OA13112A - Benzopyran compounds useful for treating inflammatory conditions. - Google Patents
Benzopyran compounds useful for treating inflammatory conditions. Download PDFInfo
- Publication number
- OA13112A OA13112A OA1200500270A OA1200500270A OA13112A OA 13112 A OA13112 A OA 13112A OA 1200500270 A OA1200500270 A OA 1200500270A OA 1200500270 A OA1200500270 A OA 1200500270A OA 13112 A OA13112 A OA 13112A
- Authority
- OA
- OAPI
- Prior art keywords
- chromene
- trifluoromethyl
- carboxylic acid
- chloro
- methyl
- Prior art date
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- 150000001562 benzopyrans Chemical class 0.000 title abstract description 6
- 230000004968 inflammatory condition Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 239000002253 acid Substances 0.000 claims description 178
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 138
- 239000011734 sodium Substances 0.000 claims description 111
- 229910052708 sodium Inorganic materials 0.000 claims description 104
- 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 100
- -1 8-chloro-6-(hexyloxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic 8-chloro-6-propoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid Chemical compound 0.000 claims description 84
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 81
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 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 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000007942 carboxylates Chemical class 0.000 claims description 7
- DNSZVRYSOQVHKS-NSHDSACASA-N (2s)-8-ethyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)[C@@H](C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2CC DNSZVRYSOQVHKS-NSHDSACASA-N 0.000 claims description 6
- DNSZVRYSOQVHKS-UHFFFAOYSA-N 8-ethyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2CC DNSZVRYSOQVHKS-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 claims description 5
- AXLIJRCKRUPBPQ-LLVKDONJSA-N (2r)-6,8-dimethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@@H](C(F)(F)F)C(C(O)=O)=CC2=CC(C)=CC(C)=C21 AXLIJRCKRUPBPQ-LLVKDONJSA-N 0.000 claims description 5
- 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 description 5
- AXLIJRCKRUPBPQ-NSHDSACASA-N (2s)-6,8-dimethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@H](C(F)(F)F)C(C(O)=O)=CC2=CC(C)=CC(C)=C21 AXLIJRCKRUPBPQ-NSHDSACASA-N 0.000 claims description 5
- 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 description 5
- 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 description 5
- MSOFWRSBKHPVFU-MERQFXBCSA-M sodium;(2s)-6-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].O1[C@H](C(F)(F)F)C(C([O-])=O)=CC2=CC(CC)=CC=C21 MSOFWRSBKHPVFU-MERQFXBCSA-M 0.000 claims description 5
- VFGSNLRSCYUGNT-UHFFFAOYSA-N 6-chloro-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(Cl)=C2 VFGSNLRSCYUGNT-UHFFFAOYSA-N 0.000 claims description 4
- YBUPKAFNJNXZCU-UHFFFAOYSA-N 6-chloro-7-(2-methylpropylsulfanyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(SCC(C)C)C(Cl)=C2 YBUPKAFNJNXZCU-UHFFFAOYSA-N 0.000 claims description 4
- ZWVRCFFNZGTFHO-UHFFFAOYSA-N 6-chloro-8-methyl-7-(3-methylbutoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C(C)=C(OCCC(C)C)C(Cl)=C2 ZWVRCFFNZGTFHO-UHFFFAOYSA-N 0.000 claims description 4
- MPXRLCGCENHTGO-UHFFFAOYSA-N 7-benzyl-6-bromo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Br)=C1CC1=CC=CC=C1 MPXRLCGCENHTGO-UHFFFAOYSA-N 0.000 claims description 4
- COVFGUVDMKXLIL-UHFFFAOYSA-N 7-benzyl-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=C1CC1=CC=CC=C1 COVFGUVDMKXLIL-UHFFFAOYSA-N 0.000 claims description 4
- VZNMBSLLLMBKED-UHFFFAOYSA-N 7-butylsulfanyl-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(SCCCC)C(Cl)=C2 VZNMBSLLLMBKED-UHFFFAOYSA-N 0.000 claims description 4
- AGHSPMXNECAAHA-UHFFFAOYSA-N 8-chloro-6-iodo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound IC1=CC(Cl)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 AGHSPMXNECAAHA-UHFFFAOYSA-N 0.000 claims description 4
