NZ549133A - Substituted morpholine and thiomorpholine derivatives - Google Patents

Info

Publication number

NZ549133A

NZ549133A NZ549133A NZ54913305A NZ549133A NZ 549133 A NZ549133 A NZ 549133A NZ 549133 A NZ549133 A NZ 549133A NZ 54913305 A NZ54913305 A NZ 54913305A NZ 549133 A NZ549133 A NZ 549133A

Authority

NZ

New Zealand

Prior art keywords

phenyl

morpholin

acetamide

dimethyl

alk

Prior art date

2004-03-12

Links

• Espacenet
• Global Dossier
• Discuss

• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title claims abstract description 19
• 150000002780 morpholines Chemical class 0.000 title claims abstract description 13
• 150000004886 thiomorpholines Chemical class 0.000 title claims abstract description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 227
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 71
• 201000010099 disease Diseases 0.000 claims abstract description 39
• 108020001213 potassium channel Proteins 0.000 claims abstract description 26
• 102000004257 Potassium Channel Human genes 0.000 claims abstract description 25
• 206010015037 epilepsy Diseases 0.000 claims abstract description 24
• 238000011282 treatment Methods 0.000 claims abstract description 23
• -1 2-methyl-4-morpholin-4-yl-6-trifluoromethyl-phenyl Chemical group 0.000 claims description 42
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 42
• 208000019901 Anxiety disease Diseases 0.000 claims description 40
• 206010010904 Convulsion Diseases 0.000 claims description 37
• 208000035475 disorder Diseases 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 229910052736 halogen Inorganic materials 0.000 claims description 26
• 150000002367 halogens Chemical class 0.000 claims description 24
• 208000004296 neuralgia Diseases 0.000 claims description 24
• 208000021722 neuropathic pain Diseases 0.000 claims description 24
• 230000000694 effects Effects 0.000 claims description 21
• 238000012360 testing method Methods 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 15
• 239000000126 substance Substances 0.000 claims description 14
• 208000019695 Migraine disease Diseases 0.000 claims description 13
• 230000036506 anxiety Effects 0.000 claims description 13
• 206010027599 migraine Diseases 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 230000001537 neural effect Effects 0.000 claims description 12
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 239000012458 free base Substances 0.000 claims description 9
• 230000004770 neurodegeneration Effects 0.000 claims description 9
• BKYHSCLAVOQZHZ-UHFFFAOYSA-N 2,6-dimethyl-4-morpholin-4-ylaniline Chemical compound CC1=C(N)C(C)=CC(N2CCOCC2)=C1 BKYHSCLAVOQZHZ-UHFFFAOYSA-N 0.000 claims description 8
• 208000014644 Brain disease Diseases 0.000 claims description 8
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• 208000002193 Pain Diseases 0.000 claims description 8
• 208000027520 Somatoform disease Diseases 0.000 claims description 8
• 208000027753 pain disease Diseases 0.000 claims description 8
• 229940080818 propionamide Drugs 0.000 claims description 8
• 206010001497 Agitation Diseases 0.000 claims description 7
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• 241000699670 Mus sp. Species 0.000 claims description 7
• 206010034912 Phobia Diseases 0.000 claims description 7
• 201000001716 specific phobia Diseases 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 241001465754 Metazoa Species 0.000 claims description 6
