NZ535886A - Triazole derivatives as tachykinin receptor antagonists - Google Patents

Info

Publication number

NZ535886A

NZ535886A NZ535886A NZ53588603A NZ535886A NZ 535886 A NZ535886 A NZ 535886A NZ 535886 A NZ535886 A NZ 535886A NZ 53588603 A NZ53588603 A NZ 53588603A NZ 535886 A NZ535886 A NZ 535886A

Authority

NZ

New Zealand

Prior art keywords

phenyl

trifluoromethyl

benzyl

chloro

bis

Prior art date

2002-04-26

Links

• Espacenet
• Global Dossier
• Discuss

• 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title abstract description 3
• 239000002462 tachykinin receptor antagonist Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 383
• -1 cyano, difluoromethyl Chemical group 0.000 claims abstract description 81
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 54
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 44
• 150000003839 salts Chemical class 0.000 claims abstract description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
• 239000001257 hydrogen Substances 0.000 claims abstract description 23
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 20
• 238000011282 treatment Methods 0.000 claims abstract description 19
• 125000001424 substituent group Chemical group 0.000 claims abstract description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 13
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 11
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 10
• 230000036506 anxiety Effects 0.000 claims abstract description 10
• 206010047700 Vomiting Diseases 0.000 claims abstract description 9
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 7
• 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• 125000002541 furyl group Chemical group 0.000 claims abstract description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 4
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 4
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
• 125000005554 pyridyloxy group Chemical group 0.000 claims abstract description 3
• 125000001475 halogen functional group Chemical group 0.000 claims abstract 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 74
• DCVWMMMKFZVEDP-UHFFFAOYSA-N 1-(cyclobutylmethyl)triazole-4-carboxylic acid Chemical compound N1=NC(C(=O)O)=CN1CC1CCC1 DCVWMMMKFZVEDP-UHFFFAOYSA-N 0.000 claims description 55
• 229910052757 nitrogen Inorganic materials 0.000 claims description 42
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 125000004429 atom Chemical group 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 239000011593 sulfur Substances 0.000 claims description 5
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
• DYUZKVKGQMWOHS-UHFFFAOYSA-N 5-(1-benzyltriazol-4-yl)-1-phenyltetrazole Chemical compound C1=C(C=2N(N=NN=2)C=2C=CC=CC=2)N=NN1CC1=CC=CC=C1 DYUZKVKGQMWOHS-UHFFFAOYSA-N 0.000 claims description 2
• 208000011688 Generalised anxiety disease Diseases 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 208000029364 generalized anxiety disease Diseases 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• RCRKCUFVQRCCSF-UHFFFAOYSA-N tert-butyl n-[2-[[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-morpholin-4-yltriazole-4-carbonyl]-[1-(2-chlorophenyl)ethyl]amino]ethyl]carbamate Chemical compound C=1C=CC=C(Cl)C=1C(C)N(CCNC(=O)OC(C)(C)C)C(=O)C(=C1N2CCOCC2)N=NN1CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RCRKCUFVQRCCSF-UHFFFAOYSA-N 0.000 claims description 2
• 239000000556 agonist Substances 0.000 claims 3
• 238000002347 injection Methods 0.000 claims 3
• 239000007924 injection Substances 0.000 claims 3
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• 238000001061 Dunnett's test Methods 0.000 claims 1
• PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 claims 1
• 241001465754 Metazoa Species 0.000 claims 1
• HCHJXHAOUWWKJY-UHFFFAOYSA-N N'-[(2-chlorophenyl)methyl]ethane-1,2-diamine hydrochloride Chemical compound Cl.NCCNCC1=CC=CC=C1Cl HCHJXHAOUWWKJY-UHFFFAOYSA-N 0.000 claims 1
• IEKZHGDJTCWRKC-UHFFFAOYSA-N N'-[1-(2-chlorophenyl)ethyl]ethane-1,2-diamine dihydrochloride Chemical compound Cl.Cl.NCCNC(C)C1=CC=CC=C1Cl IEKZHGDJTCWRKC-UHFFFAOYSA-N 0.000 claims 1
• 241000080590 Niso Species 0.000 claims 1
• 229920005372 Plexiglas® Polymers 0.000 claims 1
• WDWKUSVIIQGHQR-UHFFFAOYSA-N [2-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-pyrazin-2-yltriazol-4-yl]pyridin-3-yl]-(2-chlorophenyl)methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CN2C(=C(N=N2)C=2C(=CC=CN=2)C(=O)C=2C(=CC=CC=2)Cl)C=2N=CC=NC=2)=C1 WDWKUSVIIQGHQR-UHFFFAOYSA-N 0.000 claims 1
• BXFJVJCTOXNGQB-UHFFFAOYSA-N [2-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-pyridin-3-yltriazol-4-yl]pyridin-3-yl]-(2-chlorophenyl)methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CN2C(=C(N=N2)C=2C(=CC=CN=2)C(=O)C=2C(=CC=CC=2)Cl)C=2C=NC=CC=2)=C1 BXFJVJCTOXNGQB-UHFFFAOYSA-N 0.000 claims 1
