OA11972A - Substituted phenoxyacetic acids. - Google Patents
Substituted phenoxyacetic acids. Download PDFInfo
- Publication number
- OA11972A OA11972A OA1200100338A OA1200100338A OA11972A OA 11972 A OA11972 A OA 11972A OA 1200100338 A OA1200100338 A OA 1200100338A OA 1200100338 A OA1200100338 A OA 1200100338A OA 11972 A OA11972 A OA 11972A
- Authority
- OA
- OAPI
- 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 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- -1 Cj-Cgalkoxy Chemical group 0.000 claims description 155
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 229960000583 acetic acid Drugs 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 58
- 229910052736 halogen Inorganic materials 0.000 claims description 55
- 150000002367 halogens Chemical class 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 55
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000001153 fluoro group Chemical group F* 0.000 claims description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
- 150000002431 hydrogen Chemical group 0.000 claims description 42
- 239000000460 chlorine Substances 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 23
- 125000003282 alkyl amino group Chemical group 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000005541 ACE inhibitor Substances 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000001246 bromo group Chemical group Br* 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 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 13
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000011593 sulfur Chemical group 0.000 claims description 12
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
- 208000002249 Diabetes Complications Diseases 0.000 claims description 10
- 206010012655 Diabetic complications Diseases 0.000 claims description 10
- 125000005605 benzo group Chemical group 0.000 claims description 10
- PZUABNHIHMIRAO-UHFFFAOYSA-N ethyl 2-[5-fluoro-2-[(3-nitrophenyl)methylcarbamoyl]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC(F)=CC=C1C(=O)NCC1=CC=CC([N+]([O-])=O)=C1 PZUABNHIHMIRAO-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 235000019000 fluorine Nutrition 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 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 7
- 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 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 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 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- YRZKYOFOFCQAJG-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-5-chlorophenoxy]acetate Chemical compound CCOC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(Br)C=C1F YRZKYOFOFCQAJG-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 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 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 239000000651 prodrug Chemical group 0.000 claims description 6
- ZLIGBZRXAQNUFO-UHFFFAOYSA-N (2-{[(4-bromo-2-fluorobenzyl)amino]carbonyl}-5-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(Br)C=C1F ZLIGBZRXAQNUFO-UHFFFAOYSA-N 0.000 claims description 5
- 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 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
- 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
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims description 5
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims description 5
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- QIIVXQRKYFRJCI-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-4,5-difluorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC(F)=C(F)C=C1C(=O)NCC1=CC=C(Br)C=C1F QIIVXQRKYFRJCI-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 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
- YFOZTUGVUPJZQN-UHFFFAOYSA-N 2-[5-chloro-2-[[3-(trifluoromethyl)phenyl]methylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC=CC(C(F)(F)F)=C1 YFOZTUGVUPJZQN-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
- RIWGNVAOPRSVNV-UHFFFAOYSA-N 2-[5-fluoro-2-[(4-methyl-3-nitrophenyl)methylcarbamoyl]phenoxy]acetic acid Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1CNC(=O)C1=CC=C(F)C=C1OCC(O)=O RIWGNVAOPRSVNV-UHFFFAOYSA-N 0.000 claims description 4
