CA2909633A1 - Pharmaceutical composition comprising an ampk activator and a serotonergic agent and methods of use thereof - Google Patents
Pharmaceutical composition comprising an ampk activator and a serotonergic agent and methods of use thereofInfo
- Publication number
- CA2909633A1 CA2909633A1 CA2909633A CA2909633A CA2909633A1 CA 2909633 A1 CA2909633 A1 CA 2909633A1 CA 2909633 A CA2909633 A CA 2909633A CA 2909633 A CA2909633 A CA 2909633A CA 2909633 A1 CA2909633 A1 CA 2909633A1
- Authority
- CA
- Canada
- Prior art keywords
- acetamide
- piperidin
- fluorobenzyl
- ethyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 107
- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 36
- MPLLLQUZNJSVTK-UHFFFAOYSA-N 5-[3-[4-[2-(4-fluorophenyl)ethoxy]phenyl]propyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1CCCC(C=C1)=CC=C1OCCC1=CC=C(F)C=C1 MPLLLQUZNJSVTK-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 230000000862 serotonergic effect Effects 0.000 title claims description 32
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 96
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 63
- 239000000203 mixture Substances 0.000 claims abstract description 58
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 58
- 201000010099 disease Diseases 0.000 claims abstract description 48
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 claims abstract description 34
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229960003987 melatonin Drugs 0.000 claims abstract description 34
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin hydrochloride Natural products CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims abstract description 33
- 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 20
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 20
- 229940076279 serotonin Drugs 0.000 claims abstract description 19
- 201000011510 cancer Diseases 0.000 claims abstract description 16
- 230000000694 effects Effects 0.000 claims abstract description 9
- 229960004329 metformin hydrochloride Drugs 0.000 claims abstract description 8
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 claims abstract description 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 195
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 144
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 80
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 64
- -1 corlumidin Chemical compound 0.000 claims description 60
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 53
- 229940095064 tartrate Drugs 0.000 claims description 53
- DUUGKQCEGZLZNO-UHFFFAOYSA-N 5-hydroxyindoleacetic acid Chemical compound C1=C(O)C=C2C(CC(=O)O)=CNC2=C1 DUUGKQCEGZLZNO-UHFFFAOYSA-N 0.000 claims description 52
- 239000004202 carbamide Substances 0.000 claims description 49
- 150000001413 amino acids Chemical group 0.000 claims description 42
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 40
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 39
- 235000013877 carbamide Nutrition 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 31
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 claims description 27
- RVWZUOPFHTYIEO-UHFFFAOYSA-N 5-hydroxyindoleacetic acid Natural products C1=C(O)C=C2C(C(=O)O)=CNC2=C1 RVWZUOPFHTYIEO-UHFFFAOYSA-N 0.000 claims description 26
- 239000003310 5-hydroxyindoleacetic acid Substances 0.000 claims description 26
- 108010076365 Adiponectin Proteins 0.000 claims description 25
- 229960003105 metformin Drugs 0.000 claims description 25
- 229960004425 sibutramine Drugs 0.000 claims description 25
- MEVXSUZBFYZPHZ-UHFFFAOYSA-N 2-amino-3-methyl-4h-imidazol-5-one;sulfuric acid Chemical compound OS(O)(=O)=O.CN1CC(=O)N=C1N MEVXSUZBFYZPHZ-UHFFFAOYSA-N 0.000 claims description 24
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 102000011690 Adiponectin Human genes 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 20
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 18
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 claims description 17
- JTEJPPKMYBDEMY-UHFFFAOYSA-N 5-methoxytryptamine Chemical compound COC1=CC=C2NC=C(CCN)C2=C1 JTEJPPKMYBDEMY-UHFFFAOYSA-N 0.000 claims description 16
- 239000002207 metabolite Substances 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229940000681 5-hydroxytryptophan Drugs 0.000 claims description 14
- 208000030507 AIDS Diseases 0.000 claims description 14
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 14
- VRSRXLJTYQVOHC-YEJXKQKISA-N corydaline Chemical compound C=1([C@H]2[C@H]3C)C=C(OC)C(OC)=CC=1CCN2CC1=C3C=CC(OC)=C1OC VRSRXLJTYQVOHC-YEJXKQKISA-N 0.000 claims description 14
- 239000003112 inhibitor Substances 0.000 claims description 14
- 239000000651 prodrug Substances 0.000 claims description 14
- 229940002612 prodrug Drugs 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 13
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 13
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 claims description 13
- BMCZTYDZHNTKPR-MRXNPFEDSA-N (13ar)-2,9,10-trimethoxy-6,8,13,13a-tetrahydro-5h-isoquinolino[2,1-b]isoquinolin-3-ol Chemical compound C1C2=CC=C(OC)C(OC)=C2CN2[C@H]1C(C=C(C(=C1)O)OC)=C1CC2 BMCZTYDZHNTKPR-MRXNPFEDSA-N 0.000 claims description 12
- GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical class C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 claims description 12
- 102100022204 DNA-dependent protein kinase catalytic subunit Human genes 0.000 claims description 12
- 101710157074 DNA-dependent protein kinase catalytic subunit Proteins 0.000 claims description 12
- 229940123464 Thiazolidinedione Drugs 0.000 claims description 12
- 239000005557 antagonist Substances 0.000 claims description 12
- 239000000039 congener Substances 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims description 12
- 150000004702 methyl esters Chemical class 0.000 claims description 12
- 239000002243 precursor Substances 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 claims description 11
- QLOOWOVVZLBYHU-VIFPVBQESA-N (2s)-1-(7-ethylfuro[2,3-g]indazol-1-yl)propan-2-amine Chemical compound O1C(CC)=CC2=C1C=CC1=C2N(C[C@H](C)N)N=C1 QLOOWOVVZLBYHU-VIFPVBQESA-N 0.000 claims description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims description 11
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims description 11
- CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 claims description 11
- ZSTKHSQDNIGFLM-UHFFFAOYSA-N 5-methoxy-N,N-dimethyltryptamine Chemical compound COC1=CC=C2NC=C(CCN(C)C)C2=C1 ZSTKHSQDNIGFLM-UHFFFAOYSA-N 0.000 claims description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 10
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 10
- 208000032000 Glycogen storage disease due to muscle glycogen phosphorylase deficiency Diseases 0.000 claims description 10
- 206010018462 Glycogen storage disease type V Diseases 0.000 claims description 10
- 208000001132 Osteoporosis Diseases 0.000 claims description 10
- 208000018737 Parkinson disease Diseases 0.000 claims description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- 206010036049 Polycystic ovaries Diseases 0.000 claims description 10
- NWAJASRWXZETDW-UHFFFAOYSA-N acetamide;oxalic acid Chemical compound CC(N)=O.OC(=O)C(O)=O NWAJASRWXZETDW-UHFFFAOYSA-N 0.000 claims description 10
- 208000020450 carbohydrate metabolism disease Diseases 0.000 claims description 10
- 201000004534 glycogen storage disease V Diseases 0.000 claims description 10
- 201000001881 impotence Diseases 0.000 claims description 10
- 208000017745 inborn carbohydrate metabolic disease Diseases 0.000 claims description 10
- OPGPFZQBCIAFLI-UHFFFAOYSA-N obovatol Chemical compound OC1=CC(CC=C)=CC(OC=2C=CC(CC=C)=CC=2)=C1O OPGPFZQBCIAFLI-UHFFFAOYSA-N 0.000 claims description 10
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 10
- 239000003772 serotonin uptake inhibitor Substances 0.000 claims description 10
- 201000002859 sleep apnea Diseases 0.000 claims description 10
- 239000000021 stimulant Substances 0.000 claims description 10
- WTOYNNBCKUYIKC-JMSVASOKSA-N (+)-nootkatone Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 WTOYNNBCKUYIKC-JMSVASOKSA-N 0.000 claims description 9
- KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 claims description 9
- 229940097276 5-methoxytryptamine Drugs 0.000 claims description 9
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical compound O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 claims description 9
- ZBXDOQWPGBISAR-UHFFFAOYSA-N 6-methyl-2,3,4,5-tetrahydro-1H-azepino[4,5-b]indole Chemical compound C1CNCCC2=C1N(C)C1=CC=CC=C12 ZBXDOQWPGBISAR-UHFFFAOYSA-N 0.000 claims description 9
- RTRQQBHATOEIAF-UHFFFAOYSA-N AICA riboside Natural products NC1=C(C(=O)N)N=CN1C1C(O)C(O)C(CO)O1 RTRQQBHATOEIAF-UHFFFAOYSA-N 0.000 claims description 9
- 206010020772 Hypertension Diseases 0.000 claims description 9
- 208000008589 Obesity Diseases 0.000 claims description 9
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 claims description 9
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 9
- RTRQQBHATOEIAF-UUOKFMHZSA-N acadesine Chemical compound NC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 RTRQQBHATOEIAF-UUOKFMHZSA-N 0.000 claims description 9
- 230000009471 action Effects 0.000 claims description 9
- 229960004111 buformin Drugs 0.000 claims description 9
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 claims description 9
- 229960004606 clomipramine Drugs 0.000 claims description 9
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- WTOYNNBCKUYIKC-UHFFFAOYSA-N dl-nootkatone Natural products C1CC(C(C)=C)CC2(C)C(C)CC(=O)C=C21 WTOYNNBCKUYIKC-UHFFFAOYSA-N 0.000 claims description 9
- 235000020824 obesity Nutrition 0.000 claims description 9
- 229960003243 phenformin Drugs 0.000 claims description 9
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 claims description 9
- 229960005095 pioglitazone Drugs 0.000 claims description 9
- 235000021283 resveratrol Nutrition 0.000 claims description 9
- 229940016667 resveratrol Drugs 0.000 claims description 9
- 229960004586 rosiglitazone Drugs 0.000 claims description 9
- 150000001467 thiazolidinediones Chemical class 0.000 claims description 9
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 8
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 claims description 8
- ASXGJMSKWNBENU-UHFFFAOYSA-N 8-OH-DPAT Chemical compound C1=CC(O)=C2CC(N(CCC)CCC)CCC2=C1 ASXGJMSKWNBENU-UHFFFAOYSA-N 0.000 claims description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 8
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 8
- 102100026715 Serine/threonine-protein kinase STK11 Human genes 0.000 claims description 8
- 108020004459 Small interfering RNA Proteins 0.000 claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 8
- 229920001184 polypeptide Polymers 0.000 claims description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 8
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 8
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims description 8
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims description 8
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 claims description 7
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 claims description 7
- VRSRXLJTYQVOHC-UHFFFAOYSA-N Corydaline Natural products CC1C2C=3C=C(OC)C(OC)=CC=3CCN2CC2=C1C=CC(OC)=C2OC VRSRXLJTYQVOHC-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
- UMTDAKAAYOXIKU-HXUWFJFHSA-N (2s)-n-tert-butyl-3-[4-(2-methoxyphenyl)piperazin-1-yl]-2-phenylpropanamide Chemical compound COC1=CC=CC=C1N1CCN(C[C@@H](C(=O)NC(C)(C)C)C=2C=CC=CC=2)CC1 UMTDAKAAYOXIKU-HXUWFJFHSA-N 0.000 claims description 6
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 6
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 6
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 6
- XKFPYPQQHFEXRZ-UHFFFAOYSA-N 5-methyl-N'-(phenylmethyl)-3-isoxazolecarbohydrazide Chemical compound O1C(C)=CC(C(=O)NNCC=2C=CC=CC=2)=N1 XKFPYPQQHFEXRZ-UHFFFAOYSA-N 0.000 claims description 6
- XJLDYKIEURAVBW-UHFFFAOYSA-N Aethyl-heptyl-keton Natural products CCCCCCCC(=O)CC XJLDYKIEURAVBW-UHFFFAOYSA-N 0.000 claims description 6
- DMULVCHRPCFFGV-UHFFFAOYSA-N N,N-dimethyltryptamine Chemical compound C1=CC=C2C(CCN(C)C)=CNC2=C1 DMULVCHRPCFFGV-UHFFFAOYSA-N 0.000 claims description 6
- SBPRIAGPYFYCRT-UHFFFAOYSA-N N-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-N-(2-pyridinyl)cyclohexanecarboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2N=CC=CC=2)CC1 SBPRIAGPYFYCRT-UHFFFAOYSA-N 0.000 claims description 6
- DYYZXRCFCVDSKD-UHFFFAOYSA-N N6,N6-dimethyl-N4-[1-(phenylmethyl)-5-indazolyl]pyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 DYYZXRCFCVDSKD-UHFFFAOYSA-N 0.000 claims description 6
- SJDOMIRMMUGQQK-UHFFFAOYSA-N NAN 190 Chemical compound COC1=CC=CC=C1N1CCN(CCCCN2C(C3=CC=CC=C3C2=O)=O)CC1 SJDOMIRMMUGQQK-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 229940127236 atypical antipsychotics Drugs 0.000 claims description 6
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 claims description 6
- USRHYDPUVLEVMC-FQEVSTJZSA-N dapoxetine Chemical compound C1([C@H](CCOC=2C3=CC=CC=C3C=CC=2)N(C)C)=CC=CC=C1 USRHYDPUVLEVMC-FQEVSTJZSA-N 0.000 claims description 6
- PPRRDFIXUUSXRA-UHFFFAOYSA-N flibanserin Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CCN3C(NC4=CC=CC=C43)=O)CC2)=C1 PPRRDFIXUUSXRA-UHFFFAOYSA-N 0.000 claims description 6
- 230000014509 gene expression Effects 0.000 claims description 6
- 230000001965 increasing effect Effects 0.000 claims description 6
- SADQVAVFGNTEOD-UHFFFAOYSA-N indalpine Chemical compound C=1NC2=CC=CC=C2C=1CCC1CCNCC1 SADQVAVFGNTEOD-UHFFFAOYSA-N 0.000 claims description 6
- 229960002672 isocarboxazid Drugs 0.000 claims description 6
- PRZPXKIXNNNNCD-UHFFFAOYSA-N n-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]adamantane-1-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCCNC(=O)C23CC4CC(CC(C4)C2)C3)CC1 PRZPXKIXNNNNCD-UHFFFAOYSA-N 0.000 claims description 6
- SPWZXWDPAWDKQE-UHFFFAOYSA-N naluzotan Chemical compound CC(=O)NC1=CC=CC(N2CCN(CCCCNS(=O)(=O)CC3CCCCC3)CC2)=C1 SPWZXWDPAWDKQE-UHFFFAOYSA-N 0.000 claims description 6
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims description 6
- 239000004055 small Interfering RNA Substances 0.000 claims description 6
- 229960003708 sumatriptan Drugs 0.000 claims description 6
- VGKODZCNDHJSOX-UHFFFAOYSA-N trihydrate;tetrahydrochloride Chemical compound O.O.O.Cl.Cl.Cl.Cl VGKODZCNDHJSOX-UHFFFAOYSA-N 0.000 claims description 6
- AERLHOTUXIJQFV-RCPZPFRWSA-N zalospirone Chemical compound O=C([C@@H]1[C@@H]([C@@H]2C=C[C@H]1[C@H]1C=C[C@H]12)C1=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 AERLHOTUXIJQFV-RCPZPFRWSA-N 0.000 claims description 6
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 5
- QGRQJMXAQYGAKK-QMMMGPOBSA-N (2s)-1-(6-bromo-2,3-dihydroindol-1-yl)propan-2-amine Chemical compound C1=C(Br)C=C2N(C[C@@H](N)C)CCC2=C1 QGRQJMXAQYGAKK-QMMMGPOBSA-N 0.000 claims description 5
- FJRIVFVALIEIOY-VIFPVBQESA-N (2s)-1-(8,9-dihydro-7h-pyrano[2,3-g]indazol-1-yl)propan-2-amine Chemical compound O1CCCC2=C3N(C[C@@H](N)C)N=CC3=CC=C21 FJRIVFVALIEIOY-VIFPVBQESA-N 0.000 claims description 5
- BTTOYOKCLDAHHO-HNNXBMFYSA-N (2s)-n,n-dimethyl-5-(1,3,5-trimethylpyrazol-4-yl)-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C([C@@H](C1)N(C)C)CC2=C1C=CC=C2C=1C(C)=NN(C)C=1C BTTOYOKCLDAHHO-HNNXBMFYSA-N 0.000 claims description 5
- FNKBVTBXFLSTPB-LBPRGKRZSA-N (7s)-7-(dipropylamino)-4-fluoro-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1=CC(O)=C2C[C@@H](N(CCC)CCC)CCC2=C1F FNKBVTBXFLSTPB-LBPRGKRZSA-N 0.000 claims description 5
- QJPPEMXOOWNICQ-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-(2,3-dihydro-1h-inden-2-yl)piperazine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCN1C1CC2=CC=CC=C2C1 QJPPEMXOOWNICQ-UHFFFAOYSA-N 0.000 claims description 5
- FXMWUTGUCAKGQL-UHFFFAOYSA-N 2,5-dimethoxy-4-bromoamphetamine Chemical compound COC1=CC(CC(C)N)=C(OC)C=C1Br FXMWUTGUCAKGQL-UHFFFAOYSA-N 0.000 claims description 5
- ZEYRDXUWJDGTLD-UHFFFAOYSA-N 2-(2-ethyl-5-methoxy-1h-indol-3-yl)-n,n-dimethylethanamine Chemical compound C1=C(OC)C=C2C(CCN(C)C)=C(CC)NC2=C1 ZEYRDXUWJDGTLD-UHFFFAOYSA-N 0.000 claims description 5
- WYWNEDARFVJQSG-UHFFFAOYSA-N 2-methylserotonin Chemical compound C1=C(O)C=C2C(CCN)=C(C)NC2=C1 WYWNEDARFVJQSG-UHFFFAOYSA-N 0.000 claims description 5
- NJNMIPDEUMTYNV-UHFFFAOYSA-N 25i-nbmd Chemical compound C1=C(I)C(OC)=CC(CCNCC=2C=3OCOC=3C=CC=2)=C1OC NJNMIPDEUMTYNV-UHFFFAOYSA-N 0.000 claims description 5
- BYNFKPVCVMZGOI-UHFFFAOYSA-N 3-(2-aminoethyl)-1h-indol-5-ol;sulfuric acid Chemical compound OS([O-])(=O)=O.C1=C(O)C=C2C(CC[NH3+])=CNC2=C1 BYNFKPVCVMZGOI-UHFFFAOYSA-N 0.000 claims description 5
- LXFHSCDLMBZYKY-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-7-(trifluoromethyl)pyrrolo[1,2-a]quinoxaline Chemical compound C1CN(C)CCN1C1=NC2=CC(C(F)(F)F)=CC=C2N2C1=CC=C2 LXFHSCDLMBZYKY-UHFFFAOYSA-N 0.000 claims description 5
- WKZLNEWVIAGNAW-UHFFFAOYSA-N 5-Carboxyamidotryptamine Chemical compound C1=C(C(N)=O)C=C2C(CCN)=CNC2=C1 WKZLNEWVIAGNAW-UHFFFAOYSA-N 0.000 claims description 5
- VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims description 5
- WFZKRNIMSVDNBU-UHFFFAOYSA-N Creatinine sulfate mixture with serotonin Chemical compound [O-]S([O-])(=O)=O.C[NH+]1CC(=O)N=C1N.C1=C(O)C=C2C(CC[NH3+])=CNC2=C1 WFZKRNIMSVDNBU-UHFFFAOYSA-N 0.000 claims description 5
- MPJKWIXIYCLVCU-UHFFFAOYSA-N Folinic acid Natural products NC1=NC2=C(N(C=O)C(CNc3ccc(cc3)C(=O)NC(CCC(=O)O)CC(=O)O)CN2)C(=O)N1 MPJKWIXIYCLVCU-UHFFFAOYSA-N 0.000 claims description 5
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 5
- MDIGAZPGKJFIAH-UHFFFAOYSA-N Serotonin hydrochloride Chemical compound Cl.C1=C(O)C=C2C(CCN)=CNC2=C1 MDIGAZPGKJFIAH-UHFFFAOYSA-N 0.000 claims description 5
- ICMGLRUYEQNHPF-UHFFFAOYSA-N Uraprene Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2N(C(=O)N(C)C(=O)C=2)C)CC1 ICMGLRUYEQNHPF-UHFFFAOYSA-N 0.000 claims description 5
- 239000003288 aldose reductase inhibitor Substances 0.000 claims description 5
- 229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 claims description 5
- 150000004648 butanoic acid derivatives Chemical class 0.000 claims description 5
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims description 5
- 235000005487 catechin Nutrition 0.000 claims description 5
- WBYHTZYHAFNBKW-ZETCQYMHSA-N chembl371300 Chemical compound C1=C(O)C=C2N(C[C@@H](N)C)N=CC2=C1 WBYHTZYHAFNBKW-ZETCQYMHSA-N 0.000 claims description 5
- 229960001582 fenfluramine Drugs 0.000 claims description 5
- 229960002464 fluoxetine Drugs 0.000 claims description 5
- 229960004038 fluvoxamine Drugs 0.000 claims description 5
- 235000008191 folinic acid Nutrition 0.000 claims description 5
- VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 claims description 5
- 239000011672 folinic acid Substances 0.000 claims description 5
- 229960001691 leucovorin Drugs 0.000 claims description 5
- 230000000407 monoamine reuptake Effects 0.000 claims description 5
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims description 5
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 claims description 5
- 229960005017 olanzapine Drugs 0.000 claims description 5
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 5
- 229960002296 paroxetine Drugs 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 229940026197 serotonin hydrochloride Drugs 0.000 claims description 5
- 239000000952 serotonin receptor agonist Substances 0.000 claims description 5
- 230000013275 serotonin uptake Effects 0.000 claims description 5
- 229960002073 sertraline Drugs 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 claims description 4
- GKJZMAHZJGSBKD-NMMTYZSQSA-N (10E,12Z)-octadecadienoic acid Chemical compound CCCCC\C=C/C=C/CCCCCCCCC(O)=O GKJZMAHZJGSBKD-NMMTYZSQSA-N 0.000 claims description 4
- AEQDJSLRWYMAQI-QGZVFWFLSA-N (13ar)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5h-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3C[C@@H]2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-QGZVFWFLSA-N 0.000 claims description 4
- PTJADDMMFYXMMG-LJQANCHMSA-N (1r)-1-(4-fluorophenyl)-1-[3-(methylamino)propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCNC)=CC=C(F)C=C1 PTJADDMMFYXMMG-LJQANCHMSA-N 0.000 claims description 4
- VRYALKFFQXWPIH-PBXRRBTRSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)CC=O VRYALKFFQXWPIH-PBXRRBTRSA-N 0.000 claims description 4
- IORPHWDBRHOADK-ZWKOTPCHSA-N (6r)-6-[(1s)-7-hydroxy-6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]-6h-furo[3,4-g][1,3]benzodioxol-8-one Chemical compound O([C@H]1[C@H]2N(C)CCC=3C=C(C(=CC=32)O)OC)C(=O)C2=C1C=CC1=C2OCO1 IORPHWDBRHOADK-ZWKOTPCHSA-N 0.000 claims description 4
- YMHFBUOKLSWOQF-NSHGMRRFSA-N (6r,8s)-6-[(5s)-6-methyl-7,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,8-dihydrofuro[3,4-g][1,3]benzodioxol-8-ol Chemical compound C1([C@@H](O)O[C@H]2[C@@H]3C4=CC=5OCOC=5C=C4CCN3C)=C2C=CC2=C1OCO2 YMHFBUOKLSWOQF-NSHGMRRFSA-N 0.000 claims description 4
- 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 claims description 4
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 claims description 4
- VPIXQGUBUKFLRF-UHFFFAOYSA-N 3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N-methyl-1-propanamine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCNC)C2=CC=CC=C21 VPIXQGUBUKFLRF-UHFFFAOYSA-N 0.000 claims description 4
- FWYRGHMKHZXXQX-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(CO)CC1=CC=C(Cl)C(Cl)=C1 FWYRGHMKHZXXQX-UHFFFAOYSA-N 0.000 claims description 4
- BQGLPDFQLBNUGU-UHFFFAOYSA-N 4-(fluoromethyl)-n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n-pyridin-2-ylcyclohexane-1-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCC(CF)CC2)C=2N=CC=CC=2)CC1 BQGLPDFQLBNUGU-UHFFFAOYSA-N 0.000 claims description 4
- QXIUMMLTJVHILT-UHFFFAOYSA-N 4-[3-(tert-butylamino)-2-hydroxypropoxy]-1H-indole-2-carbonitrile Chemical compound CC(C)(C)NCC(O)COC1=CC=CC2=C1C=C(C#N)N2 QXIUMMLTJVHILT-UHFFFAOYSA-N 0.000 claims description 4
- 102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 0.000 claims description 4
