JP2008542414A - ＭＧｌＵＲ５、セロトニン（５−ＨＴ）及びノルアドレナリン受容体の阻害剤としての置換されたＮ−ベンゾ［Ｄ］イソオキサゾール−３−イル−アミン誘導体及び医薬の製造へのその使用 - Google Patents

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Publication number

JP2008542414A

JP2008542414A JP2008515121A JP2008515121A JP2008542414A JP 2008542414 A JP2008542414 A JP 2008542414A JP 2008515121 A JP2008515121 A JP 2008515121A JP 2008515121 A JP2008515121 A JP 2008515121A JP 2008542414 A JP2008542414 A JP 2008542414A

Authority

JP

Japan

Prior art keywords

benzo

isoxazol

phenyl

group

butyl

Prior art date

2005-06-06

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.)

Ceased

Links

• Espacenet
• Global Dossier
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• 239000003814 drug Substances 0.000 title claims abstract description 117
• NLMVYUBGWZWUGB-UHFFFAOYSA-N 1,2-benzoxazol-3-amine Chemical class C1=CC=C2C(N)=NOC2=C1 NLMVYUBGWZWUGB-UHFFFAOYSA-N 0.000 title claims abstract description 62
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 23
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 title description 30
• 229960002748 norepinephrine Drugs 0.000 title description 15
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 title description 15
• 229940076279 serotonin Drugs 0.000 title description 7
• 239000003112 inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 55
• -1 3-nitrophenyl Chemical group 0.000 claims description 689
• 239000000460 chlorine Substances 0.000 claims description 241
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 187
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 184
• 229910052801 chlorine Inorganic materials 0.000 claims description 173
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 171
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 171
• 229910052731 fluorine Inorganic materials 0.000 claims description 169
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 169
• 229910052794 bromium Inorganic materials 0.000 claims description 168
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 167
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 148
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 148
• 125000001424 substituent group Chemical group 0.000 claims description 132
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 125
• 239000000203 mixture Substances 0.000 claims description 120
• 229910052740 iodine Inorganic materials 0.000 claims description 105
• 125000002541 furyl group Chemical group 0.000 claims description 66
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 55
• 208000002193 Pain Diseases 0.000 claims description 54
• 125000000217 alkyl group Chemical group 0.000 claims description 54
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 54
• 125000001624 naphthyl group Chemical group 0.000 claims description 53
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 51
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 51
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 51
• 150000003839 salts Chemical class 0.000 claims description 50
• 229940079593 drug Drugs 0.000 claims description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims description 44
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 44
• 230000002265 prevention Effects 0.000 claims description 44
• 125000001072 heteroaryl group Chemical group 0.000 claims description 42
• 125000004076 pyridyl group Chemical group 0.000 claims description 42
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 41
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
• 239000012453 solvate Substances 0.000 claims description 35
• 238000011282 treatment Methods 0.000 claims description 35
• 125000001544 thienyl group Chemical group 0.000 claims description 34
• 230000036407 pain Effects 0.000 claims description 30
• 230000033228 biological regulation Effects 0.000 claims description 28
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
• 201000010099 disease Diseases 0.000 claims description 26
• 208000011117 substance-related disease Diseases 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
• 125000004122 cyclic group Chemical group 0.000 claims description 25
