ZA200505357B - Substituted aniline derivatives - Google Patents
Substituted aniline derivatives Download PDFInfo
- Publication number
- ZA200505357B ZA200505357B ZA200505357A ZA200505357A ZA200505357B ZA 200505357 B ZA200505357 B ZA 200505357B ZA 200505357 A ZA200505357 A ZA 200505357A ZA 200505357 A ZA200505357 A ZA 200505357A ZA 200505357 B ZA200505357 B ZA 200505357B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- alk
- phenyl
- cycloalk
- ethyl ester
- Prior art date
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- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 226
- -1 {2-Amino-4-[ (3-trifluoromethylphenylamino)methyl]phenyl}carbamic acid Chemical compound 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 43
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 206010010904 Convulsion Diseases 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 208000019901 Anxiety disease Diseases 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 21
- 108020001213 potassium channel Proteins 0.000 claims description 20
- 102000004257 Potassium Channel Human genes 0.000 claims description 19
- 206010015037 epilepsy Diseases 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 208000004296 neuralgia Diseases 0.000 claims description 14
- 208000021722 neuropathic pain Diseases 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 230000005764 inhibitory process Effects 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 230000002265 prevention Effects 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 230000001537 neural effect Effects 0.000 claims description 10
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 10
- 208000019695 Migraine disease Diseases 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
- 206010027599 migraine Diseases 0.000 claims description 8
- 206010001497 Agitation Diseases 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 230000004770 neurodegeneration Effects 0.000 claims description 7
- 208000014644 Brain disease Diseases 0.000 claims description 6
- 208000032274 Encephalopathy Diseases 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 208000027520 Somatoform disease Diseases 0.000 claims description 5
- 150000001448 anilines Chemical class 0.000 claims description 5
- QHGZFCAIXRVHID-UHFFFAOYSA-N ethyl n-methyl-n-phenylcarbamate Chemical compound CCOC(=O)N(C)C1=CC=CC=C1 QHGZFCAIXRVHID-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 208000027753 pain disease Diseases 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 208000030507 AIDS Diseases 0.000 claims description 4
- 208000008811 Agoraphobia Diseases 0.000 claims description 4
- 241000589968 Borrelia Species 0.000 claims description 4
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims description 4
- 208000016604 Lyme disease Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 206010034912 Phobia Diseases 0.000 claims description 4
- 241000710799 Rubella virus Species 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 230000036461 convulsion Effects 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 230000035987 intoxication Effects 0.000 claims description 4
- 231100000566 intoxication Toxicity 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 244000052769 pathogen Species 0.000 claims description 4
- 201000001716 specific phobia Diseases 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- 241001529453 unidentified herpesvirus Species 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 3
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000004454 Hyperalgesia Diseases 0.000 claims description 3
- 201000001916 Hypochondriasis Diseases 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
- 208000004983 Phantom Limb Diseases 0.000 claims description 3
- 206010056238 Phantom pain Diseases 0.000 claims description 3
- 208000000810 Separation Anxiety Diseases 0.000 claims description 3
- 206010041250 Social phobia Diseases 0.000 claims description 3
- 208000012826 adjustment disease Diseases 0.000 claims description 3
- 206010053552 allodynia Diseases 0.000 claims description 3
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- PAUMPFSSOXRDEJ-UHFFFAOYSA-N ethyl n-[2-amino-4-(anilinomethyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC=C1 PAUMPFSSOXRDEJ-UHFFFAOYSA-N 0.000 claims description 3