- 102100024959 5-hydroxytryptamine receptor 2C Human genes 0.000 claims description 4
- 101710138093 5-hydroxytryptamine receptor 2C Proteins 0.000 claims description 4
- KWQWBZIGHIOKIO-UHFFFAOYSA-N 5-propoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[3,2-b]pyridine Chemical compound C12=NC(OCCC)=CC=C2NC=C1C1=CCNCC1 KWQWBZIGHIOKIO-UHFFFAOYSA-N 0.000 claims description 4
- YPNWSZJDAKOUAW-UHFFFAOYSA-N 8,9-dichloro-1,2,3,4,4a,6-hexahydropyrazino[1,2-a]quinoxalin-5-one;hydrochloride Chemical compound Cl.N1C(=O)C2CNCCN2C2=C1C=C(Cl)C(Cl)=C2 YPNWSZJDAKOUAW-UHFFFAOYSA-N 0.000 claims description 4
- HCVRCHQFYYZPHT-UHFFFAOYSA-N 8-[4-(2,3-dihydro-1,4-benzodioxin-3-ylmethylamino)butyl]-8-azaspiro[4.5]decane-7,9-dione Chemical compound C1C(=O)N(CCCCNCC2OC3=CC=CC=C3OC2)C(=O)CC21CCCC2 HCVRCHQFYYZPHT-UHFFFAOYSA-N 0.000 claims description 4
- IYGYMKDQCDOMRE-QRWMCTBCSA-N Bicculine Chemical compound O([C@H]1C2C3=CC=4OCOC=4C=C3CCN2C)C(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-QRWMCTBCSA-N 0.000 claims description 4
- KPSRODZRAIWAKH-JTQLQIEISA-N Ciprofibrate Natural products C1=CC(OC(C)(C)C(O)=O)=CC=C1[C@H]1C(Cl)(Cl)C1 KPSRODZRAIWAKH-JTQLQIEISA-N 0.000 claims description 4
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 claims description 4
- YMHFBUOKLSWOQF-UHFFFAOYSA-N Egenine Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(O)C2=C1C=CC1=C2OCO1 YMHFBUOKLSWOQF-UHFFFAOYSA-N 0.000 claims description 4
- HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 claims description 4
- BYTORXDZJWWIKR-UHFFFAOYSA-N Hinokiol Natural products CC(C)c1cc2CCC3C(C)(CO)C(O)CCC3(C)c2cc1O BYTORXDZJWWIKR-UHFFFAOYSA-N 0.000 claims description 4
- 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 claims description 4
- 101000628562 Homo sapiens Serine/threonine-protein kinase STK11 Proteins 0.000 claims description 4
- MADRVGBADLFHMO-UHFFFAOYSA-N Indeloxazine Chemical compound C=1C=CC=2C=CCC=2C=1OCC1CNCCO1 MADRVGBADLFHMO-UHFFFAOYSA-N 0.000 claims description 4
- 102000016267 Leptin Human genes 0.000 claims description 4
- 108010092277 Leptin Proteins 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- RLJFTICUTYVZDG-UHFFFAOYSA-N Methiothepine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2CC1N1CCN(C)CC1 RLJFTICUTYVZDG-UHFFFAOYSA-N 0.000 claims description 4
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 claims description 4
- 101710181599 Serine/threonine-protein kinase STK11 Proteins 0.000 claims description 4
- AEQDJSLRWYMAQI-UHFFFAOYSA-N Tetrahydropalmatine Natural products C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 claims description 4
- 229930003451 Vitamin B1 Natural products 0.000 claims description 4
- 229930003537 Vitamin B3 Natural products 0.000 claims description 4
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000012190 activator Substances 0.000 claims description 4
- 229960001570 ademetionine Drugs 0.000 claims description 4
- PMMURAAUARKVCB-UHFFFAOYSA-N alpha-D-ara-dHexp Natural products OCC1OC(O)CC(O)C1O PMMURAAUARKVCB-UHFFFAOYSA-N 0.000 claims description 4
- PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 claims description 4
- 229960002213 alprenolol Drugs 0.000 claims description 4
- 235000010323 ascorbic acid Nutrition 0.000 claims description 4
- 229960005070 ascorbic acid Drugs 0.000 claims description 4
- 239000011668 ascorbic acid Substances 0.000 claims description 4
- 229960005245 asenapine Drugs 0.000 claims description 4
- 229960000516 bezafibrate Drugs 0.000 claims description 4
- IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 claims description 4
- AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 claims description 4
- 235000020958 biotin Nutrition 0.000 claims description 4
- 239000011616 biotin Substances 0.000 claims description 4
- 229960002685 biotin Drugs 0.000 claims description 4
- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 claims description 4
- 229960002495 buspirone Drugs 0.000 claims description 4
- 150000001765 catechin Chemical class 0.000 claims description 4
- 229950000303 cericlamine Drugs 0.000 claims description 4
- 229960002174 ciprofibrate Drugs 0.000 claims description 4
- KPSRODZRAIWAKH-UHFFFAOYSA-N ciprofibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1C(Cl)(Cl)C1 KPSRODZRAIWAKH-UHFFFAOYSA-N 0.000 claims description 4
- 229960001653 citalopram Drugs 0.000 claims description 4
- 229960001214 clofibrate Drugs 0.000 claims description 4
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 claims description 4
- 235000017471 coenzyme Q10 Nutrition 0.000 claims description 4
- 229940110767 coenzyme Q10 Drugs 0.000 claims description 4
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims description 4
- FSIRGTNPQFDCCD-QGMBQPNBSA-N cyanodothiepin Chemical compound C1SC2=CC=C(C#N)C=C2C(=C/CCN(C)C)/C2=CC=CC=C21 FSIRGTNPQFDCCD-QGMBQPNBSA-N 0.000 claims description 4
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 claims description 4
- 229960005217 dapoxetine Drugs 0.000 claims description 4
- SRPXSILJHWNFMK-ZBEGNZNMSA-N desmethylsertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)N)=CC=C(Cl)C(Cl)=C1 SRPXSILJHWNFMK-ZBEGNZNMSA-N 0.000 claims description 4
- 229960004341 escitalopram Drugs 0.000 claims description 4
- WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 claims description 4
- OJSFTALXCYKKFQ-YLJYHZDGSA-N femoxetine Chemical compound C1=CC(OC)=CC=C1OC[C@@H]1[C@@H](C=2C=CC=CC=2)CCN(C)C1 OJSFTALXCYKKFQ-YLJYHZDGSA-N 0.000 claims description 4
- 229950003930 femoxetine Drugs 0.000 claims description 4
- 229960002297 fenofibrate Drugs 0.000 claims description 4
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 claims description 4
- 229940125753 fibrate Drugs 0.000 claims description 4
- 235000019152 folic acid Nutrition 0.000 claims description 4
- 229960000304 folic acid Drugs 0.000 claims description 4
- 239000011724 folic acid Substances 0.000 claims description 4
- 229960003627 gemfibrozil Drugs 0.000 claims description 4
- FVYXIJYOAGAUQK-UHFFFAOYSA-N honokiol Chemical compound C1=C(CC=C)C(O)=CC=C1C1=CC(CC=C)=CC=C1O FVYXIJYOAGAUQK-UHFFFAOYSA-N 0.000 claims description 4
- VVOAZFWZEDHOOU-UHFFFAOYSA-N honokiol Natural products OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 claims description 4
- NIBOMXUDFLRHRV-UHFFFAOYSA-N hydron;8-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-8-azaspiro[4.5]decane-7,9-dione;dichloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(CCN2C(CC3(CCCC3)CC2=O)=O)CC1 NIBOMXUDFLRHRV-UHFFFAOYSA-N 0.000 claims description 4
- ZHFIAFNZGWCLHU-YPMHNXCESA-N ifoxetine Chemical compound CC1=CC=CC(O[C@@H]2[C@@H](CNCC2)O)=C1C ZHFIAFNZGWCLHU-YPMHNXCESA-N 0.000 claims description 4
- 229950006314 ifoxetine Drugs 0.000 claims description 4
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 claims description 4
- 229960004801 imipramine Drugs 0.000 claims description 4
- 229950002473 indalpine Drugs 0.000 claims description 4
- 229960004333 indeloxazine Drugs 0.000 claims description 4
- WGSPBWSPJOBKNT-UHFFFAOYSA-N iodocyanopindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C(I)=C(C#N)N2 WGSPBWSPJOBKNT-UHFFFAOYSA-N 0.000 claims description 4
- 229940039781 leptin Drugs 0.000 claims description 4
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims description 4
- MJJDYOLPMGIWND-UHFFFAOYSA-N litoxetine Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CCNCC1 MJJDYOLPMGIWND-UHFFFAOYSA-N 0.000 claims description 4
- 229950004138 litoxetine Drugs 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 235000001055 magnesium Nutrition 0.000 claims description 4
- 229960001785 mirtazapine Drugs 0.000 claims description 4
- RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 claims description 4
- NQYXXIUVFVOJCX-XZPOUAKSSA-N n-[(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]-2-oxo-3-propan-2-ylbenzimidazole-1-carboxamide;hydrochloride Chemical compound Cl.C1[C@@H](N2C)CC[C@@H]2CC1NC(=O)N1C2=CC=CC=C2N(C(C)C)C1=O NQYXXIUVFVOJCX-XZPOUAKSSA-N 0.000 claims description 4
- JTSLALYXYSRPGW-UHFFFAOYSA-N n-[5-(4-cyanophenyl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(C1=C2)=CNC1=NC=C2C1=CC=C(C#N)C=C1 JTSLALYXYSRPGW-UHFFFAOYSA-N 0.000 claims description 4
- VRBKIVRKKCLPHA-UHFFFAOYSA-N nefazodone Chemical compound O=C1N(CCOC=2C=CC=CC=2)C(CC)=NN1CCCN(CC1)CCN1C1=CC=CC(Cl)=C1 VRBKIVRKKCLPHA-UHFFFAOYSA-N 0.000 claims description 4
- 229960001800 nefazodone Drugs 0.000 claims description 4
- 229960003512 nicotinic acid Drugs 0.000 claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
- WIQRCHMSJFFONW-UHFFFAOYSA-N norfluoxetine Chemical compound C=1C=CC=CC=1C(CCN)OC1=CC=C(C(F)(F)F)C=C1 WIQRCHMSJFFONW-UHFFFAOYSA-N 0.000 claims description 4
- 229960004570 oxprenolol Drugs 0.000 claims description 4
- 229960001511 pergolide mesylate Drugs 0.000 claims description 4
- UWCVGPLTGZWHGS-ZORIOUSZSA-N pergolide mesylate Chemical compound CS(O)(=O)=O.C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 UWCVGPLTGZWHGS-ZORIOUSZSA-N 0.000 claims description 4
- 229960002508 pindolol Drugs 0.000 claims description 4
- 229960004526 piracetam Drugs 0.000 claims description 4
- 229960003712 propranolol Drugs 0.000 claims description 4
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 claims description 4
- SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical class C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 claims description 4
- MQTUXRKNJYPMCG-CYBMUJFWSA-N robalzotan Chemical compound C1CCC1N([C@H]1COC=2C(F)=CC=C(C=2C1)C(=O)N)C1CCC1 MQTUXRKNJYPMCG-CYBMUJFWSA-N 0.000 claims description 4
- 229950003023 robalzotan Drugs 0.000 claims description 4
- SUFUKZSWUHZXAV-BTJKTKAUSA-N rosiglitazone maleate Chemical compound [H+].[H+].[O-]C(=O)\C=C/C([O-])=O.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O SUFUKZSWUHZXAV-BTJKTKAUSA-N 0.000 claims description 4
- 229960003271 rosiglitazone maleate Drugs 0.000 claims description 4
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 claims description 4
- 229950001675 spiperone Drugs 0.000 claims description 4
- 229960003495 thiamine Drugs 0.000 claims description 4
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 claims description 4
- 238000013519 translation Methods 0.000 claims description 4
- PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 claims description 4
- 229960003991 trazodone Drugs 0.000 claims description 4
- 229960004799 tryptophan Drugs 0.000 claims description 4
- 229960004688 venlafaxine Drugs 0.000 claims description 4
- 235000010374 vitamin B1 Nutrition 0.000 claims description 4
- 239000011691 vitamin B1 Substances 0.000 claims description 4
- 235000019160 vitamin B3 Nutrition 0.000 claims description 4
- 239000011708 vitamin B3 Substances 0.000 claims description 4
- 235000019158 vitamin B6 Nutrition 0.000 claims description 4
- 239000011726 vitamin B6 Substances 0.000 claims description 4
- 229940011671 vitamin b6 Drugs 0.000 claims description 4
- 229960002791 zimeldine Drugs 0.000 claims description 4
- OYPPVKRFBIWMSX-SXGWCWSVSA-N zimeldine Chemical compound C=1C=CN=CC=1C(=C/CN(C)C)\C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-SXGWCWSVSA-N 0.000 claims description 4
- 229960000607 ziprasidone Drugs 0.000 claims description 4
- 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 claims description 4
- GJJFMKBJSRMPLA-HIFRSBDPSA-N (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenyl-1-cyclopropanecarboxamide Chemical compound C=1C=CC=CC=1[C@@]1(C(=O)N(CC)CC)C[C@@H]1CN GJJFMKBJSRMPLA-HIFRSBDPSA-N 0.000 claims description 3
- IGLYMJRIWWIQQE-QUOODJBBSA-N (1S,2R)-2-phenylcyclopropan-1-amine (1R,2S)-2-phenylcyclopropan-1-amine Chemical compound N[C@H]1C[C@@H]1C1=CC=CC=C1.N[C@@H]1C[C@H]1C1=CC=CC=C1 IGLYMJRIWWIQQE-QUOODJBBSA-N 0.000 claims description 3
- ZXUYYZPJUGQHLQ-KRWDZBQOSA-N (1s)-1-(4-fluorophenyl)-4-[4-(5-fluoropyrimidin-2-yl)piperazin-1-yl]butan-1-ol Chemical compound C([C@H](O)C=1C=CC(F)=CC=1)CCN(CC1)CCN1C1=NC=C(F)C=N1 ZXUYYZPJUGQHLQ-KRWDZBQOSA-N 0.000 claims description 3
- XJJZQXUGLLXTHO-ZETCQYMHSA-N (2S)-1-(6-chloro-5-fluoroindol-1-yl)-propan-2-amine Chemical compound FC1=C(Cl)C=C2N(C[C@@H](N)C)C=CC2=C1 XJJZQXUGLLXTHO-ZETCQYMHSA-N 0.000 claims description 3
- MLBHFBKZUPLWBD-ZETCQYMHSA-N (2S)-1-[3-(trifluoromethyl)phenyl]-2-propanamine Chemical compound C[C@H](N)CC1=CC=CC(C(F)(F)F)=C1 MLBHFBKZUPLWBD-ZETCQYMHSA-N 0.000 claims description 3
- KMWGSFWAZUVTCM-SSDOTTSWSA-N (2r)-1-[4-(trifluoromethyl)-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl]propan-2-amine Chemical compound C[C@@H](N)CC1=C2CCOC2=C(C(F)(F)F)C2=C1OCC2 KMWGSFWAZUVTCM-SSDOTTSWSA-N 0.000 claims description 3
- VVHJUSGIUWQPIT-VIFPVBQESA-N (2s)-1-(3,7,8,9-tetrahydropyrano[3,2-e]indol-1-yl)propan-2-amine Chemical compound O1CCCC2=C3C(C[C@@H](N)C)=CNC3=CC=C21 VVHJUSGIUWQPIT-VIFPVBQESA-N 0.000 claims description 3
- LLWYXGZWWWNKKJ-RGSQJGBCSA-N (2s)-2-[[(2s)-2-amino-3-(5-hydroxy-1h-indol-3-yl)propanoyl]amino]butanedioic acid;trihydrate Chemical compound O.O.O.C1=C(O)C=C2C(C[C@H](N)C(=O)N[C@@H](CC(O)=O)C(O)=O)=CNC2=C1 LLWYXGZWWWNKKJ-RGSQJGBCSA-N 0.000 claims description 3
- MOFGVUQTFJGNSG-LBPRGKRZSA-N (2s)-2-acetamido-3-(5-hydroxy-1h-indol-3-yl)propanoic acid Chemical compound C1=C(O)C=C2C(C[C@H](NC(=O)C)C(O)=O)=CNC2=C1 MOFGVUQTFJGNSG-LBPRGKRZSA-N 0.000 claims description 3
- FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 claims description 3
- KPJZHOPZRAFDTN-ZRGWGRIASA-N (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)CC)C2)=C3C2=CN(C)C3=C1 KPJZHOPZRAFDTN-ZRGWGRIASA-N 0.000 claims description 3
- SACMXZDUZMBKSI-GYDOPSIJSA-N (e)-but-2-enedioic acid;(2s)-1-(4,4,7-trimethylindeno[1,2-b]pyrrol-1-yl)propan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.C12=CC(C)=CC=C2C(C)(C)C2=C1N(C[C@@H](N)C)C=C2 SACMXZDUZMBKSI-GYDOPSIJSA-N 0.000 claims description 3
- CEPHEXXZGQBXGT-XZTIXWOLSA-N (e)-but-2-enedioic acid;(2s)-1-(6-chloro-5-fluoroindol-1-yl)propan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.FC1=C(Cl)C=C2N(C[C@@H](N)C)C=CC2=C1 CEPHEXXZGQBXGT-XZTIXWOLSA-N 0.000 claims description 3
- TZJUVVIWVWFLCD-UHFFFAOYSA-N 1,1-dioxo-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-1,2-benzothiazol-3-one Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 TZJUVVIWVWFLCD-UHFFFAOYSA-N 0.000 claims description 3
- LCGFVWKNXLRFIF-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=CC=C2CC(N)CCC2=C1 LCGFVWKNXLRFIF-UHFFFAOYSA-N 0.000 claims description 3
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 3
- VNICFCQJUVFULD-UHFFFAOYSA-N 1-(1-naphthalenyl)piperazine Chemical compound C1CNCCN1C1=CC=CC2=CC=CC=C12 VNICFCQJUVFULD-UHFFFAOYSA-N 0.000 claims description 3
- NTJQREUGJKIARY-UHFFFAOYSA-N 1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine Chemical compound COC1=CC(CC(C)N)=C(OC)C=C1C NTJQREUGJKIARY-UHFFFAOYSA-N 0.000 claims description 3
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 claims description 3
- ILYJQDXYIVBGBE-FSPLSTOPSA-N 1-[(2s,5s)-4,4-difluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound C1C(F)(F)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 ILYJQDXYIVBGBE-FSPLSTOPSA-N 0.000 claims description 3
- CKYZLYQSDNLGPT-HNNXBMFYSA-N 1-[(4r)-4-(dipropylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-6-yl]ethanone Chemical compound C1=C(C(C)=O)C(C[C@@H](N(CCC)CCC)C2)=C3C2=CNC3=C1 CKYZLYQSDNLGPT-HNNXBMFYSA-N 0.000 claims description 3
- PYJBJMIBANAOFJ-UHFFFAOYSA-N 1-[5-(thiophen-2-ylmethoxy)-1h-indol-3-yl]propan-2-amine;hydrochloride Chemical compound Cl.C1=C2C(CC(N)C)=CNC2=CC=C1OCC1=CC=CS1 PYJBJMIBANAOFJ-UHFFFAOYSA-N 0.000 claims description 3
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 claims description 3
- MBXZPFLUPOKREA-UHFFFAOYSA-N 1-chloro-3-(diaminomethylidene)-1-phenylguanidine Chemical compound NC(N)=NC(=N)N(Cl)C1=CC=CC=C1 MBXZPFLUPOKREA-UHFFFAOYSA-N 0.000 claims description 3
- HYURFYKFWVWKEW-UHFFFAOYSA-N 1-fluoropiperazine Chemical compound FN1CCNCC1 HYURFYKFWVWKEW-UHFFFAOYSA-N 0.000 claims description 3
- PLRACCBDVIHHLZ-UHFFFAOYSA-N 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1N(C)CCC(C=2C=CC=CC=2)=C1 PLRACCBDVIHHLZ-UHFFFAOYSA-N 0.000 claims description 3
- VGEMBOFBPSNOIO-UHFFFAOYSA-N 1-methyl-n-pyridin-3-yl-6,7-dihydropyrrolo[2,3-f]indole-5-carboxamide;hydrochloride Chemical compound Cl.C1CC=2C=C3N(C)C=CC3=CC=2N1C(=O)NC1=CC=CN=C1 VGEMBOFBPSNOIO-UHFFFAOYSA-N 0.000 claims description 3
- RPSOLZRELOLSFM-UHFFFAOYSA-N 2-(1-benzyl-5-methoxy-2-methylindol-3-yl)ethanamine Chemical compound CC1=C(CCN)C2=CC(OC)=CC=C2N1CC1=CC=CC=C1 RPSOLZRELOLSFM-UHFFFAOYSA-N 0.000 claims description 3
- BGMZUEKZENQUJY-UHFFFAOYSA-N 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine Chemical compound COC1=CC(CC(C)N)=C(OC)C=C1I BGMZUEKZENQUJY-UHFFFAOYSA-N 0.000 claims description 3
- PCWGGOVOEWHPMG-UHFFFAOYSA-N 2-[(3-chlorophenyl)methoxy]-6-piperazin-1-ylpyrazine Chemical compound ClC1=CC=CC(COC=2N=C(C=NC=2)N2CCNCC2)=C1 PCWGGOVOEWHPMG-UHFFFAOYSA-N 0.000 claims description 3
- SFSFIDVAEMDPIP-UHFFFAOYSA-N 2-[3-(3-fluorophenyl)sulfonylpyrrolo[2,3-b]pyridin-1-yl]-n,n-dimethylethanamine Chemical compound C12=CC=CN=C2N(CCN(C)C)C=C1S(=O)(=O)C1=CC=CC(F)=C1 SFSFIDVAEMDPIP-UHFFFAOYSA-N 0.000 claims description 3
- CJAWPFJGFFNXQI-UHFFFAOYSA-N 2-chloro-6-(1-piperazinyl)pyrazine Chemical compound ClC1=CN=CC(N2CCNCC2)=N1 CJAWPFJGFFNXQI-UHFFFAOYSA-N 0.000 claims description 3
- PFIZGLUIYAZQFU-UHFFFAOYSA-N 2-chloro-6-piperazin-1-ylpyrazine;hydron;chloride Chemical compound Cl.ClC1=CN=CC(N2CCNCC2)=N1 PFIZGLUIYAZQFU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- NGBBVGZWCFBOGO-UHFFFAOYSA-N 3,4-Methylenedioxyamphetamine Chemical compound CC(N)CC1=CC=C2OCOC2=C1 NGBBVGZWCFBOGO-UHFFFAOYSA-N 0.000 claims description 3
- ZGUPMFYFHHSNFK-UHFFFAOYSA-N 3-[2-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]ethyl]-2-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound CC=1N=C2C=CC=CN2C(=O)C=1CCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 ZGUPMFYFHHSNFK-UHFFFAOYSA-N 0.000 claims description 3
- MLDQSYUQSLUEPG-UHFFFAOYSA-N 3-[4-[4-(4-fluorobenzoyl)piperidin-1-yl]butyl]-1h-quinazoline-2,4-dione Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCCCN2C(C3=CC=CC=C3NC2=O)=O)CC1 MLDQSYUQSLUEPG-UHFFFAOYSA-N 0.000 claims description 3
- LZENMJMJWQSSNJ-UHFFFAOYSA-N 3H-1,2-dithiole-3-thione Chemical compound S=C1C=CSS1 LZENMJMJWQSSNJ-UHFFFAOYSA-N 0.000 claims description 3
- YPELFRMCRYSPKZ-UHFFFAOYSA-N 4-amino-5-chloro-2-ethoxy-N-({4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl)benzamide Chemical compound CCOC1=CC(N)=C(Cl)C=C1C(=O)NCC1OCCN(CC=2C=CC(F)=CC=2)C1 YPELFRMCRYSPKZ-UHFFFAOYSA-N 0.000 claims description 3
- FEROPKNOYKURCJ-UHFFFAOYSA-N 4-amino-N-(1-azabicyclo[2.2.2]octan-3-yl)-5-chloro-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1C(CC2)CCN2C1 FEROPKNOYKURCJ-UHFFFAOYSA-N 0.000 claims description 3
- LZBWQEXVQZCBDJ-FERBBOLQSA-N 4-fluoro-n-[2-[4-[(2s)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-5-yl]piperazin-1-yl]ethyl]benzamide;hydrochloride Chemical compound Cl.C([C@@H](O1)CO)OC2=C1C=CC=C2N(CC1)CCN1CCNC(=O)C1=CC=C(F)C=C1 LZBWQEXVQZCBDJ-FERBBOLQSA-N 0.000 claims description 3
- UPJKSWLLCONYMW-UHFFFAOYSA-N 5'-Adenosine monophosphate Natural products COc1cc(O)c(C(=O)C)c(OC2OC(COC3OC(C)C(O)C(O)C3O)C(O)C(O)C2O)c1 UPJKSWLLCONYMW-UHFFFAOYSA-N 0.000 claims description 3
- WKPDXBXNJWWWGQ-UHFFFAOYSA-N 5-benzyloxytryptamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1OCC1=CC=CC=C1 WKPDXBXNJWWWGQ-UHFFFAOYSA-N 0.000 claims description 3
- BQBQAWXALAGUIW-GHVWMZMZSA-N 6-[5-[[(2s)-2-(4-fluorophenyl)-4-methylpiperazin-1-yl]methyl]furan-3-yl]-3h-1,3-benzoxazol-2-one;hydrate;hydrochloride Chemical compound O.Cl.C1([C@@H]2N(CC=3OC=C(C=3)C=3C=C4OC(O)=NC4=CC=3)CCN(C2)C)=CC=C(F)C=C1 BQBQAWXALAGUIW-GHVWMZMZSA-N 0.000 claims description 3
- HCFHWXDIZOAUTQ-UHFFFAOYSA-N 6-methyl-mda Chemical compound C1=C(C)C(CC(N)C)=CC2=C1OCO2 HCFHWXDIZOAUTQ-UHFFFAOYSA-N 0.000 claims description 3
- GGDBEAVVGFNWIA-UHFFFAOYSA-N 6-nitro-2-(1-piperazinyl)quinoline Chemical compound C1=CC2=CC([N+](=O)[O-])=CC=C2N=C1N1CCNCC1 GGDBEAVVGFNWIA-UHFFFAOYSA-N 0.000 claims description 3
- JVGBTTIJPBFLTE-UHFFFAOYSA-N 8-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1CN(CC2OC3=CC=CC=C3OC2)CCC11C(=O)NCN1C1=CC=CC=C1 JVGBTTIJPBFLTE-UHFFFAOYSA-N 0.000 claims description 3
- BVMYCHKQPGEOSI-UHFFFAOYSA-N 8-[2-(2,3-dihydro-1,4-benzodioxin-3-ylmethylamino)ethyl]-8-azaspiro[4.5]decane-7,9-dione Chemical compound C1C(=O)N(CCNCC2OC3=CC=CC=C3OC2)C(=O)CC21CCCC2 BVMYCHKQPGEOSI-UHFFFAOYSA-N 0.000 claims description 3
- QYFHCFNBYQZGKW-BDQAORGHSA-N 8-[4-[[(3s)-5-methoxy-3,4-dihydro-2h-chromen-3-yl]-propylamino]butyl]-8-azaspiro[4.5]decane-7,9-dione;hydrochloride Chemical compound Cl.CCCN([C@H]1CC2=C(OC)C=CC=C2OC1)CCCCN(C(C1)=O)C(=O)CC21CCCC2 QYFHCFNBYQZGKW-BDQAORGHSA-N 0.000 claims description 3
- WKEMJKQOLOHJLZ-UHFFFAOYSA-N Almogran Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CS(=O)(=O)N1CCCC1 WKEMJKQOLOHJLZ-UHFFFAOYSA-N 0.000 claims description 3
- SMYALUSCZJXWHG-UHFFFAOYSA-N Altanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=S)=O)CC1 SMYALUSCZJXWHG-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 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 claims description 3
- 101000742062 Bos taurus Protein phosphatase 1G Proteins 0.000 claims description 3
- ZCKAMNXUHHNZLN-UHFFFAOYSA-N Chlorphentermine Chemical compound CC(C)(N)CC1=CC=C(Cl)C=C1 ZCKAMNXUHHNZLN-UHFFFAOYSA-N 0.000 claims description 3
- UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 claims description 3
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 claims description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 3
- NIGWMJHCCYYCSF-UHFFFAOYSA-N Fenclonine Chemical compound OC(=O)C(N)CC1=CC=C(Cl)C=C1 NIGWMJHCCYYCSF-UHFFFAOYSA-N 0.000 claims description 3
- GRSZFWQUAKGDAV-KQYNXXCUSA-L IMP(2-) Chemical compound O[C@@H]1[C@H](O)[C@@H](COP([O-])([O-])=O)O[C@H]1N1C(N=CNC2=O)=C2N=C1 GRSZFWQUAKGDAV-KQYNXXCUSA-L 0.000 claims description 3
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 claims description 3
- UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 claims description 3
