ZA200509631B - Subsituted carboxylic acids - Google Patents
Subsituted carboxylic acids Download PDFInfo
- Publication number
- ZA200509631B ZA200509631B ZA200509631A ZA200509631A ZA200509631B ZA 200509631 B ZA200509631 B ZA 200509631B ZA 200509631 A ZA200509631 A ZA 200509631A ZA 200509631 A ZA200509631 A ZA 200509631A ZA 200509631 B ZA200509631 B ZA 200509631B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- phenyl
- biphenyl
- benzyl
- benzofuran
- Prior art date
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- 150000001735 carboxylic acids Chemical class 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 493
- 150000001875 compounds Chemical class 0.000 claims description 347
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 225
- 229910052736 halogen Inorganic materials 0.000 claims description 158
- 150000002367 halogens Chemical class 0.000 claims description 158
- 125000003545 alkoxy group Chemical group 0.000 claims description 128
- -1 -S80 Chemical group 0.000 claims description 105
- 238000000034 method Methods 0.000 claims description 85
- 125000001188 haloalkyl group Chemical group 0.000 claims description 69
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 68
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 59
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 52
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 44
- 229910052799 carbon Inorganic materials 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 37
- 125000001589 carboacyl group Chemical group 0.000 claims description 37
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 35
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 229920000728 polyester Polymers 0.000 claims description 31
- 125000001041 indolyl group Chemical group 0.000 claims description 29
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 125000004122 cyclic group Chemical group 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 18
- 229960005190 phenylalanine Drugs 0.000 claims description 18
- 125000003386 piperidinyl group Chemical group 0.000 claims description 18
- 206010012601 diabetes mellitus Diseases 0.000 claims description 17
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 17
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000005545 phthalimidyl group Chemical group 0.000 claims description 15
- 125000002757 morpholinyl group Chemical group 0.000 claims description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- 239000002671 adjuvant Substances 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical compound CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- QEYCNFONUGAJSK-XIFFEERXSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]benzoyl]-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)C(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 QEYCNFONUGAJSK-XIFFEERXSA-N 0.000 claims description 2
- ZVKRFSNAJWLMPK-YTTGMZPUSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]-3-(3-fluorophenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C1=CC=CC(F)=C1 ZVKRFSNAJWLMPK-YTTGMZPUSA-N 0.000 claims description 2
- LHKBJCSEDWDFQU-UHFFFAOYSA-N 2-[3-chloro-4-(4-dibenzofuran-4-ylphenyl)phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C(Cl)=CC=1OC(C(=O)O)C1=CC=CC=C1 LHKBJCSEDWDFQU-UHFFFAOYSA-N 0.000 claims description 2
- XNIYTDCYFRYSBN-UHFFFAOYSA-N 2-[4-(4-dibenzofuran-4-ylphenyl)-2-fluorophenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=C(F)C=1OC(C(=O)O)C1=CC=CC=C1 XNIYTDCYFRYSBN-UHFFFAOYSA-N 0.000 claims description 2
- QQYFRIAAVHUCJW-UHFFFAOYSA-N 2-[4-(4-dibenzofuran-4-ylphenyl)-3-(trifluoromethyl)phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C(C(F)(F)F)=CC=1OC(C(=O)O)C1=CC=CC=C1 QQYFRIAAVHUCJW-UHFFFAOYSA-N 0.000 claims description 2
