NZ569517A - Use of KCNQ-openers for threating or reducing the symptoms of schizophrenia - Google Patents
Use of KCNQ-openers for threating or reducing the symptoms of schizophreniaInfo
- Publication number
- NZ569517A NZ569517A NZ569517A NZ56951707A NZ569517A NZ 569517 A NZ569517 A NZ 569517A NZ 569517 A NZ569517 A NZ 569517A NZ 56951707 A NZ56951707 A NZ 56951707A NZ 569517 A NZ569517 A NZ 569517A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alk
- cycloalk
- halo
- phenyl
- group
- Prior art date
Links
- 201000000980 schizophrenia Diseases 0.000 title claims abstract description 68
- 208000024891 symptom Diseases 0.000 title claims abstract description 61
- 150000001875 compounds Chemical class 0.000 claims abstract description 180
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 239000003814 drug Substances 0.000 claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- -1 cyano, amino Chemical group 0.000 claims description 150
- 239000001257 hydrogen Substances 0.000 claims description 123
- 229910052739 hydrogen Inorganic materials 0.000 claims description 123
- 125000004432 carbon atom Chemical group C* 0.000 claims description 104
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 97
- 125000005842 heteroatom Chemical group 0.000 claims description 93
- 229910052736 halogen Inorganic materials 0.000 claims description 78
- 229910052757 nitrogen Inorganic materials 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 125000002252 acyl group Chemical group 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 64
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 57
- 229910052760 oxygen Inorganic materials 0.000 claims description 57
- 229910052717 sulfur Inorganic materials 0.000 claims description 56
- 150000002367 halogens Chemical class 0.000 claims description 50
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 48
- 229920006395 saturated elastomer Polymers 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 238000011282 treatment Methods 0.000 claims description 26
- PCOBBVZJEWWZFR-UHFFFAOYSA-N ezogabine Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(F)C=C1 PCOBBVZJEWWZFR-UHFFFAOYSA-N 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 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 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 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 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 230000002829 reductive effect Effects 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 208000009668 Neurobehavioral Manifestations Diseases 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 108020001213 potassium channel Proteins 0.000 claims description 9
- 102000004257 Potassium Channel Human genes 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- BKFDFCVASNKPOA-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=CC(N2CCOCC2)=N1 BKFDFCVASNKPOA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- 206010007776 catatonia Diseases 0.000 claims description 3
- SCOOTUMXCXKEAD-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2,4,6-trimethylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=C(C)C=C(C)C=C1C SCOOTUMXCXKEAD-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
- 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
- IMOFGKWQMCCNKF-UHFFFAOYSA-N 2-cyclopentyl-n-(4,6-dimethyl-2-morpholin-4-ylpyrimidin-5-yl)acetamide Chemical compound CC1=NC(N2CCOCC2)=NC(C)=C1NC(=O)CC1CCCC1 IMOFGKWQMCCNKF-UHFFFAOYSA-N 0.000 claims description 2
- DKKUESYXEUWVTR-UHFFFAOYSA-N n-(4,6-dimethyl-2-morpholin-4-ylpyrimidin-5-yl)-2-(4-fluorophenyl)acetamide Chemical compound CC1=NC(N2CCOCC2)=NC(C)=C1NC(=O)CC1=CC=C(F)C=C1 DKKUESYXEUWVTR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 58
- 125000005843 halogen group Chemical group 0.000 description 50
- 238000000034 method Methods 0.000 description 50
- 230000000694 effects Effects 0.000 description 43
- 238000012360 testing method Methods 0.000 description 42
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 37
- 229940025084 amphetamine Drugs 0.000 description 34
- 230000014509 gene expression Effects 0.000 description 33
- 125000002950 monocyclic group Chemical group 0.000 description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 33
- 241000700159 Rattus Species 0.000 description 32
- 230000000561 anti-psychotic effect Effects 0.000 description 29
- 229960003638 dopamine Drugs 0.000 description 29
- 230000004044 response Effects 0.000 description 28
- 241001465754 Metazoa Species 0.000 description 23
- 125000004429 atom Chemical group 0.000 description 23
- 230000005764 inhibitory process Effects 0.000 description 22
- 125000002619 bicyclic group Chemical group 0.000 description 21
- 241000699670 Mus sp. Species 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 18
- 102000012359 KCNQ Potassium Channels Human genes 0.000 description 18
- 108010022282 KCNQ Potassium Channels Proteins 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 18
- 239000003981 vehicle Substances 0.000 description 18
- 208000020925 Bipolar disease Diseases 0.000 description 17
- 239000000164 antipsychotic agent Substances 0.000 description 17
- 230000006399 behavior Effects 0.000 description 17
- 230000004899 motility Effects 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 16
- 238000010304 firing Methods 0.000 description 16
- 238000001727 in vivo Methods 0.000 description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 15
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 15
- 108091006146 Channels Proteins 0.000 description 14
- 229940005529 antipsychotics Drugs 0.000 description 14
- 208000013403 hyperactivity Diseases 0.000 description 14
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 13
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 13
- 150000002500 ions Chemical class 0.000 description 13
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 101150052147 ALLC gene Proteins 0.000 description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
- 208000028017 Psychotic disease Diseases 0.000 description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 12
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 12
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 210000004515 ventral tegmental area Anatomy 0.000 description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 11
- 206010026749 Mania Diseases 0.000 description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 11
- 230000003542 behavioural effect Effects 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000007920 subcutaneous administration Methods 0.000 description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 230000001154 acute effect Effects 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 210000001009 nucleus accumben Anatomy 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 230000002269 spontaneous effect Effects 0.000 description 10
- 108010006746 KCNQ2 Potassium Channel Proteins 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229960005017 olanzapine Drugs 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 9
- 229940080818 propionamide Drugs 0.000 description 9
- 229960003312 retigabine Drugs 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000003561 anti-manic effect Effects 0.000 description 8
- 210000004556 brain Anatomy 0.000 description 8
- 125000001246 bromo group Chemical group Br* 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 230000001143 conditioned effect Effects 0.000 description 8
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 238000012048 forced swim test Methods 0.000 description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 125000002346 iodo group Chemical group I* 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 230000006742 locomotor activity Effects 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 230000001537 neural effect Effects 0.000 description 7
- 210000002569 neuron Anatomy 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 7
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 101000994648 Homo sapiens Potassium voltage-gated channel subfamily KQT member 4 Proteins 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 239000000935 antidepressant agent Substances 0.000 description 6
- 229940005513 antidepressants Drugs 0.000 description 6
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 6
- 229960000632 dexamfetamine Drugs 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 210000005064 dopaminergic neuron Anatomy 0.000 description 6
- 230000003291 dopaminomimetic effect Effects 0.000 description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 208000024714 major depressive disease Diseases 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 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 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 description 5
- JDEUUKYNTHHAQH-UHFFFAOYSA-N 2,2-dimethylbutanamide Chemical compound CCC(C)(C)C(N)=O JDEUUKYNTHHAQH-UHFFFAOYSA-N 0.000 description 5
- 208000007415 Anhedonia Diseases 0.000 description 5
- 102000004980 Dopamine D2 Receptors Human genes 0.000 description 5
- 108090001111 Dopamine D2 Receptors Proteins 0.000 description 5
- 102100034354 Potassium voltage-gated channel subfamily KQT member 2 Human genes 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 230000001430 anti-depressive effect Effects 0.000 description 5
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 206010015037 epilepsy Diseases 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 230000035479 physiological effects, processes and functions Effects 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 238000012216 screening Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 235000020679 tap water Nutrition 0.000 description 5
- 239000008399 tap water Substances 0.000 description 5
- 150000003536 tetrazoles Chemical class 0.000 description 5
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 4
- 206010010904 Convulsion Diseases 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 108010038888 KCNQ3 Potassium Channel Proteins 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- 206010070834 Sensitisation Diseases 0.000 description 4
- 230000036982 action potential Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 4
- 208000028683 bipolar I disease Diseases 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 4
- 208000037765 diseases and disorders Diseases 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000002240 furans Chemical class 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- 150000003230 pyrimidines Chemical class 0.000 description 4
- 230000000698 schizophrenic effect Effects 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 150000003557 thiazoles Chemical class 0.000 description 4
- 150000003577 thiophenes Chemical class 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 3
- LINZZISWCNKFEM-UHFFFAOYSA-N 3,3-dimethylbutanamide Chemical compound CC(C)(C)CC(N)=O LINZZISWCNKFEM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010001497 Agitation Diseases 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 101150049660 DRD2 gene Proteins 0.000 description 3
- 206010011878 Deafness Diseases 0.000 description 3
- 206010012239 Delusion Diseases 0.000 description 3
- 208000020401 Depressive disease Diseases 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 208000004547 Hallucinations Diseases 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 102100034360 Potassium voltage-gated channel subfamily KQT member 3 Human genes 0.000 description 3
- 102100034363 Potassium voltage-gated channel subfamily KQT member 4 Human genes 0.000 description 3
- 102000003946 Prolactin Human genes 0.000 description 3
- 108010057464 Prolactin Proteins 0.000 description 3
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- 241000283984 Rodentia Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003639 Student–Newman–Keuls (SNK) method Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 229960003965 antiepileptics Drugs 0.000 description 3
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 208000025307 bipolar depression Diseases 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 3
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 3
- 231100000895 deafness Toxicity 0.000 description 3
- 231100000868 delusion Toxicity 0.000 description 3
- 238000001647 drug administration Methods 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 230000000857 drug effect Effects 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 208000016354 hearing loss disease Diseases 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 238000007918 intramuscular administration Methods 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000010534 mechanism of action Effects 0.000 description 3
- 238000001690 micro-dialysis Methods 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 230000036651 mood Effects 0.000 description 3
- 230000035772 mutation Effects 0.000 description 3
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 150000002916 oxazoles Chemical class 0.000 description 3
- 230000008092 positive effect Effects 0.000 description 3
- 238000010149 post-hoc-test Methods 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229940097325 prolactin Drugs 0.000 description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000007619 statistical method Methods 0.000 description 3
