZMIY-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)-4-[4-(dimethylcarbamoyl)-4-piperidin-1-ylpiperidin-1-yl]butyl]-n-methylpyridine-3-carboxamide Chemical compound C1CC(C(=O)N(C)C)(N2CCCCC2)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CN=C1 SHCGZYBXCUZMIY-UHFFFAOYSA-N 0.000 claims description 2
- FACKJZVQLOMIKL-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)-4-[4-(morpholine-4-carbonyl)-4-pyrrolidin-1-ylpiperidin-1-yl]butyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C)CC(C=1C=C(Cl)C(Cl)=CC=1)CCN(CC1)CCC1(C(=O)N1CCOCC1)N1CCCC1 FACKJZVQLOMIKL-UHFFFAOYSA-N 0.000 claims description 2
- PCFCSRXMUIVIQT-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)-4-[4-[(1-methylpiperidin-4-yl)-propanoylamino]piperidin-1-yl]butyl]-n-methylbenzamide Chemical compound C1CN(CCC(CN(C)C(=O)C=2C=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)CCC1N(C(=O)CC)C1CCN(C)CC1 PCFCSRXMUIVIQT-UHFFFAOYSA-N 0.000 claims description 2
- ICGBCSJEJYPUOY-UHFFFAOYSA-N n-[4-[4-[benzoyl(4-methoxybutyl)amino]piperidin-1-yl]-2-(3,4-dichlorophenyl)butyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(CCCCOC)C(CC1)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=C1 ICGBCSJEJYPUOY-UHFFFAOYSA-N 0.000 claims description 2
- WNJAZORJFZDKQB-UHFFFAOYSA-N n-[4-[4-[benzoyl(butyl)amino]piperidin-1-yl]-2-(3,4-dichlorophenyl)butyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(CCCC)C(CC1)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=C1 WNJAZORJFZDKQB-UHFFFAOYSA-N 0.000 claims description 2
- ZTIJBQSQLHYTOW-UHFFFAOYSA-N n-[4-[4-[benzoyl(cyclohexyl)amino]piperidin-1-yl]-2-(3,4-dichlorophenyl)butyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C)CC(C=1C=C(Cl)C(Cl)=CC=1)CCN(CC1)CCC1N(C(=O)C=1C=CC=CC=1)C1CCCCC1 ZTIJBQSQLHYTOW-UHFFFAOYSA-N 0.000 claims description 2
- KLXOVXVGRREQLV-UHFFFAOYSA-N n-[4-[4-[butyl(cyclohexanecarbonyl)amino]piperidin-1-yl]-2-(3,4-dichlorophenyl)butyl]-n-methylbenzamide Chemical compound C1CCCCC1C(=O)N(CCCC)C(CC1)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=C1 KLXOVXVGRREQLV-UHFFFAOYSA-N 0.000 claims description 2
- OXTCXJCWSYLMJL-UHFFFAOYSA-N n-[4-[4-[butyl(cyclopropanecarbonyl)amino]piperidin-1-yl]-2-(3,4-dichlorophenyl)butyl]-n-methylbenzamide Chemical compound C1CC1C(=O)N(CCCC)C(CC1)CCN1CCC(C=1C=C(Cl)C(Cl)=CC=1)CN(C)C(=O)C1=CC=CC=C1 OXTCXJCWSYLMJL-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- 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
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- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- 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
- A61P25/06—Antimigraine agents
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- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
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- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D409/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Otolaryngology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06101139 | 2006-02-01 | ||
EP06101139.1 | 2006-02-01 | ||
PCT/EP2007/050964 WO2007088181A1 (en) | 2006-02-01 | 2007-02-01 | Novel dual nk2/nk3-antagonists, pharmaceutical compositions comprising them and processes for their preparations |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2641817A1 true CA2641817A1 (en) | 2007-08-09 |
Family
ID=36564222
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002641817A Abandoned CA2641817A1 (en) | 2006-02-01 | 2007-02-01 | Novel dual nk2/nk3-antagonists, pharmaceutical compositions comprising them and processes for their preparation |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1979319A1 (de) |
JP (1) | JP2009525308A (de) |
CN (1) | CN101374811A (de) |
AU (1) | AU2007211475A1 (de) |
CA (1) | CA2641817A1 (de) |
RU (1) | RU2008135123A (de) |
WO (1) | WO2007088181A1 (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MX2010002585A (es) * | 2007-09-14 | 2010-03-26 | Hoffmann La Roche | Derivados de piperidina como antagonistas del receptor nk3. |
AR070398A1 (es) | 2008-02-22 | 2010-03-31 | Gruenenthal Chemie | Derivados sustituidos de indol |
MX2011003191A (es) * | 2008-10-14 | 2011-04-27 | Actelion Pharmaceuticals Ltd | Derivados de fenetilamida y sus analogos heterociclicos. |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI97540C (fi) * | 1989-11-06 | 1997-01-10 | Sanofi Sa | Menetelmä terapeuttisesti käyttökelpoisten, aromaattisesti substituoitujen piperidiini- ja piperatsiinijohdannaisten valmistamiseksi |
JPH10251228A (ja) * | 1997-03-06 | 1998-09-22 | Schering Plough Corp | ニューロキニンアンタゴニストとしてのピペリジン誘導体 |
US6365602B1 (en) * | 1998-07-10 | 2002-04-02 | Astra Zeneca Ab | N-substituted naphthalene carboxamides as neurokinin-receptor antagonists |
GB9922519D0 (en) * | 1998-10-07 | 1999-11-24 | Zeneca Ltd | Compounds |
FR2824828B1 (fr) * | 2001-05-21 | 2005-05-20 | Sanofi Synthelabo | Nouveaux derives de piperidinecarboxamide, un procede pour leur preparation et les compositions pharmaceutiques les contenant |
-
2007
- 2007-02-01 CN CNA2007800031296A patent/CN101374811A/zh active Pending
- 2007-02-01 EP EP07704286A patent/EP1979319A1/de not_active Withdrawn
- 2007-02-01 JP JP2008552803A patent/JP2009525308A/ja active Pending
- 2007-02-01 CA CA002641817A patent/CA2641817A1/en not_active Abandoned
- 2007-02-01 WO PCT/EP2007/050964 patent/WO2007088181A1/en active Application Filing
- 2007-02-01 AU AU2007211475A patent/AU2007211475A1/en not_active Abandoned
- 2007-02-01 RU RU2008135123/04A patent/RU2008135123A/ru not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
CN101374811A (zh) | 2009-02-25 |
JP2009525308A (ja) | 2009-07-09 |
EP1979319A1 (de) | 2008-10-15 |
AU2007211475A1 (en) | 2007-08-09 |
RU2008135123A (ru) | 2010-03-10 |
WO2007088181A1 (en) | 2007-08-09 |
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