ZA200506551B - Benzopyran compounds useful for treating inflammatory conditions - Google Patents
Benzopyran compounds useful for treating inflammatory conditions Download PDFInfo
- Publication number
- ZA200506551B ZA200506551B ZA200506551A ZA200506551A ZA200506551B ZA 200506551 B ZA200506551 B ZA 200506551B ZA 200506551 A ZA200506551 A ZA 200506551A ZA 200506551 A ZA200506551 A ZA 200506551A ZA 200506551 B ZA200506551 B ZA 200506551B
- Authority
- ZA
- South Africa
- Prior art keywords
- chromene
- carboxylic acid
- trifluoromethyl
- chloro
- acid
- Prior art date
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- 230000004968 inflammatory condition Effects 0.000 title description 4
- 150000001562 benzopyrans Chemical class 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 124
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 58
- 229910052708 sodium Inorganic materials 0.000 claims description 58
- 239000011734 sodium Substances 0.000 claims description 58
- -1 8-chloro-6-ethoxy-2-(trifluoromethyl)-2H-chromene Chemical compound 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- DEBZQUFVQZPPLC-UHFFFAOYSA-N 2h-chromene-3-carboxylic acid Chemical compound C1=CC=C2OCC(C(=O)O)=CC2=C1 DEBZQUFVQZPPLC-UHFFFAOYSA-N 0.000 claims description 2
- FKRGMKAZITYKGR-UHFFFAOYSA-N 6-chloro-8-(4-methylphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CC(Cl)=CC2=C1OC(C(F)(F)F)C(C(O)=O)=C2 FKRGMKAZITYKGR-UHFFFAOYSA-N 0.000 claims description 2
- WBAUJPYWZXLTGY-UHFFFAOYSA-N 6-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(CC)=CC=C21 WBAUJPYWZXLTGY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 claims 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 4
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 3
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 3
- FCYUPOCBNOAMHF-HFEGYEGKSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)c1ccccc1.C[C@@H](N)c1ccccc1 FCYUPOCBNOAMHF-HFEGYEGKSA-N 0.000 claims 2
- QSLSQLYQCKEGMS-SECBINFHSA-N (2R)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid Chemical compound FC([C@@H]1OC2=CC=CC=C2C=C1C(=O)O)(F)F QSLSQLYQCKEGMS-SECBINFHSA-N 0.000 claims 2
- DEBZQUFVQZPPLC-UHFFFAOYSA-M 2h-chromene-3-carboxylate Chemical compound C1=CC=C2OCC(C(=O)[O-])=CC2=C1 DEBZQUFVQZPPLC-UHFFFAOYSA-M 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- FCYUPOCBNOAMHF-VGMFFHCQSA-N (1s)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1.C[C@H](N)C1=CC=CC=C1 FCYUPOCBNOAMHF-VGMFFHCQSA-N 0.000 claims 1
- IEWFZNLCMANOLT-QGZVFWFLSA-N (2r)-6-chloro-8-(4-ethylphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(CC)=CC=C1C1=CC(Cl)=CC2=C1O[C@@H](C(F)(F)F)C(C(O)=O)=C2 IEWFZNLCMANOLT-QGZVFWFLSA-N 0.000 claims 1
- WBAUJPYWZXLTGY-LLVKDONJSA-N (2r)-6-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@@H](C(F)(F)F)C(C(O)=O)=CC2=CC(CC)=CC=C21 WBAUJPYWZXLTGY-LLVKDONJSA-N 0.000 claims 1