- 230000002459 sustained effect Effects 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- 231100001274 therapeutic index Toxicity 0.000 description 3
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 3
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
- MHPUGCYGQWGLJL-UHFFFAOYSA-N 5-methyl-hexanoic acid Chemical compound CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 101000994656 Homo sapiens Potassium voltage-gated channel subfamily KQT member 5 Proteins 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 238000011785 NMRI mouse Methods 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 102100034365 Potassium voltage-gated channel subfamily KQT member 5 Human genes 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 208000008409 Romano-Ward Syndrome Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- PYHRZPFZZDCOPH-UHFFFAOYSA-N amphetamine sulfate Chemical compound OS(O)(=O)=O.CC(N)CC1=CC=CC=C1.CC(N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-UHFFFAOYSA-N 0.000 description 2
- 238000000540 analysis of variance Methods 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 201000007201 aphasia Diseases 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 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 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- VEZNCHDBSQWUHQ-UHFFFAOYSA-N chlorocyclopropane Chemical compound ClC1CC1 VEZNCHDBSQWUHQ-UHFFFAOYSA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000001955 cumulated effect Effects 0.000 description 2
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 239000000385 dialysis solution Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000000835 electrochemical detection Methods 0.000 description 2
- 230000002996 emotional effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000000763 evoking effect Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 125000001207 fluorophenyl group Chemical group 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000004153 glucose metabolism Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229960003878 haloperidol Drugs 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- XZZXIYZZBJDEEP-UHFFFAOYSA-N imipramine hydrochloride Chemical compound [Cl-].C1CC2=CC=CC=C2N(CCC[NH+](C)C)C2=CC=CC=C21 XZZXIYZZBJDEEP-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 238000007913 intrathecal administration Methods 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 230000037356 lipid metabolism Effects 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 230000003137 locomotive effect Effects 0.000 description 2
- 201000006908 long QT syndrome 1 Diseases 0.000 description 2
- 238000011866 long-term treatment Methods 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical group COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 2
- WEIMMECSAQVSGO-UHFFFAOYSA-N n-(3-hydroxy-4-propylphenyl)acetamide Chemical compound CCCC1=CC=C(NC(C)=O)C=C1O WEIMMECSAQVSGO-UHFFFAOYSA-N 0.000 description 2
- PCHKLVYYPQCHED-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2-(4-chlorophenyl)acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(Cl)=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 PCHKLVYYPQCHED-UHFFFAOYSA-N 0.000 description 2
- 230000008587 neuronal excitability Effects 0.000 description 2
- 238000001543 one-way ANOVA Methods 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000004036 potassium channel stimulating agent Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000003368 psychostimulant agent Substances 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- 229960004431 quetiapine Drugs 0.000 description 2
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 2
- 229960001534 risperidone Drugs 0.000 description 2
- 229940085605 saccharin sodium Drugs 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 210000000225 synapse Anatomy 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000012549 training Methods 0.000 description 2
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- WFPIAZLQTJBIFN-DVZOWYKESA-N zuclopenthixol Chemical compound C1CN(CCO)CCN1CC\C=C\1C2=CC(Cl)=CC=C2SC2=CC=CC=C2/1 WFPIAZLQTJBIFN-DVZOWYKESA-N 0.000 description 2
- FHZUOZWUOXJEHV-UHFFFAOYSA-N (2-chlorophenyl)methyl n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)carbamate Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)OCC1=CC=CC=C1Cl FHZUOZWUOXJEHV-UHFFFAOYSA-N 0.000 description 1
- RIWKCXYUIMTQHW-UHFFFAOYSA-N (2-chlorophenyl)methyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCC=2C(=CC=CC=2)Cl)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 RIWKCXYUIMTQHW-UHFFFAOYSA-N 0.000 description 1
- OOMFPKMRUNSGGI-LJQANCHMSA-N (2r)-2-amino-n-[2,6-dimethyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]-4-methylpentanamide Chemical compound C1=C(C)C(NC(=O)[C@H](N)CC(C)C)=C(C)C=C1NCC1=CC=C(C(F)(F)F)C=C1 OOMFPKMRUNSGGI-LJQANCHMSA-N 0.000 description 1
- PIQCXJAFLBNPHH-UHFFFAOYSA-N (4-nitrophenyl)methyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCC=2C=CC(=CC=2)[N+]([O-])=O)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 PIQCXJAFLBNPHH-UHFFFAOYSA-N 0.000 description 1
- VSWBSWWIRNCQIJ-GJZGRUSLSA-N (R,R)-asenapine Chemical compound O1C2=CC=CC=C2[C@@H]2CN(C)C[C@H]2C2=CC(Cl)=CC=C21 VSWBSWWIRNCQIJ-GJZGRUSLSA-N 0.000 description 1
- WSPOMRSOLSGNFJ-AUWJEWJLSA-N (Z)-chlorprothixene Chemical compound C1=C(Cl)C=C2C(=C/CCN(C)C)\C3=CC=CC=C3SC2=C1 WSPOMRSOLSGNFJ-AUWJEWJLSA-N 0.000 description 1
- XYGVIBXOJOOCFR-BTJKTKAUSA-N (z)-but-2-enedioic acid;8-chloro-6-(2-fluorophenyl)-1-methyl-4h-imidazo[1,5-a][1,4]benzodiazepine Chemical compound OC(=O)\C=C/C(O)=O.C12=CC(Cl)=CC=C2N2C(C)=NC=C2CN=C1C1=CC=CC=C1F XYGVIBXOJOOCFR-BTJKTKAUSA-N 0.000 description 1
- PXUIZULXJVRBPC-UHFFFAOYSA-N 1'-[3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl]hexahydro-2H-spiro[imidazo[1,2-a]pyridine-3,4'-piperidin]-2-one Chemical compound C12=CC(Cl)=CC=C2CCC2=CC=CC=C2N1CCCN1CCC2(C(NC3CCCCN32)=O)CC1 PXUIZULXJVRBPC-UHFFFAOYSA-N 0.000 description 1
- DKMFBWQBDIGMHM-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(4-methyl-1-piperidinyl)-1-butanone Chemical compound C1CC(C)CCN1CCCC(=O)C1=CC=C(F)C=C1 DKMFBWQBDIGMHM-UHFFFAOYSA-N 0.000 description 1
- UGBLISDIHDMHJX-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[4-(2-methoxyphenyl)piperazin-1-yl]butan-1-one;hydrochloride Chemical compound [Cl-].COC1=CC=CC=C1N1CC[NH+](CCCC(=O)C=2C=CC(F)=CC=2)CC1 UGBLISDIHDMHJX-UHFFFAOYSA-N 0.000 description 1
- ZAYJLLOZEKWCBU-UHFFFAOYSA-N 1-[1-[(5-chlorothiophen-2-yl)methyl]-2,3-dihydroindol-5-yl]-3-ethylurea Chemical compound C1CC2=CC(NC(=O)NCC)=CC=C2N1CC1=CC=C(Cl)S1 ZAYJLLOZEKWCBU-UHFFFAOYSA-N 0.000 description 1
- GCGSQXNLMVWOOM-UHFFFAOYSA-N 1-[1-[(5-chlorothiophen-2-yl)methyl]-2,3-dihydroindol-5-yl]-3-thiophen-2-ylurea Chemical compound S1C(Cl)=CC=C1CN1C2=CC=C(NC(=O)NC=3SC=CC=3)C=C2CC1 GCGSQXNLMVWOOM-UHFFFAOYSA-N 0.000 description 1
- MDLAAYDRRZXJIF-UHFFFAOYSA-N 1-[4,4-bis(4-fluorophenyl)butyl]-4-[4-chloro-3-(trifluoromethyl)phenyl]-4-piperidinol Chemical compound C1CC(O)(C=2C=C(C(Cl)=CC=2)C(F)(F)F)CCN1CCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 MDLAAYDRRZXJIF-UHFFFAOYSA-N 0.000 description 1
- YNNPZLJSEXYKHU-UHFFFAOYSA-N 1-amino-n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=C(NC(=O)C2(N)CC2)C(C)=CC=1NCC1=CC=C(C(F)(F)F)C=C1 YNNPZLJSEXYKHU-UHFFFAOYSA-N 0.000 description 1
- LLIJZRLDYOMJMP-UHFFFAOYSA-N 1-benzyl-3-[1-[(5-chlorothiophen-2-yl)methyl]-2,3-dihydroindol-5-yl]urea Chemical compound S1C(Cl)=CC=C1CN1C2=CC=C(NC(=O)NCC=3C=CC=CC=3)C=C2CC1 LLIJZRLDYOMJMP-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- NHUKLKFWYRPWKW-UHFFFAOYSA-N 2,2,2-trichloro-n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]acetamide Chemical compound C=1C=C(NC(=O)C(Cl)(Cl)Cl)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 NHUKLKFWYRPWKW-UHFFFAOYSA-N 0.000 description 1
- GLHVEYVVFXLYTL-UHFFFAOYSA-N 2,2-dimethyl-n-[2-methyl-4-[(6-phenoxypyridin-3-yl)methylamino]phenyl]propanamide Chemical compound C1=C(NC(=O)C(C)(C)C)C(C)=CC(NCC=2C=NC(OC=3C=CC=CC=3)=CC=2)=C1 GLHVEYVVFXLYTL-UHFFFAOYSA-N 0.000 description 1
- MYGXIGJESMGAQN-UHFFFAOYSA-N 2,2-dimethylpropyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCC(C)(C)C)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 MYGXIGJESMGAQN-UHFFFAOYSA-N 0.000 description 1
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
- YXYOLVAXVPOIMA-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2OCCC2=C1 YXYOLVAXVPOIMA-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 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 description 1
- 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 description 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 description 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 description 1
- 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 description 1
- NUSLMFYDIBZGMM-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanyl)-n-[2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]acetamide Chemical compound C=1C(C(F)(F)F)=C(NC(=O)CC2C3CCC(C3)C2)C(C)=CC=1N1CCOCC1 NUSLMFYDIBZGMM-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
- AFRIITXJFGWUIR-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(Cl)=CC=2)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 AFRIITXJFGWUIR-UHFFFAOYSA-N 0.000 description 1
- BVVODLBVDQPGLE-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-(2-methoxyphenyl)-4,6-dimethylphenyl]acetamide Chemical compound COC1=CC=CC=C1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 BVVODLBVDQPGLE-UHFFFAOYSA-N 0.000 description 1
- NZPNIYSWXIODAQ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-(3-hydroxyphenyl)-4,6-dimethylphenyl]acetamide Chemical compound C=1C=CC(O)=CC=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 NZPNIYSWXIODAQ-UHFFFAOYSA-N 0.000 description 1
- SWBMVGKDTGXPPJ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-(4-hydroxy-3-methoxyphenyl)-4,6-dimethylphenyl]acetamide Chemical compound C1=C(O)C(OC)=CC(C=2C(=C(C)C=C(C)C=2)NC(=O)CC=2C=CC(F)=CC=2)=C1 SWBMVGKDTGXPPJ-UHFFFAOYSA-N 0.000 description 1
- PRGUIBZYEJEARJ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-methyl-4-[(4-methyl-2-phenylpyrimidin-5-yl)methylamino]phenyl]acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(C)=CC=1NCC(C(=N1)C)=CN=C1C1=CC=CC=C1 PRGUIBZYEJEARJ-UHFFFAOYSA-N 0.000 description 1
- UYMDMWMYTNGODR-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-methyl-4-[[6-(4-methylphenoxy)pyridin-3-yl]methylamino]phenyl]acetamide Chemical compound C1=CC(C)=CC=C1OC(N=C1)=CC=C1CNC(C=C1C)=CC=C1NC(=O)CC1=CC=C(F)C=C1 UYMDMWMYTNGODR-UHFFFAOYSA-N 0.000 description 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 description 1
- CSEQTDRDZQLHLC-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[6-nitro-1-[[4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]acetamide Chemical compound C1CC=2C=C(NC(=O)CC=3C=CC(F)=CC=3)C([N+](=O)[O-])=CC=2N1CC1=CC=C(C(F)(F)F)C=C1 CSEQTDRDZQLHLC-UHFFFAOYSA-N 0.000 description 1
- BABFYCSPNDKXRI-UHFFFAOYSA-N 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethyl 4-aminobutanoate Chemical compound C1CN(CCOC(=O)CCCN)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 BABFYCSPNDKXRI-UHFFFAOYSA-N 0.000 description 1
- HBAVDOFSYDZLMI-UHFFFAOYSA-N 2-amino-4-methyl-n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]pentanamide Chemical compound C1=C(C)C(NC(=O)C(N)CC(C)C)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 HBAVDOFSYDZLMI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CYKNZBUPYWRARU-UHFFFAOYSA-N 2-cyclohexylpropanamide Chemical compound NC(=O)C(C)C1CCCCC1 CYKNZBUPYWRARU-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ULKJRSJOIDFZPK-UHFFFAOYSA-N 2-cyclopentyl-n-(2,4-dimethyl-6-phenylphenyl)acetamide Chemical compound C=1C=CC=CC=1C1=CC(C)=CC(C)=C1NC(=O)CC1CCCC1 ULKJRSJOIDFZPK-UHFFFAOYSA-N 0.000 description 1
- RUAANJRZGQTEQK-UHFFFAOYSA-N 2-cyclopentyl-n-(2,6-diethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CCC1=CC(N2CCOCC2)=CC(CC)=C1NC(=O)CC1CCCC1 RUAANJRZGQTEQK-UHFFFAOYSA-N 0.000 description 1
- DUSXFTDHIFENLP-UHFFFAOYSA-N 2-cyclopentyl-n-(2,6-dimethyl-4-pyrrol-1-ylphenyl)acetamide Chemical compound CC1=CC(N2C=CC=C2)=CC(C)=C1NC(=O)CC1CCCC1 DUSXFTDHIFENLP-UHFFFAOYSA-N 0.000 description 1
- NDPLBCRXHOVZML-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dichloro-4-[(4-fluoroanilino)methyl]phenyl]acetamide Chemical compound C1=CC(F)=CC=C1NCC(C=C1Cl)=CC(Cl)=C1NC(=O)CC1CCCC1 NDPLBCRXHOVZML-UHFFFAOYSA-N 0.000 description 1
- AXEGVKSLGNHUDL-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dichloro-4-[[[5-(trifluoromethyl)pyridin-2-yl]amino]methyl]phenyl]acetamide Chemical compound N1=CC(C(F)(F)F)=CC=C1NCC(C=C1Cl)=CC(Cl)=C1NC(=O)CC1CCCC1 AXEGVKSLGNHUDL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- WRDIBHFRJFDWAW-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dimethyl-4-[(4-methylanilino)methyl]phenyl]acetamide Chemical compound C1=CC(C)=CC=C1NCC(C=C1C)=CC(C)=C1NC(=O)CC1CCCC1 WRDIBHFRJFDWAW-UHFFFAOYSA-N 0.000 description 1
- OYVKDFWBJVLPQJ-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dimethyl-4-[2-[4-(trifluoromethyl)phenyl]morpholin-4-yl]phenyl]acetamide Chemical compound CC1=CC(N2CC(OCC2)C=2C=CC(=CC=2)C(F)(F)F)=CC(C)=C1NC(=O)CC1CCCC1 OYVKDFWBJVLPQJ-UHFFFAOYSA-N 0.000 description 1