• 125000002950 monocyclic group Chemical group 0.000 claims description 24
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 22
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 22
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 22
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 22
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 22
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 22
• 125000003136 n-heptyl 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])* 0.000 claims description 21
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 20
• 208000019695 Migraine disease Diseases 0.000 claims description 20
• 206010027599 migraine Diseases 0.000 claims description 20
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 20
• 238000000034 method Methods 0.000 claims description 18
• 230000004770 neurodegeneration Effects 0.000 claims description 18
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• 208000011580 syndromic disease Diseases 0.000 claims description 18
• 208000024827 Alzheimer disease Diseases 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 206010013663 drug dependence Diseases 0.000 claims description 15
• 208000030814 Eating disease Diseases 0.000 claims description 14
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 14
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
• 235000014632 disordered eating Nutrition 0.000 claims description 14
• 206010013654 Drug abuse Diseases 0.000 claims description 13
• 238000011161 development Methods 0.000 claims description 13
• 208000019901 Anxiety disease Diseases 0.000 claims description 12
• 208000032841 Bulimia Diseases 0.000 claims description 12
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 12
• 206010006895 Cachexia Diseases 0.000 claims description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
• 208000000094 Chronic Pain Diseases 0.000 claims description 12
• 208000008589 Obesity Diseases 0.000 claims description 12
• 206010033664 Panic attack Diseases 0.000 claims description 12
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
• 208000005298 acute pain Diseases 0.000 claims description 12
• 208000022531 anorexia Diseases 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 206010061428 decreased appetite Diseases 0.000 claims description 12
• 201000006417 multiple sclerosis Diseases 0.000 claims description 12
• 208000004296 neuralgia Diseases 0.000 claims description 12
• 208000021722 neuropathic pain Diseases 0.000 claims description 12
• 125000006344 nonafluoro n-butyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 12
• 235000020824 obesity Nutrition 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 239000001301 oxygen Substances 0.000 claims description 12
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 12
• 208000019906 panic disease Diseases 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 239000011593 sulfur Substances 0.000 claims description 12
• 208000009935 visceral pain Diseases 0.000 claims description 12
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 11
• 125000001931 aliphatic group Chemical group 0.000 claims description 11
• 125000005418 aryl aryl group Chemical group 0.000 claims description 11
• OUIKXEGSLDDELU-UHFFFAOYSA-N 2,4-difluoro-n-(5-fluoro-1,2-benzoxazol-3-yl)benzamide Chemical compound FC1=CC(F)=CC=C1C(=O)NC1=NOC2=CC=C(F)C=C12 OUIKXEGSLDDELU-UHFFFAOYSA-N 0.000 claims description 10
• CNZJQEQKYUQFSJ-UHFFFAOYSA-N 3-methyl-n-(5-methyl-1,2-benzoxazol-3-yl)benzamide Chemical compound CC1=CC=CC(C(=O)NC=2C3=CC(C)=CC=C3ON=2)=C1 CNZJQEQKYUQFSJ-UHFFFAOYSA-N 0.000 claims description 10
• 208000023105 Huntington disease Diseases 0.000 claims description 10
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 10
• 230000036506 anxiety Effects 0.000 claims description 10
• 230000001684 chronic effect Effects 0.000 claims description 10
• 230000007278 cognition impairment Effects 0.000 claims description 10
• 208000010877 cognitive disease Diseases 0.000 claims description 10
• 230000006735 deficit Effects 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 10
