BG106351A - Заместени феноксиоцетни киселини - Google Patents
Заместени феноксиоцетни киселини Download PDFInfo
- Publication number
- BG106351A BG106351A BG06351A BG10635102A BG106351A BG 106351 A BG106351 A BG 106351A BG 06351 A BG06351 A BG 06351A BG 10635102 A BG10635102 A BG 10635102A BG 106351 A BG106351 A BG 106351A
- Authority
- BG
- Bulgaria
- Prior art keywords
- fluoro
- phenoxy
- acetic acid
- benzylcarbamoyl
- bromo
- Prior art date
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- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 149
- 238000000034 method Methods 0.000 claims abstract description 42
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 239000003814 drug Substances 0.000 claims abstract description 12
- -1 benzothiazole- 2-yl Chemical group 0.000 claims description 134
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 66
- 239000000460 chlorine Substances 0.000 claims description 63
- 229910052736 halogen Inorganic materials 0.000 claims description 63
- 150000002367 halogens Chemical group 0.000 claims description 63
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 43
- 235000019000 fluorine Nutrition 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 38
- 239000011737 fluorine Substances 0.000 claims description 38
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000005541 ACE inhibitor Substances 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000011593 sulfur Chemical group 0.000 claims description 15
- 208000002249 Diabetes Complications Diseases 0.000 claims description 12
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 12
- 206010012655 Diabetic complications Diseases 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000005605 benzo group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- XFJRLYVSMQTRMF-UHFFFAOYSA-N 2-[4-amino-2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]phenoxy]acetic acid Chemical compound NC1=CC=C(OCC(O)=O)C(C(=O)NCC=2C(=CC(Br)=CC=2)F)=C1 XFJRLYVSMQTRMF-UHFFFAOYSA-N 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- HOFFXZBMYHZMTN-UHFFFAOYSA-N 2-[5-fluoro-2-[(3-nitrophenyl)methylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(F)=CC=C1C(=O)NCC1=CC=CC([N+]([O-])=O)=C1 HOFFXZBMYHZMTN-UHFFFAOYSA-N 0.000 claims description 7
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- BJQBRXOZXULXEC-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamothioyl]-5-fluoro-4-methylphenoxy]acetic acid Chemical compound C1=C(F)C(C)=CC(C(=S)NCC=2C(=CC(Br)=CC=2)F)=C1OCC(O)=O BJQBRXOZXULXEC-UHFFFAOYSA-N 0.000 claims description 6
- WIFYDCQQZFUIJL-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-5-fluoro-4-methylphenoxy]acetic acid Chemical compound C1=C(F)C(C)=CC(C(=O)NCC=2C(=CC(Br)=CC=2)F)=C1OCC(O)=O WIFYDCQQZFUIJL-UHFFFAOYSA-N 0.000 claims description 6
- GICVZCQDVFVIOE-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-5-methylsulfanylphenoxy]acetic acid Chemical compound OC(=O)COC1=CC(SC)=CC=C1C(=O)NCC1=CC=C(Br)C=C1F GICVZCQDVFVIOE-UHFFFAOYSA-N 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 206010056740 Genital discharge Diseases 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 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
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 6