- DPDOABOONBUWMC-UHFFFAOYSA-N 2-[5-fluoro-2-[[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]methylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(F)=CC=C1C(=O)NCC1=NC2=CC(C(F)(F)F)=CC=C2S1 DPDOABOONBUWMC-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 108010007859 Lisinopril Proteins 0.000 claims description 4
- ZSHDPGCEJWXJLC-UHFFFAOYSA-N N-methyl-N-naphthalen-2-yl-2,3-dioxoquinoxaline-6-sulfonamide Chemical group CN(c1ccc2ccccc2c1)S(=O)(=O)c1ccc2=NC(=O)C(=O)N=c2c1 ZSHDPGCEJWXJLC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
- 150000001768 cations Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000003937 drug carrier Substances 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
- 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
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 4
- 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 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
- ZVIJVQUZAFMKDP-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamothioyl]-4,5-difluorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC(F)=C(F)C=C1C(=S)NCC1=CC=C(Br)C=C1F ZVIJVQUZAFMKDP-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
- 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 3
- VILIQBQRKXKVRC-UHFFFAOYSA-N 2-[2-[(4-bromo-2-fluorophenyl)methylcarbamoyl]-4-propoxyphenoxy]acetic acid Chemical compound CCCOC1=CC=C(OCC(O)=O)C(C(=O)NCC=2C(=CC(Br)=CC=2)F)=C1 VILIQBQRKXKVRC-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
- 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 3
- XYVNXMLOWRSSKZ-UHFFFAOYSA-N 2-[5-chloro-2-[(2,6-difluorophenyl)methylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=C(F)C=CC=C1F XYVNXMLOWRSSKZ-UHFFFAOYSA-N 0.000 claims description 3
- XCUJOTAIZCGZME-UHFFFAOYSA-N 2-[5-chloro-2-[(3,5-dimethoxyphenyl)methylcarbamoyl]phenoxy]acetic acid Chemical compound COC1=CC(OC)=CC(CNC(=O)C=2C(=CC(Cl)=CC=2)OCC(O)=O)=C1 XCUJOTAIZCGZME-UHFFFAOYSA-N 0.000 claims description 3
- IXKZEXYDDPKBHA-UHFFFAOYSA-N 2-[5-chloro-2-[(3-fluorophenyl)methylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC=CC(F)=C1 IXKZEXYDDPKBHA-UHFFFAOYSA-N 0.000 claims description 3
- QRFUWHJZABNGAP-UHFFFAOYSA-N 2-[5-chloro-2-[[4-(trifluoromethoxy)phenyl]methylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(OC(F)(F)F)C=C1 QRFUWHJZABNGAP-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 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 3
- JCZUIWYXULSXSW-UHFFFAOYSA-N idd594 Chemical compound OC(=O)COC1=CC(F)=CC=C1C(=S)NCC1=CC=C(Br)C=C1F JCZUIWYXULSXSW-UHFFFAOYSA-N 0.000 claims description 3
- 230000001771 impaired effect Effects 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 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 3
- 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 3
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 2
- 125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
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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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- A61P3/10—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
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- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14106899P | 1999-06-25 | 1999-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11972A true OA11972A (en) | 2006-04-18 |
Family
ID=22494031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200100338A OA11972A (en) | 1999-06-25 | 2000-06-23 | Substituted phenoxyacetic acids. |
Country Status (24)
| Country | Link |
|---|---|
| US (4) | US6420426B1 (cs) |
| EP (1) | EP1198451A2 (cs) |
| JP (1) | JP2003503381A (cs) |
| KR (1) | KR20020013936A (cs) |
| CN (1) | CN1364153A (cs) |
| AP (1) | AP2001002377A0 (cs) |
| AU (1) | AU5886900A (cs) |
| BG (1) | BG106351A (cs) |
| BR (1) | BR0011928A (cs) |
| CA (1) | CA2385798A1 (cs) |
| CZ (1) | CZ20014637A3 (cs) |
| EE (1) | EE200100708A (cs) |
| HU (1) | HUP0202384A3 (cs) |
| IL (1) | IL147197A0 (cs) |
| MX (1) | MXPA02003123A (cs) |
| NO (1) | NO20016272L (cs) |
| NZ (1) | NZ516290A (cs) |
| OA (1) | OA11972A (cs) |
| PL (1) | PL355857A1 (cs) |
| SK (1) | SK19152001A3 (cs) |
| TN (1) | TNSN00139A1 (cs) |
| TR (1) | TR200200619T2 (cs) |
| WO (1) | WO2001000566A2 (cs) |
