ZA200104126B - Methods of reducing serum glucose and triglyceride levels and for inhibiting angiogenesis using substituted indolealkanoic acids. - Google Patents
Methods of reducing serum glucose and triglyceride levels and for inhibiting angiogenesis using substituted indolealkanoic acids. Download PDFInfo
- Publication number
- ZA200104126B ZA200104126B ZA200104126A ZA200104126A ZA200104126B ZA 200104126 B ZA200104126 B ZA 200104126B ZA 200104126 A ZA200104126 A ZA 200104126A ZA 200104126 A ZA200104126 A ZA 200104126A ZA 200104126 B ZA200104126 B ZA 200104126B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- optionally substituted
- fluoro
- phenyl
- trifluoromethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 63
- 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 title claims description 6
- 239000008103 glucose Substances 0.000 title claims description 6
- 210000002966 serum Anatomy 0.000 title claims description 6
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims description 5
- 239000002253 acid Substances 0.000 title claims description 3
- 230000033115 angiogenesis Effects 0.000 title claims description 3
- 230000002401 inhibitory effect Effects 0.000 title claims description 3
- 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 title claims 2
- 150000007513 acids Chemical class 0.000 title description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 171
- 125000000217 alkyl group Chemical group 0.000 claims description 107
- 229910052736 halogen Inorganic materials 0.000 claims description 79
- 150000002367 halogens Chemical group 0.000 claims description 77
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 125000001153 fluoro group Chemical group F* 0.000 claims description 72
- 125000003545 alkoxy group Chemical group 0.000 claims description 65
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 64
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- -1 nitro, amino Chemical group 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 125000003282 alkyl amino group Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
- 208000002249 Diabetes Complications Diseases 0.000 claims description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- 206010012655 Diabetic complications Diseases 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 239000000651 prodrug Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000005605 benzo group Chemical group 0.000 claims 30
- 150000002431 hydrogen Chemical class 0.000 claims 28
- 125000001246 bromo group Chemical group Br* 0.000 claims 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 20
- 125000002541 furyl group Chemical group 0.000 claims 20
- 239000011593 sulfur Substances 0.000 claims 20
- 125000001544 thienyl group Chemical group 0.000 claims 20
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 17
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 15
- 125000004414 alkyl thio group Chemical group 0.000 claims 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 241000124008 Mammalia Species 0.000 claims 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 10
- 125000001589 carboacyl group Chemical group 0.000 claims 10
- 125000002346 iodo group Chemical group I* 0.000 claims 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 10
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 5
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical compound C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 claims 5
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 claims 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 5
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 5
- KDZASNPOEXNJBZ-UHFFFAOYSA-N thieno[2,3-d][1,2]thiazole Chemical compound S1N=CC2=C1C=CS2 KDZASNPOEXNJBZ-UHFFFAOYSA-N 0.000 claims 5
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 claims 5
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 claims 5
- 229930192474 thiophene Natural products 0.000 claims 5
- OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 claims 5
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 5
- 235000019000 fluorine Nutrition 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- IYIIESNRJJTDLA-UHFFFAOYSA-N 2-[3-[(3-nitrophenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC=CC=C2N(CC(=O)O)C=C1CC1=CC=CC([N+]([O-])=O)=C1 IYIIESNRJJTDLA-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- MGICLRNAZXDKAT-UHFFFAOYSA-N 2-(2-methylindol-1-yl)acetic acid Chemical compound C1=CC=C2N(CC(O)=O)C(C)=CC2=C1 MGICLRNAZXDKAT-UHFFFAOYSA-N 0.000 claims 1
- XGGQPJUUZQBRKN-UHFFFAOYSA-N 2-[2-methyl-3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC=CC=C2N(CC(O)=O)C(C)=C1CC1=NC2=C(F)C(F)=CC(F)=C2S1 XGGQPJUUZQBRKN-UHFFFAOYSA-N 0.000 claims 1
- QBQAVWVRMZYUGW-UHFFFAOYSA-N 2-[5-methyl-3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid Chemical compound FC1=CC(F)=C2SC(CC3=CN(CC(O)=O)C4=CC=C(C=C43)C)=NC2=C1F QBQAVWVRMZYUGW-UHFFFAOYSA-N 0.000 claims 1
- ISJXLKGPHQLSRN-UHFFFAOYSA-N 2-[5-phenoxy-3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C=1C=C2N(CC(=O)O)C=C(CC=3SC4=C(F)C=C(F)C(F)=C4N=3)C2=CC=1OC1=CC=CC=C1 ISJXLKGPHQLSRN-UHFFFAOYSA-N 0.000 claims 1
- OVRDKEPIWAYWQW-UHFFFAOYSA-N 2-[6-chloro-2-methyl-3-(4,5,7-trifluoro-1,3-benzothiazol-2-yl)indol-1-yl]acetic acid Chemical compound C12=CC=C(Cl)C=C2N(CC(O)=O)C(C)=C1C1=NC2=C(F)C(F)=CC(F)=C2S1 OVRDKEPIWAYWQW-UHFFFAOYSA-N 0.000 claims 1
- YAKLHRCDDYEKID-UHFFFAOYSA-N 2-[6-fluoro-3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC=C(F)C=C2N(CC(=O)O)C=C1CC1=NC2=C(F)C(F)=CC(F)=C2S1 YAKLHRCDDYEKID-UHFFFAOYSA-N 0.000 claims 1
- ZFHMZAGFUQFFEJ-UHFFFAOYSA-N 2-[6-morpholin-4-yl-3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C1=C2N(CC(=O)O)C=C(CC=3SC4=C(F)C=C(F)C(F)=C4N=3)C2=CC=C1N1CCOCC1 ZFHMZAGFUQFFEJ-UHFFFAOYSA-N 0.000 claims 1
- OTPMXLDHDYTZCJ-UHFFFAOYSA-N 2-[6-phenyl-3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C1=C2N(CC(=O)O)C=C(CC=3SC4=C(F)C=C(F)C(F)=C4N=3)C2=CC=C1C1=CC=CC=C1 OTPMXLDHDYTZCJ-UHFFFAOYSA-N 0.000 claims 1
- GUQBGRCBXABIBJ-UHFFFAOYSA-N 2-[7-bromo-3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC=CC(Br)=C2N(CC(=O)O)C=C1CC1=NC2=C(F)C(F)=CC(F)=C2S1 GUQBGRCBXABIBJ-UHFFFAOYSA-N 0.000 claims 1
- HMVAUYQQSPIFND-UHFFFAOYSA-N 2-[7-fluoro-3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC=CC(F)=C2N(CC(=O)O)C=C1CC1=NC2=C(F)C(F)=CC(F)=C2S1 HMVAUYQQSPIFND-UHFFFAOYSA-N 0.000 claims 1
- VKCHKAQCSBEZSI-UHFFFAOYSA-N 2-[7-methyl-3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid Chemical compound FC1=CC(F)=C2SC(CC=3C=4C=CC=C(C=4N(CC(O)=O)C=3)C)=NC2=C1F VKCHKAQCSBEZSI-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 238000002648 combination therapy Methods 0.000 claims 1
- PITCTBFYPGWOKF-UHFFFAOYSA-N ethyl 2-[3-[(3-nitrophenyl)methyl]indol-1-yl]acetate Chemical compound C12=CC=CC=C2N(CC(=O)OCC)C=C1CC1=CC=CC([N+]([O-])=O)=C1 PITCTBFYPGWOKF-UHFFFAOYSA-N 0.000 claims 1
- CJDWBNBHHMSCHC-UHFFFAOYSA-N ethyl 2-[3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetate Chemical compound C12=CC=CC=C2N(CC(=O)OCC)C=C1CC1=NC2=C(F)C(F)=CC(F)=C2S1 CJDWBNBHHMSCHC-UHFFFAOYSA-N 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
- KYHVTMFADJNSGS-UHFFFAOYSA-N {3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]-1h-indol-1-yl}acetic acid Chemical compound C12=CC=CC=C2N(CC(=O)O)C=C1CC1=NC2=C(F)C(F)=CC(F)=C2S1 KYHVTMFADJNSGS-UHFFFAOYSA-N 0.000 claims 1
- 239000003288 aldose reductase inhibitor Substances 0.000 description 7
- 229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 7
- 102000016912 Aldehyde Reductase Human genes 0.000 description 6
- 108010053754 Aldehyde reductase Proteins 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
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- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
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- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
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Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
