TWI265807B - Tachykinin receptor antagonists - Google Patents

Info

Publication number

TWI265807B

TWI265807B TW092109375A TW92109375A TWI265807B TW I265807 B TWI265807 B TW I265807B TW 092109375 A TW092109375 A TW 092109375A TW 92109375 A TW92109375 A TW 92109375A TW I265807 B TWI265807 B TW I265807B

Authority

TW

Taiwan

Prior art keywords

phenyl

trifluoromethyl

bis

group

benzyl

Prior art date

2002-04-26

Links

• Espacenet
• Global Dossier
• Discuss

• 239000002462 tachykinin receptor antagonist Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 352
• 150000003839 salts Chemical class 0.000 claims abstract description 40
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• -1 cumyl Chemical group 0.000 claims description 166
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 81
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 74
• 125000000217 alkyl group Chemical group 0.000 claims description 53
• 239000002253 acid Substances 0.000 claims description 51
• 229910052757 nitrogen Inorganic materials 0.000 claims description 47
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
• 208000019901 Anxiety disease Diseases 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 239000007789 gas Substances 0.000 claims description 13
• 230000036506 anxiety Effects 0.000 claims description 12
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 11
• 125000005843 halogen group Chemical group 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 150000002148 esters Chemical class 0.000 claims description 10
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• DCVWMMMKFZVEDP-UHFFFAOYSA-N 1-(cyclobutylmethyl)triazole-4-carboxylic acid Chemical compound N1=NC(C(=O)O)=CN1CC1CCC1 DCVWMMMKFZVEDP-UHFFFAOYSA-N 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• 239000007983 Tris buffer Substances 0.000 claims description 5
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
• 150000004820 halides Chemical class 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
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• 125000004429 atom Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• GTODOEDLCNTSLG-UHFFFAOYSA-N 2h-triazole-4-carboxylic acid Chemical compound OC(=O)C1=CNN=N1 GTODOEDLCNTSLG-UHFFFAOYSA-N 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
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• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
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• 125000004803 chlorobenzyl group Chemical group 0.000 claims description 2
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• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
• FNGUCCZRPLHTLF-UHFFFAOYSA-N C1COCCN1CC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F Chemical compound C1COCCN1CC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F FNGUCCZRPLHTLF-UHFFFAOYSA-N 0.000 claims 1
• 241000283070 Equus zebra Species 0.000 claims 1
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• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
• HSMPSHPWCOOUJH-UHFFFAOYSA-N anilinyl Chemical group [NH]C1=CC=CC=C1 HSMPSHPWCOOUJH-UHFFFAOYSA-N 0.000 claims 1
• 125000002837 carbocyclic group Chemical group 0.000 claims 1
• 125000000524 functional group Chemical group 0.000 claims 1
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• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 1
• 208000011580 syndromic disease Diseases 0.000 claims 1
• 238000002360 preparation method Methods 0.000 abstract description 161
• 238000000034 method Methods 0.000 abstract description 137
• 239000000543 intermediate Substances 0.000 abstract description 15
• 230000008569 process Effects 0.000 abstract description 6
• 102000007124 Tachykinin Receptors Human genes 0.000 abstract description 5
• 108010072901 Tachykinin Receptors Proteins 0.000 abstract description 5
• 239000003112 inhibitor Substances 0.000 abstract description 2
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 470
• 235000019439 ethyl acetate Nutrition 0.000 description 419
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 335
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 196
• 101150041968 CDC13 gene Proteins 0.000 description 194
• 238000005481 NMR spectroscopy Methods 0.000 description 193
• 239000000243 solution Substances 0.000 description 151
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 146
• 238000006243 chemical reaction Methods 0.000 description 143
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 132
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 116
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
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