- MPZVHKLZCUEJFO-UHFFFAOYSA-N N-[3-(2-acetamidoethyl)-1H-indol-5-yl]carbamic acid methyl ester Chemical compound COC(=O)NC1=CC=C2NC=C(CCNC(C)=O)C2=C1 MPZVHKLZCUEJFO-UHFFFAOYSA-N 0.000 claims description 3
- HKXMQLISPYELRD-UHFFFAOYSA-N N-[4-[[5-[3-(2-aminoethyl)-1H-indol-5-yl]-1,2,4-oxadiazol-3-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CC1=NOC(C=2C=C3C(CCN)=CNC3=CC=2)=N1 HKXMQLISPYELRD-UHFFFAOYSA-N 0.000 claims description 3
- MVAWJSIDNICKHF-UHFFFAOYSA-N N-acetylserotonin Chemical compound C1=C(O)C=C2C(CCNC(=O)C)=CNC2=C1 MVAWJSIDNICKHF-UHFFFAOYSA-N 0.000 claims description 3
- MOFGVUQTFJGNSG-UHFFFAOYSA-N Nalpha-Acetyl-5-hydroxy-tryptophan Natural products C1=C(O)C=C2C(CC(NC(=O)C)C(O)=O)=CNC2=C1 MOFGVUQTFJGNSG-UHFFFAOYSA-N 0.000 claims description 3
- COSPVUFTLGQDQL-UHFFFAOYSA-N Nelotanserin Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C=C1F COSPVUFTLGQDQL-UHFFFAOYSA-N 0.000 claims description 3
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 claims description 3
- 108091000080 Phosphotransferase Proteins 0.000 claims description 3
- AQRLDDAFYYAIJP-UHFFFAOYSA-N Pruvanserin Chemical compound C1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C=3NC=C(C=3C=CC=2)C#N)CC1 AQRLDDAFYYAIJP-UHFFFAOYSA-N 0.000 claims description 3
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 claims description 3
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 claims description 3
- HPFLVTSWRFCPCV-UHFFFAOYSA-N adatanserin Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)NCCN(CC1)CCN1C1=NC=CC=N1 HPFLVTSWRFCPCV-UHFFFAOYSA-N 0.000 claims description 3
- 229950008881 adatanserin Drugs 0.000 claims description 3
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 claims description 3
- 229960002133 almotriptan Drugs 0.000 claims description 3
- 229950000420 alnespirone Drugs 0.000 claims description 3
- 229950001123 alniditan Drugs 0.000 claims description 3
- 229950009005 altanserin Drugs 0.000 claims description 3
- 229960000836 amitriptyline Drugs 0.000 claims description 3
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 claims description 3
- 229960002519 amoxapine Drugs 0.000 claims description 3
- QWGDMFLQWFTERH-UHFFFAOYSA-N amoxapine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2N=C1N1CCNCC1 QWGDMFLQWFTERH-UHFFFAOYSA-N 0.000 claims description 3
- VHGCDTVCOLNTBX-QGZVFWFLSA-N atomoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=CC=C1C VHGCDTVCOLNTBX-QGZVFWFLSA-N 0.000 claims description 3
- 229960002430 atomoxetine Drugs 0.000 claims description 3
- SEBMTIQKRHYNIT-UHFFFAOYSA-N azatadine Chemical compound C1CN(C)CCC1=C1C2=NC=CC=C2CCC2=CC=CC=C21 SEBMTIQKRHYNIT-UHFFFAOYSA-N 0.000 claims description 3
- 229960000383 azatadine Drugs 0.000 claims description 3
- MTYYDFXUUJQQRS-UHFFFAOYSA-N batoprazine Chemical compound C=12OC(=O)C=CC2=CC=CC=1N1CCNCC1 MTYYDFXUUJQQRS-UHFFFAOYSA-N 0.000 claims description 3
- 229950002408 batoprazine Drugs 0.000 claims description 3
- RVSGRNKUJJUAPV-UHFFFAOYSA-N benzo[d][1,2]benzoxazepine Chemical compound O1N=CC2=CC=CC=C2C2=CC=CC=C12 RVSGRNKUJJUAPV-UHFFFAOYSA-N 0.000 claims description 3
- DAVFDHSQRNNSTQ-UHFFFAOYSA-N benzyl 4-[(4-fluorophenyl)methylamino]piperidine-1-carboxylate Chemical compound C1=CC(F)=CC=C1CNC1CCN(C(=O)OCC=2C=CC=CC=2)CC1 DAVFDHSQRNNSTQ-UHFFFAOYSA-N 0.000 claims description 3
- 229950009087 bifeprunox Drugs 0.000 claims description 3
- 229950005615 binospirone Drugs 0.000 claims description 3
- 229950002871 blonanserin Drugs 0.000 claims description 3
- 229950000295 butanserin Drugs 0.000 claims description 3
- PBKVEOSEPXMKDN-LZHUFOCISA-N chembl2311030 Chemical class CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)CC)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 PBKVEOSEPXMKDN-LZHUFOCISA-N 0.000 claims description 3
- UKTAZPQNNNJVKR-KJGYPYNMSA-N chembl2368925 Chemical compound C1=CC=C2C(C(O[C@@H]3C[C@@H]4C[C@H]5C[C@@H](N4CC5=O)C3)=O)=CNC2=C1 UKTAZPQNNNJVKR-KJGYPYNMSA-N 0.000 claims description 3
- 229950007046 chlorphentermine Drugs 0.000 claims description 3
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 claims description 3
- 229960001076 chlorpromazine Drugs 0.000 claims description 3
- LQXYCDLHSKICDY-UHFFFAOYSA-N cianopramine Chemical compound C1CC2=CC=C(C#N)C=C2N(CCCN(C)C)C2=CC=CC=C21 LQXYCDLHSKICDY-UHFFFAOYSA-N 0.000 claims description 3
- 229950001408 cianopramine Drugs 0.000 claims description 3
- RSUVYMGADVXGOU-BUHFOSPRSA-N cinanserin Chemical compound CN(C)CCCSC1=CC=CC=C1NC(=O)\C=C\C1=CC=CC=C1 RSUVYMGADVXGOU-BUHFOSPRSA-N 0.000 claims description 3
- 229950001684 cinanserin Drugs 0.000 claims description 3
- ZDLBNXXKDMLZMF-UHFFFAOYSA-N cinitapride Chemical compound CCOC1=CC(N)=C([N+]([O-])=O)C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1 ZDLBNXXKDMLZMF-UHFFFAOYSA-N 0.000 claims description 3
- 229960003875 cinitapride Drugs 0.000 claims description 3
- DCSUBABJRXZOMT-IRLDBZIGSA-N cisapride Chemical compound C([C@@H]([C@@H](CC1)NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)OC)N1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-IRLDBZIGSA-N 0.000 claims description 3
- 229960005132 cisapride Drugs 0.000 claims description 3
- DCSUBABJRXZOMT-UHFFFAOYSA-N cisapride Natural products C1CC(NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)C(OC)CN1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-UHFFFAOYSA-N 0.000 claims description 3
- 229960004170 clozapine Drugs 0.000 claims description 3
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims description 3
- JURKNVYFZMSNLP-UHFFFAOYSA-N cyclobenzaprine Chemical compound C1=CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 JURKNVYFZMSNLP-UHFFFAOYSA-N 0.000 claims description 3
- 229960003572 cyclobenzaprine Drugs 0.000 claims description 3
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 claims description 3
- 229960001140 cyproheptadine Drugs 0.000 claims description 3
- YFXIKEZOBJFVAQ-UHFFFAOYSA-N dazopride Chemical compound C1N(CC)N(CC)CC1NC(=O)C1=CC(Cl)=C(N)C=C1OC YFXIKEZOBJFVAQ-UHFFFAOYSA-N 0.000 claims description 3
- 229950005815 dazopride Drugs 0.000 claims description 3
- 229960003914 desipramine Drugs 0.000 claims description 3
- HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 claims description 3
- 229960004704 dihydroergotamine Drugs 0.000 claims description 3
- WBPQJTBOQCCTFX-UHFFFAOYSA-N dimemebfe Chemical compound COC1=CC=C2OC=C(CCN(C)C)C2=C1 WBPQJTBOQCCTFX-UHFFFAOYSA-N 0.000 claims description 3
- 229960003413 dolasetron Drugs 0.000 claims description 3
- SOHCKWZVTCTQBG-UHFFFAOYSA-N donitriptan Chemical compound C1=C2C(CCN)=CNC2=CC=C1OCC(=O)N(CC1)CCN1C1=CC=C(C#N)C=C1 SOHCKWZVTCTQBG-UHFFFAOYSA-N 0.000 claims description 3
- 229950010344 donitriptan Drugs 0.000 claims description 3
- 229960005426 doxepin Drugs 0.000 claims description 3
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 3
- 229960002866 duloxetine Drugs 0.000 claims description 3
- 229960002472 eletriptan Drugs 0.000 claims description 3
- VAIOZOCLKVMIMN-PRJWTAEASA-N eplivanserin Chemical compound C=1C=CC=C(F)C=1\C(=N/OCCN(C)C)\C=C\C1=CC=C(O)C=C1 VAIOZOCLKVMIMN-PRJWTAEASA-N 0.000 claims description 3
- 229950000789 eplivanserin Drugs 0.000 claims description 3
- 229940040520 ergoloid mesylates Drugs 0.000 claims description 3
- 229950003853 fenclonine Drugs 0.000 claims description 3
- 229960002053 flibanserin Drugs 0.000 claims description 3
- CHQKHXJPWDSTPY-UHFFFAOYSA-N fluprazine Chemical compound C1CN(CCNC(=O)N)CCN1C1=CC=CC(C(F)(F)F)=C1 CHQKHXJPWDSTPY-UHFFFAOYSA-N 0.000 claims description 3
- 229950006789 fluprazine Drugs 0.000 claims description 3
- 229960002284 frovatriptan Drugs 0.000 claims description 3
- SIBNYOSJIXCDRI-SECBINFHSA-N frovatriptan Chemical compound C1=C(C(N)=O)[CH]C2=C(C[C@H](NC)CC3)C3=NC2=C1 SIBNYOSJIXCDRI-SECBINFHSA-N 0.000 claims description 3
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 claims description 3
- 229960001625 furazolidone Drugs 0.000 claims description 3
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 3
- 229960000647 gepirone Drugs 0.000 claims description 3
- QOIGKGMMAGJZNZ-UHFFFAOYSA-N gepirone Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 QOIGKGMMAGJZNZ-UHFFFAOYSA-N 0.000 claims description 3
- 229950003791 glemanserin Drugs 0.000 claims description 3
- MFWNKCLOYSRHCJ-BTTYYORXSA-N granisetron Chemical compound C1=CC=C2C(C(=O)N[C@H]3C[C@H]4CCC[C@@H](C3)N4C)=NN(C)C2=C1 MFWNKCLOYSRHCJ-BTTYYORXSA-N 0.000 claims description 3
- 229960003727 granisetron Drugs 0.000 claims description 3
- UXIPFQUBOVWAQW-UEBLJOKOSA-N iferanserin Chemical compound CN1CCCC[C@H]1CCC1=CC=CC=C1NC(=O)\C=C\C1=CC=CC=C1 UXIPFQUBOVWAQW-UEBLJOKOSA-N 0.000 claims description 3
- 229950003656 iferanserin Drugs 0.000 claims description 3
- 229960003162 iloperidone Drugs 0.000 claims description 3
- 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 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 229950003599 ipsapirone Drugs 0.000 claims description 3
- AFTIZGHFDCOQFS-QMMMGPOBSA-N jimscaline Chemical compound COC1=C(OC)C(OC)=CC2=C1CC[C@H]2CN AFTIZGHFDCOQFS-QMMMGPOBSA-N 0.000 claims description 3
- FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 claims description 3
- 229960005417 ketanserin Drugs 0.000 claims description 3
- XEDHVZKDSYZQBF-UHFFFAOYSA-N lasmiditan Chemical compound C1CN(C)CCC1C(=O)C1=CC=CC(NC(=O)C=2C(=CC(F)=CC=2F)F)=N1 XEDHVZKDSYZQBF-UHFFFAOYSA-N 0.000 claims description 3
- AHCPKWJUALHOPH-UHFFFAOYSA-N lesopitron Chemical compound C1=C(Cl)C=NN1CCCCN1CCN(C=2N=CC=CN=2)CC1 AHCPKWJUALHOPH-UHFFFAOYSA-N 0.000 claims description 3
- 229950001590 lesopitron Drugs 0.000 claims description 3
- JDYWZVJXSMADHP-UHFFFAOYSA-N lidanserin Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OCCCN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 JDYWZVJXSMADHP-UHFFFAOYSA-N 0.000 claims description 3
- 229950003713 lidanserin Drugs 0.000 claims description 3
- 229960002813 lofepramine Drugs 0.000 claims description 3
- SAPNXPWPAUFAJU-UHFFFAOYSA-N lofepramine Chemical compound C12=CC=CC=C2CCC2=CC=CC=C2N1CCCN(C)CC(=O)C1=CC=C(Cl)C=C1 SAPNXPWPAUFAJU-UHFFFAOYSA-N 0.000 claims description 3
- 229960005060 lorcaserin Drugs 0.000 claims description 3
- XTTZERNUQAFMOF-QMMMGPOBSA-N lorcaserin Chemical compound C[C@H]1CNCCC2=CC=C(Cl)C=C12 XTTZERNUQAFMOF-QMMMGPOBSA-N 0.000 claims description 3
- 229950002454 lysergide Drugs 0.000 claims description 3
- 229960004090 maprotiline Drugs 0.000 claims description 3
- QSLMDECMDJKHMQ-GSXCWMCISA-N maprotiline Chemical compound C12=CC=CC=C2[C@@]2(CCCNC)C3=CC=CC=C3[C@@H]1CC2 QSLMDECMDJKHMQ-GSXCWMCISA-N 0.000 claims description 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 3
- 229960001186 methysergide Drugs 0.000 claims description 3
- 229960004503 metoclopramide Drugs 0.000 claims description 3
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 claims description 3
- 229960003955 mianserin Drugs 0.000 claims description 3
- 229960000600 milnacipran Drugs 0.000 claims description 3
- YHXISWVBGDMDLQ-UHFFFAOYSA-N moclobemide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCCN1CCOCC1 YHXISWVBGDMDLQ-UHFFFAOYSA-N 0.000 claims description 3
- 229960004644 moclobemide Drugs 0.000 claims description 3
- 229960004085 mosapride Drugs 0.000 claims description 3
- 230000035772 mutation Effects 0.000 claims description 3
- ZNAPADWWBWFMCQ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-2-(1-methylindol-3-yl)-2-oxoacetamide Chemical compound C12=CC=CC=C2N(C)C=C1C(=O)C(=O)NC1C(CC2)CCN2C1 ZNAPADWWBWFMCQ-UHFFFAOYSA-N 0.000 claims description 3
- QVSXOXCYXPQXMF-OAHLLOKOSA-N n-[[(2r)-3,4-dihydro-2h-chromen-2-yl]methyl]-n'-(1,4,5,6-tetrahydropyrimidin-2-yl)propane-1,3-diamine Chemical compound C([C@@H]1OC2=CC=CC=C2CC1)NCCCNC1=NCCCN1 QVSXOXCYXPQXMF-OAHLLOKOSA-N 0.000 claims description 3
- 229960005254 naratriptan Drugs 0.000 claims description 3
- OMLDMGPCWMBPAN-YPMHNXCESA-N norcisapride Chemical compound CO[C@H]1CNCC[C@H]1NC(=O)C1=CC(Cl)=C(N)C=C1OC OMLDMGPCWMBPAN-YPMHNXCESA-N 0.000 claims description 3
- 229960001158 nortriptyline Drugs 0.000 claims description 3
- 229950010634 ocaperidone Drugs 0.000 claims description 3
- 229960005343 ondansetron Drugs 0.000 claims description 3
- QDJAYXYEXHVXJV-UHFFFAOYSA-N org 37,684 Chemical compound COC1=CC=C2CCCC2=C1OC1CCNC1 QDJAYXYEXHVXJV-UHFFFAOYSA-N 0.000 claims description 3
- 229960002888 oxitriptan Drugs 0.000 claims description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
- 229960002131 palonosetron Drugs 0.000 claims description 3
- CPZBLNMUGSZIPR-NVXWUHKLSA-N palonosetron Chemical compound C1N(CC2)CCC2[C@@H]1N1C(=O)C(C=CC=C2CCC3)=C2[C@H]3C1 CPZBLNMUGSZIPR-NVXWUHKLSA-N 0.000 claims description 3
- WPKPLSFHHBBLRY-UHFFFAOYSA-N pelanserin Chemical compound O=C1NC2=CC=CC=C2C(=O)N1CCCN(CC1)CCN1C1=CC=CC=C1 WPKPLSFHHBBLRY-UHFFFAOYSA-N 0.000 claims description 3
- 229950005867 pelanserin Drugs 0.000 claims description 3
- 229960000964 phenelzine Drugs 0.000 claims description 3
- 229960003562 phentermine Drugs 0.000 claims description 3
- AXNGJCOYCMDPQG-UHFFFAOYSA-N phenyl-[1-(2-phenylethyl)-4-piperidinyl]methanol Chemical compound C=1C=CC=CC=1C(O)C(CC1)CCN1CCC1=CC=CC=C1 AXNGJCOYCMDPQG-UHFFFAOYSA-N 0.000 claims description 3
- 102000020233 phosphotransferase Human genes 0.000 claims description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 3
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 claims description 3
- 229960000624 procarbazine Drugs 0.000 claims description 3
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 claims description 3
- 229960002601 protriptyline Drugs 0.000 claims description 3
- BWPIARFWQZKAIA-UHFFFAOYSA-N protriptyline Chemical compound C1=CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 BWPIARFWQZKAIA-UHFFFAOYSA-N 0.000 claims description 3
- ZPMNHBXQOOVQJL-UHFFFAOYSA-N prucalopride Chemical compound C1CN(CCCOC)CCC1NC(=O)C1=CC(Cl)=C(N)C2=C1OCC2 ZPMNHBXQOOVQJL-UHFFFAOYSA-N 0.000 claims description 3
- 229960003863 prucalopride Drugs 0.000 claims description 3
- 229950003077 pruvanserin Drugs 0.000 claims description 3
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 3
- XRXDAJYKGWNHTQ-UHFFFAOYSA-N quipazine Chemical compound C1CNCCN1C1=CC=C(C=CC=C2)C2=N1 XRXDAJYKGWNHTQ-UHFFFAOYSA-N 0.000 claims description 3
- 229950002315 quipazine Drugs 0.000 claims description 3
- BLGXFZZNTVWLAY-DIRVCLHFSA-N rauwolscine Chemical compound C1=CC=C2C(CCN3C[C@H]4CC[C@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-DIRVCLHFSA-N 0.000 claims description 3
- YGYBFMRFXNDIPO-QGZVFWFLSA-N repinotan Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCNC[C@@H]1OC2=CC=CC=C2CC1 YGYBFMRFXNDIPO-QGZVFWFLSA-N 0.000 claims description 3
- 229950009693 repinotan Drugs 0.000 claims description 3
- 229960001534 risperidone Drugs 0.000 claims description 3
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 3
- JUQLTPCYUFPYKE-UHFFFAOYSA-N ritanserin Chemical compound CC=1N=C2SC=CN2C(=O)C=1CCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 JUQLTPCYUFPYKE-UHFFFAOYSA-N 0.000 claims description 3
- 229950009626 ritanserin Drugs 0.000 claims description 3
- 229960000425 rizatriptan Drugs 0.000 claims description 3
- 229950010947 seganserin Drugs 0.000 claims description 3
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 claims description 3
- 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 claims description 3
- 229960000652 sertindole Drugs 0.000 claims description 3
- GVPIXRLYKVFFMK-UHFFFAOYSA-N setiptiline Chemical compound C12=CC=CC=C2CC2=CC=CC=C2C2=C1CN(C)CC2 GVPIXRLYKVFFMK-UHFFFAOYSA-N 0.000 claims description 3
- 229950002275 setiptiline Drugs 0.000 claims description 3
- 229950001330 spiroxatrine Drugs 0.000 claims description 3
- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 claims description 3
- CEIJFEGBUDEYSX-FZDBZEDMSA-N tandospirone Chemical compound O=C([C@@H]1[C@H]2CC[C@H](C2)[C@@H]1C1=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 CEIJFEGBUDEYSX-FZDBZEDMSA-N 0.000 claims description 3
- 229950000505 tandospirone Drugs 0.000 claims description 3
- IKBKZGMPCYNSLU-RGVLZGJSSA-N tegaserod Chemical compound C1=C(OC)C=C2C(/C=N/NC(=N)NCCCCC)=CNC2=C1 IKBKZGMPCYNSLU-RGVLZGJSSA-N 0.000 claims description 3
- 229960002876 tegaserod Drugs 0.000 claims description 3
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical class O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 3
- 229960003741 tranylcypromine Drugs 0.000 claims description 3
- FEZBIKUBAYAZIU-UHFFFAOYSA-N trimethobenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCC=2C=CC(OCCN(C)C)=CC=2)=C1 FEZBIKUBAYAZIU-UHFFFAOYSA-N 0.000 claims description 3
- 229960004161 trimethobenzamide Drugs 0.000 claims description 3
- 229960002431 trimipramine Drugs 0.000 claims description 3
- ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 claims description 3
- 229950008832 tropanserin Drugs 0.000 claims description 3
- HDDNYFLPWFSBLN-ZSHCYNCHSA-N tropanyl 3,5-dimethylbenzoate Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C1=CC(C)=CC(C)=C1 HDDNYFLPWFSBLN-ZSHCYNCHSA-N 0.000 claims description 3
- 229960003688 tropisetron Drugs 0.000 claims description 3
- 229960001130 urapidil Drugs 0.000 claims description 3
- 229960003740 vilazodone Drugs 0.000 claims description 3
- SGEGOXDYSFKCPT-UHFFFAOYSA-N vilazodone Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(OC4=CC=3)C(=O)N)=CNC2=C1 SGEGOXDYSFKCPT-UHFFFAOYSA-N 0.000 claims description 3
- RYBOXBBYCVOYNO-UHFFFAOYSA-N way-181,187 Chemical compound C1=CC=C2C(CCN)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=C1 RYBOXBBYCVOYNO-UHFFFAOYSA-N 0.000 claims description 3
- WJJYZXPHLSLMGE-UHFFFAOYSA-N xaliproden Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C4C=CC=CC4=CC=3)CC=2)=C1 WJJYZXPHLSLMGE-UHFFFAOYSA-N 0.000 claims description 3
- 229960004664 xaliproden Drugs 0.000 claims description 3
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 claims description 3
- 229960000317 yohimbine Drugs 0.000 claims description 3
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 claims description 3
- 229950004681 zacopride Drugs 0.000 claims description 3
- 229950005255 zalospirone Drugs 0.000 claims description 3
- 229960001360 zolmitriptan Drugs 0.000 claims description 3
- HDOZVRUNCMBHFH-UHFFFAOYSA-N zotepine Chemical compound CN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C12 HDOZVRUNCMBHFH-UHFFFAOYSA-N 0.000 claims description 3
- 229960004496 zotepine Drugs 0.000 claims description 3
- WDDZPZKGLZNGEH-MRXNPFEDSA-N (8r)-8-(dipropylamino)-6,7,8,9-tetrahydro-3h-benzo[e]indole-2-carbonitrile Chemical compound C1=C2NC(C#N)=CC2=C2C[C@H](N(CCC)CCC)CCC2=C1 WDDZPZKGLZNGEH-MRXNPFEDSA-N 0.000 claims description 2
- NRANUECGGQVXOT-UHFFFAOYSA-N 2,5-dimethoxy-4-fluoroamphetamine Chemical compound COC1=CC(CC(C)N)=C(OC)C=C1F NRANUECGGQVXOT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 238000001361 intraarterial administration Methods 0.000 claims description 2
- 238000007917 intracranial administration Methods 0.000 claims description 2
- 238000007918 intramuscular administration Methods 0.000 claims description 2
- 238000007919 intrasynovial administration Methods 0.000 claims description 2
- 238000007913 intrathecal administration Methods 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- RZVWBASHHLFBJF-UHFFFAOYSA-N methyl piperidine-4-carboxylate Chemical compound COC(=O)C1CCNCC1 RZVWBASHHLFBJF-UHFFFAOYSA-N 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- RKEWSXXUOLRFBX-UHFFFAOYSA-N pimavanserin Chemical compound C1=CC(OCC(C)C)=CC=C1CNC(=O)N(C1CCN(C)CC1)CC1=CC=C(F)C=C1 RKEWSXXUOLRFBX-UHFFFAOYSA-N 0.000 claims description 2
- 229960003300 pimavanserin Drugs 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- JBHLYIVFFLNISJ-UHFFFAOYSA-N 1-(4-amino-5-chloro-2-methoxyphenyl)-3-(1-butyl-4-piperidinyl)-1-propanone Chemical compound C1CN(CCCC)CCC1CCC(=O)C1=CC(Cl)=C(N)C=C1OC JBHLYIVFFLNISJ-UHFFFAOYSA-N 0.000 claims 4
- HJXRBPYILFMTFB-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(trifluoromethoxy)phenyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(F)=CC=C1CN(C(=O)CC=1C=CC(OC(F)(F)F)=CC=1)C1CCN(CCC2OCCCO2)CC1 HJXRBPYILFMTFB-UHFFFAOYSA-N 0.000 claims 4
- ZMBCUKXEUOSWGR-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-[1-(2-methylpropyl)piperidin-4-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC(C)C)CC1)CC1=CC=C(C)C=C1 ZMBCUKXEUOSWGR-UHFFFAOYSA-N 0.000 claims 4
- SMWZUXMNZBDIAG-UHFFFAOYSA-N 3-[[4-(difluoromethoxy)phenyl]methyl]-4-[(4-fluorophenyl)methyl]-8-methyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CN(C)CCC21C(CC=1C=CC(F)=CC=1)N(CC=1C=CC(OC(F)F)=CC=1)C(=O)O2 SMWZUXMNZBDIAG-UHFFFAOYSA-N 0.000 claims 4
- NFSHZLYJOOSGSP-UHFFFAOYSA-N methyl 4-[[(1-methylpiperidin-4-yl)-(2-phenylacetyl)amino]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN(C(=O)CC=1C=CC=CC=1)C1CCN(C)CC1 NFSHZLYJOOSGSP-UHFFFAOYSA-N 0.000 claims 4
- NXEGQZFQEFXUPG-UHFFFAOYSA-N methyl 4-[[(1-methylpiperidin-4-yl)-[2-[4-(trifluoromethyl)phenyl]acetyl]amino]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN(C(=O)CC=1C=CC(=CC=1)C(F)(F)F)C1CCN(C)CC1 NXEGQZFQEFXUPG-UHFFFAOYSA-N 0.000 claims 4
- MMMDEIOFQATTCZ-UHFFFAOYSA-N methyl 4-[[[2-(4-chlorophenyl)acetyl]-(1-methylpiperidin-4-yl)amino]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN(C(=O)CC=1C=CC(Cl)=CC=1)C1CCN(C)CC1 MMMDEIOFQATTCZ-UHFFFAOYSA-N 0.000 claims 4
- QZAWKLHAILRSAZ-UHFFFAOYSA-N methyl 4-[[[2-(4-methoxyphenyl)acetyl]-(1-methylpiperidin-4-yl)amino]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN(C(=O)CC=1C=CC(OC)=CC=1)C1CCN(C)CC1 QZAWKLHAILRSAZ-UHFFFAOYSA-N 0.000 claims 4
- MRNILWZJWJXWHZ-UHFFFAOYSA-N n-(1-ethylpiperidin-4-yl)-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1CN(CC)CCC1N(C(=O)CC=1C=CC(OC)=CC=1)CC1=CC=C(C)C=C1 MRNILWZJWJXWHZ-UHFFFAOYSA-N 0.000 claims 4
- LXDQVMKDNJISSM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(4-methoxyphenyl)-n-(1-propan-2-ylpiperidin-4-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC1)C(C)C)CC1=CC=C(Cl)C=C1 LXDQVMKDNJISSM-UHFFFAOYSA-N 0.000 claims 4
- STIFSQDNBGWGOP-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-(1-methylpiperidin-4-yl)-2-(4-propoxyphenyl)acetamide Chemical compound C1=CC(OCCC)=CC=C1CC(=O)N(C1CCN(C)CC1)CC1=CC=C(F)C=C1 STIFSQDNBGWGOP-UHFFFAOYSA-N 0.000 claims 4