• 241000700159 Rattus Species 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 208000030507 AIDS Diseases 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• 241000589968 Borrelia Species 0.000 claims description 5
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 5
• 208000011688 Generalised anxiety disease Diseases 0.000 claims description 5
• 208000004454 Hyperalgesia Diseases 0.000 claims description 5
• 201000001916 Hypochondriasis Diseases 0.000 claims description 5
• 208000016604 Lyme disease Diseases 0.000 claims description 5
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• 208000004983 Phantom Limb Diseases 0.000 claims description 5
• 206010056238 Phantom pain Diseases 0.000 claims description 5
• 241000710799 Rubella virus Species 0.000 claims description 5
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• 208000012826 adjustment disease Diseases 0.000 claims description 5
• 206010053552 allodynia Diseases 0.000 claims description 5
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
• 210000003169 central nervous system Anatomy 0.000 claims description 5
• 230000036461 convulsion Effects 0.000 claims description 5
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• 208000015181 infectious disease Diseases 0.000 claims description 5
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• 230000035987 intoxication Effects 0.000 claims description 5
• 231100000566 intoxication Toxicity 0.000 claims description 5
• 201000006417 multiple sclerosis Diseases 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 244000052769 pathogen Species 0.000 claims description 5
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• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 5
• 208000005809 status epilepticus Diseases 0.000 claims description 5
• 230000008733 trauma Effects 0.000 claims description 5
• 241001529453 unidentified herpesvirus Species 0.000 claims description 5
• VUAMDENGEUCDEU-UHFFFAOYSA-N 2-cycloheptyl-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1CCCCCC1 VUAMDENGEUCDEU-UHFFFAOYSA-N 0.000 claims description 4
• KDEDDVIUECCASI-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dimethyl-4-(2-phenylmorpholin-4-yl)phenyl]acetamide Chemical compound CC1=CC(N2CC(OCC2)C=2C=CC=CC=2)=CC(C)=C1NC(=O)CC1CCCC1 KDEDDVIUECCASI-UHFFFAOYSA-N 0.000 claims description 4
• 208000023105 Huntington disease Diseases 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• 208000018737 Parkinson disease Diseases 0.000 claims description 4
• 208000000810 Separation Anxiety Diseases 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• WZMQBLIZLSZDTE-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)heptanamide Chemical compound C1=C(C)C(NC(=O)CCCCCC)=C(C)C=C1N1CCOCC1 WZMQBLIZLSZDTE-UHFFFAOYSA-N 0.000 claims description 4
• RJPNBZXKFWESKX-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)hexanamide Chemical compound C1=C(C)C(NC(=O)CCCCC)=C(C)C=C1N1CCOCC1 RJPNBZXKFWESKX-UHFFFAOYSA-N 0.000 claims description 4
• ZYQZHRXKSVPLEG-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)octanamide Chemical compound C1=C(C)C(NC(=O)CCCCCCC)=C(C)C=C1N1CCOCC1 ZYQZHRXKSVPLEG-UHFFFAOYSA-N 0.000 claims description 4
• ORMUPENLTSWLSB-UHFFFAOYSA-N n-(2-chloro-6-cyano-4-morpholin-4-ylphenyl)-3-cyclohexylpropanamide Chemical compound ClC1=CC(N2CCOCC2)=CC(C#N)=C1NC(=O)CCC1CCCCC1 ORMUPENLTSWLSB-UHFFFAOYSA-N 0.000 claims description 4
