JP2006525364A5 - - Google Patents
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- JP2006525364A5 JP2006525364A5 JP2006514243A JP2006514243A JP2006525364A5 JP 2006525364 A5 JP2006525364 A5 JP 2006525364A5 JP 2006514243 A JP2006514243 A JP 2006514243A JP 2006514243 A JP2006514243 A JP 2006514243A JP 2006525364 A5 JP2006525364 A5 JP 2006525364A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- phenyl
- cysteine
- tert
- 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.)
- Abandoned
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- -1 imidazolylmethyl Chemical group 0.000 claims description 127
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 33
- 241000257303 Hymenoptera Species 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000001041 indolyl group Chemical group 0.000 claims description 10
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 6
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 63
- 239000004201 L-cysteine Substances 0.000 claims 32
- 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 31
- 235000018417 cysteine Nutrition 0.000 claims 24
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 24
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 23
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 229960003767 alanine Drugs 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- KEYCHRBBPDCUSJ-UHFFFAOYSA-N 4-[4-(4-dibenzofuran-4-ylphenyl)phenyl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound C1=CC(SCCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 KEYCHRBBPDCUSJ-UHFFFAOYSA-N 0.000 claims 3
- 229910019142 PO4 Inorganic materials 0.000 claims 3
- 239000010452 phosphate Substances 0.000 claims 3
- BGTZUSLLUBAURE-UHFFFAOYSA-N 3-[4-(4-dibenzofuran-4-ylphenyl)phenyl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC(SCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 BGTZUSLLUBAURE-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- IVHUQFXPVPXAES-UHFFFAOYSA-N 5-[4-(4-dibenzofuran-4-ylphenyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid Chemical compound C1=CC(CCCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 IVHUQFXPVPXAES-UHFFFAOYSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 239000004474 valine Substances 0.000 claims 2
- UNEQQPJDUOEGTH-NDEPHWFRSA-N (2S)-2-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methyl-[(2-methylpropan-2-yl)oxycarbonyloxy]amino]-3-hydroxypropanoic acid Chemical compound C(C)(C)(C)OC(=O)ON([C@@H](CO)C(=O)O)CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 UNEQQPJDUOEGTH-NDEPHWFRSA-N 0.000 claims 1
- YALODQGHUHJVPN-HXUWFJFHSA-N (2s)-3-[[4-[(2-indol-1-ylacetyl)amino]phenyl]methylsulfonyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC(CS(=O)(=O)C[C@@H](NC(=O)OC(C)(C)C)C(O)=O)=CC=C1NC(=O)CN1C2=CC=CC=C2C=C1 YALODQGHUHJVPN-HXUWFJFHSA-N 0.000 claims 1
- KTYYHUIVNWBFFI-SOFGYWHQSA-N (e)-5-[4-(4-dibenzofuran-4-ylphenyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoic acid Chemical compound C1=CC(/C=C/CC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 KTYYHUIVNWBFFI-SOFGYWHQSA-N 0.000 claims 1
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 claims 1
- 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 claims 1
- HCFMAHUGFXFZPX-UHFFFAOYSA-N 2-(butoxycarbonylamino)-3-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methoxy]propanoic acid Chemical compound C1=CC(COCC(NC(=O)OCCCC)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 HCFMAHUGFXFZPX-UHFFFAOYSA-N 0.000 claims 1
- YBDUNKAEHQMJAV-UHFFFAOYSA-N 2-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 YBDUNKAEHQMJAV-UHFFFAOYSA-N 0.000 claims 1
- IFHOIJQLBOWQIF-UHFFFAOYSA-N 2-[[1-carboxy-2-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methylsulfanyl]ethyl]carbamoyl]benzoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1CSCC(C(=O)O)NC(=O)C1=CC=CC=C1C(O)=O IFHOIJQLBOWQIF-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 claims 1