- QNWFNORHWGKDRC-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-4-fluorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(F)C=C1C(=O)NCC1=CC=C(Br)C=C1F QNWFNORHWGKDRC-UHFFFAOYSA-N 0.000 claims description 5
- HDYSFMQCZKXNCP-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-4-hydroxyphenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(O)C=C1C(=O)NCC1=CC=C(Br)C=C1F HDYSFMQCZKXNCP-UHFFFAOYSA-N 0.000 claims description 5
- PGLZYJVSXDUOJJ-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-4-nitrophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1C(=O)NCC1=CC=C(Br)C=C1F PGLZYJVSXDUOJJ-UHFFFAOYSA-N 0.000 claims description 5
- LTOGMJNIFXKCMS-UHFFFAOYSA-N 2-[5-fluoro-2-[(3-nitrophenyl)methylcarbamothioyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(F)=CC=C1C(=S)NCC1=CC=CC([N+]([O-])=O)=C1 LTOGMJNIFXKCMS-UHFFFAOYSA-N 0.000 claims description 5
- AKYQRJAGXXZACK-UHFFFAOYSA-N 2-[5-fluoro-2-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methylcarbamothioyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(F)=CC=C1C(=S)NCC1=NC2=C(F)C(F)=CC(F)=C2S1 AKYQRJAGXXZACK-UHFFFAOYSA-N 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 238000011161 development Methods 0.000 claims description 5
- PJURKRPHVUPSAN-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-5-fluoro-4-methylphenoxy]acetate Chemical compound CCOC(=O)COC1=CC(F)=C(C)C=C1C(=O)NCC1=CC=C(Br)C=C1F PJURKRPHVUPSAN-UHFFFAOYSA-N 0.000 claims description 5
- YTFFFDWBVTZTOF-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-5-methylsulfanylphenoxy]acetate Chemical compound CCOC(=O)COC1=CC(SC)=CC=C1C(=O)NCC1=CC=C(Br)C=C1F YTFFFDWBVTZTOF-UHFFFAOYSA-N 0.000 claims description 5
- ZCAGEXZTORJQDZ-UHFFFAOYSA-N idd552 Chemical compound OC(=O)COC1=CC(F)=CC=C1C(=O)NCC1=NC2=C(F)C(F)=CC(F)=C2S1 ZCAGEXZTORJQDZ-UHFFFAOYSA-N 0.000 claims description 5
- VABIMMIJVWNHFI-UHFFFAOYSA-N (5-chloro-2-{[(3-nitrobenzyl)amino]carbonyl}phenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC=CC([N+]([O-])=O)=C1 VABIMMIJVWNHFI-UHFFFAOYSA-N 0.000 claims description 4
- RTVYLMOYEJCWKS-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-4-methylphenoxy]acetic acid Chemical compound CC1=CC=C(OCC(O)=O)C(C(=O)NCC=2C(=CC(Br)=CC=2)F)=C1 RTVYLMOYEJCWKS-UHFFFAOYSA-N 0.000 claims description 4
- JMXDFFYEGLOZLN-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-5-fluorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC(F)=CC=C1C(=O)NCC1=CC=C(Br)C=C1F JMXDFFYEGLOZLN-UHFFFAOYSA-N 0.000 claims description 4
- YGSXYQRXWUFBJS-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-5-methylsulfonylphenoxy]acetic acid Chemical compound OC(=O)COC1=CC(S(=O)(=O)C)=CC=C1C(=O)NCC1=CC=C(Br)C=C1F YGSXYQRXWUFBJS-UHFFFAOYSA-N 0.000 claims description 4
- ZOVORMKZRSIBOR-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC=C1C(=O)NCC1=CC=C(Br)C=C1F ZOVORMKZRSIBOR-UHFFFAOYSA-N 0.000 claims description 4
- ZNTJBHNQMHKQRE-UHFFFAOYSA-N 2-[4-bromo-2-[(4-bromo-2-fluorophenyl)methylcarbamothioyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=S)NCC1=CC=C(Br)C=C1F ZNTJBHNQMHKQRE-UHFFFAOYSA-N 0.000 claims description 4
- VMDJMZLCXYDEJN-UHFFFAOYSA-N 2-[4-bromo-5-fluoro-2-[(3-nitrophenyl)methylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(F)=C(Br)C=C1C(=O)NCC1=CC=CC([N+]([O-])=O)=C1 VMDJMZLCXYDEJN-UHFFFAOYSA-N 0.000 claims description 4