- SYBIVMMYWUDKOQ-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-n-(1-methylpiperidin-4-yl)-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1CN(C(=O)CC=1C=CC(=CC=1)C(F)(F)F)C1CCN(C)CC1 SYBIVMMYWUDKOQ-UHFFFAOYSA-N 0.000 claims 4
- AHGNJBSTWQOSAB-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(C)CC1)CC1=CC=C(C)C=C1 AHGNJBSTWQOSAB-UHFFFAOYSA-N 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- STYHSPDDGQTRRQ-UHFFFAOYSA-N n-(1-cyclobutylpiperidin-4-yl)-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC1)C1CCC1)CC1=CC=C(C)C=C1 STYHSPDDGQTRRQ-UHFFFAOYSA-N 0.000 claims 3
- GIKPTWKWYXCBEC-SSDOTTSWSA-N (2r)-1-(4-bromofuro[2,3-f][1]benzofuran-8-yl)propan-2-amine Chemical compound C[C@@H](N)CC1=C2C=COC2=C(Br)C2=C1OC=C2 GIKPTWKWYXCBEC-SSDOTTSWSA-N 0.000 claims 2
- HFAGRFQTWDJXDH-LREBCSMRSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;n-[1-[1-(1,3-dioxan-2-yl)propan-2-yl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CC1)C(C)CC1OCCCO1)CC1=CC=C(F)C=C1 HFAGRFQTWDJXDH-LREBCSMRSA-N 0.000 claims 2
- SQQPUNPTRQWGPO-LREBCSMRSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(1,2,4-triazol-4-yl)phenyl]acetamide Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(F)=CC=C1CN(C(=O)CC=1C=CC(=CC=1)N1C=NN=C1)C1CCN(CCC2OCCCO2)CC1 SQQPUNPTRQWGPO-LREBCSMRSA-N 0.000 claims 2
- BYTRZQOWWRJDMZ-ZETCQYMHSA-N (2s)-1-(2-chloro-5-fluoroindol-1-yl)propan-2-amine Chemical compound FC1=CC=C2N(C[C@@H](N)C)C(Cl)=CC2=C1 BYTRZQOWWRJDMZ-ZETCQYMHSA-N 0.000 claims 2
- IPIHGDDHIVDPOJ-LBPRGKRZSA-N (2s)-1-(4,4,7-trimethylindeno[1,2-b]pyrrol-1-yl)propan-2-amine Chemical compound C12=CC(C)=CC=C2C(C)(C)C2=C1N(C[C@@H](N)C)C=C2 IPIHGDDHIVDPOJ-LBPRGKRZSA-N 0.000 claims 2
- YWNMBFXNRAQXHP-KRWDZBQOSA-N (2s)-3-(5-hydroxy-1h-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound N([C@@H](CC=1C2=CC(O)=CC=C2NC=1)C(=O)O)C(=O)OCC1=CC=CC=C1 YWNMBFXNRAQXHP-KRWDZBQOSA-N 0.000 claims 2
- ZXUYYZPJUGQHLQ-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[4-(5-fluoro-2-pyrimidinyl)-1-piperazinyl]-1-butanol Chemical compound C=1C=C(F)C=CC=1C(O)CCCN(CC1)CCN1C1=NC=C(F)C=N1 ZXUYYZPJUGQHLQ-UHFFFAOYSA-N 0.000 claims 2
- JQLATQJWGRFCDN-UHFFFAOYSA-N 1-[2-(1,3-dioxan-4-yl)ethyl]-n-[(4-fluorophenyl)methyl]piperidin-4-amine Chemical compound C1=CC(F)=CC=C1CNC1CCN(CCC2OCOCC2)CC1 JQLATQJWGRFCDN-UHFFFAOYSA-N 0.000 claims 2
- FVDILXYXZAAJOS-UHFFFAOYSA-N 1-[6-chloro-5-(trifluoromethyl)pyridin-2-yl]piperazine;hydrochloride Chemical compound Cl.N1=C(Cl)C(C(F)(F)F)=CC=C1N1CCNCC1 FVDILXYXZAAJOS-UHFFFAOYSA-N 0.000 claims 2
- WDPSTGJPAHMNLS-UHFFFAOYSA-N 1-methyl-n-[(4-methylphenyl)methyl]-n-(2-phenylethyl)piperidin-4-amine Chemical compound C1CN(C)CCC1N(CC=1C=CC(C)=CC=1)CCC1=CC=CC=C1 WDPSTGJPAHMNLS-UHFFFAOYSA-N 0.000 claims 2
- VCDDWUTZJNYDSO-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;2-(4-fluorophenyl)-n-[(4-fluorophenyl)methyl]-n-[1-(oxan-4-yl)piperidin-4-yl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(F)=CC=C1CN(C(=O)CC=1C=CC(F)=CC=1)C1CCN(C2CCOCC2)CC1 VCDDWUTZJNYDSO-UHFFFAOYSA-N 0.000 claims 2
- AMYCDCNEVONKBI-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-(oxan-4-yl)piperidin-4-yl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CC1)C1CCOCC1)CC1=CC=C(F)C=C1 AMYCDCNEVONKBI-UHFFFAOYSA-N 0.000 claims 2
- XMPTYGYZODPMRN-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-(oxan-4-ylmethyl)piperidin-4-yl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CC2CCOCC2)CC1)CC1=CC=C(F)C=C1 XMPTYGYZODPMRN-UHFFFAOYSA-N 0.000 claims 2
- AGUKPQYZKLBFLO-JIDHJSLPSA-N 2,3-dihydroxybutanedioic acid;n-[(4-fluorophenyl)methyl]-n-[1-[3-[(4s)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]propyl]piperidin-4-yl]-2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2C(OC[C@@H]2C)=O)CC1)CC1=CC=C(F)C=C1 AGUKPQYZKLBFLO-JIDHJSLPSA-N 0.000 claims 2
- SZYMEOTWGBFQJK-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-(2,2-dimethyl-1,3-dioxan-5-yl)piperidin-4-yl]-2-(4-fluorophenyl)-n-[(4-fluorophenyl)methyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1OC(C)(C)OCC1N1CCC(N(CC=2C=CC(F)=CC=2)C(=O)CC=2C=CC(F)=CC=2)CC1 SZYMEOTWGBFQJK-UHFFFAOYSA-N 0.000 claims 2
- MBXWZBCTOUWFKU-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-2-(4-fluorophenyl)-n-[(4-fluorophenyl)methyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(F)=CC=C1CN(C(=O)CC=1C=CC(F)=CC=1)C1CCN(CCC2OCCCO2)CC1 MBXWZBCTOUWFKU-UHFFFAOYSA-N 0.000 claims 2
- NNSUXCFLFKKFIM-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-(4-hydroxyphenyl)acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(O)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CC1=CC=C(F)C=C1 NNSUXCFLFKKFIM-UHFFFAOYSA-N 0.000 claims 2
- PDMZHTVPWASOLH-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-(4-methoxyphenyl)acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CC1=CC=C(F)C=C1 PDMZHTVPWASOLH-UHFFFAOYSA-N 0.000 claims 2
- BGRVMIRSTFGTQC-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-(4-methylphenyl)acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(C)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CC1=CC=C(F)C=C1 BGRVMIRSTFGTQC-UHFFFAOYSA-N 0.000 claims 2
- UVIUJSPWGGUCLK-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-(4-phenylmethoxyphenyl)acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(F)=CC=C1CN(C(=O)CC=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1CCN(CCC2OCCCO2)CC1 UVIUJSPWGGUCLK-UHFFFAOYSA-N 0.000 claims 2
- BOWPUDZQYGZVLH-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-hydroxy-2-methylpropoxy)phenyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCC(C)(O)C)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CC1=CC=C(F)C=C1 BOWPUDZQYGZVLH-UHFFFAOYSA-N 0.000 claims 2
- GJQSKUVNDXBUAT-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-4-yl)ethyl]piperidin-4-yl]-2-(4-fluorophenyl)-n-[(4-fluorophenyl)methyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(F)=CC=C1CN(C(=O)CC=1C=CC(F)=CC=1)C1CCN(CCC2OCOCC2)CC1 GJQSKUVNDXBUAT-UHFFFAOYSA-N 0.000 claims 2
- RDSTWDGJVWDMJW-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-4-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-(4-propoxyphenyl)acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCCC)=CC=C1CC(=O)N(C1CCN(CCC2OCOCC2)CC1)CC1=CC=C(F)C=C1 RDSTWDGJVWDMJW-UHFFFAOYSA-N 0.000 claims 2
- VZOZTUDRONIINK-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-4-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCC2OCOCC2)CC1)CC1=CC=C(F)C=C1 VZOZTUDRONIINK-UHFFFAOYSA-N 0.000 claims 2
- LTVQPELINSHZFF-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCC2OC(C)(C)OC2)CC1)CC1=CC=C(F)C=C1 LTVQPELINSHZFF-UHFFFAOYSA-N 0.000 claims 2
- VZOZTUDRONIINK-XXIQNXCHSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-[(4r)-1,3-dioxan-4-yl]ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CC[C@H]2OCOCC2)CC1)CC1=CC=C(F)C=C1 VZOZTUDRONIINK-XXIQNXCHSA-N 0.000 claims 2
- VZOZTUDRONIINK-JMAPEOGHSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-[(4s)-1,3-dioxan-4-yl]ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CC[C@@H]2OCOCC2)CC1)CC1=CC=C(F)C=C1 VZOZTUDRONIINK-JMAPEOGHSA-N 0.000 claims 2
- MXJLDGLGUPSNMG-UHFFFAOYSA-N 2-(1-benzofuran-5-yl)-n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]acetamide;2,3-dihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(F)=CC=C1CN(C(=O)CC=1C=C2C=COC2=CC=1)C1CCN(CCC2OCCCO2)CC1 MXJLDGLGUPSNMG-UHFFFAOYSA-N 0.000 claims 2
- FAWRTCPQPAGZQD-UHFFFAOYSA-N 2-(4-butoxyphenyl)-n-[(4-fluorophenyl)methyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OCCCC)=CC=C1CC(=O)N(C1CCN(C)CC1)CC1=CC=C(F)C=C1 FAWRTCPQPAGZQD-UHFFFAOYSA-N 0.000 claims 2
- ZVALSPNIYTXPMC-UHFFFAOYSA-N 2-(4-butoxyphenyl)-n-[(4-methylphenyl)methyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OCCCC)=CC=C1CC(=O)N(C1CCN(C)CC1)CC1=CC=C(C)C=C1 ZVALSPNIYTXPMC-UHFFFAOYSA-N 0.000 claims 2
- LJRXPCZFUJHLAB-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(1-ethylpiperidin-4-yl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1CN(CC)CCC1N(C(=O)CC=1C=CC(Cl)=CC=1)CC1=CC=C(C)C=C1 LJRXPCZFUJHLAB-UHFFFAOYSA-N 0.000 claims 2
- VUAKFJFXPIYPML-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[(4-methylphenyl)methyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC(Cl)=CC=1)CC1=CC=C(C)C=C1 VUAKFJFXPIYPML-UHFFFAOYSA-N 0.000 claims 2
- QZLRORTWEQREKW-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[(4-methylphenyl)methyl]-n-(1-propan-2-ylpiperidin-4-yl)acetamide Chemical compound C1CN(C(C)C)CCC1N(C(=O)CC=1C=CC(Cl)=CC=1)CC1=CC=C(C)C=C1 QZLRORTWEQREKW-UHFFFAOYSA-N 0.000 claims 2
- XQVNFRJEIIBZNW-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[1-(2-hydroxyethyl)piperidin-4-yl]-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(C)=CC=C1CN(C(=O)CC=1C=CC(Cl)=CC=1)C1CCN(CCO)CC1 XQVNFRJEIIBZNW-UHFFFAOYSA-N 0.000 claims 2
- BQCOLMISGDBZJF-UHFFFAOYSA-N 2-(4-cyanophenyl)-n-[1-[2-(1,3-dioxan-4-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]acetamide;2,3-dihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(F)=CC=C1CN(C(=O)CC=1C=CC(=CC=1)C#N)C1CCN(CCC2OCOCC2)CC1 BQCOLMISGDBZJF-UHFFFAOYSA-N 0.000 claims 2
- FXPKGOFCBKBPHV-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-n-[(4-fluorophenyl)methyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OCC)=CC=C1CC(=O)N(C1CCN(C)CC1)CC1=CC=C(F)C=C1 FXPKGOFCBKBPHV-UHFFFAOYSA-N 0.000 claims 2
- LYOQVDYYCRULSU-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-n-[(4-methylphenyl)methyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OCC)=CC=C1CC(=O)N(C1CCN(C)CC1)CC1=CC=C(C)C=C1 LYOQVDYYCRULSU-UHFFFAOYSA-N 0.000 claims 2
- SZEMMOKISKDRMB-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(1-methylpiperidin-4-yl)-n-[[4-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC(F)=CC=1)CC1=CC=C(C(F)(F)F)C=C1 SZEMMOKISKDRMB-UHFFFAOYSA-N 0.000 claims 2
- CKAQAHDJBKVNIB-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[(4-methylphenyl)methyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC(F)=CC=1)CC1=CC=C(C)C=C1 CKAQAHDJBKVNIB-UHFFFAOYSA-N 0.000 claims 2
- LNUNDRMOYPJFGQ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-n-[(4-methylphenyl)methyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC(O)=CC=1)CC1=CC=C(C)C=C1 LNUNDRMOYPJFGQ-UHFFFAOYSA-N 0.000 claims 2
- NIWVNLWZHSFKPX-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(1-methylpiperidin-4-yl)-n-(1-phenylethyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(C)CC1)C(C)C1=CC=CC=C1 NIWVNLWZHSFKPX-UHFFFAOYSA-N 0.000 claims 2
- GXGUBAJJPHIIBJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(1-methylpiperidin-4-yl)-n-[[4-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(C)CC1)CC1=CC=C(C(F)(F)F)C=C1 GXGUBAJJPHIIBJ-UHFFFAOYSA-N 0.000 claims 2
- ZMHXKHKVVVLYEQ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(2-phenylethyl)-n-piperidin-4-ylacetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCNCC1)CCC1=CC=CC=C1 ZMHXKHKVVVLYEQ-UHFFFAOYSA-N 0.000 claims 2
- MVSDYKSPJPVFCI-GGAORHGYSA-N 2-(4-methoxyphenyl)-n-[(1r,5s)-8-methyl-8-azabicyclo[3.2.1]oct-3-en-4-yl]-n-[(4-methylphenyl)methyl]acetamide Chemical compound C=1([C@]2([H])CC[C@@](N2C)(CC=1)[H])N(C(=O)CC=1C=CC(OC)=CC=1)CC1=CC=C(C)C=C1 MVSDYKSPJPVFCI-GGAORHGYSA-N 0.000 claims 2
- LFAICPXGTPKNMN-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(2-methoxyphenyl)methyl]-n-piperidin-4-ylacetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCNCC1)CC1=CC=CC=C1OC LFAICPXGTPKNMN-UHFFFAOYSA-N 0.000 claims 2
- ZWRRAVVCBNBPOC-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(3-methylphenyl)methyl]-n-piperidin-4-ylacetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCNCC1)CC1=CC=CC(C)=C1 ZWRRAVVCBNBPOC-UHFFFAOYSA-N 0.000 claims 2
- BNQFSNZFCXZEOL-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-(1-pentylpiperidin-4-yl)acetamide Chemical compound C1CN(CCCCC)CCC1N(C(=O)CC=1C=CC(OC)=CC=1)CC1=CC=C(C)C=C1 BNQFSNZFCXZEOL-UHFFFAOYSA-N 0.000 claims 2
- PUCYKGSOSPTPBN-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-[1-(3-morpholin-4-ylpropyl)piperidin-4-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCCN2CCOCC2)CC1)CC1=CC=C(C)C=C1 PUCYKGSOSPTPBN-UHFFFAOYSA-N 0.000 claims 2
- XOMGJNYXAHVAER-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-[1-[(5-phenyl-1,2,4-oxadiazol-3-yl)methyl]piperidin-4-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC=2N=C(ON=2)C=2C=CC=CC=2)CC1)CC1=CC=C(C)C=C1 XOMGJNYXAHVAER-UHFFFAOYSA-N 0.000 claims 2
- DMIDBVYSZBUTBY-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-[1-[2-(2-oxoimidazolidin-1-yl)ethyl]piperidin-4-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCN2C(NCC2)=O)CC1)CC1=CC=C(C)C=C1 DMIDBVYSZBUTBY-UHFFFAOYSA-N 0.000 claims 2
- DZJSODJUKAKISE-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-[1-[3-(1,2,4-triazol-1-yl)propyl]piperidin-4-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCCN2N=CN=C2)CC1)CC1=CC=C(C)C=C1 DZJSODJUKAKISE-UHFFFAOYSA-N 0.000 claims 2
- BRQXWMGENMAMNW-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-[1-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]piperidin-4-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCCN2C(NC3=CC=CC=C32)=O)CC1)CC1=CC=C(C)C=C1 BRQXWMGENMAMNW-UHFFFAOYSA-N 0.000 claims 2
- PPEPMTWKGQFMRX-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-piperidin-4-ylacetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCNCC1)CC1=CC=C(C)C=C1 PPEPMTWKGQFMRX-UHFFFAOYSA-N 0.000 claims 2
- QNTKJHFJFQURRB-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NCC1=CC=C(C)C=C1 QNTKJHFJFQURRB-UHFFFAOYSA-N 0.000 claims 2
- XOUKOHWQFNHTNR-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[2-(4-methoxyphenyl)ethyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CCN(C(=O)CC=1C=CC(OC)=CC=1)C1CCN(C)CC1 XOUKOHWQFNHTNR-UHFFFAOYSA-N 0.000 claims 2
- MRMWSEVDXOVHBM-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1,4-benzodioxin-3-ylmethylamino)butyl]-1,1-dioxo-1,2-benzothiazol-3-one Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCNCC1OC2=CC=CC=C2OC1 MRMWSEVDXOVHBM-UHFFFAOYSA-N 0.000 claims 2
- CUFCITSPWAZWHS-UHFFFAOYSA-N 2cbfly-nbome Chemical compound COC1=CC=CC=C1CNCCC1=C(CCO2)C2=C(Br)C2=C1OCC2 CUFCITSPWAZWHS-UHFFFAOYSA-N 0.000 claims 2
- WKNFADCGOAHBPG-UHFFFAOYSA-N 3-(1-methyl-4-piperidinyl)-1H-indol-5-ol Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(O)C=C12 WKNFADCGOAHBPG-UHFFFAOYSA-N 0.000 claims 2
- PVHGMVIMINMVNS-UHFFFAOYSA-N 3-[(4-butoxyphenyl)methyl]-4-[(4-fluorophenyl)methyl]-8-methyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCCCC)=CC=C1CN1C(=O)OC2(CCN(C)CC2)C1CC1=CC=C(F)C=C1 PVHGMVIMINMVNS-UHFFFAOYSA-N 0.000 claims 2
- DPXOFRGRKPFZOD-UHFFFAOYSA-N 3-[2-(dipropylamino)ethyl]-1H-indole-5-carboxamide Chemical compound C1=C(C(N)=O)C=C2C(CCN(CCC)CCC)=CNC2=C1 DPXOFRGRKPFZOD-UHFFFAOYSA-N 0.000 claims 2
- DQTSHAQIPICLJX-UHFFFAOYSA-N 3-[[4-(cyclopropylmethoxy)phenyl]methyl]-4-[(4-fluorophenyl)methyl]-8-methyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CN(C)CCC21C(CC=1C=CC(F)=CC=1)N(CC=1C=CC(OCC3CC3)=CC=1)C(=O)O2 DQTSHAQIPICLJX-UHFFFAOYSA-N 0.000 claims 2
- YSKQQKAZRZLYSW-UHFFFAOYSA-N 3-[[4-(cyclopropylmethoxy)phenyl]methyl]-4-[(4-fluorophenyl)methyl]-8-propan-2-yl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CN(C(C)C)CCC21C(CC=1C=CC(F)=CC=1)N(CC=1C=CC(OCC3CC3)=CC=1)C(=O)O2 YSKQQKAZRZLYSW-UHFFFAOYSA-N 0.000 claims 2
- INTASUKZYYYPKS-UHFFFAOYSA-N 3-[[4-(cyclopropylmethoxy)phenyl]methyl]-8-(cyclopropylmethyl)-4-[(4-fluorophenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(F)=CC=C1CC1C2(CCN(CC3CC3)CC2)OC(=O)N1CC(C=C1)=CC=C1OCC1CC1 INTASUKZYYYPKS-UHFFFAOYSA-N 0.000 claims 2
- ZYJJKOORTGIZKY-UHFFFAOYSA-N 3-[[4-(cyclopropylmethoxy)phenyl]methyl]-8-[2-(1,3-dioxolan-2-yl)ethyl]-4-[(4-fluorophenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(F)=CC=C1CC1C2(CCN(CCC3OCCO3)CC2)OC(=O)N1CC(C=C1)=CC=C1OCC1CC1 ZYJJKOORTGIZKY-UHFFFAOYSA-N 0.000 claims 2
- IRZOSDNQMCHENF-UHFFFAOYSA-N 3-[[4-(cyclopropylmethoxy)phenyl]methyl]-8-ethyl-4-[(4-fluorophenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CN(CC)CCC21C(CC=1C=CC(F)=CC=1)N(CC=1C=CC(OCC3CC3)=CC=1)C(=O)O2 IRZOSDNQMCHENF-UHFFFAOYSA-N 0.000 claims 2
- SLVXSIQABPMLQB-UHFFFAOYSA-N 3-[[4-(difluoromethoxy)phenyl]methyl]-4-[(4-fluorophenyl)methyl]-8-[2-(2-oxoimidazolidin-1-yl)ethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OC(F)F)=CC=C1CN1C(=O)OC2(CCN(CCN3C(NCC3)=O)CC2)C1CC1=CC=C(F)C=C1 SLVXSIQABPMLQB-UHFFFAOYSA-N 0.000 claims 2
- FLOFYPLDYNCLFM-UHFFFAOYSA-N 3-[[4-(difluoromethoxy)phenyl]methyl]-4-[(4-fluorophenyl)methyl]-8-propan-2-yl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CN(C(C)C)CCC21C(CC=1C=CC(F)=CC=1)N(CC=1C=CC(OC(F)F)=CC=1)C(=O)O2 FLOFYPLDYNCLFM-UHFFFAOYSA-N 0.000 claims 2
- USSWLMFSAINJJH-UHFFFAOYSA-N 3-[[4-(difluoromethoxy)phenyl]methyl]-8-[2-(1,3-dioxolan-2-yl)ethyl]-4-[(4-fluorophenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OC(F)F)=CC=C1CN1C(=O)OC2(CCN(CCC3OCCO3)CC2)C1CC1=CC=C(F)C=C1 USSWLMFSAINJJH-UHFFFAOYSA-N 0.000 claims 2
- JXMSNQSFOFSVIF-UHFFFAOYSA-N 3-[[4-(difluoromethoxy)phenyl]methyl]-8-ethyl-4-[(4-fluorophenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CN(CC)CCC21C(CC=1C=CC(F)=CC=1)N(CC=1C=CC(OC(F)F)=CC=1)C(=O)O2 JXMSNQSFOFSVIF-UHFFFAOYSA-N 0.000 claims 2
- CFPTUNSXZUORMF-UHFFFAOYSA-N 4-(5,6-dimethyl-1-benzofuran-2-yl)piperidine;hydrochloride Chemical compound Cl.O1C=2C=C(C)C(C)=CC=2C=C1C1CCNCC1 CFPTUNSXZUORMF-UHFFFAOYSA-N 0.000 claims 2
- INIKDMJZXSMFLI-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-8-[2-(2-oxoimidazolidin-1-yl)ethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CCN3C(NCC3)=O)CC2)C1CC1=CC=C(Cl)C=C1 INIKDMJZXSMFLI-UHFFFAOYSA-N 0.000 claims 2
- MGOUSPHTOKOKJC-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-8-propan-2-yl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CC2)C(C)C)C1CC1=CC=C(Cl)C=C1 MGOUSPHTOKOKJC-UHFFFAOYSA-N 0.000 claims 2
- JTOYRDRPPYNEAJ-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-8-(cyclohexylmethyl)-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CC3CCCCC3)CC2)C1CC1=CC=C(Cl)C=C1 JTOYRDRPPYNEAJ-UHFFFAOYSA-N 0.000 claims 2
- XTXPATBIMYBMOI-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-8-(cyclopropylmethyl)-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CC3CC3)CC2)C1CC1=CC=C(Cl)C=C1 XTXPATBIMYBMOI-UHFFFAOYSA-N 0.000 claims 2
- GKGPODWCZHSYRB-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-8-[2-(1,3-dioxolan-2-yl)ethyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CCC3OCCO3)CC2)C1CC1=CC=C(Cl)C=C1 GKGPODWCZHSYRB-UHFFFAOYSA-N 0.000 claims 2
- DQEWZQOXGHKXRP-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-8-ethyl-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CN(CC)CCC21C(CC=1C=CC(Cl)=CC=1)N(CC=1C=CC(OCC(C)C)=CC=1)C(=O)O2 DQEWZQOXGHKXRP-UHFFFAOYSA-N 0.000 claims 2
- BEOCKPYIANKJLR-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-8-methyl-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(C)CC2)C1CC1=CC=C(Cl)C=C1 BEOCKPYIANKJLR-UHFFFAOYSA-N 0.000 claims 2
- JQIQHRVYQWVSBX-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-3-[(4-methoxyphenyl)methyl]-8-methyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)OC2(CCN(C)CC2)C1CC1=CC=C(F)C=C1 JQIQHRVYQWVSBX-UHFFFAOYSA-N 0.000 claims 2
- AVJCXYIJQLPRNC-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-8-(3-morpholin-4-ylpropyl)-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CCCN3CCOCC3)CC2)C1CC1=CC=C(F)C=C1 AVJCXYIJQLPRNC-UHFFFAOYSA-N 0.000 claims 2
- MCSHDQHLYQJXAB-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-8-[(2-methyl-1,3-thiazol-4-yl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CC=3N=C(C)SC=3)CC2)C1CC1=CC=C(F)C=C1 MCSHDQHLYQJXAB-UHFFFAOYSA-N 0.000 claims 2
- IHUCMQOEOLDICB-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-8-[2-(2-oxoimidazolidin-1-yl)ethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CCN3C(NCC3)=O)CC2)C1CC1=CC=C(F)C=C1 IHUCMQOEOLDICB-UHFFFAOYSA-N 0.000 claims 2
- CGWNABZZOGOLDC-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-8-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CCCN3C(NC4=CC=CC=C43)=O)CC2)C1CC1=CC=C(F)C=C1 CGWNABZZOGOLDC-UHFFFAOYSA-N 0.000 claims 2
- UKLPSUPCXYYLGD-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-8-propan-2-yl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CC2)C(C)C)C1CC1=CC=C(F)C=C1 UKLPSUPCXYYLGD-UHFFFAOYSA-N 0.000 claims 2
- GUWCCVKTJBWPNZ-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-8-[2-(2-oxoimidazolidin-1-yl)ethyl]-3-[[4-(trifluoromethoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(F)=CC=C1CC1C2(CCN(CCN3C(NCC3)=O)CC2)OC(=O)N1CC1=CC=C(OC(F)(F)F)C=C1 GUWCCVKTJBWPNZ-UHFFFAOYSA-N 0.000 claims 2
- NLXQPWMAMZZKMW-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-8-methyl-3-[(4-pentoxyphenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCCCCC)=CC=C1CN1C(=O)OC2(CCN(C)CC2)C1CC1=CC=C(F)C=C1 NLXQPWMAMZZKMW-UHFFFAOYSA-N 0.000 claims 2
- BWTPBWQYMSPSLT-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-8-methyl-3-[(4-propan-2-yloxyphenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OC(C)C)=CC=C1CN1C(=O)OC2(CCN(C)CC2)C1CC1=CC=C(F)C=C1 BWTPBWQYMSPSLT-UHFFFAOYSA-N 0.000 claims 2
- MQIAIZZWRJLNAG-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-8-methyl-3-[(4-propoxyphenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCCC)=CC=C1CN1C(=O)OC2(CCN(C)CC2)C1CC1=CC=C(F)C=C1 MQIAIZZWRJLNAG-UHFFFAOYSA-N 0.000 claims 2
- AFKMQMLVKYANOK-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-8-methyl-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(C)CC2)C1CC1=CC=C(F)C=C1 AFKMQMLVKYANOK-UHFFFAOYSA-N 0.000 claims 2
- SHVVIDKYQOPSDO-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-8-methyl-3-[[4-(trifluoromethoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CN(C)CCC21C(CC=1C=CC(F)=CC=1)N(CC=1C=CC(OC(F)(F)F)=CC=1)C(=O)O2 SHVVIDKYQOPSDO-UHFFFAOYSA-N 0.000 claims 2
- KJMRGSBUWMLYOR-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-8-propan-2-yl-3-[(4-propoxyphenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCCC)=CC=C1CN1C(=O)OC2(CCN(CC2)C(C)C)C1CC1=CC=C(F)C=C1 KJMRGSBUWMLYOR-UHFFFAOYSA-N 0.000 claims 2
- NXWIAUXCVLYGJV-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-8-propan-2-yl-3-[[4-(trifluoromethoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CN(C(C)C)CCC21C(CC=1C=CC(F)=CC=1)N(CC=1C=CC(OC(F)(F)F)=CC=1)C(=O)O2 NXWIAUXCVLYGJV-UHFFFAOYSA-N 0.000 claims 2