- PMAATXNYIJEXNJ-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dimethyl-4-[2-[4-(trifluoromethyl)phenyl]pyrrolidin-1-yl]phenyl]acetamide Chemical compound CC1=CC(N2C(CCC2)C=2C=CC(=CC=2)C(F)(F)F)=CC(C)=C1NC(=O)CC1CCCC1 PMAATXNYIJEXNJ-UHFFFAOYSA-N 0.000 description 1
- BHVKYMSGYOOSCM-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dimethyl-4-[[3-(trifluoromethyl)anilino]methyl]phenyl]acetamide Chemical compound C=1C(C)=C(NC(=O)CC2CCCC2)C(C)=CC=1CNC1=CC=CC(C(F)(F)F)=C1 BHVKYMSGYOOSCM-UHFFFAOYSA-N 0.000 description 1
- CUDFPNFQWMAENQ-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dimethyl-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]acetamide Chemical compound C=1C(C)=C(NC(=O)CC2CCCC2)C(C)=CC=1CNC1=CC=C(C(F)(F)F)C=C1 CUDFPNFQWMAENQ-UHFFFAOYSA-N 0.000 description 1
- RSXOPFCHOGTEKQ-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dimethyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]acetamide Chemical compound C=1C(C)=C(NC(=O)CC2CCCC2)C(C)=CC=1NCC1=CC=C(C(F)(F)F)C=C1 RSXOPFCHOGTEKQ-UHFFFAOYSA-N 0.000 description 1
- DLDVNHYJIZFLMR-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dimethyl-4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]phenyl]acetamide Chemical compound C=1C(C)=C(NC(=O)CC2CCCC2)C(C)=CC=1NCC1=CC=C(C(F)(F)F)N=C1 DLDVNHYJIZFLMR-UHFFFAOYSA-N 0.000 description 1
- UDQPWRNCCSSDOQ-UHFFFAOYSA-N 2-cyclopentyl-n-[2,6-dimethyl-4-[methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]phenyl]acetamide Chemical compound C=1C(C)=C(NC(=O)CC2CCCC2)C(C)=CC=1N(C)CC1=CC=C(C(F)(F)F)C=C1 UDQPWRNCCSSDOQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- IBCAZLGTVOBBRF-UHFFFAOYSA-N 2-cyclopentyl-n-[2-(4-methylphenyl)-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(C)=CC=C1C1=CC(N2CCOCC2)=CC(C(F)(F)F)=C1NC(=O)CC1CCCC1 IBCAZLGTVOBBRF-UHFFFAOYSA-N 0.000 description 1
- OGNZSCJYYOGBKZ-UHFFFAOYSA-N 2-cyclopentyl-n-[2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C(F)(F)F)=C1NC(=O)CC1CCCC1 OGNZSCJYYOGBKZ-UHFFFAOYSA-N 0.000 description 1
- QZCCCEGFZZERCR-UHFFFAOYSA-N 2-cyclopentyl-n-[4-[(3-fluoroanilino)methyl]-2,6-dimethylphenyl]acetamide Chemical compound C=1C(C)=C(NC(=O)CC2CCCC2)C(C)=CC=1CNC1=CC=CC(F)=C1 QZCCCEGFZZERCR-UHFFFAOYSA-N 0.000 description 1
- BPVGYTFULZLUOK-UHFFFAOYSA-N 2-cyclopentyl-n-[4-[(3-methoxyanilino)methyl]-2,6-dimethylphenyl]acetamide Chemical compound COC1=CC=CC(NCC=2C=C(C)C(NC(=O)CC3CCCC3)=C(C)C=2)=C1 BPVGYTFULZLUOK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- UYUQLIZCUOSRRQ-UHFFFAOYSA-N 2-methoxyethyl n-[2,6-dimethyl-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCOC)=C(C)C=C1CNC1=CC=C(C(F)(F)F)C=C1 UYUQLIZCUOSRRQ-UHFFFAOYSA-N 0.000 description 1
- WJLXTOBWTZRKRD-UHFFFAOYSA-N 2-methylpropyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC(C)C)=CC=C1N(C)CC1=CC=C(Cl)S1 WJLXTOBWTZRKRD-UHFFFAOYSA-N 0.000 description 1
- AHDDRJBFJBDEPW-UHFFFAOYSA-N 2-phenylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C1=CC=CC=C1 AHDDRJBFJBDEPW-UHFFFAOYSA-N 0.000 description 1
- ZMTSMVZAFDWQRM-UHFFFAOYSA-N 2-phenylethylurea Chemical compound NC(=O)NCCC1=CC=CC=C1 ZMTSMVZAFDWQRM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- QSRVRUQGIKKYCG-UHFFFAOYSA-N 3,3-dimethyl-n-[1-[(3-methyl-5-phenyl-1,2-oxazol-4-yl)methyl]-2,3-dihydroindol-5-yl]butanamide Chemical compound C1CC2=CC(NC(=O)CC(C)(C)C)=CC=C2N1CC=1C(C)=NOC=1C1=CC=CC=C1 QSRVRUQGIKKYCG-UHFFFAOYSA-N 0.000 description 1
- BLCITWFEHRSCKY-UHFFFAOYSA-N 3,3-dimethyl-n-[1-[(4-propan-2-ylphenyl)methyl]-2,3-dihydroindol-5-yl]butanamide Chemical compound C1=CC(C(C)C)=CC=C1CN1C2=CC=C(NC(=O)CC(C)(C)C)C=C2CC1 BLCITWFEHRSCKY-UHFFFAOYSA-N 0.000 description 1
- SPFJQCNWZDVROJ-UHFFFAOYSA-N 3,3-dimethyl-n-[1-[[6-(4-methylphenoxy)pyridin-3-yl]methyl]-2,3-dihydroindol-5-yl]butanamide Chemical compound C1=CC(C)=CC=C1OC(N=C1)=CC=C1CN1C2=CC=C(NC(=O)CC(C)(C)C)C=C2CC1 SPFJQCNWZDVROJ-UHFFFAOYSA-N 0.000 description 1
- FUWZLYDFJFRKGG-UHFFFAOYSA-N 3,3-dimethyl-n-[2-methyl-4-[(2-phenylpyrimidin-5-yl)methylamino]phenyl]butanamide Chemical compound C1=C(NC(=O)CC(C)(C)C)C(C)=CC(NCC=2C=NC(=NC=2)C=2C=CC=CC=2)=C1 FUWZLYDFJFRKGG-UHFFFAOYSA-N 0.000 description 1
- NJUKIJYUAQHUKN-UHFFFAOYSA-N 3,3-dimethyl-n-[2-methyl-4-[[6-(4-methylphenoxy)pyridin-3-yl]methylamino]phenyl]butanamide Chemical compound C1=CC(C)=CC=C1OC(N=C1)=CC=C1CNC1=CC=C(NC(=O)CC(C)(C)C)C(C)=C1 NJUKIJYUAQHUKN-UHFFFAOYSA-N 0.000 description 1
- FJHHRZVGLKCHRZ-UHFFFAOYSA-N 3,3-dimethyl-n-[2-methyl-4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]phenyl]butanamide Chemical compound C1=C(NC(=O)CC(C)(C)C)C(C)=CC(NCC=2C=NC(=CC=2)C(F)(F)F)=C1 FJHHRZVGLKCHRZ-UHFFFAOYSA-N 0.000 description 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 description 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 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 description 1
- FEBOTPHFXYHVPL-UHFFFAOYSA-N 3-[1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidinyl]-1H-benzimidazol-2-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 FEBOTPHFXYHVPL-UHFFFAOYSA-N 0.000 description 1
- SJAIYFDQCITQLJ-UHFFFAOYSA-N 3-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-1-methyl-1-propylurea Chemical compound C1=C(Cl)C(NC(=O)N(C)CCC)=CC=C1N(C)CC1=CC=C(Cl)S1 SJAIYFDQCITQLJ-UHFFFAOYSA-N 0.000 description 1
- GUJRSXAPGDDABA-NSHDSACASA-N 3-bromo-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2,6-dimethoxybenzamide Chemical compound CCN1CCC[C@H]1CNC(=O)C1=C(OC)C=CC(Br)=C1OC GUJRSXAPGDDABA-NSHDSACASA-N 0.000 description 1
- NKRSJPBJRWPWTO-UHFFFAOYSA-N 3-chloropropyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCCCCl)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 NKRSJPBJRWPWTO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- BIAVGWDGIJKWRM-FQEVSTJZSA-N 3-hydroxy-2-phenyl-n-[(1s)-1-phenylpropyl]quinoline-4-carboxamide Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(O)C=1C1=CC=CC=C1 BIAVGWDGIJKWRM-FQEVSTJZSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- PMXMIIMHBWHSKN-UHFFFAOYSA-N 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCC(O)C4=NC=3C)=NOC2=C1 PMXMIIMHBWHSKN-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- UNBMPKNTYKDYCG-UHFFFAOYSA-N 4-methylpentan-2-amine Chemical compound CC(C)CC(C)N UNBMPKNTYKDYCG-UHFFFAOYSA-N 0.000 description 1
- UOTUGSGYFHMURV-UHFFFAOYSA-N 4-n-[(5-chlorothiophen-2-yl)methyl]-4-n,2-dimethylbenzene-1,4-diamine Chemical compound C=1C=C(N)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 UOTUGSGYFHMURV-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QOYHHIBFXOOADH-UHFFFAOYSA-N 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 QOYHHIBFXOOADH-UHFFFAOYSA-N 0.000 description 1
- SKTFQHRVFFOHTQ-UHFFFAOYSA-N 8-bromo-1,3-dimethyl-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Br)=N2 SKTFQHRVFFOHTQ-UHFFFAOYSA-N 0.000 description 1
- ILMHNKKMKWQVCE-UHFFFAOYSA-N 8-fluoro-12-(4-methylpiperazin-1-yl)-6h-[1]benzothiolo[2,3-b][1,5]benzodiazepine Chemical compound C1CN(C)CCN1C1=NC2=CC=C(F)C=C2NC2=C1C1=CC=CC=C1S2 ILMHNKKMKWQVCE-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 206010001541 Akinesia Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 206010002942 Apathy Diseases 0.000 description 1
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 description 1
- 208000008882 Benign Neonatal Epilepsy Diseases 0.000 description 1
- 206010067866 Benign familial neonatal convulsions Diseases 0.000 description 1
- CYGODHVAJQTCBG-UHFFFAOYSA-N Bifeprunox Chemical compound C=12OC(=O)NC2=CC=CC=1N(CC1)CCN1CC(C=1)=CC=CC=1C1=CC=CC=C1 CYGODHVAJQTCBG-UHFFFAOYSA-N 0.000 description 1
- XVGOZDAJGBALKS-UHFFFAOYSA-N Blonanserin Chemical compound C1CN(CC)CCN1C1=CC(C=2C=CC(F)=CC=2)=C(CCCCCC2)C2=N1 XVGOZDAJGBALKS-UHFFFAOYSA-N 0.000 description 1
- 206010005885 Blunted affect Diseases 0.000 description 1
- RKLNONIVDFXQRX-UHFFFAOYSA-N Bromperidol Chemical compound C1CC(O)(C=2C=CC(Br)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 RKLNONIVDFXQRX-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241001631457 Cannula Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KAAZGXDPUNNEFN-UHFFFAOYSA-N Clotiapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2SC2=CC=C(Cl)C=C12 KAAZGXDPUNNEFN-UHFFFAOYSA-N 0.000 description 1
- 206010010144 Completed suicide Diseases 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- 241000632511 Daviesia arborea Species 0.000 description 1
- 206010012374 Depressed mood Diseases 0.000 description 1
- 108050004812 Dopamine receptor Proteins 0.000 description 1
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 240000005636 Dryobalanops aromatica Species 0.000 description 1
- 241001269524 Dura Species 0.000 description 1
- 206010014557 Emotional poverty Diseases 0.000 description 1
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 1
- 206010017600 Galactorrhoea Diseases 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 101000974726 Homo sapiens Potassium voltage-gated channel subfamily E member 1 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010021030 Hypomania Diseases 0.000 description 1
- 206010022489 Insulin Resistance Diseases 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 108010011185 KCNQ1 Potassium Channel Proteins 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- KLPWJLBORRMFGK-UHFFFAOYSA-N Molindone Chemical compound O=C1C=2C(CC)=C(C)NC=2CCC1CN1CCOCC1 KLPWJLBORRMFGK-UHFFFAOYSA-N 0.000 description 1
- 206010027951 Mood swings Diseases 0.000 description 1
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
- 208000002740 Muscle Rigidity Diseases 0.000 description 1
- CKYSJBCIFKFUNJ-UHFFFAOYSA-N N-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)cyclopropanecarboxamide Chemical compound CC1=CC(=NC(=C1NC(=O)C2CC2)C)N3CCOCC3 CKYSJBCIFKFUNJ-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- JTVPZMFULRWINT-UHFFFAOYSA-N N-[2-(diethylamino)ethyl]-2-methoxy-5-methylsulfonylbenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(S(C)(=O)=O)=CC=C1OC JTVPZMFULRWINT-UHFFFAOYSA-N 0.000 description 1
- JNNOSTQEZICQQP-UHFFFAOYSA-N N-desmethylclozapine Chemical compound N=1C2=CC(Cl)=CC=C2NC2=CC=CC=C2C=1N1CCNCC1 JNNOSTQEZICQQP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZZQNEJILGNNOEP-UHFFFAOYSA-N Ocaperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC3=C(C)N=C4N(C3=O)C=CC=C4C)=NOC2=C1 ZZQNEJILGNNOEP-UHFFFAOYSA-N 0.000 description 1
- 206010030295 Oligomenorrhoea Diseases 0.000 description 1
- XCWPUUGSGHNIDZ-UHFFFAOYSA-N Oxypertine Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(C)=C1CCN(CC1)CCN1C1=CC=CC=C1 XCWPUUGSGHNIDZ-UHFFFAOYSA-N 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229940127315 Potassium Channel Openers Drugs 0.000 description 1
- 102100022755 Potassium voltage-gated channel subfamily E member 1 Human genes 0.000 description 1
- 102100037444 Potassium voltage-gated channel subfamily KQT member 1 Human genes 0.000 description 1
- ZGUGWUXLJSTTMA-UHFFFAOYSA-N Promazinum Chemical compound C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZGUGWUXLJSTTMA-UHFFFAOYSA-N 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 206010037211 Psychomotor hyperactivity Diseases 0.000 description 1
- 206010037213 Psychomotor retardation Diseases 0.000 description 1
- 206010037249 Psychotic behaviour Diseases 0.000 description 1
- 206010054720 Regressive behaviour Diseases 0.000 description 1
- 239000012891 Ringer solution Substances 0.000 description 1
- 208000036752 Schizophrenia, paranoid type Diseases 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- 206010041243 Social avoidant behaviour Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 206010042458 Suicidal ideation Diseases 0.000 description 1
- 206010042464 Suicide attempt Diseases 0.000 description 1
- UNRHXEPDKXPRTM-UHFFFAOYSA-N Sultopride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=CC=C1OC UNRHXEPDKXPRTM-UHFFFAOYSA-N 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 1
- GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 238000010162 Tukey test Methods 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- CHKXOFYAHSTZLN-UHFFFAOYSA-N [2-amino-4-[(5-fluorothiophen-2-yl)methylamino]phenyl]carbamic acid Chemical compound C1=CC(=C(C=C1NCC2=CC=C(S2)F)N)NC(=O)O CHKXOFYAHSTZLN-UHFFFAOYSA-N 0.000 description 1
- LLODXFSZZIRBHM-UHFFFAOYSA-N [2-chloro-4-[methyl-[(4-methylsulfanylphenyl)methyl]amino]phenyl]carbamic acid Chemical compound ClC1=C(C=CC(=C1)N(CC1=CC=C(C=C1)SC)C)NC(O)=O LLODXFSZZIRBHM-UHFFFAOYSA-N 0.000 description 1
- NOSIYYJFMPDDSA-UHFFFAOYSA-N acepromazine Chemical compound C1=C(C(C)=O)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 NOSIYYJFMPDDSA-UHFFFAOYSA-N 0.000 description 1
- 229960005054 acepromazine Drugs 0.000 description 1
- WNTYBHLDCKXEOT-UHFFFAOYSA-N acetophenazine Chemical compound C12=CC(C(=O)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCN(CCO)CC1 WNTYBHLDCKXEOT-UHFFFAOYSA-N 0.000 description 1
- 229960000276 acetophenazine Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 101150109352 acr-16 gene Proteins 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229960003036 amisulpride Drugs 0.000 description 1