- VNNFYDMOBSMMIL-UHFFFAOYSA-N 8-ethoxy-6-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(C)C=C2OCC VNNFYDMOBSMMIL-UHFFFAOYSA-N 0.000 claims description 4
- AONVHSNFWRCPOZ-UHFFFAOYSA-N 8-pentyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2CCCCC AONVHSNFWRCPOZ-UHFFFAOYSA-N 0.000 claims description 4
- IOGQYPXEPFSTAB-UHFFFAOYSA-N 8-prop-1-ynyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2C#CC IOGQYPXEPFSTAB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- FCYUPOCBNOAMHF-HFEGYEGKSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)c1ccccc1.C[C@@H](N)c1ccccc1 FCYUPOCBNOAMHF-HFEGYEGKSA-N 0.000 claims description 3
- DNSZVRYSOQVHKS-LLVKDONJSA-N (2r)-8-ethyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)[C@H](C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2CC DNSZVRYSOQVHKS-LLVKDONJSA-N 0.000 claims description 3
- WBAUJPYWZXLTGY-NSHDSACASA-N (2s)-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-NSHDSACASA-N 0.000 claims description 3
- QOHGXWIDSHOGBZ-LBPRGKRZSA-N (2s)-6-ethyl-8-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@H](C(F)(F)F)C(C(O)=O)=CC2=CC(CC)=CC(C)=C21 QOHGXWIDSHOGBZ-LBPRGKRZSA-N 0.000 claims description 3
- COVFGUVDMKXLIL-INIZCTEOSA-N (2s)-7-benzyl-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound OC(=O)C([C@H](OC1=C2)C(F)(F)F)=CC1=CC(Cl)=C2CC1=CC=CC=C1 COVFGUVDMKXLIL-INIZCTEOSA-N 0.000 claims description 3
- LQDWDWIVELMUIM-UHFFFAOYSA-N 5-chloro-6,8-dimethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C(Cl)C(C)=CC(C)=C21 LQDWDWIVELMUIM-UHFFFAOYSA-N 0.000 claims description 3
- KGAULISDWPKWLK-UHFFFAOYSA-N 5-chloro-8-(2-ethylbutoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C(Cl)=CC=C2OCC(CC)CC KGAULISDWPKWLK-UHFFFAOYSA-N 0.000 claims description 3
- UNVRDOQJZJZLFQ-UHFFFAOYSA-N 5-chloro-8-methoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C(Cl)=CC=C2OC UNVRDOQJZJZLFQ-UHFFFAOYSA-N 0.000 claims description 3
- VZJKMDJGGAPBEY-UHFFFAOYSA-N 5-chloro-8-propoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C(Cl)=CC=C2OCCC VZJKMDJGGAPBEY-UHFFFAOYSA-N 0.000 claims description 3
- DJWRLCCYQDDNIG-UHFFFAOYSA-N 6,8-diethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(CC)=CC(CC)=C21 DJWRLCCYQDDNIG-UHFFFAOYSA-N 0.000 claims description 3
- NBSGNUBPYGSDAL-UHFFFAOYSA-N 6-chloro-7-(2,2-dimethylpropoxy)-8-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C(OCC(C)(C)C)=C2C NBSGNUBPYGSDAL-UHFFFAOYSA-N 0.000 claims description 3
- NGFRFQNUVNOMKR-UHFFFAOYSA-N 6-chloro-7-(2-ethylbutoxy)-8-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C(C)=C(OCC(CC)CC)C(Cl)=C2 NGFRFQNUVNOMKR-UHFFFAOYSA-N 0.000 claims description 3
- VONFPCZKBNGLDW-UHFFFAOYSA-N 6-chloro-7-[(2-ethylphenyl)methyl]-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CCC1=CC=CC=C1CC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)C(C(F)(F)F)O2 VONFPCZKBNGLDW-UHFFFAOYSA-N 0.000 claims description 3
- BRLUSSFDDMNMRT-UHFFFAOYSA-N 6-chloro-7-[(2-methoxyphenyl)methyl]-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound COC1=CC=CC=C1CC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)C(C(F)(F)F)O2 BRLUSSFDDMNMRT-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 description 3
- SMIWSYRJFFWLFP-UHFFFAOYSA-N 7-(furan-2-ylmethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=C1OCC1=CC=CO1 SMIWSYRJFFWLFP-UHFFFAOYSA-N 0.000 claims description 3
- QLRWMFMQLKMZJN-UHFFFAOYSA-N 7-benzyl-6-chloro-8-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC=2C=C(C(O)=O)C(C(F)(F)F)OC=2C(C)=C1CC1=CC=CC=C1 QLRWMFMQLKMZJN-UHFFFAOYSA-N 0.000 claims description 3
- DTCXZIHWKMXNQT-UHFFFAOYSA-N 7-benzyl-6-propyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CCCC1=CC=2C=C(C(O)=O)C(C(F)(F)F)OC=2C=C1CC1=CC=CC=C1 DTCXZIHWKMXNQT-UHFFFAOYSA-N 0.000 claims description 3
- ZMMBZOKXHUHVND-UHFFFAOYSA-N 8-but-1-ynyl-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C=C2C#CCC ZMMBZOKXHUHVND-UHFFFAOYSA-N 0.000 claims description 3
- JOBQMBHNCXPGBC-UHFFFAOYSA-N 8-methyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2C JOBQMBHNCXPGBC-UHFFFAOYSA-N 0.000 claims description 3