- XVKFYUITXXYYEN-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2,4-difluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C=C1F XVKFYUITXXYYEN-UHFFFAOYSA-N 0.000 claims description 3
- VDDRKSVFMCGVKS-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC=C1F VDDRKSVFMCGVKS-UHFFFAOYSA-N 0.000 claims description 3
- RAVCWWJMYAMNLK-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(F)=C1 RAVCWWJMYAMNLK-UHFFFAOYSA-N 0.000 claims description 3
- PZWXBOANAHDGDV-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-butylanilino)methyl]phenyl]carbamate Chemical compound C1=CC(CCCC)=CC=C1NCC1=CC=C(NC(=O)OCC)C(N)=C1 PZWXBOANAHDGDV-UHFFFAOYSA-N 0.000 claims description 3
- DWSPCTCHYKCYFR-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-chloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 DWSPCTCHYKCYFR-UHFFFAOYSA-N 0.000 claims description 3
- LLYSQBCINNSNKO-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-cyclohexylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C2CCCCC2)C=C1 LLYSQBCINNSNKO-UHFFFAOYSA-N 0.000 claims description 3
- NQNXMCDBIPXRFF-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C=C1 NQNXMCDBIPXRFF-UHFFFAOYSA-N 0.000 claims description 3
- BSCJHOFVPMMXGC-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-methoxyanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(OC)C=C1 BSCJHOFVPMMXGC-UHFFFAOYSA-N 0.000 claims description 3
- NVOFZLPWTFWFDQ-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-phenylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C=2C=CC=CC=2)C=C1 NVOFZLPWTFWFDQ-UHFFFAOYSA-N 0.000 claims description 3
- OVMRYCWHBHWHDB-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-propan-2-ylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(C)C)C=C1 OVMRYCWHBHWHDB-UHFFFAOYSA-N 0.000 claims description 3
- YGDMFPQYDCZIMM-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-tert-butylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(C)(C)C)C=C1 YGDMFPQYDCZIMM-UHFFFAOYSA-N 0.000 claims description 3
- CBUCMNUGRUKIBK-UHFFFAOYSA-N ethyl n-[2-amino-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 CBUCMNUGRUKIBK-UHFFFAOYSA-N 0.000 claims description 3
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 3
- 230000000917 hyperalgesic effect Effects 0.000 claims description 3
- 230000002981 neuropathic effect Effects 0.000 claims description 3
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 208000025874 separation anxiety disease Diseases 0.000 claims description 3
- 208000005809 status epilepticus Diseases 0.000 claims description 3
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 208000026345 acute stress disease Diseases 0.000 claims description 2
- XFNGDUVFJSECBN-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2,3-dichloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(Cl)=C1Cl XFNGDUVFJSECBN-UHFFFAOYSA-N 0.000 claims description 2
- NPFOVUKAFGUSQL-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2,3-dihydro-1h-inden-5-ylamino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(CCC2)C2=C1 NPFOVUKAFGUSQL-UHFFFAOYSA-N 0.000 claims description 2
- MPNLUKUAXMXGGU-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2,4-dichloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1Cl MPNLUKUAXMXGGU-UHFFFAOYSA-N 0.000 claims description 2
- PJFKUBNCMZLCEL-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3,4-difluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C(F)=C1 PJFKUBNCMZLCEL-UHFFFAOYSA-N 0.000 claims description 2
- STCYUEYAARANPB-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-chloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(Cl)=C1 STCYUEYAARANPB-UHFFFAOYSA-N 0.000 claims description 2
- RNFBDOBYXLGUBY-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-methylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(C)=C1 RNFBDOBYXLGUBY-UHFFFAOYSA-N 0.000 claims description 2
- CIYWTQMAZIEXNG-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-methylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C)C=C1 CIYWTQMAZIEXNG-UHFFFAOYSA-N 0.000 claims description 2
- IMAVPOSIWIUFQB-UHFFFAOYSA-N ethyl n-[2-amino-4-[(naphthalen-2-ylamino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C=CC=C2)C2=C1 IMAVPOSIWIUFQB-UHFFFAOYSA-N 0.000 claims description 2