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- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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| US11039598P | 1998-12-01 | 1998-12-01 |
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| ZA200104126A ZA200104126B (en) | 1998-12-01 | 2001-05-21 | Methods of reducing serum glucose and triglyceride levels and for inhibiting angiogenesis using substituted indolealkanoic acids. |
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| AU2001238718A1 (en) * | 2000-03-02 | 2001-09-12 | The Institutes For Pharmaceutical Discovery, Llc | Compositions containing a substituted indolealkanoic acid and an angiotensin converting enzyme inhibitor |
| WO2001085983A2 (en) * | 2000-05-09 | 2001-11-15 | The Institute For Pharmaceutical Discovery Llc | Methods for testing compounds useful for treating diabetic complications |
| TWI224101B (en) | 2001-06-20 | 2004-11-21 | Wyeth Corp | Substituted naphthyl indole derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1) |
| JP4399253B2 (ja) | 2001-06-20 | 2010-01-13 | ワイス | プラスミノゲンアクチベーターインヒビター−１（ｐａｉ−１）のインヒビターとしての、置換されたインドール酸誘導体 |
| JP2006514640A (ja) | 2002-12-10 | 2006-05-11 | ワイス | プラスミノゲンアクティベータインヒビターのインヒビターとしての置換３−アルキル及び３−アリールアルキル１ｈ−イル酢酸誘導体 |
| UA80453C2 (en) | 2002-12-10 | 2007-09-25 | Derivatives of substituted dyhydropyranoindol-3,4-dion as inhibitors of plasminogen activator inhibitor-1 (pai-1) | |
| CA2509222A1 (en) | 2002-12-10 | 2004-06-24 | Wyeth | Substituted indole oxo-acetyl amino acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| WO2004052855A2 (en) | 2002-12-10 | 2004-06-24 | Wyeth | Substituted 3-carbonyl-1h-indol-1-yl acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| DK1569901T3 (da) | 2002-12-10 | 2009-02-16 | Wyeth Corp | Aryl-, aryloxy- og alkoxysubstituerede 1H-indol-3-yl-glyoxylsyrederivater som inhibitorer af plasminogenaktivatorinhibitor-1 (PAI-1) |
| WO2004098498A2 (en) | 2003-04-28 | 2004-11-18 | Bayer Pharmaceuticals Corporation | Indole acetic acid derivatives and their use as pharmaceutical agents |
| US7342039B2 (en) | 2003-09-25 | 2008-03-11 | Wyeth | Substituted indole oximes |
| US7351726B2 (en) | 2003-09-25 | 2008-04-01 | Wyeth | Substituted oxadiazolidinediones |
| US7442805B2 (en) | 2003-09-25 | 2008-10-28 | Wyeth | Substituted sulfonamide-indoles |
| US7332521B2 (en) | 2003-09-25 | 2008-02-19 | Wyeth | Substituted indoles |
| US7141592B2 (en) | 2003-09-25 | 2006-11-28 | Wyeth | Substituted oxadiazolidinediones |
| US7446201B2 (en) | 2003-09-25 | 2008-11-04 | Wyeth | Substituted heteroaryl benzofuran acids |
| US7163954B2 (en) | 2003-09-25 | 2007-01-16 | Wyeth | Substituted naphthyl benzothiophene acids |
| US7582773B2 (en) | 2003-09-25 | 2009-09-01 | Wyeth | Substituted phenyl indoles |
| US7265148B2 (en) | 2003-09-25 | 2007-09-04 | Wyeth | Substituted pyrrole-indoles |
| US7268159B2 (en) | 2003-09-25 | 2007-09-11 | Wyeth | Substituted indoles |
| US7411083B2 (en) | 2003-09-25 | 2008-08-12 | Wyeth | Substituted acetic acid derivatives |
| GB0324763D0 (en) | 2003-10-23 | 2003-11-26 | Oxagen Ltd | Use of compounds in therapy |
| PL1750862T3 (pl) | 2004-06-04 | 2011-06-30 | Teva Pharma | Kompozycja farmaceutyczna zawierająca irbesartan |
| WO2006023865A1 (en) | 2004-08-23 | 2006-03-02 | Wyeth | Oxazolo-naphthyl acids as plaminogen activator inhibtor type-1 (pai-1) modulators useful in the treatment of thrombosis and cardiovascular diseases |
| AU2005311826A1 (en) * | 2004-11-30 | 2006-06-08 | Plexxikon, Inc. | Indole derivatives for use as PPAR active compounds |
| US7531568B2 (en) * | 2004-11-30 | 2009-05-12 | Plexxikon, Inc. | PPAR active compounds |
| JP2009504762A (ja) | 2005-08-17 | 2009-02-05 | ワイス | 置換インドール類およびそれらの使用方法 |
| US20070072904A1 (en) * | 2005-09-07 | 2007-03-29 | Jack Lin | PPAR active compounds |
| RU2458918C2 (ru) | 2006-07-22 | 2012-08-20 | Оксаген Лимитед | Соединения, обладающие антагонистической активностью по отношению к crth2 |