- CBIICNPXTGZWSQ-UHFFFAOYSA-N 8-pent-1-ynyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2C#CCCC CBIICNPXTGZWSQ-UHFFFAOYSA-N 0.000 claims description 3
- BAPOZHZZQCVIOR-UHFFFAOYSA-N 8-propoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=CC=C2OCCC BAPOZHZZQCVIOR-UHFFFAOYSA-N 0.000 claims description 3
- QMYWVIUWYGXZGG-PPHPATTJSA-M sodium;(2s)-8-chloro-6-methoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].O1[C@H](C(F)(F)F)C(C([O-])=O)=CC2=CC(OC)=CC(Cl)=C21 QMYWVIUWYGXZGG-PPHPATTJSA-M 0.000 claims description 3
- GNXDAIHBUPCRBG-UHFFFAOYSA-M sodium;6-chloro-7-(2-methylpropyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].O1C(C(F)(F)F)C(C([O-])=O)=CC2=C1C=C(CC(C)C)C(Cl)=C2 GNXDAIHBUPCRBG-UHFFFAOYSA-M 0.000 claims description 3
- BJDPAXUDDAUMAG-UHFFFAOYSA-M sodium;8-propyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].C1=C(C([O-])=O)C(C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2CCC BJDPAXUDDAUMAG-UHFFFAOYSA-M 0.000 claims description 3
- IDFHCDIRYRPEOQ-LLVKDONJSA-N (2r)-6-chloro-7,8-dimethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@@H](C(F)(F)F)C(C(O)=O)=CC2=C1C(C)=C(C)C(Cl)=C2 IDFHCDIRYRPEOQ-LLVKDONJSA-N 0.000 claims description 2
- VFGSNLRSCYUGNT-CYBMUJFWSA-N (2r)-6-chloro-7-(2-methylpropyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@@H](C(F)(F)F)C(C(O)=O)=CC2=C1C=C(CC(C)C)C(Cl)=C2 VFGSNLRSCYUGNT-CYBMUJFWSA-N 0.000 claims description 2
- IWMDNSVRPSGOFO-MRXNPFEDSA-N (2r)-6-chloro-7-(4-chloro-2-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC(Cl)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@H](C(F)(F)F)O2 IWMDNSVRPSGOFO-MRXNPFEDSA-N 0.000 claims description 2
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- WJZABKBEIUCOHS-MERQFXBCSA-M [Na+].C1=C(C([O-])=O)[C@@H](C(F)(F)F)OC2=C(C)C(C)=C(Cl)C=C21 Chemical compound [Na+].C1=C(C([O-])=O)[C@@H](C(F)(F)F)OC2=C(C)C(C)=C(Cl)C=C21 WJZABKBEIUCOHS-MERQFXBCSA-M 0.000 claims description 2
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- BZYQNPYYMBHCOO-UHFFFAOYSA-M sodium;6-chloro-5-phenoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].O1C(C(F)(F)F)C(C(=O)[O-])=CC2=C1C=CC(Cl)=C2OC1=CC=CC=C1 BZYQNPYYMBHCOO-UHFFFAOYSA-M 0.000 claims description 2
- GPHZFSQQCLIMOM-UHFFFAOYSA-M sodium;6-chloro-7-(2-methylpropylamino)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].O1C(C(F)(F)F)C(C([O-])=O)=CC2=C1C=C(NCC(C)C)C(Cl)=C2 GPHZFSQQCLIMOM-UHFFFAOYSA-M 0.000 claims description 2
- BFZJZGKWMRVDDL-UHFFFAOYSA-M sodium;6-chloro-7-(2-methylpropylsulfanyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].O1C(C(F)(F)F)C(C([O-])=O)=CC2=C1C=C(SCC(C)C)C(Cl)=C2 BFZJZGKWMRVDDL-UHFFFAOYSA-M 0.000 claims description 2
- IYOXGTCHOHPTBN-UHFFFAOYSA-M sodium;6-chloro-7-(2-propylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].CCCC1=CC=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C([O-])=O)C(C(F)(F)F)O2 IYOXGTCHOHPTBN-UHFFFAOYSA-M 0.000 claims description 2
- ZYJVRWAYSVHGLF-UHFFFAOYSA-M sodium;6-chloro-7-[(4-chlorophenyl)methyl]-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].C1=C2OC(C(F)(F)F)C(C(=O)[O-])=CC2=CC(Cl)=C1CC1=CC=C(Cl)C=C1 ZYJVRWAYSVHGLF-UHFFFAOYSA-M 0.000 claims description 2
- KDYOSEMCCRSHNA-UHFFFAOYSA-M sodium;6-chloro-8-(3-fluoro-4-methylphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].C1=C(F)C(C)=CC=C1C1=CC(Cl)=CC2=C1OC(C(F)(F)F)C(C([O-])=O)=C2 KDYOSEMCCRSHNA-UHFFFAOYSA-M 0.000 claims description 2
- FOSKBRUVNBPIKB-UHFFFAOYSA-M sodium;6-chloro-8-(4-chloro-3-methylphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].C1=C(Cl)C(C)=CC(C=2C=3OC(C(=CC=3C=C(Cl)C=2)C([O-])=O)C(F)(F)F)=C1 FOSKBRUVNBPIKB-UHFFFAOYSA-M 0.000 claims description 2
- MSOFWRSBKHPVFU-UHFFFAOYSA-M sodium;6-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].O1C(C(F)(F)F)C(C([O-])=O)=CC2=CC(CC)=CC=C21 MSOFWRSBKHPVFU-UHFFFAOYSA-M 0.000 claims description 2
- CGKIWFJVAYYTGH-UHFFFAOYSA-M sodium;6-ethyl-7-methoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].C1=C(C([O-])=O)C(C(F)(F)F)OC2=C1C=C(CC)C(OC)=C2 CGKIWFJVAYYTGH-UHFFFAOYSA-M 0.000 claims description 2
