HRP20090685T1 - Supstituirani derivati morfolina i tiomorfolina - Google Patents
Supstituirani derivati morfolina i tiomorfolina Download PDFInfo
- Publication number
- HRP20090685T1 HRP20090685T1 HR20090685T HRP20090685T HRP20090685T1 HR P20090685 T1 HRP20090685 T1 HR P20090685T1 HR 20090685 T HR20090685 T HR 20090685T HR P20090685 T HRP20090685 T HR P20090685T HR P20090685 T1 HRP20090685 T1 HR P20090685T1
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- alk
- morpholin
- dimethyl
- cycloalk
- Prior art date
Links
- 150000002780 morpholines Chemical class 0.000 title claims abstract 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title claims abstract 3
- 150000004886 thiomorpholines Chemical class 0.000 title claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 9
- 150000002367 halogens Chemical class 0.000 claims abstract 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 7
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 6
- 125000001424 substituent group Chemical group 0.000 claims abstract 6
- 125000005843 halogen group Chemical group 0.000 claims abstract 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000003222 pyridines Chemical class 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 229930192474 thiophene Natural products 0.000 claims abstract 3
- 150000003577 thiophenes Chemical class 0.000 claims abstract 3
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000012458 free base Substances 0.000 claims abstract 2
- 150000002240 furans Chemical class 0.000 claims abstract 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000002475 indoles Chemical class 0.000 claims abstract 2
- 150000002916 oxazoles Chemical class 0.000 claims abstract 2
- 150000003230 pyrimidines Chemical class 0.000 claims abstract 2
- 150000003233 pyrroles Chemical class 0.000 claims abstract 2
- 150000003248 quinolines Chemical class 0.000 claims abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000003557 thiazoles Chemical class 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 208000019901 Anxiety disease Diseases 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 208000004296 neuralgia Diseases 0.000 claims 5
- 208000021722 neuropathic pain Diseases 0.000 claims 5
- 206010010904 Convulsion Diseases 0.000 claims 4
- 208000019695 Migraine disease Diseases 0.000 claims 3
- 206010027599 migraine Diseases 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- PKOCZEXVIUDRRW-UHFFFAOYSA-N (2,6-dimethyl-4-morpholin-4-ylphenyl)carbamic acid Chemical compound CC1=C(NC(O)=O)C(C)=CC(N2CCOCC2)=C1 PKOCZEXVIUDRRW-UHFFFAOYSA-N 0.000 claims 2
- 208000008811 Agoraphobia Diseases 0.000 claims 2
- 208000004454 Hyperalgesia Diseases 0.000 claims 2
- 206010033664 Panic attack Diseases 0.000 claims 2
- 206010034912 Phobia Diseases 0.000 claims 2
- 206010036105 Polyneuropathy Diseases 0.000 claims 2
- 208000027520 Somatoform disease Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000027753 pain disease Diseases 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 201000001716 specific phobia Diseases 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 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 1
- MBGBDCSGKYOPEA-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=CC=C1Cl MBGBDCSGKYOPEA-UHFFFAOYSA-N 0.000 claims 1
- HQFQNYRKJOYWEY-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=C(Cl)C(Cl)=C1 HQFQNYRKJOYWEY-UHFFFAOYSA-N 0.000 claims 1
- RDFIAPRCAVTVFL-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-n-(1,2-dimethyl-4-morpholin-4-ylcyclohexa-2,4-dien-1-yl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CCC1(C)NC(=O)CC1=CC=C(F)C(F)=C1 RDFIAPRCAVTVFL-UHFFFAOYSA-N 0.000 claims 1
- LJUSTXRGYUENLJ-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-n-(2-methoxy-6-methyl-4-morpholin-4-ylphenyl)acetamide Chemical compound COC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=C(F)C(F)=C1 LJUSTXRGYUENLJ-UHFFFAOYSA-N 0.000 claims 1
