MX2007007029A - Derivados de difenilurea utiles como activadores del canal de potasio. - Google Patents

Info

Publication number

MX2007007029A

MX2007007029A MX2007007029A MX2007007029A MX2007007029A MX 2007007029 A MX2007007029 A MX 2007007029A MX 2007007029 A MX2007007029 A MX 2007007029A MX 2007007029 A MX2007007029 A MX 2007007029A MX 2007007029 A MX2007007029 A MX 2007007029A

Authority

MX

Mexico

Prior art keywords

phenyl

urea

carbonyl

tetrazol

amino

Prior art date

2004-12-17

Links

• Espacenet
• Global Dossier
• Discuss

• GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical class C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 title claims abstract description 73
• 239000004036 potassium channel stimulating agent Substances 0.000 title description 3
• 238000000034 method Methods 0.000 claims abstract description 27
• 230000000414 obstructive effect Effects 0.000 claims abstract description 19
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 18
• 208000023504 respiratory system disease Diseases 0.000 claims abstract description 15
• 230000008499 blood brain barrier function Effects 0.000 claims abstract description 13
• 210000001218 blood-brain barrier Anatomy 0.000 claims abstract description 13
• 208000002193 Pain Diseases 0.000 claims abstract description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 142
• 239000001257 hydrogen Substances 0.000 claims description 134
• 229910052739 hydrogen Inorganic materials 0.000 claims description 134
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 127
• 125000001188 haloalkyl group Chemical group 0.000 claims description 117
• 239000004202 carbamide Substances 0.000 claims description 80
• 150000003839 salts Chemical class 0.000 claims description 44
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
• 241001465754 Metazoa Species 0.000 claims description 18
• 201000010099 disease Diseases 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 15
• 208000035475 disorder Diseases 0.000 claims description 12
• 230000035699 permeability Effects 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 238000011282 treatment Methods 0.000 claims description 11
• JVWZQRDKIMSXFY-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-[2-(2h-tetrazol-5-yl)-4-[3-(trifluoromethyl)phenyl]phenyl]urea Chemical group FC(F)(F)C1=CC=CC(C=2C=C(C(NC(=O)NC=3C=C(Cl)C=C(Cl)C=3)=CC=2)C=2NN=NN=2)=C1 JVWZQRDKIMSXFY-UHFFFAOYSA-N 0.000 claims description 6
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• 206010006451 bronchitis Diseases 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 206010035653 pneumoconiosis Diseases 0.000 claims description 4
• 208000015181 infectious disease Diseases 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• 208000033116 Asbestos intoxication Diseases 0.000 claims description 2
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
• 241000124008 Mammalia Species 0.000 claims description 2
• 201000010001 Silicosis Diseases 0.000 claims description 2
• 230000036428 airway hyperreactivity Effects 0.000 claims description 2
• 208000028462 aluminosis Diseases 0.000 claims description 2
• 208000010123 anthracosis Diseases 0.000 claims description 2
• 206010003441 asbestosis Diseases 0.000 claims description 2
• 125000006267 biphenyl group Chemical group 0.000 claims description 2
• 230000035874 hyperreactivity Effects 0.000 claims description 2
• 230000002685 pulmonary effect Effects 0.000 claims description 2
• 208000004003 siderosis Diseases 0.000 claims description 2
• 230000001684 chronic effect Effects 0.000 claims 3
• 230000000241 respiratory effect Effects 0.000 claims 3
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
• 208000019693 Lung disease Diseases 0.000 claims 2
• 230000001154 acute effect Effects 0.000 claims 2
• 206010069351 acute lung injury Diseases 0.000 claims 2
• 206010004485 Berylliosis Diseases 0.000 claims 1
• 206010006458 Bronchitis chronic Diseases 0.000 claims 1
• 208000023355 Chronic beryllium disease Diseases 0.000 claims 1
• 208000035473 Communicable disease Diseases 0.000 claims 1
• 206010014561 Emphysema Diseases 0.000 claims 1
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
• 206010047924 Wheezing Diseases 0.000 claims 1
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
• 208000007451 chronic bronchitis Diseases 0.000 claims 1
• 230000005713 exacerbation Effects 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 230000002458 infectious effect Effects 0.000 claims 1
• 208000027866 inflammatory disease Diseases 0.000 claims 1
• 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
• 208000002815 pulmonary hypertension Diseases 0.000 claims 1
• 230000029058 respiratory gaseous exchange Effects 0.000 claims 1
• 201000000306 sarcoidosis Diseases 0.000 claims 1
• 208000011580 syndromic disease Diseases 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 abstract description 75
• 230000001225 therapeutic effect Effects 0.000 abstract description 19
• 239000000126 substance Substances 0.000 abstract description 13
• 208000028017 Psychotic disease Diseases 0.000 abstract description 9
• 206010046543 Urinary incontinence Diseases 0.000 abstract description 8
• 206010015037 epilepsy Diseases 0.000 abstract description 8
• 208000024172 Cardiovascular disease Diseases 0.000 abstract description 7
• 238000002560 therapeutic procedure Methods 0.000 abstract description 4
