MX2007001539A - Compuestos heterociclicos como agentes farmaceuticos. - Google Patents
Compuestos heterociclicos como agentes farmaceuticos.Info
- Publication number
- MX2007001539A MX2007001539A MX2007001539A MX2007001539A MX2007001539A MX 2007001539 A MX2007001539 A MX 2007001539A MX 2007001539 A MX2007001539 A MX 2007001539A MX 2007001539 A MX2007001539 A MX 2007001539A MX 2007001539 A MX2007001539 A MX 2007001539A
- Authority
- MX
- Mexico
- Prior art keywords
- optionally substituted
- substituted
- heterocyclyl
- heteroaryl
- aryl
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 239000008177 pharmaceutical agent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 175
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 97
- 239000000203 mixture Substances 0.000 claims abstract description 97
- 238000000034 method Methods 0.000 claims abstract description 67
- 230000000694 effects Effects 0.000 claims abstract description 56
- 201000010099 disease Diseases 0.000 claims abstract description 51
- 208000035475 disorder Diseases 0.000 claims abstract description 46
- 208000024891 symptom Diseases 0.000 claims abstract description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 266
- 125000000623 heterocyclic group Chemical group 0.000 claims description 262
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 232
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 227
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 212
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 209
- 125000005843 halogen group Chemical group 0.000 claims description 190
- 125000000217 alkyl group Chemical group 0.000 claims description 187
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 184
- 125000003118 aryl group Chemical group 0.000 claims description 175
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 174
- 125000002577 pseudohalo group Chemical group 0.000 claims description 174
- 125000001424 substituent group Chemical group 0.000 claims description 162
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 161
- 125000001188 haloalkyl group Chemical group 0.000 claims description 146
- -1 3-acetylphenylimino Chemical group 0.000 claims description 110
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 239000001257 hydrogen Substances 0.000 claims description 96
- 125000003107 substituted aryl group Chemical group 0.000 claims description 88
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 79
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 68
- 125000003342 alkenyl group Chemical group 0.000 claims description 63
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 63
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims description 59
- 125000000304 alkynyl group Chemical group 0.000 claims description 59
- 108020004017 nuclear receptors Proteins 0.000 claims description 58
- 150000002431 hydrogen Chemical class 0.000 claims description 57
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 57
- 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 claims description 42
- 102100038495 Bile acid receptor Human genes 0.000 claims description 40
- 101000603876 Homo sapiens Bile acid receptor Proteins 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- 229940107161 cholesterol Drugs 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 239000000556 agonist Substances 0.000 claims description 15
- 239000005557 antagonist Substances 0.000 claims description 15
- 235000012000 cholesterol Nutrition 0.000 claims description 15
- 206010012601 diabetes mellitus Diseases 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 13
- 239000003937 drug carrier Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 12
- 201000001320 Atherosclerosis Diseases 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 230000004060 metabolic process Effects 0.000 claims description 10
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 9
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 8
- 206010008635 Cholestasis Diseases 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 239000003613 bile acid Substances 0.000 claims description 8