- YYIRIYBLIVBHTF-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-n-[2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C(F)(F)F)=C1NC(=O)CC1=CC=C(F)C(F)=C1 YYIRIYBLIVBHTF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NBHOSDYTOKFPRM-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=CC(Cl)=C1 NBHOSDYTOKFPRM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- PSPKOXMCPHZZFA-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-morpholin-4-yl-2-pyridin-3-yl-6-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC1=C(C=2C=NC=CC=2)C=C(N2CCOCC2)C=C1C(F)(F)F PSPKOXMCPHZZFA-UHFFFAOYSA-N 0.000 claims 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- YDSRFTJYQRXZCE-UHFFFAOYSA-N 3,3-dimethyl-n-[2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]butanamide Chemical compound FC(F)(F)C1=C(NC(=O)CC(C)(C)C)C(C)=CC(N2CCOCC2)=C1 YDSRFTJYQRXZCE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010001497 Agitation Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 241000589968 Borrelia Species 0.000 claims 1
- 208000014644 Brain disease Diseases 0.000 claims 1
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 206010013654 Drug abuse Diseases 0.000 claims 1
- 208000032274 Encephalopathy Diseases 0.000 claims 1
- 208000002877 Epileptic Syndromes Diseases 0.000 claims 1
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000035154 Hyperesthesia Diseases 0.000 claims 1
- 201000001916 Hypochondriasis Diseases 0.000 claims 1
- 208000016604 Lyme disease Diseases 0.000 claims 1
- XFPRMSCCOJUEBM-UHFFFAOYSA-N N-[1-methyl-4-morpholin-4-yl-2-(trifluoromethyl)cyclohexa-2,4-dien-1-yl]hexanamide Chemical compound CC1(CC=C(C=C1C(F)(F)F)N1CCOCC1)NC(CCCCC)=O XFPRMSCCOJUEBM-UHFFFAOYSA-N 0.000 claims 1
- 206010029240 Neuritis Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 206010052794 Panic disorder with agoraphobia Diseases 0.000 claims 1
- 206010033668 Panic disorder without agoraphobia Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000004983 Phantom Limb Diseases 0.000 claims 1
- 206010056238 Phantom pain Diseases 0.000 claims 1
- 102000004257 Potassium Channel Human genes 0.000 claims 1
- 241000710799 Rubella virus Species 0.000 claims 1
- 208000000810 Separation Anxiety Diseases 0.000 claims 1
- 206010041250 Social phobia Diseases 0.000 claims 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
- 231100000643 Substance intoxication Toxicity 0.000 claims 1
- 206010070863 Toxicity to various agents Diseases 0.000 claims 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 claims 1
- 206010048010 Withdrawal syndrome Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000012826 adjustment disease Diseases 0.000 claims 1
- 206010053552 allodynia Diseases 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 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 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 208000029364 generalized anxiety disease Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- LITBCMPJKSAOBQ-UHFFFAOYSA-N n-(1,2-dimethyl-4-morpholin-4-ylcyclohexa-2,4-dien-1-yl)-2-(3-methylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CCC1(C)NC(=O)CC1=CC=CC(C)=C1 LITBCMPJKSAOBQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- DBQFAOANWIBIGE-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-naphthalen-2-ylacetamide Chemical compound C=1C(C)=C(NC(=O)CC=2C=C3C=CC=CC3=CC=2)C(C)=CC=1N1CCOCC1 DBQFAOANWIBIGE-UHFFFAOYSA-N 0.000 claims 1
- IPQCETRADJWXPC-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-phenylacetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=CC=C1 IPQCETRADJWXPC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- QDYMTVOPTQMLIP-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-3-methylpentanamide Chemical compound C1=C(C)C(NC(=O)CC(C)CC)=C(C)C=C1N1CCOCC1 QDYMTVOPTQMLIP-UHFFFAOYSA-N 0.000 claims 1
- TVSPKPCWJNRGPB-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-4-methylpentanamide Chemical compound C1=C(C)C(NC(=O)CCC(C)C)=C(C)C=C1N1CCOCC1 TVSPKPCWJNRGPB-UHFFFAOYSA-N 0.000 claims 1
- FVUFQWDWZHWHQT-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-5-methylhexanamide Chemical compound C1=C(C)C(NC(=O)CCCC(C)C)=C(C)C=C1N1CCOCC1 FVUFQWDWZHWHQT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- FLNIDPUBPDBGTL-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)pentanamide Chemical compound C1=C(C)C(NC(=O)CCCC)=C(C)C=C1N1CCOCC1 FLNIDPUBPDBGTL-UHFFFAOYSA-N 0.000 claims 1