- NTJOBXMMWNYJFB-UHFFFAOYSA-N amisulpride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC NTJOBXMMWNYJFB-UHFFFAOYSA-N 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000000228 antimanic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229960004372 aripiprazole Drugs 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 229960005245 asenapine Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 239000003693 atypical antipsychotic agent Substances 0.000 description 1
- 229940127236 atypical antipsychotics Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 201000003452 benign familial neonatal epilepsy Diseases 0.000 description 1
- 201000010295 benign neonatal seizures Diseases 0.000 description 1
- 229960002507 benperidol Drugs 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KAEMILXLUFFLSU-UHFFFAOYSA-N benzyl n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)carbamate Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)OCC1=CC=CC=C1 KAEMILXLUFFLSU-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QIUJJJVRYWFJPB-UHFFFAOYSA-N benzyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCC=2C=CC=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QIUJJJVRYWFJPB-UHFFFAOYSA-N 0.000 description 1
- 229950009087 bifeprunox Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229950002871 blonanserin Drugs 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 229960004037 bromperidol Drugs 0.000 description 1
- YIEKAWKLUNVJSJ-UHFFFAOYSA-N but-2-ynyl carbamate Chemical compound CC#CCOC(N)=O YIEKAWKLUNVJSJ-UHFFFAOYSA-N 0.000 description 1
- NTCMMLFINXWYDI-UHFFFAOYSA-N but-3-enyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCCC=C)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 NTCMMLFINXWYDI-UHFFFAOYSA-N 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- DVLBYTMYSMAKHP-UHFFFAOYSA-N butaperazine Chemical compound C12=CC(C(=O)CCC)=CC=C2SC2=CC=CC=C2N1CCCN1CCN(C)CC1 DVLBYTMYSMAKHP-UHFFFAOYSA-N 0.000 description 1
- 229960000608 butaperazine Drugs 0.000 description 1
- SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 description 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 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 230000005800 cardiovascular problem Effects 0.000 description 1
- 229960005123 cariprazine Drugs 0.000 description 1
- KPWSJANDNDDRMB-QAQDUYKDSA-N cariprazine Chemical compound C1C[C@@H](NC(=O)N(C)C)CC[C@@H]1CCN1CCN(C=2C(=C(Cl)C=CC=2)Cl)CC1 KPWSJANDNDDRMB-QAQDUYKDSA-N 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- DBOUGBAQLIXZLV-UHFFFAOYSA-N chlorproethazine Chemical compound C1=C(Cl)C=C2N(CCCN(CC)CC)C3=CC=CC=C3SC2=C1 DBOUGBAQLIXZLV-UHFFFAOYSA-N 0.000 description 1
- 229960003030 chlorproethazine Drugs 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 229960001552 chlorprothixene Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- NJMYODHXAKYRHW-DVZOWYKESA-N cis-flupenthixol Chemical compound C1CN(CCO)CCN1CC\C=C\1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C2/1 NJMYODHXAKYRHW-DVZOWYKESA-N 0.000 description 1
- 229960001184 clopenthixol Drugs 0.000 description 1
- 229960003864 clotiapine Drugs 0.000 description 1
- 229960004170 clozapine Drugs 0.000 description 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 210000003477 cochlea Anatomy 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 230000007278 cognition impairment Effects 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000003869 coulometry Methods 0.000 description 1
- 229960003368 croscarmellose sodium type a Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- SLFGIOIONGJGRT-UHFFFAOYSA-N cyamemazine Chemical compound C1=C(C#N)C=C2N(CC(CN(C)C)C)C3=CC=CC=C3SC2=C1 SLFGIOIONGJGRT-UHFFFAOYSA-N 0.000 description 1
- 229960004278 cyamemazine Drugs 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005070 decynyl 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])C([H])([H])C#C* 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010252 digital analysis Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MSYUMPGNGDNTIQ-UHFFFAOYSA-N dixyrazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC(C)CN1CCN(CCOCCO)CC1 MSYUMPGNGDNTIQ-UHFFFAOYSA-N 0.000 description 1
- 229960005146 dixyrazine Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- RMEDXOLNCUSCGS-UHFFFAOYSA-N droperidol Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CC=C(N2C(NC3=CC=CC=C32)=O)CC1 RMEDXOLNCUSCGS-UHFFFAOYSA-N 0.000 description 1
- 229960000394 droperidol Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 238000002001 electrophysiology Methods 0.000 description 1
- 230000007831 electrophysiology Effects 0.000 description 1
- 230000003028 elevating effect Effects 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 230000001037 epileptic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- YYIFYTOIDVFSJM-UHFFFAOYSA-N ethyl n-(4-bromo-2,6-dimethylphenyl)carbamate Chemical compound CCOC(=O)NC1=C(C)C=C(Br)C=C1C YYIFYTOIDVFSJM-UHFFFAOYSA-N 0.000 description 1
- IECMFWSPQDIVPW-UHFFFAOYSA-N ethyl n-[2,6-dimethyl-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=C(C)C=C1CNC1=CC=C(C(F)(F)F)C=C1 IECMFWSPQDIVPW-UHFFFAOYSA-N 0.000 description 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 description 1
- TYFOODIYYYOWKK-UHFFFAOYSA-N ethyl n-[2-[4-(dimethylamino)phenyl]-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(C=2C=CC(=CC=2)N(C)C)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 TYFOODIYYYOWKK-UHFFFAOYSA-N 0.000 description 1
- PXEJYQDIFVHJMZ-UHFFFAOYSA-N ethyl n-[2-amino-4-(1-benzothiophen-2-ylmethylamino)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC2=CC=CC=C2S1 PXEJYQDIFVHJMZ-UHFFFAOYSA-N 0.000 description 1
- KXYHFTARJIQOMA-UHFFFAOYSA-N ethyl n-[2-amino-4-(1-benzothiophen-3-ylmethylamino)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CSC2=CC=CC=C12 KXYHFTARJIQOMA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CYVMSJCKTMVSRR-UHFFFAOYSA-N ethyl n-[2-amino-4-(thiophen-2-ylmethylamino)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=CS1 CYVMSJCKTMVSRR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 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 description 1
- GXONDZRSDZSZRZ-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-chloro-4-methylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C)C(Cl)=C1 GXONDZRSDZSZRZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- NGFUMNQGNPBYMN-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-chlorothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=C(Cl)C=CS1 NGFUMNQGNPBYMN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- QVJISOGPNWUYBI-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-methylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=C(C)C=CS1 QVJISOGPNWUYBI-UHFFFAOYSA-N 0.000 description 1
- BSQFTTSXMOOOGH-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-bromo-3-methoxythiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=C(OC)C(Br)=CS1 BSQFTTSXMOOOGH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- WXSQDZHUDQVVFR-UHFFFAOYSA-N ethyl n-[2-amino-4-[(5-bromothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Br)S1 WXSQDZHUDQVVFR-UHFFFAOYSA-N 0.000 description 1
- OWMAWWXIMWNHSI-UHFFFAOYSA-N ethyl n-[2-amino-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(Cl)S1 OWMAWWXIMWNHSI-UHFFFAOYSA-N 0.000 description 1
- OCOIXRNXFUKTKY-UHFFFAOYSA-N ethyl n-[2-amino-4-[(5-ethylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(CC)S1 OCOIXRNXFUKTKY-UHFFFAOYSA-N 0.000 description 1
- WIUHLNPDCTWFEH-UHFFFAOYSA-N ethyl n-[2-amino-4-[(5-fluoro-1-benzofuran-3-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=COC2=CC=C(F)C=C12 WIUHLNPDCTWFEH-UHFFFAOYSA-N 0.000 description 1
- PNYDZEMORIWFHF-UHFFFAOYSA-N ethyl n-[2-amino-4-[(5-phenylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C=2C=CC=CC=2)S1 PNYDZEMORIWFHF-UHFFFAOYSA-N 0.000 description 1
- KKTKRODPSKTNPL-UHFFFAOYSA-N ethyl n-[2-amino-4-[(6-chloro-3-methoxy-1-benzothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=C(OC)C2=CC=C(Cl)C=C2S1 KKTKRODPSKTNPL-UHFFFAOYSA-N 0.000 description 1
- AEBTUIWNDWVQNE-UHFFFAOYSA-N ethyl n-[2-amino-4-[[3-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(C(F)(F)F)=C1 AEBTUIWNDWVQNE-UHFFFAOYSA-N 0.000 description 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 description 1
- 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 description 1
- AQQQGRCQQUTKHH-UHFFFAOYSA-N ethyl n-[2-amino-4-[methyl-[(5-methylthiophen-2-yl)methyl]amino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C)S1 AQQQGRCQQUTKHH-UHFFFAOYSA-N 0.000 description 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 description 1
- 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 description 1
- 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 description 1
- UJHAKAHMBMEMNW-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 UJHAKAHMBMEMNW-UHFFFAOYSA-N 0.000 description 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 description 1
- PXJYWPAJYQOYAU-UHFFFAOYSA-N ethyl n-[2-chloro-4-[methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(F)(F)F)C=C1 PXJYWPAJYQOYAU-UHFFFAOYSA-N 0.000 description 1
- MTYCZZYJZDRZKZ-UHFFFAOYSA-N ethyl n-[2-cyano-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(C#N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 MTYCZZYJZDRZKZ-UHFFFAOYSA-N 0.000 description 1
- GRAKJGFHEIJYDP-UHFFFAOYSA-N ethyl n-[2-cyclopentyloxy-4-[(3-fluoro-2-methylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(OC2CCCC2)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(F)=C1C GRAKJGFHEIJYDP-UHFFFAOYSA-N 0.000 description 1
- QYUKOZHZSRWMNG-UHFFFAOYSA-N ethyl n-[2-cyclopentyloxy-4-[(4-methoxyphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(OC2CCCC2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(OC)C=C1 QYUKOZHZSRWMNG-UHFFFAOYSA-N 0.000 description 1
- FBWLGGCIJQPAGG-UHFFFAOYSA-N ethyl n-[2-fluoro-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(F)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 FBWLGGCIJQPAGG-UHFFFAOYSA-N 0.000 description 1
- HIFLWUPIVYIOKB-UHFFFAOYSA-N ethyl n-[2-methoxy-4-[(3-methylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCC)=CC=C1NCC1=C(C)C=CS1 HIFLWUPIVYIOKB-UHFFFAOYSA-N 0.000 description 1
- DBGKFRUFUABFLM-UHFFFAOYSA-N ethyl n-[2-methoxy-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 DBGKFRUFUABFLM-UHFFFAOYSA-N 0.000 description 1
- GPLMHGDAOVFNCU-UHFFFAOYSA-N ethyl n-[2-methyl-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 GPLMHGDAOVFNCU-UHFFFAOYSA-N 0.000 description 1
- VLIKNAITKKRTJV-UHFFFAOYSA-N ethyl n-[2-methyl-4-[(5-phenylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C=2C=CC=CC=2)S1 VLIKNAITKKRTJV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- FJGJSYHAKOHFMZ-UHFFFAOYSA-N ethyl n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 FJGJSYHAKOHFMZ-UHFFFAOYSA-N 0.000 description 1
- LBPNSUIVYSELKA-UHFFFAOYSA-N ethyl n-[4-(1-benzothiophen-2-ylmethylamino)-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NCC1=CC2=CC=CC=C2S1 LBPNSUIVYSELKA-UHFFFAOYSA-N 0.000 description 1
- MBZCXPYDDKNMKD-UHFFFAOYSA-N ethyl n-[4-(1-benzothiophen-2-ylmethylamino)-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC2=CC=CC=C2S1 MBZCXPYDDKNMKD-UHFFFAOYSA-N 0.000 description 1
- XDKSFHCRKBLVPN-UHFFFAOYSA-N ethyl n-[4-[(2,4-difluorophenyl)methylamino]-2-methoxyphenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCC)=CC=C1NCC1=CC=C(F)C=C1F XDKSFHCRKBLVPN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- DHNIHGLWXHLYGU-UHFFFAOYSA-N ethyl n-[4-[(3-fluoro-2-methylphenyl)methylamino]-2-(2-phenylethoxy)phenyl]carbamate Chemical compound C1=C(OCCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(F)=C1C DHNIHGLWXHLYGU-UHFFFAOYSA-N 0.000 description 1
- DDLKIMUNVILAIR-UHFFFAOYSA-N ethyl n-[4-[(3-fluoro-2-methylphenyl)methylamino]-2-phenylmethoxyphenyl]carbamate Chemical compound C1=C(OCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(F)=C1C DDLKIMUNVILAIR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- LCEODKNUZATZLW-UHFFFAOYSA-N ethyl n-[4-[(3-methoxyphenyl)methylamino]-2-phenylmethoxyphenyl]carbamate Chemical compound C1=C(OCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(OC)=C1 LCEODKNUZATZLW-UHFFFAOYSA-N 0.000 description 1
- TZNQYORNTRQEJV-UHFFFAOYSA-N ethyl n-[4-[(4-chloro-3-fluoroanilino)methyl]-2-fluorophenyl]carbamate Chemical compound C1=C(F)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C(F)=C1 TZNQYORNTRQEJV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- QCEHDLKQWVGPFI-UHFFFAOYSA-N ethyl n-[4-[(4-chlorophenyl)methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)C=C1 QCEHDLKQWVGPFI-UHFFFAOYSA-N 0.000 description 1
- NWLXPWFNBKJVKX-UHFFFAOYSA-N ethyl n-[4-[(4-fluorophenyl)methyl-methylamino]-2-propan-2-yloxyphenyl]carbamate Chemical compound C1=C(OC(C)C)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(F)C=C1 NWLXPWFNBKJVKX-UHFFFAOYSA-N 0.000 description 1
- XKSCLMWYIAIGGH-UHFFFAOYSA-N ethyl n-[4-[(4-methylsulfanylphenyl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1NCC1=CC=C(SC)C=C1 XKSCLMWYIAIGGH-UHFFFAOYSA-N 0.000 description 1
- FUOWMPZQNQMKQJ-UHFFFAOYSA-N ethyl n-[4-[(4-methylsulfanylphenyl)methylamino]-2-phenylmethoxyphenyl]carbamate Chemical compound C1=C(OCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(SC)C=C1 FUOWMPZQNQMKQJ-UHFFFAOYSA-N 0.000 description 1
- AYJLXGFLEJCNSS-UHFFFAOYSA-N ethyl n-[4-[(4-tert-butylphenyl)methyl-methylamino]-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(C)(C)C)C=C1 AYJLXGFLEJCNSS-UHFFFAOYSA-N 0.000 description 1