• 239000003450 potassium channel blocker Substances 0.000 abstract description 2
• -1 hydroxy, carboxy Chemical group 0.000 description 316
• 125000005843 halogen group Chemical group 0.000 description 145
• 125000000217 alkyl group Chemical group 0.000 description 94
• 229910052757 nitrogen Inorganic materials 0.000 description 83
• 125000003545 alkoxy group Chemical group 0.000 description 81
• 150000002431 hydrogen Chemical group 0.000 description 80
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 73
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 57
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 45
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 39
• 125000004076 pyridyl group Chemical group 0.000 description 38
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 27
• 125000001309 chloro group Chemical group Cl* 0.000 description 27
• 125000001153 fluoro group Chemical group F* 0.000 description 27
• 125000001624 naphthyl group Chemical group 0.000 description 27
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 26
• 239000000203 mixture Substances 0.000 description 24
• 108091006146 Channels Proteins 0.000 description 22
• 239000003795 chemical substances by application Substances 0.000 description 22
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 22
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 21
• 125000004438 haloalkoxy group Chemical group 0.000 description 21
• 125000003831 tetrazolyl group Chemical group 0.000 description 20
• 125000003705 anilinocarbonyl group Chemical group O=C([*])N([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 19
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
• 125000001246 bromo group Chemical group Br* 0.000 description 17
• 239000000843 powder Substances 0.000 description 17
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 15
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 15
• 108010062745 Chloride Channels Proteins 0.000 description 14
• 239000004480 active ingredient Substances 0.000 description 14
• 125000002541 furyl group Chemical group 0.000 description 14
• 125000001544 thienyl group Chemical group 0.000 description 14
• 206010011224 Cough Diseases 0.000 description 13
• 229940117913 acrylamide Drugs 0.000 description 13
• 125000001715 oxadiazolyl group Chemical group 0.000 description 13
• 238000002360 preparation method Methods 0.000 description 13
• 239000000243 solution Substances 0.000 description 13
• 102000011045 Chloride Channels Human genes 0.000 description 12
• 239000003826 tablet Substances 0.000 description 12
• 125000001425 triazolyl group Chemical group 0.000 description 12
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 11
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 11
• 125000005059 halophenyl group Chemical group 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• 239000000443 aerosol Substances 0.000 description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
• 125000006485 halo alkoxy phenyl group Chemical group 0.000 description 10
• 239000007788 liquid Substances 0.000 description 9
• 239000007787 solid Substances 0.000 description 9
• LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 8
• 239000002775 capsule Substances 0.000 description 8
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 7
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 7
• 210000004556 brain Anatomy 0.000 description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
• 229940124597 therapeutic agent Drugs 0.000 description 7
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 description 6
• 239000000460 chlorine Chemical group 0.000 description 6
• 229910052801 chlorine Chemical group 0.000 description 6
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 6
• 230000001419 dependent effect Effects 0.000 description 6
• 208000028867 ischemia Diseases 0.000 description 6
• 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 6
• YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 6
• 230000008569 process Effects 0.000 description 6
• 210000002345 respiratory system Anatomy 0.000 description 6
• 239000003381 stabilizer Substances 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• TVWXEDPCVSYBGQ-UHFFFAOYSA-N 1-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[2-(2h-tetrazol-5-yl)-4-[4-(trifluoromethyl)phenyl]phenyl]urea Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)NC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1C1=NN=NN1 TVWXEDPCVSYBGQ-UHFFFAOYSA-N 0.000 description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• 102000004257 Potassium Channel Human genes 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
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• 230000000694 effects Effects 0.000 description 5
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• 238000002347 injection Methods 0.000 description 5
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• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
• 108020001213 potassium channel Proteins 0.000 description 5
• STTJZMMBQSFPDH-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-(4-chlorophenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(Cl)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC=CC=C1Br STTJZMMBQSFPDH-UHFFFAOYSA-N 0.000 description 4
• RRPYQUHLEGTJKV-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-(4-methylphenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(C)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC=CC=C1Br RRPYQUHLEGTJKV-UHFFFAOYSA-N 0.000 description 4