- CZXDPWCUNYIWRD-UHFFFAOYSA-N n-(2-chloro-6-methyl-4-morpholin-4-ylphenyl)-2-(3-fluorophenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(Cl)=C1NC(=O)CC1=CC=CC(F)=C1 CZXDPWCUNYIWRD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KIEKLHLDPVXZRI-UHFFFAOYSA-N n-(2-methoxy-6-methyl-4-morpholin-4-ylphenyl)-4-methylpentanamide Chemical compound CC1=C(NC(=O)CCC(C)C)C(OC)=CC(N2CCOCC2)=C1 KIEKLHLDPVXZRI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- JXVMTGLEBIWOHI-UHFFFAOYSA-N n-[2-bromo-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]-2-(3-fluorophenyl)acetamide Chemical compound FC1=CC=CC(CC(=O)NC=2C(=CC(=CC=2Br)N2CCOCC2)C(F)(F)F)=C1 JXVMTGLEBIWOHI-UHFFFAOYSA-N 0.000 claims 1
- RMGDROBIXZIMJN-UHFFFAOYSA-N n-[2-bromo-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]-2-(4-fluorophenyl)acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC1=C(Br)C=C(N2CCOCC2)C=C1C(F)(F)F RMGDROBIXZIMJN-UHFFFAOYSA-N 0.000 claims 1
- FPUGBBDCGLIOFN-UHFFFAOYSA-N n-[2-bromo-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]butanamide Chemical compound C1=C(C(F)(F)F)C(NC(=O)CCC)=C(Br)C=C1N1CCOCC1 FPUGBBDCGLIOFN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XSAPBUXDUGPCDB-UHFFFAOYSA-N n-[2-chloro-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]-2-(3-fluorophenyl)acetamide Chemical compound FC1=CC=CC(CC(=O)NC=2C(=CC(=CC=2Cl)N2CCOCC2)C(F)(F)F)=C1 XSAPBUXDUGPCDB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 244000052769 pathogen Species 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 208000019629 polyneuritis Diseases 0.000 claims 1
- 230000007824 polyneuropathy Effects 0.000 claims 1
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 1
- 108020001213 potassium channel Proteins 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 208000025874 separation anxiety disease Diseases 0.000 claims 1
- 208000005809 status epilepticus Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 206010044652 trigeminal neuralgia Diseases 0.000 claims 1
- 241001529453 unidentified herpesvirus Species 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
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- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
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UA89503C2 (uk) * | 2004-09-13 | 2010-02-10 | Х. Луннбек А/С | Заміщені похідні аніліну |
UA92340C2 (en) * | 2005-03-03 | 2010-10-25 | Х. Луннбек А/С | Substituted pyridine derivatives |
US7812020B2 (en) * | 2005-03-03 | 2010-10-12 | H. Lundbeck A/S | Substituted pyridine derivatives |
MX2008009655A (es) * | 2006-02-07 | 2008-09-03 | Lundbeck & Co As H | Metodo para tratar o reducir los sintomas de la esquizofrenia. |
US7960436B2 (en) | 2006-06-05 | 2011-06-14 | Valeant Pharmaceuticals International | Substituted arylamino-1,2,3,4-tetrahydro naphthalenes and-2,3-dihydro-1H-indenes as potassium channel modulators |
US8993593B2 (en) | 2006-08-23 | 2015-03-31 | Valeant Pharmaceuticals International | N-(4-(6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl)-2,6-dimethylphenyl)-3,3-dimethylbutanamide as potassium channel modulators |
AU2007288253B2 (en) | 2006-08-23 | 2013-05-02 | Xenon Pharmaceuticals Inc. | Derivatives of 4-(N-azacycloalkyl) anilides as potassium channel modulators |
KR20090083479A (ko) | 2006-11-28 | 2009-08-03 | 밸리언트 파마슈티컬즈 인터내셔널 | 칼륨 채널 조절제로서의 1,4 디아미노 이환 레티가빈 유사체 |
WO2008130616A2 (en) * | 2007-04-19 | 2008-10-30 | Schering Corporation | Diaryl morpholines as cb1 modulators |
US8367684B2 (en) | 2007-06-13 | 2013-02-05 | Valeant Pharmaceuticals International | Derivatives of 4-(N-azacycloalkyl) anilides as potassium channel modulators |
US20100256145A1 (en) * | 2007-08-01 | 2010-10-07 | H. Lundbeck A/S | Use of kcnq potassium channel openers for reducing symptoms of or treating disorders or conditions wherein the dopaminergic system is disrupted |
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 |
EP2116618A1 (en) | 2008-05-09 | 2009-11-11 | Agency for Science, Technology And Research | Diagnosis and treatment of Kawasaki disease |
WO2010094644A1 (en) * | 2009-02-17 | 2010-08-26 | Neurosearch A/S | Substituted pyridine derivatives and their medical use |
WO2010094645A1 (en) * | 2009-02-17 | 2010-08-26 | Neurosearch A/S | Substituted pyridine derivatives and their medical use |
TW201041857A (en) * | 2009-05-11 | 2010-12-01 | Lundbeck & Co As H | Stable forms of N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-3,3-dimethyl-butyramide |
US20100286138A1 (en) * | 2009-05-11 | 2010-11-11 | H. Lundbeck A/S | Stable forms of N-(2,6-Dimethyl-4-morpholin-4-yl-phenyl)-3,3-dimethyl-butyramide |