- BERGPZSEQWYHFX-UHFFFAOYSA-N 3-[3-(4-dibenzofuran-4-ylphenyl)phenyl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CSC1=CC=CC(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)=C1 BERGPZSEQWYHFX-UHFFFAOYSA-N 0.000 claims 1
- VULULKHGPOTUHE-UHFFFAOYSA-N 3-[4-(4-dibenzofuran-4-ylphenyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C(C)(C)(C)OC(=O)NC(C(=O)O)CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 VULULKHGPOTUHE-UHFFFAOYSA-N 0.000 claims 1
- YPEOYXJDBWRCMF-UHFFFAOYSA-N 3-[[4-(2-dibenzofuran-4-yl-1,3-thiazol-5-yl)phenyl]methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC(CSCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CN=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)S1 YPEOYXJDBWRCMF-UHFFFAOYSA-N 0.000 claims 1
- MJFLNFXGQKBBQG-UHFFFAOYSA-N 3-[[4-(4,6-diphenylpyrimidin-2-yl)phenyl]methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC(CSCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=NC(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=N1 MJFLNFXGQKBBQG-UHFFFAOYSA-N 0.000 claims 1
- KZVMEGHJFZVDEC-UHFFFAOYSA-N 3-[[4-(4-dibenzofuran-4-ylphenyl)-2-fluorophenyl]methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=C(F)C(CSCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 KZVMEGHJFZVDEC-UHFFFAOYSA-N 0.000 claims 1
- LMVAFTBWIWTDBP-UHFFFAOYSA-N 3-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC(COCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 LMVAFTBWIWTDBP-UHFFFAOYSA-N 0.000 claims 1
- VPRDPWQVFDHBRA-UHFFFAOYSA-N 3-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methylsulfanyl]-2-(pyridine-3-carbonylamino)propanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1CSCC(C(=O)O)NC(=O)C1=CC=CN=C1 VPRDPWQVFDHBRA-UHFFFAOYSA-N 0.000 claims 1
- HCTDNQMQTYUQGK-UHFFFAOYSA-N 3-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC(CSCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 HCTDNQMQTYUQGK-UHFFFAOYSA-N 0.000 claims 1
- BUWHXQLVRKNQGH-UHFFFAOYSA-N 3-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methylsulfanyl]-2-[[4-(trifluoromethyl)phenyl]methylamino]propanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1CSCC(C(=O)O)NCC1=CC=C(C(F)(F)F)C=C1 BUWHXQLVRKNQGH-UHFFFAOYSA-N 0.000 claims 1
- KIEPMAPCXFNKGV-UHFFFAOYSA-N 3-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methylsulfanyl]-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound C1=CC(CSC(C)(C)C(C(O)=O)NC(=O)OC(C)(C)C)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 KIEPMAPCXFNKGV-UHFFFAOYSA-N 0.000 claims 1
- GAMLAGMUJVWZFN-UHFFFAOYSA-N 3-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methylsulfonyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC(CS(=O)(=O)CC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 GAMLAGMUJVWZFN-UHFFFAOYSA-N 0.000 claims 1
- IVRNIZSWELMWRE-UHFFFAOYSA-N 3-[[4-(4-dibenzothiophen-4-ylphenyl)phenyl]methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC(CSCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3SC4=CC=CC=C4C=3C=CC=2)C=C1 IVRNIZSWELMWRE-UHFFFAOYSA-N 0.000 claims 1
- PWKGEKXYPNMOIQ-UHFFFAOYSA-N 3-[[4-(5-dibenzofuran-4-yl-6-methylpyridin-2-yl)phenyl]methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C=1C=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C(C)=NC=1C1=CC=C(CSCC(NC(=O)OC(C)(C)C)C(O)=O)C=C1 PWKGEKXYPNMOIQ-UHFFFAOYSA-N 0.000 claims 1
- JLCNJNODRPDAMB-UHFFFAOYSA-N 3-[[4-(6-dibenzofuran-4-ylpyridin-3-yl)phenyl]methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC(CSCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)N=C1 JLCNJNODRPDAMB-UHFFFAOYSA-N 0.000 claims 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