- UWRVTYXRWRFZLD-UHFFFAOYSA-N 2-[4-methyl-2-[(3-nitrophenyl)methylcarbamoyl]phenoxy]acetic acid Chemical compound CC1=CC=C(OCC(O)=O)C(C(=O)NCC=2C=C(C=CC=2)[N+]([O-])=O)=C1 UWRVTYXRWRFZLD-UHFFFAOYSA-N 0.000 claims description 4
- CYOWQKBVRUBBNK-UHFFFAOYSA-N 2-[5-chloro-2-[(3,4-dichlorophenyl)methylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(Cl)C(Cl)=C1 CYOWQKBVRUBBNK-UHFFFAOYSA-N 0.000 claims description 4
- NTGIAPVUCADTBR-UHFFFAOYSA-N 2-[5-chloro-2-[[3-fluoro-5-(trifluoromethyl)phenyl]methylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC(F)=CC(C(F)(F)F)=C1 NTGIAPVUCADTBR-UHFFFAOYSA-N 0.000 claims description 4
- KAKGITVNDMUJNY-UHFFFAOYSA-N 2-[5-chloro-2-[[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]methylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=NC2=CC(C(F)(F)F)=CC=C2S1 KAKGITVNDMUJNY-UHFFFAOYSA-N 0.000 claims description 4
- DRXGHGSGESTSRR-UHFFFAOYSA-N 2-[5-fluoro-2-[(3-nitrophenyl)methylcarbamothioyl]-4-phenylphenoxy]acetic acid Chemical compound OC(=O)COC1=CC(F)=C(C=2C=CC=CC=2)C=C1C(=S)NCC1=CC=CC([N+]([O-])=O)=C1 DRXGHGSGESTSRR-UHFFFAOYSA-N 0.000 claims description 4
- YTCQYMCDHKZLCQ-UHFFFAOYSA-N 2-[5-fluoro-4-methyl-2-[(3-nitrophenyl)methylcarbamothioyl]phenoxy]acetic acid Chemical compound C1=C(F)C(C)=CC(C(=S)NCC=2C=C(C=CC=2)[N+]([O-])=O)=C1OCC(O)=O YTCQYMCDHKZLCQ-UHFFFAOYSA-N 0.000 claims description 4
- JMOWSLHICGJXMV-UHFFFAOYSA-N 2-[5-fluoro-4-methyl-2-[(3-nitrophenyl)methylcarbamoyl]phenoxy]acetic acid Chemical compound C1=C(F)C(C)=CC(C(=O)NCC=2C=C(C=CC=2)[N+]([O-])=O)=C1OCC(O)=O JMOWSLHICGJXMV-UHFFFAOYSA-N 0.000 claims description 4
- 108010007859 Lisinopril Proteins 0.000 claims description 4
- 229960000830 captopril Drugs 0.000 claims description 4
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 claims description 4
- UXNKVDGMAAIZOF-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamothioyl]-5-fluoro-4-methylphenoxy]acetate Chemical compound CCOC(=O)COC1=CC(F)=C(C)C=C1C(=S)NCC1=CC=C(Br)C=C1F UXNKVDGMAAIZOF-UHFFFAOYSA-N 0.000 claims description 4
- YNJOZKDLUBTLDQ-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-5-fluoro-4-morpholin-4-ylphenoxy]acetate Chemical compound CCOC(=O)COC1=CC(F)=C(N2CCOCC2)C=C1C(=O)NCC1=CC=C(Br)C=C1F YNJOZKDLUBTLDQ-UHFFFAOYSA-N 0.000 claims description 4
- SYDLYRPUYXWHBG-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-5-methylsulfonylphenoxy]acetate Chemical compound CCOC(=O)COC1=CC(S(C)(=O)=O)=CC=C1C(=O)NCC1=CC=C(Br)C=C1F SYDLYRPUYXWHBG-UHFFFAOYSA-N 0.000 claims description 4
- PROPWVFZYMARHF-UHFFFAOYSA-N ethyl 2-[5-fluoro-2-[(3-nitrophenyl)methylcarbamothioyl]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC(F)=CC=C1C(=S)NCC1=CC=CC([N+]([O-])=O)=C1 PROPWVFZYMARHF-UHFFFAOYSA-N 0.000 claims description 4
- RUKXEKOLJGCYPT-UHFFFAOYSA-N ethyl 2-[5-fluoro-2-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methylcarbamothioyl]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC(F)=CC=C1C(=S)NCC1=NC2=C(F)C(F)=CC(F)=C2S1 RUKXEKOLJGCYPT-UHFFFAOYSA-N 0.000 claims description 4
- IXQLQDGUSWSVCR-UHFFFAOYSA-N ethyl 2-[5-fluoro-2-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methylcarbamoyl]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC(F)=CC=C1C(=O)NCC1=NC2=C(F)C(F)=CC(F)=C2S1 IXQLQDGUSWSVCR-UHFFFAOYSA-N 0.000 claims description 4
- 229960002394 lisinopril Drugs 0.000 claims description 4
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 claims description 4
