NZ531917A - Linked biaryl compounds - Google Patents
Linked biaryl compoundsInfo
- Publication number
- NZ531917A NZ531917A NZ531917A NZ53191702A NZ531917A NZ 531917 A NZ531917 A NZ 531917A NZ 531917 A NZ531917 A NZ 531917A NZ 53191702 A NZ53191702 A NZ 53191702A NZ 531917 A NZ531917 A NZ 531917A
- Authority
- NZ
- New Zealand
- Prior art keywords
- group
- alkyl
- aryl
- compound
- hydrogen
- Prior art date
Links
- -1 biaryl compounds Chemical class 0.000 title claims abstract description 116
- 150000001875 compounds Chemical class 0.000 claims abstract description 283
- 238000000034 method Methods 0.000 claims abstract description 68
- 239000000203 mixture Substances 0.000 claims abstract description 67
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 21
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 6
- 201000011510 cancer Diseases 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims description 235
- 125000000217 alkyl group Chemical group 0.000 claims description 227
- 229910052739 hydrogen Inorganic materials 0.000 claims description 116
- 239000001257 hydrogen Substances 0.000 claims description 116
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 96
- 229910052760 oxygen Inorganic materials 0.000 claims description 84
- 229910052717 sulfur Inorganic materials 0.000 claims description 77
- 229910052757 nitrogen Inorganic materials 0.000 claims description 70
- 201000010099 disease Diseases 0.000 claims description 67
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 66
- 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 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 229940002612 prodrug Drugs 0.000 claims description 31
- 239000000651 prodrug Substances 0.000 claims description 31
- 210000004027 cell Anatomy 0.000 claims description 30
- 208000035475 disorder Diseases 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 25
- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 22
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 230000001404 mediated effect Effects 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 15
- 230000004968 inflammatory condition Effects 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 230000001613 neoplastic effect Effects 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 206010012601 diabetes mellitus Diseases 0.000 claims description 13
- 230000003247 decreasing effect Effects 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 12
- 208000008589 Obesity Diseases 0.000 claims description 11
- 235000020824 obesity Nutrition 0.000 claims description 11
- 201000001320 Atherosclerosis Diseases 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 230000035939 shock Effects 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- 238000008214 LDL Cholesterol Methods 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052786 argon Inorganic materials 0.000 claims description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052727 yttrium Inorganic materials 0.000 claims description 8
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 239000000556 agonist Substances 0.000 claims description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 208000011580 syndromic disease Diseases 0.000 claims description 7
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 208000015114 central nervous system disease Diseases 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 230000005176 gastrointestinal motility Effects 0.000 claims description 6
- 208000026278 immune system disease Diseases 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000005493 quinolyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 206010022489 Insulin Resistance Diseases 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 4
- 208000030814 Eating disease Diseases 0.000 claims description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 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 description 4
- 235000014632 disordered eating Nutrition 0.000 claims description 4
- 230000003028 elevating effect Effects 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 229940125708 antidiabetic agent Drugs 0.000 claims description 3
- 239000003472 antidiabetic agent Substances 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 230000036772 blood pressure Effects 0.000 claims description 3
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 3
- 201000008980 hyperinsulinism Diseases 0.000 claims description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 206010038389 Renal cancer Diseases 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 239000003529 anticholesteremic agent Substances 0.000 claims description 2
- 229940127226 anticholesterol agent Drugs 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 238000001794 hormone therapy Methods 0.000 claims description 2