- UXGOCCRFHXHIQD-MRXNPFEDSA-N (2r)-7-(4-chloro-2-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC(Cl)=CC=C1OC1=CC=C(C=C([C@@H](O2)C(F)(F)F)C(O)=O)C2=C1 UXGOCCRFHXHIQD-MRXNPFEDSA-N 0.000 claims 1
- DJARNOZMDSUMPO-KRWDZBQOSA-N (2s)-6-chloro-8-(4-methoxy-3-methylphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C)C(OC)=CC=C1C1=CC(Cl)=CC2=C1O[C@H](C(F)(F)F)C(C(O)=O)=C2 DJARNOZMDSUMPO-KRWDZBQOSA-N 0.000 claims 1
- XMHBNUGXXWTIHQ-UHFFFAOYSA-N 2-(trifluoromethyl)-7-(2,4,6-trimethylphenoxy)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC(C)=CC(C)=C1OC1=CC=C(C=C(C(O2)C(F)(F)F)C(O)=O)C2=C1 XMHBNUGXXWTIHQ-UHFFFAOYSA-N 0.000 claims 1
- OCFSUOIICRENCM-UHFFFAOYSA-N 5,7,8-trichloro-6-methoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C(Cl)C(OC)=C(Cl)C(Cl)=C21 OCFSUOIICRENCM-UHFFFAOYSA-N 0.000 claims 1
- QXTWPFQARQBXAV-UHFFFAOYSA-N 5-(4-ethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(CC)=CC=C1OC1=CC=CC2=C1C=C(C(O)=O)C(C(F)(F)F)O2 QXTWPFQARQBXAV-UHFFFAOYSA-N 0.000 claims 1
- MXEPMTUZWOMEQK-UHFFFAOYSA-N 6,8-dichloro-5,7-dimethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C(Cl)C(C)=C(Cl)C(C)=C21 MXEPMTUZWOMEQK-UHFFFAOYSA-N 0.000 claims 1
- XWLRSFNRJDMWFN-UHFFFAOYSA-N 6,8-dichloro-5-(2,5-dimethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC=C(C)C(OC=2C=3C=C(C(OC=3C(Cl)=CC=2Cl)C(F)(F)F)C(O)=O)=C1 XWLRSFNRJDMWFN-UHFFFAOYSA-N 0.000 claims 1
- OBUDAKFQDWSDSX-UHFFFAOYSA-N 6,8-dichloro-7-(2-ethylbutoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C(Cl)C(OCC(CC)CC)=C(Cl)C=C21 OBUDAKFQDWSDSX-UHFFFAOYSA-N 0.000 claims 1
- LSWJSMPFYVYUMN-UHFFFAOYSA-N 6,8-dichloro-7-(2-methylpropylamino)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C(Cl)C(NCC(C)C)=C(Cl)C=C21 LSWJSMPFYVYUMN-UHFFFAOYSA-N 0.000 claims 1
- TZVBQHMPMZKLIF-UHFFFAOYSA-N 6,8-dichloro-7-(propylamino)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C(Cl)C(NCCC)=C(Cl)C=C21 TZVBQHMPMZKLIF-UHFFFAOYSA-N 0.000 claims 1
- AXLIJRCKRUPBPQ-UHFFFAOYSA-N 6,8-dimethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(C)=CC(C)=C21 AXLIJRCKRUPBPQ-UHFFFAOYSA-N 0.000 claims 1
- BELRCUBXENPLRO-UHFFFAOYSA-N 6-(3-propan-2-ylphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC(C)C1=CC=CC(C=2C=C3C=C(C(OC3=CC=2)C(F)(F)F)C(O)=O)=C1 BELRCUBXENPLRO-UHFFFAOYSA-N 0.000 claims 1
- ZONDUOZXPGYCKH-UHFFFAOYSA-N 6-bromo-8-ethoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Br)C=C2OCC ZONDUOZXPGYCKH-UHFFFAOYSA-N 0.000 claims 1
- WBPWGFWTMGWTGP-UHFFFAOYSA-N 6-chloro-7-(2-ethylbutoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(OCC(CC)CC)C(Cl)=C2 WBPWGFWTMGWTGP-UHFFFAOYSA-N 0.000 claims 1
- GVJNKLZNXNMOTC-UHFFFAOYSA-N 6-chloro-7-(2-ethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CCC1=CC=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)C(C(F)(F)F)O2 GVJNKLZNXNMOTC-UHFFFAOYSA-N 0.000 claims 1
- FLOREOMIXZSKSJ-UHFFFAOYSA-N 6-chloro-7-(2-propylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CCCC1=CC=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)C(C(F)(F)F)O2 FLOREOMIXZSKSJ-UHFFFAOYSA-N 0.000 claims 1
