HRP20050520A2 - Substituted aralkyl derivatives - Google Patents
Substituted aralkyl derivatives Download PDFInfo
- Publication number
- HRP20050520A2 HRP20050520A2 HR20050520A HRP20050520A HRP20050520A2 HR P20050520 A2 HRP20050520 A2 HR P20050520A2 HR 20050520 A HR20050520 A HR 20050520A HR P20050520 A HRP20050520 A HR P20050520A HR P20050520 A2 HRP20050520 A2 HR P20050520A2
- Authority
- HR
- Croatia
- Prior art keywords
- ethoxy
- phenyl
- methyl
- oxazol
- pharmaceutically acceptable
- Prior art date
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- 125000003710 aryl alkyl group Chemical group 0.000 title claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 242
- -1 nitro, amino Chemical group 0.000 claims description 187
- 150000003839 salts Chemical class 0.000 claims description 144
- 238000002360 preparation method Methods 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 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 34
- 239000001294 propane Substances 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- 239000000243 solution Substances 0.000 claims description 26
- 125000002252 acyl group Chemical group 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 21
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 206010012601 diabetes mellitus Diseases 0.000 claims description 14
- 201000001320 Atherosclerosis Diseases 0.000 claims description 13
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 13
- 208000008589 Obesity Diseases 0.000 claims description 13
- 235000012000 cholesterol Nutrition 0.000 claims description 13
- 235000020824 obesity Nutrition 0.000 claims description 13
- 206010022489 Insulin Resistance Diseases 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 12
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 12
- 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 description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 10
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 239000008103 glucose Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000033 alkoxyamino group Chemical class 0.000 claims description 9
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 9
- 125000004949 alkyl amino carbonyl amino group Chemical class 0.000 claims description 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 9
- 125000006598 aminocarbonylamino group Chemical class 0.000 claims description 9
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 9
- 208000029078 coronary artery disease Diseases 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000004001 thioalkyl group Chemical group 0.000 claims description 9
- 150000003626 triacylglycerols Chemical class 0.000 claims description 9
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
- 239000005711 Benzoic acid Substances 0.000 claims description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 7
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 7
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 7
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 102000004877 Insulin Human genes 0.000 claims description 6
- 108090001061 Insulin Proteins 0.000 claims description 6
- 102000016267 Leptin Human genes 0.000 claims description 6
- 108010092277 Leptin Proteins 0.000 claims description 6
- 108010069201 VLDL Cholesterol Proteins 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 6
- 201000001421 hyperglycemia Diseases 0.000 claims description 6
- 229940125396 insulin Drugs 0.000 claims description 6
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims description 6
- 229940039781 leptin Drugs 0.000 claims description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 5
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 206010048214 Xanthoma Diseases 0.000 claims description 5
- 206010048215 Xanthomatosis Diseases 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 5
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 5
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 5
- 239000003826 tablet Substances 0.000 claims description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 5