- LZCPHDBEDLLPCH-UHFFFAOYSA-N ethyl n-[4-[(5-bromothiophen-2-yl)methyl-methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(Br)S1 LZCPHDBEDLLPCH-UHFFFAOYSA-N 0.000 description 1
- CZIYBKSESQHEMY-UHFFFAOYSA-N ethyl n-[4-[(5-bromothiophen-2-yl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Br)S1 CZIYBKSESQHEMY-UHFFFAOYSA-N 0.000 description 1
- BNRZQCLVVKMSIW-UHFFFAOYSA-N ethyl n-[4-[(5-bromothiophen-2-yl)methylamino]-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Br)S1 BNRZQCLVVKMSIW-UHFFFAOYSA-N 0.000 description 1
- URCRJUUPLVVVDL-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(Cl)S1 URCRJUUPLVVVDL-UHFFFAOYSA-N 0.000 description 1
- JBIFACVOFRVYLT-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 JBIFACVOFRVYLT-UHFFFAOYSA-N 0.000 description 1
- PPNRDWUDMHIESH-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-iodophenyl]carbamate Chemical compound C1=C(I)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 PPNRDWUDMHIESH-UHFFFAOYSA-N 0.000 description 1
- ZWTUCGJBUWCVJO-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 ZWTUCGJBUWCVJO-UHFFFAOYSA-N 0.000 description 1
- PCPKDKGFFJFEJT-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-quinolin-3-ylphenyl]carbamate Chemical compound C1=C(C=2C=C3C=CC=CC3=NC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 PCPKDKGFFJFEJT-UHFFFAOYSA-N 0.000 description 1
- KPERHISRLWKTQA-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-quinolin-5-ylphenyl]carbamate Chemical compound C1=C(C=2C3=CC=CN=C3C=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 KPERHISRLWKTQA-UHFFFAOYSA-N 0.000 description 1
- GAYMQGPGTVLOQU-UHFFFAOYSA-N ethyl n-[4-[methyl-[(4-methylsulfanylphenyl)methyl]amino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(SC)C=C1 GAYMQGPGTVLOQU-UHFFFAOYSA-N 0.000 description 1
- IMUOXPRZLBQDQK-UHFFFAOYSA-N ethyl n-[4-[methyl-[(4-propan-2-ylphenyl)methyl]amino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(C)C)C=C1 IMUOXPRZLBQDQK-UHFFFAOYSA-N 0.000 description 1
- LUCIULMHEDDUDH-UHFFFAOYSA-N ethyl n-[4-[methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(F)(F)F)C=C1 LUCIULMHEDDUDH-UHFFFAOYSA-N 0.000 description 1
- 230000005713 exacerbation Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- IRYFCWPNDIUQOW-UHFFFAOYSA-N fluanisone Chemical compound COC1=CC=CC=C1N1CCN(CCCC(=O)C=2C=CC(F)=CC=2)CC1 IRYFCWPNDIUQOW-UHFFFAOYSA-N 0.000 description 1
- 229960005220 fluanisone Drugs 0.000 description 1
- 229960002419 flupentixol Drugs 0.000 description 1
- 229960002690 fluphenazine Drugs 0.000 description 1
- 229960003532 fluspirilene Drugs 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 201000000079 gynecomastia Diseases 0.000 description 1
- 210000002768 hair cell Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 210000004295 hippocampal neuron Anatomy 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 230000000742 histaminergic effect Effects 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000035863 hyperlocomotion Effects 0.000 description 1
- 229960003162 iloperidone Drugs 0.000 description 1
- XMXHEBAFVSFQEX-UHFFFAOYSA-N iloperidone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C=2C3=CC=C(F)C=C3ON=2)CC1 XMXHEBAFVSFQEX-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 229960004145 levosulpiride Drugs 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 229940073577 lithium chloride Drugs 0.000 description 1
- 229960000423 loxapine Drugs 0.000 description 1
- XJGVXQDUIWGIRW-UHFFFAOYSA-N loxapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 XJGVXQDUIWGIRW-UHFFFAOYSA-N 0.000 description 1
- 229960001432 lurasidone Drugs 0.000 description 1
- PQXKDMSYBGKCJA-CVTJIBDQSA-N lurasidone Chemical compound C1=CC=C2C(N3CCN(CC3)C[C@@H]3CCCC[C@H]3CN3C(=O)[C@@H]4[C@H]5CC[C@H](C5)[C@@H]4C3=O)=NSC2=C1 PQXKDMSYBGKCJA-CVTJIBDQSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229960001861 melperone Drugs 0.000 description 1
- SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 description 1
- 229960000300 mesoridazine Drugs 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- VRQVVMDWGGWHTJ-CQSZACIVSA-N methotrimeprazine Chemical compound C1=CC=C2N(C[C@H](C)CN(C)C)C3=CC(OC)=CC=C3SC2=C1 VRQVVMDWGGWHTJ-CQSZACIVSA-N 0.000 description 1
- 229940042053 methotrimeprazine Drugs 0.000 description 1
- ZWBZSWWTAABAAW-UHFFFAOYSA-N methyl 3-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylanilino]-3-oxopropanoate Chemical compound C1=C(C)C(NC(=O)CC(=O)OC)=CC=C1N(C)CC1=CC=C(Cl)S1 ZWBZSWWTAABAAW-UHFFFAOYSA-N 0.000 description 1
- GIOTXFVSHZODRM-UHFFFAOYSA-N methyl 4-[[3-methyl-4-(propoxycarbonylamino)anilino]methyl]benzoate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(=O)OC)C=C1 GIOTXFVSHZODRM-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 238000000520 microinjection Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229960004938 molindone Drugs 0.000 description 1
- 229940127237 mood stabilizer Drugs 0.000 description 1
- AGAHNABIDCTLHW-UHFFFAOYSA-N moperone Chemical compound C1=CC(C)=CC=C1C1(O)CCN(CCCC(=O)C=2C=CC(F)=CC=2)CC1 AGAHNABIDCTLHW-UHFFFAOYSA-N 0.000 description 1
- 229960000758 moperone Drugs 0.000 description 1
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 description 1
- 229960003894 mosapramine Drugs 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- VRDZAGWZCGIZSC-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-thiophen-2-ylacetamide Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)CC1=CC=CS1 VRDZAGWZCGIZSC-UHFFFAOYSA-N 0.000 description 1
- BLESCNKLEXGCBO-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-4-methylpentanamide Chemical compound N1=C(C)C(NC(=O)CCC(C)C)=C(C)C=C1N1CCOCC1 BLESCNKLEXGCBO-UHFFFAOYSA-N 0.000 description 1
- LRPPLNWCCXUMIQ-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-5-methylhexanamide Chemical compound N1=C(C)C(NC(=O)CCCC(C)C)=C(C)C=C1N1CCOCC1 LRPPLNWCCXUMIQ-UHFFFAOYSA-N 0.000 description 1
- RZPBJOUKSLGPAK-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)heptanamide Chemical compound N1=C(C)C(NC(=O)CCCCCC)=C(C)C=C1N1CCOCC1 RZPBJOUKSLGPAK-UHFFFAOYSA-N 0.000 description 1
- SAHHONAYVKIMTP-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)hexanamide Chemical compound N1=C(C)C(NC(=O)CCCCC)=C(C)C=C1N1CCOCC1 SAHHONAYVKIMTP-UHFFFAOYSA-N 0.000 description 1
- QHRDANBBSJKUAT-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)octanamide Chemical compound N1=C(C)C(NC(=O)CCCCCCC)=C(C)C=C1N1CCOCC1 QHRDANBBSJKUAT-UHFFFAOYSA-N 0.000 description 1
- UANXUOHOUIPKAT-UHFFFAOYSA-N n-(2,4-dimethyl-6-quinolin-3-ylphenyl)-2-(4-fluorophenyl)acetamide Chemical compound C=1N=C2C=CC=CC2=CC=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 UANXUOHOUIPKAT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- RQMWEJOBHGLLHJ-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2,3-dihydro-1-benzofuran-2-carboxamide Chemical compound C=1C(C)=C(NC(=O)C2OC3=CC=CC=C3C2)C(C)=CC=1N1CCOCC1 RQMWEJOBHGLLHJ-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
- KGFIFQDRJDJCKS-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound C1=C(C)C(NC(=O)C)=C(C)C=C1N1CCOCC1 KGFIFQDRJDJCKS-UHFFFAOYSA-N 0.000 description 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 description 1
- RPVLAQSRQQXWEJ-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)hex-5-enamide Chemical compound CC1=C(NC(=O)CCCC=C)C(C)=CC(N2CCOCC2)=C1 RPVLAQSRQQXWEJ-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
- JQAHNNUCWWVTBF-UHFFFAOYSA-N n-(2-amino-4-bromo-6-methylphenyl)-3,3-dimethylbutanamide Chemical compound CC1=CC(Br)=CC(N)=C1NC(=O)CC(C)(C)C JQAHNNUCWWVTBF-UHFFFAOYSA-N 0.000 description 1
- LMHIKBQBDWYIPR-UHFFFAOYSA-N n-(2-bromo-4,6-dichlorophenyl)-2-(4-fluorophenyl)acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC1=C(Cl)C=C(Cl)C=C1Br LMHIKBQBDWYIPR-UHFFFAOYSA-N 0.000 description 1
- AYWFSTLPGFXGPN-UHFFFAOYSA-N n-(2-bromo-4,6-dichlorophenyl)-2-cyclopentylacetamide Chemical compound BrC1=CC(Cl)=CC(Cl)=C1NC(=O)CC1CCCC1 AYWFSTLPGFXGPN-UHFFFAOYSA-N 0.000 description 1
- KGYPPALBQMVEFK-UHFFFAOYSA-N n-(2-bromo-4,6-dimethylphenyl)-2-(4-fluorophenyl)acetamide Chemical compound BrC1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 KGYPPALBQMVEFK-UHFFFAOYSA-N 0.000 description 1
- NOGJERYUQWFZSH-UHFFFAOYSA-N n-(2-bromo-4,6-dimethylphenyl)-2-cyclopentylacetamide Chemical compound BrC1=CC(C)=CC(C)=C1NC(=O)CC1CCCC1 NOGJERYUQWFZSH-UHFFFAOYSA-N 0.000 description 1
- OBGRLHUKTLMALQ-UHFFFAOYSA-N n-(2-bromo-4,6-dimethylphenyl)-3,3-dimethylbutanamide Chemical compound CC1=CC(C)=C(NC(=O)CC(C)(C)C)C(Br)=C1 OBGRLHUKTLMALQ-UHFFFAOYSA-N 0.000 description 1
- JXZMYIPYHBOYME-UHFFFAOYSA-N n-(2-chloro-4-methoxy-6-morpholin-4-ylpyridin-3-yl)-2-cyclopentylacetamide Chemical compound COC1=CC(N2CCOCC2)=NC(Cl)=C1NC(=O)CC1CCCC1 JXZMYIPYHBOYME-UHFFFAOYSA-N 0.000 description 1
- PWTTZEIOVBSDKM-UHFFFAOYSA-N n-(2-chloro-4-methoxy-6-morpholin-4-ylpyridin-3-yl)-3,3-dimethylbutanamide Chemical compound ClC1=C(NC(=O)CC(C)(C)C)C(OC)=CC(N2CCOCC2)=N1 PWTTZEIOVBSDKM-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
- CZEOTFCOTGFZPR-UHFFFAOYSA-N n-(4,6-dimethyl-2-morpholin-4-ylpyrimidin-5-yl)-2-(3-fluorophenyl)acetamide Chemical compound CC1=NC(N2CCOCC2)=NC(C)=C1NC(=O)CC1=CC=CC(F)=C1 CZEOTFCOTGFZPR-UHFFFAOYSA-N 0.000 description 1
- BGZXWAKABKRXEW-UHFFFAOYSA-N n-(4,6-dimethyl-2-morpholin-4-ylpyrimidin-5-yl)-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=NC(N2CCOCC2)=N1 BGZXWAKABKRXEW-UHFFFAOYSA-N 0.000 description 1
- CUYIVYGWYZOZCL-UHFFFAOYSA-N n-(4,6-dimethyl-2-morpholin-4-ylpyrimidin-5-yl)hexanamide Chemical compound N1=C(C)C(NC(=O)CCCCC)=C(C)N=C1N1CCOCC1 CUYIVYGWYZOZCL-UHFFFAOYSA-N 0.000 description 1
- CRNGWJTUEOBSCH-UHFFFAOYSA-N n-(4-bromo-2,6-dimethylphenyl)-2-(4-chlorophenyl)acetamide Chemical compound CC1=CC(Br)=CC(C)=C1NC(=O)CC1=CC=C(Cl)C=C1 CRNGWJTUEOBSCH-UHFFFAOYSA-N 0.000 description 1
- GHQWOAYHLGEKSK-UHFFFAOYSA-N n-(4-bromo-2,6-dimethylphenyl)-2-(4-fluorophenyl)acetamide Chemical compound CC1=CC(Br)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 GHQWOAYHLGEKSK-UHFFFAOYSA-N 0.000 description 1
- BRSMPKRBMIMHTN-UHFFFAOYSA-N n-(4-bromo-2,6-dimethylphenyl)-2-thiophen-2-ylacetamide Chemical compound CC1=CC(Br)=CC(C)=C1NC(=O)CC1=CC=CS1 BRSMPKRBMIMHTN-UHFFFAOYSA-N 0.000 description 1
- MCBBKIXEHFOEKH-UHFFFAOYSA-N n-(4-bromo-2,6-dimethylphenyl)hexanamide Chemical compound CCCCCC(=O)NC1=C(C)C=C(Br)C=C1C MCBBKIXEHFOEKH-UHFFFAOYSA-N 0.000 description 1
- RWXAELOLLOUEEU-UHFFFAOYSA-N n-(4-bromo-2,6-dimethylphenyl)pentanamide Chemical compound CCCCC(=O)NC1=C(C)C=C(Br)C=C1C RWXAELOLLOUEEU-UHFFFAOYSA-N 0.000 description 1
- MVPLWTHYLWWKGV-UHFFFAOYSA-N n-(4-bromo-2-methyl-6-morpholin-4-ylphenyl)-3,3-dimethylbutanamide Chemical compound CC1=CC(Br)=CC(N2CCOCC2)=C1NC(=O)CC(C)(C)C MVPLWTHYLWWKGV-UHFFFAOYSA-N 0.000 description 1
- FNGCWQBVWMPXRW-UHFFFAOYSA-N n-(4-chloro-2-methoxy-6-morpholin-4-ylpyridin-3-yl)propanamide Chemical compound N1=C(OC)C(NC(=O)CC)=C(Cl)C=C1N1CCOCC1 FNGCWQBVWMPXRW-UHFFFAOYSA-N 0.000 description 1
- NFZIHKNNXDBZMI-UHFFFAOYSA-N n-[1-[(5-chlorothiophen-2-yl)methyl]-2,3-dihydroindol-5-yl]-2-phenoxyacetamide Chemical compound S1C(Cl)=CC=C1CN1C2=CC=C(NC(=O)COC=3C=CC=CC=3)C=C2CC1 NFZIHKNNXDBZMI-UHFFFAOYSA-N 0.000 description 1
- OGDBRAJYGVGTPX-UHFFFAOYSA-N n-[1-[[5-(4-chlorophenoxy)-1,3-dimethylpyrazol-4-yl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1CC2=CC(NC(=O)CC(C)(C)C)=CC=C2N1CC=1C(C)=NN(C)C=1OC1=CC=C(Cl)C=C1 OGDBRAJYGVGTPX-UHFFFAOYSA-N 0.000 description 1
- JRMUSINHKOFJFV-UHFFFAOYSA-N n-[2,4-dimethyl-6-(2,2,5-trimethyl-3h-1-benzofuran-7-yl)phenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C(C)=CC=2CC(C)(C)OC=2C=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 JRMUSINHKOFJFV-UHFFFAOYSA-N 0.000 description 1
- XAONIUOGFLUMOE-UHFFFAOYSA-N n-[2,4-dimethyl-6-(4-propan-2-ylphenyl)phenyl]-3,3-dimethylbutanamide Chemical compound C1=CC(C(C)C)=CC=C1C1=CC(C)=CC(C)=C1NC(=O)CC(C)(C)C XAONIUOGFLUMOE-UHFFFAOYSA-N 0.000 description 1
- BQIIVIXQLUJZJJ-UHFFFAOYSA-N n-[2,6-dimethyl-4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]phenyl]-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=CC(NCC=2C=NC(=CC=2)C(F)(F)F)=C1 BQIIVIXQLUJZJJ-UHFFFAOYSA-N 0.000 description 1
- SXSIMUQLWHAEGS-UHFFFAOYSA-N n-[2-(3-cyanophenyl)-4,6-dimethylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=CC(C#N)=CC=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 SXSIMUQLWHAEGS-UHFFFAOYSA-N 0.000 description 1
- KECGJWZRAYXEMQ-UHFFFAOYSA-N n-[2-(4-ethenylphenyl)-4,6-dimethylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C(C=C)C=CC=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 KECGJWZRAYXEMQ-UHFFFAOYSA-N 0.000 description 1
- LXGHGBFMMWWRPL-UHFFFAOYSA-N n-[2-[3,5-bis(trifluoromethyl)phenyl]-4,6-dimethylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 LXGHGBFMMWWRPL-UHFFFAOYSA-N 0.000 description 1
- ISMXZIBRJLAXBF-UHFFFAOYSA-N n-[2-[4-(dimethylamino)phenyl]-4,6-dimethylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 ISMXZIBRJLAXBF-UHFFFAOYSA-N 0.000 description 1
- ILXWQQLVKRBUAO-UHFFFAOYSA-N n-[2-amino-4-[(3-fluoroanilino)methyl]phenyl]-2,2-dimethylpropanamide Chemical compound C1=C(N)C(NC(=O)C(C)(C)C)=CC=C1CNC1=CC=CC(F)=C1 ILXWQQLVKRBUAO-UHFFFAOYSA-N 0.000 description 1