- BPPGPYJBCVXILI-UHFFFAOYSA-N 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Chemical compound CC=1NC2=CC=C(Cl)C=C2C=1C1=CCNCC1 BPPGPYJBCVXILI-UHFFFAOYSA-N 0.000 claims 2
- KRVMLPUDAOWOGN-UHFFFAOYSA-N 5-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Chemical compound C12=CC(OC)=CC=C2NC=C1C1=CCNCC1 KRVMLPUDAOWOGN-UHFFFAOYSA-N 0.000 claims 2
- WBJMGSVSSCEGFV-UHFFFAOYSA-N 5-methoxy-3-(1,2,3,6-tetrahydropyridin-5-yl)-1h-indole Chemical compound C12=CC(OC)=CC=C2NC=C1C1=CCCNC1 WBJMGSVSSCEGFV-UHFFFAOYSA-N 0.000 claims 2
- XIINJGOYULUJJU-UHFFFAOYSA-N 5-methoxy-3-(1,2,5,6-tetrahydro-4-pyridinyl)-1h-indole Chemical compound C=12[CH]C(OC)=CC=C2N=CC=1C1=CCNCC1 XIINJGOYULUJJU-UHFFFAOYSA-N 0.000 claims 2
- BQVNHCZRNMYBNR-UHFFFAOYSA-N 8-(cyclohexylmethyl)-3-[[4-(difluoromethoxy)phenyl]methyl]-4-[(4-fluorophenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OC(F)F)=CC=C1CN1C(=O)OC2(CCN(CC3CCCCC3)CC2)C1CC1=CC=C(F)C=C1 BQVNHCZRNMYBNR-UHFFFAOYSA-N 0.000 claims 2
- LWURIEPVULAASS-UHFFFAOYSA-N 8-(cyclohexylmethyl)-4-[(4-fluorophenyl)methyl]-3-[(4-propoxyphenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCCC)=CC=C1CN1C(=O)OC2(CCN(CC3CCCCC3)CC2)C1CC1=CC=C(F)C=C1 LWURIEPVULAASS-UHFFFAOYSA-N 0.000 claims 2
- BMSCXMWCCFLFJF-UHFFFAOYSA-N 8-(cyclohexylmethyl)-4-[(4-fluorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CC3CCCCC3)CC2)C1CC1=CC=C(F)C=C1 BMSCXMWCCFLFJF-UHFFFAOYSA-N 0.000 claims 2
- CLWTUENNHSDSNX-UHFFFAOYSA-N 8-(cyclohexylmethyl)-4-[(4-fluorophenyl)methyl]-3-[[4-(trifluoromethoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(F)=CC=C1CC1C2(CCN(CC3CCCCC3)CC2)OC(=O)N1CC1=CC=C(OC(F)(F)F)C=C1 CLWTUENNHSDSNX-UHFFFAOYSA-N 0.000 claims 2
- IVRGXNOWLMRIRH-UHFFFAOYSA-N 8-(cyclopropylmethyl)-3-[[4-(difluoromethoxy)phenyl]methyl]-4-[(4-fluorophenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OC(F)F)=CC=C1CN1C(=O)OC2(CCN(CC3CC3)CC2)C1CC1=CC=C(F)C=C1 IVRGXNOWLMRIRH-UHFFFAOYSA-N 0.000 claims 2
- AURHLKFVISTBFX-UHFFFAOYSA-N 8-(cyclopropylmethyl)-4-[(4-fluorophenyl)methyl]-3-[(4-propoxyphenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCCC)=CC=C1CN1C(=O)OC2(CCN(CC3CC3)CC2)C1CC1=CC=C(F)C=C1 AURHLKFVISTBFX-UHFFFAOYSA-N 0.000 claims 2
- URBSFHRXJRGKLF-UHFFFAOYSA-N 8-(cyclopropylmethyl)-4-[(4-fluorophenyl)methyl]-3-[[4-(trifluoromethoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(F)=CC=C1CC1C2(CCN(CC3CC3)CC2)OC(=O)N1CC1=CC=C(OC(F)(F)F)C=C1 URBSFHRXJRGKLF-UHFFFAOYSA-N 0.000 claims 2
- DJRCOXKZRABSIO-UHFFFAOYSA-N 8-[2-(1,3-dioxolan-2-yl)ethyl]-4-[(4-fluorophenyl)methyl]-3-[(4-propoxyphenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCCC)=CC=C1CN1C(=O)OC2(CCN(CCC3OCCO3)CC2)C1CC1=CC=C(F)C=C1 DJRCOXKZRABSIO-UHFFFAOYSA-N 0.000 claims 2
- ZQRIULVLSPBGOT-UHFFFAOYSA-N 8-[2-(1,3-dioxolan-2-yl)ethyl]-4-[(4-fluorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CCC3OCCO3)CC2)C1CC1=CC=C(F)C=C1 ZQRIULVLSPBGOT-UHFFFAOYSA-N 0.000 claims 2
- FZLJTJIOJPAISV-UHFFFAOYSA-N 8-[2-(1,3-dioxolan-2-yl)ethyl]-4-[(4-fluorophenyl)methyl]-3-[[4-(trifluoromethoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(F)=CC=C1CC1C2(CCN(CCC3OCCO3)CC2)OC(=O)N1CC1=CC=C(OC(F)(F)F)C=C1 FZLJTJIOJPAISV-UHFFFAOYSA-N 0.000 claims 2
- AYYCFGDXLUPJAQ-UHFFFAOYSA-N 8-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-8-azaspiro[4.5]decane-7,9-dione Chemical compound COC1=CC=CC=C1N1CCN(CCN2C(CC3(CCCC3)CC2=O)=O)CC1 AYYCFGDXLUPJAQ-UHFFFAOYSA-N 0.000 claims 2
- UYHMHPBMASSSPI-UHFFFAOYSA-N 8-cyclopentyl-4-[(4-fluorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CC2)C2CCCC2)C1CC1=CC=C(F)C=C1 UYHMHPBMASSSPI-UHFFFAOYSA-N 0.000 claims 2
- UMHSJLWRUWWQHM-UHFFFAOYSA-N 8-cyclopentyl-4-[(4-fluorophenyl)methyl]-3-[[4-(trifluoromethoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(F)=CC=C1CC1C2(CCN(CC2)C2CCCC2)OC(=O)N1CC1=CC=C(OC(F)(F)F)C=C1 UMHSJLWRUWWQHM-UHFFFAOYSA-N 0.000 claims 2
- NWAGPSBRYJEJOY-UHFFFAOYSA-N 8-ethyl-4-[(4-fluorophenyl)methyl]-3-[(4-propoxyphenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCCC)=CC=C1CN1C(=O)OC2(CCN(CC)CC2)C1CC1=CC=C(F)C=C1 NWAGPSBRYJEJOY-UHFFFAOYSA-N 0.000 claims 2
- BNBMEAWQJBZRBI-UHFFFAOYSA-N 8-ethyl-4-[(4-fluorophenyl)methyl]-3-[[4-(trifluoromethoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CN(CC)CCC21C(CC=1C=CC(F)=CC=1)N(CC=1C=CC(OC(F)(F)F)=CC=1)C(=O)O2 BNBMEAWQJBZRBI-UHFFFAOYSA-N 0.000 claims 2
- WNDGGLWGWBMKJI-UHFFFAOYSA-N C1=CC(OC)=CC=C1C(C)=CC(=O)N(C1CCN(C)CC1)CC1=CC=C(C)C=C1 Chemical compound C1=CC(OC)=CC=C1C(C)=CC(=O)N(C1CCN(C)CC1)CC1=CC=C(C)C=C1 WNDGGLWGWBMKJI-UHFFFAOYSA-N 0.000 claims 2
- ZNAPADWWBWFMCQ-HNNXBMFYSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-2-(1-methyl-3-indolyl)-2-oxoacetamide Chemical compound C12=CC=CC=C2N(C)C=C1C(=O)C(=O)N[C@@H]1C(CC2)CCN2C1 ZNAPADWWBWFMCQ-HNNXBMFYSA-N 0.000 claims 2
- IKLRDEVOHUKHPT-UHFFFAOYSA-N N-[(4-methylphenyl)methyl]-N-(1-methylpiperidin-4-yl)-2-(4-propoxyphenyl)acetamide Chemical compound C1=CC(OCCC)=CC=C1CC(=O)N(C1CCN(C)CC1)CC1=CC=C(C)C=C1 IKLRDEVOHUKHPT-UHFFFAOYSA-N 0.000 claims 2
- KYYIDSXMWOZKMP-UHFFFAOYSA-N O-desmethylvenlafaxine Chemical compound C1CCCCC1(O)C(CN(C)C)C1=CC=C(O)C=C1 KYYIDSXMWOZKMP-UHFFFAOYSA-N 0.000 claims 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 claims 2
- OTLDLQZJRFYOJR-LJQANCHMSA-N eletriptan Chemical compound CN1CCC[C@@H]1CC1=CN=C2[C]1C=C(CCS(=O)(=O)C=1C=CC=CC=1)C=C2 OTLDLQZJRFYOJR-LJQANCHMSA-N 0.000 claims 2
- IENIRZUYTXLHLP-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-2-(4-methoxyphenyl)-n-(3-phenylprop-2-enyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC=2C=CC=CC=2)CC1)CC=CC1=CC=CC=C1 IENIRZUYTXLHLP-UHFFFAOYSA-N 0.000 claims 2
- VHYUQICVZWUGAG-UHFFFAOYSA-N n-(1-benzylpyrrolidin-3-yl)-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CN(CC=2C=CC=CC=2)CC1)CC1=CC=C(C)C=C1 VHYUQICVZWUGAG-UHFFFAOYSA-N 0.000 claims 2
- RIJHJRPEIIFMNS-UHFFFAOYSA-N n-(1-cyclohexylpiperidin-4-yl)-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC1)C1CCCCC1)CC1=CC=C(C)C=C1 RIJHJRPEIIFMNS-UHFFFAOYSA-N 0.000 claims 2
- VECRASHWSXYSPX-UHFFFAOYSA-N n-(1-cyclopentylpiperidin-4-yl)-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC1)C1CCCC1)CC1=CC=C(C)C=C1 VECRASHWSXYSPX-UHFFFAOYSA-N 0.000 claims 2
- GNSPZLLLNYUBDJ-UHFFFAOYSA-N n-(1-cyclopropylpiperidin-4-yl)-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC1)C1CC1)CC1=CC=C(C)C=C1 GNSPZLLLNYUBDJ-UHFFFAOYSA-N 0.000 claims 2
- QJLXKAUQWIQXCI-UHFFFAOYSA-N n-(1-hexylpiperidin-4-yl)-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1CN(CCCCCC)CCC1N(C(=O)CC=1C=CC(OC)=CC=1)CC1=CC=C(C)C=C1 QJLXKAUQWIQXCI-UHFFFAOYSA-N 0.000 claims 2
- HHCIVKDLHCELFA-UHFFFAOYSA-N n-(1-methylpiperidin-4-yl)-2-[4-(trifluoromethyl)phenyl]-n-[[4-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC(=CC=1)C(F)(F)F)CC1=CC=C(C(F)(F)F)C=C1 HHCIVKDLHCELFA-UHFFFAOYSA-N 0.000 claims 2
- NQISNVUEEPQWQU-UHFFFAOYSA-N n-(1-methylpiperidin-4-yl)-2-phenyl-n-[[4-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC=CC=1)CC1=CC=C(C(F)(F)F)C=C1 NQISNVUEEPQWQU-UHFFFAOYSA-N 0.000 claims 2
- LMTPDCHDWOUUNC-UHFFFAOYSA-N n-(1-tert-butylpiperidin-4-yl)-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC1)C(C)(C)C)CC1=CC=C(C)C=C1 LMTPDCHDWOUUNC-UHFFFAOYSA-N 0.000 claims 2
- ATYRMXDSNCWAHP-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-yl)-2-(4-methoxyphenyl)-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(C)CC1)C1C2=CC=CC=C2CC1 ATYRMXDSNCWAHP-UHFFFAOYSA-N 0.000 claims 2
- LWGMJNNEFKEYRH-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)methyl]-2-(4-methoxyphenyl)-n-piperidin-4-ylacetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCNCC1)CC1=CC=C(Cl)C=C1Cl LWGMJNNEFKEYRH-UHFFFAOYSA-N 0.000 claims 2
- AKLZUXRDOUXCEC-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-(4-methoxyphenyl)-n-piperidin-4-ylacetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCNCC1)CC1=CC=CC=C1Cl AKLZUXRDOUXCEC-UHFFFAOYSA-N 0.000 claims 2
- WLCCRKJOGPYOMQ-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]-2-(4-methoxyphenyl)-n-piperidin-4-ylacetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCNCC1)CC1=CC=C(OC)C(OC)=C1 WLCCRKJOGPYOMQ-UHFFFAOYSA-N 0.000 claims 2
- WHCHFNRZVHORRD-UHFFFAOYSA-N n-[(3-bromophenyl)methyl]-2-(4-methoxyphenyl)-n-piperidin-4-ylacetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCNCC1)CC1=CC=CC(Br)=C1 WHCHFNRZVHORRD-UHFFFAOYSA-N 0.000 claims 2
- YEJGAAIFMHTHBL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(4-methoxyphenyl)-n-piperidin-4-ylacetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCNCC1)CC1=CC=C(Cl)C=C1 YEJGAAIFMHTHBL-UHFFFAOYSA-N 0.000 claims 2
- QDHYDFZRNGPWNM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(4-methylphenyl)-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC(C)=CC=1)CC1=CC=C(Cl)C=C1 QDHYDFZRNGPWNM-UHFFFAOYSA-N 0.000 claims 2
- LPDGGBLBOOWODE-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-n-(1-cyclopentylpiperidin-4-yl)-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC1)C1CCCC1)CC1=CC=C(Cl)C=C1 LPDGGBLBOOWODE-UHFFFAOYSA-N 0.000 claims 2
- MZVTUVXPPFGGLI-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-n-(1-ethylpiperidin-4-yl)-2-(4-methoxyphenyl)acetamide Chemical compound C1CN(CC)CCC1N(C(=O)CC=1C=CC(OC)=CC=1)CC1=CC=C(Cl)C=C1 MZVTUVXPPFGGLI-UHFFFAOYSA-N 0.000 claims 2
- WZWZQOJIBFOLES-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-(4-methoxyphenyl)-n-piperidin-4-ylacetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCNCC1)CC1=CC=C(F)C=C1 WZWZQOJIBFOLES-UHFFFAOYSA-N 0.000 claims 2
- OGMAIHYCSDBUPB-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-(3-piperidin-1-ylpropyl)piperidin-4-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2CCCCC2)CC1)CC1=CC=C(F)C=C1 OGMAIHYCSDBUPB-UHFFFAOYSA-N 0.000 claims 2
- NZWLYQRBSMCTCT-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]piperidin-4-yl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCC2(C)OCC(C)(C)CO2)CC1)CC1=CC=C(F)C=C1 NZWLYQRBSMCTCT-UHFFFAOYSA-N 0.000 claims 2
- BEPLWXJPQUOOLA-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-[2-(2-oxoimidazolidin-1-yl)ethyl]piperidin-4-yl]acetamide;hydrochloride Chemical compound Cl.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCN2C(NCC2)=O)CC1)CC1=CC=C(F)C=C1 BEPLWXJPQUOOLA-UHFFFAOYSA-N 0.000 claims 2
- IQLRRYSZEFTNKD-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-[2-(oxan-2-yloxy)ethyl]piperidin-4-yl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCOC2OCCCC2)CC1)CC1=CC=C(F)C=C1 IQLRRYSZEFTNKD-UHFFFAOYSA-N 0.000 claims 2
- XPLZCDVXPCDRCR-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-[3-(2-oxo-1,3-oxazolidin-3-yl)propyl]piperidin-4-yl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2C(OCC2)=O)CC1)CC1=CC=C(F)C=C1 XPLZCDVXPCDRCR-UHFFFAOYSA-N 0.000 claims 2
- DXUNJYKBADWTQI-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-[3-(2-oxopyrrolidin-1-yl)propyl]piperidin-4-yl]acetamide;hydrochloride Chemical compound Cl.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2C(CCC2)=O)CC1)CC1=CC=C(F)C=C1 DXUNJYKBADWTQI-UHFFFAOYSA-N 0.000 claims 2
- YRTSIKARPYISSN-JSSVAETHSA-N n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-[3-[(4s)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]propyl]piperidin-4-yl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2C(OC[C@@H]2C(C)C)=O)CC1)CC1=CC=C(F)C=C1 YRTSIKARPYISSN-JSSVAETHSA-N 0.000 claims 2
- AMTODGXLAXKHRP-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-(1-methylpiperidin-4-yl)-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC(=CC=1)C(F)(F)F)CC1=CC=C(F)C=C1 AMTODGXLAXKHRP-UHFFFAOYSA-N 0.000 claims 2
- TYYBZMHXNKMDQW-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-(1-methylpiperidin-4-yl)-2-[4-[(2-methylpropan-2-yl)oxy]phenyl]acetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC(OC(C)(C)C)=CC=1)CC1=CC=C(F)C=C1 TYYBZMHXNKMDQW-UHFFFAOYSA-N 0.000 claims 2
- BWMWVQKPICZZGC-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-(1-methylpiperidin-4-yl)-2-phenylacetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC=CC=1)CC1=CC=C(F)C=C1 BWMWVQKPICZZGC-UHFFFAOYSA-N 0.000 claims 2
- JPZSFPRPBHSLNP-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-[1-(3-morpholin-4-ylpropyl)piperidin-4-yl]-2-(4-propan-2-yloxyphenyl)acetamide;dihydrochloride Chemical compound Cl.Cl.C1=CC(OC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2CCOCC2)CC1)CC1=CC=C(F)C=C1 JPZSFPRPBHSLNP-UHFFFAOYSA-N 0.000 claims 2
- JVVBSYFLWZSJHK-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-[1-[2-(2-oxoimidazolidin-1-yl)ethyl]piperidin-4-yl]-2-(4-propan-2-yloxyphenyl)acetamide;hydrochloride Chemical compound Cl.C1=CC(OC(C)C)=CC=C1CC(=O)N(C1CCN(CCN2C(NCC2)=O)CC1)CC1=CC=C(F)C=C1 JVVBSYFLWZSJHK-UHFFFAOYSA-N 0.000 claims 2
- XISQEHXIVSASPR-HURRXZTCSA-N n-[(4-fluorophenyl)methyl]-n-[1-[2-[(2s)-4-methyl-1,3-dioxolan-2-yl]ethyl]piperidin-4-yl]-2-(4-propan-2-ylphenyl)acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(C(C)C)=CC=C1CC(=O)N(C1CCN(CC[C@@H]2OC(C)CO2)CC1)CC1=CC=C(F)C=C1 XISQEHXIVSASPR-HURRXZTCSA-N 0.000 claims 2
- LXBJWYNFDLUAAY-DPKJPEAFSA-N n-[(4-fluorophenyl)methyl]-n-[1-[2-[(2s)-4-methyl-1,3-dioxolan-2-yl]ethyl]piperidin-4-yl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CC[C@@H]2OC(C)CO2)CC1)CC1=CC=C(F)C=C1 LXBJWYNFDLUAAY-DPKJPEAFSA-N 0.000 claims 2
- DVBZBQISLWFTBV-UKBNZDFYSA-N n-[(4-fluorophenyl)methyl]-n-[1-[2-[(2s)-4-methyl-1,3-dioxolan-2-yl]ethyl]piperidin-4-yl]-2-[4-(trifluoromethoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.O1C(C)CO[C@@H]1CCN1CCC(N(CC=2C=CC(F)=CC=2)C(=O)CC=2C=CC(OC(F)(F)F)=CC=2)CC1 DVBZBQISLWFTBV-UKBNZDFYSA-N 0.000 claims 2
- WHOYKFSUOFTWMT-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-[1-[3-(2-methylpiperidin-1-yl)propyl]piperidin-4-yl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2C(CCCC2)C)CC1)CC1=CC=C(F)C=C1 WHOYKFSUOFTWMT-UHFFFAOYSA-N 0.000 claims 2
- BOLNQXLCCDRYDA-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-[1-[3-(3-hydroxypiperidin-1-yl)propyl]piperidin-4-yl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2CC(O)CCC2)CC1)CC1=CC=C(F)C=C1 BOLNQXLCCDRYDA-UHFFFAOYSA-N 0.000 claims 2
- MMRXGNIMEGRFQR-VNUFCWELSA-N n-[(4-fluorophenyl)methyl]-n-[1-[3-[(4s)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]propyl]piperidin-4-yl]-2-(4-propoxyphenyl)acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCCC)=CC=C1CC(=O)N(C1CCN(CCCN2C(OC[C@@H]2C(C)C)=O)CC1)CC1=CC=C(F)C=C1 MMRXGNIMEGRFQR-VNUFCWELSA-N 0.000 claims 2
- BFQVTWUMJREMGT-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-[1-[3-[3-(hydroxymethyl)piperidin-1-yl]propyl]piperidin-4-yl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2CC(CO)CCC2)CC1)CC1=CC=C(F)C=C1 BFQVTWUMJREMGT-UHFFFAOYSA-N 0.000 claims 2
- RYJQRDWEWQIWFE-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-[1-[4-(2-oxo-3h-benzimidazol-1-yl)butyl]piperidin-4-yl]-2-(4-propan-2-yloxyphenyl)acetamide;hydrochloride Chemical compound Cl.C1=CC(OC(C)C)=CC=C1CC(=O)N(C1CCN(CCCCN2C(NC3=CC=CC=C32)=O)CC1)CC1=CC=C(F)C=C1 RYJQRDWEWQIWFE-UHFFFAOYSA-N 0.000 claims 2
- FBLLAGNNKMNOKY-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]-n-(1-methylpiperidin-4-yl)-2-[4-[(2-methylpropan-2-yl)oxy]phenyl]acetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC(OC(C)(C)C)=CC=1)CC1=CC=C(C)C=C1 FBLLAGNNKMNOKY-UHFFFAOYSA-N 0.000 claims 2
- UHRVMZCYMZAKRF-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]-n-(1-methylpiperidin-4-yl)-2-phenylacetamide Chemical compound C1CN(C)CCC1N(C(=O)CC=1C=CC=CC=1)CC1=CC=C(C)C=C1 UHRVMZCYMZAKRF-UHFFFAOYSA-N 0.000 claims 2
- OVJDRLDRAZDKQS-UHFFFAOYSA-N n-[1-(2,1,3-benzoxadiazol-5-ylmethyl)piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC2=CC3=NON=C3C=C2)CC1)CC1=CC=C(C)C=C1 OVJDRLDRAZDKQS-UHFFFAOYSA-N 0.000 claims 2
- GPOFWOCKZFERBP-UHFFFAOYSA-N n-[1-(2,2-dimethyl-1,3-dioxan-5-yl)piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CC1)C1COC(C)(C)OC1)CC1=CC=C(F)C=C1 GPOFWOCKZFERBP-UHFFFAOYSA-N 0.000 claims 2
- VDCSSTMOVRAAQF-UHFFFAOYSA-N n-[1-(3,3-dimethylbutyl)piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCC(C)(C)C)CC1)CC1=CC=C(C)C=C1 VDCSSTMOVRAAQF-UHFFFAOYSA-N 0.000 claims 2
- LEJDYGPQBCLZAQ-UHFFFAOYSA-N n-[1-(3-hydroxypropyl)piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCCO)CC1)CC1=CC=C(C)C=C1 LEJDYGPQBCLZAQ-UHFFFAOYSA-N 0.000 claims 2
- DXAHQNPHECHHGE-UHFFFAOYSA-N n-[1-(cyclohexylmethyl)piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC2CCCCC2)CC1)CC1=CC=C(C)C=C1 DXAHQNPHECHHGE-UHFFFAOYSA-N 0.000 claims 2
- PPWGILVXHPWTRW-UHFFFAOYSA-N n-[1-(cyclopentylmethyl)piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC2CCCC2)CC1)CC1=CC=C(C)C=C1 PPWGILVXHPWTRW-UHFFFAOYSA-N 0.000 claims 2
- UHELCGNCDRUIFE-UHFFFAOYSA-N n-[1-[(2-hydroxyphenyl)methyl]piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC=2C(=CC=CC=2)O)CC1)CC1=CC=C(C)C=C1 UHELCGNCDRUIFE-UHFFFAOYSA-N 0.000 claims 2
- YTEQQOOYLOKQBV-UHFFFAOYSA-N n-[1-[(5-chloro-1-benzothiophen-3-yl)methyl]piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC=2C3=CC(Cl)=CC=C3SC=2)CC1)CC1=CC=C(C)C=C1 YTEQQOOYLOKQBV-UHFFFAOYSA-N 0.000 claims 2
- LTXOMGATBUWTBV-UHFFFAOYSA-N n-[1-[(5-chlorothiophen-2-yl)methyl]piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC=2SC(Cl)=CC=2)CC1)CC1=CC=C(C)C=C1 LTXOMGATBUWTBV-UHFFFAOYSA-N 0.000 claims 2
- XQAILATXMJPLDO-UHFFFAOYSA-N n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-2-[4-(2-fluoroethoxy)phenyl]-n-[(4-fluorophenyl)methyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCCF)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CC1=CC=C(F)C=C1 XQAILATXMJPLDO-UHFFFAOYSA-N 0.000 claims 2
- YHPXZAQALSNWKB-UHFFFAOYSA-N n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-(4-propan-2-yloxyphenyl)acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OC(C)C)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CC1=CC=C(F)C=C1 YHPXZAQALSNWKB-UHFFFAOYSA-N 0.000 claims 2
- NTJOPEHCAXUPEP-UHFFFAOYSA-N n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CC1=CC=C(F)C=C1 NTJOPEHCAXUPEP-UHFFFAOYSA-N 0.000 claims 2
- ORODYUWQXLWWQB-UHFFFAOYSA-N n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-phenylacetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(F)=CC=C1CN(C(=O)CC=1C=CC=CC=1)C1CCN(CCC2OCCCO2)CC1 ORODYUWQXLWWQB-UHFFFAOYSA-N 0.000 claims 2
- VWZNADOHUGIIBK-UHFFFAOYSA-N n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[2-(4-fluorophenyl)ethyl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CCC1=CC=C(F)C=C1 VWZNADOHUGIIBK-UHFFFAOYSA-N 0.000 claims 2
- FMFORDPNRSJERU-UHFFFAOYSA-N n-[1-[2-(2,4-dioxo-1h-quinazolin-3-yl)ethyl]piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1)CC1=CC=C(C)C=C1 FMFORDPNRSJERU-UHFFFAOYSA-N 0.000 claims 2
- KYVHLTBRDGZPBW-UHFFFAOYSA-N n-[1-[2-(2,4-dioxo-1h-quinazolin-3-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-(4-propan-2-yloxyphenyl)acetamide;hydrochloride Chemical compound Cl.C1=CC(OC(C)C)=CC=C1CC(=O)N(C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1)CC1=CC=C(F)C=C1 KYVHLTBRDGZPBW-UHFFFAOYSA-N 0.000 claims 2
- DTMWBOFADDNFHF-UHFFFAOYSA-N n-[1-[2-(4,6-dimethyl-1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCC2OC(C)CC(C)O2)CC1)CC1=CC=C(F)C=C1 DTMWBOFADDNFHF-UHFFFAOYSA-N 0.000 claims 2
- XZVKALAUJZNXTI-UHFFFAOYSA-N n-[1-[3-(2,5-dimethylpyrrolidin-1-yl)propyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2C(CCC2C)C)CC1)CC1=CC=C(F)C=C1 XZVKALAUJZNXTI-UHFFFAOYSA-N 0.000 claims 2
- XBCVEOZEEBQAGM-UHFFFAOYSA-N n-[1-[[4-(chloromethyl)-1,3-thiazol-2-yl]methyl]piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC=2SC=C(CCl)N=2)CC1)CC1=CC=C(C)C=C1 XBCVEOZEEBQAGM-UHFFFAOYSA-N 0.000 claims 2
- VHXNQBYZMCIFAP-UHFFFAOYSA-N n-[2-(2,5-dimethoxyphenyl)ethyl]-2-(4-methoxyphenyl)-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(C)CC1)CCC1=CC(OC)=CC=C1OC VHXNQBYZMCIFAP-UHFFFAOYSA-N 0.000 claims 2
- IQQQWYZXENKNNG-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-2-(4-methoxyphenyl)-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(C)CC1)CCC1=CC=CC(Cl)=C1 IQQQWYZXENKNNG-UHFFFAOYSA-N 0.000 claims 2
- RRSHDOQUGYBNAZ-RYWNGCACSA-N n-[2-(4-fluorophenyl)ethyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-[3-[(4s)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]propyl]piperidin-4-yl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2C(OC[C@@H]2C(C)C)=O)CC1)CCC1=CC=C(F)C=C1 RRSHDOQUGYBNAZ-RYWNGCACSA-N 0.000 claims 2
- UNHGSHHVDNGCFN-UHFFFAOYSA-N naratriptan Chemical compound C=12[CH]C(CCS(=O)(=O)NC)=CC=C2N=CC=1C1CCN(C)CC1 UNHGSHHVDNGCFN-UHFFFAOYSA-N 0.000 claims 2
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 claims 2
- TXHZXHICDBAVJW-UHFFFAOYSA-N rizatriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1CN1C=NC=N1 TXHZXHICDBAVJW-UHFFFAOYSA-N 0.000 claims 2
- UIVFDCIXTSJXBB-ITGUQSILSA-N tropisetron Chemical compound C1=CC=C[C]2C(C(=O)O[C@H]3C[C@H]4CC[C@@H](C3)N4C)=CN=C21 UIVFDCIXTSJXBB-ITGUQSILSA-N 0.000 claims 2
- UTAZCRNOSWWEFR-ZDUSSCGKSA-N zolmitriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1C[C@H]1COC(=O)N1 UTAZCRNOSWWEFR-ZDUSSCGKSA-N 0.000 claims 2
- LXUQQSXLJDEALP-VIFPVBQESA-N (s)-(+)-1-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole Chemical compound O1CCCC2=C1C=CC1=NC=C(C[C@@H](N)C)[C]21 LXUQQSXLJDEALP-VIFPVBQESA-N 0.000 claims 1
- WQSACWZKKZPCHN-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutan-1-amine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N)CC(C)C)CCC1 WQSACWZKKZPCHN-UHFFFAOYSA-N 0.000 claims 1
- UDFLAKOWZDLLLS-UHFFFAOYSA-N 1-[2-(1,3-dioxan-2-yl)ethyl]-n-[(4-fluorophenyl)methyl]piperidin-4-amine Chemical compound C1=CC(F)=CC=C1CNC1CCN(CCC2OCCCO2)CC1 UDFLAKOWZDLLLS-UHFFFAOYSA-N 0.000 claims 1
- CBTITARLOCZPDU-UHFFFAOYSA-N 1h-indole-2-carbonitrile Chemical compound C1=CC=C2NC(C#N)=CC2=C1 CBTITARLOCZPDU-UHFFFAOYSA-N 0.000 claims 1
- CKURHQVZCQPEIC-YCBFMBTMSA-N 2,3-dihydroxybutanedioic acid;n-[1-[(3s)-3,5-dihydroxypentyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CC[C@H](O)CCO)CC1)CC1=CC=C(F)C=C1 CKURHQVZCQPEIC-YCBFMBTMSA-N 0.000 claims 1
- CLJWQSVHQZVXPM-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-(4-propan-2-ylphenyl)acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(C(C)C)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CC1=CC=C(F)C=C1 CLJWQSVHQZVXPM-UHFFFAOYSA-N 0.000 claims 1