- SHWHGZSYKAZUIB-UHFFFAOYSA-N ethyl n-[2-amino-4-[1-(4-chloroanilino)ethyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1C(C)NC1=CC=C(Cl)C=C1 SHWHGZSYKAZUIB-UHFFFAOYSA-N 0.000 claims description 2
- HIDMNWJFCJAMQI-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(3-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(F)=C1 HIDMNWJFCJAMQI-UHFFFAOYSA-N 0.000 claims description 2
- URAKWDASUSFXKH-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(4-chloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 URAKWDASUSFXKH-UHFFFAOYSA-N 0.000 claims description 2
- XPAYAFCWAGCEME-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(4-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C=C1 XPAYAFCWAGCEME-UHFFFAOYSA-N 0.000 claims description 2
- YETJUQCNPAAANG-UHFFFAOYSA-N ethyl n-[2-methyl-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 YETJUQCNPAAANG-UHFFFAOYSA-N 0.000 claims description 2
- PSRTZGHRXNJOEO-UHFFFAOYSA-N ethyl n-[4-[(3,4-difluoroanilino)methyl]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C(F)=C1 PSRTZGHRXNJOEO-UHFFFAOYSA-N 0.000 claims description 2
- YFYLMPIYVCSHPH-UHFFFAOYSA-N ethyl n-[4-[(3-fluoroanilino)methyl]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(F)=C1 YFYLMPIYVCSHPH-UHFFFAOYSA-N 0.000 claims description 2
- RUVLMXALVIBXME-UHFFFAOYSA-N ethyl n-[4-[(4-chloroanilino)methyl]-2-fluorophenyl]carbamate Chemical compound C1=C(F)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 RUVLMXALVIBXME-UHFFFAOYSA-N 0.000 claims description 2
- DPIDNSCETUXASM-UHFFFAOYSA-N ethyl n-[4-[(4-chloroanilino)methyl]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 DPIDNSCETUXASM-UHFFFAOYSA-N 0.000 claims description 2
- JRMWXXMVCOHXCB-UHFFFAOYSA-N ethyl n-[4-[(4-chloroanilino)methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 JRMWXXMVCOHXCB-UHFFFAOYSA-N 0.000 claims description 2
- HCLUFHIOGAXFCC-UHFFFAOYSA-N ethyl n-[4-[(4-fluoroanilino)methyl]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C=C1 HCLUFHIOGAXFCC-UHFFFAOYSA-N 0.000 claims description 2
- UNHRXQWFNONDJR-UHFFFAOYSA-N ethyl n-[4-[1-(4-chloroanilino)ethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(C)NC1=CC=C(Cl)C=C1 UNHRXQWFNONDJR-UHFFFAOYSA-N 0.000 claims description 2
- GCFCPEZENZTFAY-UHFFFAOYSA-N ethyl n-[4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 GCFCPEZENZTFAY-UHFFFAOYSA-N 0.000 claims description 2
- SHXIJKYXFWJGDT-UHFFFAOYSA-N n-[2-chloro-4-[(4-chloroanilino)methyl]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C=C1 SHXIJKYXFWJGDT-UHFFFAOYSA-N 0.000 claims description 2
- SIONWVZOLMLQGG-UHFFFAOYSA-N n-[2-chloro-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 SIONWVZOLMLQGG-UHFFFAOYSA-N 0.000 claims description 2
- QOUWPCGZCSHNRK-UHFFFAOYSA-N n-[4-[(4-amino-2-methylanilino)methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CNC1=CC=C(N)C=C1C QOUWPCGZCSHNRK-UHFFFAOYSA-N 0.000 claims description 2
- ANCSKQQFJNCGFC-UHFFFAOYSA-N n-[4-[(4-chloro-3-fluoroanilino)methyl]-2-fluorophenyl]butanamide Chemical compound C1=C(F)C(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C(F)=C1 ANCSKQQFJNCGFC-UHFFFAOYSA-N 0.000 claims description 2
- XFZWRYINWCHARH-UHFFFAOYSA-N n-[4-[(4-chloroanilino)methyl]-2-methylphenyl]butanamide Chemical compound C1=C(C)C(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C=C1 XFZWRYINWCHARH-UHFFFAOYSA-N 0.000 claims description 2
- SESQTSCDOREBKJ-UHFFFAOYSA-N n-[4-[(4-chloroanilino)methyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C=C1 SESQTSCDOREBKJ-UHFFFAOYSA-N 0.000 claims description 2
- PFUWYMNNTQXYIU-UHFFFAOYSA-N n-[4-[[2-(imidazol-1-ylmethyl)anilino]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CNC1=CC=CC=C1CN1C=NC=C1 PFUWYMNNTQXYIU-UHFFFAOYSA-N 0.000 claims description 2
- AQIYYEYDCKZSCQ-UHFFFAOYSA-N n-[4-[[(2,4-diaminoquinazolin-6-yl)amino]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CNC1=CC=C(N=C(N)N=C2N)C2=C1 AQIYYEYDCKZSCQ-UHFFFAOYSA-N 0.000 claims 2
- VAUTZIXBXVUZQA-UHFFFAOYSA-N 2-[(4-acetamidophenyl)methylamino]-5-chloro-n-(5-chloropyridin-2-yl)benzamide Chemical compound C1=CC(NC(=O)C)=CC=C1CNC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=N1 VAUTZIXBXVUZQA-UHFFFAOYSA-N 0.000 claims 1