- 230000007870 cholestasis Effects 0.000 claims description 8
- 231100000359 cholestasis Toxicity 0.000 claims description 8
- 201000001421 hyperglycemia Diseases 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 7
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 7
- 206010049287 Lipodystrophy acquired Diseases 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 7
- 208000006132 lipodystrophy Diseases 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 6
- 230000015556 catabolic process Effects 0.000 claims description 6
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 230000009102 absorption Effects 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 235000006708 antioxidants Nutrition 0.000 claims description 5
- 239000012190 activator Substances 0.000 claims description 4
- 230000029142 excretion Effects 0.000 claims description 4
- 229940088597 hormone Drugs 0.000 claims description 4
- 239000005556 hormone Substances 0.000 claims description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
- UEKDOPPDCYNGHM-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3,5-dibenzyl-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C1N(CC=2C=CC=CC=2)C(=O)C(CC=2C=CC=CC=2)S1 UEKDOPPDCYNGHM-UHFFFAOYSA-N 0.000 claims description 3
- HLSDYWFUKOZJTE-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-(2,3-dihydroindol-1-ylmethylidene)-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN1C2=CC=CC=C2CC1 HLSDYWFUKOZJTE-UHFFFAOYSA-N 0.000 claims description 3
- UYOKDJNIHORDNT-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-(2-phenylethyl)-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C1N(CC=2C=CC=CC=2)C(=O)C(CCC=2C=CC=CC=2)S1 UYOKDJNIHORDNT-UHFFFAOYSA-N 0.000 claims description 3
- PZCIROBDGVLEIL-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-(furan-2-ylmethylidene)-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CC1=CC=CO1 PZCIROBDGVLEIL-UHFFFAOYSA-N 0.000 claims description 3
- ZWQHCOQRXKFJGB-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-[(4-methylpiperazin-1-yl)methylidene]-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN1CCN(C)CC1 ZWQHCOQRXKFJGB-UHFFFAOYSA-N 0.000 claims description 3
- KYXHFHACYVKHAB-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-benzylidene-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CC1=CC=CC=C1 KYXHFHACYVKHAB-UHFFFAOYSA-N 0.000 claims description 3
- FTTCNMOCBHYESC-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-phenacyl-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C1N(CC=2C=CC=CC=2)C(=O)C(CC(=O)C=2C=CC=CC=2)S1 FTTCNMOCBHYESC-UHFFFAOYSA-N 0.000 claims description 3
- 229930003427 Vitamin E Natural products 0.000 claims description 3
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 3
- 102000006255 nuclear receptors Human genes 0.000 claims description 3
- 229940088594 vitamin Drugs 0.000 claims description 3
- 229930003231 vitamin Natural products 0.000 claims description 3
- 235000013343 vitamin Nutrition 0.000 claims description 3
- 239000011782 vitamin Substances 0.000 claims description 3
- 235000019165 vitamin E Nutrition 0.000 claims description 3
- 239000011709 vitamin E Substances 0.000 claims description 3
- 229940046009 vitamin E Drugs 0.000 claims description 3
- VZGIJCXVUUINRV-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-[(n-methylanilino)methylidene]-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN(C)C1=CC=CC=C1 VZGIJCXVUUINRV-UHFFFAOYSA-N 0.000 claims description 2
- BZXKLXUWHZDDTA-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-[[benzyl(methyl)amino]methylidene]-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN(C)CC1=CC=CC=C1 BZXKLXUWHZDDTA-UHFFFAOYSA-N 0.000 claims description 2
- GMUCPXKPCHHGMW-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-[[methyl(2-phenylethyl)amino]methylidene]-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN(C)CCC1=CC=CC=C1 GMUCPXKPCHHGMW-UHFFFAOYSA-N 0.000 claims description 2
- HKFQHSDEEUNRTI-UHFFFAOYSA-N 3-[[3-benzyl-5-(2,3-dihydroindol-1-ylmethylidene)-4-oxo-1,3-thiazolidin-2-ylidene]amino]-4-(ethylamino)benzonitrile Chemical compound CCNC1=CC=C(C#N)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN1C2=CC=CC=C2CC1 HKFQHSDEEUNRTI-UHFFFAOYSA-N 0.000 claims description 2