- AKCCBSZBEQACGF-UHFFFAOYSA-M sodium;7-(2,5-dimethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].CC1=CC=C(C)C(OC=2C=C3OC(C(=CC3=CC=2)C([O-])=O)C(F)(F)F)=C1 AKCCBSZBEQACGF-UHFFFAOYSA-M 0.000 claims description 2
- SKDMMZVTWKMPPM-UHFFFAOYSA-M sodium;7-(4-ethylphenoxy)-8-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].C1=CC(CC)=CC=C1OC1=CC=C(C=C(C(O2)C(F)(F)F)C([O-])=O)C2=C1C SKDMMZVTWKMPPM-UHFFFAOYSA-M 0.000 claims description 2
- WEQQFPNHKXNZTP-UHFFFAOYSA-M sodium;8-(2-phenylethyl)-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].C=12OC(C(F)(F)F)C(C(=O)[O-])=CC2=CC(OC(F)(F)F)=CC=1CCC1=CC=CC=C1 WEQQFPNHKXNZTP-UHFFFAOYSA-M 0.000 claims description 2
- XGSGQDRZXZOXAL-NSHDSACASA-N (2s)-8-chloro-6-ethynyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C#CC1=CC(Cl)=C2O[C@H](C(F)(F)F)C(C(=O)O)=CC2=C1 XGSGQDRZXZOXAL-NSHDSACASA-N 0.000 claims 2
- NSNFTKQPJDLMHU-UHFFFAOYSA-N 6-chloro-7-[(2-methylphenyl)methyl]-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC=CC=C1CC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)C(C(F)(F)F)O2 NSNFTKQPJDLMHU-UHFFFAOYSA-N 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
- YXCGPWHFMNJOQR-BSGLVDAKSA-N (2R)-6-chloro-5,7-dimethyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid Chemical compound Cc1cc2O[C@H](C(=Cc2c(C)c1Cl)C(O)=O)C(F)(F)F.Cc1cc2O[C@H](C(=Cc2c(C)c1Cl)C(O)=O)C(F)(F)F YXCGPWHFMNJOQR-BSGLVDAKSA-N 0.000 claims 1
- ARPMFJUTCMMLRA-GOSISDBHSA-N (2r)-2-(trifluoromethyl)-7-(2,3,5-trimethylphenoxy)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC(C)=C(C)C(OC=2C=C3O[C@H](C(=CC3=CC=2)C(O)=O)C(F)(F)F)=C1 ARPMFJUTCMMLRA-GOSISDBHSA-N 0.000 claims 1
- YRMJMVYWDMTICE-OAHLLOKOSA-N (2r)-5-phenoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound OC(=O)C([C@@H](OC1=CC=C2)C(F)(F)F)=CC1=C2OC1=CC=CC=C1 YRMJMVYWDMTICE-OAHLLOKOSA-N 0.000 claims 1
- DJWRLCCYQDDNIG-CYBMUJFWSA-N (2r)-6,8-diethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@@H](C(F)(F)F)C(C(O)=O)=CC2=CC(CC)=CC(CC)=C21 DJWRLCCYQDDNIG-CYBMUJFWSA-N 0.000 claims 1
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- ZHRMSIDYCXFKFH-SNVBAGLBSA-N (2r)-6-chloro-5-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@@H](C(F)(F)F)C(C(O)=O)=CC2=C1C=CC(Cl)=C2C ZHRMSIDYCXFKFH-SNVBAGLBSA-N 0.000 claims 1
- ZQQZDCYBJJAOQW-CYBMUJFWSA-N (2r)-6-chloro-5-methyl-8-propan-2-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)[C@H](C(F)(F)F)OC2=C1C(C)=C(Cl)C=C2C(C)C ZQQZDCYBJJAOQW-CYBMUJFWSA-N 0.000 claims 1
- HVQDIKGNRQZLDX-OAHLLOKOSA-N (2r)-6-chloro-5-phenoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound OC(=O)C([C@@H](O1)C(F)(F)F)=CC2=C1C=CC(Cl)=C2OC1=CC=CC=C1 HVQDIKGNRQZLDX-OAHLLOKOSA-N 0.000 claims 1
- GYXHDOLLCMTPRM-QGZVFWFLSA-N (2r)-6-chloro-7-(2,4-dimethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC(C)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@H](C(F)(F)F)O2 GYXHDOLLCMTPRM-QGZVFWFLSA-N 0.000 claims 1
- CWQKFBAEQAGBMM-QGZVFWFLSA-N (2r)-6-chloro-7-(2-chloro-4,5-dimethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C)C(C)=CC(Cl)=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@H](C(F)(F)F)O2 CWQKFBAEQAGBMM-QGZVFWFLSA-N 0.000 claims 1
- WSZYPZWXKAONOK-MRXNPFEDSA-N (2r)-6-chloro-7-(2-chloro-4-methoxyphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC(OC)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@H](C(F)(F)F)O2 WSZYPZWXKAONOK-MRXNPFEDSA-N 0.000 claims 1
- HVLOIJZKHZBNPW-QGZVFWFLSA-N (2r)-6-chloro-7-(2-methoxy-4-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound COC1=CC(C)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@H](C(F)(F)F)O2 HVLOIJZKHZBNPW-QGZVFWFLSA-N 0.000 claims 1
- FHQQYIRXSZICFG-MRXNPFEDSA-N (2r)-6-chloro-7-(2-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@H](C(F)(F)F)O2 FHQQYIRXSZICFG-MRXNPFEDSA-N 0.000 claims 1
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- LZQQOLXALYJOGD-QGZVFWFLSA-N (2r)-6-chloro-7-(4-ethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(CC)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@H](C(F)(F)F)O2 LZQQOLXALYJOGD-QGZVFWFLSA-N 0.000 claims 1