- HJICAELANBGCJL-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[2-(1,3-dioxolan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-(4-propoxyphenyl)acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCCC)=CC=C1CC(=O)N(C1CCN(CCC2OCCO2)CC1)CC1=CC=C(F)C=C1 HJICAELANBGCJL-UHFFFAOYSA-N 0.000 claims 1
- AHWSVBQMUPQYGP-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[1-[3-(1,3-dioxolan-2-yl)propyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCC2OCCO2)CC1)CC1=CC=C(F)C=C1 AHWSVBQMUPQYGP-UHFFFAOYSA-N 0.000 claims 1
- SSQXVJRDGNCXMQ-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-5-yl)-n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]acetamide;2,3-dihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC(F)=CC=C1CN(C(=O)CC=1C=C2CCOC2=CC=1)C1CCN(CCC2OCCCO2)CC1 SSQXVJRDGNCXMQ-UHFFFAOYSA-N 0.000 claims 1
- KNWVEWAUNSDKOI-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[(4-methylphenyl)methyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)N(C1CCN(C)CC1)CC1=CC=C(C)C=C1 KNWVEWAUNSDKOI-UHFFFAOYSA-N 0.000 claims 1
- OTAFNQWZPPACJJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(1-cyclobutylpiperidin-4-yl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(C)=CC=C1CN(C(=O)CC=1C=CC(Cl)=CC=1)C1CCN(C2CCC2)CC1 OTAFNQWZPPACJJ-UHFFFAOYSA-N 0.000 claims 1
- FSJLQULBGMXJCH-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(1-cyclopentylpiperidin-4-yl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(C)=CC=C1CN(C(=O)CC=1C=CC(Cl)=CC=1)C1CCN(C2CCCC2)CC1 FSJLQULBGMXJCH-UHFFFAOYSA-N 0.000 claims 1
- VJNIYBQKMSKIAH-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[(4-methoxyphenyl)methyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CN(C(=O)CC=1C=CC(F)=CC=1)C1CCN(C)CC1 VJNIYBQKMSKIAH-UHFFFAOYSA-N 0.000 claims 1
- DBBBRJCDQZKMME-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(3-phenylpropyl)-n-piperidin-4-ylacetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCNCC1)CCCC1=CC=CC=C1 DBBBRJCDQZKMME-UHFFFAOYSA-N 0.000 claims 1
- IPUVIOXGEXOXFP-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methoxyphenyl)methyl]-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CN(C(=O)CC=1C=CC(OC)=CC=1)C1CCN(C)CC1 IPUVIOXGEXOXFP-UHFFFAOYSA-N 0.000 claims 1
- NOYNZXDOFBLXBN-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-(1-propan-2-ylpiperidin-4-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC1)C(C)C)CC1=CC=C(C)C=C1 NOYNZXDOFBLXBN-UHFFFAOYSA-N 0.000 claims 1
- ZGDJQKGPIBHKFJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-(1-propylpiperidin-4-yl)acetamide Chemical compound C1CN(CCC)CCC1N(C(=O)CC=1C=CC(OC)=CC=1)CC1=CC=C(C)C=C1 ZGDJQKGPIBHKFJ-UHFFFAOYSA-N 0.000 claims 1
- OZDHQDKSHGOMFO-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-[1-[(4-methylphenyl)methyl]piperidin-4-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC=2C=CC(C)=CC=2)CC1)CC1=CC=C(C)C=C1 OZDHQDKSHGOMFO-UHFFFAOYSA-N 0.000 claims 1
- SKILQDUJEYMUQT-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-[1-[2-(2-oxoimidazolidin-1-yl)ethyl]piperidin-4-yl]acetamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCN2C(NCC2)=O)CC1)CC1=CC=C(C)C=C1 SKILQDUJEYMUQT-UHFFFAOYSA-N 0.000 claims 1
- BIQKQLXPABLVDY-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-[1-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]piperidin-4-yl]acetamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCCN2C(NC3=CC=CC=C32)=O)CC1)CC1=CC=C(C)C=C1 BIQKQLXPABLVDY-UHFFFAOYSA-N 0.000 claims 1
- PBLGGRLPIOFLNE-UHFFFAOYSA-N 3-[(4-ethoxyphenyl)methyl]-4-[(4-fluorophenyl)methyl]-8-methyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC)=CC=C1CN1C(=O)OC2(CCN(C)CC2)C1CC1=CC=C(F)C=C1 PBLGGRLPIOFLNE-UHFFFAOYSA-N 0.000 claims 1
- HFUMDEFFVVRFOL-UHFFFAOYSA-N 3-[[1-[2-(6-chloro-2-oxo-1,3-dihydroindol-5-yl)ethyl]pyrrolidin-3-yl]methyl]-1h-indole-5-carbonitrile;hydrochloride Chemical compound Cl.C1=C(C#N)C=C2C(CC3CCN(C3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=CNC2=C1 HFUMDEFFVVRFOL-UHFFFAOYSA-N 0.000 claims 1
- IHUPGFLVWMCFQA-UHFFFAOYSA-N 3-[[4-(cyclopropylmethoxy)phenyl]methyl]-4-[(4-fluorophenyl)methyl]-8-[2-(2-oxoimidazolidin-1-yl)ethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(F)=CC=C1CC1C2(CCN(CCN3C(NCC3)=O)CC2)OC(=O)N1CC(C=C1)=CC=C1OCC1CC1 IHUPGFLVWMCFQA-UHFFFAOYSA-N 0.000 claims 1
- DGOCVISYYYQFEP-UHFFFAOYSA-N 4,4-dimethyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]piperidine-2,6-dione;hydron;chloride Chemical compound Cl.O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 DGOCVISYYYQFEP-UHFFFAOYSA-N 0.000 claims 1
- GHOUMPGWWZFZHH-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-8-[2-(2-oxoimidazolidin-1-yl)ethyl]-3-[(4-propoxyphenyl)methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCCC)=CC=C1CN1C(=O)OC2(CCN(CCN3C(NCC3)=O)CC2)C1CC1=CC=C(F)C=C1 GHOUMPGWWZFZHH-UHFFFAOYSA-N 0.000 claims 1
- FUUOKEAEJPTHHD-UHFFFAOYSA-N 8-(cyclopropylmethyl)-4-[(4-fluorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CN1C(=O)OC2(CCN(CC3CC3)CC2)C1CC1=CC=C(F)C=C1 FUUOKEAEJPTHHD-UHFFFAOYSA-N 0.000 claims 1
- MQBRJALDRPYTNB-UHFFFAOYSA-N 8-ethyl-4-[(4-fluorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CN(CC)CCC21C(CC=1C=CC(F)=CC=1)N(CC=1C=CC(OCC(C)C)=CC=1)C(=O)O2 MQBRJALDRPYTNB-UHFFFAOYSA-N 0.000 claims 1
- LADKOBQJOCFCQU-FPOVZHCZSA-N FC(F)(F)C1=CC(OC(C)C)=CC=C1C1=CC([C@H]2[C@H](CCNC2)N2CCCO3)=C2C3=C1 Chemical compound FC(F)(F)C1=CC(OC(C)C)=CC=C1C1=CC([C@H]2[C@H](CCNC2)N2CCCO3)=C2C3=C1 LADKOBQJOCFCQU-FPOVZHCZSA-N 0.000 claims 1
- 229940109239 creatinine Drugs 0.000 claims 1
- MEZAUIMSMPNHOK-UHFFFAOYSA-N methyl 1-[3-[4-[(4-fluorophenyl)methyl-[2-[4-(2-methylpropoxy)phenyl]acetyl]amino]piperidin-1-yl]propyl]piperidine-4-carboxylate;dihydrochloride Chemical compound Cl.Cl.C1CC(C(=O)OC)CCN1CCCN1CCC(N(CC=2C=CC(F)=CC=2)C(=O)CC=2C=CC(OCC(C)C)=CC=2)CC1 MEZAUIMSMPNHOK-UHFFFAOYSA-N 0.000 claims 1
- UUKTZPFWRWUEOE-UHFFFAOYSA-N n-(1-butylpiperidin-4-yl)-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1CN(CCCC)CCC1N(C(=O)CC=1C=CC(OC)=CC=1)CC1=CC=C(C)C=C1 UUKTZPFWRWUEOE-UHFFFAOYSA-N 0.000 claims 1
- XZWMIKRQUCRJMJ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-(4-methoxyphenyl)-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(C)CC1)CC1=CC=C(F)C=C1 XZWMIKRQUCRJMJ-UHFFFAOYSA-N 0.000 claims 1
- DQXSITRGGNQAPY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-(3-morpholin-4-ylpropyl)piperidin-4-yl]acetamide Chemical compound C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2CCOCC2)CC1)CC1=CC=C(F)C=C1 DQXSITRGGNQAPY-UHFFFAOYSA-N 0.000 claims 1
- YQVPZCRVGFVSSM-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-(3-morpholin-4-ylpropyl)piperidin-4-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2CCOCC2)CC1)CC1=CC=C(F)C=C1 YQVPZCRVGFVSSM-UHFFFAOYSA-N 0.000 claims 1
- BHSQMVYQZAYDFD-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-[3-(2-oxopiperidin-1-yl)propyl]piperidin-4-yl]acetamide Chemical compound C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2C(CCCC2)=O)CC1)CC1=CC=C(F)C=C1 BHSQMVYQZAYDFD-UHFFFAOYSA-N 0.000 claims 1
- YRTSIKARPYISSN-YNMZEGNTSA-N n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]-n-[1-[3-[(4r)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]propyl]piperidin-4-yl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2C(OC[C@H]2C(C)C)=O)CC1)CC1=CC=C(F)C=C1 YRTSIKARPYISSN-YNMZEGNTSA-N 0.000 claims 1
- HFHFVEQMFFFXGZ-KKBKUYFKSA-N n-[(4-fluorophenyl)methyl]-n-[1-[2-[(2r)-4-methyl-1,3-dioxan-2-yl]ethyl]piperidin-4-yl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CC[C@H]2OC(C)CCO2)CC1)CC1=CC=C(F)C=C1 HFHFVEQMFFFXGZ-KKBKUYFKSA-N 0.000 claims 1
- NQGFPIWIMRVASF-PECUQCEBSA-N n-[(4-fluorophenyl)methyl]-n-[1-[2-[(2r)-4-methyl-1,3-dioxan-2-yl]ethyl]piperidin-4-yl]-2-[4-(trifluoromethoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.O1C(C)CCO[C@H]1CCN1CCC(N(CC=2C=CC(F)=CC=2)C(=O)CC=2C=CC(OC(F)(F)F)=CC=2)CC1 NQGFPIWIMRVASF-PECUQCEBSA-N 0.000 claims 1
- BCNWTNGPSAQFSY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-[1-[3-(3-methyl-2-oxobenzimidazol-1-yl)propyl]piperidin-4-yl]-2-(4-propan-2-yloxyphenyl)acetamide;hydrochloride Chemical compound Cl.C1=CC(OC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2C(N(C)C3=CC=CC=C32)=O)CC1)CC1=CC=C(F)C=C1 BCNWTNGPSAQFSY-UHFFFAOYSA-N 0.000 claims 1
- JZRFHXCNZAEMTM-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-n-(1-methylpiperidin-4-yl)-2-phenylacetamide Chemical compound C1=CC(OC)=CC=C1CN(C(=O)CC=1C=CC=CC=1)C1CCN(C)CC1 JZRFHXCNZAEMTM-UHFFFAOYSA-N 0.000 claims 1
- AFWHGJWFJWYLII-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]-n-(1-methylpiperidin-4-yl)-2-phenylbutanamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)N(C1CCN(C)CC1)CC1=CC=C(C)C=C1 AFWHGJWFJWYLII-UHFFFAOYSA-N 0.000 claims 1
- YFQJPYMIYDERMB-UHFFFAOYSA-N n-[1-(2-hydroxyethyl)piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCO)CC1)CC1=CC=C(C)C=C1 YFQJPYMIYDERMB-UHFFFAOYSA-N 0.000 claims 1
- TXHLTEVKXKTMMX-UHFFFAOYSA-N n-[1-(cyclobutylmethyl)piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC2CCC2)CC1)CC1=CC=C(C)C=C1 TXHLTEVKXKTMMX-UHFFFAOYSA-N 0.000 claims 1
- OYDOPBLBZFBHFF-UHFFFAOYSA-N n-[1-[(4-hydroxyphenyl)methyl]piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CC=2C=CC(O)=CC=2)CC1)CC1=CC=C(C)C=C1 OYDOPBLBZFBHFF-UHFFFAOYSA-N 0.000 claims 1
- IPZZBUSUXOQWOD-UHFFFAOYSA-N n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-2-(4-ethoxyphenyl)-n-[(4-fluorophenyl)methyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CC1=CC=C(F)C=C1 IPZZBUSUXOQWOD-UHFFFAOYSA-N 0.000 claims 1
- HGRHFHIAKYPMOI-UHFFFAOYSA-N n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-(4-propan-2-ylphenyl)acetamide Chemical compound C1=CC(C(C)C)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CC1=CC=C(F)C=C1 HGRHFHIAKYPMOI-UHFFFAOYSA-N 0.000 claims 1
- YYXZVMHZOAXFEQ-UHFFFAOYSA-N n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[2-(4-fluorophenyl)ethyl]-2-(4-propoxyphenyl)acetamide Chemical compound C1=CC(OCCC)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CCC1=CC=C(F)C=C1 YYXZVMHZOAXFEQ-UHFFFAOYSA-N 0.000 claims 1
- WSXKFLIWGMGWLB-UHFFFAOYSA-N n-[1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[2-(4-fluorophenyl)ethyl]-2-(4-propoxyphenyl)acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCCC)=CC=C1CC(=O)N(C1CCN(CCC2OCCCO2)CC1)CCC1=CC=C(F)C=C1 WSXKFLIWGMGWLB-UHFFFAOYSA-N 0.000 claims 1
- WOCZWUJZUZXSIA-UHFFFAOYSA-N n-[1-[2-(1,3-dioxolan-2-yl)ethyl]piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCC2OCCO2)CC1)CC1=CC=C(C)C=C1 WOCZWUJZUZXSIA-UHFFFAOYSA-N 0.000 claims 1
- CWBQTYNZGDFNRZ-UHFFFAOYSA-N n-[1-[2-(1,3-dioxolan-2-yl)ethyl]piperidin-4-yl]-n-[(4-methylphenyl)methyl]-2-(4-propan-2-yloxyphenyl)acetamide;hydrochloride Chemical compound Cl.C1=CC(OC(C)C)=CC=C1CC(=O)N(C1CCN(CCC2OCCO2)CC1)CC1=CC=C(C)C=C1 CWBQTYNZGDFNRZ-UHFFFAOYSA-N 0.000 claims 1
- NZERYWOQMJPWRA-UHFFFAOYSA-N n-[1-[2-(2,4-dioxo-1h-quinazolin-3-yl)ethyl]piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1)CC1=CC=C(C)C=C1 NZERYWOQMJPWRA-UHFFFAOYSA-N 0.000 claims 1
- WGAGZAZIDZVUIZ-UHFFFAOYSA-N n-[1-[2-(2-hydroxyethoxy)ethyl]piperidin-4-yl]-2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCOCCO)CC1)CC1=CC=C(C)C=C1 WGAGZAZIDZVUIZ-UHFFFAOYSA-N 0.000 claims 1
- IRDJWKVKKVIDDY-UHFFFAOYSA-N n-[1-[2-(5,5-dimethyl-1,3-dioxan-2-yl)ethyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCC2OCC(C)(C)CO2)CC1)CC1=CC=C(F)C=C1 IRDJWKVKKVIDDY-UHFFFAOYSA-N 0.000 claims 1
- AJGCJZUYFZTULR-UHFFFAOYSA-N n-[1-[3-(2,6-dimethylmorpholin-4-yl)propyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2CC(C)OC(C)C2)CC1)CC1=CC=C(F)C=C1 AJGCJZUYFZTULR-UHFFFAOYSA-N 0.000 claims 1
- KFESCFBLQMTIOS-UHFFFAOYSA-N n-[1-[3-(2,6-dimethylmorpholin-4-yl)propyl]piperidin-4-yl]-n-[(4-fluorophenyl)methyl]-2-[4-(2-methylpropoxy)phenyl]acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.C1=CC(OCC(C)C)=CC=C1CC(=O)N(C1CCN(CCCN2CC(C)OC(C)C2)CC1)CC1=CC=C(F)C=C1 KFESCFBLQMTIOS-UHFFFAOYSA-N 0.000 claims 1
- UVXYHOCZJLSZEW-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-2-(4-methoxyphenyl)-n-(1-methylpiperidin-2-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1N(CCCC1)C)CCC1=CC=C(Cl)C=C1Cl UVXYHOCZJLSZEW-UHFFFAOYSA-N 0.000 claims 1
- VNMVBSZVZVECPG-UHFFFAOYSA-N n-[2-(3-fluorophenyl)ethyl]-2-(4-methoxyphenyl)-n-(1-methylpiperidin-4-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N(C1CCN(C)CC1)CCC1=CC=CC(F)=C1 VNMVBSZVZVECPG-UHFFFAOYSA-N 0.000 claims 1
- DLIHUOQEBDYNQS-JSSVAETHSA-N n-[2-(4-fluorophenyl)ethyl]-n-[1-[3-[(4s)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]propyl]piperidin-4-yl]-2-(4-propoxyphenyl)acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCCC)=CC=C1CC(=O)N(C1CCN(CCCN2C(OC[C@@H]2C(C)C)=O)CC1)CCC1=CC=C(F)C=C1 DLIHUOQEBDYNQS-JSSVAETHSA-N 0.000 claims 1
- BMGVVCPMFGMQEM-UHFFFAOYSA-N n-[3-[[5-[3-(2-aminoethyl)-1h-indol-5-yl]-1,2,4-oxadiazol-3-yl]methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(CC=2N=C(ON=2)C=2C=C3C(CCN)=CNC3=CC=2)=C1 BMGVVCPMFGMQEM-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 22
- 239000003814 drug Substances 0.000 abstract description 17
- 229940079593 drug Drugs 0.000 abstract description 14
- 230000003463 hyperproliferative effect Effects 0.000 abstract description 12
- 230000002195 synergetic effect Effects 0.000 abstract description 3
- 235000001014 amino acid Nutrition 0.000 description 41
- 229940024606 amino acid Drugs 0.000 description 40
- 210000004027 cell Anatomy 0.000 description 33
- 201000009030 Carcinoma Diseases 0.000 description 31
- 208000009956 adenocarcinoma Diseases 0.000 description 30
- 206010041823 squamous cell carcinoma Diseases 0.000 description 21
- 208000035475 disorder Diseases 0.000 description 15
- 241000700159 Rattus Species 0.000 description 14
- 229910052700 potassium Inorganic materials 0.000 description 13
- 102000005962 receptors Human genes 0.000 description 13
- 108020003175 receptors Proteins 0.000 description 13
- 125000003275 alpha amino acid group Chemical group 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 230000037396 body weight Effects 0.000 description 9
- 238000012217 deletion Methods 0.000 description 9
- 230000037430 deletion Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 201000008395 adenosquamous carcinoma Diseases 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 7
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 7
- 206010039491 Sarcoma Diseases 0.000 description 7
- 208000002458 carcinoid tumor Diseases 0.000 description 7
- 235000019197 fats Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 7
- 206010025323 Lymphomas Diseases 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 201000011066 hemangioma Diseases 0.000 description 6
- 201000010879 mucinous adenocarcinoma Diseases 0.000 description 6
- 150000002924 oxiranes Chemical class 0.000 description 6
- 208000010576 undifferentiated carcinoma Diseases 0.000 description 6
- 235000019786 weight gain Nutrition 0.000 description 6
- 208000003200 Adenoma Diseases 0.000 description 5
- 206010001233 Adenoma benign Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 230000032683 aging Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 208000009060 clear cell adenocarcinoma Diseases 0.000 description 5
- 239000012039 electrophile Substances 0.000 description 5
- 206010016256 fatigue Diseases 0.000 description 5
- 230000037406 food intake Effects 0.000 description 5
- 235000012631 food intake Nutrition 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 201000010260 leiomyoma Diseases 0.000 description 5
- 208000004019 papillary adenocarcinoma Diseases 0.000 description 5
- 230000004584 weight gain Effects 0.000 description 5
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 4
- 201000003076 Angiosarcoma Diseases 0.000 description 4
- 206010007275 Carcinoid tumour Diseases 0.000 description 4
- 208000001258 Hemangiosarcoma Diseases 0.000 description 4
- 102000008394 Immunoglobulin Fragments Human genes 0.000 description 4
- 108010021625 Immunoglobulin Fragments Proteins 0.000 description 4
- 206010024612 Lipoma Diseases 0.000 description 4
- 150000001718 carbodiimides Chemical class 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000003211 malignant effect Effects 0.000 description 4
- 201000001441 melanoma Diseases 0.000 description 4
- 239000012038 nucleophile Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 201000010198 papillary carcinoma Diseases 0.000 description 4
- 201000007416 salivary gland adenoid cystic carcinoma Diseases 0.000 description 4
- 208000000649 small cell carcinoma Diseases 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 201000007490 Adenocarcinoma in Situ Diseases 0.000 description 3
- 206010004146 Basal cell carcinoma Diseases 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 208000009458 Carcinoma in Situ Diseases 0.000 description 3
- 206010008263 Cervical dysplasia Diseases 0.000 description 3
- 208000005431 Endometrioid Carcinoma Diseases 0.000 description 3
- 201000009273 Endometriosis Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 201000008808 Fibrosarcoma Diseases 0.000 description 3
- 208000008999 Giant Cell Carcinoma Diseases 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
- 206010057269 Mucoepidermoid carcinoma Diseases 0.000 description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- 208000003252 Signet Ring Cell Carcinoma Diseases 0.000 description 3
- 244000269722 Thea sinensis Species 0.000 description 3
- 206010046798 Uterine leiomyoma Diseases 0.000 description 3
- 208000018777 Vulvar intraepithelial neoplasia Diseases 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 208000002517 adenoid cystic carcinoma Diseases 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 206010003119 arrhythmia Diseases 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 208000007951 cervical intraepithelial neoplasia Diseases 0.000 description 3
- 201000003505 cervical polyp Diseases 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 208000028730 endometrioid adenocarcinoma Diseases 0.000 description 3
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 description 3
- 230000003628 erosive effect Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 201000008361 ganglioneuroma Diseases 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000005179 haloacetyl group Chemical group 0.000 description 3
- 201000004933 in situ carcinoma Diseases 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 206010024627 liposarcoma Diseases 0.000 description 3
- 150000004668 long chain fatty acids Chemical class 0.000 description 3
- 201000000014 lung giant cell carcinoma Diseases 0.000 description 3
- 206010027191 meningioma Diseases 0.000 description 3
- 208000007106 menorrhagia Diseases 0.000 description 3
- 208000030159 metabolic disease Diseases 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 208000007538 neurilemmoma Diseases 0.000 description 3
- 230000002062 proliferating effect Effects 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 206010039667 schwannoma Diseases 0.000 description 3
- 201000008123 signet ring cell adenocarcinoma Diseases 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 206010044412 transitional cell carcinoma Diseases 0.000 description 3
- 201000007423 tubular adenocarcinoma Diseases 0.000 description 3
- 208000010579 uterine corpus leiomyoma Diseases 0.000 description 3
- 201000007954 uterine fibroid Diseases 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NGEWQZIDQIYUNV-UHFFFAOYSA-N 2-hydroxy-3-methylbutyric acid Chemical compound CC(C)C(O)C(O)=O NGEWQZIDQIYUNV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 208000003174 Brain Neoplasms Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- 108010074051 C-Reactive Protein Proteins 0.000 description 2
- 102100032752 C-reactive protein Human genes 0.000 description 2
- 208000003163 Cavernous Hemangioma Diseases 0.000 description 2
- 208000005243 Chondrosarcoma Diseases 0.000 description 2
- 206010010356 Congenital anomaly Diseases 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 208000032928 Dyslipidaemia Diseases 0.000 description 2
- 108010049003 Fibrinogen Proteins 0.000 description 2
- 102000008946 Fibrinogen Human genes 0.000 description 2
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 description 2
- 208000032612 Glial tumor Diseases 0.000 description 2
- 206010018338 Glioma Diseases 0.000 description 2
- 208000006050 Hemangiopericytoma Diseases 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 2
- 208000006937 Hydatidiform mole Diseases 0.000 description 2
- 206010022489 Insulin Resistance Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 208000007766 Kaposi sarcoma Diseases 0.000 description 2
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 238000008214 LDL Cholesterol Methods 0.000 description 2
- 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 2
- 208000018142 Leiomyosarcoma Diseases 0.000 description 2
- 208000017170 Lipid metabolism disease Diseases 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical class ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- 206010029098 Neoplasm skin Diseases 0.000 description 2
- 201000004404 Neurofibroma Diseases 0.000 description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 2
- 208000001388 Opportunistic Infections Diseases 0.000 description 2
- 108010022233 Plasminogen Activator Inhibitor 1 Proteins 0.000 description 2
- 102100039418 Plasminogen activator inhibitor 1 Human genes 0.000 description 2
- 208000006265 Renal cell carcinoma Diseases 0.000 description 2
- 201000000582 Retinoblastoma Diseases 0.000 description 2
- 208000000453 Skin Neoplasms Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 206010068771 Soft tissue neoplasm Diseases 0.000 description 2
- 208000003734 Supraventricular Tachycardia Diseases 0.000 description 2
- 206010043276 Teratoma Diseases 0.000 description 2
- 206010045515 Undifferentiated sarcoma Diseases 0.000 description 2
- 208000006336 acinar cell carcinoma Diseases 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000036528 appetite Effects 0.000 description 2
- 235000019789 appetite Nutrition 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 229940009098 aspartate Drugs 0.000 description 2
- 230000000923 atherogenic effect Effects 0.000 description 2