• 208000019906 panic disease Diseases 0.000 claims description 4
• FDONRMIZVSGMJB-UHFFFAOYSA-N (2-chlorophenyl)methyl n-(2,6-dimethyl-4-morpholin-4-ylphenyl)carbamate Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)OCC1=CC=CC=C1Cl FDONRMIZVSGMJB-UHFFFAOYSA-N 0.000 claims description 3
• ILHJZFCXQIZPDX-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanyl)-n-(2,6-difluoro-4-morpholin-4-ylphenyl)acetamide Chemical compound C=1C(F)=C(NC(=O)CC2C3CCC(C3)C2)C(F)=CC=1N1CCOCC1 ILHJZFCXQIZPDX-UHFFFAOYSA-N 0.000 claims description 3
• NWZHLVIUDQICHI-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=C(Cl)C=C1 NWZHLVIUDQICHI-UHFFFAOYSA-N 0.000 claims description 3
• SHIXPWQRHRYAPF-UHFFFAOYSA-N 2-cyclopent-2-en-1-yl-n-(2,6-difluoro-4-morpholin-4-ylphenyl)acetamide Chemical compound FC1=CC(N2CCOCC2)=CC(F)=C1NC(=O)CC1CCC=C1 SHIXPWQRHRYAPF-UHFFFAOYSA-N 0.000 claims description 3
• IAAITAGXZWCRTQ-UHFFFAOYSA-N 2-cyclopentyl-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1CCCC1 IAAITAGXZWCRTQ-UHFFFAOYSA-N 0.000 claims description 3
• IKPVUBMYZIWNRW-UHFFFAOYSA-N 2-cyclopentyl-n-(2,6-dimethyl-4-thiomorpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCSCC2)=CC(C)=C1NC(=O)CC1CCCC1 IKPVUBMYZIWNRW-UHFFFAOYSA-N 0.000 claims description 3
• SEMYLXWJGQSZRH-UHFFFAOYSA-N 2-cyclopentyl-n-[4-morpholin-4-yl-2,6-di(propan-2-yl)phenyl]acetamide Chemical compound CC(C)C1=CC(N2CCOCC2)=CC(C(C)C)=C1NC(=O)CC1CCCC1 SEMYLXWJGQSZRH-UHFFFAOYSA-N 0.000 claims description 3
• XWLHXKMXYSTIJX-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)propanamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CCC1=CC=C(F)C(F)=C1 XWLHXKMXYSTIJX-UHFFFAOYSA-N 0.000 claims description 3
• FFJSHGKHOFZMRC-UHFFFAOYSA-N 3-cyclohexyl-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)propanamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CCC1CCCCC1 FFJSHGKHOFZMRC-UHFFFAOYSA-N 0.000 claims description 3
• FQHLBMKMJMGTSG-UHFFFAOYSA-N 3-cyclopentyl-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)propanamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CCC1CCCC1 FQHLBMKMJMGTSG-UHFFFAOYSA-N 0.000 claims description 3
• OGABBSFCFIJRPK-UHFFFAOYSA-N 5-methyl-n-[2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]hexanamide Chemical compound C1=C(C(F)(F)F)C(NC(=O)CCCC(C)C)=C(C)C=C1N1CCOCC1 OGABBSFCFIJRPK-UHFFFAOYSA-N 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 208000012902 Nervous system disease Diseases 0.000 claims description 3
• 206010029240 Neuritis Diseases 0.000 claims description 3
• 206010036105 Polyneuropathy Diseases 0.000 claims description 3
• DDAWRADOFRFSCU-UHFFFAOYSA-N benzyl n-(2,6-dimethyl-4-morpholin-4-ylphenyl)carbamate Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)OCC1=CC=CC=C1 DDAWRADOFRFSCU-UHFFFAOYSA-N 0.000 claims description 3
• CSWQFUWZYDMBLR-UHFFFAOYSA-N butyl n-(2,6-dimethyl-4-morpholin-4-ylphenyl)carbamate Chemical compound C1=C(C)C(NC(=O)OCCCC)=C(C)C=C1N1CCOCC1 CSWQFUWZYDMBLR-UHFFFAOYSA-N 0.000 claims description 3
• 208000015114 central nervous system disease Diseases 0.000 claims description 3
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
• BPFWCATXXHFMHU-UHFFFAOYSA-N n-(2,6-difluoro-4-morpholin-4-ylphenyl)hexanamide Chemical compound C1=C(F)C(NC(=O)CCCCC)=C(F)C=C1N1CCOCC1 BPFWCATXXHFMHU-UHFFFAOYSA-N 0.000 claims description 3
• BHJCRISXCWZQNL-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-(3-methylphenyl)acetamide Chemical compound CC1=CC=CC(CC(=O)NC=2C(=CC(=CC=2C)N2CCOCC2)C)=C1 BHJCRISXCWZQNL-UHFFFAOYSA-N 0.000 claims description 3