• 206010027175 memory impairment Diseases 0.000 claims description 10
• 125000002971 oxazolyl group Chemical group 0.000 claims description 10
• 239000012429 reaction media Substances 0.000 claims description 10
• 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 230000001419 dependent effect Effects 0.000 claims description 9
• 229940005483 opioid analgesics Drugs 0.000 claims description 9
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims description 8
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 8
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 8
• 201000006474 Brain Ischemia Diseases 0.000 claims description 8
• 206010008120 Cerebral ischaemia Diseases 0.000 claims description 8
• 206010011224 Cough Diseases 0.000 claims description 8
• 206010012735 Diarrhoea Diseases 0.000 claims description 8
• 208000007882 Gastritis Diseases 0.000 claims description 8
• 208000010412 Glaucoma Diseases 0.000 claims description 8
• 206010061218 Inflammation Diseases 0.000 claims description 8
• 208000007101 Muscle Cramp Diseases 0.000 claims description 8
• 208000004880 Polyuria Diseases 0.000 claims description 8
• 208000003251 Pruritus Diseases 0.000 claims description 8
• 208000005392 Spasm Diseases 0.000 claims description 8
• 208000007107 Stomach Ulcer Diseases 0.000 claims description 8
• 208000009205 Tinnitus Diseases 0.000 claims description 8
• 206010046543 Urinary incontinence Diseases 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 8
• 210000000748 cardiovascular system Anatomy 0.000 claims description 8
• 206010008118 cerebral infarction Diseases 0.000 claims description 8
• 230000035619 diuresis Effects 0.000 claims description 8
• 230000037406 food intake Effects 0.000 claims description 8
• 235000012631 food intake Nutrition 0.000 claims description 8
• 201000005917 gastric ulcer Diseases 0.000 claims description 8
• 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 8
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 8
• 230000004054 inflammatory process Effects 0.000 claims description 8
• 238000002690 local anesthesia Methods 0.000 claims description 8
• 230000008450 motivation Effects 0.000 claims description 8
• 201000003631 narcolepsy Diseases 0.000 claims description 8
• 230000001314 paroxysmal effect Effects 0.000 claims description 8
• 201000000980 schizophrenia Diseases 0.000 claims description 8
• 231100000886 tinnitus Toxicity 0.000 claims description 8
• 206010010904 Convulsion Diseases 0.000 claims description 7
• 230000036461 convulsion Effects 0.000 claims description 7
• 125000006017 1-propenyl group Chemical group 0.000 claims description 6
• 125000006020 2-methyl-1-propenyl group Chemical group 0.000 claims description 6
• 208000028698 Cognitive impairment Diseases 0.000 claims description 6
• 206010015037 epilepsy Diseases 0.000 claims description 6
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
• SMADCURPGFGGQH-UHFFFAOYSA-N n-(1,2-benzoxazol-3-yl)-2-ethylhexanamide Chemical compound C1=CC=C2C(NC(=O)C(CC)CCCC)=NOC2=C1 SMADCURPGFGGQH-UHFFFAOYSA-N 0.000 claims description 6
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 6
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• MRAXRKXTWDHXJQ-UHFFFAOYSA-N 2,3,4-trifluoro-n-(7-fluoro-1,2-benzoxazol-3-yl)benzamide Chemical compound FC1=C(F)C(F)=CC=C1C(=O)NC1=NOC2=C(F)C=CC=C12 MRAXRKXTWDHXJQ-UHFFFAOYSA-N 0.000 claims description 5
• VFGVMVSOIIDLGM-UHFFFAOYSA-N 2,3,4-trifluoro-n-[4-(2,2,2-trifluoroethoxy)-1,2-benzoxazol-3-yl]benzamide Chemical compound FC1=C(F)C(F)=CC=C1C(=O)NC1=NOC2=CC=CC(OCC(F)(F)F)=C12 VFGVMVSOIIDLGM-UHFFFAOYSA-N 0.000 claims description 5
• UBAPFTICGVRPFV-UHFFFAOYSA-N 2,3-difluoro-n-(5-methyl-1,2-benzoxazol-3-yl)benzamide Chemical compound C12=CC(C)=CC=C2ON=C1NC(=O)C1=CC=CC(F)=C1F UBAPFTICGVRPFV-UHFFFAOYSA-N 0.000 claims description 5
• QRCOZWLJUIHLHJ-UHFFFAOYSA-N 2,4-dichloro-5-fluoro-n-(7-fluoro-1,2-benzoxazol-3-yl)benzamide Chemical compound C1=C(Cl)C(F)=CC(C(=O)NC=2C3=CC=CC(F)=C3ON=2)=C1Cl QRCOZWLJUIHLHJ-UHFFFAOYSA-N 0.000 claims description 5