• WQEHSGBEFASOHS-UHFFFAOYSA-N [2-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-pyridin-4-yltriazol-4-yl]pyridin-3-yl]-(2-fluorophenyl)methanone Chemical compound FC1=CC=CC=C1C(=O)C1=CC=CN=C1C1=C(C=2C=CN=CC=2)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)N=N1 WQEHSGBEFASOHS-UHFFFAOYSA-N 0.000 claims 1
• DKHLRIALSSMNMH-UHFFFAOYSA-N [2-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-pyridin-4-yltriazol-4-yl]pyridin-3-yl]-phenylmethanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CN2C(=C(N=N2)C=2C(=CC=CN=2)C(=O)C=2C=CC=CC=2)C=2C=CN=CC=2)=C1 DKHLRIALSSMNMH-UHFFFAOYSA-N 0.000 claims 1
• SJMNZGLLWWUYIN-UHFFFAOYSA-N [3-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-pyridin-4-yltriazol-4-yl]-5-(2-hydroxypropan-2-yl)-1,2-oxazol-4-yl]-(2-chlorophenyl)methanone Chemical compound C=1C=CC=C(Cl)C=1C(=O)C1=C(C(C)(O)C)ON=C1C(=C1C=2C=CN=CC=2)N=NN1CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SJMNZGLLWWUYIN-UHFFFAOYSA-N 0.000 claims 1
• CGQHWJPXQWVUQD-UHFFFAOYSA-N [5-amino-3-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-pyridin-4-yltriazol-4-yl]pyridazin-4-yl]-(2-chlorophenyl)methanone Chemical compound C=1C=CC=C(Cl)C=1C(=O)C=1C(N)=CN=NC=1C(=C1C=2C=CN=CC=2)N=NN1CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CGQHWJPXQWVUQD-UHFFFAOYSA-N 0.000 claims 1
• 230000037005 anaesthesia Effects 0.000 claims 1
• 238000000540 analysis of variance Methods 0.000 claims 1
• 238000013480 data collection Methods 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 210000000548 hind-foot Anatomy 0.000 claims 1
• 238000003780 insertion Methods 0.000 claims 1
• 230000037431 insertion Effects 0.000 claims 1
• 238000000185 intracerebroventricular administration Methods 0.000 claims 1
• 229960002725 isoflurane Drugs 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• 239000004926 polymethyl methacrylate Substances 0.000 claims 1
• 238000010079 rubber tapping Methods 0.000 claims 1
• 238000012360 testing method Methods 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 136
• 238000002360 preparation method Methods 0.000 abstract description 125
• 150000003852 triazoles Chemical class 0.000 abstract description 37
• 239000000543 intermediate Substances 0.000 abstract description 16
• 102000007124 Tachykinin Receptors Human genes 0.000 abstract description 7
• 108010072901 Tachykinin Receptors Proteins 0.000 abstract description 7
• 230000008569 process Effects 0.000 abstract description 3
• 239000003112 inhibitor Substances 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 722
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 639
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 355
• 235000019439 ethyl acetate Nutrition 0.000 description 341
• 238000004809 thin layer chromatography Methods 0.000 description 220
• 239000000243 solution Substances 0.000 description 186
• 238000005481 NMR spectroscopy Methods 0.000 description 182
• 239000012141 concentrate Substances 0.000 description 162
• 235000008504 concentrate Nutrition 0.000 description 162
• 238000003756 stirring Methods 0.000 description 148
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 144
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 138
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 126
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 123
• 239000000047 product Substances 0.000 description 106
• 238000006243 chemical reaction Methods 0.000 description 102
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 93
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 92
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
• 101150041968 CDC13 gene Proteins 0.000 description 90
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
• 229910001868 water Inorganic materials 0.000 description 82
• 239000000203 mixture Substances 0.000 description 80
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 78
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• 238000001819 mass spectrum Methods 0.000 description 66
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 64
• 229920006395 saturated elastomer Polymers 0.000 description 62
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• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 20
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 19
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• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
• 125000006239 protecting group Chemical group 0.000 description 16
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• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
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