- GSUCSJIGNHMJKC-UHFFFAOYSA-N 2-[4-(4-dibenzofuran-4-ylphenyl)-3-methylphenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C(C)=CC=1OC(C(O)=O)C1=CC=CC=C1 GSUCSJIGNHMJKC-UHFFFAOYSA-N 0.000 claims description 2
- OZTCLTRYZGGMDA-UHFFFAOYSA-N 2-[4-(4-dibenzofuran-4-ylphenyl)phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 OZTCLTRYZGGMDA-UHFFFAOYSA-N 0.000 claims description 2
- PVFRKJHMBYMZRC-UHFFFAOYSA-N 2-[4-(4-indol-1-ylphenyl)phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C=C2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 PVFRKJHMBYMZRC-UHFFFAOYSA-N 0.000 claims description 2
- PUBMZUOBSIJWOM-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 PUBMZUOBSIJWOM-UHFFFAOYSA-N 0.000 claims description 2
- CPNWIHWVKIGEIY-UHFFFAOYSA-N 2-[4-[4-(5-chloroindol-1-yl)phenyl]phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)N2C3=CC=C(Cl)C=C3C=C2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 CPNWIHWVKIGEIY-UHFFFAOYSA-N 0.000 claims description 2
- MPXRREHOMCUVNZ-UHFFFAOYSA-N 2-benzyl-4-[4-(4-indol-1-ylphenyl)phenyl]-4-oxobutanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C=C2)C=CC=1C(=O)CC(C(=O)O)CC1=CC=CC=C1 MPXRREHOMCUVNZ-UHFFFAOYSA-N 0.000 claims description 2
- WLXCNKISKIXXST-UHFFFAOYSA-N 2-benzyl-4-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2,6-dimethylphenyl]-4-oxobutanoic acid Chemical compound CC1=CC(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)=CC(C)=C1C(=O)CC(C(O)=O)CC1=CC=CC=C1 WLXCNKISKIXXST-UHFFFAOYSA-N 0.000 claims description 2
- XWPMVHQMDVXBDB-UHFFFAOYSA-N 4-(4-dibenzofuran-4-ylphenyl)-4-oxo-2-[[3-(trifluoromethyl)phenyl]methyl]butanoic acid Chemical compound C=1C=C(C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1C(=O)CC(C(=O)O)CC1=CC=CC(C(F)(F)F)=C1 XWPMVHQMDVXBDB-UHFFFAOYSA-N 0.000 claims description 2
- FOUKSPNWVQXNSE-UHFFFAOYSA-N 4-[4-(4-dibenzofuran-4-ylphenyl)phenyl]-4-oxo-2-[[3-(trifluoromethyl)phenyl]methyl]butanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1C(=O)CC(C(=O)O)CC1=CC=CC(C(F)(F)F)=C1 FOUKSPNWVQXNSE-UHFFFAOYSA-N 0.000 claims description 2
- BVVWCVAFOUVSLH-UHFFFAOYSA-N C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1CON=C(CC(=O)O)C1=CC=CC=C1 Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1CON=C(CC(=O)O)C1=CC=CC=C1 BVVWCVAFOUVSLH-UHFFFAOYSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006309 butyl amino group Chemical group 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 229960003424 phenylacetic acid Drugs 0.000 claims description 2
- 239000003279 phenylacetic acid Substances 0.000 claims description 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- TVGXOXUAFKXOQE-VWLOTQADSA-N (2s)-2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-nitroanilino]-3-hydroxypropanoic acid Chemical compound C1=C([N+]([O-])=O)C(N[C@@H](CO)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 TVGXOXUAFKXOQE-VWLOTQADSA-N 0.000 claims 1
- SKVKSLAIKOIQDV-HKBQPEDESA-N (2s)-2-[[4-[4-(1-butylindolizin-2-yl)phenyl]benzoyl]amino]-3-phenylpropanoic acid Chemical compound C([C@H](NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C=1C(=C2C=CC=CN2C=1)CCCC)C(O)=O)C1=CC=CC=C1 SKVKSLAIKOIQDV-HKBQPEDESA-N 0.000 claims 1
- NHIMACVYYZIWJC-UMSFTDKQSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonyl-ethylamino]-3-(4-fluorophenyl)propanoic acid Chemical compound C([C@H](N(CC)S(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C(O)=O)C1=CC=C(F)C=C1 NHIMACVYYZIWJC-UMSFTDKQSA-N 0.000 claims 1
- NNFVGFXSJCCBRK-XIFFEERXSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonyl-methylamino]-3-(3-fluorophenyl)propanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C(O)=O)C1=CC=CC(F)=C1 NNFVGFXSJCCBRK-XIFFEERXSA-N 0.000 claims 1