• ZLWOHMINYSPAHV-UHFFFAOYSA-N 2,4-dichloro-5-fluoro-n-[4-(2,2,2-trifluoroethoxy)-1,2-benzoxazol-3-yl]benzamide Chemical compound C1=C(Cl)C(F)=CC(C(=O)NC=2C3=C(OCC(F)(F)F)C=CC=C3ON=2)=C1Cl ZLWOHMINYSPAHV-UHFFFAOYSA-N 0.000 claims description 5
• MUGXKXYPQVUYJT-UHFFFAOYSA-N 2,4-dichloro-n-(6-chloro-1,2-benzoxazol-3-yl)-5-fluorobenzamide Chemical compound C1=C(Cl)C(F)=CC(C(=O)NC=2C3=CC=C(Cl)C=C3ON=2)=C1Cl MUGXKXYPQVUYJT-UHFFFAOYSA-N 0.000 claims description 5
• LJPCVPIKOGSYCS-UHFFFAOYSA-N 2,4-dichloro-n-[4-(dimethylamino)-1,2-benzoxazol-3-yl]-5-fluorobenzamide Chemical compound C1=2C(N(C)C)=CC=CC=2ON=C1NC(=O)C1=CC(F)=C(Cl)C=C1Cl LJPCVPIKOGSYCS-UHFFFAOYSA-N 0.000 claims description 5
• SRQSGBSZPWZQSR-UHFFFAOYSA-N 2,4-difluoro-n-(5-methyl-1,2-benzoxazol-3-yl)benzamide Chemical compound C12=CC(C)=CC=C2ON=C1NC(=O)C1=CC=C(F)C=C1F SRQSGBSZPWZQSR-UHFFFAOYSA-N 0.000 claims description 5
• JJNORKGNIHRRNQ-UHFFFAOYSA-N 2,5-dimethyl-N-[4-(2,2,2-trifluoroethoxy)-1,2-benzoxazol-3-yl]furan-3-carboxamide Chemical compound FC(COC1=CC=CC2=C1C(=NO2)NC(=O)C1=C(OC(=C1)C)C)(F)F JJNORKGNIHRRNQ-UHFFFAOYSA-N 0.000 claims description 5
• SKRPDVNNAFEZMA-UHFFFAOYSA-N 2-bromo-n-[4-(2,2,2-trifluoroethoxy)-1,2-benzoxazol-3-yl]benzamide Chemical compound C1=2C(OCC(F)(F)F)=CC=CC=2ON=C1NC(=O)C1=CC=CC=C1Br SKRPDVNNAFEZMA-UHFFFAOYSA-N 0.000 claims description 5
• YVCPQVAWAIPDCV-UHFFFAOYSA-N 2-chloro-n-(4-methoxy-1,2-benzoxazol-3-yl)benzamide Chemical compound C1=2C(OC)=CC=CC=2ON=C1NC(=O)C1=CC=CC=C1Cl YVCPQVAWAIPDCV-UHFFFAOYSA-N 0.000 claims description 5
• GKRYEUIMBDRHCV-UHFFFAOYSA-N 2-chloro-n-(5-methyl-1,2-benzoxazol-3-yl)pyridine-3-carboxamide Chemical compound C12=CC(C)=CC=C2ON=C1NC(=O)C1=CC=CN=C1Cl GKRYEUIMBDRHCV-UHFFFAOYSA-N 0.000 claims description 5
• MSBYOONDKHANNR-UHFFFAOYSA-N 2-chloro-n-(7-fluoro-1,2-benzoxazol-3-yl)pyridine-3-carboxamide Chemical compound N=1OC=2C(F)=CC=CC=2C=1NC(=O)C1=CC=CN=C1Cl MSBYOONDKHANNR-UHFFFAOYSA-N 0.000 claims description 5
• KGAQVXMWVNEGQT-UHFFFAOYSA-N 2-chloro-n-[4-(dimethylamino)-1,2-benzoxazol-3-yl]pyridine-3-carboxamide Chemical compound C1=2C(N(C)C)=CC=CC=2ON=C1NC(=O)C1=CC=CN=C1Cl KGAQVXMWVNEGQT-UHFFFAOYSA-N 0.000 claims description 5
• UVNCAPGXWXDHGU-UHFFFAOYSA-N 2-ethyl-n-(4-methoxy-1,2-benzoxazol-3-yl)hexanamide Chemical compound C1=CC(OC)=C2C(NC(=O)C(CC)CCCC)=NOC2=C1 UVNCAPGXWXDHGU-UHFFFAOYSA-N 0.000 claims description 5
• SAUCXEIGOACCNY-UHFFFAOYSA-N 2-fluoro-n-(7-fluoro-1,2-benzoxazol-3-yl)-3-(trifluoromethyl)benzamide Chemical compound N=1OC=2C(F)=CC=CC=2C=1NC(=O)C1=CC=CC(C(F)(F)F)=C1F SAUCXEIGOACCNY-UHFFFAOYSA-N 0.000 claims description 5
• BIFQLLCFLIHHDN-UHFFFAOYSA-N 2-fluoro-n-[4-(2,2,2-trifluoroethoxy)-1,2-benzoxazol-3-yl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC=C(C(F)(F)F)C(F)=C1C(=O)NC1=NOC2=CC=CC(OCC(F)(F)F)=C12 BIFQLLCFLIHHDN-UHFFFAOYSA-N 0.000 claims description 5
• GWNYLYKPLJRWEU-UHFFFAOYSA-N 2-methoxy-n-[4-(2,2,2-trifluoroethoxy)-1,2-benzoxazol-3-yl]benzamide Chemical compound COC1=CC=CC=C1C(=O)NC1=NOC2=CC=CC(OCC(F)(F)F)=C12 GWNYLYKPLJRWEU-UHFFFAOYSA-N 0.000 claims description 5
• LMWVKDQVVPNPKV-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1,2-benzoxazol-3-yl)pentanamide Chemical compound C1=C(C)C=C2C(NC(=O)C(C)CCC)=NOC2=C1 LMWVKDQVVPNPKV-UHFFFAOYSA-N 0.000 claims description 5
• CCIAZCCSWVZYNJ-UHFFFAOYSA-N 2-methyl-n-[4-(2,2,2-trifluoroethoxy)-1,2-benzoxazol-3-yl]butanamide Chemical compound C1=CC(OCC(F)(F)F)=C2C(NC(=O)C(C)CC)=NOC2=C1 CCIAZCCSWVZYNJ-UHFFFAOYSA-N 0.000 claims description 5
• QRBLRMOGFUAGQC-UHFFFAOYSA-N 3,3-dimethyl-n-[4-(2,2,2-trifluoroethoxy)-1,2-benzoxazol-3-yl]butanamide Chemical compound C1=CC(OCC(F)(F)F)=C2C(NC(=O)CC(C)(C)C)=NOC2=C1 QRBLRMOGFUAGQC-UHFFFAOYSA-N 0.000 claims description 5
• YEIWKZCIBSBSNG-UHFFFAOYSA-N 3,4-dichloro-n-(5-fluoro-1,2-benzoxazol-3-yl)benzamide Chemical compound C12=CC(F)=CC=C2ON=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 YEIWKZCIBSBSNG-UHFFFAOYSA-N 0.000 claims description 5
• DJZKAWSMIZNMBI-UHFFFAOYSA-N 3,4-dichloro-n-[4-(dimethylamino)-1,2-benzoxazol-3-yl]benzamide Chemical compound C1=2C(N(C)C)=CC=CC=2ON=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 DJZKAWSMIZNMBI-UHFFFAOYSA-N 0.000 claims description 5
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