- NUTMWFIADMUYAY-UHFFFAOYSA-N 6-chloro-7-(3-methylbutylamino)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(NCCC(C)C)C(Cl)=C2 NUTMWFIADMUYAY-UHFFFAOYSA-N 0.000 claims 1
- FGECXYBKTZTRGL-UHFFFAOYSA-N 6-chloro-7-[(3-chloro-2-methoxy-5-methylphenyl)methyl]-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound COC1=C(Cl)C=C(C)C=C1CC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)C(C(F)(F)F)O2 FGECXYBKTZTRGL-UHFFFAOYSA-N 0.000 claims 1
- HYPSQWDDIAYDDS-UHFFFAOYSA-N 6-chloro-7-[[methyl(propan-2-yl)amino]methyl]-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(CN(C)C(C)C)C(Cl)=C2 HYPSQWDDIAYDDS-UHFFFAOYSA-N 0.000 claims 1
- DKDCQJVWWVADBZ-UHFFFAOYSA-N 6-chloro-7-propoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(OCCC)C(Cl)=C2 DKDCQJVWWVADBZ-UHFFFAOYSA-N 0.000 claims 1
- MXTLFMOMFVUDAX-UHFFFAOYSA-N 6-chloro-8-(2-ethoxyphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CCOC1=CC=CC=C1C1=CC(Cl)=CC2=C1OC(C(F)(F)F)C(C(O)=O)=C2 MXTLFMOMFVUDAX-UHFFFAOYSA-N 0.000 claims 1
- CAFZJLJCRDTXIX-UHFFFAOYSA-N 6-chloro-8-(2-methylphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC=CC=C1C1=CC(Cl)=CC2=C1OC(C(F)(F)F)C(C(O)=O)=C2 CAFZJLJCRDTXIX-UHFFFAOYSA-N 0.000 claims 1
- CSMNGBNZBHIATJ-UHFFFAOYSA-N 6-chloro-8-(3-chlorophenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=CC=1C1=CC=CC(Cl)=C1 CSMNGBNZBHIATJ-UHFFFAOYSA-N 0.000 claims 1
- ZAZXZLHRIBVBQI-UHFFFAOYSA-N 6-chloro-8-(3-fluoro-4-methoxyphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(Cl)=CC2=C1OC(C(F)(F)F)C(C(O)=O)=C2 ZAZXZLHRIBVBQI-UHFFFAOYSA-N 0.000 claims 1
- CNZJJAAQDRNKDD-UHFFFAOYSA-N 6-chloro-8-(3-methylphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC=CC(C=2C=3OC(C(=CC=3C=C(Cl)C=2)C(O)=O)C(F)(F)F)=C1 CNZJJAAQDRNKDD-UHFFFAOYSA-N 0.000 claims 1
- HWEQDPYRLUBAKM-UHFFFAOYSA-N 6-chloro-8-(4-cyanophenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=CC=1C1=CC=C(C#N)C=C1 HWEQDPYRLUBAKM-UHFFFAOYSA-N 0.000 claims 1
- YHXZNEINGMVCBQ-UHFFFAOYSA-N 6-chloro-8-(4-ethoxyphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1C1=CC(Cl)=CC2=C1OC(C(F)(F)F)C(C(O)=O)=C2 YHXZNEINGMVCBQ-UHFFFAOYSA-N 0.000 claims 1
- JJWCCMOALVRLLA-UHFFFAOYSA-N 6-chloro-8-(4-fluorophenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=CC=1C1=CC=C(F)C=C1 JJWCCMOALVRLLA-UHFFFAOYSA-N 0.000 claims 1
- QZENWDHEZUJMDT-UHFFFAOYSA-N 6-chloro-8-methyl-7-(2-methylpropoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C(C)=C(OCC(C)C)C(Cl)=C2 QZENWDHEZUJMDT-UHFFFAOYSA-N 0.000 claims 1
- IAALOQVCBSWQFH-UHFFFAOYSA-N 6-methoxy-8-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(OC)=CC(C)=C21 IAALOQVCBSWQFH-UHFFFAOYSA-N 0.000 claims 1
- CXMVNVUUUNILFY-UHFFFAOYSA-N 6-methyl-7-(2-methylpropyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(CC(C)C)C(C)=C2 CXMVNVUUUNILFY-UHFFFAOYSA-N 0.000 claims 1