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 4
- 229920001268 Cholestyramine Polymers 0.000 claims description 4
- 229920002911 Colestipol Polymers 0.000 claims description 4
- 229940100389 Sulfonylurea Drugs 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 claims description 4
- 229960002604 colestipol Drugs 0.000 claims description 4
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- NLMQYQCYJUZTMM-IBGZPJMESA-N ethyl (2s)-2-ethoxy-3-[4-[(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)methoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OCC1=C(C)OC(C=2SC=CC=2)=N1 NLMQYQCYJUZTMM-IBGZPJMESA-N 0.000 claims description 4
- 229940125753 fibrate Drugs 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 229960003512 nicotinic acid Drugs 0.000 claims description 4
- 235000001968 nicotinic acid Nutrition 0.000 claims description 4
- 239000011664 nicotinic acid Substances 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 claims description 4
- 229960003912 probucol Drugs 0.000 claims description 4
- 239000006188 syrup Substances 0.000 claims description 4
- 235000020357 syrup Nutrition 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- XVMBSQQFBULZPM-KRWDZBQOSA-N (2s)-2-ethoxy-3-[4-[(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)methoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2SC=CC=2)=N1 XVMBSQQFBULZPM-KRWDZBQOSA-N 0.000 claims description 3
- HLGYDDWOYHRIAA-UHFFFAOYSA-N 2-ethoxy-1-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]pentan-3-ol Chemical compound C1=CC(CC(OCC)C(O)CC)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 HLGYDDWOYHRIAA-UHFFFAOYSA-N 0.000 claims description 3
- RMSKTGVBTVWTGU-UHFFFAOYSA-N 4-[2-[4-(2,3-diethoxypentyl)phenoxy]ethyl]-5-methyl-2-phenyl-1,3-oxazole Chemical compound C1=CC(CC(C(CC)OCC)OCC)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 RMSKTGVBTVWTGU-UHFFFAOYSA-N 0.000 claims description 3
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
- 206010068871 Myotonic dystrophy Diseases 0.000 claims description 3
- 206010029164 Nephrotic syndrome Diseases 0.000 claims description 3
- 208000001132 Osteoporosis Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 3
- AAHDAJBOYAEUPB-FQEVSTJZSA-N ethyl (2s)-2-ethoxy-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OCCC1=C(C)OC(C=2SC=CC=2)=N1 AAHDAJBOYAEUPB-FQEVSTJZSA-N 0.000 claims description 3
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 208000017169 kidney disease Diseases 0.000 claims description 3
- 201000009925 nephrosclerosis Diseases 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- YAFGCSYTSTZGJB-FIWHBWSRSA-N (1S)-2-[4-(3-azido-1-ethoxypropyl)phenoxy]-1-(5-ethylpyridin-2-yl)ethanol Chemical compound C(C)OC(CCN=[N+]=[N-])C1=CC=C(C=C1)OC[C@@H](O)C1=NC=C(C=C1)CC YAFGCSYTSTZGJB-FIWHBWSRSA-N 0.000 claims description 2
- VINHIPNMEJPKBW-AIBWNMTMSA-N (2s)-1-ethoxy-3-[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]propane-1,2-diol Chemical compound C1=CC(C[C@H](O)C(O)OCC)=CC=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 VINHIPNMEJPKBW-AIBWNMTMSA-N 0.000 claims description 2
- QRLTVIRGBXGSLD-QHCPKHFHSA-N (2s)-2-ethoxy-3-[4-[(5-methyl-2-quinolin-2-yl-1,3-oxazol-4-yl)methoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2N=C3C=CC=CC3=CC=2)=N1 QRLTVIRGBXGSLD-QHCPKHFHSA-N 0.000 claims description 2
- NQPYHPFPNFPOHN-SFHVURJKSA-N (2s)-2-ethoxy-3-[4-[(5-methyl-2-thiophen-3-yl-1,3-oxazol-4-yl)methoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C2=CSC=C2)=N1 NQPYHPFPNFPOHN-SFHVURJKSA-N 0.000 claims description 2
- UPCKXAMFODQFIE-DEOSSOPVSA-N (2s)-2-ethoxy-3-[4-[2-(5-methyl-2-quinolin-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=C(C)OC(C=2N=C3C=CC=CC3=CC=2)=N1 UPCKXAMFODQFIE-DEOSSOPVSA-N 0.000 claims description 2
- MDURWMBTDAVDFG-SFHVURJKSA-N (2s)-2-ethoxy-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=C(C)OC(C=2SC=CC=2)=N1 MDURWMBTDAVDFG-SFHVURJKSA-N 0.000 claims description 2
