DE60319084T2 - Ortho-substituierte benzoesäurederivate zur behandlung von insulinresistenz - Google Patents
Ortho-substituierte benzoesäurederivate zur behandlung von insulinresistenz Download PDFInfo
- Publication number
- DE60319084T2 DE60319084T2 DE60319084T DE60319084T DE60319084T2 DE 60319084 T2 DE60319084 T2 DE 60319084T2 DE 60319084 T DE60319084 T DE 60319084T DE 60319084 T DE60319084 T DE 60319084T DE 60319084 T2 DE60319084 T2 DE 60319084T2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- amino
- benzoic acid
- phenoxy
- oxopropyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000011282 treatment Methods 0.000 title claims description 26
- 208000001072 type 2 diabetes mellitus Diseases 0.000 title claims description 19
- 206010022489 Insulin Resistance Diseases 0.000 title claims description 11
- 150000001558 benzoic acid derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 124
- 150000003839 salts Chemical class 0.000 claims description 70
- -1 2 - [(4- {3- [ethyl (2-fluorobenzyl) amino] -2-oxopropyl} phenoxy) methyl] benzoic acid Chemical compound 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 239000005711 Benzoic acid Substances 0.000 claims description 9
- 235000010233 benzoic acid Nutrition 0.000 claims description 9
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 7
- RBCHSXQOPLPDHL-UHFFFAOYSA-N 2-[[4-[2-[ethyl-[(2-fluorophenyl)methyl]amino]-2-oxoethyl]phenoxy]methyl]benzoic acid Chemical compound C=1C=C(OCC=2C(=CC=CC=2)C(O)=O)C=CC=1CC(=O)N(CC)CC1=CC=CC=C1F RBCHSXQOPLPDHL-UHFFFAOYSA-N 0.000 claims description 6
- CKPOVXTWCZIWNQ-UHFFFAOYSA-N 2-[[4-[3-[(2,4-difluorophenyl)methyl-propylamino]-3-oxopropyl]phenoxy]methyl]benzoic acid Chemical compound C=1C=C(OCC=2C(=CC=CC=2)C(O)=O)C=CC=1CCC(=O)N(CCC)CC1=CC=C(F)C=C1F CKPOVXTWCZIWNQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002528 4-isopropyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 5
- AVLMOQWYTWOYRH-UHFFFAOYSA-N 2-[[4-[2-[(2,4-difluorophenyl)methyl-heptylamino]-2-oxoethyl]phenoxy]methyl]benzoic acid Chemical compound C=1C=C(OCC=2C(=CC=CC=2)C(O)=O)C=CC=1CC(=O)N(CCCCCCC)CC1=CC=C(F)C=C1F AVLMOQWYTWOYRH-UHFFFAOYSA-N 0.000 claims description 5
- GGXHKHVHQONVSY-UHFFFAOYSA-N 2-[[4-[2-[(2,4-difluorophenyl)methyl-heptylamino]-2-oxoethyl]phenyl]sulfanylmethyl]benzoic acid Chemical compound C=1C=C(SCC=2C(=CC=CC=2)C(O)=O)C=CC=1CC(=O)N(CCCCCCC)CC1=CC=C(F)C=C1F GGXHKHVHQONVSY-UHFFFAOYSA-N 0.000 claims description 5
- ODDKTPKGWSSZGR-UHFFFAOYSA-N 2-[[4-[2-[benzyl(hexyl)amino]-2-oxoethyl]phenoxy]methyl]benzoic acid Chemical compound C=1C=C(OCC=2C(=CC=CC=2)C(O)=O)C=CC=1CC(=O)N(CCCCCC)CC1=CC=CC=C1 ODDKTPKGWSSZGR-UHFFFAOYSA-N 0.000 claims description 5
- XGLUFCRYDGBRPS-UHFFFAOYSA-N 2-[[4-[2-[ethyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoethyl]phenyl]sulfanylmethyl]benzoic acid Chemical compound C=1C=C(SCC=2C(=CC=CC=2)C(O)=O)C=CC=1CC(=O)N(CC)CC1=CC=C(C(F)(F)F)C=C1 XGLUFCRYDGBRPS-UHFFFAOYSA-N 0.000 claims description 5
- DFLAODURXLNIJS-UHFFFAOYSA-N 2-[[4-[3-[(2,4-difluorophenyl)methyl-heptylamino]-3-oxopropyl]phenoxy]methyl]benzoic acid Chemical compound C=1C=C(OCC=2C(=CC=CC=2)C(O)=O)C=CC=1CCC(=O)N(CCCCCCC)CC1=CC=C(F)C=C1F DFLAODURXLNIJS-UHFFFAOYSA-N 0.000 claims description 5
- BRAPPIAYKRVJSD-UHFFFAOYSA-N 2-[[4-[3-[benzyl(hexyl)amino]-3-oxopropyl]phenoxy]methyl]benzoic acid Chemical compound C=1C=C(OCC=2C(=CC=CC=2)C(O)=O)C=CC=1CCC(=O)N(CCCCCC)CC1=CC=CC=C1 BRAPPIAYKRVJSD-UHFFFAOYSA-N 0.000 claims description 5