- IZQURNXPANKJKA-UHFFFAOYSA-N 6-naphthalen-2-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C=3C=C4C=C(C(OC4=CC=3)C(F)(F)F)C(=O)O)=CC=C21 IZQURNXPANKJKA-UHFFFAOYSA-N 0.000 claims 1
- FODPEQKNPPMJOF-UHFFFAOYSA-N 7,8-dichloro-6-methoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(OC)C(Cl)=C2Cl FODPEQKNPPMJOF-UHFFFAOYSA-N 0.000 claims 1
- IUUVZBLXCXCJOP-UHFFFAOYSA-N 7-(1-phenylethenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=C1C(=C)C1=CC=CC=C1 IUUVZBLXCXCJOP-UHFFFAOYSA-N 0.000 claims 1
- IJSBTMFGKZYHJZ-UHFFFAOYSA-N 7-(1-phenylethyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2C=C(C(O)=O)C(C(F)(F)F)OC2=CC=1C(C)C1=CC=CC=C1 IJSBTMFGKZYHJZ-UHFFFAOYSA-N 0.000 claims 1
- DSQDYLPFCKDMBZ-UHFFFAOYSA-N 7-(2,3-dimethoxyphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound COC1=CC=CC(OC=2C=C3OC(C(=CC3=CC=2)C(O)=O)C(F)(F)F)=C1OC DSQDYLPFCKDMBZ-UHFFFAOYSA-N 0.000 claims 1
- IKDDVGXJERGHKP-UHFFFAOYSA-N 7-(2,4-difluorophenoxy)-8-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC=2C=C(C(O)=O)C(C(F)(F)F)OC=2C(C)=C1OC1=CC=C(F)C=C1F IKDDVGXJERGHKP-UHFFFAOYSA-N 0.000 claims 1
- HZSIPWDORMOYQT-UHFFFAOYSA-N 7-(2,5-difluorophenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=C1OC1=CC(F)=CC=C1F HZSIPWDORMOYQT-UHFFFAOYSA-N 0.000 claims 1
- JVMMIJIJJKHTQH-UHFFFAOYSA-N 7-(2,6-dimethoxyphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound COC1=CC=CC(OC)=C1OC1=CC=C(C=C(C(O2)C(F)(F)F)C(O)=O)C2=C1 JVMMIJIJJKHTQH-UHFFFAOYSA-N 0.000 claims 1
- QNCLRZRARMGMEA-UHFFFAOYSA-N 7-(2-bromo-4,5-difluorophenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=C1OC1=CC(F)=C(F)C=C1Br QNCLRZRARMGMEA-UHFFFAOYSA-N 0.000 claims 1
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- RULRROAGINKLKK-UHFFFAOYSA-N 7-(2-chloro-4-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC(C)=CC=C1OC1=CC=C(C=C(C(O2)C(F)(F)F)C(O)=O)C2=C1 RULRROAGINKLKK-UHFFFAOYSA-N 0.000 claims 1
- SBEGPDUCBDZSOB-UHFFFAOYSA-N 7-(2-fluoro-5-methylphenoxy)-8-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC=C(F)C(OC=2C(=C3OC(C(=CC3=CC=2)C(O)=O)C(F)(F)F)C)=C1 SBEGPDUCBDZSOB-UHFFFAOYSA-N 0.000 claims 1
- LEXGAUGBPZLQIT-UHFFFAOYSA-N 7-(2-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC=CC=C1OC1=CC=C(C=C(C(O2)C(F)(F)F)C(O)=O)C2=C1 LEXGAUGBPZLQIT-UHFFFAOYSA-N 0.000 claims 1
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- MHIAIRLZVKWAGN-UHFFFAOYSA-N 7-(4-ethylphenyl)-6-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(CC)=CC=C1C(C(=C1)C)=CC2=C1C=C(C(O)=O)C(C(F)(F)F)O2 MHIAIRLZVKWAGN-UHFFFAOYSA-N 0.000 claims 1
- LVLGRBHJDNBPIF-UHFFFAOYSA-N 7-[(2-methylpropan-2-yl)oxy]-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=CC(OC(C)(C)C)=CC=C21 LVLGRBHJDNBPIF-UHFFFAOYSA-N 0.000 claims 1
- DHBOOPLKYQPFDV-UHFFFAOYSA-N 7-[(4-chlorophenyl)methyl]-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=C1CC1=CC=C(Cl)C=C1 DHBOOPLKYQPFDV-UHFFFAOYSA-N 0.000 claims 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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US45921503P | 2003-03-31 | 2003-03-31 |