- GOXFPLZEUOSYNS-UHFFFAOYSA-N n-[2-amino-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(N)=CC=1NCC1=CC=C(Cl)S1 GOXFPLZEUOSYNS-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- VEZLUWKLAGYAPU-UHFFFAOYSA-N n-[2-bromo-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]-2-cyclopentylacetamide Chemical compound FC(F)(F)C1=CC(N2CCOCC2)=CC(Br)=C1NC(=O)CC1CCCC1 VEZLUWKLAGYAPU-UHFFFAOYSA-N 0.000 description 1
- ZAWSOIRSBNEJNI-UHFFFAOYSA-N n-[2-bromo-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]-3-cyclohexylpropanamide Chemical compound FC(F)(F)C1=CC(N2CCOCC2)=CC(Br)=C1NC(=O)CCC1CCCCC1 ZAWSOIRSBNEJNI-UHFFFAOYSA-N 0.000 description 1
- LNEODKACMQDIAF-UHFFFAOYSA-N n-[2-bromo-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]-3-cyclopentylpropanamide Chemical compound FC(F)(F)C1=CC(N2CCOCC2)=CC(Br)=C1NC(=O)CCC1CCCC1 LNEODKACMQDIAF-UHFFFAOYSA-N 0.000 description 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 description 1
- AOSDPVXNYCUYSW-UHFFFAOYSA-N n-[2-chloro-4-[(3,4-dichloroanilino)methyl]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C(Cl)=C1 AOSDPVXNYCUYSW-UHFFFAOYSA-N 0.000 description 1
- HSXJTDIWKDHOPI-UHFFFAOYSA-N n-[2-chloro-4-[(3-fluoroanilino)methyl]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1CNC1=CC=CC(F)=C1 HSXJTDIWKDHOPI-UHFFFAOYSA-N 0.000 description 1
- DBLOEDMPCORMST-UHFFFAOYSA-N n-[2-chloro-4-[(4-chloro-3-fluoroanilino)methyl]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C(F)=C1 DBLOEDMPCORMST-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- DSPRNVSQYVZCFI-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2,2,2-trifluoroacetamide Chemical compound C=1C=C(NC(=O)C(F)(F)F)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 DSPRNVSQYVZCFI-UHFFFAOYSA-N 0.000 description 1
- RJIRJOHWLZOJNX-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2C(=CC(=CC=2)N(C)CC=2SC(Cl)=CC=2)Cl)=C1 RJIRJOHWLZOJNX-UHFFFAOYSA-N 0.000 description 1
- QQMOLIHEOHSEJW-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QQMOLIHEOHSEJW-UHFFFAOYSA-N 0.000 description 1
- HJUMLZPJCRCVMP-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-2-thiophen-2-ylacetamide Chemical compound C=1C=C(NC(=O)CC=2SC=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 HJUMLZPJCRCVMP-UHFFFAOYSA-N 0.000 description 1
- QOJZWSIRHHMUND-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-3-cyclohexylpropanamide Chemical compound C=1C=C(NC(=O)CCC2CCCCC2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QOJZWSIRHHMUND-UHFFFAOYSA-N 0.000 description 1
- ZXIJIODJNIISBC-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1N(C)CC1=CC=C(Cl)S1 ZXIJIODJNIISBC-UHFFFAOYSA-N 0.000 description 1
- ICTXQIPJUUCOJP-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]cyclobutanecarboxamide Chemical compound C=1C=C(NC(=O)C2CCC2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 ICTXQIPJUUCOJP-UHFFFAOYSA-N 0.000 description 1
- GTFNEWRWVYJMGD-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]cyclopentanecarboxamide Chemical compound C=1C=C(NC(=O)C2CCCC2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 GTFNEWRWVYJMGD-UHFFFAOYSA-N 0.000 description 1
- QVVCRTNUUALZJM-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]cyclopropanecarboxamide Chemical compound C=1C=C(NC(=O)C2CC2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QVVCRTNUUALZJM-UHFFFAOYSA-N 0.000 description 1
- KTVYZDPJAAPEAD-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]pentanamide Chemical compound C1=C(Cl)C(NC(=O)CCCC)=CC=C1N(C)CC1=CC=C(Cl)S1 KTVYZDPJAAPEAD-UHFFFAOYSA-N 0.000 description 1
- LDARJHDVQXQBCR-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)C1=CC=C(OCCO2)C2=C1 LDARJHDVQXQBCR-UHFFFAOYSA-N 0.000 description 1
- GZPCNLCZYOCMLW-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2C(=CC(NCC=3SC(Cl)=CC=3)=CC=2)Cl)=C1 GZPCNLCZYOCMLW-UHFFFAOYSA-N 0.000 description 1
- BLZIGMLBKKOBNU-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC(C(=C1)Cl)=CC=C1NCC1=CC=C(Cl)S1 BLZIGMLBKKOBNU-UHFFFAOYSA-N 0.000 description 1
- OOFJORNTRHEEFY-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2-thiophen-2-ylacetamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)CC1=CC=CS1 OOFJORNTRHEEFY-UHFFFAOYSA-N 0.000 description 1
- UHHGGSIKLWJNOT-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-3-cyclohexylpropanamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)CCC1CCCCC1 UHHGGSIKLWJNOT-UHFFFAOYSA-N 0.000 description 1
- FVRNPBWTHTZVBH-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]cyclopropanecarboxamide Chemical compound S1C(Cl)=CC=C1CNC(C=C1Cl)=CC=C1NC(=O)C1CC1 FVRNPBWTHTZVBH-UHFFFAOYSA-N 0.000 description 1
- HMSYDJFUVJCDSK-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]pentanamide Chemical compound C1=C(Cl)C(NC(=O)CCCC)=CC=C1NCC1=CC=C(Cl)S1 HMSYDJFUVJCDSK-UHFFFAOYSA-N 0.000 description 1
- 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 description 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 description 1
- VRZOMCHSAMLLPJ-UHFFFAOYSA-N n-[2-chloro-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]-2-cyclopentylacetamide Chemical compound FC(F)(F)C1=CC(N2CCOCC2)=CC(Cl)=C1NC(=O)CC1CCCC1 VRZOMCHSAMLLPJ-UHFFFAOYSA-N 0.000 description 1
- NUVDMQHUVICNHC-UHFFFAOYSA-N n-[2-chloro-6-(trifluoromethyl)-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]-2-cyclopentylacetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC(C=C1C(F)(F)F)=CC(Cl)=C1NC(=O)CC1CCCC1 NUVDMQHUVICNHC-UHFFFAOYSA-N 0.000 description 1
- GEUIQJWDQZWGRE-UHFFFAOYSA-N n-[2-methoxy-4-[(4-propan-2-ylphenyl)methylamino]phenyl]butanamide Chemical compound C1=C(OC)C(NC(=O)CCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 GEUIQJWDQZWGRE-UHFFFAOYSA-N 0.000 description 1
- TUXZGMKFRZJZSM-UHFFFAOYSA-N n-[2-methoxy-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]butanamide Chemical compound C1=C(OC)C(NC(=O)CCC)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 TUXZGMKFRZJZSM-UHFFFAOYSA-N 0.000 description 1
- JSYCSVLZYSFSBB-UHFFFAOYSA-N n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]-2-morpholin-4-ylacetamide Chemical compound C=1C=C(NC(=O)CN2CCOCC2)C(C)=CC=1NCC1=CC=C(C(F)(F)F)C=C1 JSYCSVLZYSFSBB-UHFFFAOYSA-N 0.000 description 1
- NDZPOHAYEUWMTA-UHFFFAOYSA-N n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]-2-piperidin-1-ylacetamide Chemical compound C=1C=C(NC(=O)CN2CCCCC2)C(C)=CC=1NCC1=CC=C(C(F)(F)F)C=C1 NDZPOHAYEUWMTA-UHFFFAOYSA-N 0.000 description 1
- AQDSFYZMSFHLTN-UHFFFAOYSA-N n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]-2-pyrrolidin-1-ylacetamide Chemical compound C=1C=C(NC(=O)CN2CCCC2)C(C)=CC=1NCC1=CC=C(C(F)(F)F)C=C1 AQDSFYZMSFHLTN-UHFFFAOYSA-N 0.000 description 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 description 1
- YYXJEXZKPIYXQH-UHFFFAOYSA-N n-[4-(azepan-1-yl)-2,6-dimethylphenyl]-2-cyclopentylacetamide Chemical compound CC1=CC(N2CCCCCC2)=CC(C)=C1NC(=O)CC1CCCC1 YYXJEXZKPIYXQH-UHFFFAOYSA-N 0.000 description 1
- NHXHKDUACVRVPF-UHFFFAOYSA-N n-[4-[(3,4-dichloroanilino)methyl]-2-fluorophenyl]butanamide Chemical compound C1=C(F)C(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C(Cl)=C1 NHXHKDUACVRVPF-UHFFFAOYSA-N 0.000 description 1
- IIHYQCLDAORSCI-UHFFFAOYSA-N n-[4-[(3,4-dichloroanilino)methyl]-2-methylphenyl]butanamide Chemical compound C1=C(C)C(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C(Cl)=C1 IIHYQCLDAORSCI-UHFFFAOYSA-N 0.000 description 1
- USVPVZBUNHDWDV-UHFFFAOYSA-N n-[4-[(3,4-dichloroanilino)methyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C(Cl)=C1 USVPVZBUNHDWDV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KEJHLHSTFNWOIR-UHFFFAOYSA-N n-[4-[(4-chloro-3-fluoroanilino)methyl]-2-methylphenyl]butanamide Chemical compound C1=C(C)C(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C(F)=C1 KEJHLHSTFNWOIR-UHFFFAOYSA-N 0.000 description 1
- CKRMGYYYPLOCHM-UHFFFAOYSA-N n-[4-[(4-chloro-3-fluoroanilino)methyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C(F)=C1 CKRMGYYYPLOCHM-UHFFFAOYSA-N 0.000 description 1
- SWJZWKSJUDGALQ-UHFFFAOYSA-N n-[4-[(4-chloroanilino)methyl]-2,6-dimethylphenyl]-2-cyclopentylacetamide Chemical compound C=1C(C)=C(NC(=O)CC2CCCC2)C(C)=CC=1CNC1=CC=C(Cl)C=C1 SWJZWKSJUDGALQ-UHFFFAOYSA-N 0.000 description 1
- YNWPLUKYJAPYJQ-UHFFFAOYSA-N n-[4-[(4-chloroanilino)methyl]-2-fluorophenyl]butanamide Chemical compound C1=C(F)C(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C=C1 YNWPLUKYJAPYJQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- LJRXFNXMIQEJIO-UHFFFAOYSA-N n-[4-[(4-tert-butylphenyl)methylamino]-2-methoxyphenyl]butanamide Chemical compound C1=C(OC)C(NC(=O)CCC)=CC=C1NCC1=CC=C(C(C)(C)C)C=C1 LJRXFNXMIQEJIO-UHFFFAOYSA-N 0.000 description 1
- PUWKCSUQTQBIRA-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-2,2-dimethylpropanamide Chemical compound C=1C=C(NC(=O)C(C)(C)C)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 PUWKCSUQTQBIRA-UHFFFAOYSA-N 0.000 description 1
- XFEGTPTVEMIAHI-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 XFEGTPTVEMIAHI-UHFFFAOYSA-N 0.000 description 1
- BBSKYLLMPFIUPS-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC=C(N(C)CC=2SC(Cl)=CC=2)C=C1C BBSKYLLMPFIUPS-UHFFFAOYSA-N 0.000 description 1
- LVTRCLBSFHCSJM-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-2-phenylacetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC=CC=2)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 LVTRCLBSFHCSJM-UHFFFAOYSA-N 0.000 description 1
- FZSKMPVDJNZYPW-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-2-thiophen-2-ylacetamide Chemical compound C=1C=C(NC(=O)CC=2SC=CC=2)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 FZSKMPVDJNZYPW-UHFFFAOYSA-N 0.000 description 1
- ZANNEMGAMBXAJH-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]-3-phenylpropanamide Chemical compound C=1C=C(NC(=O)CCC=2C=CC=CC=2)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 ZANNEMGAMBXAJH-UHFFFAOYSA-N 0.000 description 1
- MQGPHTBVVQWZAS-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]butanamide Chemical compound C1=C(C)C(NC(=O)CCC)=CC=C1N(C)CC1=CC=C(Cl)S1 MQGPHTBVVQWZAS-UHFFFAOYSA-N 0.000 description 1
- SBGPXKACAAELIX-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]cyclobutanecarboxamide Chemical compound C=1C=C(NC(=O)C2CCC2)C(C)=CC=1N(C)CC1=CC=C(Cl)S1 SBGPXKACAAELIX-UHFFFAOYSA-N 0.000 description 1
- VCUGNXTWGUQSIK-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylphenyl]pentanamide Chemical compound C1=C(C)C(NC(=O)CCCC)=CC=C1N(C)CC1=CC=C(Cl)S1 VCUGNXTWGUQSIK-UHFFFAOYSA-N 0.000 description 1
- RHEJEMHTZMPVHX-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-[4-(dimethylamino)phenyl]phenyl]-2-(4-fluorophenyl)acetamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CC(NCC=2SC(Cl)=CC=2)=CC=C1NC(=O)CC1=CC=C(F)C=C1 RHEJEMHTZMPVHX-UHFFFAOYSA-N 0.000 description 1
- TXYYXEJXGQEJQO-UHFFFAOYSA-N n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-iodophenyl]-2-(4-fluorophenyl)acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC(C(=C1)I)=CC=C1NCC1=CC=C(Cl)S1 TXYYXEJXGQEJQO-UHFFFAOYSA-N 0.000 description 1
- HYHPENAHMAZITK-UHFFFAOYSA-N n-[4-[2-(2-chlorophenyl)thiomorpholin-4-yl]-2,6-dimethylphenyl]-2-cyclopentylacetamide Chemical compound CC1=CC(N2CC(SCC2)C=2C(=CC=CC=2)Cl)=CC(C)=C1NC(=O)CC1CCCC1 HYHPENAHMAZITK-UHFFFAOYSA-N 0.000 description 1
- HPSQCKGKVCFDOI-UHFFFAOYSA-N n-[4-[[(5-chloropyridin-2-yl)amino]methyl]-2,6-dimethylphenyl]-2-cyclopentylacetamide Chemical compound C=1C(C)=C(NC(=O)CC2CCCC2)C(C)=CC=1CNC1=CC=C(Cl)C=N1 HPSQCKGKVCFDOI-UHFFFAOYSA-N 0.000 description 1
- XETNUEHTWCZNAQ-UHFFFAOYSA-N n-[4-[[6-(4-cyanophenoxy)pyridin-3-yl]methylamino]-2-methylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(C)=CC=1NCC(C=N1)=CC=C1OC1=CC=C(C#N)C=C1 XETNUEHTWCZNAQ-UHFFFAOYSA-N 0.000 description 1
- CXLNABRKNCFEPE-UHFFFAOYSA-N n-[4-amino-6-methyl-2-[[4-(trifluoromethyl)phenyl]methylamino]pyrimidin-5-yl]-2-(3-chlorophenyl)acetamide Chemical compound N=1C(N)=C(NC(=O)CC=2C=C(Cl)C=CC=2)C(C)=NC=1NCC1=CC=C(C(F)(F)F)C=C1 CXLNABRKNCFEPE-UHFFFAOYSA-N 0.000 description 1
- XVSOQDVGOHMGII-UHFFFAOYSA-N n-[4-amino-6-methyl-2-[[4-(trifluoromethyl)phenyl]methylamino]pyrimidin-5-yl]-2-(4-fluorophenyl)acetamide Chemical compound N=1C(N)=C(NC(=O)CC=2C=CC(F)=CC=2)C(C)=NC=1NCC1=CC=C(C(F)(F)F)C=C1 XVSOQDVGOHMGII-UHFFFAOYSA-N 0.000 description 1
- MADIUWVCWDQSFO-UHFFFAOYSA-N n-[4-amino-6-methyl-2-[[4-(trifluoromethyl)phenyl]methylamino]pyrimidin-5-yl]-2-cyclopentylacetamide Chemical compound N=1C(N)=C(NC(=O)CC2CCCC2)C(C)=NC=1NCC1=CC=C(C(F)(F)F)C=C1 MADIUWVCWDQSFO-UHFFFAOYSA-N 0.000 description 1
- OSWHOUIOMBVTRL-UHFFFAOYSA-N n-[4-amino-6-methyl-2-[[4-(trifluoromethyl)phenyl]methylamino]pyrimidin-5-yl]hexanamide Chemical compound N1=C(N)C(NC(=O)CCCCC)=C(C)N=C1NCC1=CC=C(C(F)(F)F)C=C1 OSWHOUIOMBVTRL-UHFFFAOYSA-N 0.000 description 1
- WMITZKMKKZVUOA-UHFFFAOYSA-N n-[6-amino-1-[(4-fluorophenyl)methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1=2C=C(N)C(NC(=O)CC(C)(C)C)=CC=2CCN1CC1=CC=C(F)C=C1 WMITZKMKKZVUOA-UHFFFAOYSA-N 0.000 description 1
- PFXGSJZQUMCENI-UHFFFAOYSA-N n-[6-amino-1-[[3-fluoro-4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1=2C=C(N)C(NC(=O)CC(C)(C)C)=CC=2CCN1CC1=CC=C(C(F)(F)F)C(F)=C1 PFXGSJZQUMCENI-UHFFFAOYSA-N 0.000 description 1
- LEAGGTMYQUKNJZ-UHFFFAOYSA-N n-[6-amino-1-[[4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-2-(4-fluorophenyl)acetamide Chemical compound C1CC=2C=C(NC(=O)CC=3C=CC(F)=CC=3)C(N)=CC=2N1CC1=CC=C(C(F)(F)F)C=C1 LEAGGTMYQUKNJZ-UHFFFAOYSA-N 0.000 description 1