- UTMNUBXVBHWRSP-UHFFFAOYSA-N 2-[[4-[3-[butyl-[(2,3-dimethoxyphenyl)methyl]amino]-3-oxopropyl]phenoxy]methyl]benzoic acid Chemical compound C=1C=C(OCC=2C(=CC=CC=2)C(O)=O)C=CC=1CCC(=O)N(CCCC)CC1=CC=CC(OC)=C1OC UTMNUBXVBHWRSP-UHFFFAOYSA-N 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- ZSECWGHWRUMBCP-UHFFFAOYSA-N 2-[[3-[2-[(2,4-difluorophenyl)methyl-heptylamino]-2-oxoethyl]phenyl]sulfanylmethyl]benzoic acid Chemical compound C=1C=CC(SCC=2C(=CC=CC=2)C(O)=O)=CC=1CC(=O)N(CCCCCCC)CC1=CC=C(F)C=C1F ZSECWGHWRUMBCP-UHFFFAOYSA-N 0.000 claims description 4
- CGAJIYOGBDNFEP-UHFFFAOYSA-N 2-[[4-[2-[(4-chlorophenyl)methyl-ethylamino]-2-oxoethyl]phenyl]sulfanylmethyl]benzoic acid Chemical compound C=1C=C(SCC=2C(=CC=CC=2)C(O)=O)C=CC=1CC(=O)N(CC)CC1=CC=C(Cl)C=C1 CGAJIYOGBDNFEP-UHFFFAOYSA-N 0.000 claims description 4
- NKKUNRCSUULMIN-UHFFFAOYSA-N 2-[[4-[3-[(2,3-dimethoxyphenyl)methyl-heptylamino]-3-oxopropyl]phenoxy]methyl]benzoic acid Chemical compound C=1C=C(OCC=2C(=CC=CC=2)C(O)=O)C=CC=1CCC(=O)N(CCCCCCC)CC1=CC=CC(OC)=C1OC NKKUNRCSUULMIN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 238000011161 development Methods 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims 1
- 239000012351 deprotecting agent Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 208
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 134
- 239000000203 mixture Substances 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
- 239000012453 solvate Substances 0.000 description 58
- 235000019439 ethyl acetate Nutrition 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- 239000012074 organic phase Substances 0.000 description 41
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 40
- 238000005160 1H NMR spectroscopy Methods 0.000 description 39
- 239000000047 product Substances 0.000 description 39
- 239000002904 solvent Substances 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
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- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 21
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 239000012267 brine Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 16
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
- 235000019341 magnesium sulphate Nutrition 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000002953 preparative HPLC Methods 0.000 description 15
- 239000005695 Ammonium acetate Substances 0.000 description 14
- 235000019257 ammonium acetate Nutrition 0.000 description 14
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
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- QKASDIPENBEWBU-UHFFFAOYSA-N methyl 2-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1CBr QKASDIPENBEWBU-UHFFFAOYSA-N 0.000 description 10
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
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- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 6
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- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 3
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- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 229940083542 sodium Drugs 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
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- FMMDBLMCSDRUPA-BPUTZDHNSA-N spiraprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)C(O)=O)CC1=CC=CC=C1 FMMDBLMCSDRUPA-BPUTZDHNSA-N 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
