AU2004236173B2 - Substituted carboxylic acids - Google Patents
Substituted carboxylic acids Download PDFInfo
- Publication number
- AU2004236173B2 AU2004236173B2 AU2004236173A AU2004236173A AU2004236173B2 AU 2004236173 B2 AU2004236173 B2 AU 2004236173B2 AU 2004236173 A AU2004236173 A AU 2004236173A AU 2004236173 A AU2004236173 A AU 2004236173A AU 2004236173 B2 AU2004236173 B2 AU 2004236173B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- phenyl
- biphenyl
- benzyl
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 150000001735 carboxylic acids Chemical class 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 526
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 400
- 150000001875 compounds Chemical class 0.000 claims description 397
- 229910052736 halogen Inorganic materials 0.000 claims description 261
- 150000002367 halogens Chemical class 0.000 claims description 261
- -1 pyrido [1 ,2-a]indolyl Chemical group 0.000 claims description 151
- 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 110
- 125000003545 alkoxy group Chemical group 0.000 claims description 98
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 96
- 125000001188 haloalkyl group Chemical group 0.000 claims description 92
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 55
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 55
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 53
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 48
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 46
- 125000001041 indolyl group Chemical group 0.000 claims description 46
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000004122 cyclic group Chemical group 0.000 claims description 34
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 32
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 31
- 229960005190 phenylalanine Drugs 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000003386 piperidinyl group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 25
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 24
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000005545 phthalimidyl group Chemical group 0.000 claims description 23
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 23
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 22
- 125000002757 morpholinyl group Chemical group 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 19
- 206010012601 diabetes mellitus Diseases 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 15
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229960003424 phenylacetic acid Drugs 0.000 claims description 10
- 239000003279 phenylacetic acid Substances 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 239000002671 adjuvant Substances 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 6
- 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 5
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 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 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- WAKZELVPMHJKIX-UHFFFAOYSA-N 2-benzyl-4-[2-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C1=CC=CC=C1C(C=C1)=CC=C1C(C1=CC=CC=C1O1)=C1CC1=CC=CC=C1 WAKZELVPMHJKIX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 3
- LSKFWNSFOPZXKV-UHFFFAOYSA-N methyl 4-[4-(4-dibenzofuran-4-ylphenyl)phenyl]-4-oxo-2-[[3-(trifluoromethyl)phenyl]methyl]butanoate Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1C(=O)CC(C(=O)OC)CC1=CC=CC(C(F)(F)F)=C1 LSKFWNSFOPZXKV-UHFFFAOYSA-N 0.000 claims description 3
- 229950009215 phenylbutanoic acid Drugs 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- CTHQHLFBRGKYCW-PMERELPUSA-N (2s)-2-[4-[4-(2-benzyl-4-fluoro-1-benzofuran-3-yl)phenyl]-2-nitroanilino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1C(=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=C(F)C=CC=C2OC=1CC=1C=CC=CC=1)[N+]([O-])=O)C1=CC=CC=C1 CTHQHLFBRGKYCW-PMERELPUSA-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
- 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
- FYGNDRLHDRXPDZ-UHFFFAOYSA-N 2-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methoxyimino]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1CON=C(C(=O)O)C1=CC=CC=C1 FYGNDRLHDRXPDZ-UHFFFAOYSA-N 0.000 claims description 2
- IPAXGSIXWVRGDU-UHFFFAOYSA-N 2-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CC1=CC=CC=C1 IPAXGSIXWVRGDU-UHFFFAOYSA-N 0.000 claims description 2
- MXGLLBXKUZEPRM-UHFFFAOYSA-N 2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]-3-(4-fluorophenyl)propanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CC1=CC=C(F)C=C1 MXGLLBXKUZEPRM-UHFFFAOYSA-N 0.000 claims description 2
