RU2015143438A - Фармацевтическая композиция, содержащая активатор амрк и серотонинергическое средство, и способы ее применения - Google Patents

Info

Publication number

RU2015143438A

RU2015143438A RU2015143438A RU2015143438A RU2015143438A RU 2015143438 A RU2015143438 A RU 2015143438A RU 2015143438 A RU2015143438 A RU 2015143438A RU 2015143438 A RU2015143438 A RU 2015143438A RU 2015143438 A RU2015143438 A RU 2015143438A

Authority

RU

Russia

Prior art keywords

acetamide

piperidin

fluorobenzyl

ethyl

methyl

Prior art date

2013-03-15

Links

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• Global Dossier
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• 239000003795 chemical substances by application Substances 0.000 title claims 32
• 239000008194 pharmaceutical composition Substances 0.000 title claims 21
• 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 9
• -1 corypalmin Chemical compound 0.000 claims 308
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 191
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 144
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 99
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 82
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 58
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 57
• 229940095064 tartrate Drugs 0.000 claims 39
• 235000013877 carbamide Nutrition 0.000 claims 33
• 239000004202 carbamide Substances 0.000 claims 33
• 238000000034 method Methods 0.000 claims 25
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 25
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 20
• DUUGKQCEGZLZNO-UHFFFAOYSA-N 5-hydroxyindoleacetic acid Chemical compound C1=C(O)C=C2C(CC(=O)O)=CNC2=C1 DUUGKQCEGZLZNO-UHFFFAOYSA-N 0.000 claims 19
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 19
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 18
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 18
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 17
• 150000003839 salts Chemical class 0.000 claims 16
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 14
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 12
• 108010076365 Adiponectin Proteins 0.000 claims 12
• 150000001875 compounds Chemical class 0.000 claims 12
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims 12
• 239000000203 mixture Substances 0.000 claims 12
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 10
• 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 10
• 102000011690 Adiponectin Human genes 0.000 claims 10
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 10
• 201000010099 disease Diseases 0.000 claims 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
• 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 8
• 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims 8
• RVWZUOPFHTYIEO-UHFFFAOYSA-N 5-hydroxyindoleacetic acid Natural products C1=C(O)C=C2C(C(=O)O)=CNC2=C1 RVWZUOPFHTYIEO-UHFFFAOYSA-N 0.000 claims 8
• 239000003310 5-hydroxyindoleacetic acid Substances 0.000 claims 8
• 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 8
• XJLDYKIEURAVBW-UHFFFAOYSA-N Aethyl-heptyl-keton Natural products CCCCCCCC(=O)CC XJLDYKIEURAVBW-UHFFFAOYSA-N 0.000 claims 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 8
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 8
• YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 claims 8
• 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 8
• DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 claims 8
• 229960003987 melatonin Drugs 0.000 claims 8
• 229960003105 metformin Drugs 0.000 claims 8
• LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 claims 8
• 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 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 7
• 229940076279 serotonin Drugs 0.000 claims 7
• KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 claims 6
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 6
• 229940000681 5-hydroxytryptophan Drugs 0.000 claims 6
• 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 6
• GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 claims 6
• 229940123464 Thiazolidinedione Drugs 0.000 claims 6
• 239000005557 antagonist Substances 0.000 claims 6
• 229960004606 clomipramine Drugs 0.000 claims 6
• 230000007062 hydrolysis Effects 0.000 claims 6
• 238000006460 hydrolysis reaction Methods 0.000 claims 6
• 239000003112 inhibitor Substances 0.000 claims 6
• 239000002207 metabolite Substances 0.000 claims 6
• 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 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
• 239000002243 precursor Substances 0.000 claims 6
• 239000000651 prodrug Substances 0.000 claims 6
• 229940002612 prodrug Drugs 0.000 claims 6
• 239000000047 product Substances 0.000 claims 6
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 5
• QAYQVTMHUMLSNG-MHZLTWQESA-N 5-benzyl-2-ethyl-3-[(1s)-5-[2-(2h-tetrazol-5-yl)phenyl]-2,3-dihydro-1h-inden-1-yl]imidazo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H]3C4=CC=C(C=C4CC3)C=3C(=CC=CC=3)C=3NN=NN=3)C(CC)=NC=2C=CN1CC1=CC=CC=C1 QAYQVTMHUMLSNG-MHZLTWQESA-N 0.000 claims 5
• 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 5
• 239000010802 sludge Substances 0.000 claims 5
• 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 4
• 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 4
• DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 claims 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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
• 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 4
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• 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 4
• SZWGKKCURSNZTM-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(4-methylphenyl)propanamide Chemical compound C1=CC(OC)=CC=C1C(C)C(=O)NC1=CC=C(C)C=C1 SZWGKKCURSNZTM-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 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
• 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 4
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• 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 4
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• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
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• 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 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
• 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
• 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 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
• 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 2
• 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 2
• GDYQNDBRKIAHSX-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[(4-methylphenyl)methyl]-n-[1-(2-morpholin-4-ylethyl)piperidin-4-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.C1=CC(OC)=CC=C1CC(=O)N(C1CCN(CCN2CCOCC2)CC1)CC1=CC=C(C)C=C1 GDYQNDBRKIAHSX-UHFFFAOYSA-N 0.000 claims 2
• 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 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
• 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
• 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 2
• UBULIBNSZMFGMU-XHBSWPGZSA-N 2-[(5as,6ar,9r)-7-methyl-5,5a,6,6a,8,9-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]acetonitrile Chemical compound C1NC2=CC=CC3=C2[C@@H]1C[C@@H]1C3=C[C@@H](CC#N)CN1C UBULIBNSZMFGMU-XHBSWPGZSA-N 0.000 claims 2
• 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 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
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
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• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 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
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• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
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• 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 2
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• 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
• 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 2
• NUAJBITWGGTZCM-UHFFFAOYSA-N 3-[2-[(2-methoxyphenyl)methylamino]ethyl]-1h-quinazoline-2,4-dione Chemical compound COC1=CC=CC=C1CNCCN1C(=O)C2=CC=CC=C2NC1=O NUAJBITWGGTZCM-UHFFFAOYSA-N 0.000 claims 2
• 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 2
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• 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 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
• 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 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
• 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 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
• 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
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