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- 239000012730 sustained-release form Substances 0.000 description 1
- 229960000651 tasosartan Drugs 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229960005187 telmisartan Drugs 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
- CXGTZJYQWSUFET-IBGZPJMESA-N tesaglitazar Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-IBGZPJMESA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 229960002277 tolazamide Drugs 0.000 description 1
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 229960002051 trandolapril Drugs 0.000 description 1
- 229960002651 trandolaprilat Drugs 0.000 description 1
- AHYHTSYNOHNUSH-HXFGRODQSA-N trandolaprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)C(O)=O)CC1=CC=CC=C1 AHYHTSYNOHNUSH-HXFGRODQSA-N 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000003146 transient transfection Methods 0.000 description 1
- 229950005696 utibapril Drugs 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 229960001729 voglibose Drugs 0.000 description 1
- 229950009999 zabicipril Drugs 0.000 description 1
- 229950005973 zabiciprilat Drugs 0.000 description 1
- 229960002769 zofenopril Drugs 0.000 description 1
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
- 229950001300 zofenoprilat Drugs 0.000 description 1
- UQWLOWFDKAFKAP-WXHSDQCUSA-N zofenoprilat Chemical compound C1[C@@H](C(O)=O)N(C(=O)[C@@H](CS)C)C[C@H]1SC1=CC=CC=C1 UQWLOWFDKAFKAP-WXHSDQCUSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0201935 | 2002-06-20 | ||
| SE0201935A SE0201935D0 (sv) | 2002-06-20 | 2002-06-20 | Therapeutic agents |
| SE0203826 | 2002-12-20 | ||
| SE0203826A SE0203826D0 (sv) | 2002-12-20 | 2002-12-20 | Therapeutic agents |
| PCT/GB2003/002584 WO2004000790A1 (en) | 2002-06-20 | 2003-06-17 | Ortho-substituted benzoic acid derivatives for the treatment of insulin resistance |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60319084D1 DE60319084D1 (de) | 2008-03-27 |
| DE60319084T2 true DE60319084T2 (de) | 2009-01-29 |
Family
ID=30002442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60319084T Expired - Lifetime DE60319084T2 (de) | 2002-06-20 | 2003-06-17 | Ortho-substituierte benzoesäurederivate zur behandlung von insulinresistenz |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7355069B2 (https=) |
| EP (1) | EP1517883B8 (https=) |
| JP (2) | JP3782818B2 (https=) |
| KR (1) | KR20050014013A (https=) |
| CN (1) | CN1319938C (https=) |
| AR (1) | AR039713A1 (https=) |
| AT (1) | ATE386013T1 (https=) |
| AU (1) | AU2003240099B2 (https=) |
| BR (1) | BR0311932A (https=) |
| CA (1) | CA2489834C (https=) |
| DE (1) | DE60319084T2 (https=) |
| DK (1) | DK1517883T3 (https=) |
| ES (1) | ES2299702T3 (https=) |
| IL (1) | IL165671A0 (https=) |
| IS (1) | IS7627A (https=) |
| MX (1) | MXPA04012686A (https=) |
| NO (1) | NO20045353L (https=) |
| PL (1) | PL375074A1 (https=) |
| PT (1) | PT1517883E (https=) |
| RU (1) | RU2004137094A (https=) |
| TW (1) | TWI282784B (https=) |
| WO (1) | WO2004000790A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6262118B1 (en) * | 1999-06-04 | 2001-07-17 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes and hyperlipidemia |
| US7576131B2 (en) * | 1999-06-04 | 2009-08-18 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes, hyperlipidemia and hyperuricemia |