- CZLQYZOKSBXYJE-MRXNPFEDSA-N (2r)-6-chloro-7-(4-fluoro-2-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC(F)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@H](C(F)(F)F)O2 CZLQYZOKSBXYJE-MRXNPFEDSA-N 0.000 claims 1
- NTNQMVISBBFDRT-CQSZACIVSA-N (2r)-6-chloro-7-[methyl(2-methylpropyl)amino]-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@@H](C(F)(F)F)C(C(O)=O)=CC2=C1C=C(N(C)CC(C)C)C(Cl)=C2 NTNQMVISBBFDRT-CQSZACIVSA-N 0.000 claims 1
- RQDPUQLFTORJPW-QGZVFWFLSA-N (2r)-7-(2,5-dimethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC=C(C)C(OC=2C=C3O[C@H](C(=CC3=CC=2)C(O)=O)C(F)(F)F)=C1 RQDPUQLFTORJPW-QGZVFWFLSA-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
- XGSGQDRZXZOXAL-LLVKDONJSA-N (2r)-8-chloro-6-ethynyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C#CC1=CC(Cl)=C2O[C@@H](C(F)(F)F)C(C(=O)O)=CC2=C1 XGSGQDRZXZOXAL-LLVKDONJSA-N 0.000 claims 1
- JOBQMBHNCXPGBC-SNVBAGLBSA-N (2r)-8-methyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)[C@H](C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2C JOBQMBHNCXPGBC-SNVBAGLBSA-N 0.000 claims 1
- AEIGTKUKBWYPFQ-GFCCVEGCSA-N (2r)-8-propyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)[C@H](C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2CCC AEIGTKUKBWYPFQ-GFCCVEGCSA-N 0.000 claims 1
- ARPMFJUTCMMLRA-SFHVURJKSA-N (2s)-2-(trifluoromethyl)-7-(2,3,5-trimethylphenoxy)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC(C)=C(C)C(OC=2C=C3O[C@@H](C(=CC3=CC=2)C(O)=O)C(F)(F)F)=C1 ARPMFJUTCMMLRA-SFHVURJKSA-N 0.000 claims 1
- FQKMILFVTQADHR-ZDUSSCGKSA-N (2s)-6,8-dichloro-7-(2-methylpropoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)[C@@H](C(F)(F)F)OC2=C(Cl)C(OCC(C)C)=C(Cl)C=C21 FQKMILFVTQADHR-ZDUSSCGKSA-N 0.000 claims 1
- ZHRMSIDYCXFKFH-JTQLQIEISA-N (2s)-6-chloro-5-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@H](C(F)(F)F)C(C(O)=O)=CC2=C1C=CC(Cl)=C2C ZHRMSIDYCXFKFH-JTQLQIEISA-N 0.000 claims 1
- HVQDIKGNRQZLDX-HNNXBMFYSA-N (2s)-6-chloro-5-phenoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound OC(=O)C([C@H](O1)C(F)(F)F)=CC2=C1C=CC(Cl)=C2OC1=CC=CC=C1 HVQDIKGNRQZLDX-HNNXBMFYSA-N 0.000 claims 1
- IDFHCDIRYRPEOQ-NSHDSACASA-N (2s)-6-chloro-7,8-dimethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@H](C(F)(F)F)C(C(O)=O)=CC2=C1C(C)=C(C)C(Cl)=C2 IDFHCDIRYRPEOQ-NSHDSACASA-N 0.000 claims 1
- GYXHDOLLCMTPRM-KRWDZBQOSA-N (2s)-6-chloro-7-(2,4-dimethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC(C)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@@H](C(F)(F)F)O2 GYXHDOLLCMTPRM-KRWDZBQOSA-N 0.000 claims 1
- CWQKFBAEQAGBMM-KRWDZBQOSA-N (2s)-6-chloro-7-(2-chloro-4,5-dimethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C)C(C)=CC(Cl)=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@@H](C(F)(F)F)O2 CWQKFBAEQAGBMM-KRWDZBQOSA-N 0.000 claims 1
- BQLIYSXMPQKINO-INIZCTEOSA-N (2s)-6-chloro-7-(2-chloro-4-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC(C)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@@H](C(F)(F)F)O2 BQLIYSXMPQKINO-INIZCTEOSA-N 0.000 claims 1
- FHQQYIRXSZICFG-INIZCTEOSA-N (2s)-6-chloro-7-(2-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@@H](C(F)(F)F)O2 FHQQYIRXSZICFG-INIZCTEOSA-N 0.000 claims 1
- YBUPKAFNJNXZCU-ZDUSSCGKSA-N (2s)-6-chloro-7-(2-methylpropylsulfanyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@H](C(F)(F)F)C(C(O)=O)=CC2=C1C=C(SCC(C)C)C(Cl)=C2 YBUPKAFNJNXZCU-ZDUSSCGKSA-N 0.000 claims 1
- LZQQOLXALYJOGD-KRWDZBQOSA-N (2s)-6-chloro-7-(4-ethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(CC)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@@H](C(F)(F)F)O2 LZQQOLXALYJOGD-KRWDZBQOSA-N 0.000 claims 1
- CZLQYZOKSBXYJE-INIZCTEOSA-N (2s)-6-chloro-7-(4-fluoro-2-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC(F)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@@H](C(F)(F)F)O2 CZLQYZOKSBXYJE-INIZCTEOSA-N 0.000 claims 1
- WUTZITHRJNTBRE-INIZCTEOSA-N (2s)-6-chloro-7-(4-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)[C@@H](C(F)(F)F)O2 WUTZITHRJNTBRE-INIZCTEOSA-N 0.000 claims 1
