ZA200106730B - Oxamic acids and derivatives as thyroid receptor ligands. - Google Patents
Oxamic acids and derivatives as thyroid receptor ligands. Download PDFInfo
- Publication number
- ZA200106730B ZA200106730B ZA200106730A ZA200106730A ZA200106730B ZA 200106730 B ZA200106730 B ZA 200106730B ZA 200106730 A ZA200106730 A ZA 200106730A ZA 200106730 A ZA200106730 A ZA 200106730A ZA 200106730 B ZA200106730 B ZA 200106730B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydroxy
- alkyl
- phenoxy
- phenyl
- oxamic acid
- Prior art date
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- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 title claims description 23
- 239000003446 ligand Substances 0.000 title description 3
- 102000004217 thyroid hormone receptors Human genes 0.000 title description 3
- 108090000721 thyroid hormone receptors Proteins 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000002837 carbocyclic group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- -1 (D) Cs Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000004043 oxo group Chemical group O=* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000000651 prodrug Substances 0.000 claims description 9
- 229940002612 prodrug Drugs 0.000 claims description 9
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 201000001320 Atherosclerosis Diseases 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 208000024799 Thyroid disease Diseases 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 206010003119 arrhythmia Diseases 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 208000003532 hypothyroidism Diseases 0.000 claims description 4
- 230000002989 hypothyroidism Effects 0.000 claims description 4
- 208000017520 skin disease Diseases 0.000 claims description 4
- 208000021510 thyroid gland disease Diseases 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 3
- 208000029078 coronary artery disease Diseases 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- 239000003085 diluting agent Substances 0.000 claims 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 4
- 229940086609 Lipase inhibitor Drugs 0.000 claims 3
- 229940125709 anorectic agent Drugs 0.000 claims 3
- 239000002830 appetite depressant Substances 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 159000000000 sodium salts Chemical group 0.000 claims 3
- CEYPDXWCYTVSDN-UHFFFAOYSA-N 2-[4-[(7-hydroxy-2,3-dihydro-1h-inden-4-yl)oxy]-3,5-dimethylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(C)=C1OC1=CC=C(O)C2=C1CCC2 CEYPDXWCYTVSDN-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 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 2
- 239000002552 dosage form Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000004340 exo-2-norbornyl group Chemical group [H]C1([H])C([H])([H])[C@@]2([H])C([H])([H])[C@]1([H])C([H])([H])[C@]2([H])* 0.000 claims 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- NOSHQXUEOURLQH-UHFFFAOYSA-N 2-[3,5-dichloro-4-[3-(cyclopropylmethylsulfonyl)-4-hydroxyphenoxy]anilino]-2-oxoacetic acid Chemical compound ClC1=CC(NC(=O)C(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CC2)=C1 NOSHQXUEOURLQH-UHFFFAOYSA-N 0.000 claims 1
- ZOFRNCXBRYIWKT-UHFFFAOYSA-N 2-[3,5-dichloro-4-[3-[cyclobutyl(methyl)carbamoyl]-4-hydroxyphenoxy]anilino]-2-oxoacetic acid Chemical compound C=1C(OC=2C(=CC(NC(=O)C(O)=O)=CC=2Cl)Cl)=CC=C(O)C=1C(=O)N(C)C1CCC1 ZOFRNCXBRYIWKT-UHFFFAOYSA-N 0.000 claims 1
- XIALDZZQMKFCMN-UHFFFAOYSA-N 2-[3-chloro-4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 XIALDZZQMKFCMN-UHFFFAOYSA-N 0.000 claims 1
- GJFODAFOPHZYFS-UHFFFAOYSA-N 2-[4-[3-[cyclobutyl(methyl)carbamoyl]-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetic acid Chemical compound C=1C(OC=2C(=CC(NC(=O)C(O)=O)=CC=2C)C)=CC=C(O)C=1C(=O)N(C)C1CCC1 GJFODAFOPHZYFS-UHFFFAOYSA-N 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- ZIKMXOJEFAWJDO-UHFFFAOYSA-N ethyl 2-[4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound CC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 ZIKMXOJEFAWJDO-UHFFFAOYSA-N 0.000 claims 1
- UBYIHMDIEVAHSD-UHFFFAOYSA-N ethyl 2-[4-[3-[cyclobutyl(methyl)carbamoyl]-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound CC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(C(=O)N(C)C2CCC2)=C1 UBYIHMDIEVAHSD-UHFFFAOYSA-N 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 239000005495 thyroid hormone Substances 0.000 description 9
- 229940036555 thyroid hormone Drugs 0.000 description 9
- 230000000747 cardiac effect Effects 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000000929 thyromimetic effect Effects 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002253 acid Substances 0.000 description 2
- 239000003529 anticholesteremic agent Substances 0.000 description 2
