OA12960A - Substituted aralkyl derivatives. - Google Patents
Substituted aralkyl derivatives. Download PDFInfo
- Publication number
- OA12960A OA12960A OA1200500147A OA1200500147A OA12960A OA 12960 A OA12960 A OA 12960A OA 1200500147 A OA1200500147 A OA 1200500147A OA 1200500147 A OA1200500147 A OA 1200500147A OA 12960 A OA12960 A OA 12960A
- Authority
- OA
- OAPI
- Prior art keywords
- ethoxy
- phenyl
- methyl
- oxazol
- acceptable salts
- Prior art date
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- 125000003710 aryl alkyl group Chemical group 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 223
- 150000003839 salts Chemical class 0.000 claims abstract description 114
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 9
- 239000000543 intermediate Substances 0.000 claims abstract description 4
- -1 5-methyl-2-phenyl-oxazol-4-yl Chemical group 0.000 claims description 200
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 239000001294 propane Substances 0.000 claims description 33
- 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 32
- 201000010099 disease Diseases 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 25
- 125000002252 acyl group Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 22
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 21
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 102000004877 Insulin Human genes 0.000 claims description 16
- 108090001061 Insulin Proteins 0.000 claims description 16
- 229940125396 insulin Drugs 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 235000019260 propionic acid Nutrition 0.000 claims description 15
- 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 14
- 239000008103 glucose Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 12
- 208000008589 Obesity Diseases 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000004453 alkoxycarbonyl 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
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 235000020824 obesity Nutrition 0.000 claims description 12
- 229910052717 sulfur Chemical group 0.000 claims description 12
- 125000004442 acylamino group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 10
- 125000004001 thioalkyl group Chemical group 0.000 claims description 10
- 201000001320 Atherosclerosis Diseases 0.000 claims description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 9
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 9
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 9
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 229940116254 phosphonic acid Drugs 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 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
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 8
- 239000008280 blood Substances 0.000 claims description 8
- 210000004369 blood Anatomy 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 230000008569 process Effects 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
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
- 208000029078 coronary artery disease Diseases 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
- 208000011580 syndromic disease Diseases 0.000 claims description 7
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 5
- 206010048214 Xanthoma Diseases 0.000 claims description 5
- 206010048215 Xanthomatosis Diseases 0.000 claims description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 5
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 5
- 201000001421 hyperglycemia Diseases 0.000 claims description 5
- 230000001771 impaired effect Effects 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 5
- 239000000725 suspension 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
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- 206010028980 Neoplasm Diseases 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 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
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 3
- 229940123208 Biguanide Drugs 0.000 claims description 3
- 229920002911 Colestipol Polymers 0.000 claims description 3
- 208000002249 Diabetes Complications Diseases 0.000 claims description 3
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- 201000004681 Psoriasis Diseases 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229940125753 fibrate Drugs 0.000 claims description 3
- 235000021588 free fatty acids Nutrition 0.000 claims description 3
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 3
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 3
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- 239000003112 inhibitor Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- DKORSYDQYFVQNS-UHFFFAOYSA-N propyl methanesulfonate Chemical compound CCCOS(C)(=O)=O DKORSYDQYFVQNS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- HERQAPJERNZWQQ-FIWHBWSRSA-N 1-ethoxy-3-[4-[(2s)-2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]phenyl]propan-1-ol Chemical compound C1=CC(CCC(O)OCC)=CC=C1OC[C@@H](O)C1=CC=C(CC)C=N1 HERQAPJERNZWQQ-FIWHBWSRSA-N 0.000 claims description 2
- XBHQOMRKOUANQQ-UHFFFAOYSA-N 2-ethoxypropanoic acid Chemical compound CCOC(C)C(O)=O XBHQOMRKOUANQQ-UHFFFAOYSA-N 0.000 claims description 2
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- 108010064733 Angiotensins Proteins 0.000 claims description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
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- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
- 229940122199 Insulin secretagogue Drugs 0.000 claims description 2
- UDWQLQMCZMILPY-WUBHUQEYSA-N [(1S)-2-[4-(3-azido-1-ethoxypropyl)phenoxy]-1-(5-ethylpyridin-2-yl)ethoxy]-tert-butyl-dimethylsilane Chemical compound C(C)OC(CCN=[N+]=[N-])C1=CC=C(C=C1)OC[C@@H](O[Si](C)(C)C(C)(C)C)C1=NC=C(C=C1)CC UDWQLQMCZMILPY-WUBHUQEYSA-N 0.000 claims description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 2
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims description 2
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims description 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 201000009925 nephrosclerosis Diseases 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([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