- 150000001541 aziridines Chemical class 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 208000027804 carcinoma ex pleomorphic adenoma Diseases 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000032823 cell division Effects 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 210000000795 conjunctiva Anatomy 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- RHJVIGLEIFVHIJ-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1[CH]CCCC1 RHJVIGLEIFVHIJ-UHFFFAOYSA-N 0.000 description 2
- 208000002445 cystadenocarcinoma Diseases 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- 201000002893 dermoid cyst of ovary Diseases 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 201000003908 endometrial adenocarcinoma Diseases 0.000 description 2
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 description 2
- 210000003238 esophagus Anatomy 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229940012952 fibrinogen Drugs 0.000 description 2
- 206010016629 fibroma Diseases 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- LVJJFMLUMNSUFN-UHFFFAOYSA-N gallocatechin gallate Natural products C1=C(O)C=C2OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C1OC(=O)C1=CC(O)=C(O)C(O)=C1 LVJJFMLUMNSUFN-UHFFFAOYSA-N 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 229940049906 glutamate Drugs 0.000 description 2
- 229930195712 glutamate Natural products 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002463 imidates Chemical class 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 201000006747 infectious mononucleosis Diseases 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 230000002452 interceptive effect Effects 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 206010073095 invasive ductal breast carcinoma Diseases 0.000 description 2
- 206010073096 invasive lobular breast carcinoma Diseases 0.000 description 2
- RGFNRWTWDWVHDD-UHFFFAOYSA-N isobutyl butyrate Chemical compound CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 206010061526 malignant mesenchymoma Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 208000004707 mucinous cystadenoma Diseases 0.000 description 2
- 208000009091 myxoma Diseases 0.000 description 2
- 210000005170 neoplastic cell Anatomy 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 201000010302 ovarian serous cystadenocarcinoma Diseases 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 201000001494 papillary transitional carcinoma Diseases 0.000 description 2
- 208000031101 papillary transitional cell carcinoma Diseases 0.000 description 2
- 239000004031 partial agonist Substances 0.000 description 2
- JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 description 2
- 150000004885 piperazines Chemical class 0.000 description 2
- 201000009307 pleomorphic adenoma carcinoma Diseases 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000000770 proinflammatory effect Effects 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 230000003331 prothrombotic effect Effects 0.000 description 2
- 206010037844 rash Diseases 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 2
- 208000004548 serous cystadenocarcinoma Diseases 0.000 description 2
- 208000005893 serous cystadenoma Diseases 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 210000004872 soft tissue Anatomy 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000012453 sprague-dawley rat model Methods 0.000 description 2
- 208000022159 squamous carcinoma in situ Diseases 0.000 description 2
- 238000007619 statistical method Methods 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 208000025421 tumor of uterus Diseases 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 208000022810 undifferentiated (embryonal) sarcoma Diseases 0.000 description 2
- 210000003932 urinary bladder Anatomy 0.000 description 2
- 206010046766 uterine cancer Diseases 0.000 description 2
- 206010047302 ventricular tachycardia Diseases 0.000 description 2
- 208000008662 verrucous carcinoma Diseases 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- XMOCLSLCDHWDHP-SWLSCSKDSA-N (+)-Epigallocatechin Natural products C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-SWLSCSKDSA-N 0.000 description 1
- DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 1
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- LSHVYAFMTMFKBA-PZJWPPBQSA-N (+)-catechin-3-O-gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-PZJWPPBQSA-N 0.000 description 1
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 description 1
- WMBWREPUVVBILR-GHTZIAJQSA-N (+)-gallocatechin gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-GHTZIAJQSA-N 0.000 description 1
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 description 1
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 description 1
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 description 1
- NVKZKCWZPSNZFD-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) carbonochloridate Chemical compound ClC(=O)ON1C(=O)CCC1=O NVKZKCWZPSNZFD-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- IEFRBBIKYDPZCO-SVLLLCHKSA-N (6ar,10ar)-4,5,5a,6,6a,7,8,9,10,10a-decahydroindolo[4,3-fg]quinoline Chemical class C([C@@H]12)CCN[C@@H]1CC1CNC3=CC=CC2=C31 IEFRBBIKYDPZCO-SVLLLCHKSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- GGKADXREVJTZMF-UHFFFAOYSA-N 1-Phenylethyl butyrate Chemical compound CCCC(=O)OC(C)C1=CC=CC=C1 GGKADXREVJTZMF-UHFFFAOYSA-N 0.000 description 1
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical class C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- LQGLKWIXYWZNGB-UHFFFAOYSA-N 1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical class O1C(=O)NCC11CCNCC1 LQGLKWIXYWZNGB-UHFFFAOYSA-N 0.000 description 1
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical class C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
- IVCGJOSPVGENCT-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline Chemical class N1=CC=CC2=C(NC=C3)C3=CC=C21 IVCGJOSPVGENCT-UHFFFAOYSA-N 0.000 description 1
- DPTWORPMSGTYRE-UHFFFAOYSA-N 2,3,3a,4-tetrahydrobenzo[g]indol-1-amine Chemical class C1=CC=CC2=C3N(N)CCC3CC=C21 DPTWORPMSGTYRE-UHFFFAOYSA-N 0.000 description 1
- HZNQSWJZTWOTKM-UHFFFAOYSA-N 2,3,4-trimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1OC HZNQSWJZTWOTKM-UHFFFAOYSA-N 0.000 description 1
- 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- HCGFLVDMFDHYJD-UHFFFAOYSA-N 2-piperazin-1-ylpyrazine Chemical class C1CNCCN1C1=CN=CC=N1 HCGFLVDMFDHYJD-UHFFFAOYSA-N 0.000 description 1
- HNQZRUDJRPSFAU-UHFFFAOYSA-N 2-piperidin-1-yl-1h-indole Chemical class C1CCCCN1C1=CC2=CC=CC=C2N1 HNQZRUDJRPSFAU-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 1
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 1
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 1
- 102100024956 5-hydroxytryptamine receptor 2B Human genes 0.000 description 1
- 101710138092 5-hydroxytryptamine receptor 2B Proteins 0.000 description 1
- 102100040368 5-hydroxytryptamine receptor 6 Human genes 0.000 description 1
- 101710150235 5-hydroxytryptamine receptor 6 Proteins 0.000 description 1
- 102100039126 5-hydroxytryptamine receptor 7 Human genes 0.000 description 1
- 101710150237 5-hydroxytryptamine receptor 7 Proteins 0.000 description 1
- ODHCTXKNWHHXJC-VKHMYHEASA-M 5-oxo-L-prolinate Chemical compound [O-]C(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-M 0.000 description 1
- QICJCIJONCDCML-UHFFFAOYSA-N 7,10-diazatetracyclo[8.6.1.05,17.011,16]heptadeca-1,3,5(17),6,8,11,13,15-octaene Chemical class C1=NC=CN2C3=CC=CC=C3C3=CC=CC1=C32 QICJCIJONCDCML-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 208000004611 Abdominal Obesity Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000001783 Adamantinoma Diseases 0.000 description 1
- 102000009346 Adenosine receptors Human genes 0.000 description 1
- 108050000203 Adenosine receptors Proteins 0.000 description 1
- 208000037540 Alveolar soft tissue sarcoma Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000003120 Angiofibroma Diseases 0.000 description 1
- 102000008873 Angiotensin II receptor Human genes 0.000 description 1
- 108050000824 Angiotensin II receptor Proteins 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 206010003571 Astrocytoma Diseases 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 206010003662 Atrial flutter Diseases 0.000 description 1
- 208000006808 Atrioventricular Nodal Reentry Tachycardia Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
- 208000031648 Body Weight Changes Diseases 0.000 description 1
- 208000018084 Bone neoplasm Diseases 0.000 description 1
- 108050001736 Bradykinin receptor Proteins 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000007690 Brenner tumor Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 208000003170 Bronchiolo-Alveolar Adenocarcinoma Diseases 0.000 description 1
- 206010058354 Bronchioloalveolar carcinoma Diseases 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 102000018208 Cannabinoid Receptor Human genes 0.000 description 1
- 108050007331 Cannabinoid receptor Proteins 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010065941 Central obesity Diseases 0.000 description 1
- 206010061809 Cervix carcinoma stage 0 Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 108010089448 Cholecystokinin B Receptor Proteins 0.000 description 1
- 108010009685 Cholinergic Receptors Proteins 0.000 description 1
- 208000010126 Chondromatosis Diseases 0.000 description 1
- 201000009047 Chordoma Diseases 0.000 description 1
- 208000006332 Choriocarcinoma Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010073140 Clear cell sarcoma of soft tissue Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 208000013440 Complete hydatidiform mole Diseases 0.000 description 1
- 208000009738 Connective Tissue Neoplasms Diseases 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- 206010059352 Desmoid tumour Diseases 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 108050004812 Dopamine receptor Proteins 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- 208000006402 Ductal Carcinoma Diseases 0.000 description 1
- LSHVYAFMTMFKBA-UHFFFAOYSA-N ECG Natural products C=1C=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-UHFFFAOYSA-N 0.000 description 1
- 201000009051 Embryonal Carcinoma Diseases 0.000 description 1
- 102000010180 Endothelin receptor Human genes 0.000 description 1
- 108050001739 Endothelin receptor Proteins 0.000 description 1
- 206010014967 Ependymoma Diseases 0.000 description 1
- 201000005231 Epithelioid sarcoma Diseases 0.000 description 1
- 208000006168 Ewing Sarcoma Diseases 0.000 description 1
- 201000003364 Extraskeletal myxoid chondrosarcoma Diseases 0.000 description 1
- 108010060374 FSH Receptors Proteins 0.000 description 1
- 102000008175 FSH Receptors Human genes 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000007659 Fibroadenoma Diseases 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 108700012941 GNRH1 Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- 102000011392 Galanin receptor Human genes 0.000 description 1
- 108050001605 Galanin receptor Proteins 0.000 description 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 description 1
- 208000000321 Gardner Syndrome Diseases 0.000 description 1
- 102000052874 Gastrin receptors Human genes 0.000 description 1
- 208000000527 Germinoma Diseases 0.000 description 1
- 208000007569 Giant Cell Tumors Diseases 0.000 description 1
- 201000005409 Gliomatosis cerebri Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 108010063919 Glucagon Receptors Proteins 0.000 description 1
- 102100040890 Glucagon receptor Human genes 0.000 description 1
- 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 1
- 102000018899 Glutamate Receptors Human genes 0.000 description 1
- 108010027915 Glutamate Receptors Proteins 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 206010060980 Granular cell tumour Diseases 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 208000002125 Hemangioendothelioma Diseases 0.000 description 1
- 206010019629 Hepatic adenoma Diseases 0.000 description 1
- 206010019695 Hepatic neoplasm Diseases 0.000 description 1
- 206010020118 Histiocytoses Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 241001502974 Human gammaherpesvirus 8 Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 206010020648 Hyperkeratoses Diseases 0.000 description 1
- 206010061246 Intervertebral disc degeneration Diseases 0.000 description 1
- 208000009164 Islet Cell Adenoma Diseases 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- 208000002260 Keloid Diseases 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- 108010011942 LH Receptors Proteins 0.000 description 1
- 102000023108 LH Receptors Human genes 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 206010023856 Laryngeal squamous cell carcinoma Diseases 0.000 description 1
- DBGIVFWFUFKIQN-SECBINFHSA-N Levofenfluramine Chemical compound CCN[C@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-SECBINFHSA-N 0.000 description 1
- 208000002404 Liver Cell Adenoma Diseases 0.000 description 1
- 208000000265 Lobular Carcinoma Diseases 0.000 description 1
- 206010073099 Lobular breast carcinoma in situ Diseases 0.000 description 1
- 201000002171 Luteoma Diseases 0.000 description 1
- 208000008771 Lymphadenopathy Diseases 0.000 description 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 208000006644 Malignant Fibrous Histiocytoma Diseases 0.000 description 1
- 208000007369 Malignant Mixed Tumor Diseases 0.000 description 1
- 206010025566 Malignant haemangiopericytoma Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 208000007054 Medullary Carcinoma Diseases 0.000 description 1
- 208000000172 Medulloblastoma Diseases 0.000 description 1
- 206010027145 Melanocytic naevus Diseases 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 102000018697 Membrane Proteins Human genes 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 201000009574 Mesenchymal Chondrosarcoma Diseases 0.000 description 1
- 206010070665 Mesoblastic nephroma Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 description 1
- 208000007182 Myelolipoma Diseases 0.000 description 1
- 208000014767 Myeloproliferative disease Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 description 1
- 206010029260 Neuroblastoma Diseases 0.000 description 1
- 108050002826 Neuropeptide Y Receptor Proteins 0.000 description 1
- 102000012301 Neuropeptide Y receptor Human genes 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 201000010133 Oligodendroglioma Diseases 0.000 description 1
- 108700020796 Oncogene Proteins 0.000 description 1
- 102000003840 Opioid Receptors Human genes 0.000 description 1
- 108090000137 Opioid Receptors Proteins 0.000 description 1
- 208000004179 Oral Leukoplakia Diseases 0.000 description 1
- 208000010191 Osteitis Deformans Diseases 0.000 description 1
- 208000000035 Osteochondroma Diseases 0.000 description 1
- 206010033236 Ovarian germ cell teratoma benign Diseases 0.000 description 1
- 102000004279 Oxytocin receptors Human genes 0.000 description 1
- 108090000876 Oxytocin receptors Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000027067 Paget disease of bone Diseases 0.000 description 1
- 208000025618 Paget disease of nipple Diseases 0.000 description 1
- 208000024024 Paget disease of the nipple Diseases 0.000 description 1
- 208000025610 Paget disease of the vulva Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 102000006461 Parathyroid Hormone Receptors Human genes 0.000 description 1
- 108010058828 Parathyroid Hormone Receptors Proteins 0.000 description 1
- 206010033963 Parathyroid tumour Diseases 0.000 description 1
- 208000013438 Partial hydatidiform mole Diseases 0.000 description 1
- 208000031481 Pathologic Constriction Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 108700023400 Platelet-activating factor receptors Proteins 0.000 description 1
- 206010035603 Pleural mesothelioma Diseases 0.000 description 1
- 208000005384 Pneumocystis Pneumonia Diseases 0.000 description 1
- 206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 208000015634 Rectal Neoplasms Diseases 0.000 description 1
- 102000016983 Releasing hormones receptors Human genes 0.000 description 1
- 208000005678 Rhabdomyoma Diseases 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 108050001286 Somatostatin Receptor Proteins 0.000 description 1
- 102000011096 Somatostatin receptor Human genes 0.000 description 1
- 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 description 1
- 208000036844 Squamous cell carcinoma of the larynx Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 206010042658 Sweat gland tumour Diseases 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 108010017842 Telomerase Proteins 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 208000000728 Thymus Neoplasms Diseases 0.000 description 1
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- 102000004852 Thyrotropin-releasing hormone receptors Human genes 0.000 description 1
- 108090001094 Thyrotropin-releasing hormone receptors Proteins 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 108700025716 Tumor Suppressor Genes Proteins 0.000 description 1
- 102000044209 Tumor Suppressor Genes Human genes 0.000 description 1
- 208000015778 Undifferentiated pleomorphic sarcoma Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 206010049060 Vascular Graft Occlusion Diseases 0.000 description 1
- 102000004136 Vasopressin Receptors Human genes 0.000 description 1
- 108090000643 Vasopressin Receptors Proteins 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- 208000008383 Wilms tumor Diseases 0.000 description 1
- 201000008803 Wolff-Parkinson-white syndrome Diseases 0.000 description 1
- 206010048214 Xanthoma Diseases 0.000 description 1
- 206010048215 Xanthomatosis Diseases 0.000 description 1
- 208000012018 Yolk sac tumor Diseases 0.000 description 1
- 229940124532 absorption promoter Drugs 0.000 description 1
- 102000034337 acetylcholine receptors Human genes 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
- 201000000452 adenoid squamous cell carcinoma Diseases 0.000 description 1
- 208000021096 adenomatous colon polyp Diseases 0.000 description 1
- 208000018234 adnexal spiradenoma/cylindroma of a sweat gland Diseases 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 208000026565 adrenal gland myelolipoma Diseases 0.000 description 1
- 208000024447 adrenal gland neoplasm Diseases 0.000 description 1
- 201000003352 adrenal gland pheochromocytoma Diseases 0.000 description 1
- 150000005303 alkyl halide derivatives Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 208000008524 alveolar soft part sarcoma Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 210000004141 ampulla of vater Anatomy 0.000 description 1
- 210000002255 anal canal Anatomy 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 230000000798 anti-retroviral effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 229940082988 antihypertensives serotonin antagonists Drugs 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- 206010003668 atrial tachycardia Diseases 0.000 description 1
- 239000003693 atypical antipsychotic agent Substances 0.000 description 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 1
- 208000029336 bartholin gland carcinoma Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 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
- 235000013361 beverage Nutrition 0.000 description 1
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000004579 body weight change Effects 0.000 description 1
- 208000016738 bone Paget disease Diseases 0.000 description 1
- 206010006007 bone sarcoma Diseases 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 201000003149 breast fibroadenoma Diseases 0.000 description 1
- 201000003714 breast lobular carcinoma Diseases 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- XAPCMTMQBXLDBB-UHFFFAOYSA-N butanoic acid hexyl ester Natural products CCCCCCOC(=O)CCC XAPCMTMQBXLDBB-UHFFFAOYSA-N 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 208000035269 cancer or benign tumor Diseases 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 210000004903 cardiac system Anatomy 0.000 description 1
- 239000004106 carminic acid Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 201000003340 cellular leiomyoma Diseases 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
- 235000013339 cereals Nutrition 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 208000006990 cholangiocarcinoma Diseases 0.000 description 1
- 201000011011 chorioangioma Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 208000029664 classic familial adenomatous polyposis Diseases 0.000 description 1
- 201000000292 clear cell sarcoma Diseases 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 201000011050 comedo carcinoma Diseases 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 201000008168 congenital mesoblastic nephroma Diseases 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 235000021316 daily nutritional intake Nutrition 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 201000006827 desmoid tumor Diseases 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 229960004597 dexfenfluramine Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 229940075933 dithionate Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 208000028715 ductal breast carcinoma in situ Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- PWVXXGRKLHYWKM-LJQANCHMSA-N eletriptan Chemical compound CN1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1 PWVXXGRKLHYWKM-LJQANCHMSA-N 0.000 description 1
- 229950005627 embonate Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 210000003890 endocrine cell Anatomy 0.000 description 1
- 210000000750 endocrine system Anatomy 0.000 description 1
- 208000001991 endodermal sinus tumor Diseases 0.000 description 1
- 201000003914 endometrial carcinoma Diseases 0.000 description 1
- 208000027858 endometrioid tumor Diseases 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 1
- 235000012734 epicatechin Nutrition 0.000 description 1