• FQXJKHBCIJGCQO-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-(4-fluorophenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 FQXJKHBCIJGCQO-UHFFFAOYSA-N 0.000 claims description 3
• WZSQCEVOMHBPFJ-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-[3-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1 WZSQCEVOMHBPFJ-UHFFFAOYSA-N 0.000 claims description 3
• IQZIDXSIVOBHBG-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-thiophen-2-ylacetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=CS1 IQZIDXSIVOBHBG-UHFFFAOYSA-N 0.000 claims description 3
• OVEJXWFUXCATFY-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=CC(N2CCOCC2)=C1 OVEJXWFUXCATFY-UHFFFAOYSA-N 0.000 claims description 3
• UULFYDWHIRAODG-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-3,5,5-trimethylhexanamide Chemical compound C1=C(C)C(NC(=O)CC(C)CC(C)(C)C)=C(C)C=C1N1CCOCC1 UULFYDWHIRAODG-UHFFFAOYSA-N 0.000 claims description 3
• CPXXAHUMOPUBQF-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-3-ethylpentanamide Chemical compound C1=C(C)C(NC(=O)CC(CC)CC)=C(C)C=C1N1CCOCC1 CPXXAHUMOPUBQF-UHFFFAOYSA-N 0.000 claims description 3
• KWQRIEAEGLFRKZ-UHFFFAOYSA-N n-(2-chloro-6-methyl-4-morpholin-4-ylphenyl)-2-cyclopentylacetamide Chemical compound CC1=CC(N2CCOCC2)=CC(Cl)=C1NC(=O)CC1CCCC1 KWQRIEAEGLFRKZ-UHFFFAOYSA-N 0.000 claims description 3
• BZNCUGFPSDUISB-UHFFFAOYSA-N n-(2-methoxy-6-methyl-4-morpholin-4-ylphenyl)-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(OC)=CC(N2CCOCC2)=C1 BZNCUGFPSDUISB-UHFFFAOYSA-N 0.000 claims description 3
• LDGIJFPFNRCERN-UHFFFAOYSA-N n-(2-methoxy-6-methyl-4-morpholin-4-ylphenyl)-5-methylhexanamide Chemical compound CC1=C(NC(=O)CCCC(C)C)C(OC)=CC(N2CCOCC2)=C1 LDGIJFPFNRCERN-UHFFFAOYSA-N 0.000 claims description 3
• RUDPUVCWGIFSRS-UHFFFAOYSA-N n-(2-methoxy-6-methyl-4-morpholin-4-ylphenyl)hexanamide Chemical compound C1=C(OC)C(NC(=O)CCCCC)=C(C)C=C1N1CCOCC1 RUDPUVCWGIFSRS-UHFFFAOYSA-N 0.000 claims description 3
• WOVDEFIGDUUBDM-UHFFFAOYSA-N n-[2-bromo-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]propanamide Chemical compound C1=C(C(F)(F)F)C(NC(=O)CC)=C(Br)C=C1N1CCOCC1 WOVDEFIGDUUBDM-UHFFFAOYSA-N 0.000 claims description 3
• ROGXWDNMPNMNEI-UHFFFAOYSA-N n-[2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]hexanamide Chemical compound C1=C(C(F)(F)F)C(NC(=O)CCCCC)=C(C)C=C1N1CCOCC1 ROGXWDNMPNMNEI-UHFFFAOYSA-N 0.000 claims description 3
• 230000007824 polyneuropathy Effects 0.000 claims description 3
• IRYKZAAWGNDZJR-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=C(F)C(F)=C1 IRYKZAAWGNDZJR-UHFFFAOYSA-N 0.000 claims description 2
• GTZXKLYUHHQHSC-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanyl)-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound C=1C(C)=C(NC(=O)CC2C3CCC(C3)C2)C(C)=CC=1N1CCOCC1 GTZXKLYUHHQHSC-UHFFFAOYSA-N 0.000 claims description 2
• HJIGCVIPHPXEAG-UHFFFAOYSA-N 2-(3-bromophenyl)-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=CC(Br)=C1 HJIGCVIPHPXEAG-UHFFFAOYSA-N 0.000 claims description 2
• SUSVXXUDGGTLSU-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-(2-methoxy-6-methyl-4-morpholin-4-ylphenyl)acetamide Chemical compound COC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=CC(F)=C1 SUSVXXUDGGTLSU-UHFFFAOYSA-N 0.000 claims description 2