- IAZYLAOKVSTMMF-UHFFFAOYSA-N n-[6-amino-1-[[4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1=2C=C(N)C(NC(=O)CC(C)(C)C)=CC=2CCN1CC1=CC=C(C(F)(F)F)C=C1 IAZYLAOKVSTMMF-UHFFFAOYSA-N 0.000 description 1
- SJZUZZGCSNZQTD-UHFFFAOYSA-N n-[6-bromo-1-[(5-chlorothiophen-2-yl)methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1=2C=C(Br)C(NC(=O)CC(C)(C)C)=CC=2CCN1CC1=CC=C(Cl)S1 SJZUZZGCSNZQTD-UHFFFAOYSA-N 0.000 description 1
- ZAXBJTRAIGCMSW-UHFFFAOYSA-N n-[6-bromo-1-[[4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1=2C=C(Br)C(NC(=O)CC(C)(C)C)=CC=2CCN1CC1=CC=C(C(F)(F)F)C=C1 ZAXBJTRAIGCMSW-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000005071 nonynyl group Chemical group C(#CCCCCCCC)* 0.000 description 1
- 230000002474 noradrenergic effect Effects 0.000 description 1
- 229950010634 ocaperidone Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- QXFHPLPMTXEJPV-UHFFFAOYSA-N octane-1-sulfonic acid;sodium Chemical compound [Na].CCCCCCCCS(O)(=O)=O QXFHPLPMTXEJPV-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 210000000287 oocyte Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960002841 oxypertine Drugs 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
- 229960001057 paliperidone Drugs 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 208000002851 paranoid schizophrenia Diseases 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229960004505 penfluridol Drugs 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 1
- 229960002195 perazine Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- LUALIOATIOESLM-UHFFFAOYSA-N periciazine Chemical compound C1CC(O)CCN1CCCN1C2=CC(C#N)=CC=C2SC2=CC=CC=C21 LUALIOATIOESLM-UHFFFAOYSA-N 0.000 description 1
- 229960000769 periciazine Drugs 0.000 description 1
- 229960000762 perphenazine Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- QYNJALBPNQXKOG-UHFFFAOYSA-N phenyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C=CC=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QYNJALBPNQXKOG-UHFFFAOYSA-N 0.000 description 1
- 229940067631 phospholipid Drugs 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- YVUQSNJEYSNKRX-UHFFFAOYSA-N pimozide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 YVUQSNJEYSNKRX-UHFFFAOYSA-N 0.000 description 1
- 229960003634 pimozide Drugs 0.000 description 1
- AXKPFOAXAHJUAG-UHFFFAOYSA-N pipamperone Chemical compound C1CC(C(=O)N)(N2CCCCC2)CCN1CCCC(=O)C1=CC=C(F)C=C1 AXKPFOAXAHJUAG-UHFFFAOYSA-N 0.000 description 1
- 229960002776 pipamperone Drugs 0.000 description 1
- JOMHSQGEWSNUKU-UHFFFAOYSA-N pipotiazine Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCC(CCO)CC1 JOMHSQGEWSNUKU-UHFFFAOYSA-N 0.000 description 1
- 229960003252 pipotiazine Drugs 0.000 description 1
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- YGKUEOZJFIXDGI-UHFFFAOYSA-N pridopidine Chemical compound C1CN(CCC)CCC1C1=CC=CC(S(C)(=O)=O)=C1 YGKUEOZJFIXDGI-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 1
- 229960003111 prochlorperazine Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 210000001176 projection neuron Anatomy 0.000 description 1
- 229960003598 promazine Drugs 0.000 description 1
- MXUJFQOMTXBKEL-UHFFFAOYSA-N propan-2-yl n-[4-[(5-bromothiophen-2-yl)methylamino]-2-methoxyphenyl]carbamate Chemical compound C1=C(NC(=O)OC(C)C)C(OC)=CC(NCC=2SC(Br)=CC=2)=C1 MXUJFQOMTXBKEL-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- JRUNPSYYKOZIFI-UHFFFAOYSA-N propyl n-[2,6-dimethyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=C(C)C=C1NCC1=CC=C(C(F)(F)F)C=C1 JRUNPSYYKOZIFI-UHFFFAOYSA-N 0.000 description 1
- QHMVGVWNQLCEIC-UHFFFAOYSA-N propyl n-[2-bromo-4-[(4-methylsulfanylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(Br)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(SC)C=C1 QHMVGVWNQLCEIC-UHFFFAOYSA-N 0.000 description 1
- CSVKGTLKBFHNBH-UHFFFAOYSA-N propyl n-[2-bromo-4-[(4-tert-butylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(Br)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(C)(C)C)C=C1 CSVKGTLKBFHNBH-UHFFFAOYSA-N 0.000 description 1
- RDVVIESVSGRXJS-UHFFFAOYSA-N propyl n-[2-bromo-4-[(5-bromothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(Br)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(Br)S1 RDVVIESVSGRXJS-UHFFFAOYSA-N 0.000 description 1
- RFBPNVJIXZBIRC-UHFFFAOYSA-N propyl n-[2-bromo-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(Br)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(Cl)S1 RFBPNVJIXZBIRC-UHFFFAOYSA-N 0.000 description 1
- UJYLUVNQOIWRHI-UHFFFAOYSA-N propyl n-[2-bromo-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(Br)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(Cl)S1 UJYLUVNQOIWRHI-UHFFFAOYSA-N 0.000 description 1
- ZVJQBZOVZAKHCL-UHFFFAOYSA-N propyl n-[2-bromo-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]carbamate Chemical compound C1=C(Br)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 ZVJQBZOVZAKHCL-UHFFFAOYSA-N 0.000 description 1
- FJOCXCMSKXJZSK-UHFFFAOYSA-N propyl n-[2-bromo-4-[methyl-[(4-propan-2-ylphenyl)methyl]amino]phenyl]carbamate Chemical compound C1=C(Br)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(C(C)C)C=C1 FJOCXCMSKXJZSK-UHFFFAOYSA-N 0.000 description 1
- CYWFLRNPZAOFSD-UHFFFAOYSA-N propyl n-[2-chloro-4-[(4-fluorophenyl)methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(F)C=C1 CYWFLRNPZAOFSD-UHFFFAOYSA-N 0.000 description 1
- HMQPLANFTAPTBN-UHFFFAOYSA-N propyl n-[2-cyano-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]carbamate Chemical compound C1=C(C#N)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 HMQPLANFTAPTBN-UHFFFAOYSA-N 0.000 description 1
- CPKOTQLROKZIHS-UHFFFAOYSA-N propyl n-[2-cyano-4-[methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]phenyl]carbamate Chemical compound C1=C(C#N)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(C(F)(F)F)C=C1 CPKOTQLROKZIHS-UHFFFAOYSA-N 0.000 description 1
- BXPLVYLJBOHLAC-UHFFFAOYSA-N propyl n-[2-iodo-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(I)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 BXPLVYLJBOHLAC-UHFFFAOYSA-N 0.000 description 1
- FNIFMWOIQHIEBH-UHFFFAOYSA-N propyl n-[2-iodo-4-[[4-(4-methylpiperazin-1-yl)phenyl]methylamino]phenyl]carbamate Chemical compound C1=C(I)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(N2CCN(C)CC2)C=C1 FNIFMWOIQHIEBH-UHFFFAOYSA-N 0.000 description 1
- RJBCLHKMVOWSML-UHFFFAOYSA-N propyl n-[2-methoxy-4-[methyl-[(5-methylthiophen-2-yl)methyl]amino]phenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(C)S1 RJBCLHKMVOWSML-UHFFFAOYSA-N 0.000 description 1
- VACFMSSWACPZHI-UHFFFAOYSA-N propyl n-[2-methyl-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 VACFMSSWACPZHI-UHFFFAOYSA-N 0.000 description 1
- AAPHGYAVTQDBAX-UHFFFAOYSA-N propyl n-[2-methyl-4-[(5-methylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C)S1 AAPHGYAVTQDBAX-UHFFFAOYSA-N 0.000 description 1
- QVCSVXPJFKCBPU-UHFFFAOYSA-N propyl n-[2-methyl-4-[(5-phenylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C=2C=CC=CC=2)S1 QVCSVXPJFKCBPU-UHFFFAOYSA-N 0.000 description 1
- PINFNGLHVSTBBG-UHFFFAOYSA-N propyl n-[2-methyl-4-[methyl-[(4-methylsulfanylphenyl)methyl]amino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(SC)C=C1 PINFNGLHVSTBBG-UHFFFAOYSA-N 0.000 description 1
- UZUYYMCKQDLORF-UHFFFAOYSA-N propyl n-[2-phenyl-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(C=2C=CC=CC=2)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 UZUYYMCKQDLORF-UHFFFAOYSA-N 0.000 description 1
- CUZJSPJHSHZBAK-UHFFFAOYSA-N propyl n-[4-(1-benzofuran-2-ylmethylamino)-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCCC)=CC=C1NCC1=CC2=CC=CC=C2O1 CUZJSPJHSHZBAK-UHFFFAOYSA-N 0.000 description 1
- NPXGSEYMDJBGGG-UHFFFAOYSA-N propyl n-[4-(1-benzofuran-2-ylmethylamino)-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=CC2=CC=CC=C2O1 NPXGSEYMDJBGGG-UHFFFAOYSA-N 0.000 description 1
- UIDDHJYOJQKCBL-UHFFFAOYSA-N propyl n-[4-[(3,5-difluoroanilino)methyl]-2,6-dimethylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=C(C)C=C1CNC1=CC(F)=CC(F)=C1 UIDDHJYOJQKCBL-UHFFFAOYSA-N 0.000 description 1
- FCHLJBHFHBTVKP-UHFFFAOYSA-N propyl n-[4-[(4-fluorophenyl)methyl-methylamino]-2-methoxyphenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(F)C=C1 FCHLJBHFHBTVKP-UHFFFAOYSA-N 0.000 description 1
- SMJVYXBKVNPKMX-UHFFFAOYSA-N propyl n-[4-[(4-fluorophenyl)methylamino]-2,6-dimethylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=C(C)C=C1NCC1=CC=C(F)C=C1 SMJVYXBKVNPKMX-UHFFFAOYSA-N 0.000 description 1
- ZUMWFZLNACCXQY-UHFFFAOYSA-N propyl n-[4-[(4-fluorophenyl)methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(F)C=C1 ZUMWFZLNACCXQY-UHFFFAOYSA-N 0.000 description 1
- LFRNMSVOMBZWHX-UHFFFAOYSA-N propyl n-[4-[(4-fluorophenyl)methylamino]-2-phenylphenyl]carbamate Chemical compound C1=C(C=2C=CC=CC=2)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(F)C=C1 LFRNMSVOMBZWHX-UHFFFAOYSA-N 0.000 description 1
- WCEIYJJKLZBVFS-UHFFFAOYSA-N propyl n-[4-[(4-methylsulfanylphenyl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(SC)C=C1 WCEIYJJKLZBVFS-UHFFFAOYSA-N 0.000 description 1
- OAYSXZNFPMSWAG-UHFFFAOYSA-N propyl n-[4-[(4-tert-butylphenyl)methyl-methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(C(C)(C)C)C=C1 OAYSXZNFPMSWAG-UHFFFAOYSA-N 0.000 description 1
- GNWHHFNXSDFJRR-UHFFFAOYSA-N propyl n-[4-[(4-tert-butylphenyl)methyl-methylamino]-2-cyanophenyl]carbamate Chemical compound C1=C(C#N)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(C(C)(C)C)C=C1 GNWHHFNXSDFJRR-UHFFFAOYSA-N 0.000 description 1
- SIEUTMUKGSAJCV-UHFFFAOYSA-N propyl n-[4-[(4-tert-butylphenyl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(C)(C)C)C=C1 SIEUTMUKGSAJCV-UHFFFAOYSA-N 0.000 description 1
- HBJYCGYONGRNBT-UHFFFAOYSA-N propyl n-[4-[(4-tert-butylphenyl)methylamino]-2-iodophenyl]carbamate Chemical compound C1=C(I)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(C)(C)C)C=C1 HBJYCGYONGRNBT-UHFFFAOYSA-N 0.000 description 1
- UHEROFPUOURMRS-UHFFFAOYSA-N propyl n-[4-[(5-bromothiophen-2-yl)methyl-methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(Br)S1 UHEROFPUOURMRS-UHFFFAOYSA-N 0.000 description 1
- PCQHVHNZUALPAY-UHFFFAOYSA-N propyl n-[4-[(5-bromothiophen-2-yl)methyl-methylamino]-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(Br)S1 PCQHVHNZUALPAY-UHFFFAOYSA-N 0.000 description 1
- FWDZPVMNVYWYDE-UHFFFAOYSA-N propyl n-[4-[(5-bromothiophen-2-yl)methyl-methylamino]-2-cyanophenyl]carbamate Chemical compound C1=C(C#N)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(Br)S1 FWDZPVMNVYWYDE-UHFFFAOYSA-N 0.000 description 1
- YQQGBVKAOAIQCU-UHFFFAOYSA-N propyl n-[4-[(5-bromothiophen-2-yl)methyl-methylamino]-2-methoxyphenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(Br)S1 YQQGBVKAOAIQCU-UHFFFAOYSA-N 0.000 description 1
- CUWJGDXDNIVHMT-UHFFFAOYSA-N propyl n-[4-[(5-bromothiophen-2-yl)methyl-methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(Br)S1 CUWJGDXDNIVHMT-UHFFFAOYSA-N 0.000 description 1
- VNMZPITYDDGRFI-UHFFFAOYSA-N propyl n-[4-[(5-bromothiophen-2-yl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(Br)S1 VNMZPITYDDGRFI-UHFFFAOYSA-N 0.000 description 1
- BYUTZEHIGCHKBV-UHFFFAOYSA-N propyl n-[4-[(5-bromothiophen-2-yl)methylamino]-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(Br)S1 BYUTZEHIGCHKBV-UHFFFAOYSA-N 0.000 description 1
- NFJFMYAGECOXQG-UHFFFAOYSA-N propyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2,6-dimethylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=C(C)C=C1NCC1=CC=C(Cl)S1 NFJFMYAGECOXQG-UHFFFAOYSA-N 0.000 description 1
- PMQZVDCJFUVTHF-UHFFFAOYSA-N propyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-(furan-2-yl)phenyl]carbamate Chemical compound C1=C(C=2OC=CC=2)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(Cl)S1 PMQZVDCJFUVTHF-UHFFFAOYSA-N 0.000 description 1
- JTBGMUOYQQVBTC-UHFFFAOYSA-N propyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(Cl)S1 JTBGMUOYQQVBTC-UHFFFAOYSA-N 0.000 description 1
- HXYZXAFZZIRHHL-UHFFFAOYSA-N propyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-phenylphenyl]carbamate Chemical compound C1=C(C=2C=CC=CC=2)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(Cl)S1 HXYZXAFZZIRHHL-UHFFFAOYSA-N 0.000 description 1
- AANRTTWSJLIBNU-UHFFFAOYSA-N propyl n-[4-[(5-chlorothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCC)=CC=C1NCC1=CC=C(Cl)S1 AANRTTWSJLIBNU-UHFFFAOYSA-N 0.000 description 1
- NUTZCWRUFKZYLV-UHFFFAOYSA-N propyl n-[4-[(6-methoxy-1-benzothiophen-2-yl)methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=CC2=CC=C(OC)C=C2S1 NUTZCWRUFKZYLV-UHFFFAOYSA-N 0.000 description 1
- YGACWVPIOXYFMJ-UHFFFAOYSA-N propyl n-[4-[1-benzothiophen-2-ylmethyl(methyl)amino]-2-methoxyphenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC2=CC=CC=C2S1 YGACWVPIOXYFMJ-UHFFFAOYSA-N 0.000 description 1
- NEHSTGIZKPRPQM-UHFFFAOYSA-N propyl n-[4-[[3-fluoro-4-(trifluoromethyl)phenyl]methylamino]-2,6-dimethylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=C(C)C=C1NCC1=CC=C(C(F)(F)F)C(F)=C1 NEHSTGIZKPRPQM-UHFFFAOYSA-N 0.000 description 1
- PXPOVHBJPNEAIO-UHFFFAOYSA-N propyl n-[4-[[4-(4-chlorophenyl)sulfonyl-3-methylthiophen-2-yl]methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=C(C)C(S(=O)(=O)C=2C=CC(Cl)=CC=2)=CS1 PXPOVHBJPNEAIO-UHFFFAOYSA-N 0.000 description 1