- SVSFRUVDCJWHOW-INIZCTEOSA-N (2s)-6-chloro-8-(3-fluoro-4-methylphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(F)C(C)=CC=C1C1=CC(Cl)=CC2=C1O[C@H](C(F)(F)F)C(C(O)=O)=C2 SVSFRUVDCJWHOW-INIZCTEOSA-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
- FKRGMKAZITYKGR-INIZCTEOSA-N (2s)-6-chloro-8-(4-methylphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CC(Cl)=CC2=C1O[C@H](C(F)(F)F)C(C(O)=O)=C2 FKRGMKAZITYKGR-INIZCTEOSA-N 0.000 claims 1
- ZWVRCFFNZGTFHO-HNNXBMFYSA-N (2s)-6-chloro-8-methyl-7-(3-methylbutoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1[C@H](C(F)(F)F)C(C(O)=O)=CC2=C1C(C)=C(OCCC(C)C)C(Cl)=C2 ZWVRCFFNZGTFHO-HNNXBMFYSA-N 0.000 claims 1
- AEIGTKUKBWYPFQ-LBPRGKRZSA-N (2s)-8-propyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)[C@@H](C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2CCC AEIGTKUKBWYPFQ-LBPRGKRZSA-N 0.000 claims 1
- KASQQNRZFUINIK-UHFFFAOYSA-N 2-(trifluoromethyl)-5-(2,3,5-trimethylphenoxy)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC(C)=C(C)C(OC=2C=3C=C(C(OC=3C=CC=2)C(F)(F)F)C(O)=O)=C1 KASQQNRZFUINIK-UHFFFAOYSA-N 0.000 claims 1
- XDIKQYOEBBAVKQ-UHFFFAOYSA-N 2-(trifluoromethyl)-6-[3-(trifluoromethyl)phenyl]-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1C1=CC=CC(C(F)(F)F)=C1 XDIKQYOEBBAVKQ-UHFFFAOYSA-N 0.000 claims 1
- ARPMFJUTCMMLRA-UHFFFAOYSA-N 2-(trifluoromethyl)-7-(2,3,5-trimethylphenoxy)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC(C)=C(C)C(OC=2C=C3OC(C(=CC3=CC=2)C(O)=O)C(F)(F)F)=C1 ARPMFJUTCMMLRA-UHFFFAOYSA-N 0.000 claims 1
- VWBQYZRKPRWBJV-UHFFFAOYSA-N 5,7-dichloro-6-ethoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C(Cl)C(OCC)=C(Cl)C=C21 VWBQYZRKPRWBJV-UHFFFAOYSA-N 0.000 claims 1
- HELKCTUKYBSEGG-UHFFFAOYSA-N 5,7-dimethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=CC(C)=CC(C)=C21 HELKCTUKYBSEGG-UHFFFAOYSA-N 0.000 claims 1
- ZIHOCWMAJJCJEU-UHFFFAOYSA-N 5-(2,3-dimethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC=CC(OC=2C=3C=C(C(OC=3C=CC=2)C(F)(F)F)C(O)=O)=C1C ZIHOCWMAJJCJEU-UHFFFAOYSA-N 0.000 claims 1
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- IEJVGRARHRGJQU-UHFFFAOYSA-N 8-chloro-6-phenyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C(Cl)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1C1=CC=CC=C1 IEJVGRARHRGJQU-UHFFFAOYSA-N 0.000 claims 1
- HFURVRYSXXHBBP-UHFFFAOYSA-N 8-chloro-6-pyridin-3-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C(Cl)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1C1=CC=CN=C1 HFURVRYSXXHBBP-UHFFFAOYSA-N 0.000 claims 1
- YKSRWCXPLTXGPA-UHFFFAOYSA-N 8-chloro-6-quinolin-8-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CN=C2C(C=3C=C4C=C(C(OC4=C(Cl)C=3)C(F)(F)F)C(=O)O)=CC=CC2=C1 YKSRWCXPLTXGPA-UHFFFAOYSA-N 0.000 claims 1
- CSCXVQTUOIHRHV-UHFFFAOYSA-N 8-cyano-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound FC(F)(F)OC1=CC(C#N)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 CSCXVQTUOIHRHV-UHFFFAOYSA-N 0.000 claims 1
- MPNWVURFIXZNCY-UHFFFAOYSA-N 8-ethoxy-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2OCC MPNWVURFIXZNCY-UHFFFAOYSA-N 0.000 claims 1
- XTLJTULTLMPHGK-UHFFFAOYSA-N 8-ethynyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound FC(F)(F)OC1=CC(C#C)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 XTLJTULTLMPHGK-UHFFFAOYSA-N 0.000 claims 1
- NATDILSVSZVSMG-UHFFFAOYSA-N 8-hydroxy-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound FC(F)(F)OC1=CC(O)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 NATDILSVSZVSMG-UHFFFAOYSA-N 0.000 claims 1
- KMCQUIMGGFNKOV-UHFFFAOYSA-N 8-iodo-7-methoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C(I)C(OC)=CC=C21 KMCQUIMGGFNKOV-UHFFFAOYSA-N 0.000 claims 1
- PBGRARHEVYPEOU-UHFFFAOYSA-N 8-methoxy-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2OC PBGRARHEVYPEOU-UHFFFAOYSA-N 0.000 claims 1
- PSHKYCSBPKGNMQ-UHFFFAOYSA-N 8-methyl-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=C1C PSHKYCSBPKGNMQ-UHFFFAOYSA-N 0.000 claims 1
- AKTXEXBUEFORBH-UHFFFAOYSA-N 8-methyl-7-(4-methylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1OC1=CC=C(C=C(C(O2)C(F)(F)F)C(O)=O)C2=C1C AKTXEXBUEFORBH-UHFFFAOYSA-N 0.000 claims 1