• TZAZWGAJSJSJCU-UHFFFAOYSA-N 2-cyclohexyl-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1CCCCC1 TZAZWGAJSJSJCU-UHFFFAOYSA-N 0.000 claims description 2
• NSJRMPWZUISROM-UHFFFAOYSA-N 2-cyclopent-2-en-1-yl-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1CCC=C1 NSJRMPWZUISROM-UHFFFAOYSA-N 0.000 claims description 2
• ZIRYOJPIWUDDFZ-UHFFFAOYSA-N 2-cyclopent-2-en-1-yl-n-(2-methoxy-6-methyl-4-morpholin-4-ylphenyl)acetamide Chemical compound COC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1CCC=C1 ZIRYOJPIWUDDFZ-UHFFFAOYSA-N 0.000 claims description 2
• JNWPEEJRMRBMPA-UHFFFAOYSA-N 2-cyclopentyl-n-(2-methoxy-6-methyl-4-morpholin-4-ylphenyl)acetamide Chemical compound COC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1CCCC1 JNWPEEJRMRBMPA-UHFFFAOYSA-N 0.000 claims description 2
• WAVXDFUOPQGUBX-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dimethyl-4-(2-phenylthiomorpholin-4-yl)phenyl]acetamide Chemical compound CC1=CC(N2CC(SCC2)C=2C=CC=CC=2)=CC(C)=C1NC(=O)CC1CCCC1 WAVXDFUOPQGUBX-UHFFFAOYSA-N 0.000 claims description 2
• ODMKRGYVCINZSZ-UHFFFAOYSA-N 2-cyclopentyl-n-[2-(3-methylphenyl)-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC=CC(C=2C(=C(C=C(C=2)N2CCOCC2)C(F)(F)F)NC(=O)CC2CCCC2)=C1 ODMKRGYVCINZSZ-UHFFFAOYSA-N 0.000 claims description 2
• ZEIHZBPMFYBKDA-UHFFFAOYSA-N 2-cyclopentyl-n-[2-(4-fluorophenyl)-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(F)=CC=C1C1=CC(N2CCOCC2)=CC(C(F)(F)F)=C1NC(=O)CC1CCCC1 ZEIHZBPMFYBKDA-UHFFFAOYSA-N 0.000 claims description 2
• PRRCZFLHDUNRPA-UHFFFAOYSA-N 2-cyclopentyl-n-[4-morpholin-4-yl-2-phenyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound C1CCCC1CC(=O)NC=1C(C(F)(F)F)=CC(N2CCOCC2)=CC=1C1=CC=CC=C1 PRRCZFLHDUNRPA-UHFFFAOYSA-N 0.000 claims description 2
• XBLDZJXJCQTOHW-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)propanamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CCC1=CC=CC(Cl)=C1 XBLDZJXJCQTOHW-UHFFFAOYSA-N 0.000 claims description 2
• 208000002877 Epileptic Syndromes Diseases 0.000 claims description 2
• 206010033664 Panic attack Diseases 0.000 claims description 2
• 206010052794 Panic disorder with agoraphobia Diseases 0.000 claims description 2
• 206010033668 Panic disorder without agoraphobia Diseases 0.000 claims description 2
• 208000031674 Traumatic Acute Stress disease Diseases 0.000 claims description 2
• 230000001154 acute effect Effects 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• 230000002631 hypothermal effect Effects 0.000 claims description 2
• 230000006742 locomotor activity Effects 0.000 claims description 2
• QFBRGGLYIZJDNP-UHFFFAOYSA-N n-(2,6-difluoro-4-morpholin-4-ylphenyl)-2-(3-fluorophenyl)acetamide Chemical compound FC1=CC=CC(CC(=O)NC=2C(=CC(=CC=2F)N2CCOCC2)F)=C1 QFBRGGLYIZJDNP-UHFFFAOYSA-N 0.000 claims description 2
• PCQHZOFRMZIDSO-UHFFFAOYSA-N n-(2,6-difluoro-4-morpholin-4-ylphenyl)-3,3-dimethylbutanamide Chemical compound C1=C(F)C(NC(=O)CC(C)(C)C)=C(F)C=C1N1CCOCC1 PCQHZOFRMZIDSO-UHFFFAOYSA-N 0.000 claims description 2
• RZHYJMWCLWAHFW-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-(3,4-dimethylphenyl)acetamide Chemical compound C1=C(C)C(C)=CC=C1CC(=O)NC1=C(C)C=C(N2CCOCC2)C=C1C RZHYJMWCLWAHFW-UHFFFAOYSA-N 0.000 claims description 2
• BWTFEOVRRVXFIS-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-(3-fluorophenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=CC(F)=C1 BWTFEOVRRVXFIS-UHFFFAOYSA-N 0.000 claims description 2
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