- ZRECXQDSNGZOPR-XIFFEERXSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonyl-methylamino]-3-(4-fluorophenyl)propanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C(O)=O)C1=CC=C(F)C=C1 ZRECXQDSNGZOPR-XIFFEERXSA-N 0.000 claims 1
- DUJKEHAVYGLFTH-XIFFEERXSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 DUJKEHAVYGLFTH-XIFFEERXSA-N 0.000 claims 1
- NOCKIGVUZLZBOZ-NDEPHWFRSA-N (2s)-2-[[4-[4-(5-methylindol-1-yl)phenyl]benzoyl]amino]-3-phenylpropanoic acid Chemical compound C([C@H](NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)N1C2=CC=C(C=C2C=C1)C)C(O)=O)C1=CC=CC=C1 NOCKIGVUZLZBOZ-NDEPHWFRSA-N 0.000 claims 1
- QVQXHODTLOOOCB-YTTGMZPUSA-N (2s)-2-[[4-[4-[(2-butyl-1-benzofuran-3-yl)methyl]phenyl]benzoyl]-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CC=1C2=CC=CC=C2OC=1CCCC)C(O)=O)C1=CC=CC=C1 QVQXHODTLOOOCB-YTTGMZPUSA-N 0.000 claims 1
- JYDNEWUUQHTPMP-YTTGMZPUSA-N (2s)-2-[[4-[4-[(2-butyl-1-benzofuran-3-yl)methyl]phenyl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CC=1C2=CC=CC=C2OC=1CCCC)C(O)=O)C1=CC=CC=C1 JYDNEWUUQHTPMP-YTTGMZPUSA-N 0.000 claims 1
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- OQDDQVVATCIZAD-UHFFFAOYSA-N 2-[4-[4-(1-benzylindol-6-yl)phenyl]phenoxy]-2-phenylacetic acid 4-[4-(4-dibenzofuran-4-ylphenyl)phenyl]-4-oxo-2-[[3-(trifluoromethyl)phenyl]methyl]butanoic acid Chemical compound C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC=C(C=C1)C1=CC=C(C=C1)OC(C(=O)O)C1=CC=CC=C1.C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)C3=CC=C(C=C3)C(CC(C(=O)O)CC3=CC(=CC=C3)C(F)(F)F)=O OQDDQVVATCIZAD-UHFFFAOYSA-N 0.000 claims 1
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- JBPANPVYVLBQAD-UHFFFAOYSA-N 2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-fluorophenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C(F)C=1S(=O)(=O)N(C)C(C(O)=O)CC1=CC=CC=C1 JBPANPVYVLBQAD-UHFFFAOYSA-N 0.000 claims 1
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- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
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- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
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- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
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- 230000001225 therapeutic effect Effects 0.000 description 1
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
- C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46705703P | 2003-04-30 | 2003-04-30 |
Publications (1)
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|---|---|
| ZA200509631B true ZA200509631B (en) | 2007-02-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200509631A ZA200509631B (en) | 2003-04-30 | 2005-11-29 | Subsituted carboxylic acids |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7358364B2 (fr) |
| EP (1) | EP1620420A2 (fr) |
| JP (1) | JP2006525329A (fr) |
| KR (1) | KR20060006953A (fr) |
| CN (1) | CN1812977A (fr) |
| AU (1) | AU2004236173B2 (fr) |
| BR (1) | BRPI0409914A (fr) |
| CA (1) | CA2523714A1 (fr) |
| EA (1) | EA200501710A1 (fr) |
| MX (1) | MXPA05011524A (fr) |
| NO (1) | NO20054957L (fr) |
| WO (1) | WO2004099168A2 (fr) |
| ZA (1) | ZA200509631B (fr) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7358364B2 (en) | 2003-04-30 | 2008-04-15 | The Institute For Pharmaceutical Discovery Llc | Substituted carboxylic acids |
| US7582773B2 (en) * | 2003-09-25 | 2009-09-01 | Wyeth | Substituted phenyl indoles |
| FR2869615B1 (fr) * | 2004-05-03 | 2007-11-16 | Merck Sante Soc Par Actions Si | Derives de l'acide butanoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et leurs applications therapeutiques |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| WO2006019831A1 (fr) | 2004-07-14 | 2006-02-23 | Ptc Therapeutics, Inc. | Procedes pour le traitement de l'hepatite c |
