TW201444552A - 一種包含ａｍｐｋ激活劑及血清素活性製劑之醫藥組合物及其用途 - Google Patents

Info

Publication number

TW201444552A

TW201444552A TW103109748A TW103109748A TW201444552A TW 201444552 A TW201444552 A TW 201444552A TW 103109748 A TW103109748 A TW 103109748A TW 103109748 A TW103109748 A TW 103109748A TW 201444552 A TW201444552 A TW 201444552A

Authority

TW

Taiwan

Prior art keywords

piperidin

fluorobenzyl

acetamide

ethyl

methyl

Prior art date

2013-03-15

Links

• Espacenet
• Global Dossier
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• 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 15
• 238000000034 method Methods 0.000 title abstract description 19
• 239000003795 chemical substances by application Substances 0.000 title abstract description 6
• 230000000862 serotonergic effect Effects 0.000 title 1
• 239000000203 mixture Substances 0.000 claims abstract description 145
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 103
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 98
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 78
• 201000010099 disease Diseases 0.000 claims abstract description 70
• 201000011510 cancer Diseases 0.000 claims abstract description 62
• 229940076279 serotonin Drugs 0.000 claims abstract description 35
• DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 claims abstract description 32
• 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 31
• 229960003987 melatonin Drugs 0.000 claims abstract description 31
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin hydrochloride Natural products CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims abstract description 30
• 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 20
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 20
• 239000003814 drug Substances 0.000 claims abstract description 20
• 229940079593 drug Drugs 0.000 claims abstract description 17
• 238000011282 treatment Methods 0.000 claims abstract description 15
• 230000000694 effects Effects 0.000 claims abstract description 8
• 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
• VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 claims description 265
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 247
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 224
• -1 corlumidin Chemical class 0.000 claims description 200
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 143
• 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 91
• 229940095064 tartrate Drugs 0.000 claims description 88
• 238000009472 formulation Methods 0.000 claims description 85
• 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 49
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 46
• 150000001413 amino acids Chemical group 0.000 claims description 44
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 37
• 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 36
• 150000003839 salts Chemical class 0.000 claims description 36
• 150000001875 compounds Chemical class 0.000 claims description 34
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• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
• 108010076365 Adiponectin Proteins 0.000 claims description 26
• 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
• 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 24
• 239000003310 5-hydroxyindoleacetic acid Substances 0.000 claims description 24
• 229960003105 metformin Drugs 0.000 claims description 22
• 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 21
• 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 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
• NWAJASRWXZETDW-UHFFFAOYSA-N acetamide;oxalic acid Chemical compound CC(N)=O.OC(=O)C(O)=O NWAJASRWXZETDW-UHFFFAOYSA-N 0.000 claims description 18
• 239000012876 carrier material Substances 0.000 claims description 18
• 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 18
• 229910052757 nitrogen Inorganic materials 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
• 229960004425 sibutramine Drugs 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 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
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• 208000030507 AIDS Diseases 0.000 claims description 14
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 14
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
• 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 description 13
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 13
• 239000003112 inhibitor Substances 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
• 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 12
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 12
• 239000005557 antagonist Substances 0.000 claims description 12
• 229960004606 clomipramine Drugs 0.000 claims description 12
• YBSLUBPQYDULIZ-UHFFFAOYSA-N oxalic acid;urea Chemical compound NC(N)=O.OC(=O)C(O)=O YBSLUBPQYDULIZ-UHFFFAOYSA-N 0.000 claims description 12
• 239000002243 precursor Substances 0.000 claims description 12
• WIGJKQWSXRGQBN-UHFFFAOYSA-N 1h-anthracen-2-one Chemical compound C1=CC=C2C=C(C=CC(=O)C3)C3=CC2=C1 WIGJKQWSXRGQBN-UHFFFAOYSA-N 0.000 claims description 11
• 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 11
• 108010009736 Protein Hydrolysates Proteins 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 239000000039 congener Substances 0.000 claims description 11
• 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 11
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• 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 10
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• 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
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