- XZMBCTAPDVHCJE-UHFFFAOYSA-N 8-methyl-7-naphthalen-1-yloxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=CC(OC=1C3=CC=CC=C3C=CC=1)=C2C XZMBCTAPDVHCJE-UHFFFAOYSA-N 0.000 claims 1
- JCNZTZGGTMDFIG-UHFFFAOYSA-N 8-phenyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC(OC(F)(F)F)=CC=1C1=CC=CC=C1 JCNZTZGGTMDFIG-UHFFFAOYSA-N 0.000 claims 1
- LDQREXIENDTGPH-UHFFFAOYSA-N 8-propan-2-yl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2C(C)C LDQREXIENDTGPH-UHFFFAOYSA-N 0.000 claims 1
- CSXPOCIXYJHQFD-UHFFFAOYSA-N 8-tert-butyl-6-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(CC)C=C2C(C)(C)C CSXPOCIXYJHQFD-UHFFFAOYSA-N 0.000 claims 1
- AWTQVAMKZLCGOR-GMUIIQOCSA-M sodium;(2r)-2-(trifluoromethyl)-7-(2,3,5-trimethylphenoxy)-2h-chromene-3-carboxylate Chemical compound [Na+].CC1=CC(C)=C(C)C(OC=2C=C3O[C@H](C(=CC3=CC=2)C([O-])=O)C(F)(F)F)=C1 AWTQVAMKZLCGOR-GMUIIQOCSA-M 0.000 claims 1
- GNXDAIHBUPCRBG-BTQNPOSSSA-M sodium;(2r)-6-chloro-7-(2-methylpropyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].O1[C@@H](C(F)(F)F)C(C([O-])=O)=CC2=C1C=C(CC(C)C)C(Cl)=C2 GNXDAIHBUPCRBG-BTQNPOSSSA-M 0.000 claims 1
- BFZJZGKWMRVDDL-BTQNPOSSSA-M sodium;(2r)-6-chloro-7-(2-methylpropylsulfanyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].O1[C@@H](C(F)(F)F)C(C([O-])=O)=CC2=C1C=C(SCC(C)C)C(Cl)=C2 BFZJZGKWMRVDDL-BTQNPOSSSA-M 0.000 claims 1
- YLSRQZUIMLQGCD-UNTBIKODSA-M sodium;(2r)-6-chloro-7-[(4-methylphenyl)methyl]-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].C1=CC(C)=CC=C1CC(C(=C1)Cl)=CC2=C1C=C(C([O-])=O)[C@H](C(F)(F)F)O2 YLSRQZUIMLQGCD-UNTBIKODSA-M 0.000 claims 1
- QQDKZJHZZWPIQE-PFEQFJNWSA-M sodium;(2r)-6-chloro-7-[methyl(2-methylpropyl)amino]-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].O1[C@@H](C(F)(F)F)C(C([O-])=O)=CC2=C1C=C(N(C)CC(C)C)C(Cl)=C2 QQDKZJHZZWPIQE-PFEQFJNWSA-M 0.000 claims 1
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- CYHGDMPWKPCXJD-RFVHGSKJSA-M sodium;(2r)-8-ethyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].C1=C(C([O-])=O)[C@H](C(F)(F)F)OC2=C1C=C(OC(F)(F)F)C=C2CC CYHGDMPWKPCXJD-RFVHGSKJSA-M 0.000 claims 1
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- OUCUZTWHKWVFNH-ZOWNYOTGSA-M sodium;(2s)-6-chloro-5-methyl-8-propan-2-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound [Na+].C1=C(C([O-])=O)[C@@H](C(F)(F)F)OC2=C1C(C)=C(Cl)C=C2C(C)C OUCUZTWHKWVFNH-ZOWNYOTGSA-M 0.000 claims 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Gastroenterology & Hepatology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Quinoline Compounds (AREA)
- Pyrane Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45921503P | 2003-03-31 | 2003-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA13112A true OA13112A (en) | 2006-11-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200500270A OA13112A (en) | 2003-03-31 | 2004-03-26 | Benzopyran compounds useful for treating inflammatory conditions. |
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| EP (1) | EP1615905A2 (sr) |
| JP (1) | JP2006522098A (sr) |
| KR (1) | KR20060015490A (sr) |
| CN (1) | CN1768050A (sr) |
| AR (1) | AR044207A1 (sr) |
| AU (1) | AU2004226164A1 (sr) |
| BR (1) | BRPI0408388A (sr) |
| CA (1) | CA2520724A1 (sr) |
| EA (1) | EA200501399A1 (sr) |
| EC (2) | ECSP056064A (sr) |
| IS (1) | IS7995A (sr) |
| MA (1) | MA27725A1 (sr) |
| MX (1) | MXPA05010630A (sr) |
| NL (9) | NL1025843C2 (sr) |
| NO (1) | NO20054121L (sr) |
| OA (1) | OA13112A (sr) |
| PA (1) | PA8599601A1 (sr) |
| PE (1) | PE20050012A1 (sr) |
| RS (1) | RS20050744A (sr) |
| TN (1) | TNSN05249A1 (sr) |
| TW (1) | TWI257927B (sr) |
| UY (1) | UY28252A1 (sr) |
| WO (1) | WO2004087686A2 (sr) |
| ZA (1) | ZA200506551B (sr) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| EP1778662A1 (en) * | 2004-07-23 | 2007-05-02 | Warner-Lambert Company LLC | Photoracemization of 2-trifluoromethyl-2h-chromene-3-carboxylic acid derivatives |
| MX2007000880A (es) * | 2004-07-23 | 2007-03-12 | Upjohn Co | Metodo enantioselectivo para separar derivados de acido 3-trifluorometil-2h-cromeno-3-carboxilico sustituido. |