- 229940030275 epigallocatechin gallate Drugs 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 201000010877 epithelioid cell melanoma Diseases 0.000 description 1
- FQHMMOGHDWAXDI-WUQHHHCFSA-N ergoloid mesylate Chemical compound CS(O)(=O)=O.C([C@H]1[C@]2(O)O3)CCN1C(=O)[C@H](C)N2C(=O)[C@]3(C(C)C)NC(=O)[C@H]1CN(C)[C@H](CC=2C3=C4C=CC=C3NC=2)[C@@H]4C1 FQHMMOGHDWAXDI-WUQHHHCFSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000003020 exocrine pancreas Anatomy 0.000 description 1
- 210000002603 extrahepatic bile duct Anatomy 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 208000011061 eyelid melanoma Diseases 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 201000010972 female reproductive endometrioid cancer Diseases 0.000 description 1
- 210000004996 female reproductive system Anatomy 0.000 description 1
- 230000003176 fibrotic effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000002224 folic acids Chemical class 0.000 description 1
- 230000003325 follicular Effects 0.000 description 1
- 201000004260 follicular adenoma Diseases 0.000 description 1
- 208000030878 follicular thyroid adenoma Diseases 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 201000003115 germ cell cancer Diseases 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940097042 glucuronate Drugs 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 201000007574 granular cell carcinoma Diseases 0.000 description 1
- 201000006604 granular cell tumor Diseases 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 201000005787 hematologic cancer Diseases 0.000 description 1
- 208000006359 hepatoblastoma Diseases 0.000 description 1
- 201000002735 hepatocellular adenoma Diseases 0.000 description 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
- 102000034345 heterotrimeric G proteins Human genes 0.000 description 1
- 108091006093 heterotrimeric G proteins Proteins 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 description 1
- 201000008298 histiocytosis Diseases 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002476 indolines Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 208000007098 intradermal nevus Diseases 0.000 description 1
- 201000003159 intraductal papilloma Diseases 0.000 description 1
- 229940125425 inverse agonist Drugs 0.000 description 1
- 210000004153 islets of langerhan Anatomy 0.000 description 1
- JSLCOZYBKYHZNL-UHFFFAOYSA-N isobutyric acid butyl ester Natural products CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000014058 juice drink Nutrition 0.000 description 1
- 210000001117 keloid Anatomy 0.000 description 1
- 201000000462 keratinizing squamous cell carcinoma Diseases 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 208000022013 kidney Wilms tumor Diseases 0.000 description 1
- 210000000244 kidney pelvis Anatomy 0.000 description 1
- 201000000062 kidney sarcoma Diseases 0.000 description 1
- 210000004561 lacrimal apparatus Anatomy 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 208000003849 large cell carcinoma Diseases 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 201000004959 laryngeal benign neoplasm Diseases 0.000 description 1
- 206010023841 laryngeal neoplasm Diseases 0.000 description 1
- 102000003835 leukotriene receptors Human genes 0.000 description 1
- 108090000146 leukotriene receptors Proteins 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 208000016992 lung adenocarcinoma in situ Diseases 0.000 description 1
- 201000000966 lung oat cell carcinoma Diseases 0.000 description 1
- 208000037841 lung tumor Diseases 0.000 description 1
- 208000024169 luteoma of pregnancy Diseases 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
- 210000004995 male reproductive system Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 208000021810 malignant mixed neoplasm Diseases 0.000 description 1
- 201000009020 malignant peripheral nerve sheath tumor Diseases 0.000 description 1
- 201000010078 malignant spindle cell melanoma Diseases 0.000 description 1
- 208000027202 mammary Paget disease Diseases 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 208000023356 medullary thyroid gland carcinoma Diseases 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
- 208000023060 memory loss Diseases 0.000 description 1
- 210000002418 meninge Anatomy 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- DILOFCBIBDMHAY-UHFFFAOYSA-N methyl 2-(3,4-dimethoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(OC)C(OC)=C1 DILOFCBIBDMHAY-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 208000024191 minimally invasive lung adenocarcinoma Diseases 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 208000010492 mucinous cystadenocarcinoma Diseases 0.000 description 1
- 208000022669 mucinous neoplasm Diseases 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- AMKVXSZCKVJAGH-UHFFFAOYSA-N naratriptan Chemical compound C12=CC(CCS(=O)(=O)NC)=CC=C2NC=C1C1CCN(C)CC1 AMKVXSZCKVJAGH-UHFFFAOYSA-N 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 208000018305 neoplasm of myocardium Diseases 0.000 description 1
- 201000008026 nephroblastoma Diseases 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 201000004662 neurofibroma of spinal cord Diseases 0.000 description 1
- 208000029974 neurofibrosarcoma Diseases 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 206010029410 night sweats Diseases 0.000 description 1
- 230000036565 night sweats Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229940127073 nucleoside analogue Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- CKNAQFVBEHDJQV-UHFFFAOYSA-N oltipraz Chemical compound S1SC(=S)C(C)=C1C1=CN=CC=N1 CKNAQFVBEHDJQV-UHFFFAOYSA-N 0.000 description 1
- 229950008687 oltipraz Drugs 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 201000006098 orbit sarcoma Diseases 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 208000008798 osteoma Diseases 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 201000005167 ovarian Brenner tumor Diseases 0.000 description 1
- 206010064257 ovarian fibroma Diseases 0.000 description 1
- 208000004971 ovarian teratoma Diseases 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 208000000793 papillary cystadenoma Diseases 0.000 description 1
- 201000010941 papillary squamous carcinoma Diseases 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- CFNJLPHOBMVMNS-UHFFFAOYSA-N pentyl butyrate Chemical compound CCCCCOC(=O)CCC CFNJLPHOBMVMNS-UHFFFAOYSA-N 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 125000001151 peptidyl group Chemical group 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 201000005528 peripheral nervous system neoplasm Diseases 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- WFNDDSQUKATKNX-UHFFFAOYSA-N phenethyl butyrate Chemical compound CCCC(=O)OCCC1=CC=CC=C1 WFNDDSQUKATKNX-UHFFFAOYSA-N 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 201000008814 placenta cancer Diseases 0.000 description 1
- 208000024361 placenta neoplasm Diseases 0.000 description 1
- 208000021249 placental hemangioma Diseases 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 102000030769 platelet activating factor receptor Human genes 0.000 description 1
- 208000004333 pleomorphic adenoma Diseases 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 208000029804 primary prostate urothelial carcinoma Diseases 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 229940127293 prostanoid Drugs 0.000 description 1
- 150000003814 prostanoids Chemical class 0.000 description 1
- 201000005825 prostate adenocarcinoma Diseases 0.000 description 1
- 208000023958 prostate neoplasm Diseases 0.000 description 1
- 201000002025 prostate sarcoma Diseases 0.000 description 1
- 208000013368 pseudoglandular squamous cell carcinoma Diseases 0.000 description 1
- CVSGFMWKZVZOJD-UHFFFAOYSA-N pyrazino[2,3-f]quinoxaline Chemical class C1=CN=C2C3=NC=CN=C3C=CC2=N1 CVSGFMWKZVZOJD-UHFFFAOYSA-N 0.000 description 1
- 229940071139 pyrrolidone carboxylate Drugs 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- ULFRLSNUDGIQQP-UHFFFAOYSA-N rizatriptan Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CN1C=NC=N1 ULFRLSNUDGIQQP-UHFFFAOYSA-N 0.000 description 1
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
- 210000003079 salivary gland Anatomy 0.000 description 1
- 208000014212 sarcomatoid carcinoma Diseases 0.000 description 1
- 230000036186 satiety Effects 0.000 description 1
- 235000019627 satiety Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000036573 scar formation Effects 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 239000003775 serotonin noradrenalin reuptake inhibitor Substances 0.000 description 1
- 208000019694 serous adenocarcinoma Diseases 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- 208000014680 small intestine neoplasm Diseases 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000009561 snack bars Nutrition 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 208000019798 spindle cell melanoma Diseases 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000036262 stenosis Effects 0.000 description 1
- 208000037804 stenosis Diseases 0.000 description 1
- 201000005211 struma ovarii Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000009536 synovial chondromatosis Diseases 0.000 description 1
- 206010042863 synovial sarcoma Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 208000008732 thymoma Diseases 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 1
- 208000013076 thyroid tumor Diseases 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- OHHDIOKRWWOXMT-UHFFFAOYSA-N trazodone hydrochloride Chemical compound [H+].[Cl-].ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 OHHDIOKRWWOXMT-UHFFFAOYSA-N 0.000 description 1
- 229960002301 trazodone hydrochloride Drugs 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- ZNRGQMMCGHDTEI-ITGUQSILSA-N tropisetron Chemical compound C1=CC=C2C(C(=O)O[C@H]3C[C@H]4CC[C@@H](C3)N4C)=CNC2=C1 ZNRGQMMCGHDTEI-ITGUQSILSA-N 0.000 description 1
- 208000022158 tubulovillous adenoma Diseases 0.000 description 1
- 208000017997 tumor of parathyroid gland Diseases 0.000 description 1
- 208000025444 tumor of salivary gland Diseases 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001745 uvea Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 201000011531 vascular cancer Diseases 0.000 description 1
- 206010055031 vascular neoplasm Diseases 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 208000009540 villous adenoma Diseases 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
- 208000028010 vulval Paget disease Diseases 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- ULSDMUVEXKOYBU-ZDUSSCGKSA-N zolmitriptan Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1C[C@H]1COC(=O)N1 ULSDMUVEXKOYBU-ZDUSSCGKSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- 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
-
- 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
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Reproductive Health (AREA)
- Physical Education & Sports Medicine (AREA)
- Emergency Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Rheumatology (AREA)
- Virology (AREA)
- AIDS & HIV (AREA)
- Cardiology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Pregnancy & Childbirth (AREA)
- Psychiatry (AREA)
- Oncology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361793407P | 2013-03-15 | 2013-03-15 | |
| US61/793,407 | 2013-03-15 | ||
| PCT/US2014/028413 WO2014144130A2 (en) | 2013-03-15 | 2014-03-14 | Pharmaceutical composition comprising an ampk activator and a serotonergic agent and methods of use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2909633A1 true CA2909633A1 (en) | 2014-09-18 |
Family
ID=51538303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2909633A Abandoned CA2909633A1 (en) | 2013-03-15 | 2014-03-14 | Pharmaceutical composition comprising an ampk activator and a serotonergic agent and methods of use thereof |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20140350064A1 (enExample) |
| EP (1) | EP2983473A4 (enExample) |
| JP (1) | JP2016513734A (enExample) |
| KR (1) | KR20160005341A (enExample) |
| CN (1) | CN105636438A (enExample) |
| AR (1) | AR095631A1 (enExample) |
| AU (1) | AU2014227807B2 (enExample) |
| BR (1) | BR112015023922A2 (enExample) |
| CA (1) | CA2909633A1 (enExample) |
| CL (1) | CL2015002680A1 (enExample) |
| HK (1) | HK1222297A1 (enExample) |
| IL (1) | IL241587B (enExample) |
| MX (1) | MX2015012760A (enExample) |
| RU (1) | RU2015143438A (enExample) |
| TW (1) | TW201444552A (enExample) |
| WO (1) | WO2014144130A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11103465B2 (en) | 2017-11-22 | 2021-08-31 | Ted's Brain Science, Inc. | Trans-resveratrol topical medication for the treatment of pain and method of manufacture thereof |
| US11724985B2 (en) | 2020-05-19 | 2023-08-15 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180071269A1 (en) * | 2015-08-12 | 2018-03-15 | Tianxin Wang | Therapeutical methods, formulations and nutraceutical formulations |
| ES2567105B1 (es) * | 2014-09-19 | 2017-02-10 | Consejo Superior De Investigaciones Científicas (Csic) | Derivados de indol para la prevención y/o tratamiento de diabetes ytrastornos metabólicos relacionados |
| WO2016126662A1 (en) * | 2015-02-03 | 2016-08-11 | Kardiatonos, Inc. | Compounds for the prevention and treatment of vascular disease |
| US10463649B2 (en) | 2015-06-08 | 2019-11-05 | Texas Tech University System | Inhibitors of Mc1-1 as drugs to overcome resistance to BRAF inhibitors and MEK inhibitors |
| WO2017018752A1 (ko) * | 2015-07-29 | 2017-02-02 | 고려대학교 산학협력단 | 부스피론 유도체 및 이를 함유하는 약학 조성물 |
| KR101663543B1 (ko) * | 2015-07-29 | 2016-10-07 | 고려대학교 산학협력단 | 부스피론 유도체 및 이를 함유하는 약학 조성물 |
| US10357466B2 (en) * | 2015-08-01 | 2019-07-23 | Stephen J. Petti | Compositions and methods for combination pharmacological treatments to induce a prolonged, mild decrease in core body temperature |
| CN105541665A (zh) * | 2016-02-18 | 2016-05-04 | 江苏大学 | 一种抗肿瘤药物化合物及制备方法和应用 |
| KR101838622B1 (ko) * | 2016-09-20 | 2018-03-14 | 김브라이언 | 아디포넥틴 수용체에 대한 작용제 펩타이드 |
| US11040935B2 (en) | 2016-10-05 | 2021-06-22 | University of Pittsburgh—of the Commonwealth System of Higher Education | Small molecule AMPK activators |
| EP3338768B1 (en) | 2016-12-20 | 2019-10-30 | LTS Lohmann Therapie-Systeme AG | Transdermal therapeutic system containing asenapine |
| KR102614709B1 (ko) | 2016-12-20 | 2023-12-18 | 에르테에스 로만 테라피-시스테메 아게 | 아세나핀 및 폴리실록산 또는 폴리이소부틸렌을 함유하는 경피흡수 치료 시스템 |
| US11033512B2 (en) | 2017-06-26 | 2021-06-15 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine and silicone acrylic hybrid polymer |
| CN107252425A (zh) * | 2017-07-12 | 2017-10-17 | 上海华堇生物技术有限责任公司 | 去氢延胡索素的药物用途 |
| US11723894B2 (en) * | 2017-10-26 | 2023-08-15 | Terran Biosciences, Inc. | Combination product for the treatment of neurological and/or psychiatric disorders |
| US11208475B1 (en) * | 2018-01-30 | 2021-12-28 | Flagship Pioneering Innovations V, Inc. | Methods and compositions for treating inflammatory or autoimmune diseases or conditions using serotonin receptor activators |
| CN108159044A (zh) * | 2018-02-26 | 2018-06-15 | 华中科技大学 | 抗坏血酸与二甲双胍的复合制剂用于制备化疗药物的应用 |
| US12329862B2 (en) | 2018-06-20 | 2025-06-17 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
| AU2019291060B2 (en) | 2018-06-20 | 2024-09-05 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
| CN108997172B (zh) * | 2018-08-08 | 2020-12-15 | 中国人民解放军总医院 | 抗肿瘤化合物 |
| WO2020087031A1 (en) | 2018-10-26 | 2020-04-30 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| CN109771424B (zh) * | 2019-03-11 | 2021-03-16 | 马慧 | 一种防治老年ⅱ型糖尿病性骨质疏松症的药物组合物及其应用 |
| CN109793727A (zh) * | 2019-03-13 | 2019-05-24 | 湖北科技学院 | 一种有效抗恶性肿瘤的药物组合物及其应用 |
| WO2021050538A1 (en) | 2019-09-10 | 2021-03-18 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Methods and materials for increasing level of phosphorylated ampk protein |
| CN110559298A (zh) * | 2019-10-28 | 2019-12-13 | 中国药科大学 | 一种天然化合物Egenine用于制备抗肾纤维化药物的用途 |
| WO2021086133A1 (ko) * | 2019-10-31 | 2021-05-06 | (주)제이디바이오사이언스 | 삼환식 화합물 및 이의 약학적 용도 |
| WO2022017440A1 (zh) * | 2020-07-22 | 2022-01-27 | 山东绿叶制药有限公司 | 5-ht 2a受体抑制剂或反向激动剂及其制备方法和应用 |
| US20240208923A1 (en) * | 2021-03-10 | 2024-06-27 | Jnana Therapeutics Inc. | Small molecule inhibitors of mammalian slc6a19 function |
| WO2023283364A2 (en) | 2021-07-07 | 2023-01-12 | Terran Biosciences Inc. | N,n-dimethyltryptamine and related psychedlics and uses thereof |
| CA3237988A1 (en) | 2021-11-12 | 2023-05-19 | Terran Biosciences Inc. | Psilocybin and o-acetylpsilocin, salts and solid state forms thereof |
| WO2024123825A1 (en) * | 2022-12-05 | 2024-06-13 | Enveda Therapeutics, Inc. | Nootkatone for the treatment of psoriasis or atopic dermatitis |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3174901A (en) * | 1963-01-31 | 1965-03-23 | Jan Marcel Didier Aron Samuel | Process for the oral treatment of diabetes |
| EP1762234A4 (en) * | 2004-06-28 | 2010-05-05 | Kao Corp | AMPK AKTIVATOR |
| US20070149466A1 (en) * | 2005-07-07 | 2007-06-28 | Michael Milburn | Methods and related compositions for treating or preventing obesity, insulin resistance disorders, and mitochondrial-associated disorders |
| US7754700B2 (en) * | 2006-04-24 | 2010-07-13 | Trager Seymour F | Composition and methods for alleviating symptoms of neurotoxicity |
| US20120183600A1 (en) * | 2007-01-16 | 2012-07-19 | Chien-Hung Chen | Novel composition for treating metabolic syndrome and other conditions |
| TWI629058B (zh) * | 2007-01-16 | 2018-07-11 | 陳建宏 | 醫藥組成物及其用途 |
| US20120232003A1 (en) * | 2009-03-13 | 2012-09-13 | Takahashi Joseph S | Compositions and methods for diabetes treatment |
| US8486922B2 (en) * | 2010-04-28 | 2013-07-16 | Chien-Hung Chen | Composition |
-
2014
- 2014-03-14 TW TW103109748A patent/TW201444552A/zh unknown
- 2014-03-14 US US14/212,734 patent/US20140350064A1/en not_active Abandoned
- 2014-03-14 EP EP14763798.7A patent/EP2983473A4/en not_active Withdrawn
- 2014-03-14 HK HK16109576.5A patent/HK1222297A1/zh unknown
- 2014-03-14 JP JP2016502780A patent/JP2016513734A/ja active Pending
- 2014-03-14 MX MX2015012760A patent/MX2015012760A/es unknown
- 2014-03-14 BR BR112015023922A patent/BR112015023922A2/pt not_active IP Right Cessation
- 2014-03-14 RU RU2015143438A patent/RU2015143438A/ru unknown
- 2014-03-14 CA CA2909633A patent/CA2909633A1/en not_active Abandoned
- 2014-03-14 WO PCT/US2014/028413 patent/WO2014144130A2/en not_active Ceased
- 2014-03-14 AU AU2014227807A patent/AU2014227807B2/en not_active Ceased
- 2014-03-14 CN CN201480028057.0A patent/CN105636438A/zh active Pending
- 2014-03-14 KR KR1020157029838A patent/KR20160005341A/ko not_active Withdrawn
- 2014-03-17 AR ARP140101258A patent/AR095631A1/es unknown
-
2015
- 2015-09-14 CL CL2015002680A patent/CL2015002680A1/es unknown
- 2015-09-16 IL IL241587A patent/IL241587B/en not_active IP Right Cessation
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11103465B2 (en) | 2017-11-22 | 2021-08-31 | Ted's Brain Science, Inc. | Trans-resveratrol topical medication for the treatment of pain and method of manufacture thereof |
| US11724985B2 (en) | 2020-05-19 | 2023-08-15 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| US11746088B2 (en) | 2020-05-19 | 2023-09-05 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| US11834410B2 (en) | 2020-05-19 | 2023-12-05 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| US11958807B2 (en) | 2020-05-19 | 2024-04-16 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| US12110272B2 (en) | 2020-05-19 | 2024-10-08 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| US12240813B2 (en) | 2020-05-19 | 2025-03-04 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| US12291499B2 (en) | 2020-05-19 | 2025-05-06 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
Also Published As
| Publication number | Publication date |
|---|---|
| HK1222297A1 (zh) | 2017-06-30 |
| JP2016513734A (ja) | 2016-05-16 |
| IL241587B (en) | 2019-01-31 |
| TW201444552A (zh) | 2014-12-01 |
| WO2014144130A3 (en) | 2015-02-05 |
| EP2983473A2 (en) | 2016-02-17 |
| CN105636438A (zh) | 2016-06-01 |
| AU2014227807A1 (en) | 2015-11-05 |
| WO2014144130A2 (en) | 2014-09-18 |
| AR095631A1 (es) | 2015-10-28 |
| CL2015002680A1 (es) | 2016-09-02 |
| KR20160005341A (ko) | 2016-01-14 |
| AU2014227807B2 (en) | 2018-03-08 |
| RU2015143438A (ru) | 2017-04-21 |
| US20140350064A1 (en) | 2014-11-27 |
| EP2983473A4 (en) | 2016-11-23 |
| MX2015012760A (es) | 2016-06-17 |
| BR112015023922A2 (pt) | 2017-07-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2014227807B2 (en) | Pharmaceutical composition comprising an AMPK activator and a serotonergic agent and methods of use thereof | |
| US20120183600A1 (en) | Novel composition for treating metabolic syndrome and other conditions | |
| AU2007234382B2 (en) | Combinations comprising BCR-ABL/C-KIT/PDGF-R TK inhibitors for treating cancer | |
| TWI556820B (zh) | Ｈｓｐ９０抑制劑之組合 | |
| JP2669507B2 (ja) | 大脳卒中の治療のための薬剤 | |
| CN105579044A (zh) | 双脱水半乳糖醇及其类似物与衍生物用于治疗复发性恶性神经胶瘤或进行性继发脑瘤的用途 | |
| SK13952002A3 (sk) | Farmaceutická kompozícia na liečenie akútnej, chronickej a/alebo neuropatickej bolesti a migrén | |
| KR20160037245A (ko) | 과증식성 질환을 치료하기 위한 신규 조성물 및 방법 | |
| CA2369789A1 (en) | Combination treatment for depression | |
| JP2017119702A (ja) | ギラン・バレー症候群に伴う神経因性疼痛の予防又は治療剤 | |
| US20160175293A1 (en) | Pim kinase inhibitor combinations | |
| AU2010235917A1 (en) | Combination of organic compounds | |
| JP2008525509A (ja) | 片頭痛治療のための、他の片頭痛治療薬と組合せた選択されたｃｇｒｐアンタゴニストの使用 | |
| US20050176725A1 (en) | Combination of glivec (sti571) with a cyclin-dependent kinase inhibitor, especially flavopiridol, in the treatment of cancer | |
| JP2024523485A (ja) | 少なくとも１種類のセロトニン再取り込み阻害剤及び少なくとも１種の塩化カリウム共輸送体２型の刺激剤を含む組み合せ、並びにその医学的使用 | |
| CN114144179A (zh) | 含血清素的试剂和5-ht1a受体拮抗剂 | |
| WO2025181153A1 (en) | Use of atr inhibitors in combination with pi3k alpha inhibitors | |
| JP2025538876A (ja) | がん治療のためのｌｓｄ１阻害薬とメニン阻害薬の組合せ | |
| CN101198253A (zh) | 治疗癌症的组合、方法和组合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20190307 |
|
| FZDE | Discontinued |
Effective date: 20220301 |