- ZQWBBJKQQQLRBO-UHFFFAOYSA-N 3-[[3-benzyl-5-(dimethylaminomethylidene)-4-oxo-1,3-thiazolidin-2-ylidene]amino]-4-(ethylamino)benzonitrile Chemical compound CCNC1=CC=C(C#N)C=C1N=C1N(CC=2C=CC=CC=2)C(=O)C(=CN(C)C)S1 ZQWBBJKQQQLRBO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims 17
- 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 claims 14
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 12
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 10
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
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- 125000001841 imino group Chemical group [H]N=* 0.000 claims 7
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- 102000036770 Islet Amyloid Polypeptide Human genes 0.000 claims 6
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- 230000003143 atherosclerotic effect Effects 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims 6
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- DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 claims 3
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 claims 3
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- ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 claims 3
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- DNDCVAGJPBKION-DOPDSADYSA-N bombesin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1NC2=CC=CC=C2C=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CN=CN1 DNDCVAGJPBKION-DOPDSADYSA-N 0.000 claims 3
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
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- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 229940100618 rectal suppository Drugs 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CRDYSYOERSZTHZ-UHFFFAOYSA-M selenocyanate Chemical compound [Se-]C#N CRDYSYOERSZTHZ-UHFFFAOYSA-M 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 235000019613 sensory perceptions of taste Nutrition 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000008354 sodium chloride injection Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- DCQXTYAFFMSNNH-UHFFFAOYSA-M sodium;2-[bis(2-hydroxyethyl)amino]ethanol;acetate Chemical compound [Na+].CC([O-])=O.OCCN(CCO)CCO DCQXTYAFFMSNNH-UHFFFAOYSA-M 0.000 description 1
- 239000008137 solubility enhancer Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000035923 taste sensation Effects 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 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 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 108091008023 transcriptional regulators Proteins 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 229920011532 unplasticized polyvinyl chloride Polymers 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60023904P | 2004-08-10 | 2004-08-10 | |
| PCT/US2005/028357 WO2006020680A2 (en) | 2004-08-10 | 2005-08-09 | Heterocyclic compounds as pharmaceutical agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2007001539A true MX2007001539A (es) | 2007-04-23 |
Family
ID=35908114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2007001539A MX2007001539A (es) | 2004-08-10 | 2005-08-09 | Compuestos heterociclicos como agentes farmaceuticos. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7902237B2 (https=) |
| EP (1) | EP1776112A4 (https=) |
| JP (1) | JP2008509912A (https=) |
| CN (1) | CN101010078A (https=) |
| AU (1) | AU2005272916A1 (https=) |
| BR (1) | BRPI0514269A (https=) |
| CA (1) | CA2574279A1 (https=) |
| MX (1) | MX2007001539A (https=) |
| WO (1) | WO2006020680A2 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090156644A1 (en) * | 2005-07-21 | 2009-06-18 | Jacob Westman | Use of thiazole derivatives and analogues in the treatment of cancer |
| DE102007003524A1 (de) * | 2007-01-19 | 2008-09-04 | MEDICE Arzneimittel Pütter GmbH & Co. KG | Arzneimittel zur Behandlung und/oder Prävention von Arteriosklerose |
| WO2008090356A1 (en) * | 2007-01-25 | 2008-07-31 | Betagenon Ab | Thiazolidinone derivatives useful in the treatment of cancer and disorders caused by excess adiposity |