- RVTLMUXWHUQHNO-UHFFFAOYSA-N 4-[4-(4-dibenzofuran-4-ylphenyl)phenoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound C1=CC(OCCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 RVTLMUXWHUQHNO-UHFFFAOYSA-N 0.000 claims 1
- WRCOYNGWCRXTKM-UHFFFAOYSA-N 4-[4-(4-dibenzofuran-4-ylphenyl)phenyl]sulfonyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound C1=CC(S(=O)(=O)CCC(NC(=O)OC(C)(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 WRCOYNGWCRXTKM-UHFFFAOYSA-N 0.000 claims 1
- GVANNXXGASAZAH-UHFFFAOYSA-N 4-[[1-carboxy-2-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methylsulfanyl]ethyl]amino]-4-oxobutanoic acid Chemical compound C1=CC(CSCC(NC(=O)CCC(=O)O)C(O)=O)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 GVANNXXGASAZAH-UHFFFAOYSA-N 0.000 claims 1
- WTZBEUGDAPCVOF-UHFFFAOYSA-N 4-[[1-carboxy-2-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methylsulfanyl]ethyl]carbamoyl]benzoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1CSCC(C(=O)O)NC(=O)C1=CC=C(C(O)=O)C=C1 WTZBEUGDAPCVOF-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims 1
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims 1
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 claims 1
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- HIYNHYCNAGFJEH-UHFFFAOYSA-N methyl 3-[4-(4-dibenzofuran-4-ylphenyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound COC(C(CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O HIYNHYCNAGFJEH-UHFFFAOYSA-N 0.000 claims 1
- JWLNHTINDFOERB-UHFFFAOYSA-N methyl 3-[4-(4-dibenzofuran-4-ylphenyl)phenyl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound COC(C(CSC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O JWLNHTINDFOERB-UHFFFAOYSA-N 0.000 claims 1
- SFWGLFNINJJFGP-UHFFFAOYSA-N methyl 3-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C1=CC(COCC(C(=O)OC)NC(=O)OC(C)(C)C)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 SFWGLFNINJJFGP-UHFFFAOYSA-N 0.000 claims 1
- OZAVYLDGYPZAGG-UHFFFAOYSA-N methyl 3-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methylsulfanyl]-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate Chemical compound C1=CC(CSC(C)(C)C(NC(=O)OC(C)(C)C)C(=O)OC)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 OZAVYLDGYPZAGG-UHFFFAOYSA-N 0.000 claims 1
- PQYBZHYXKCBJMW-UHFFFAOYSA-N methyl 4-[4-(4-dibenzofuran-4-ylphenyl)phenyl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate Chemical compound C1=CC(SCCC(C(=O)OC)NC(=O)OC(C)(C)C)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 PQYBZHYXKCBJMW-UHFFFAOYSA-N 0.000 claims 1
- XTEIFMBCCOINBY-UHFFFAOYSA-N methyl 5-[4-(4-dibenzofuran-4-ylphenyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate Chemical compound C1=CC(CCCC(C(=O)OC)NC(=O)OC(C)(C)C)=CC=C1C1=CC=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 XTEIFMBCCOINBY-UHFFFAOYSA-N 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 0 *C(*1)=C(CSCC(C(O*)=O)N*)C=CC1=C1C=C*C=C1 Chemical compound *C(*1)=C(CSCC(C(O*)=O)N*)C=CC1=C1C=C*C=C1 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46687003P | 2003-04-30 | 2003-04-30 | |
| PCT/US2004/013700 WO2004099171A2 (en) | 2003-04-30 | 2004-04-30 | Substituted amino carboxylic acids as inhibitors of protein tyrosine phosphatase-1b |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006525364A JP2006525364A (ja) | 2006-11-09 |
| JP2006525364A5 true JP2006525364A5 (https=) | 2007-05-17 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2006514243A Abandoned JP2006525364A (ja) | 2003-04-30 | 2004-04-30 | 置換アミノカルボン酸 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7358248B2 (https=) |
| EP (1) | EP1622886A2 (https=) |
| JP (1) | JP2006525364A (https=) |
| KR (1) | KR20050115337A (https=) |
| CN (1) | CN1812979A (https=) |
| AU (1) | AU2004236247B2 (https=) |
| BR (1) | BRPI0409924A (https=) |
| CA (1) | CA2523718A1 (https=) |
| CO (1) | CO5700733A2 (https=) |
| EA (1) | EA200501715A1 (https=) |