| 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 |
| CA2709879A1 (en) * | 2007-12-19 | 2009-06-25 | The Scripps Research Institute | Anilides and analogs as rho kinase inhibitors |
| US20110052562A1 (en) * | 2007-12-19 | 2011-03-03 | The Scripps Research Institute | Benzimidazoles and analogs as rho kinase inhibitors |
| CA2709918A1 (en) * | 2007-12-21 | 2009-06-25 | The Scripps Research Institute | Benzopyrans 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 |
| US9573921B2 (en) * | 2013-09-30 | 2017-02-21 | Polfarmex S.A. | Substituted N, N-dimethylaminoalkyl ethers of isoflavanone oximes as H1-receptor antagonists |
| US9630896B2 (en) | 2013-11-22 | 2017-04-25 | Tansna Therapeutics, Inc. | 2,5-dialkyl-4-H/halo/ether-phenol compounds |
| AU2015206528B2 (en) | 2014-01-14 | 2019-04-18 | Euclises Pharmaceuticals, Inc. | NO-releasing nitrooxy-chromene conjugates |
| 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 |
| US12458411B2 (en) | 2017-12-07 | 2025-11-04 | Augmedics Ltd. | Spinous process clamp |
| WO2019211741A1 (en) | 2018-05-02 | 2019-11-07 | Augmedics Ltd. | Registration of a fiducial marker 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 |
| US12178666B2 (en) | 2019-07-29 | 2024-12-31 | Augmedics Ltd. | Fiducial marker |
| 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 |
| US11389252B2 (en) | 2020-06-15 | 2022-07-19 | Augmedics Ltd. | Rotating marker for image guided surgery |
| US12239385B2 (en) | 2020-09-09 | 2025-03-04 | Augmedics Ltd. | Universal tool adapter |
| US11896445B2 (en) | 2021-07-07 | 2024-02-13 | Augmedics Ltd. | Iliac pin and adapter |
| US12150821B2 (en) | 2021-07-29 | 2024-11-26 | Augmedics Ltd. | Rotating marker and adapter for image-guided surgery |
| JP2024528271A (ja) | 2021-08-05 | 2024-07-26 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | ジアミド耐性有害生物の防除方法及びそのための化合物 |
| US12475662B2 (en) | 2021-08-18 | 2025-11-18 | Augmedics Ltd. | Stereoscopic display and digital loupe for augmented-reality near-eye display |
| EP4511809A1 (en) | 2022-04-21 | 2025-02-26 | Augmedics Ltd. | Systems and methods for medical image visualization |
| IL319523A (en) | 2022-09-13 | 2025-05-01 | Augmedics Ltd | Augmented reality glasses for image-guided medical intervention |
| CN116903457A (zh) * | 2023-07-18 | 2023-10-20 | 上海添泽生物医药有限公司 | 一种2-羟基-5-异丙基苯甲酸的合成方法 |
| CN119285593B (zh) * | 2024-10-08 | 2025-09-23 | 河南农业大学 | 苯并吡喃类衍生物、合成方法及应用 |
| CN119954759B (zh) * | 2025-01-03 | 2025-10-21 | 安炎达医药技术(广州)有限公司 | 一种苯并吡喃类cox-2抑制剂及其应用 |
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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
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- 2004-03-26 CN CNA2004800089397A patent/CN1768050A/zh active Pending
- 2004-03-26 EP EP04723677A patent/EP1615905A2/en not_active Ceased
- 2004-03-26 JP JP2006506460A patent/JP2006522098A/ja not_active Abandoned
- 2004-03-26 RS YUP-2005/0744A patent/RS20050744A/sr unknown
- 2004-03-26 BR BRPI0408388-1A patent/BRPI0408388A/pt not_active IP Right Cessation
- 2004-03-26 MX MXPA05010630A patent/MXPA05010630A/es unknown
- 2004-03-26 EA EA200501399A patent/EA200501399A1/ru unknown
- 2004-03-26 AU AU2004226164A patent/AU2004226164A1/en not_active Abandoned
- 2004-03-26 OA OA1200500270A patent/OA13112A/en unknown
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- 2004-03-26 WO PCT/IB2004/001113 patent/WO2004087686A2/en not_active Ceased
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2005
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- 2005-08-16 ZA ZA200506551A patent/ZA200506551B/en unknown
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- 2005-09-05 NO NO20054121A patent/NO20054121L/no not_active Application Discontinuation
- 2005-09-29 EC EC2005006064A patent/ECSP056064A/es unknown
- 2005-09-29 EC EC2005006063A patent/ECSP056063A/es unknown
- 2005-09-30 MA MA28528A patent/MA27725A1/fr unknown
- 2005-09-30 TN TNP2005000249A patent/TNSN05249A1/fr unknown
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