| ZA (1) | ZA200200300B (cs) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2385798A1 (en) * | 1999-06-25 | 2001-01-04 | Michael C. Van Zandt | Substituted phenoxyacetic acids |
| US6958355B2 (en) | 2000-04-24 | 2005-10-25 | Aryx Therapeutics, Inc. | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
| US6680387B2 (en) | 2000-04-24 | 2004-01-20 | Aryx Therapeutics | 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 |
| WO2002024689A1 (en) | 2000-09-21 | 2002-03-28 | Aryx Therapeutics | Isoxazolidine compounds useful in the treatment of diabetes, hyperlipidemia, and atherosclerosis |
| HRP20031002A2 (en) * | 2001-06-07 | 2004-06-30 | Lilly Co Eli | Modulators of peroxisome proliferator activated receptors (ppar) |
| ES2297382T3 (es) | 2003-02-14 | 2008-05-01 | Eli Lilly And Company | Derivados de sulfonamida como moduladores de ppar. |
| BRPI0409914A (pt) * | 2003-04-30 | 2006-04-25 | Inst For Pharm Discovery Inc | ácidos carboxìlicos substituìdos |
| DE602005025755D1 (de) | 2004-06-04 | 2011-02-17 | Teva Pharma | Irbesartan enthaltende pharmazeutische zusammensetzung |
| EP1805136A1 (en) * | 2004-10-28 | 2007-07-11 | The Institutes for Pharmaceutical Discovery, LLC | 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 |
| EP2654428B1 (en) | 2010-12-22 | 2018-02-14 | 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 |
| 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 |
| 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0218728A1 (en) | 1985-04-03 | 1987-04-22 | 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 |
| CA2385798A1 (en) * | 1999-06-25 | 2001-01-04 | Michael C. Van Zandt | Substituted phenoxyacetic acids |
-
2000
- 2000-06-23 CA CA002385798A patent/CA2385798A1/en not_active Abandoned
- 2000-06-23 BR BR0011928-8A patent/BR0011928A/pt not_active IP Right Cessation
- 2000-06-23 IL IL14719700A patent/IL147197A0/xx unknown
- 2000-06-23 JP JP2001506979A patent/JP2003503381A/ja active Pending
- 2000-06-23 AU AU58869/00A patent/AU5886900A/en not_active Abandoned
- 2000-06-23 MX MXPA02003123A patent/MXPA02003123A/es unknown
- 2000-06-23 PL PL00355857A patent/PL355857A1/xx not_active Application Discontinuation
- 2000-06-23 KR KR1020017016636A patent/KR20020013936A/ko not_active Withdrawn
- 2000-06-23 US US09/603,817 patent/US6420426B1/en not_active Expired - Fee Related
- 2000-06-23 EP EP00944834A patent/EP1198451A2/en not_active Withdrawn
- 2000-06-23 AP APAP/P/2001/002377A patent/AP2001002377A0/en unknown
- 2000-06-23 CZ CZ20014637A patent/CZ20014637A3/cs unknown
- 2000-06-23 EE EEP200100708A patent/EE200100708A/xx unknown
- 2000-06-23 TR TR2002/00619T patent/TR200200619T2/xx unknown
- 2000-06-23 TN TNTNSN00139A patent/TNSN00139A1/fr unknown
- 2000-06-23 HU HU0202384A patent/HUP0202384A3/hu unknown
- 2000-06-23 WO PCT/US2000/017377 patent/WO2001000566A2/en not_active Ceased
- 2000-06-23 SK SK1915-2001A patent/SK19152001A3/sk unknown
- 2000-06-23 NZ NZ516290A patent/NZ516290A/xx unknown
- 2000-06-23 CN CN00809446A patent/CN1364153A/zh active Pending
- 2000-06-23 OA OA1200100338A patent/OA11972A/en 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 |
|---|---|
| HUP0202384A3 (en) | 2003-03-28 |
| BG106351A (bg) | 2002-09-30 |
| IL147197A0 (en) | 2002-08-14 |
| EE200100708A (et) | 2003-02-17 |
| PL355857A1 (en) | 2004-05-31 |
| HUP0202384A2 (hu) | 2002-11-28 |
| CN1364153A (zh) | 2002-08-14 |
| KR20020013936A (ko) | 2002-02-21 |
| EP1198451A2 (en) | 2002-04-24 |
| NZ516290A (en) | 2004-03-26 |
| TNSN00139A1 (fr) | 2005-11-10 |
| NO20016272L (no) | 2002-01-17 |
| US7189749B2 (en) | 2007-03-13 |
| US6420426B1 (en) | 2002-07-16 |
| WO2001000566A3 (en) | 2002-02-07 |
| JP2003503381A (ja) | 2003-01-28 |
| ZA200200300B (en) | 2003-08-27 |
| CZ20014637A3 (cs) | 2002-04-17 |
| US20030036558A1 (en) | 2003-02-20 |
| AP2001002377A0 (en) | 2001-12-31 |
| SK19152001A3 (sk) | 2002-06-04 |
| CA2385798A1 (en) | 2001-01-04 |
| WO2001000566A2 (en) | 2001-01-04 |
| NO20016272D0 (no) | 2001-12-20 |
| US20050239849A1 (en) | 2005-10-27 |
| AU5886900A (en) | 2001-01-31 |
| TR200200619T2 (tr) | 2003-01-21 |
| MXPA02003123A (es) | 2003-08-20 |
| BR0011928A (pt) | 2002-04-09 |
| US20070161631A1 (en) | 2007-07-12 |
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