- 210000005260 human cell Anatomy 0.000 claims description 2
- 201000001421 hyperglycemia Diseases 0.000 claims description 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 2
- 208000008384 ileus Diseases 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 201000010982 kidney cancer Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 230000036303 septic shock Effects 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 claims 1
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 230000014509 gene expression Effects 0.000 abstract description 25
- 108090000623 proteins and genes Proteins 0.000 abstract description 9
- 102000004169 proteins and genes Human genes 0.000 abstract description 6
- 206010061218 Inflammation Diseases 0.000 abstract description 3
- 208000027866 inflammatory disease Diseases 0.000 abstract description 3
- 230000004054 inflammatory process Effects 0.000 abstract description 3
- 230000037356 lipid metabolism Effects 0.000 abstract description 3
- 230000004663 cell proliferation Effects 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
- 238000005481 NMR spectroscopy Methods 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 43
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 42
- 102000011779 Nitric Oxide Synthase Type II Human genes 0.000 description 41
- 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 37
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 36
- 102000003390 tumor necrosis factor Human genes 0.000 description 36
- 230000000694 effects Effects 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 125000001424 substituent group Chemical group 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 108010010234 HDL Lipoproteins Proteins 0.000 description 20
- 102000015779 HDL Lipoproteins Human genes 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
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- 239000007858 starting material Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 17
- 235000012000 cholesterol Nutrition 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 15
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
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- 101150041968 CDC13 gene Proteins 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000499 gel Substances 0.000 description 12
- 125000004404 heteroalkyl group Chemical group 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 208000024891 symptom Diseases 0.000 description 12
- XPRGFWCOARUGAL-UHFFFAOYSA-N 3-anilino-1-phenylpyrrolidine-2,5-dione Chemical compound O=C1N(C=2C=CC=CC=2)C(=O)CC1NC1=CC=CC=C1 XPRGFWCOARUGAL-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000012190 activator Substances 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 10
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- NTSKOZMSQFZPKG-ZENAZSQFSA-N (3s)-3-amino-4-(2-diphenoxyphosphorylpyrrolidin-1-yl)-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](N)C(=O)N1CCCC1P(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 NTSKOZMSQFZPKG-ZENAZSQFSA-N 0.000 description 5
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- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- OKHUDYOUNFDWEI-BGERDNNASA-N (2s)-2-amino-1-(2-diphenoxyphosphorylpyrrolidin-1-yl)-3-(1h-imidazol-5-yl)propan-1-one Chemical compound C([C@H](N)C(=O)N1C(CCC1)P(=O)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)C1=CN=CN1 OKHUDYOUNFDWEI-BGERDNNASA-N 0.000 description 4
- BLSRGJPGRJBHQK-BUSXIPJBSA-N (2s)-2-amino-1-(2-diphenoxyphosphorylpyrrolidin-1-yl)propan-1-one Chemical compound C[C@H](N)C(=O)N1CCCC1P(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 BLSRGJPGRJBHQK-BUSXIPJBSA-N 0.000 description 4
- JMVFRBIAXHMBPB-KKFHFHRHSA-N (3s)-3-amino-4-(2-diphenoxyphosphorylpyrrolidin-1-yl)-4-oxobutanamide Chemical compound NC(=O)C[C@H](N)C(=O)N1CCCC1P(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 JMVFRBIAXHMBPB-KKFHFHRHSA-N 0.000 description 4
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| US38683302P | 2002-06-06 | 2002-06-06 | |
| PCT/US2002/029232 WO2003024395A2 (en) | 2001-09-14 | 2002-09-13 | Linked biaryl compounds |
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| US20040229781A1 (en) * | 2000-05-10 | 2004-11-18 | Marks Andrew Robert | Compounds and methods for treating and preventing exercise-induced cardiac arrhythmias |
| US7718644B2 (en) * | 2004-01-22 | 2010-05-18 | The Trustees Of Columbia University In The City Of New York | Anti-arrhythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2) and uses thereof |
| US20060293266A1 (en) * | 2000-05-10 | 2006-12-28 | The Trustees Of Columbia | Phosphodiesterase 4D in the ryanodine receptor complex protects against heart failure |
| US7393652B2 (en) * | 2000-05-10 | 2008-07-01 | The Trustees Of Columbia University In The City Of New York | Methods for identifying a chemical compound that directly enhances binding of FKBP12.6 to PKA-phosphorylated type 2 ryanodine receptor (RyR2) |