| CN101274918A (zh) * | 2007-03-30 | 2008-10-01 | 中国科学院上海药物研究所 | 一类取代五元杂环化合物,其制备方法和医学用途 |
| WO2010086613A1 (en) | 2009-01-30 | 2010-08-05 | Betagenon Ab | Compounds useful as inhibitors as ampk |
| WO2012106581A1 (en) * | 2011-02-03 | 2012-08-09 | The University Of Chicago | Fxr inhibitor, bile acid sequestrant as combination therapy for cholesterol reduction |
| NZ734451A (en) * | 2012-06-19 | 2018-12-21 | Intercept Pharmaceuticals Inc | Preparation, uses and solid forms of obeticholic acid |
| JP6556129B2 (ja) | 2013-08-01 | 2019-08-07 | アメリカ合衆国 | ファルネソイドx受容体の阻害剤及び医薬としての使用 |
| SI3043865T1 (sl) | 2013-09-11 | 2021-04-30 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Metode in farmacevtski sestavki za zdravljenje virusne okužbe s hepatitisom B |
| EP2952188A1 (en) * | 2014-06-03 | 2015-12-09 | Universität Bern | Thiazolidinones as cellular anandamide uptake inhibitors and their use in the treatment of psychiatric or neurological disorders and inflammation, in particular neuroinflammation |
| EP3148541B1 (en) | 2014-05-28 | 2020-09-02 | Universität Bern | Thiazolidinones as cellular anandamide uptake inhibitors and their use in the treatment of psychiatric or neurological disorders and inflammation, in particular neuroinflammation |
| EP3715348A1 (en) | 2015-03-26 | 2020-09-30 | Akarna Therapeutics, Ltd. | Fused bicyclic compounds for the treatment of disease |
| TW201741307A (zh) * | 2016-02-22 | 2017-12-01 | 艾洛斯生物製藥公司 | Fxr調節劑及其使用方法 |
| WO2018178260A1 (en) | 2017-03-30 | 2018-10-04 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for reducing persistence and expression of episomal viruses |
| JP2020530477A (ja) * | 2017-08-10 | 2020-10-22 | ザ テキサス エーアンドエム ユニヴァーシティ システム | Nr4a1リガンド、医薬組成物、及び関連する使用方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE523919A (https=) * | 1952-10-31 | |||
| US2719162A (en) * | 1954-03-29 | 1955-09-27 | Eastman Kodak Co | 5-(3-hydroxybenzylidene)-3-phenyl-2-phenylimino-4-thiazolidone and process |
| US3097100A (en) * | 1960-01-25 | 1963-07-09 | Eastman Kodak Co | Thiazolidones as light stabilizers for plastic compositions |
| BE608790A (fr) | 1960-10-08 | 1962-04-03 | Kalle Ag | Matériel photosensible. |
| US3314794A (en) | 1964-05-13 | 1967-04-18 | Eastman Kodak Co | Ultraviolet absorbers |
| FR1604530A (https=) * | 1967-06-06 | 1971-11-29 | ||
| US5198454A (en) * | 1991-12-03 | 1993-03-30 | Texas A&M University System | Use of OB-104 to treat ocular inflammation |
| JPH06128234A (ja) | 1992-10-19 | 1994-05-10 | Fuji Photo Film Co Ltd | 不斉炭素原子を有する化合物およびそれからなる非線形光学材料 |
| JP3871354B2 (ja) * | 1994-07-29 | 2007-01-24 | 株式会社フジモト・コーポレーション | 新規な2−(n−シアノイミノ)チアゾリジン−4−オン誘導体 |
| US6353006B1 (en) * | 1999-01-14 | 2002-03-05 | Bayer Corporation | Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents |
| ES2367539T3 (es) * | 2001-12-21 | 2011-11-04 | X-Ceptor Therapeutics, Inc. | Moduladores heterocíclicos de receptores nucleares. |
-
2005
- 2005-08-09 MX MX2007001539A patent/MX2007001539A/es not_active Application Discontinuation
- 2005-08-09 EP EP05786284A patent/EP1776112A4/en not_active Withdrawn
- 2005-08-09 BR BRPI0514269-5A patent/BRPI0514269A/pt not_active IP Right Cessation
- 2005-08-09 CA CA002574279A patent/CA2574279A1/en not_active Abandoned
- 2005-08-09 CN CNA2005800272537A patent/CN101010078A/zh active Pending
- 2005-08-09 JP JP2007525749A patent/JP2008509912A/ja active Pending
- 2005-08-09 US US11/573,614 patent/US7902237B2/en not_active Expired - Fee Related
- 2005-08-09 AU AU2005272916A patent/AU2005272916A1/en not_active Abandoned
- 2005-08-09 WO PCT/US2005/028357 patent/WO2006020680A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1776112A4 (en) | 2009-11-25 |
| WO2006020680A2 (en) | 2006-02-23 |
| BRPI0514269A (pt) | 2008-06-10 |
| US7902237B2 (en) | 2011-03-08 |
| US20080132519A1 (en) | 2008-06-05 |
| EP1776112A2 (en) | 2007-04-25 |
| CA2574279A1 (en) | 2006-02-23 |
| CN101010078A (zh) | 2007-08-01 |
| AU2005272916A1 (en) | 2006-02-23 |
| JP2008509912A (ja) | 2008-04-03 |
| WO2006020680A3 (en) | 2006-12-28 |
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