| PE20090159A1 (es) * | 2007-03-08 | 2009-02-21 | Plexxikon Inc | COMPUESTOS DERIVADOS DE ACIDO INDOL-PROPIONICO COMO MODULADORES PPARs |
| US7750027B2 (en) | 2008-01-18 | 2010-07-06 | Oxagen Limited | Compounds having CRTH2 antagonist activity |
| EP2250161B1 (en) | 2008-01-18 | 2013-10-16 | Atopix Therapeutics Limited | Compounds having crth2 antagonist activity |
| US20100022613A1 (en) | 2008-01-22 | 2010-01-28 | Oxagen Limited | Compounds Having CRTH2 Antagonist Activity |
| WO2009093029A1 (en) | 2008-01-22 | 2009-07-30 | Oxagen Limited | Compounds having crth2 antagonist activity |
| NZ789295A (en) | 2009-04-29 | 2024-02-23 | Amarin Pharmaceuticals Ie Ltd | Pharmaceutical compositions comprising epa and a cardiovascular agent and methods of using the same |
| US9650375B2 (en) | 2013-03-14 | 2017-05-16 | Merck Sharp & Dohme Corp. | Indole derivatives useful as anti-diabetic agents |
| GB201322273D0 (en) | 2013-12-17 | 2014-01-29 | Atopix Therapeutics Ltd | Process |
| GB201407807D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| GB201407820D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| WO2018002673A1 (en) | 2016-07-01 | 2018-01-04 | N4 Pharma Uk Limited | Novel formulations of angiotensin ii receptor antagonists |
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| US3557142A (en) | 1968-02-20 | 1971-01-19 | Sterling Drug Inc | 4,5,6,7-tetrahydro-indole-lower-alkanoic acids and esters |
| IE47592B1 (en) | 1977-12-29 | 1984-05-02 | Ici Ltd | Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture |
| JPS55167282A (en) | 1979-06-12 | 1980-12-26 | Fujisawa Pharmaceut Co Ltd | Piperazine derivative or its salt and its preparation |
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| WO1995006056A1 (en) | 1993-08-20 | 1995-03-02 | University Of Medicine & Dentistry Of New Jersey | Bridged polycationic polymer-oligonucleotide conjugates and methods for preparing same |
| GB9317764D0 (en) * | 1993-08-26 | 1993-10-13 | Pfizer Ltd | Therapeutic compound |
| US5641800A (en) * | 1994-07-21 | 1997-06-24 | Eli Lilly And Company | 1H-indole-1-functional sPLA2 inhibitors |
| TW401301B (en) * | 1994-10-07 | 2000-08-11 | Takeda Chemical Industries Ltd | Antihypertriglyceridemic composition |
| US5700819A (en) | 1994-11-29 | 1997-12-23 | Grelan Pharmaceutical Co., Ltd. | 2-substituted benzothiazole derivatives and prophylactic and therapeutic agents for the treatment of diabetic complications |
| IL117208A0 (en) | 1995-02-23 | 1996-06-18 | Nissan Chemical Ind Ltd | Indole type thiazolidines |
| JPH09165371A (ja) | 1995-10-09 | 1997-06-24 | Sankyo Co Ltd | 複素環化合物を含有する医薬 |
| ID27884A (id) * | 1998-03-31 | 2001-05-03 | Inst For Pharm Discovery Inc | Asam-asam indolealkanoat yang disubstitusikan. |
| TNSN99224A1 (fr) * | 1998-12-01 | 2005-11-10 | Inst For Pharm Discovery Inc | Methodes de reduction des niveaux de glucose et triglyceride en serum et pour suppression de l'antigenese utilisant les acides la indolealkanoique |
| AU2001238718A1 (en) * | 2000-03-02 | 2001-09-12 | The Institutes For Pharmaceutical Discovery, Llc | Compositions containing a substituted indolealkanoic acid and an angiotensin converting enzyme inhibitor |
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1999
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- 1999-12-01 CZ CZ20011864A patent/CZ20011864A3/cs unknown
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- 1999-12-01 HU HU0104953A patent/HUP0104953A3/hu unknown
- 1999-12-01 CN CN99814023A patent/CN1368883A/zh active Pending
- 1999-12-01 TR TR2001/01539T patent/TR200101539T2/tr unknown
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2000
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2001
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2002
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2005
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2010
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2011
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