- AJDOUWBFADNZSF-UHFFFAOYSA-N prop-2-enyl 2-[4-acetamido-2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]phenoxy]acetate Chemical compound CC(=O)NC1=CC=C(OCC(=O)OCC=C)C(C(=O)NCC=2C(=CC(Br)=CC=2)F)=C1 AJDOUWBFADNZSF-UHFFFAOYSA-N 0.000 claims description 4
- CTPQRCYNPAZLQY-UHFFFAOYSA-N tert-butyl 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-4-nitrophenoxy]acetate Chemical compound CC(C)(C)OC(=O)COC1=CC=C([N+]([O-])=O)C=C1C(=O)NCC1=CC=C(Br)C=C1F CTPQRCYNPAZLQY-UHFFFAOYSA-N 0.000 claims description 4
- WLIJXMNMNJIVPE-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-ylmethylcarbamoyl)-5-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(OCO2)C2=C1 WLIJXMNMNJIVPE-UHFFFAOYSA-N 0.000 claims description 3
- XBMXVKFFSUQAHB-UHFFFAOYSA-N 2-[2-(benzylcarbamoyl)-5-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC=CC=C1 XBMXVKFFSUQAHB-UHFFFAOYSA-N 0.000 claims description 3
- OTLXMBAPSLICJO-UHFFFAOYSA-N 2-[2-[(2-fluorophenyl)methylcarbamoyl]-4-propoxyphenoxy]acetic acid Chemical compound CCCOC1=CC=C(OCC(O)=O)C(C(=O)NCC=2C(=CC=CC=2)F)=C1 OTLXMBAPSLICJO-UHFFFAOYSA-N 0.000 claims description 3
- UTPMSWHUAYAZNH-UHFFFAOYSA-N 2-[2-[(3-nitrophenyl)methylcarbamothioyl]-4-(trifluoromethoxy)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(OC(F)(F)F)C=C1C(=S)NCC1=CC=CC([N+]([O-])=O)=C1 UTPMSWHUAYAZNH-UHFFFAOYSA-N 0.000 claims description 3
- PKFIBQUBQLMCAA-UHFFFAOYSA-N 2-[2-[(3-nitrophenyl)methylcarbamoyl]-4-(trifluoromethoxy)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(OC(F)(F)F)C=C1C(=O)NCC1=CC=CC([N+]([O-])=O)=C1 PKFIBQUBQLMCAA-UHFFFAOYSA-N 0.000 claims description 3
- FNEOEALAHYHEOA-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-3,5-difluorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC(F)=CC(F)=C1C(=O)NCC1=CC=C(Br)C=C1F FNEOEALAHYHEOA-UHFFFAOYSA-N 0.000 claims description 3
- YSZMPUHDCYUHMM-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-4-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C(=O)NCC1=CC=C(Br)C=C1F YSZMPUHDCYUHMM-UHFFFAOYSA-N 0.000 claims description 3
- MKYJWXIBUSTLQR-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-4-methoxyphenoxy]acetic acid Chemical compound COC1=CC=C(OCC(O)=O)C(C(=O)NCC=2C(=CC(Br)=CC=2)F)=C1 MKYJWXIBUSTLQR-UHFFFAOYSA-N 0.000 claims description 3
- FJIZCSOCMULOCM-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-5-methoxyphenoxy]acetic acid Chemical compound OC(=O)COC1=CC(OC)=CC=C1C(=O)NCC1=CC=C(Br)C=C1F FJIZCSOCMULOCM-UHFFFAOYSA-N 0.000 claims description 3
- AQRVSBJPTIETHB-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-5-methylphenoxy]acetic acid Chemical compound OC(=O)COC1=CC(C)=CC=C1C(=O)NCC1=CC=C(Br)C=C1F AQRVSBJPTIETHB-UHFFFAOYSA-N 0.000 claims description 3
- PAOIFRPAIJVWIK-UHFFFAOYSA-N 2-[2-[(4-bromophenyl)methylcarbamoyl]-5-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(Br)C=C1 PAOIFRPAIJVWIK-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- 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
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Neurology (AREA)
- Emergency Medicine (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14106899P | 1999-06-25 | 1999-06-25 | |
| PCT/US2000/017377 WO2001000566A2 (en) | 1999-06-25 | 2000-06-23 | Substituted phenoxyacetic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG106351A true BG106351A (bg) | 2002-09-30 |
Family