| MX (1) | MXPA05011537A (https=) |
| NO (1) | NO20054958L (https=) |
| RS (1) | RS20050814A (https=) |
| WO (1) | WO2004099171A2 (https=) |
| ZA (1) | ZA200509630B (https=) |
Families Citing this family (35)
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|---|---|---|---|---|
| EP1483283A4 (en) | 2002-03-13 | 2007-04-11 | Signum Biosciences Inc | MODULATION OF PROTEIN METHYLATION AND PHOSPHOPROTEIN PHOSPHATE |
| EP1622886A2 (en) | 2003-04-30 | 2006-02-08 | The Institutes for Pharmaceutical Discovery, LLC | Substituted amino carboxylic acids as inhibitors of protein tyrosine phosphatase-1b |
| US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| WO2006019831A1 (en) | 2004-07-14 | 2006-02-23 | Ptc Therapeutics, Inc. | Methods for treating hepatitis c |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| WO2006019832A1 (en) | 2004-07-22 | 2006-02-23 | Ptc Therapeutics, Inc. | Thienopyridines for treating hepatitis c |
| AU2005302409A1 (en) * | 2004-10-28 | 2006-05-11 | The Institutes For Pharmaceutical Discovery Llc | Substituted carboxylic acids |
| EP1836182A2 (en) * | 2004-11-18 | 2007-09-26 | The Institutes for Pharmaceutical Discovery, LLC | Heterocyclylbiphenyl derivates as protein tyrosine phosphatase inhibitors |
| JP2008520693A (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 | プロテインチロシンホスファターゼ阻害剤としての置換アミノ酸 |
| DE102004060542A1 (de) | 2004-12-16 | 2006-07-06 | Sanofi-Aventis Deutschland Gmbh | Hydroxybiphenyl-Carbonsäuren und Derivate, Verfahren zu deren Herstellung und deren Verwendung |
| US7923041B2 (en) | 2005-02-03 | 2011-04-12 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| CA2601777A1 (en) | 2005-02-03 | 2006-08-10 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| JP5315060B2 (ja) | 2006-02-03 | 2013-10-16 | バイオノミックス リミテッド | 置換ベンゾフラン、ベンゾチオフェン、ベンゾセレノフェンおよびインドールおよびそれらのチューブリン重合阻害剤としての使用 |
| WO2008033455A2 (en) * | 2006-09-13 | 2008-03-20 | The Institutes For Pharmaceutical Discovery, Llc | Biphenyl and heteroaryl phenyl derivatives as protein tyrosine phosphatases inhibitors |
| WO2008033931A1 (en) * | 2006-09-13 | 2008-03-20 | The Institutes For Pharmaceutical Discovery, Llc | Para-xylylene carboxylic acids and isothiazolones useful as protein tyrosine phosphatases (ptps) in particular ptp-ib |
| CN101910159B (zh) * | 2007-12-26 | 2013-06-19 | 卫材R&D管理有限公司 | 杂环取代吡啶衍生物的制备方法 |
| CN101945652A (zh) * | 2008-02-14 | 2011-01-12 | 西格纳姆生物科学公司 | 抑制异戊二烯基-s-半胱氨酰基甲基转移酶的乙酰基模拟化合物 |
| AU2009239430B2 (en) | 2008-04-21 | 2015-01-22 | Signum Biosciences, Inc. | Compounds, compositions and methods for making the same |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| US8765817B1 (en) | 2008-12-03 | 2014-07-01 | Arrowhead Center, Inc. | Selective inhibitors of EG5 motors and methods of use |
| US8349899B1 (en) | 2008-12-03 | 2013-01-08 | Arrowhead Center, Inc. | Selective inhibitors of EG5 motors and methods of use |
| SG176009A1 (en) | 2009-05-28 | 2011-12-29 | Novartis Ag | Substituted aminopropionic derivatives as neprilysin inhibitors |
| JP5466759B2 (ja) | 2009-05-28 | 2014-04-09 | ノバルティス アーゲー | ネプリライシン阻害剤としての置換アミノ酪酸誘導体 |
| CN102030700B (zh) * | 2009-09-30 | 2016-06-01 | 中国医学科学院药物研究所 | 苯甲酰胺基羧酸类化合物及其制法和药物用途 |
| JO2967B1 (en) | 2009-11-20 | 2016-03-15 | نوفارتس ايه جي | Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors |
| JP5814031B2 (ja) * | 2010-07-30 | 2015-11-17 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、及びジベンゾチオフェン構造又はジベンゾフラン構造を有する有機電界発光素子用材料 |
| US8673974B2 (en) | 2010-11-16 | 2014-03-18 | Novartis Ag | Substituted amino bisphenyl pentanoic acid derivatives as NEP inhibitors |
| JP6301371B2 (ja) | 2013-02-14 | 2018-04-11 | ノバルティス アーゲー | インビボ効力が改善されたｎｅｐ阻害剤としての置換ビスフェニルブタン酸誘導体 |
| TR201808541T4 (tr) | 2013-02-14 | 2018-07-23 | Novartis Ag | Nep (nötr endopeptidaz) inhibitörleri olarak ikame edilmiş bisfenil butanoik fosfonik asit türevleri. |