| US20040048780A1 (en) * | 2000-05-10 | 2004-03-11 | The Trustees Of Columbia University In The City Of New York | Method for treating and preventing cardiac arrhythmia |
| US8022058B2 (en) | 2000-05-10 | 2011-09-20 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the RyR receptors |
| US6489125B1 (en) * | 2000-05-10 | 2002-12-03 | The Trustees Of Columbia University In The City Of New York | Methods for identifying chemical compounds that inhibit dissociation of FKBP12.6 binding protein from type 2 ryanodine receptor |
| US7879840B2 (en) * | 2005-08-25 | 2011-02-01 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the RyR receptors |
| ES2443642T3 (es) | 2001-09-14 | 2014-02-20 | Amgen Inc. | Compuestos de biarilo conectados |
| US6833380B2 (en) | 2002-03-07 | 2004-12-21 | Warner-Lambert Company, Llc | Compounds that modulate PPAR activity and methods of preparation |
| US7794965B2 (en) | 2002-03-13 | 2010-09-14 | Signum Biosciences, Inc. | Method of identifying modulators of PP2A methylase |
| US6875780B2 (en) | 2002-04-05 | 2005-04-05 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods for their preparation |
| US7544678B2 (en) * | 2002-11-05 | 2009-06-09 | The Trustees Of Columbia University In The City Of New York | Anti-arrythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2) |
| WO2004080283A2 (en) | 2003-03-07 | 2004-09-23 | The Trustees Of Columbia University, In The City Of New York | Type 1 ryanodine receptor-based methods |
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| US7244763B2 (en) | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
| WO2005012221A1 (ja) * | 2003-08-04 | 2005-02-10 | Ono Pharmaceutical Co., Ltd. | ジフェニルエーテル化合物、その製造方法および用途 |
| US8710045B2 (en) * | 2004-01-22 | 2014-04-29 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the ryanodine receptors |
| EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
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| WO2005105736A1 (en) * | 2004-05-05 | 2005-11-10 | Novo Nordisk A/S | Novel compounds, their preparation and use |
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| EP1650183A1 (en) * | 2004-10-21 | 2006-04-26 | Cellzome Ag | (Benzyloxy-biphenyl) acetic acids and derivatives thereof and their use in therapy |
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| US20060135540A1 (en) * | 2004-11-30 | 2006-06-22 | Jack Lin | PPAR active compounds |
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| US8221804B2 (en) * | 2005-02-03 | 2012-07-17 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| DE102005020229A1 (de) * | 2005-04-30 | 2006-11-09 | Bayer Healthcare Ag | Verwendung von Indolin-Phenylsulfonamid-Derivaten |
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2002
- 2002-09-13 ES ES02773386.4T patent/ES2443642T3/es not_active Expired - Lifetime
- 2002-09-13 WO PCT/US2002/029232 patent/WO2003024395A2/en not_active Ceased
- 2002-09-13 BR BR0212512-9A patent/BR0212512A/pt not_active IP Right Cessation
- 2002-09-13 EP EP02773386.4A patent/EP1435946B8/en not_active Expired - Lifetime
- 2002-09-13 CA CA2460313A patent/CA2460313C/en not_active Expired - Fee Related
- 2002-09-13 JP JP2003528493A patent/JP4269052B2/ja not_active Expired - Fee Related
- 2002-09-13 AU AU2002336532A patent/AU2002336532C1/en not_active Ceased
- 2002-09-13 IL IL16084502A patent/IL160845A0/xx unknown
- 2002-09-13 US US10/244,063 patent/US6869975B2/en not_active Expired - Fee Related
- 2002-09-13 CN CNA028223241A patent/CN1585638A/zh active Pending
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- 2002-09-13 NZ NZ531917A patent/NZ531917A/en unknown
- 2002-09-13 KR KR10-2004-7003851A patent/KR20040063897A/ko not_active Withdrawn
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2004
- 2004-08-20 US US10/939,918 patent/US7645779B2/en not_active Expired - Fee Related
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| WO2003024395A8 (en) | 2004-01-22 |
| AU2002336532B2 (en) | 2007-10-18 |
| ES2443642T3 (es) | 2014-02-20 |
| CA2460313A1 (en) | 2003-03-27 |
| JP4269052B2 (ja) | 2009-05-27 |
| CA2460313C (en) | 2011-03-08 |
| US20080161351A1 (en) | 2008-07-03 |
| US7645779B2 (en) | 2010-01-12 |
| BR0212512A (pt) | 2004-10-26 |
| JP2005508318A (ja) | 2005-03-31 |
| US20030149108A1 (en) | 2003-08-07 |
| US6869975B2 (en) | 2005-03-22 |
| EP1435946B8 (en) | 2013-12-18 |
| IL160845A0 (en) | 2004-08-31 |
| WO2003024395A3 (en) | 2003-12-11 |
| EP1435946B1 (en) | 2013-11-06 |
| CN1585638A (zh) | 2005-02-23 |
| EP1435946A2 (en) | 2004-07-14 |
| EP1435946A4 (en) | 2006-02-01 |
| AU2002336532C1 (en) | 2008-10-16 |
| WO2003024395A2 (en) | 2003-03-27 |
| MXPA04002330A (es) | 2005-04-08 |
| KR20040063897A (ko) | 2004-07-14 |
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