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ZA200506551B true ZA200506551B (en) | 2006-11-29 |
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ZA200506551A ZA200506551B (en) | 2003-03-31 | 2005-08-16 | Benzopyran compounds useful for treating inflammatory conditions |
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JP (1) | JP2006522098A (es) |
KR (1) | KR20060015490A (es) |
CN (1) | CN1768050A (es) |
AR (1) | AR044207A1 (es) |
AU (1) | AU2004226164A1 (es) |
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TW (1) | TWI257927B (es) |
UY (1) | UY28252A1 (es) |
WO (1) | WO2004087686A2 (es) |
ZA (1) | ZA200506551B (es) |
Families Citing this family (24)
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US6034256A (en) * | 1997-04-21 | 2000-03-07 | G.D. Searle & Co. | Substituted benzopyran derivatives for the treatment of inflammation |
WO2006011052A1 (en) * | 2004-07-23 | 2006-02-02 | Pharmacia & Upjohn Company Llc | Method for the racemization of 2-trifluoro-2h-chromene-3-carboxylic acids |
BRPI0512251A (pt) * | 2004-07-23 | 2008-02-19 | Pharmacia & Upjohn Co Llc | método enantioseletivo para separação de derivados do ácido 2-trifluormetil-2h-cromeno-3-carboxìlico substituìdo |
JP2008507501A (ja) * | 2004-07-23 | 2008-03-13 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 2−トリフルオロメチル−2h−クロメン−3−カルボン酸誘導体の光ラセミ化 |
EP1792887A1 (en) * | 2005-12-05 | 2007-06-06 | Laboratorios Del Dr. Esteve, S.A. | Process for the homogeneous hydrogenation of ketones using ruthenium catalytic systems |
EP2234486A4 (en) * | 2007-12-19 | 2011-09-14 | Scripps Research Inst | BENZIMIDAZOLE AND ANALOGUE AS RHO-KINASEHEMMER |
CA2709918A1 (en) * | 2007-12-21 | 2009-06-25 | The Scripps Research Institute | Benzopyrans and analogs as rho kinase inhibitors |
US20110038835A1 (en) * | 2007-12-21 | 2011-02-17 | The Scripps Research Institute | Anilides and analogs as rho kinase inhibitors |
CN102757417B (zh) * | 2012-06-18 | 2014-09-24 | 中国科学院广州生物医药与健康研究院 | 氘代苯并吡喃类化合物及其应用 |
CN103012350B (zh) * | 2012-12-07 | 2015-02-04 | 中国科学院广州生物医药与健康研究院 | 苯并吡喃类手性化合物的合成方法 |
EP2860177A3 (en) * | 2013-09-20 | 2015-06-10 | Bayer Intellectual Property GmbH | Synthesis of functionalized arenes |
WO2015047113A1 (en) * | 2013-09-30 | 2015-04-02 | Polfarmex S.A. | Novel substituted n, n-dimethylaminoalkyl ethers of isoflavanone oximes as η1-receptor antagonists |
US9630896B2 (en) | 2013-11-22 | 2017-04-25 | Tansna Therapeutics, Inc. | 2,5-dialkyl-4-H/halo/ether-phenol compounds |
CN106102747A (zh) * | 2014-01-14 | 2016-11-09 | 欧利瑟斯制药公司 | 释放no的硝基氧基‑色烯结合物 |
GB2536650A (en) | 2015-03-24 | 2016-09-28 | Augmedics Ltd | Method and system for combining video-based and optic-based augmented reality in a near eye display |
GB2543550A (en) | 2015-10-21 | 2017-04-26 | Hox Therapeutics Ltd | Peptides |