- LVDKVOBNMQQEAL-UHFFFAOYSA-N ethyl n-[2-(4-chlorophenyl)-4-[(3-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(C=2C=CC(Cl)=CC=2)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(F)=C1 LVDKVOBNMQQEAL-UHFFFAOYSA-N 0.000 claims 1
- JBASQAITBFAGGZ-UHFFFAOYSA-N ethyl n-[2-(4-chlorophenyl)-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(C=2C=CC(Cl)=CC=2)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 JBASQAITBFAGGZ-UHFFFAOYSA-N 0.000 claims 1
- AVLRKXVHQCYJLZ-UHFFFAOYSA-N ethyl n-[2-[4-(dimethylamino)phenyl]-4-[(3-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(C=2C=CC(=CC=2)N(C)C)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(F)=C1 AVLRKXVHQCYJLZ-UHFFFAOYSA-N 0.000 claims 1
- YCMRKXZMNUMKST-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3,4-dichloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C(Cl)=C1 YCMRKXZMNUMKST-UHFFFAOYSA-N 0.000 claims 1
- HFTMLRRJCMKHCO-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3,5-dichloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC(Cl)=CC(Cl)=C1 HFTMLRRJCMKHCO-UHFFFAOYSA-N 0.000 claims 1
- UACNDMSYYWUJNP-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-chloro-3-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C(F)=C1 UACNDMSYYWUJNP-UHFFFAOYSA-N 0.000 claims 1
- BYARLUNDODGUSF-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-cyanoanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C#N)C=C1 BYARLUNDODGUSF-UHFFFAOYSA-N 0.000 claims 1
- VRXUASWAYZPEHF-UHFFFAOYSA-N ethyl n-[2-amino-4-[1-[4-(trifluoromethyl)anilino]ethyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1C(C)NC1=CC=C(C(F)(F)F)C=C1 VRXUASWAYZPEHF-UHFFFAOYSA-N 0.000 claims 1
- PYVCGNWJTVIAMS-UHFFFAOYSA-N ethyl n-[2-amino-4-[[3-fluoro-4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C(F)=C1 PYVCGNWJTVIAMS-UHFFFAOYSA-N 0.000 claims 1
- PJQJLRQLLHQJMP-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(3,4-dichloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C(Cl)=C1 PJQJLRQLLHQJMP-UHFFFAOYSA-N 0.000 claims 1
- YHALLHHMBWALKL-UHFFFAOYSA-N ethyl n-[2-chloro-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 YHALLHHMBWALKL-UHFFFAOYSA-N 0.000 claims 1
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- 230000004807 localization Effects 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- JTNKTTCJVFXBEH-UHFFFAOYSA-N n-[4-[(3,4,5-trimethoxyanilino)methyl]phenyl]acetamide Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C=CC(NC(C)=O)=CC=2)=C1 JTNKTTCJVFXBEH-UHFFFAOYSA-N 0.000 description 1
- FCNULWHUEPGFAA-UHFFFAOYSA-N n-[4-[[4-(imidazol-1-ylmethyl)anilino]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CNC(C=C1)=CC=C1CN1C=NC=C1 FCNULWHUEPGFAA-UHFFFAOYSA-N 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 230000008555 neuronal activation Effects 0.000 description 1
- 230000003961 neuronal insult Effects 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
- 229960000649 oxyphenbutazone Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- VJKUPQSHOVKBCO-AHMKVGDJSA-N picrotoxin Chemical compound O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(=C)C)[C@@H]1C(=O)O2.O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(C)(O)C)[C@@H]1C(=O)O2 VJKUPQSHOVKBCO-AHMKVGDJSA-N 0.000 description 1
- 229960001233 pregabalin Drugs 0.000 description 1
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 210000001176 projection neuron Anatomy 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000036390 resting membrane potential Effects 0.000 description 1
- 230000018448 secretion by cell Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000031893 sensory processing Effects 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 1
- 229940084026 sodium valproate Drugs 0.000 description 1
- 210000003594 spinal ganglia Anatomy 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 1
- PBJUNZJWGZTSKL-MRXNPFEDSA-N tiagabine Chemical compound C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C PBJUNZJWGZTSKL-MRXNPFEDSA-N 0.000 description 1
- 229960001918 tiagabine Drugs 0.000 description 1
- 229960004394 topiramate Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 210000000427 trigeminal ganglion Anatomy 0.000 description 1