ID=22494031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG06351A BG106351A (bg) | 1999-06-25 | 2002-01-25 | Заместени феноксиоцетни киселини |
Country Status (24)
| Country | Link |
|---|---|
| US (4) | US6420426B1 (et) |
| EP (1) | EP1198451A2 (et) |
| JP (1) | JP2003503381A (et) |
| KR (1) | KR20020013936A (et) |
| CN (1) | CN1364153A (et) |
| AP (1) | AP2001002377A0 (et) |
| AU (1) | AU5886900A (et) |
| BG (1) | BG106351A (et) |
| BR (1) | BR0011928A (et) |
| CA (1) | CA2385798A1 (et) |
| CZ (1) | CZ20014637A3 (et) |
| EE (1) | EE200100708A (et) |
| HU (1) | HUP0202384A3 (et) |
| IL (1) | IL147197A0 (et) |
| MX (1) | MXPA02003123A (et) |
| NO (1) | NO20016272L (et) |
| NZ (1) | NZ516290A (et) |
| OA (1) | OA11972A (et) |
| PL (1) | PL355857A1 (et) |
| SK (1) | SK19152001A3 (et) |
| TN (1) | TNSN00139A1 (et) |
| TR (1) | TR200200619T2 (et) |
| WO (1) | WO2001000566A2 (et) |
| ZA (1) | ZA200200300B (et) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TNSN00139A1 (fr) * | 1999-06-25 | 2005-11-10 | Inst For Pharm Discovery Inc | Acides phenoxyacetiques substitues |
| US6680387B2 (en) | 2000-04-24 | 2004-01-20 | Aryx Therapeutics | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
| US6958355B2 (en) | 2000-04-24 | 2005-10-25 | Aryx Therapeutics, Inc. | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
| US6768008B2 (en) * | 2000-04-24 | 2004-07-27 | Aryx Therapeutics | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
| KR100356374B1 (ko) * | 2000-09-14 | 2002-10-19 | 사회복지법인삼성생명공익재단(삼성서울병원) | 안지오텐신 전환효소 억제제의 부작용으로 발생하는마른기침을 저해하기 위한 철분을 포함하는 기침 저해조성물 |
| AU2001294673A1 (en) | 2000-09-21 | 2002-04-02 | Aryx Therapeutics | Isoxazolidine compounds useful in the treatment of diabetes, hyperlipidemia, andatherosclerosis |
| EA200400011A1 (ru) | 2001-06-07 | 2004-06-24 | Эли Лилли Энд Компани | Модуляторы рецепторов, активируемых пролифераторами пероксисом (prar) |
| CN1751037A (zh) | 2003-02-14 | 2006-03-22 | 伊莱利利公司 | 作为ppar调节剂的磺酰胺衍生物 |
| CN1812977A (zh) * | 2003-04-30 | 2006-08-02 | 药物研发有限责任公司 | 取代羧酸 |
| ES2282062T1 (es) | 2004-06-04 | 2007-10-16 | Teva Pharmaceutical Industries Ltd. | Composicion farmaceutica que contiene irbesartan. |
| TW200630327A (en) * | 2004-10-28 | 2006-09-01 | Inst For Pharm Discovery Inc | Substituted phenylalkanoic acids |
| GB0427603D0 (en) * | 2004-12-16 | 2005-01-19 | Novartis Ag | Organic compounds |
| US10640457B2 (en) | 2009-12-10 | 2020-05-05 | The Trustees Of Columbia University In The City Of New York | Histone acetyltransferase activators and uses thereof |
| WO2012088420A1 (en) | 2010-12-22 | 2012-06-28 | The Trustees Of Columbia University In The City Of New York | Histone acetyltransferase modulators and usese thereof |
| WO2018002673A1 (en) | 2016-07-01 | 2018-01-04 | N4 Pharma Uk Limited | Novel formulations of angiotensin ii receptor antagonists |
| CN109289696B (zh) * | 2018-10-29 | 2022-03-22 | 天津先光化工有限公司 | 一种咪唑啉两性表面活性剂的制备方法 |
| CN114790133B (zh) * | 2021-01-26 | 2024-06-18 | 江苏中旗科技股份有限公司 | 一种以2-氯-4-氨基苯腈为原料合成2-氯-4-氟苯甲酸的方法 |
| CN114790139B (zh) * | 2021-01-26 | 2024-06-18 | 江苏中旗科技股份有限公司 | 一种以2-氯-4-氨基溴苯为原料合成2-氯-4-氟苯甲酸的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986005779A1 (en) | 1985-04-03 | 1986-10-09 | Yamanouchi Pharmaceutical Co., Ltd. | Phenylene derivatives |
| JPH04297466A (ja) | 1990-06-22 | 1992-10-21 | Nippon Shinyaku Co Ltd | テトラゾール誘導体及び医薬 |