- RSVSZFODKAFGLI-UHFFFAOYSA-N 2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]-4-methylpentanoic acid Chemical compound C1=CC(S(=O)(=O)NC(CC(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 RSVSZFODKAFGLI-UHFFFAOYSA-N 0.000 claims description 2
- BCAPAVNRPJLWBU-UHFFFAOYSA-N 2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]butanoic acid Chemical compound C1=CC(S(=O)(=O)NC(CC)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 BCAPAVNRPJLWBU-UHFFFAOYSA-N 0.000 claims description 2
- JZUWBNLKHMQGNS-UHFFFAOYSA-N 4-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]-2-[(4-methylsulfonylphenyl)methyl]-4-oxobutanoic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CC(C(O)=O)CC(=O)C1=CC=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 JZUWBNLKHMQGNS-UHFFFAOYSA-N 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 2
- FNLUJHLRDYYBQF-UHFFFAOYSA-N methyl 2-[4-[4-(9h-fluoren-2-yloxymethyl)phenyl]phenoxy]-2-phenylacetate Chemical compound C=1C=C(C=2C=CC(COC=3C=C4C(C5=CC=CC=C5C4)=CC=3)=CC=2)C=CC=1OC(C(=O)OC)C1=CC=CC=C1 FNLUJHLRDYYBQF-UHFFFAOYSA-N 0.000 claims description 2
- GPNPPRXNPRQBAM-UHFFFAOYSA-N methyl 2-[4-[4-[(2-benzylphenoxy)methyl]phenyl]phenoxy]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)OC(C=C1)=CC=C1C(C=C1)=CC=C1COC1=CC=CC=C1CC1=CC=CC=C1 GPNPPRXNPRQBAM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 15
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 3
- DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 claims 2
- GSJVCQGPHKZZTL-JGCGQSQUSA-N (2R)-2,5-diamino-2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-nitrophenyl]-5-oxopentanoic acid Chemical compound C(C1=CC=CC=C1)C=1OC2=C(C=1C1=CC=C(C=C1)C1=CC(=C(C=C1)[C@](N)(CCC(N)=O)C(=O)O)[N+](=O)[O-])C=CC=C2 GSJVCQGPHKZZTL-JGCGQSQUSA-N 0.000 claims 1
- 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
- PLDAFOFKTYIKNJ-MHZLTWQESA-N (2s)-2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-nitroanilino]-4-methylsulfanylbutanoic acid Chemical compound C1=C([N+]([O-])=O)C(N[C@@H](CCSC)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 PLDAFOFKTYIKNJ-MHZLTWQESA-N 0.000 claims 1
- LJPVNLNUYKHZES-HKBQPEDESA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-fluorophenyl]sulfonylamino]-3-phenylpropanoic 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)F)C1=CC=CC=C1 LJPVNLNUYKHZES-HKBQPEDESA-N 0.000 claims 1
- YTZDCEHZTQGKTO-YTTGMZPUSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]benzoyl]-methylamino]-3-methylbutanoic acid Chemical compound C1=CC(C(=O)N(C)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 YTZDCEHZTQGKTO-YTTGMZPUSA-N 0.000 claims 1
- 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 1
- 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 1
- RMJWFINHACYKJI-SIUGBPQLSA-N Ile-Tyr-Glu Chemical compound CC[C@H](C)[C@@H](C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N[C@@H](CCC(=O)O)C(=O)O)N RMJWFINHACYKJI-SIUGBPQLSA-N 0.000 claims 1
- GLQFKOVWXPPFTP-VEVYYDQMSA-N Thr-Arg-Asp Chemical compound [H]N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(O)=O GLQFKOVWXPPFTP-VEVYYDQMSA-N 0.000 claims 1
- DCLBXIWHLVEPMQ-JRQIVUDYSA-N Thr-Asp-Tyr Chemical compound C[C@@H](O)[C@H](N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 DCLBXIWHLVEPMQ-JRQIVUDYSA-N 0.000 claims 1
- GFZQWWDXJVGEMW-ULQDDVLXSA-N Tyr-Arg-Lys Chemical compound C1=CC(=CC=C1C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCCN)C(=O)O)N)O GFZQWWDXJVGEMW-ULQDDVLXSA-N 0.000 claims 1
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 claims 1
- SGPSKBLLMIGOLM-UHFFFAOYSA-N methyl 2-[4-[4-[(2-benzoylphenoxy)methyl]phenyl]phenoxy]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)OC(C=C1)=CC=C1C(C=C1)=CC=C1COC1=CC=CC=C1C(=O)C1=CC=CC=C1 SGPSKBLLMIGOLM-UHFFFAOYSA-N 0.000 claims 1
- LCMFHDKTJHAUGQ-UHFFFAOYSA-N methyl 2-[4-[4-[(3-benzoylphenoxy)methyl]phenyl]phenoxy]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)OC(C=C1)=CC=C1C(C=C1)=CC=C1COC(C=1)=CC=CC=1C(=O)C1=CC=CC=C1 LCMFHDKTJHAUGQ-UHFFFAOYSA-N 0.000 claims 1
- 108010033670 threonyl-aspartyl-tyrosine Proteins 0.000 claims 1
- 238000000034 method Methods 0.000 description 84
- 229920000728 polyester Polymers 0.000 description 80
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 125000001589 carboacyl group Chemical group 0.000 description 48
- 239000000203 mixture Substances 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
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- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
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- 150000003462 sulfoxides Chemical class 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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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- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46705703P | 2003-04-30 | 2003-04-30 | |