• UWSZMNDONFMCIR-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-[4-(4-chlorophenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(Cl)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC=CC=C1Cl UWSZMNDONFMCIR-UHFFFAOYSA-N 0.000 description 4
• KVEIODYPWIXAAF-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-[4-(4-fluorophenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(F)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC=CC=C1Cl KVEIODYPWIXAAF-UHFFFAOYSA-N 0.000 description 4
• FRARZGBCBZRGAC-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-[4-(4-methylphenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(C)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC=CC=C1Cl FRARZGBCBZRGAC-UHFFFAOYSA-N 0.000 description 4
• PLDWBDAUTRNKOA-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-[4-(4-fluorophenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(F)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC=CC=C1F PLDWBDAUTRNKOA-UHFFFAOYSA-N 0.000 description 4
• HGWWYBMJPPLPMC-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-[4-(4-methylphenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(C)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC=CC=C1F HGWWYBMJPPLPMC-UHFFFAOYSA-N 0.000 description 4
• VAZPJJNQTZFQGV-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-[2-(2h-tetrazol-5-yl)-4-[4-(trifluoromethoxy)phenyl]phenyl]urea Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 VAZPJJNQTZFQGV-UHFFFAOYSA-N 0.000 description 4
• SSQVNAXYGVSHKJ-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-[2-(2h-tetrazol-5-yl)-4-[4-(trifluoromethyl)phenyl]phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 SSQVNAXYGVSHKJ-UHFFFAOYSA-N 0.000 description 4
• IALUZRAHOQOYNZ-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-[4-(4-fluorophenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(F)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 IALUZRAHOQOYNZ-UHFFFAOYSA-N 0.000 description 4
• WRUGRLBBMZTCJI-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-[4-(4-methoxyphenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(OC)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 WRUGRLBBMZTCJI-UHFFFAOYSA-N 0.000 description 4
• LBSULNHRAYWAFG-UHFFFAOYSA-N 1-(3,5-difluorophenyl)-3-[4-(4-methoxyphenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(OC)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC(F)=CC(F)=C1 LBSULNHRAYWAFG-UHFFFAOYSA-N 0.000 description 4
• AYKYNSNOPJOWET-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(2h-tetrazol-5-yl)-4-[3-(trifluoromethyl)phenyl]phenyl]urea Chemical compound FC(F)(F)C1=CC=CC(C=2C=C(C(NC(=O)NC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=CC=2)C=2NN=NN=2)=C1 AYKYNSNOPJOWET-UHFFFAOYSA-N 0.000 description 4
• HPYCGQHGQFUEMU-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(2h-tetrazol-5-yl)-4-[4-(trifluoromethyl)phenyl]phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HPYCGQHGQFUEMU-UHFFFAOYSA-N 0.000 description 4
• YGXJGMBIXKVNQH-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[4-(4-fluorophenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(F)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YGXJGMBIXKVNQH-UHFFFAOYSA-N 0.000 description 4
• MUDICFFSDFNFSG-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[4-(4-methoxyphenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(OC)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 MUDICFFSDFNFSG-UHFFFAOYSA-N 0.000 description 4
• OIWJQMZHVFTYCF-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2-(2h-tetrazol-5-yl)phenyl]-3-(3,5-difluorophenyl)urea Chemical compound FC1=CC(F)=CC(NC(=O)NC=2C(=CC(=CC=2)C=2C=CC(Cl)=CC=2)C=2NN=NN=2)=C1 OIWJQMZHVFTYCF-UHFFFAOYSA-N 0.000 description 4
• HBKNWZPDQPKWAJ-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2-(2h-tetrazol-5-yl)phenyl]-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC=2C(=CC(=CC=2)C=2C=CC(Cl)=CC=2)C=2NN=NN=2)=C1 HBKNWZPDQPKWAJ-UHFFFAOYSA-N 0.000 description 4
• OIVVBSPPGHIDRT-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-2-(2h-tetrazol-5-yl)phenyl]-3-[2-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(F)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC=CC=C1C(F)(F)F OIVVBSPPGHIDRT-UHFFFAOYSA-N 0.000 description 4
• UDNYCFPUERVRMI-UHFFFAOYSA-N 1-[4-(4-methylphenyl)-2-(2h-tetrazol-5-yl)phenyl]-3-[2-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC=CC=C1C(F)(F)F UDNYCFPUERVRMI-UHFFFAOYSA-N 0.000 description 4
• WATPEFCWRLFZDL-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[2-(2h-tetrazol-5-yl)-4-[4-(trifluoromethyl)phenyl]phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 WATPEFCWRLFZDL-UHFFFAOYSA-N 0.000 description 4
• APRFKWLXMLMOKK-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-(4-fluorophenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C1=CC(F)=CC=C1C(C=C1C=2NN=NN=2)=CC=C1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 APRFKWLXMLMOKK-UHFFFAOYSA-N 0.000 description 4
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 4
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• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
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• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
• 230000032258 transport Effects 0.000 description 4
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