| EP0664788A1 (de) * | 1992-10-16 | 1995-08-02 | Byk Nederland BV | Substituierte ethanolaminester |
| GB9511694D0 (en) * | 1995-06-09 | 1995-08-02 | Fujisawa Pharmaceutical Co | Benzamide derivatives |
| TNSN00139A1 (fr) * | 1999-06-25 | 2005-11-10 | Inst For Pharm Discovery Inc | Acides phenoxyacetiques substitues |
-
2000
- 2000-06-23 TN TNTNSN00139A patent/TNSN00139A1/fr unknown
- 2000-06-23 AP APAP/P/2001/002377A patent/AP2001002377A0/en unknown
- 2000-06-23 SK SK1915-2001A patent/SK19152001A3/sk unknown
- 2000-06-23 AU AU58869/00A patent/AU5886900A/en not_active Abandoned
- 2000-06-23 US US09/603,817 patent/US6420426B1/en not_active Expired - Fee Related
- 2000-06-23 NZ NZ516290A patent/NZ516290A/xx unknown
- 2000-06-23 WO PCT/US2000/017377 patent/WO2001000566A2/en not_active Ceased
- 2000-06-23 HU HU0202384A patent/HUP0202384A3/hu unknown
- 2000-06-23 JP JP2001506979A patent/JP2003503381A/ja active Pending
- 2000-06-23 IL IL14719700A patent/IL147197A0/xx unknown
- 2000-06-23 CN CN00809446A patent/CN1364153A/zh active Pending
- 2000-06-23 EP EP00944834A patent/EP1198451A2/en not_active Withdrawn
- 2000-06-23 CZ CZ20014637A patent/CZ20014637A3/cs unknown
- 2000-06-23 CA CA002385798A patent/CA2385798A1/en not_active Abandoned
- 2000-06-23 TR TR2002/00619T patent/TR200200619T2/xx unknown
- 2000-06-23 KR KR1020017016636A patent/KR20020013936A/ko not_active Withdrawn
- 2000-06-23 PL PL00355857A patent/PL355857A1/xx not_active Application Discontinuation
- 2000-06-23 OA OA1200100338A patent/OA11972A/en unknown
- 2000-06-23 EE EEP200100708A patent/EE200100708A/et unknown
- 2000-06-23 BR BR0011928-8A patent/BR0011928A/pt not_active IP Right Cessation
- 2000-06-23 MX MXPA02003123A patent/MXPA02003123A/es unknown
-
2001
- 2001-12-20 NO NO20016272A patent/NO20016272L/no not_active Application Discontinuation
-
2002
- 2002-01-14 ZA ZA200200300A patent/ZA200200300B/xx unknown
- 2002-01-25 BG BG06351A patent/BG106351A/bg unknown
- 2002-07-16 US US10/195,964 patent/US20030036558A1/en not_active Abandoned
-
2003
- 2003-09-12 US US10/662,135 patent/US7189749B2/en not_active Expired - Fee Related
-
2007
- 2007-03-13 US US11/685,336 patent/US20070161631A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200200300B (en) | 2003-08-27 |
| NO20016272D0 (no) | 2001-12-20 |
| IL147197A0 (en) | 2002-08-14 |
| US6420426B1 (en) | 2002-07-16 |
| OA11972A (en) | 2006-04-18 |
| AU5886900A (en) | 2001-01-31 |
| CN1364153A (zh) | 2002-08-14 |
| US20030036558A1 (en) | 2003-02-20 |
| US20050239849A1 (en) | 2005-10-27 |
| EE200100708A (et) | 2003-02-17 |
| TR200200619T2 (tr) | 2003-01-21 |
| TNSN00139A1 (fr) | 2005-11-10 |
| CA2385798A1 (en) | 2001-01-04 |
| CZ20014637A3 (cs) | 2002-04-17 |
| NO20016272L (no) | 2002-01-17 |
| PL355857A1 (en) | 2004-05-31 |
| HUP0202384A2 (hu) | 2002-11-28 |
| BR0011928A (pt) | 2002-04-09 |
| JP2003503381A (ja) | 2003-01-28 |
| US20070161631A1 (en) | 2007-07-12 |
| SK19152001A3 (sk) | 2002-06-04 |
| NZ516290A (en) | 2004-03-26 |
| KR20020013936A (ko) | 2002-02-21 |
| WO2001000566A3 (en) | 2002-02-07 |
| US7189749B2 (en) | 2007-03-13 |
| WO2001000566A2 (en) | 2001-01-04 |
| AP2001002377A0 (en) | 2001-12-31 |
| EP1198451A2 (en) | 2002-04-24 |
| HUP0202384A3 (en) | 2003-03-28 |
| MXPA02003123A (es) | 2003-08-20 |
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