WO2011026891A1 (en) * | 2009-09-07 | 2011-03-10 | Neurosearch A/S | Substituted pyridine derivatives and their medical use |
AU2011275393B2 (en) | 2010-07-08 | 2014-04-10 | Pfizer Inc. | Piperidinyl pyrimidine amides as Kv7 potassium channel openers |
CN103073455B (zh) | 2011-10-25 | 2015-08-19 | 中国科学院上海药物研究所 | 一类新型的kcnq钾通道激动剂、其制备方法和用途 |
US9321750B2 (en) * | 2012-04-20 | 2016-04-26 | Innov17 Llc | ROR modulators and their uses |
CN103044431A (zh) * | 2012-10-22 | 2013-04-17 | 中国药科大学 | 制备五氟磺草胺的新方法 |
US8652527B1 (en) | 2013-03-13 | 2014-02-18 | Upsher-Smith Laboratories, Inc | Extended-release topiramate capsules |
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US20170360726A1 (en) * | 2014-12-05 | 2017-12-21 | Aquinnah Pharmaceuticals, Inc. | Compounds, compositions and methods of use |
EP3366683A1 (en) * | 2017-02-28 | 2018-08-29 | Acousia Therapeutics GmbH | Cyclic amides, acteamides and ureas useful as potassium channel openers |
WO2020157126A1 (en) | 2019-01-29 | 2020-08-06 | Università degli Studi di Salerno | Modulators of potassium ion channels and uses thereof |
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JPH03175086A (ja) * | 1989-09-14 | 1991-07-30 | Fuji Photo Film Co Ltd | ジアゾ感熱記録材料 |
DE4200259A1 (de) | 1992-01-08 | 1993-07-15 | Asta Medica Ag | Neue 1,2,4-triaminobenzol-derivate und verfahren zu deren herstellung |
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DE19539861A1 (de) | 1995-10-26 | 1997-04-30 | Asta Medica Ag | Verwendung von 4-Amino-4-(4-fluorbenzylamino)-1-ethoxy-carbonylaminobenzen zur Prophylaxe und Behandlung der Folgen der akuten und chronischen zerebralen Minderdurchblutung sowie neurodegenerativer Erkrankungen |
NZ329200A (en) * | 1996-12-16 | 1999-05-28 | Hoechst Ag | Sulphonamide substituted quinazoline, isoquinoline, quinoline or benzo[1,3-]oxazine derivatives and medicaments |
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JP2002509924A (ja) * | 1998-03-27 | 2002-04-02 | デュポン ファーマシューティカルズ カンパニー | 第Xa因子阻害剤としてのジ置換ピラゾリン類およびトリアゾリン類 |
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IL152202A0 (en) | 2000-05-26 | 2003-05-29 | Bristol Myers Squibb Co | Human kcnq5 polypeptide and pharmaceutical compositions containing the same |
WO2001096540A2 (en) | 2000-06-11 | 2001-12-20 | Dupont Pharmaceuticals Company | Hepatitis c protease exosite for inhibitor design |
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CN1250519C (zh) * | 2001-01-19 | 2006-04-12 | 中国人民解放军军事医学科学院毒物药物研究所 | 具有调节钾通道功能的胺衍生物及其制备方法和应用 |
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- 2005-03-09 AU AU2005221762A patent/AU2005221762B2/en not_active Ceased
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- 2005-03-09 ES ES05706819T patent/ES2306087T3/es active Active
- 2005-03-11 MY MYPI20051046A patent/MY143698A/en unknown
- 2005-03-11 MY MYPI20094719A patent/MY147786A/en unknown
- 2005-09-03 UA UAA200610517A patent/UA90670C2/uk unknown
- 2005-12-21 US US11/314,802 patent/US7501414B2/en active Active
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2006
- 2006-08-31 ZA ZA2006/07286A patent/ZA200607286B/en unknown
- 2006-09-03 IL IL177859A patent/IL177859A/en active IP Right Grant
- 2006-09-12 CO CO06091597A patent/CO5721001A2/es active IP Right Grant
- 2006-09-12 EG EGNA2006000856 patent/EG25344A/xx active
- 2006-10-10 NO NO20064599A patent/NO337161B1/no not_active IP Right Cessation
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2007
- 2007-11-12 ZA ZA200709718A patent/ZA200709718B/xx unknown
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2008
- 2008-09-10 CY CY20081100969T patent/CY1110392T1/el unknown
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2009
- 2009-01-28 US US12/361,404 patent/US20090143369A1/en not_active Abandoned
- 2009-01-28 US US12/361,509 patent/US7632835B2/en not_active Expired - Fee Related
- 2009-11-03 US US12/611,249 patent/US8012962B2/en not_active Expired - Fee Related
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- 2009-12-21 CY CY20091101325T patent/CY1109656T1/el unknown
- 2009-12-23 HR HR20090685T patent/HRP20090685T1/hr unknown
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2011
- 2011-07-28 US US13/192,833 patent/US8299075B2/en active Active
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2012
- 2012-12-27 HK HK12113443.2A patent/HK1172618A1/zh unknown
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