| SE0104333D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| FR2875805B1 (fr) * | 2004-09-27 | 2006-12-29 | Genfit S A | Composes derives de n-(benzyl) phenylacetamide substitues, preparation et utilisations |
| GB0522433D0 (en) * | 2005-11-03 | 2005-12-14 | Astrazeneca Ab | Therapeutic agents |
| GB0522431D0 (en) * | 2005-11-03 | 2005-12-14 | Astrazeneca Ab | Chemical process |
Family Cites Families (34)
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| DK148576A (da) | 1975-04-18 | 1976-10-19 | Boehringer Mannheim Gmbh | Fenylalkankarbonsyrederivater og fremgangsmade til deres fremstilling |
| DE19615263A1 (de) | 1996-04-18 | 1997-10-23 | Bayer Ag | Benzyloxy-substituierte Phenylglycinolamide |
| BR9814087A (pt) | 1997-10-17 | 2000-10-03 | Aventis Pharm Prod Inc | Processos para mediar a atividade do receptor de ppar-gama, e para tratar uma condição fisiológica em um paciente |
| EP1040108B1 (en) | 1997-12-19 | 2004-02-25 | Schering Aktiengesellschaft | Ortho-anthranilamide derivatives as anti-coagulants |
| SE9801992D0 (sv) | 1998-06-04 | 1998-06-04 | Astra Ab | New 3-aryl-2-hydroxypropionic acid derivative I |
| GB9822473D0 (en) | 1998-10-16 | 1998-12-09 | Glaxo Group Ltd | Chemical compounds |
| NZ515086A (en) | 1999-04-28 | 2003-10-31 | Aventis Pharma Gmbh | Di-aryl acid derivatives as PPAR receptor ligands |
| EP1177176B1 (en) | 1999-04-28 | 2006-04-19 | Aventis Pharma Deutschland GmbH | Tri-aryl acid derivatives as ppar receptor ligands |
| JP4618845B2 (ja) | 1999-06-09 | 2011-01-26 | 杏林製薬株式会社 | ヒトペルオキシゾーム増殖薬活性化受容体（ＰＰＡＲ）αアゴニストとしての置換フェニルプロピオン酸誘導体 |
| GB9919411D0 (en) | 1999-08-18 | 1999-10-20 | Zeneca Ltd | Chemical compounds |
| SE0000772D0 (sv) | 2000-03-08 | 2000-03-08 | Astrazeneca Ab | Chemical compounds |
| US6509374B2 (en) | 2000-04-17 | 2003-01-21 | Novo Nordisk A/S | Compounds, their preparation and use |
| SE0003766D0 (sv) | 2000-10-18 | 2000-10-18 | Astrazeneca Ab | Novel formulation |
| EG26979A (en) | 2000-12-21 | 2015-03-01 | Astrazeneca Ab | Chemical compounds |
| GB0116955D0 (en) | 2001-07-11 | 2001-09-05 | Syngenta Ltd | Weed control process |
| GB0121337D0 (en) | 2001-09-04 | 2001-10-24 | Astrazeneca Ab | Chemical compounds |
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| GB0121622D0 (en) | 2001-09-07 | 2001-10-31 | Astrazeneca Ab | Chemical compounds |
| TWI331143B (en) | 2001-09-08 | 2010-10-01 | Astrazeneca Uk Ltd | Benzothiadiazepine derivatives, process for preparing them, and pharmaceutical composition comprising them |
| SE0104333D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| GB0229931D0 (en) | 2002-12-21 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| SE0104334D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| GB0209467D0 (en) | 2002-04-25 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
| GB0213669D0 (en) | 2002-06-14 | 2002-07-24 | Astrazeneca Ab | Chemical compounds |
| US7351858B2 (en) | 2002-06-20 | 2008-04-01 | Astrazeneca Ab | Ortho-substituted benzoic acid derivatives for the treatment of insulin resistance |
| SE0201936D0 (sv) | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | Therapeutic agents |
| SE0201937D0 (sv) | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | Therapeutic agents |