| US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| WO2006019832A1 (fr) | 2004-07-22 | 2006-02-23 | Ptc Therapeutics, Inc. | Thienopyridines utilisees pour traiter l'hepatite c |
| US20060094747A1 (en) * | 2004-10-28 | 2006-05-04 | The Institute For Pharmaceutical Discovery, L.L.C. | Substituted carboxylic acids |
| JP2008520692A (ja) * | 2004-11-18 | 2008-06-19 | ジ インスチチュート フォー ファーマシューティカル ディスカバリー、エルエルシー | 複素環置換カルボン酸 |
| KR101331768B1 (ko) | 2005-11-08 | 2013-11-22 | 버텍스 파마슈티칼스 인코포레이티드 | Ａｔｐ 결합 카세트 수송체의 헤테로사이클릭 조정제 |
| US7671221B2 (en) | 2005-12-28 | 2010-03-02 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| NZ596244A (en) | 2006-03-29 | 2013-05-31 | Velacor Therapeutics Pty Ltd | Treatment of neurodegenerative diseases |
| US7754739B2 (en) | 2007-05-09 | 2010-07-13 | Vertex Pharmaceuticals Incorporated | Modulators of CFTR |
| WO2008119109A1 (fr) | 2007-03-29 | 2008-10-09 | Velacor Therapeutics Pty Ltd | Traitement de troubles neurologiques |
| WO2008141119A2 (fr) | 2007-05-09 | 2008-11-20 | Vertex Pharmaceuticals Incorporated | Modulateurs de cftr |
| UA102534C2 (en) | 2007-12-07 | 2013-07-25 | Вертекс Фармасьютикалз Инкорпорейтед | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]-dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid |
| SI2639224T1 (sl) | 2007-12-07 | 2016-12-30 | Vertex Pharmaceuticals Incorporated | Postopek za pripravo cikloalkilkarboksiamido-piridinskih benzojskih kislin |
| EP2271622B1 (fr) | 2008-02-28 | 2017-10-04 | Vertex Pharmaceuticals Incorporated | Dérivés d'hétéroarènes en tant que modulateurs de CFTR |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| CN102917692A (zh) | 2010-04-07 | 2013-02-06 | 弗特克斯药品有限公司 | 3-(6-(1-(2,2-二氟苯并[d][1,3]二氧杂环戊烯-5-基)环丙甲酰胺基)-3-甲基吡啶-2-基)苯甲酸的药物组合物和其给药方法 |
| WO2012081736A1 (fr) | 2010-12-17 | 2012-06-21 | Mitsubishi Tanabe Pharma Corporation | Composé arycyclique continu |
| JP5977349B2 (ja) | 2012-06-15 | 2016-08-24 | 田辺三菱製薬株式会社 | 芳香族複素環化合物 |
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-
2004
- 2004-04-14 US US10/823,842 patent/US7358364B2/en not_active Expired - Fee Related
- 2004-04-14 CA CA002523714A patent/CA2523714A1/fr not_active Abandoned
- 2004-04-14 WO PCT/US2004/011371 patent/WO2004099168A2/fr active Application Filing
- 2004-04-14 EP EP04760538A patent/EP1620420A2/fr not_active Withdrawn
- 2004-04-14 EA EA200501710A patent/EA200501710A1/ru unknown
- 2004-04-14 MX MXPA05011524A patent/MXPA05011524A/es not_active Application Discontinuation
- 2004-04-14 KR KR1020057020613A patent/KR20060006953A/ko not_active Application Discontinuation
- 2004-04-14 JP JP2006509981A patent/JP2006525329A/ja active Pending
- 2004-04-14 BR BRPI0409914-1A patent/BRPI0409914A/pt not_active IP Right Cessation
- 2004-04-14 CN CNA2004800184160A patent/CN1812977A/zh active Pending
- 2004-04-14 AU AU2004236173A patent/AU2004236173B2/en not_active Ceased
-
2005
- 2005-10-25 NO NO20054957A patent/NO20054957L/no not_active Application Discontinuation
- 2005-11-29 ZA ZA200509631A patent/ZA200509631B/en unknown
-
2008
- 2008-04-15 US US12/103,082 patent/US20090082392A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20090082392A1 (en) | 2009-03-26 |
| WO2004099168A3 (fr) | 2005-02-24 |
| US7358364B2 (en) | 2008-04-15 |
| NO20054957L (no) | 2006-01-23 |
| JP2006525329A (ja) | 2006-11-09 |
| WO2004099168A2 (fr) | 2004-11-18 |
| AU2004236173A1 (en) | 2004-11-18 |
| CN1812977A (zh) | 2006-08-02 |
| US20040266788A1 (en) | 2004-12-30 |
| EA200501710A1 (ru) | 2006-06-30 |
| NO20054957D0 (no) | 2005-10-25 |
| MXPA05011524A (es) | 2006-03-21 |
| KR20060006953A (ko) | 2006-01-20 |
| EP1620420A2 (fr) | 2006-02-01 |
| AU2004236173B2 (en) | 2008-07-03 |
| BRPI0409914A (pt) | 2006-04-25 |
| CA2523714A1 (fr) | 2004-11-18 |
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