- 239000003524 antilipemic agent Substances 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 230000036284 oxygen consumption Effects 0.000 description 2
- 210000001685 thyroid gland Anatomy 0.000 description 2
- VSWSDTLXDWESGZ-AWEZNQCLSA-N (2s)-3-[4-(4-hydroxyphenoxy)phenyl]-2-(iodoamino)propanoic acid Chemical class C1=CC(C[C@@H](C(=O)O)NI)=CC=C1OC1=CC=C(O)C=C1 VSWSDTLXDWESGZ-AWEZNQCLSA-N 0.000 description 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
- 208000006029 Cardiomegaly Diseases 0.000 description 1
- 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 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010020850 Hyperthyroidism Diseases 0.000 description 1
- 102000011845 Iodide peroxidase Human genes 0.000 description 1
- 108010036012 Iodide peroxidase Proteins 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
- 241001465754 Metazoa Species 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000002366 lipolytic effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 230000036513 peripheral conductance Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 230000035485 pulse pressure Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000003749 thyromimetic agent Substances 0.000 description 1
- 229940034208 thyroxine Drugs 0.000 description 1
- 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 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
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- 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
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- C07C2601/14—The ring being saturated
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- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
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ZA200106730A ZA200106730B (en) | 1999-03-01 | 2001-08-15 | Oxamic acids and derivatives as thyroid receptor ligands. |
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GB0015205D0 (en) * | 2000-06-21 | 2000-08-09 | Karobio Ab | Bioisosteric thyroid receptor ligands and method |
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JP2020500199A (ja) | 2016-11-21 | 2020-01-09 | バイキング・セラピューティクス・インコーポレイテッド | グリコーゲン蓄積症の治療方法 |
EP3634426A4 (fr) | 2017-06-05 | 2021-04-07 | Viking Therapeutics, Inc. | Compositions pour le traitement d'une fibrose |
US11787828B2 (en) | 2018-03-22 | 2023-10-17 | Viking Therapeutics, Inc. | Crystalline forms and methods of producing crystalline forms of a compound |
AU2021306314A1 (en) * | 2020-07-10 | 2023-02-09 | Aligos Therapeutics, Inc. | Modulators of THR-β and methods of use thereof |
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 |
GB8501372D0 (en) | 1985-01-18 | 1985-02-20 | Smith Kline French Lab | Chemical compounds |
US5061798A (en) | 1985-01-18 | 1991-10-29 | Smith Kline & French Laboratories, Ltd. | Benzyl pyridyl and pyridazinyl 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 |
GB9816935D0 (en) * | 1998-08-05 | 1998-09-30 | Karobio Ab | Novel glucocortoid and thyroid receptor ligands for the treatment of metabolic disorders |
CN1345303A (zh) * | 1999-03-01 | 2002-04-17 | 辉瑞产品公司 | 用作甲状腺受体配体的草氨酸及衍生物 |
CO5160290A1 (es) | 1999-03-29 | 2002-05-30 | Novartis Ag | Derivados de acido fenoxifeniloxamico sustituido . |
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2000
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- 2000-02-21 EP EP00902835A patent/EP1157001B1/fr not_active Expired - Lifetime
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- 2000-02-21 YU YU63301A patent/YU63301A/sh unknown
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- 2000-02-21 AU AU24575/00A patent/AU772282B2/en not_active Ceased
- 2000-02-21 WO PCT/IB2000/000183 patent/WO2000051971A1/fr not_active Application Discontinuation
- 2000-02-21 DE DE60012700T patent/DE60012700T2/de not_active Expired - Fee Related
- 2000-02-21 EE EEP200100464A patent/EE200100464A/xx unknown
- 2000-02-28 AR ARP000100869A patent/AR033791A1/es not_active Application Discontinuation
- 2000-02-28 US US09/514,862 patent/US6326398B1/en not_active Expired - Fee Related
- 2000-02-29 GT GT200000025AK patent/GT200000025AA/es unknown
- 2000-02-29 MA MA25916A patent/MA26723A1/fr unknown
- 2000-02-29 PE PE2000000166A patent/PE20001483A1/es not_active Application Discontinuation
- 2000-02-29 DZ DZ000039A patent/DZ3020A1/fr active
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2001
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2002
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- 2002-12-20 US US10/324,948 patent/US20030114521A1/en not_active Abandoned
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2004
- 2004-12-06 JP JP2004352241A patent/JP2005162759A/ja active Pending
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