- PGBLXKBJIYYRGZ-IBGZPJMESA-N (2s)-2-ethoxy-3-[4-[2-(5-methyl-2-thiophen-3-yl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=C(C)OC(C2=CSC=C2)=N1 PGBLXKBJIYYRGZ-IBGZPJMESA-N 0.000 claims description 2
- KVAZNMYEMLWKKC-IBGZPJMESA-N (2s)-2-ethoxy-3-[4-[2-[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=C(C)OC(C=2OC=CC=2)=N1 KVAZNMYEMLWKKC-IBGZPJMESA-N 0.000 claims description 2
- QCHCMMQOWAXIGU-IBGZPJMESA-N (2s)-2-ethoxy-3-[4-[2-[5-methyl-2-(3-methylthiophen-2-yl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=C(C)OC(C2=C(C=CS2)C)=N1 QCHCMMQOWAXIGU-IBGZPJMESA-N 0.000 claims description 2
- XIUNCPMQIKCDEO-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[2-[5-methyl-2-(5-methylfuran-2-yl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=C(C)OC(C=2OC(C)=CC=2)=N1 XIUNCPMQIKCDEO-FQEVSTJZSA-N 0.000 claims description 2
- KACYCSASEXQENA-IBGZPJMESA-N (2s)-2-ethoxy-3-[4-[2-[5-methyl-2-(5-methylthiophen-2-yl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=C(C)OC(C=2SC(C)=CC=2)=N1 KACYCSASEXQENA-IBGZPJMESA-N 0.000 claims description 2
- QFQGNTDOAIPHRN-QHCPKHFHSA-N (2s)-2-ethoxy-3-[4-[2-[5-methyl-2-(5-phenylthiophen-2-yl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=C(C)OC(C=2SC(=CC=2)C=2C=CC=CC=2)=N1 QFQGNTDOAIPHRN-QHCPKHFHSA-N 0.000 claims description 2
- MEEMHWURVJJSRR-IBGZPJMESA-N (2s)-2-ethoxy-3-[4-[3-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)propoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCCC1=C(C)OC(C=2SC=CC=2)=N1 MEEMHWURVJJSRR-IBGZPJMESA-N 0.000 claims description 2
- QXHMQAXQVOOCLD-SFHVURJKSA-N (2s)-2-ethoxy-3-[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2OC=CC=2)=N1 QXHMQAXQVOOCLD-SFHVURJKSA-N 0.000 claims description 2
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- USFSWIKTCWPTJP-NRFANRHFSA-N ethyl (2s)-2-ethoxy-3-[4-[(5-methyl-2-pyridin-4-yl-1,3-oxazol-4-yl)methoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OCC1=C(C)OC(C=2C=CN=CC=2)=N1 USFSWIKTCWPTJP-NRFANRHFSA-N 0.000 claims 1
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- 229960000281 trometamol Drugs 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- 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
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- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- 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
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- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
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- C07D215/14—Radicals substituted by oxygen atoms
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
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- C07D265/38—[b, e]-condensed with two six-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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Landscapes
- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Cardiology (AREA)
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- Obesity (AREA)
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- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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IN992MU2002 | 2002-11-15 | ||
IN792MU2003 | 2003-08-12 | ||
PCT/IN2003/000358 WO2004046119A1 (en) | 2002-11-15 | 2003-11-14 | Substituted aralkyl derivatives |
Publications (1)
Publication Number | Publication Date |
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HRP20050520A2 true HRP20050520A2 (en) | 2005-10-31 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HR20050520A HRP20050520A2 (en) | 2002-11-15 | 2005-06-09 | Substituted aralkyl derivatives |
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US (2) | US20060142277A1 (es) |
EP (1) | EP1569916B1 (es) |
JP (1) | JP2006514976A (es) |
KR (1) | KR20050075417A (es) |
CN (1) | CN1738807A (es) |
AP (1) | AP2005003311A0 (es) |
AT (1) | ATE420079T1 (es) |
AU (1) | AU2003302111A1 (es) |
BR (1) | BR0315713A (es) |
CA (1) | CA2506112A1 (es) |
CO (1) | CO5700816A2 (es) |
DE (1) | DE60325768D1 (es) |
DK (1) | DK1569916T3 (es) |
EA (1) | EA200500827A1 (es) |
ES (1) | ES2319184T3 (es) |
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NO (1) | NO20052413L (es) |
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OA (1) | OA12960A (es) |
RS (1) | RS20050426A (es) |
WO (1) | WO2004046119A1 (es) |
ZA (1) | ZA200503828B (es) |
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TW200724138A (en) | 2005-03-29 | 2007-07-01 | Sk Corp | Substituted carboxylic acid derivatives for the treatment of diabetes and lipid disorders, their preparation and use |
KR20130140688A (ko) | 2010-09-24 | 2013-12-24 | 랜박시 래보러터리스 리미티드 | 기질 메탈로프로테나제 저해제 |
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JPS51149265A (en) * | 1975-06-13 | 1976-12-22 | Yoshitomi Pharmaceut Ind Ltd | Process for preparing phenoxyaminopropanol derivatives |
US5089514A (en) * | 1990-06-14 | 1992-02-18 | Pfizer Inc. | 3-coxazolyl [phenyl, chromanyl or benzofuranyl]-2-hydroxypropionic acid derivatives and analogs as hypoglycemic agents |
NZ239846A (en) * | 1990-09-27 | 1994-11-25 | Merck & Co Inc | Sulphonamide derivatives and pharmaceutical compositions thereof |
JPH08325263A (ja) * | 1995-05-31 | 1996-12-10 | Sumitomo Metal Ind Ltd | 新規2−アミノ−3−フェニルプロピオン酸誘導体 |
EE03765B1 (et) * | 1996-08-19 | 2002-06-17 | Japan Tobacco Inc. | Propioonhappe derivaadid ja nende kasutamine |
JPH11158144A (ja) * | 1997-09-19 | 1999-06-15 | Ss Pharmaceut Co Ltd | α−置換フェニルプロピオン酸誘導体及びこれを含有する医薬 |
TW574193B (en) * | 1999-12-03 | 2004-02-01 | Astrazeneca Ab | Novel phenalkyloxy-phenyl derivatives, pharmaceutical composition containing the same and their uses |
ES2264482T3 (es) * | 2001-05-15 | 2007-01-01 | F. Hoffmann-La Roche Ag | Derivados de oxazol sustituidos por acido carboxilico para uso como activadores de ppar-alfa y gamma en el tratamiento de diabetes. |
ES2316736T3 (es) * | 2002-02-25 | 2009-04-16 | Eli Lilly And Company | Moduladores de receptores activados por proliferador de peroxisoma. |
JP4579681B2 (ja) * | 2002-07-09 | 2010-11-10 | ブリストル−マイヤーズ スクイブ カンパニー | 抗糖尿病薬および抗肥満薬として有用な置換ヘテロシクロ誘導体および方法 |
AR041481A1 (es) * | 2002-10-07 | 2005-05-18 | Hoffmann La Roche | Derivados de acido arilpropionico-oxazol y su uso como agonistas de ppar |
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- 2003-11-14 AT AT03808341T patent/ATE420079T1/de active
- 2003-11-14 JP JP2004570329A patent/JP2006514976A/ja active Pending
- 2003-11-14 AU AU2003302111A patent/AU2003302111A1/en not_active Abandoned
- 2003-11-14 AP AP2005003311A patent/AP2005003311A0/xx unknown
- 2003-11-14 WO PCT/IN2003/000358 patent/WO2004046119A1/en active Application Filing
- 2003-11-14 DK DK03808341T patent/DK1569916T3/da active
- 2003-11-14 KR KR1020057008753A patent/KR20050075417A/ko not_active Application Discontinuation
- 2003-11-14 NZ NZ540474A patent/NZ540474A/en not_active IP Right Cessation
-
2005
- 2005-05-12 ZA ZA200503828A patent/ZA200503828B/en unknown
- 2005-05-13 NO NO20052413A patent/NO20052413L/no not_active Application Discontinuation
- 2005-05-16 CO CO05046639A patent/CO5700816A2/es not_active Application Discontinuation
- 2005-06-09 HR HR20050520A patent/HRP20050520A2/hr not_active Application Discontinuation
-
2009
- 2009-07-08 US US12/458,315 patent/US20090275565A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
CA2506112A1 (en) | 2004-06-03 |
US20090275565A1 (en) | 2009-11-05 |
AP2005003311A0 (en) | 2005-06-30 |
NZ540474A (en) | 2008-04-30 |
DE60325768D1 (de) | 2009-02-26 |
NO20052413L (no) | 2005-07-26 |
NO20052413D0 (no) | 2005-05-13 |
OA12960A (en) | 2006-10-13 |
ZA200503828B (en) | 2006-11-29 |
EA200500827A1 (ru) | 2005-12-29 |
CN1738807A (zh) | 2006-02-22 |
RS20050426A (en) | 2008-04-04 |
WO2004046119A1 (en) | 2004-06-03 |
ES2319184T3 (es) | 2009-05-05 |
US20060142277A1 (en) | 2006-06-29 |
JP2006514976A (ja) | 2006-05-18 |
KR20050075417A (ko) | 2005-07-20 |
EP1569916B1 (en) | 2009-01-07 |
AU2003302111A1 (en) | 2004-06-15 |
MXPA05005063A (es) | 2005-08-16 |
BR0315713A (pt) | 2005-09-13 |
EP1569916A1 (en) | 2005-09-07 |
CO5700816A2 (es) | 2006-11-30 |
DK1569916T3 (da) | 2009-04-06 |
ATE420079T1 (de) | 2009-01-15 |
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