CN107868069A (zh) * | 2017-10-31 | 2018-04-03 | 山东新华制药股份有限公司 | 7‑羟基‑8‑甲基‑6‑硝基‑2‑氧‑2h‑苯并吡喃‑3‑羧酸的制备工艺 |
EP3787543A4 (en) | 2018-05-02 | 2022-01-19 | Augmedics Ltd. | REGISTRATION OF A REFERENCE MARK FOR AN AUGMENTED REALITY SYSTEM |
CN109020990A (zh) * | 2018-09-20 | 2018-12-18 | 广西壮族自治区药用植物园 | 苯基苯并呋喃化合物、及其制备方法、组合物和医药用途 |
US11766296B2 (en) | 2018-11-26 | 2023-09-26 | Augmedics Ltd. | Tracking system for image-guided surgery |
US11980506B2 (en) | 2019-07-29 | 2024-05-14 | Augmedics Ltd. | Fiducial marker |
US11382712B2 (en) | 2019-12-22 | 2022-07-12 | Augmedics Ltd. | Mirroring in image guided surgery |
US11896445B2 (en) | 2021-07-07 | 2024-02-13 | Augmedics Ltd. | Iliac pin and adapter |
WO2023012081A1 (en) | 2021-08-05 | 2023-02-09 | Syngenta Crop Protection Ag | Method for controlling diamide resistant pests & compounds therefor |
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US3794734A (en) | 1971-03-03 | 1974-02-26 | Merck & Co Inc | Methods of treating edema and hypertension using certain 2-aminoethylphenols |
US6034256A (en) | 1997-04-21 | 2000-03-07 | G.D. Searle & Co. | Substituted benzopyran derivatives for the treatment of inflammation |
US6077850A (en) | 1997-04-21 | 2000-06-20 | G.D. Searle & Co. | Substituted benzopyran analogs for the treatment of inflammation |
US6649645B1 (en) | 1998-12-23 | 2003-11-18 | Pharmacia Corporation | Combination therapy of radiation and a COX-2 inhibitor for treatment of neoplasia |
US20030153801A1 (en) | 2001-05-29 | 2003-08-14 | Pharmacia Corporation | Compositions of cyclooxygenase-2 selective inhibitors and radiation for inhibition or prevention of cardiovascular disease |
US6620871B2 (en) * | 2001-06-07 | 2003-09-16 | Nike, Inc. | Rubber compositions with increased shelf life and reduced cure temperatures and times |
US20030114418A1 (en) * | 2001-08-14 | 2003-06-19 | Pharmacia Corporation | Method for the treatment and prevention of pain and inflammation with glucosamine and a cyclooxygenase-2 selective inhibitor and compositions therefor |
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- 2004-03-26 AU AU2004226164A patent/AU2004226164A1/en not_active Abandoned
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- 2004-03-26 RS YUP-2005/0744A patent/RS20050744A/sr unknown
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- 2004-03-29 NL NL1025843A patent/NL1025843C2/nl not_active IP Right Cessation
- 2004-03-30 AR ARP040101056A patent/AR044207A1/es unknown
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- 2004-03-31 PA PA20048599601A patent/PA8599601A1/es unknown
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- 2005-08-16 ZA ZA200506551A patent/ZA200506551B/en unknown
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- 2005-09-29 EC EC2005006063A patent/ECSP056063A/es unknown
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- 2005-09-30 TN TNP2005000249A patent/TNSN05249A1/fr unknown
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