- 210000000836 trigeminal nuclei Anatomy 0.000 description 1
- 210000004496 type 1 vestibular hair cell Anatomy 0.000 description 1
- 210000001213 vestibule labyrinth Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229960002911 zonisamide Drugs 0.000 description 1
- UBQNRHZMVUUOMG-UHFFFAOYSA-N zonisamide Chemical compound C1=CC=C2C(CS(=O)(=O)N)=NOC2=C1 UBQNRHZMVUUOMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200300392 | 2003-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200505357B true ZA200505357B (en) | 2006-12-27 |
Family
ID=58707220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200505357A ZA200505357B (en) | 2003-03-14 | 2004-03-12 | Substituted aniline derivatives |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20060167087A1 (ko) |
| KR (1) | KR20050117563A (ko) |
| CN (1) | CN1759099A (ko) |
| AR (1) | AR043507A1 (ko) |
| CL (1) | CL2004000488A1 (ko) |
| EA (1) | EA200501299A1 (ko) |
| IS (1) | IS7924A (ko) |
| NO (1) | NO20054721L (ko) |
| NZ (1) | NZ541242A (ko) |
| SG (1) | SG171472A1 (ko) |
| UA (1) | UA81799C2 (ko) |
| ZA (1) | ZA200505357B (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7799832B2 (en) * | 2003-10-23 | 2010-09-21 | Valeant Pharmaceuticals North America | Combinations of retigabine and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains |
| US8722929B2 (en) * | 2006-10-10 | 2014-05-13 | Valeant Pharmaceuticals International | N-[2-amino-4-(phenylmethoxy)phenyl] amides and related compounds as potassium channel modulators |
| US8563566B2 (en) * | 2007-08-01 | 2013-10-22 | Valeant Pharmaceuticals International | Naphthyridine derivatives as potassium channel modulators |
| US7786146B2 (en) * | 2007-08-13 | 2010-08-31 | Valeant Pharmaceuticals International | Derivatives of 5-amino-4,6-disubstituted indole and 5-amino-4,6-disubstituted indoline as potassium channel modulators |
| JP2011525538A (ja) * | 2008-06-24 | 2011-09-22 | バレアント プハルマセウトイカルス インターナショナル | カリウムチャネルモジュレーターとして有用なベンジルオキシアニリド誘導体 |
| US20130108687A1 (en) | 2010-05-21 | 2013-05-02 | Universitat Fur Bodenkultur Wien | Compositions for use in treating or diagnosing bone disorders and/or cardiovascular disorders |
| US20130210883A1 (en) | 2010-05-21 | 2013-08-15 | Johannes Grillari | Lipase inhibitors |
| WO2014114649A1 (en) * | 2013-01-22 | 2014-07-31 | Technische Universität Graz | Lipase inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3903989A1 (de) * | 1989-02-10 | 1990-09-20 | Basf Ag | Diphenylheteroalkylderivate, ihre herstellung und daraus hergestellte arzneimittel und kosmetika |
| CA2076012A1 (en) * | 1990-02-14 | 1991-08-15 | Yasuyuki Kato | Agent for inhibiting the formation of denatured ldl |
| US6472165B1 (en) * | 1999-08-03 | 2002-10-29 | Arzneimittelwerk Dresden Gmbh | Modulatory binding site in potassium channels for screening and finding new active ingredients |
| EP1369420A1 (en) * | 2002-06-06 | 2003-12-10 | Aventis Pharma Deutschland GmbH | Inhibitors of the GPib - vWF interaction |
-
2004
- 2004-03-08 AR ARP040100733A patent/AR043507A1/es not_active Application Discontinuation
- 2004-03-10 CL CL200400488A patent/CL2004000488A1/es unknown
- 2004-03-12 SG SG200718941-8A patent/SG171472A1/en unknown
- 2004-03-12 NZ NZ541242A patent/NZ541242A/en unknown
- 2004-03-12 ZA ZA200505357A patent/ZA200505357B/en unknown
- 2004-03-12 CN CNA2004800067754A patent/CN1759099A/zh active Pending
- 2004-03-12 KR KR1020057017223A patent/KR20050117563A/ko not_active Application Discontinuation
- 2004-03-12 EA EA200501299A patent/EA200501299A1/ru unknown
- 2004-03-12 US US10/549,345 patent/US20060167087A1/en not_active Abandoned
- 2004-12-03 UA UAA200508717A patent/UA81799C2/uk unknown
-
2005
- 2005-06-30 IS IS7924A patent/IS7924A/is unknown
- 2005-10-13 NO NO20054721A patent/NO20054721L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR043507A1 (es) | 2005-08-03 |
| CN1759099A (zh) | 2006-04-12 |
| CL2004000488A1 (es) | 2005-01-07 |
| IS7924A (is) | 2005-06-30 |
| EA200501299A1 (ru) | 2006-02-24 |
| NZ541242A (en) | 2009-01-31 |
| SG171472A1 (en) | 2011-06-29 |
| NO20054721L (no) | 2005-10-13 |
| US20060167087A1 (en) | 2006-07-27 |
| KR20050117563A (ko) | 2005-12-14 |
| UA81799C2 (uk) | 2008-02-11 |
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