| US60/467,057 | 2003-04-30 | ||
| PCT/US2004/011371 WO2004099168A2 (en) | 2003-04-30 | 2004-04-14 | Substituted carboxylic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2004236173A1 AU2004236173A1 (en) | 2004-11-18 |
| AU2004236173B2 true AU2004236173B2 (en) | 2008-07-03 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004236173A Ceased AU2004236173B2 (en) | 2003-04-30 | 2004-04-14 | Substituted carboxylic acids |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7358364B2 (enExample) |
| EP (1) | EP1620420A2 (enExample) |
| JP (1) | JP2006525329A (enExample) |
| KR (1) | KR20060006953A (enExample) |
| CN (1) | CN1812977A (enExample) |
| AU (1) | AU2004236173B2 (enExample) |
| BR (1) | BRPI0409914A (enExample) |
| CA (1) | CA2523714A1 (enExample) |
| EA (1) | EA200501710A1 (enExample) |
| MX (1) | MXPA05011524A (enExample) |
| NO (1) | NO20054957L (enExample) |
| WO (1) | WO2004099168A2 (enExample) |
| ZA (1) | ZA200509631B (enExample) |
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| JP2006525329A (ja) | 2003-04-30 | 2006-11-09 | 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 | 置換カルボン酸類 |
| 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 |
| JP2008506702A (ja) | 2004-07-14 | 2008-03-06 | ピーティーシー セラピューティクス，インコーポレーテッド | Ｃ型肝炎を治療するための方法 |
| US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| NZ553329A (en) | 2004-07-22 | 2010-09-30 | Ptc Therapeutics Inc | Thienopyridines for treating hepatitis C |
| JP2008518937A (ja) * | 2004-10-28 | 2008-06-05 | ジ インスティチューツ 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 | 置換カルボン酸 |
| 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 |
| CN102775396B (zh) | 2005-11-08 | 2014-10-08 | 沃泰克斯药物股份有限公司 | Atp-结合弹夹转运蛋白的杂环调控剂 |
| US7671221B2 (en) | 2005-12-28 | 2010-03-02 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| WO2007109851A1 (en) | 2006-03-29 | 2007-10-04 | Velacor Therapeutics Pty Ltd | Treatment of neurodegenerative diseases |
| US7754739B2 (en) | 2007-05-09 | 2010-07-13 | Vertex Pharmaceuticals Incorporated | Modulators of CFTR |
| WO2008119109A1 (en) | 2007-03-29 | 2008-10-09 | Velacor Therapeutics Pty Ltd | Treatment of neurological disorders |
| JP5497633B2 (ja) | 2007-05-09 | 2014-05-21 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｃｆｔｒのモジュレーター |
| EP2231606B1 (en) | 2007-12-07 | 2013-02-13 | Vertex Pharmaceuticals Incorporated | Processes for producing cycloalkylcarboxiamido-pyridine benzoic acids |
| NZ614151A (en) | 2007-12-07 | 2015-04-24 | Vertex Pharma | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| ES2647531T3 (es) | 2008-02-28 | 2017-12-22 | Vertex Pharmaceuticals Incorporated | Derivados de heteroarilo como moduladores de CFTR |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| ES3017582T3 (en) | 2010-04-07 | 2025-05-13 | Vertex Pharma | Pharmaceutical compositions of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyriodin-2-yl)benzoic acid and administration thereof |
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- 2004-04-14 MX MXPA05011524A patent/MXPA05011524A/es not_active Application Discontinuation
- 2004-04-14 EA EA200501710A patent/EA200501710A1/ru unknown
- 2004-04-14 EP EP04760538A patent/EP1620420A2/en not_active Withdrawn
- 2004-04-14 CN CNA2004800184160A patent/CN1812977A/zh active Pending
- 2004-04-14 WO PCT/US2004/011371 patent/WO2004099168A2/en not_active Ceased
- 2004-04-14 AU AU2004236173A patent/AU2004236173B2/en not_active Ceased
- 2004-04-14 KR KR1020057020613A patent/KR20060006953A/ko not_active Withdrawn
- 2004-04-14 CA CA002523714A patent/CA2523714A1/en not_active Abandoned
- 2004-04-14 US US10/823,842 patent/US7358364B2/en not_active Expired - Fee Related
- 2004-04-14 BR BRPI0409914-1A patent/BRPI0409914A/pt not_active IP Right Cessation
-
2005
- 2005-10-25 NO NO20054957A patent/NO20054957L/no not_active Application Discontinuation
- 2005-11-29 ZA ZA200509631A patent/ZA200509631B/en unknown
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2008
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Also Published As
| Publication number | Publication date |
|---|---|
| NO20054957L (no) | 2006-01-23 |
| MXPA05011524A (es) | 2006-03-21 |
| EA200501710A1 (ru) | 2006-06-30 |
| US20090082392A1 (en) | 2009-03-26 |
| WO2004099168A3 (en) | 2005-02-24 |
| BRPI0409914A (pt) | 2006-04-25 |
| WO2004099168A2 (en) | 2004-11-18 |
| NO20054957D0 (no) | 2005-10-25 |
| US20040266788A1 (en) | 2004-12-30 |
| CN1812977A (zh) | 2006-08-02 |
| EP1620420A2 (en) | 2006-02-01 |
| AU2004236173A1 (en) | 2004-11-18 |
| KR20060006953A (ko) | 2006-01-20 |
| ZA200509631B (en) | 2007-02-28 |
| CA2523714A1 (en) | 2004-11-18 |
| US7358364B2 (en) | 2008-04-15 |
| JP2006525329A (ja) | 2006-11-09 |
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