TWI411611B - Ｇｐｒ１１９調節劑 - Google Patents

Info

Publication number

TWI411611B

TWI411611B TW099117782A TW99117782A TWI411611B TW I411611 B TWI411611 B TW I411611B TW 099117782 A TW099117782 A TW 099117782A TW 99117782 A TW99117782 A TW 99117782A TW I411611 B TWI411611 B TW I411611B

Authority

TW

Taiwan

Prior art keywords

methyl

cyano

piperidine

pyrazol

carboxylic acid

Prior art date

2009-06-05

Links

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• Global Dossier
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• 101150046911 Gpr119 gene Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 222
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
• 201000010099 disease Diseases 0.000 claims abstract description 25
• 101000996752 Homo sapiens Glucose-dependent insulinotropic receptor Proteins 0.000 claims abstract description 22
• 102100033839 Glucose-dependent insulinotropic receptor Human genes 0.000 claims abstract description 20
• 230000000694 effects Effects 0.000 claims abstract description 20
• 238000011282 treatment Methods 0.000 claims abstract description 17
• 239000000203 mixture Substances 0.000 claims description 151
• -1 3-hydroxycyclobutyl Chemical group 0.000 claims description 133
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 55
• 229910052739 hydrogen Inorganic materials 0.000 claims description 53
• 239000001257 hydrogen Substances 0.000 claims description 52
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 37
• 239000000284 extract Substances 0.000 claims description 31
• 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 claims description 29
• 206010012601 diabetes mellitus Diseases 0.000 claims description 29
• 239000008103 glucose Substances 0.000 claims description 29
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 210000004369 blood Anatomy 0.000 claims description 23
• 239000008280 blood Substances 0.000 claims description 23
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 239000003795 chemical substances by application Substances 0.000 claims description 17
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
• 238000004519 manufacturing process Methods 0.000 claims description 14
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 13
• 150000001721 carbon Chemical group 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 239000011737 fluorine Substances 0.000 claims description 13
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
• 239000003472 antidiabetic agent Substances 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 239000001301 oxygen Substances 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 229940125708 antidiabetic agent Drugs 0.000 claims description 11
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 10
• 206010022489 Insulin Resistance Diseases 0.000 claims description 10
• 208000008589 Obesity Diseases 0.000 claims description 10
• 239000000883 anti-obesity agent Substances 0.000 claims description 10
• 229940125710 antiobesity agent Drugs 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 235000020824 obesity Nutrition 0.000 claims description 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
• 208000029078 coronary artery disease Diseases 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
• 230000002792 vascular Effects 0.000 claims description 9
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 8
• 102000016267 Leptin Human genes 0.000 claims description 8
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• 230000002159 abnormal effect Effects 0.000 claims description 8
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• 206010009900 Colitis ulcerative Diseases 0.000 claims description 7
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 7
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
• 208000035475 disorder Diseases 0.000 claims description 7
• 229960004580 glibenclamide Drugs 0.000 claims description 7
• ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 claims description 7
• 201000001421 hyperglycemia Diseases 0.000 claims description 7
• 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 7
• 229940039781 leptin Drugs 0.000 claims description 7
• 208000010125 myocardial infarction Diseases 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• GVIYUKXRXPXMQM-BPXGDYAESA-N 221231-10-3 Chemical compound C([C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]1C(N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CSSC1)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C(C)C)=O)C1=CC=C(O)C=C1 GVIYUKXRXPXMQM-BPXGDYAESA-N 0.000 claims description 6
• RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 208000006011 Stroke Diseases 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 230000002503 metabolic effect Effects 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 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 6
• MFFMDFFZMYYVKS-SECBINFHSA-N sitagliptin Chemical compound C([C@H](CC(=O)N1CC=2N(C(=NN=2)C(F)(F)F)CC1)N)C1=CC(F)=C(F)C=C1F MFFMDFFZMYYVKS-SECBINFHSA-N 0.000 claims description 6
• 229960004034 sitagliptin Drugs 0.000 claims description 6
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 5
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 5
• 229960003105 metformin Drugs 0.000 claims description 5
• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 5
• 229960001243 orlistat Drugs 0.000 claims description 5
• 230000000291 postprandial effect Effects 0.000 claims description 5
• 108010029667 pramlintide Proteins 0.000 claims description 5
• NRKVKVQDUCJPIZ-MKAGXXMWSA-N pramlintide acetate Chemical compound C([C@@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@@H](N)CCCCN)[C@@H](C)O)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 NRKVKVQDUCJPIZ-MKAGXXMWSA-N 0.000 claims description 5
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
• BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 claims description 4
• 208000010444 Acidosis Diseases 0.000 claims description 4
• 206010002383 Angina Pectoris Diseases 0.000 claims description 4
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• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 4
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
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• 208000003790 Foot Ulcer Diseases 0.000 claims description 4
• 206010019280 Heart failures Diseases 0.000 claims description 4
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 4
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• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 206010022562 Intermittent claudication Diseases 0.000 claims description 4
• 208000007976 Ketosis Diseases 0.000 claims description 4
• 208000007177 Left Ventricular Hypertrophy Diseases 0.000 claims description 4
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
• 206010028851 Necrosis Diseases 0.000 claims description 4
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• 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 4
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 4
• 208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 206010036618 Premenstrual syndrome Diseases 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 208000007536 Thrombosis Diseases 0.000 claims description 4
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
• ZSBOMTDTBDDKMP-OAHLLOKOSA-N alogliptin Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 ZSBOMTDTBDDKMP-OAHLLOKOSA-N 0.000 claims description 4
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• OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 claims description 4
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• TUOSYWCFRFNJBS-BHVANESWSA-N dirlotapide Chemical compound O=C([C@@H](NC(=O)C=1N(C2=CC=C(NC(=O)C=3C(=CC=CC=3)C=3C=CC(=CC=3)C(F)(F)F)C=C2C=1)C)C=1C=CC=CC=1)N(C)CC1=CC=CC=C1 TUOSYWCFRFNJBS-BHVANESWSA-N 0.000 claims description 4
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• ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 claims description 4
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• WAIMQYARIQWEBV-UHFFFAOYSA-N propan-2-yl 4-[5-cyano-4-[[2-fluoro-4-(2-methyltetrazol-5-yl)phenoxy]methyl]pyrazol-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1N1C(C#N)=C(COC=2C(=CC(=CC=2)C2=NN(C)N=N2)F)C=N1 WAIMQYARIQWEBV-UHFFFAOYSA-N 0.000 claims description 4
• 229960004937 saxagliptin Drugs 0.000 claims description 4
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• 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 4
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• VCVWXKKWDOJNIT-ZOMKSWQUSA-N tesofensine Chemical compound C1([C@H]2C[C@@H]3CC[C@@H](N3C)[C@@H]2COCC)=CC=C(Cl)C(Cl)=C1 VCVWXKKWDOJNIT-ZOMKSWQUSA-N 0.000 claims description 4
• 201000010875 transient cerebral ischemia Diseases 0.000 claims description 4
• SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 claims description 4
• 229960001254 vildagliptin Drugs 0.000 claims description 4
• GDKHTWWUBKWACU-UHFFFAOYSA-N (1-methylcyclopropyl) 4-[5-cyano-4-[[4-(1-methyltetrazol-5-yl)phenoxy]methyl]pyrazol-1-yl]piperidine-1-carboxylate Chemical compound CN1N=NN=C1C(C=C1)=CC=C1OCC1=C(C#N)N(C2CCN(CC2)C(=O)OC2(C)CC2)N=C1 GDKHTWWUBKWACU-UHFFFAOYSA-N 0.000 claims description 3
• XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims description 3
• FOZFSEMFCIPOSZ-SPCKQMHLSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-[[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]piperidine-3,4,5-triol;trihydrate Chemical compound O.O.O.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 FOZFSEMFCIPOSZ-SPCKQMHLSA-N 0.000 claims description 3
• PUTJFIQGLGDLIT-RNDOZLNUSA-N (2s,3s,3ar,5as,9as,9br)-3-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-3,4,5,5a,7,8,9,9b-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde Chemical compound C=1([C@@H](O)C[C@H]2[C@@]3(C)[C@@H]([C@]4(CCCC(C)(C)[C@@H]4CC3)C)C[C@]2(C)C=O)C=COC=1 PUTJFIQGLGDLIT-RNDOZLNUSA-N 0.000 claims description 3
• QJLPWVUZFKETMK-LLVKDONJSA-N (5r)-1,5,7,9,11,14-hexahydroxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carboxylic acid Chemical compound O=C1C2=C(O)C=C(O)C=C2C(=O)C2=C1C(O)=C1C[C@@H](O)C(C=C(C(=C3O)C(O)=O)C)=C3C1=C2O QJLPWVUZFKETMK-LLVKDONJSA-N 0.000 claims description 3
• LLJFMFZYVVLQKT-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-2-isoquinolinyl)ethyl]phenyl]sulfonylurea Chemical compound C=1C(OC)=CC=C(C(C2=O)(C)C)C=1C(=O)N2CCC(C=C1)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 LLJFMFZYVVLQKT-UHFFFAOYSA-N 0.000 claims description 3
• HQSRVYUCBOCBLY-XOOFNSLWSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2s,4r)-2-(4-chlorophenyl)-2-[(4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@H]3O[C@@](CSC=4N(C=NN=4)C)(OC3)C=3C=CC(Cl)=CC=3)=CC=2)C=C1 HQSRVYUCBOCBLY-XOOFNSLWSA-N 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• MVDXXGIBARMXSA-PYUWXLGESA-N 5-[[(2r)-2-benzyl-3,4-dihydro-2h-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(O[C@@H](CC=2C=CC=CC=2)CC2)C2=C1 MVDXXGIBARMXSA-PYUWXLGESA-N 0.000 claims description 3
• 108010070305 AOD 9604 Proteins 0.000 claims description 3
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