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol 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)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims description 2
- 229950005143 sitosterol Drugs 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- WRKNPNNNULKIFO-UHFFFAOYSA-N 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propane-1,2-diol Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC1=CC=C(CC(O)CO)C=C1 WRKNPNNNULKIFO-UHFFFAOYSA-N 0.000 claims 1
- AEMHLIHHQUOOGP-UHFFFAOYSA-N 4-(3-aminopropyl)phenol Chemical compound NCCCC1=CC=C(O)C=C1 AEMHLIHHQUOOGP-UHFFFAOYSA-N 0.000 claims 1
- MULZWPFQTUDZPD-UHFFFAOYSA-N 5-methyl-2-phenyl-1,3-oxazole Chemical compound O1C(C)=CN=C1C1=CC=CC=C1 MULZWPFQTUDZPD-UHFFFAOYSA-N 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
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- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
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- 239000000047 product Substances 0.000 description 15
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Classifications
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- 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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- 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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- 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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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
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- 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
- C07D405/02—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 containing two hetero rings
- C07D405/04—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 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN992MU2002 | 2002-11-15 | ||
| IN792MU2003 | 2003-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA12960A true OA12960A (en) | 2006-10-13 |
Family
ID=32328188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200500147A OA12960A (en) | 2002-11-15 | 2003-11-14 | Substituted aralkyl derivatives. |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US20060142277A1 (de) |
| EP (1) | EP1569916B1 (de) |
| JP (1) | JP2006514976A (de) |
| KR (1) | KR20050075417A (de) |
| CN (1) | CN1738807A (de) |
| AP (1) | AP2005003311A0 (de) |
| AT (1) | ATE420079T1 (de) |
| AU (1) | AU2003302111A1 (de) |
| BR (1) | BR0315713A (de) |
| CA (1) | CA2506112A1 (de) |
| CO (1) | CO5700816A2 (de) |
| DE (1) | DE60325768D1 (de) |
| DK (1) | DK1569916T3 (de) |
| EA (1) | EA200500827A1 (de) |
| ES (1) | ES2319184T3 (de) |
| HR (1) | HRP20050520A2 (de) |
| MX (1) | MXPA05005063A (de) |
| NO (1) | NO20052413L (de) |
| NZ (1) | NZ540474A (de) |
| OA (1) | OA12960A (de) |
| RS (1) | RS20050426A (de) |
| WO (1) | WO2004046119A1 (de) |
| ZA (1) | ZA200503828B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| SG188642A1 (en) | 2010-09-24 | 2013-05-31 | Ranbaxy Lab Ltd | Matrix metalloproteinase inhibitors |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE60211891T2 (de) * | 2001-05-15 | 2007-05-24 | F. Hoffmann-La Roche Ag | Carbonsäure-substituierte oxazol-derivate zur verwendung als ppar-alpha und -gamma aktivatoren zur behandlung von diabetes |
| ES2316736T3 (es) * | 2002-02-25 | 2009-04-16 | Eli Lilly And Company | Moduladores de receptores activados por proliferador de peroxisoma. |
| WO2004004665A2 (en) * | 2002-07-09 | 2004-01-15 | Bristol-Myers Squibb Company | Substituted heterocyclic derivatives useful as antidiabetic and antiobesity agents and method |
| AR041481A1 (es) * | 2002-10-07 | 2005-05-18 | Hoffmann La Roche | Derivados de acido arilpropionico-oxazol y su uso como agonistas de ppar |
-
2003
- 2003-11-14 KR KR1020057008753A patent/KR20050075417A/ko not_active Ceased
- 2003-11-14 RS YUP-2005/0426A patent/RS20050426A/sr unknown
- 2003-11-14 US US10/534,726 patent/US20060142277A1/en not_active Abandoned
- 2003-11-14 NZ NZ540474A patent/NZ540474A/en not_active IP Right Cessation
- 2003-11-14 CA CA002506112A patent/CA2506112A1/en not_active Abandoned
- 2003-11-14 AU AU2003302111A patent/AU2003302111A1/en not_active Abandoned
- 2003-11-14 AT AT03808341T patent/ATE420079T1/de active
- 2003-11-14 DE DE60325768T patent/DE60325768D1/de not_active Expired - Lifetime
- 2003-11-14 OA OA1200500147A patent/OA12960A/en unknown
- 2003-11-14 AP AP2005003311A patent/AP2005003311A0/xx unknown
- 2003-11-14 DK DK03808341T patent/DK1569916T3/da active
- 2003-11-14 JP JP2004570329A patent/JP2006514976A/ja active Pending
- 2003-11-14 ES ES03808341T patent/ES2319184T3/es not_active Expired - Lifetime
- 2003-11-14 MX MXPA05005063A patent/MXPA05005063A/es active IP Right Grant
- 2003-11-14 BR BR0315713-0A patent/BR0315713A/pt not_active Application Discontinuation
- 2003-11-14 WO PCT/IN2003/000358 patent/WO2004046119A1/en not_active Ceased
- 2003-11-14 EP EP03808341A patent/EP1569916B1/de not_active Expired - Lifetime
- 2003-11-14 EA EA200500827A patent/EA200500827A1/ru unknown
- 2003-11-14 HR HR20050520A patent/HRP20050520A2/hr not_active Application Discontinuation
- 2003-11-14 CN CNA2003801088363A patent/CN1738807A/zh active Pending
-
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
-
2009
- 2009-07-08 US US12/458,315 patent/US20090275565A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1569916A1 (de) | 2005-09-07 |
| ATE420079T1 (de) | 2009-01-15 |
| NZ540474A (en) | 2008-04-30 |
| US20090275565A1 (en) | 2009-11-05 |
| AP2005003311A0 (en) | 2005-06-30 |
| WO2004046119A1 (en) | 2004-06-03 |
| EA200500827A1 (ru) | 2005-12-29 |
| NO20052413L (no) | 2005-07-26 |
| HRP20050520A2 (en) | 2005-10-31 |
| JP2006514976A (ja) | 2006-05-18 |
| ZA200503828B (en) | 2006-11-29 |
| RS20050426A (sr) | 2008-04-04 |
| US20060142277A1 (en) | 2006-06-29 |
| ES2319184T3 (es) | 2009-05-05 |
| AU2003302111A1 (en) | 2004-06-15 |
| DK1569916T3 (da) | 2009-04-06 |
| DE60325768D1 (de) | 2009-02-26 |
| BR0315713A (pt) | 2005-09-13 |
| EP1569916B1 (de) | 2009-01-07 |
| MXPA05005063A (es) | 2005-08-16 |
| CN1738807A (zh) | 2006-02-22 |
| KR20050075417A (ko) | 2005-07-20 |
| NO20052413D0 (no) | 2005-05-13 |
| CO5700816A2 (es) | 2006-11-30 |
| CA2506112A1 (en) | 2004-06-03 |
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