| US20170022171A1 (en) | 2014-04-03 | 2017-01-26 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituted cyclopentanecarboxylic acids and their use |
| CA2944614A1 (en) | 2014-04-03 | 2015-10-08 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituted cyclopentane carboxylic acids for the treatment of respiratoy tract diseases |
| US20170119776A1 (en) | 2014-04-03 | 2017-05-04 | Bayer Pharma Aktiengesellschaft | Chiral 2,5-disubstituted cyclopentanecarboxylic acid derivatives and use thereof |
| US11655468B2 (en) | 2018-07-25 | 2023-05-23 | The Trustees Of Boston College | Methods and compositions of chemically modified phage libraries |
| WO2020023620A1 (en) * | 2018-07-25 | 2020-01-30 | Trustees Of Boston College | Methods and compositions of chemically modified phage libraries |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950542A (en) * | 1967-02-21 | 1976-04-13 | L'oreal | Cysteamine derivatives for oral treatment of seborrhea |
| FR2531083B1 (fr) | 1982-06-29 | 1986-11-28 | Sandoz Sa | Nouveaux derives de la piperidine, leur preparation et leur utilisation comme medicaments |
| EP0254032A3 (en) * | 1986-06-20 | 1990-09-05 | Schering Corporation | Neutral metalloendopeptidase inhibitors in the treatment of hypertension |
| US4863919A (en) | 1988-02-01 | 1989-09-05 | A. H. Robins Company, Incorporated | Method of enhancing memory or correcting memory deficiency with arylamido(and arylthiomido)-azabicycloalkanes |
| DE69528197T2 (de) * | 1994-12-14 | 2003-06-05 | Santen Pharmaceutical Co., Ltd | Neue 1,3-dialkylharnstoff-derivate |
| GB9518553D0 (en) | 1995-09-11 | 1995-11-08 | Fujisawa Pharmaceutical Co | New urea derivatives processes for the preparation thereof and pharmaceutical composition comprising the same |
| MY153569A (en) | 1998-01-20 | 2015-02-27 | Mitsubishi Tanabe Pharma Corp | Inhibitors of ?4 mediated cell adhesion |
| US6232322B1 (en) * | 1998-05-12 | 2001-05-15 | American Home Products Corporation | Biphenyl oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia |
| WO2001012183A1 (en) * | 1999-08-16 | 2001-02-22 | Merck & Co., Inc. | Heterocycle amides as cell adhesion inhibitors |
| EP1622886A2 (en) | 2003-04-30 | 2006-02-08 | The Institutes for Pharmaceutical Discovery, LLC | Substituted amino carboxylic acids as inhibitors of protein tyrosine phosphatase-1b |
| KR20060006954A (ko) | 2003-04-30 | 2006-01-20 | 디 인스티튜트스 포 파마슈티컬 디스커버리, 엘엘씨 | 단백질 티로신 포스파타제-１ｂ 억제제로서의 페닐 치환된카르복실산 |
| JP2008520693A (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 | プロテインチロシンホスファターゼ阻害剤としての置換アミノ酸 |
-
2004
- 2004-04-30 EP EP04751192A patent/EP1622886A2/en not_active Withdrawn
- 2004-04-30 BR BRPI0409924-9A patent/BRPI0409924A/pt not_active IP Right Cessation
- 2004-04-30 CA CA002523718A patent/CA2523718A1/en not_active Abandoned
- 2004-04-30 EA EA200501715A patent/EA200501715A1/ru unknown
- 2004-04-30 KR KR1020057020619A patent/KR20050115337A/ko not_active Withdrawn
- 2004-04-30 US US10/835,817 patent/US7358248B2/en not_active Expired - Fee Related
- 2004-04-30 JP JP2006514243A patent/JP2006525364A/ja not_active Abandoned
- 2004-04-30 RS YUP-2005/0814A patent/RS20050814A/sr unknown
- 2004-04-30 AU AU2004236247A patent/AU2004236247B2/en not_active Expired - Fee Related
- 2004-04-30 MX MXPA05011537A patent/MXPA05011537A/es not_active Application Discontinuation
- 2004-04-30 WO PCT/US2004/013700 patent/WO2004099171A2/en not_active Ceased
- 2004-04-30 CN CNA2004800184743A patent/CN1812979A/zh active Pending
-
2005
- 2005-10-25 NO NO20054958A patent/NO20054958L/no not_active Application Discontinuation
- 2005-11-29 ZA ZA200509630A patent/ZA200509630B/en unknown
- 2005-11-30 CO CO05121629A patent/CO5700733A2/es not_active Application Discontinuation
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