| GB0314130D0 (en) | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0314136D0 (en) | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0314131D0 (en) | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0314129D0 (en) | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0314075D0 (en) | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0314078D0 (en) | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0314260D0 (en) | 2003-06-19 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
-
2003
- 2003-06-17 PL PL03375074A patent/PL375074A1/xx not_active Application Discontinuation
- 2003-06-17 JP JP2004515007A patent/JP3782818B2/ja not_active Expired - Lifetime
- 2003-06-17 CN CNB038194740A patent/CN1319938C/zh not_active Expired - Fee Related
- 2003-06-17 KR KR10-2004-7020670A patent/KR20050014013A/ko not_active Withdrawn
- 2003-06-17 CA CA002489834A patent/CA2489834C/en not_active Expired - Fee Related
- 2003-06-17 BR BR0311932-7A patent/BR0311932A/pt not_active IP Right Cessation
- 2003-06-17 DE DE60319084T patent/DE60319084T2/de not_active Expired - Lifetime
- 2003-06-17 TW TW092116378A patent/TWI282784B/zh not_active IP Right Cessation
- 2003-06-17 US US10/518,007 patent/US7355069B2/en not_active Expired - Fee Related
- 2003-06-17 MX MXPA04012686A patent/MXPA04012686A/es not_active Application Discontinuation
- 2003-06-17 EP EP03732713A patent/EP1517883B8/en not_active Expired - Lifetime
- 2003-06-17 ES ES03732713T patent/ES2299702T3/es not_active Expired - Lifetime
- 2003-06-17 WO PCT/GB2003/002584 patent/WO2004000790A1/en not_active Ceased
- 2003-06-17 RU RU2004137094/04A patent/RU2004137094A/ru not_active Application Discontinuation
- 2003-06-17 AT AT03732713T patent/ATE386013T1/de not_active IP Right Cessation
- 2003-06-17 AU AU2003240099A patent/AU2003240099B2/en not_active Ceased
- 2003-06-17 DK DK03732713T patent/DK1517883T3/da active
- 2003-06-17 PT PT03732713T patent/PT1517883E/pt unknown
- 2003-06-20 AR ARP030102197A patent/AR039713A1/es not_active Application Discontinuation
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2004
- 2004-12-07 NO NO20045353A patent/NO20045353L/no not_active Application Discontinuation
- 2004-12-09 IL IL16567104A patent/IL165671A0/xx unknown
-
2005
- 2005-01-05 IS IS7627A patent/IS7627A/is unknown
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2006
- 2006-01-27 JP JP2006019068A patent/JP2006182782A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20050256198A1 (en) | 2005-11-17 |
| AU2003240099A1 (en) | 2004-01-06 |
| RU2004137094A (ru) | 2005-08-10 |
| ATE386013T1 (de) | 2008-03-15 |
| TWI282784B (en) | 2007-06-21 |
| IS7627A (is) | 2005-01-05 |
| DK1517883T3 (da) | 2008-05-26 |
| MXPA04012686A (es) | 2005-03-23 |
| DE60319084D1 (de) | 2008-03-27 |
| CA2489834C (en) | 2006-10-03 |
| CA2489834A1 (en) | 2003-12-31 |
| PL375074A1 (en) | 2005-11-14 |
| TW200409747A (en) | 2004-06-16 |
| US7355069B2 (en) | 2008-04-08 |
| HK1073838A1 (en) | 2005-10-21 |
| EP1517883A1 (en) | 2005-03-30 |
| CN1675171A (zh) | 2005-09-28 |
| ES2299702T3 (es) | 2008-06-01 |
| AR039713A1 (es) | 2005-03-09 |
| JP3782818B2 (ja) | 2006-06-07 |
| AU2003240099B2 (en) | 2007-02-01 |
| EP1517883B1 (en) | 2008-02-13 |
| PT1517883E (pt) | 2008-04-21 |
| IL165671A0 (en) | 2006-01-15 |
| BR0311932A (pt) | 2005-03-22 |
| JP2006182782A (ja) | 2006-07-13 |
| NO20045353L (no) | 2005-01-20 |
| KR20050014013A (ko) | 2005-02-05 |
| JP2005529970A (ja) | 2005-10-06 |
| EP1517883B8 (en) | 2008-05-21 |
| WO2004000790A1 (en) | 2003-12-31 |
| CN1319938C (zh) | 2007-06-06 |
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| 8364 | No opposition during term of opposition |