- BXBONVDXYZLIRH-UHFFFAOYSA-N propyl n-[4-[[5-(dimethylamino)-3-methyl-1-benzothiophen-2-yl]methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=C(C)C2=CC(N(C)C)=CC=C2S1 BXBONVDXYZLIRH-UHFFFAOYSA-N 0.000 description 1
- PKMRTAMQCXTVMS-UHFFFAOYSA-N propyl n-[4-[[7-(dimethylamino)-1-benzothiophen-2-yl]methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=CC2=CC=CC(N(C)C)=C2S1 PKMRTAMQCXTVMS-UHFFFAOYSA-N 0.000 description 1
- GKFDLOMGRKRKCN-UHFFFAOYSA-N propyl n-[4-[methyl-[(4-methylsulfanylphenyl)methyl]amino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(SC)C=C1 GKFDLOMGRKRKCN-UHFFFAOYSA-N 0.000 description 1
- XJPFACYFAMERDR-UHFFFAOYSA-N propyl n-[4-[methyl-[(4-propan-2-ylphenyl)methyl]amino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(C(C)C)C=C1 XJPFACYFAMERDR-UHFFFAOYSA-N 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 229960000957 prothipendyl Drugs 0.000 description 1
- JTTAUPUMOLRVRA-UHFFFAOYSA-N prothipendyl Chemical group C1=CN=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 JTTAUPUMOLRVRA-UHFFFAOYSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 229960003448 remoxipride Drugs 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000036390 resting membrane potential Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- QXUAYTHTYPXRJX-UHFFFAOYSA-N s-ethyl n-[2-cyclopentyloxy-4-[(4-fluorophenyl)methyl-methylamino]phenyl]carbamothioate Chemical compound CCSC(=O)NC1=CC=C(N(C)CC=2C=CC(F)=CC=2)C=C1OC1CCCC1 QXUAYTHTYPXRJX-UHFFFAOYSA-N 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 230000018448 secretion by cell Effects 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 1
- 229960000652 sertindole Drugs 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- 230000003997 social interaction Effects 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 210000003523 substantia nigra Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229960004940 sulpiride Drugs 0.000 description 1
- 229960004724 sultopride Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229950011332 talnetant Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- WHVIPUKUBIQKNK-UHFFFAOYSA-N tert-butyl n-[1-[(5-chlorothiophen-2-yl)methyl]-2,3-dihydroindol-5-yl]carbamate Chemical compound C1CC2=CC(NC(=O)OC(C)(C)C)=CC=C2N1CC1=CC=C(Cl)S1 WHVIPUKUBIQKNK-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
- AIUHRQHVWSUTGJ-UHFFFAOYSA-N thiopropazate Chemical compound C1CN(CCOC(=O)C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 AIUHRQHVWSUTGJ-UHFFFAOYSA-N 0.000 description 1
- 229960004728 thiopropazate Drugs 0.000 description 1
- 229960003397 thioproperazine Drugs 0.000 description 1
- VZYCZNZBPPHOFY-UHFFFAOYSA-N thioproperazine Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCN(C)CC1 VZYCZNZBPPHOFY-UHFFFAOYSA-N 0.000 description 1
- 229960002784 thioridazine Drugs 0.000 description 1
- 229960005344 tiapride Drugs 0.000 description 1
- 229960005013 tiotixene Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
- 229960002324 trifluoperazine Drugs 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- GPMXUUPHFNMNDH-UHFFFAOYSA-N trifluperidol Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1CCCC(=O)C1=CC=C(F)C=C1 GPMXUUPHFNMNDH-UHFFFAOYSA-N 0.000 description 1
- 229960002341 trifluperidol Drugs 0.000 description 1
- XSCGXQMFQXDFCW-UHFFFAOYSA-N triflupromazine Chemical compound C1=C(C(F)(F)F)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 XSCGXQMFQXDFCW-UHFFFAOYSA-N 0.000 description 1
- 229960003904 triflupromazine Drugs 0.000 description 1
- 210000004496 type 1 vestibular hair cell Anatomy 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 229960001968 veralipride Drugs 0.000 description 1
- RYJXBGGBZJGVQF-UHFFFAOYSA-N veralipride Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(=O)NCC2N(CCC2)CC=C)=C1OC RYJXBGGBZJGVQF-UHFFFAOYSA-N 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 230000001720 vestibular Effects 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
- HDOZVRUNCMBHFH-UHFFFAOYSA-N zotepine Chemical compound CN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C12 HDOZVRUNCMBHFH-UHFFFAOYSA-N 0.000 description 1
- 229960004496 zotepine Drugs 0.000 description 1
- 229960004141 zuclopenthixol Drugs 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77130406P | 2006-02-07 | 2006-02-07 | |
| DKPA200600175 | 2006-02-07 | ||
| PCT/DK2007/050013 WO2007090409A1 (en) | 2006-02-07 | 2007-02-02 | Use of kcnq-openers for threating or reducing the symptoms of schizophrenia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ569517A true NZ569517A (en) | 2011-07-29 |
Family
ID=38055396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ569517A NZ569517A (en) | 2006-02-07 | 2007-02-02 | Use of KCNQ-openers for threating or reducing the symptoms of schizophrenia |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20090118285A1 (enExample) |
| EP (2) | EP2554162A1 (enExample) |
| JP (1) | JP2009525993A (enExample) |
| KR (1) | KR20080096659A (enExample) |
| CN (1) | CN101378742B (enExample) |
| AR (1) | AR059319A1 (enExample) |
| AU (1) | AU2007214128B2 (enExample) |
| BR (1) | BRPI0707495A2 (enExample) |
| CA (1) | CA2641564C (enExample) |
| EA (1) | EA017915B1 (enExample) |
| IL (1) | IL192745A0 (enExample) |
| MX (1) | MX2008009655A (enExample) |
| NO (1) | NO20083838L (enExample) |
| NZ (1) | NZ569517A (enExample) |
| TW (1) | TWI453013B (enExample) |
| WO (1) | WO2007090409A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011513196A (ja) * | 2007-08-01 | 2011-04-28 | ハー・ルンドベック・アクチエゼルスカベット | ドーパミン作動系が破壊された障害もしくは状態の症状を軽減するためまたはその障害もしくは状態を処置するためのkcnqカリウムチャネル開口薬の使用 |
| CA2804165C (en) | 2010-07-08 | 2015-02-24 | Pfizer Inc. | Piperidinyl pyrimidine amides as kv7 potassium channel openers |
| WO2016077724A1 (en) * | 2014-11-13 | 2016-05-19 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | (2-amino-4(arylamino)phenyl) carbamates |
| US10590067B2 (en) | 2018-02-20 | 2020-03-17 | H. Lundbeck A/S | Alcohol derivatives of carboxamides as Kv7 potassium channel openers |
| MA51881B1 (fr) | 2018-02-20 | 2023-08-31 | H Lundbeck As | Dérivés d'alcool utilisés en tant qu'agents d'ouverture du canal potassique kv7 |
| WO2019203951A1 (en) | 2018-04-20 | 2019-10-24 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Selective potassium channel agonists |
| RS66130B1 (sr) | 2019-08-02 | 2024-11-29 | H Lundbeck As | Derivati alkohola kao otvarači kv7 kalijumovih kanala |
| CN119490430A (zh) | 2019-08-02 | 2025-02-21 | H.隆德贝克有限公司 | 用于在癫痫或癫痫发作中使用的作为Kv7钾通道开放剂的醇衍生物 |
| AR119521A1 (es) | 2019-08-02 | 2021-12-22 | H Lundbeck As | DERIVADOS DE ALCOHOL COMO ABRIDORES DEL CANAL DE POTASIO Kv7 |
| US20230015539A1 (en) * | 2019-12-06 | 2023-01-19 | Icahn School Of Medicine At Mount Sinai | Method of treatment with kcnq channel openers |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4200259A1 (de) * | 1992-01-08 | 1993-07-15 | Asta Medica Ag | Neue 1,2,4-triaminobenzol-derivate und verfahren zu deren herstellung |
| JP4294142B2 (ja) | 1999-02-02 | 2009-07-08 | 株式会社日立製作所 | ディスクサブシステム |
| GB9915414D0 (en) * | 1999-07-01 | 1999-09-01 | Glaxo Group Ltd | Medical use |
| US6472165B1 (en) * | 1999-08-03 | 2002-10-29 | Arzneimittelwerk Dresden Gmbh | Modulatory binding site in potassium channels for screening and finding new active ingredients |
| US6495550B2 (en) * | 1999-08-04 | 2002-12-17 | Icagen, Inc. | Pyridine-substituted benzanilides as potassium ion channel openers |
| CA2438868A1 (en) * | 2001-02-20 | 2002-09-19 | Valentin K. Gribkoff | Modulators of kcnq potassium channels and use thereof in treating migraine and mechanistically related diseases |
| US6469042B1 (en) * | 2001-02-20 | 2002-10-22 | Bristol-Myers Squibb Company | Fluoro oxindole derivatives as modulators if KCNQ potassium channels |
| JP2004535413A (ja) * | 2001-05-31 | 2004-11-25 | ブリストル−マイヤーズ スクイブ カンパニー | Kcnqカリウムチャンネルモジュレーターとしてのシンナミド誘導体 |
| DE10228103A1 (de) | 2002-06-24 | 2004-01-15 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| AU2003294442A1 (en) * | 2002-11-22 | 2004-06-18 | Bristol-Myers Squibb Company | 3-heterocyclic benzylamide derivatives as potassium channel openers |
| US6933308B2 (en) * | 2002-12-20 | 2005-08-23 | Bristol-Myers Squibb Company | Aminoalkyl thiazole derivatives as KCNQ modulators |
| NZ540446A (en) * | 2002-12-27 | 2008-03-28 | Lundbeck & Co As H | 1,2,4-Triaminobenzene derivatives useful for treating disorders of the central nervous system |
| EP1603858A2 (en) * | 2003-03-11 | 2005-12-14 | NeuroSearch A/S | Kcnq channel modulating compounds and their pharmaceutical use |
| JP2006520333A (ja) * | 2003-03-14 | 2006-09-07 | ハー・ルンドベック・アクチエゼルスカベット | 置換されたアニリン誘導体 |
| AU2004222626B2 (en) * | 2003-03-21 | 2010-06-24 | H. Lundbeck A/S | Substituted p-diaminobenzene derivatives |
| EP1631546A1 (en) | 2003-04-25 | 2006-03-08 | H. Lundbeck A/S | Sustituted indoline and indole derivatives |
| US7563748B2 (en) | 2003-06-23 | 2009-07-21 | Cognis Ip Management Gmbh | Alcohol alkoxylate carriers for pesticide active ingredients |
| WO2005025293A2 (en) * | 2003-09-10 | 2005-03-24 | Icagen, Inc. | Fused ring heterocycles as potassium channel modulators |
| ATE423128T1 (de) * | 2004-02-20 | 2009-03-15 | Nat Ct For Biolog Sciences | Neues kaliumkanalmodulierendes peptid |
| TWI349666B (en) * | 2004-03-12 | 2011-10-01 | Lundbeck & Co As H | Substituted morpholine and thiomorpholine derivatives |
| WO2006000020A1 (en) | 2004-06-29 | 2006-01-05 | European Nickel Plc | Improved leaching of base metals |
| UA89503C2 (uk) * | 2004-09-13 | 2010-02-10 | Х. Луннбек А/С | Заміщені похідні аніліну |
| US7812020B2 (en) * | 2005-03-03 | 2010-10-12 | H. Lundbeck A/S | Substituted pyridine derivatives |
| WO2007063418A2 (en) * | 2005-04-13 | 2007-06-07 | Neuraxon, Inc. | Substituted indole compounds having nos inhibitory activity |
-
2007
- 2007-02-02 EP EP12190206A patent/EP2554162A1/en not_active Withdrawn
- 2007-02-02 EP EP07702527A patent/EP1983974A1/en not_active Withdrawn
- 2007-02-02 BR BRPI0707495-6A patent/BRPI0707495A2/pt not_active IP Right Cessation
- 2007-02-02 JP JP2008553621A patent/JP2009525993A/ja not_active Ceased
- 2007-02-02 CA CA2641564A patent/CA2641564C/en not_active Expired - Fee Related
- 2007-02-02 KR KR1020087019396A patent/KR20080096659A/ko not_active Ceased
- 2007-02-02 AU AU2007214128A patent/AU2007214128B2/en not_active Ceased
- 2007-02-02 TW TW096103826A patent/TWI453013B/zh not_active IP Right Cessation
- 2007-02-02 CN CN2007800046484A patent/CN101378742B/zh not_active Expired - Fee Related
- 2007-02-02 EA EA200870232A patent/EA017915B1/ru not_active IP Right Cessation
- 2007-02-02 WO PCT/DK2007/050013 patent/WO2007090409A1/en not_active Ceased
- 2007-02-02 MX MX2008009655A patent/MX2008009655A/es active IP Right Grant
- 2007-02-02 NZ NZ569517A patent/NZ569517A/en not_active IP Right Cessation
- 2007-02-02 US US12/278,394 patent/US20090118285A1/en not_active Abandoned
- 2007-02-05 AR ARP070100469A patent/AR059319A1/es not_active Application Discontinuation
-
2008
- 2008-07-10 IL IL192745A patent/IL192745A0/en unknown
- 2008-09-05 NO NO20083838A patent/NO20083838L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2554162A1 (en) | 2013-02-06 |
| AR059319A1 (es) | 2008-03-26 |
| EA200870232A1 (ru) | 2009-02-27 |
| IL192745A0 (en) | 2009-02-11 |
| AU2007214128B2 (en) | 2012-05-17 |
| JP2009525993A (ja) | 2009-07-16 |
| CN101378742B (zh) | 2013-07-10 |
| EA017915B1 (ru) | 2013-04-30 |
| CN101378742A (zh) | 2009-03-04 |
| MX2008009655A (es) | 2008-09-03 |
| CA2641564C (en) | 2012-06-12 |
| TWI453013B (zh) | 2014-09-21 |
| US20090118285A1 (en) | 2009-05-07 |
| KR20080096659A (ko) | 2008-10-31 |
| TW200808296A (en) | 2008-02-16 |
| NO20083838L (no) | 2008-10-31 |
| BRPI0707495A2 (pt) | 2011-05-03 |
| EP1983974A1 (en) | 2008-10-29 |
| CA2641564A1 (en) | 2007-08-16 |
| AU2007214128A1 (en) | 2007-08-16 |
| WO2007090409A1 (en) | 2007-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20100256145A1 (en) | Use of kcnq potassium channel openers for reducing symptoms of or treating disorders or conditions wherein the dopaminergic system is disrupted | |
| CA2641564C (en) | Use of kcnq-openers for treating or reducing the symptoms of schizophrenia | |
| JP7781768B2 (ja) | 神経学的および精神障害の治療方法 | |
| JP5907975B2 (ja) | 運動障害の治療のためのセロトニン受容体アゴニストの組み合わせ | |
| JP2021181465A (ja) | レム睡眠行動障害の予防および処置のために有用なジアリールおよびアリールヘテロアリール尿素誘導体 | |
| US20180271869A1 (en) | Treatment of anxiety disorders and autism spectrum disorders | |
| EP2298766A1 (en) | Substituted pyridine derivatives | |
| US20220096444A1 (en) | Prophylactic or therapeutic agent for delirium | |
| WO2013004249A1 (en) | The use of serotonin receptor agonists for treatment of movement disorders | |
| US20050119285A1 (en) | Treatment of neurological disorders related to rapid eye movement (REM) sleep disturbances with NPY Y5 receptor antagonists | |
| HK1181676A (en) | Use of kcnq-openers for treating or reducing the symptoms of schizophrenia | |
| HK1129593A1 (en) | Use of kcnq-opener for the preparation of a pharmaceutical composition for treating schizophrenia | |
| HK1129593B (en) | Use of kcnq-opener for the preparation of a pharmaceutical composition for treating schizophrenia | |
| AU2010246724B2 (en) | Stable forms of N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-3,3-dimethyl- butyramide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |