ZA200207444B - Malonamic acids and derivatives thereof as thyroid receptor ligands. - Google Patents
Malonamic acids and derivatives thereof as thyroid receptor ligands. Download PDFInfo
- Publication number
- ZA200207444B ZA200207444B ZA200207444A ZA200207444A ZA200207444B ZA 200207444 B ZA200207444 B ZA 200207444B ZA 200207444 A ZA200207444 A ZA 200207444A ZA 200207444 A ZA200207444 A ZA 200207444A ZA 200207444 B ZA200207444 B ZA 200207444B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydrogen
- compound
- phenyl
- hydroxy
- phenoxy
- Prior art date
Links
- 239000003446 ligand Substances 0.000 title description 10
- 102000004217 thyroid hormone receptors Human genes 0.000 title description 10
- 108090000721 thyroid hormone receptors Proteins 0.000 title description 10
- CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical class NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 180
- 239000001257 hydrogen Substances 0.000 claims description 180
- 150000001875 compounds Chemical class 0.000 claims description 162
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 152
- 125000000217 alkyl group Chemical group 0.000 claims description 126
- 125000001424 substituent group Chemical group 0.000 claims description 102
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 56
- 150000002367 halogens Chemical class 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 56
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 125000004043 oxo group Chemical group O=* 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 229940002612 prodrug Drugs 0.000 claims description 24
- 239000000651 prodrug Substances 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 208000008589 Obesity Diseases 0.000 claims description 18
- 235000020824 obesity Nutrition 0.000 claims description 18
- 201000004384 Alopecia Diseases 0.000 claims description 16
- 206010020772 Hypertension Diseases 0.000 claims description 16
- 230000003676 hair loss Effects 0.000 claims description 16
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 15
- 125000002837 carbocyclic group Chemical group 0.000 claims description 14
- 208000024963 hair loss Diseases 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 201000001320 Atherosclerosis Diseases 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
- -1 (i) -CN Chemical class 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 208000029078 coronary artery disease Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 3
- 208000001132 Osteoporosis Diseases 0.000 claims description 3
- 206010033307 Overweight Diseases 0.000 claims description 3
- 208000024799 Thyroid disease Diseases 0.000 claims description 3
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 206010003119 arrhythmia Diseases 0.000 claims description 3
- 208000003532 hypothyroidism Diseases 0.000 claims description 3
- 230000002989 hypothyroidism Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 201000002510 thyroid cancer Diseases 0.000 claims description 3
- 208000021510 thyroid gland disease Diseases 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 2
- XFEIKBVZEBTAMJ-UHFFFAOYSA-N 3-[3,5-dichloro-4-[3-(cyclopropylmethylsulfonyl)-4-hydroxyphenoxy]anilino]-3-oxopropanoic acid Chemical compound ClC1=CC(NC(=O)CC(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CC2)=C1 XFEIKBVZEBTAMJ-UHFFFAOYSA-N 0.000 claims 2
- FQSWYWURERJGPV-UHFFFAOYSA-N 3-[3,5-dichloro-4-[3-(cyclopropylsulfamoyl)-4-hydroxyphenoxy]anilino]-3-oxopropanoic acid Chemical compound ClC1=CC(NC(=O)CC(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)NC2CC2)=C1 FQSWYWURERJGPV-UHFFFAOYSA-N 0.000 claims 2
- WWSBRQBNMHIVPT-UHFFFAOYSA-N 3-[4-[3-(2-cyclopentylacetyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(C(=O)CC2CCCC2)=C1 WWSBRQBNMHIVPT-UHFFFAOYSA-N 0.000 claims 2
- BNLIRBMTTRZPQK-UHFFFAOYSA-N 3-[4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 BNLIRBMTTRZPQK-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 229940125709 anorectic agent Drugs 0.000 claims 2
- 239000002830 appetite depressant Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 claims 1
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 claims 1
- HZJQOVSUPDKFFL-UHFFFAOYSA-N 3-[3,5-dichloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]anilino]-2-methyl-3-oxopropanoic acid Chemical compound ClC1=CC(NC(=O)C(C(O)=O)C)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 HZJQOVSUPDKFFL-UHFFFAOYSA-N 0.000 claims 1
- IKHKYCVSAWFMPR-UHFFFAOYSA-N 3-[3,5-dichloro-4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]anilino]-3-oxopropanoic acid Chemical compound ClC1=CC(NC(=O)CC(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 IKHKYCVSAWFMPR-UHFFFAOYSA-N 0.000 claims 1
- MQQNCVXXSUKWMM-UHFFFAOYSA-N 3-[3,5-dichloro-4-[3-(cyclobutylsulfamoyl)-4-hydroxyphenoxy]anilino]-3-oxopropanoic acid Chemical compound ClC1=CC(NC(=O)CC(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)NC2CCC2)=C1 MQQNCVXXSUKWMM-UHFFFAOYSA-N 0.000 claims 1
- BPWBWVUTMWLOJR-UHFFFAOYSA-N 3-[3-chloro-4-(3-cyclopentylsulfonyl-4-hydroxyphenoxy)-5-methylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C2CCCC2)=C1 BPWBWVUTMWLOJR-UHFFFAOYSA-N 0.000 claims 1
- JFTVCNCOFHCQAP-UHFFFAOYSA-N 3-[3-chloro-4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]-5-methylanilino]-2-methyl-3-oxopropanoic acid Chemical compound ClC1=CC(NC(=O)C(C(O)=O)C)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 JFTVCNCOFHCQAP-UHFFFAOYSA-N 0.000 claims 1
- PEZKCCUGBLAYSQ-UHFFFAOYSA-N 3-[4-(3-cyclopentylsulfonyl-4-hydroxyphenoxy)-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C2CCCC2)=C1 PEZKCCUGBLAYSQ-UHFFFAOYSA-N 0.000 claims 1
- PLBLHOBVRPYSDF-UHFFFAOYSA-N 3-[4-[3-(4-fluorobenzoyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(C(=O)C=2C=CC(F)=CC=2)=C1 PLBLHOBVRPYSDF-UHFFFAOYSA-N 0.000 claims 1
- PVKYYDIPUNAQOX-UHFFFAOYSA-N 3-[4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 PVKYYDIPUNAQOX-UHFFFAOYSA-N 0.000 claims 1
- GHKUCWZCPWQVQJ-UHFFFAOYSA-N 3-[4-[3-[(4-fluorophenyl)-hydroxymethyl]-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(C(O)C=2C=CC(F)=CC=2)=C1 GHKUCWZCPWQVQJ-UHFFFAOYSA-N 0.000 claims 1
- KKECGHUEAORUNI-UHFFFAOYSA-N 3-[4-[3-[cyclobutyl(methyl)carbamoyl]-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound C=1C(OC=2C(=CC(NC(=O)CC(O)=O)=CC=2C)C)=CC=C(O)C=1C(=O)N(C)C1CCC1 KKECGHUEAORUNI-UHFFFAOYSA-N 0.000 claims 1
- 208000028257 Joubert syndrome with oculorenal defect Diseases 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 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 1
- 229960002802 bromocriptine Drugs 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 229960004597 dexfenfluramine Drugs 0.000 claims 1
- 229960001582 fenfluramine Drugs 0.000 claims 1
- ZGWCRLBAKZQOHZ-UHFFFAOYSA-N methyl 3-[3,5-dichloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]anilino]-2-methyl-3-oxopropanoate Chemical compound ClC1=CC(NC(=O)C(C)C(=O)OC)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 ZGWCRLBAKZQOHZ-UHFFFAOYSA-N 0.000 claims 1
- PUFDJBDEXMXFPW-UHFFFAOYSA-N methyl 3-[3,5-dichloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]anilino]-3-oxopropanoate Chemical compound ClC1=CC(NC(=O)CC(=O)OC)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 PUFDJBDEXMXFPW-UHFFFAOYSA-N 0.000 claims 1
- OKLITAWPWWVQMA-UHFFFAOYSA-N methyl 3-[3-chloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-5-methylanilino]-2-methyl-3-oxopropanoate Chemical compound ClC1=CC(NC(=O)C(C)C(=O)OC)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 OKLITAWPWWVQMA-UHFFFAOYSA-N 0.000 claims 1
- OBCARBJWBGIPBZ-UHFFFAOYSA-N methyl 3-[3-chloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-5-methylanilino]-3-oxopropanoate Chemical compound ClC1=CC(NC(=O)CC(=O)OC)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 OBCARBJWBGIPBZ-UHFFFAOYSA-N 0.000 claims 1
- SCLIPPUTZFICKX-UHFFFAOYSA-N methyl 3-[3-chloro-4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]-5-methylanilino]-3-oxopropanoate Chemical compound ClC1=CC(NC(=O)CC(=O)OC)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 SCLIPPUTZFICKX-UHFFFAOYSA-N 0.000 claims 1
- DYHASJMAUPAEIY-UHFFFAOYSA-N methyl 3-[4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-methyl-3-oxopropanoate Chemical compound CC1=CC(NC(=O)C(C)C(=O)OC)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 DYHASJMAUPAEIY-UHFFFAOYSA-N 0.000 claims 1
- ABIODVVYVWPYKR-UHFFFAOYSA-N methyl 3-[4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoate Chemical compound CC1=CC(NC(=O)CC(=O)OC)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 ABIODVVYVWPYKR-UHFFFAOYSA-N 0.000 claims 1
- 238000001783 near-resonance Rayleigh scattering spectroscopy Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 229960003562 phentermine Drugs 0.000 claims 1
- 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 1
- 229960004425 sibutramine Drugs 0.000 claims 1
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 102000004877 Insulin Human genes 0.000 description 10
- 108090001061 Insulin Proteins 0.000 description 10
- 229940125396 insulin Drugs 0.000 description 10
- 239000005495 thyroid hormone Substances 0.000 description 10
- 229940036555 thyroid hormone Drugs 0.000 description 10
- 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 9
- 230000000694 effects Effects 0.000 description 9
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 7
- 150000002632 lipids Chemical class 0.000 description 7
- 230000000929 thyromimetic effect Effects 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 230000003698 anagen phase Effects 0.000 description 5
- 230000034994 death Effects 0.000 description 5
- 231100000517 death Toxicity 0.000 description 5
- 206010007559 Cardiac failure congestive Diseases 0.000 description 4
- 206010019280 Heart failures Diseases 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 4
- 230000003779 hair growth Effects 0.000 description 4
- 230000003797 telogen phase Effects 0.000 description 4
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- 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 3
- 102000011845 Iodide peroxidase Human genes 0.000 description 3
- 108010036012 Iodide peroxidase Proteins 0.000 description 3
- KKCIOUWDFWQUBT-AWEZNQCLSA-N L-thyronine Chemical compound C1=CC(C[C@H](N)C(O)=O)=CC=C1OC1=CC=C(O)C=C1 KKCIOUWDFWQUBT-AWEZNQCLSA-N 0.000 description 3
- 206010041277 Sodium retention Diseases 0.000 description 3
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 210000003780 hair follicle Anatomy 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 2
- 208000007530 Essential hypertension Diseases 0.000 description 2
- 208000001647 Renal Insufficiency Diseases 0.000 description 2
- 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 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000003472 antidiabetic agent Substances 0.000 description 2
- 210000000709 aorta Anatomy 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000003778 catagen phase Effects 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 210000004207 dermis Anatomy 0.000 description 2
- 230000002500 effect on skin Effects 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229940126904 hypoglycaemic agent Drugs 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 201000006370 kidney failure Diseases 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 239000000203 mixture Chemical class 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003538 oral antidiabetic agent Substances 0.000 description 2
- 229940127209 oral hypoglycaemic agent Drugs 0.000 description 2
- 230000036284 oxygen consumption Effects 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 210000001685 thyroid gland Anatomy 0.000 description 2
- 229940034208 thyroxine Drugs 0.000 description 2
- XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 2
- 210000005166 vasculature Anatomy 0.000 description 2
- UPLPHRJJTCUQAY-WIRWPRASSA-N 2,3-thioepoxy madol Chemical compound C([C@@H]1CC2)[C@@H]3S[C@@H]3C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@](C)(O)[C@@]2(C)CC1 UPLPHRJJTCUQAY-WIRWPRASSA-N 0.000 description 1
- SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical class O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 description 1
- 239000005541 ACE inhibitor Substances 0.000 description 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 208000031104 Arterial Occlusive disease Diseases 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
- 208000006029 Cardiomegaly Diseases 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 208000032928 Dyslipidaemia Diseases 0.000 description 1
- 102000016942 Elastin Human genes 0.000 description 1
- 108010014258 Elastin Proteins 0.000 description 1
- 208000017701 Endocrine disease Diseases 0.000 description 1
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 1
- 102100033417 Glucocorticoid receptor Human genes 0.000 description 1
- 208000002705 Glucose Intolerance Diseases 0.000 description 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
- 102100022631 Glutamate receptor ionotropic, NMDA 2C Human genes 0.000 description 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010020850 Hyperthyroidism Diseases 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- XUIIKFGFIJCVMT-LBPRGKRZSA-N L-thyroxine Chemical compound IC1=CC(C[C@H]([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-LBPRGKRZSA-N 0.000 description 1
- 108010028554 LDL Cholesterol Proteins 0.000 description 1
- 208000007177 Left Ventricular Hypertrophy Diseases 0.000 description 1
- 208000017170 Lipid metabolism disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102000016611 Proteoglycans Human genes 0.000 description 1
- 108010067787 Proteoglycans Proteins 0.000 description 1
- 208000004531 Renal Artery Obstruction Diseases 0.000 description 1
- 206010038378 Renal artery stenosis Diseases 0.000 description 1
- 102100028255 Renin Human genes 0.000 description 1
- 108090000783 Renin Proteins 0.000 description 1
- 206010039921 Selenium deficiency Diseases 0.000 description 1
- 102000008114 Selenoproteins Human genes 0.000 description 1
- 108010074686 Selenoproteins Proteins 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 229940054021 anxiolytics diphenylmethane derivative Drugs 0.000 description 1
- 208000021328 arterial occlusion Diseases 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 210000002469 basement membrane Anatomy 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000001627 cerebral artery Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 229920002549 elastin Polymers 0.000 description 1
- 230000008451 emotion Effects 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 230000003659 hair regrowth Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 1
- 230000000910 hyperinsulinemic effect Effects 0.000 description 1
- 201000008980 hyperinsulinism Diseases 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000002366 lipolytic effect Effects 0.000 description 1
- 230000008604 lipoprotein metabolism Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004630 mental health Effects 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 230000036513 peripheral conductance Effects 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 208000028591 pheochromocytoma Diseases 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 230000004800 psychological effect Effects 0.000 description 1
- 230000035485 pulse pressure Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 108091008646 testicular receptors Proteins 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000003749 thyromimetic agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000005167 vascular cell Anatomy 0.000 description 1
- 230000006444 vascular growth Effects 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- 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
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
- A61P5/16—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/80—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms having carbon atoms of carboxamide groups and keto groups bound to the same carbon atom, e.g. acetoacetamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19361800P | 2000-03-31 | 2000-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200207444B true ZA200207444B (en) | 2003-09-17 |
Family
ID=22714346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200207444A ZA200207444B (en) | 2000-03-31 | 2002-09-17 | Malonamic acids and derivatives thereof as thyroid receptor ligands. |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US20070173548A1 (fr) |
| EP (1) | EP1268404B1 (fr) |
| JP (1) | JP3866977B2 (fr) |
| KR (1) | KR20020089420A (fr) |
| CN (1) | CN1422246A (fr) |
| AP (1) | AP2002002634A0 (fr) |
| AR (1) | AR033516A1 (fr) |
| AT (1) | ATE382602T1 (fr) |
| AU (1) | AU2001237665A1 (fr) |
| BG (1) | BG107036A (fr) |
| BR (1) | BR0109625A (fr) |
| CA (1) | CA2403902C (fr) |
| CR (1) | CR6742A (fr) |
| CZ (1) | CZ20023190A3 (fr) |
| DE (1) | DE60132181D1 (fr) |
| DZ (1) | DZ3276A1 (fr) |
| EA (1) | EA200200921A1 (fr) |
| EE (1) | EE200200566A (fr) |
| GT (1) | GT200100041A (fr) |
| HK (1) | HK1052498A1 (fr) |
| HU (1) | HUP0300329A3 (fr) |
| IL (1) | IL151376A0 (fr) |
| IS (1) | IS6516A (fr) |
| MA (1) | MA26886A1 (fr) |
| MX (1) | MXPA02009702A (fr) |
| NO (1) | NO20024639L (fr) |
| NZ (1) | NZ520660A (fr) |
| OA (1) | OA12237A (fr) |
| PA (1) | PA8513801A1 (fr) |
| PE (1) | PE20011186A1 (fr) |
| PL (1) | PL358596A1 (fr) |
| SK (1) | SK13762002A3 (fr) |
| SV (1) | SV2002000357A (fr) |
| TN (1) | TNSN01048A1 (fr) |
| TR (1) | TR200202249T2 (fr) |
| WO (1) | WO2001072692A1 (fr) |
| YU (1) | YU74102A (fr) |
| ZA (1) | ZA200207444B (fr) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6790978B2 (en) | 1999-03-29 | 2004-09-14 | Novartis Ag | Thyromimetic organic compounds |
| US6599942B1 (en) | 1999-03-29 | 2003-07-29 | Novartis Ag | Thyromimetic organic compounds |
| PL201790B1 (pl) * | 2000-02-17 | 2009-05-29 | Bristol Myers Squibb Co | Anilinopochodny ligand dla receptora tarczycy, jego zastosowanie i kompozycja farmaceutyczna |
| WO2002051805A1 (fr) * | 2000-12-27 | 2002-07-04 | Bayer Aktiengesellschaft | Derives de l'indole utilises comme ligands de recepteurs de la thyroide |
| GB2374009A (en) * | 2001-02-12 | 2002-10-09 | Novartis Ag | Method of treating hair loss |
| KR20040027927A (ko) | 2001-08-24 | 2004-04-01 | 카로 바이오 아베 | 심장 및 대사 장애의 치료를 위해 주요 환이 치환된갑상선 수용체 길항근 |
| US6806381B2 (en) | 2001-11-02 | 2004-10-19 | Bristol-Myers Squibb Company | Process for the preparation of aniline-derived thyroid receptor ligands |
| TW200504021A (en) | 2003-01-24 | 2005-02-01 | Bristol Myers Squibb Co | Substituted anilide ligands for the thyroid receptor |
| CA2546601A1 (fr) | 2003-11-19 | 2005-06-09 | Metabasis Therapeutics, Inc. | Nouvelles substances thyromimetiques contenant du phosphore |
| WO2006128058A2 (fr) | 2005-05-26 | 2006-11-30 | Metabasis Therapeutics, Inc. | Composes thyromimetiques utilises pour traiter les maladies hepatiques graisseuses |
| GB0606201D0 (en) * | 2006-03-28 | 2006-05-10 | Karobio Ab | Improved crytalline material |
| RU2009108280A (ru) | 2006-08-08 | 2010-09-20 | Санофи-Авентис (Fr) | Ариламиноарилалкилзамещенные имидазолидин-2,4-дионы, способы их получения, содержащие эти соединения лекарственные средства и их применение |
| CN102137837A (zh) * | 2008-04-11 | 2011-07-27 | 株式会社医药分子设计研究所 | Pai-1抑制剂 |
| US8633245B2 (en) * | 2008-04-11 | 2014-01-21 | Institute Of Medicinal Molecular Design, Inc. | PAI-1 inhibitor |
| AR072707A1 (es) | 2008-07-09 | 2010-09-15 | Sanofi Aventis | Compuestos heterociclicos, procesos para su preparacion, medicamentos que comprenden estos compuestos y el uso de los mismos |
| MX2011004347A (es) | 2008-10-27 | 2011-05-25 | Cadila Healthcare Ltd | Ligandos de receptores de la tiroides. |
| WO2010068601A1 (fr) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | Hydrate de fluoroglycoside hétéroaromatique cristallin, ses procédés de fabrication, ses procédés d'utilisation et compositions pharmaceutiques le contenant |
| WO2010086878A2 (fr) | 2009-01-09 | 2010-08-05 | Cadila Healthcare Limited | Modulateurs des récepteurs de la thyroïde |
| EP2470552B1 (fr) | 2009-08-26 | 2013-11-13 | Sanofi | Nouveaux hydrates de fluoroglycoside hétéroaromatiques cristallins, produits pharmaceutiques comprenant ces composés et leur utilisation |
| US8846666B2 (en) | 2011-03-08 | 2014-09-30 | Sanofi | Oxathiazine derivatives which are substituted with benzyl or heteromethylene groups, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| EP2683702B1 (fr) | 2011-03-08 | 2014-12-24 | Sanofi | Nouveaux dérivés de phényle-oxathiazine substitués, leur procédé de fabrication, médicament contenant ces liaisons et son utilisation |
| EP2683703B1 (fr) | 2011-03-08 | 2015-05-27 | Sanofi | Nouveaux dérivés phényl-oxathiazine substitués, procédé pour leur préparation, agent pharmaceutique contenant ces composés et leur utilisation |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2766349B1 (fr) | 2011-03-08 | 2016-06-01 | Sanofi | Dérivés d'oxathiazine substitués par des carbocycles ou des hétérocycles, leur procédé de préparation, médicaments contenant ces composés et leur utilisation |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683698B1 (fr) | 2011-03-08 | 2017-10-04 | Sanofi | Dérivés benzyl-oxathiazine substitués avec adamantane ou noradamantane, médicaments contenant ces composés et leur utilisation |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683700B1 (fr) | 2011-03-08 | 2015-02-18 | Sanofi | Dérivés d'oxathiazine tétra-substitués, leur procédé de fabrication, leur utilisation comme médicament ainsi que médicaments en étant pourvu et leur utilisation |
| EP2567959B1 (fr) | 2011-09-12 | 2014-04-16 | Sanofi | Dérivés d'amide d'acide 6-(4-hydroxy-phényl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylique en tant qu'inhibiteurs de kinase |
| DK2695611T3 (en) | 2012-08-06 | 2015-01-05 | Wolff August Gmbh & Co Kg Arzneimittel Dr | Eprotirome for use in the prevention and / or treatment of hair disorders and their compositions |
| CA2891122C (fr) | 2012-11-14 | 2021-07-20 | The Johns Hopkins University | Methodes et compositions pour le traitement de la schizophrenie |
| US20170112741A1 (en) * | 2014-04-09 | 2017-04-27 | Goldcrest Medicine Institute Co., Ltd. | Agent for ameliorating skin symptom, hair growth agent or slimming agent |
| MX2019005730A (es) | 2016-11-21 | 2019-10-21 | Viking Therapeutics Inc | Metodo para tratar enfermedad de almacenamiento de glucogeno. |
| EA201992703A1 (ru) | 2017-06-05 | 2020-04-15 | Вайкинг Терапьютикс, Инк. | Композиции для лечения фиброза |
| CN107474007B (zh) * | 2017-08-28 | 2019-04-19 | 上海再启生物技术有限公司 | 一种制备3，6-二羟基苯二甲酰亚胺的方法 |
| EP3768690A4 (fr) | 2018-03-22 | 2021-11-24 | Viking Therapeutics, Inc. | Formes cristallines et procédés de production de formes cristallines d'un composé |
| WO2020117962A1 (fr) | 2018-12-05 | 2020-06-11 | Viking Therapeutics, Inc. | Compositions pour le traitement de la fibrose et de l'inflammation |
| CN112300133B (zh) * | 2019-07-31 | 2024-07-30 | 深圳微芯生物科技股份有限公司 | 一种杂环化合物及其应用 |
| EP3878837A1 (fr) * | 2020-03-11 | 2021-09-15 | OM Pharma SA | Dérivés d'hydroquinone 2,5- ou 2,6-disubstitutuées avec au moins un groupe carboxy, sulfo ou amido utiles comme médicaments |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069343A (en) * | 1973-03-23 | 1978-01-17 | American Home Products Corporation | Oxamic acid derivatives for the prevention of immediate type hypersensitivity reactions |
| US4554290A (en) * | 1983-06-17 | 1985-11-19 | Ciba-Geigy Corporation | Oxamic acid derivatives |
| US5061798A (en) * | 1985-01-18 | 1991-10-29 | Smith Kline & French Laboratories, Ltd. | Benzyl pyridyl and pyridazinyl compounds |
| GB8501372D0 (en) * | 1985-01-18 | 1985-02-20 | Smith Kline French Lab | Chemical compounds |
| US5232947A (en) * | 1988-07-04 | 1993-08-03 | Meiji Seika Kaisha, Ltd. | Oxamic acid compounds and pharmaceutical composition for use in improvement of damaged cerebral functions of brain |
| US5284971A (en) * | 1992-07-16 | 1994-02-08 | Syntex (U.S.A.) Inc. | 4-(3-cyclohexyl-4-hydroxy or-methoxy phenylsulfonyl) 3,5 dibromo phenyl acetic thyromimetic cholesterol-lowering agents |
| DK0580550T3 (da) * | 1992-07-21 | 1998-02-02 | Ciba Geigy Ag | Oxamidsyrederivater som hypercholesterolæmiske midler |
| CO5160290A1 (es) * | 1999-03-29 | 2002-05-30 | Novartis Ag | Derivados de acido fenoxifeniloxamico sustituido . |
| CA2374263A1 (fr) * | 1999-06-01 | 2000-12-07 | The University Of Texas Southwestern Medical Center | Methode de traitement de la perte des cheveux a l'aide de derives de diphenylether |
| US6664291B2 (en) * | 2000-03-31 | 2003-12-16 | Pfizer, Inc. | Malonamic acids and derivatives thereof as thyroid receptor ligands |
-
2001
- 2001-03-07 PL PL01358596A patent/PL358596A1/xx not_active Application Discontinuation
- 2001-03-07 AT AT01910082T patent/ATE382602T1/de not_active IP Right Cessation
- 2001-03-07 KR KR1020027013044A patent/KR20020089420A/ko not_active Application Discontinuation
- 2001-03-07 MX MXPA02009702A patent/MXPA02009702A/es active IP Right Grant
- 2001-03-07 EA EA200200921A patent/EA200200921A1/ru unknown
- 2001-03-07 DE DE60132181T patent/DE60132181D1/de not_active Expired - Lifetime
- 2001-03-07 EP EP01910082A patent/EP1268404B1/fr not_active Expired - Lifetime
- 2001-03-07 CZ CZ20023190A patent/CZ20023190A3/cs unknown
- 2001-03-07 OA OA1200200299A patent/OA12237A/en unknown
- 2001-03-07 IL IL15137601A patent/IL151376A0/xx unknown
- 2001-03-07 NZ NZ520660A patent/NZ520660A/en not_active Application Discontinuation
- 2001-03-07 TR TR2002/02249T patent/TR200202249T2/xx unknown
- 2001-03-07 SK SK1376-2002A patent/SK13762002A3/sk not_active Application Discontinuation
- 2001-03-07 DZ DZ013276A patent/DZ3276A1/fr active
- 2001-03-07 CA CA002403902A patent/CA2403902C/fr not_active Expired - Fee Related
- 2001-03-07 JP JP2001570607A patent/JP3866977B2/ja not_active Expired - Fee Related
- 2001-03-07 EE EEP200200566A patent/EE200200566A/xx unknown
- 2001-03-07 CN CN01807559A patent/CN1422246A/zh active Pending
- 2001-03-07 AU AU2001237665A patent/AU2001237665A1/en not_active Abandoned
- 2001-03-07 YU YU74102A patent/YU74102A/sh unknown
- 2001-03-07 AP APAP/P/2002/002634A patent/AP2002002634A0/en unknown
- 2001-03-07 BR BR0109625-7A patent/BR0109625A/pt not_active IP Right Cessation
- 2001-03-07 WO PCT/IB2001/000317 patent/WO2001072692A1/fr active IP Right Grant
- 2001-03-07 HU HU0300329A patent/HUP0300329A3/hu unknown
- 2001-03-16 PA PA20018513801A patent/PA8513801A1/es unknown
- 2001-03-19 GT GT200100041A patent/GT200100041A/es unknown
- 2001-03-28 PE PE2001000290A patent/PE20011186A1/es not_active Application Discontinuation
- 2001-03-29 AR ARP010101509A patent/AR033516A1/es unknown
- 2001-03-30 TN TNTNSN01048A patent/TNSN01048A1/fr unknown
- 2001-03-30 SV SV2001000357A patent/SV2002000357A/es not_active Application Discontinuation
-
2002
- 2002-08-21 IS IS6516A patent/IS6516A/is unknown
- 2002-08-26 BG BG107036A patent/BG107036A/bg unknown
- 2002-08-28 CR CR6742A patent/CR6742A/es not_active Application Discontinuation
- 2002-09-17 ZA ZA200207444A patent/ZA200207444B/en unknown
- 2002-09-24 MA MA26837A patent/MA26886A1/fr unknown
- 2002-09-27 NO NO20024639A patent/NO20024639L/no not_active Application Discontinuation
-
2003
- 2003-07-08 HK HK03104860.6A patent/HK1052498A1/zh unknown
-
2007
- 2007-03-07 US US11/715,035 patent/US20070173548A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200207444B (en) | Malonamic acids and derivatives thereof as thyroid receptor ligands. | |
| RU2388466C2 (ru) | Производные феноксиалкилкарбоновых кислот при лечении воспалительных заболеваний | |
| JP2004512302A (ja) | 内皮機能不全治療用のフェノフィブラートと補酵素ｑ１０との組み合わせ | |
| EP1924326B1 (fr) | Réduction d un dommage myocardique et de l incidence d une arythmie survenant à la suite d une perte, d une réduction ou d une interruption de la circulation coronarienne | |
| CA2390276A1 (fr) | Nouveaux composes utiles pour traiter le diabete et les pathologies associees | |
| KR101391905B1 (ko) | 물질대사 장애의 치료용 화합물 | |
| CZ298745B6 (cs) | Farmaceutická kombinace, farmaceutický přípravek, způsob jeho výroby a použití kombinace | |
| AU2002352826A1 (en) | Methods of reversing and preventing cardiovascular pathologies | |
| EP1451138A2 (fr) | Methode permettant d'inverser le processus de maladies cardio-vasculaires et de prevenir ces dernieres | |
| CA2430282C (fr) | Utilisation de composes 6-dimethylaminomethyle-1-phenylcyclohexane subs titues pour traiter l'incontinence urinaire | |
| WO1997047295A1 (fr) | Acides acetiques methoxy-benzylidene-indenyl et propioniques substitues destines au traitement de patients presentant des lesions precancereuses | |
| KR19990023705A (ko) | 심부전증 치료용 약학 조성물 | |
| EP4011862A1 (fr) | Nouveau composé pour l'inhibition de l'histone acétyltransférase p300 et composition anti-fibrose le comprenant | |
| US20030045582A1 (en) | Method for treating hyperglycemia | |
| US20040147600A1 (en) | Pharmaceutical combination comprising either (s)-2-ethoxy-3 [4-(2-{4-methane sulfonyl oxyphenyl} ethoxy)phenyl]propanoic acid or 3-{4-[2-(4-tert-butoxy carbonylamino phenyl)ethoxy]phenyl}-(s-2ethoxy propanoic acid and insulin | |
| KR102301274B1 (ko) | 히스톤 아세틸트렌스퍼라제 p300 억제용 신규 화합물 및 이를 포함하는 항섬유화 조성물 | |
| JP2011509942A (ja) | 代謝異常の治療のための化合物 | |
| CA2309588A1 (fr) | Associations statine-inhibiteur de metalloprotease matricielle | |
| AU2006284513A1 (en) | Reducing myocardial damage and the incidence of arrhythmia arising from loss, reduction or interruption in coronary blood flow | |
| US20050153870A1 (en) | Medicinal composition for diagnosis, prevention, or therapy of multiple risk factor syndrome | |
| CA2447716A1 (fr) | Agents preventifs ou remedes pour maladies provoquees par des troubles cerebrovasculaires | |
| US20040157927A1 (en) | Pharmaceutical combination comprising either (s)-2-ethoxy-3-[4-(2-{4-methane sulfonyl oxyphenyl} ethoxy) phenyl] propanoic acid or 3-{-4-[2-(4-tert-butoxy carbonyl aminophenyl) ethoxy] phenyl}-(s)-2-ethoxy propanoic acid and a sulonylurea | |
| CN114099679A (zh) | 钠-葡萄糖协同转运蛋白2抑制剂的新用途 | |
| RU2276603C1 (ru) | Способ лечения безболевой ишемии миокарда | |
| CA2448643A1 (fr) | Preparation pharmaceutique comprenant soit de l'acide (s)-2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl] propanoique, soit de l'acide 3-{4-[2-(4-$i(tert)-butoxycarbonylaminophenyl)ethoxy]phenyl}-(s)-2-ethoxy propanoique, et un medicament de biguanide. |