ZA200203829B - Trans olefinic glucokinase activators. - Google Patents
Trans olefinic glucokinase activators. Download PDFInfo
- Publication number
- ZA200203829B ZA200203829B ZA200203829A ZA200203829A ZA200203829B ZA 200203829 B ZA200203829 B ZA 200203829B ZA 200203829 A ZA200203829 A ZA 200203829A ZA 200203829 A ZA200203829 A ZA 200203829A ZA 200203829 B ZA200203829 B ZA 200203829B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- methanesulfonyl
- compound
- thiazol
- acrylamide
- Prior art date
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- 102000030595 Glucokinase Human genes 0.000 title description 23
- 108010021582 Glucokinase Proteins 0.000 title description 23
- 239000012190 activator Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- -1 sulfonyl methyl Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 13
- 229910052757 nitrogen Chemical group 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 7
- 239000000126 substance Substances 0.000 claims 5
- LQQZQDWVRVMLMR-GXDHUFHOSA-N (e)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCC1 LQQZQDWVRVMLMR-GXDHUFHOSA-N 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- OXYOTPLSQLGBJL-SFQUDFHCSA-N methyl 2-[[(e)-4-cyclopentyl-2-(4-methylsulfonylphenyl)but-2-enoyl]amino]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)C(=C\CC2CCCC2)\C=2C=CC(=CC=2)S(C)(=O)=O)=N1 OXYOTPLSQLGBJL-SFQUDFHCSA-N 0.000 claims 3
- OYDGJORZWPQIQE-FOWTUZBSSA-N (e)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-pyridin-2-ylprop-2-enamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1N=CC=CC=1)=C/C1CCCC1 OYDGJORZWPQIQE-FOWTUZBSSA-N 0.000 claims 2
- BVPVGKONEFCGEO-NBVRZTHBSA-N (e)-3-cycloheptyl-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCCCC1 BVPVGKONEFCGEO-NBVRZTHBSA-N 0.000 claims 2
- FICFIIMMJODLNW-RVDMUPIBSA-N (e)-3-cyclohexyl-2-(4-methylsulfonyl-3-nitrophenyl)-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=C([N+]([O-])=O)C(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCCC1 FICFIIMMJODLNW-RVDMUPIBSA-N 0.000 claims 2
- SANUEZHQGWAUCN-GHRIWEEISA-N (e)-3-cyclohexyl-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCCC1 SANUEZHQGWAUCN-GHRIWEEISA-N 0.000 claims 2
- BCHXPOUTSCJBCH-FOWTUZBSSA-N (e)-3-cyclopentyl-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCC1 BCHXPOUTSCJBCH-FOWTUZBSSA-N 0.000 claims 2
- MWTBIDPRXILOJG-OVCLIPMQSA-N (e)-4-cyclopentyl-2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]-n-(1,3-thiazol-2-yl)but-2-enamide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/CC1CCCC1 MWTBIDPRXILOJG-OVCLIPMQSA-N 0.000 claims 2
- FDQAFURIAOKAFS-SFQUDFHCSA-N (e)-n-(5-bromo-1,3-thiazol-2-yl)-3-cycloheptyl-2-(4-methylsulfonylphenyl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC(Br)=CN=1)=C/C1CCCCCC1 FDQAFURIAOKAFS-SFQUDFHCSA-N 0.000 claims 2
- XZYIPDWUIQFWRL-GZTJUZNOSA-N (e)-n-(5-bromopyridin-2-yl)-3-cyclohexyl-2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1N=CC(Br)=CC=1)=C/C1CCCCC1 XZYIPDWUIQFWRL-GZTJUZNOSA-N 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- RRNQUGCUBMNGCT-GXDHUFHOSA-N (e)-2-(3-bromo-4-methylsulfonylphenyl)-3-cyclopentyl-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=C(Br)C(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCC1 RRNQUGCUBMNGCT-GXDHUFHOSA-N 0.000 claims 1
- UVLJGXZKAKBRDX-YIXHJXPBSA-N (e)-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)pent-2-enamide Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(=C/CC)\C(=O)NC1=NC=CS1 UVLJGXZKAKBRDX-YIXHJXPBSA-N 0.000 claims 1
- ABZFZZUCQFYLGH-GZTJUZNOSA-N (e)-2-[3-chloro-4-(methylsulfonylmethyl)phenyl]-3-cyclohexyl-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=C(Cl)C(CS(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCCC1 ABZFZZUCQFYLGH-GZTJUZNOSA-N 0.000 claims 1
- PMWNPODELRJITN-FOWTUZBSSA-N (e)-3-cycloheptyl-2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCCCC1 PMWNPODELRJITN-FOWTUZBSSA-N 0.000 claims 1
- ZJZSWZGPTJTHTP-GXDHUFHOSA-N (e)-3-cyclohexyl-2-(3,4-difluorophenyl)-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=C(F)C(F)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCCC1 ZJZSWZGPTJTHTP-GXDHUFHOSA-N 0.000 claims 1
- YSLZNYGGLOZLPM-RVDMUPIBSA-N (e)-3-cyclohexyl-2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCCC1 YSLZNYGGLOZLPM-RVDMUPIBSA-N 0.000 claims 1
- OMYYVTZOFGFXRH-GXDHUFHOSA-N (e)-3-cyclohexyl-n-(methylcarbamoyl)-2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C=1C=C(S(C)(=O)=O)C(C(F)(F)F)=CC=1/C(C(=O)NC(=O)NC)=C\C1CCCCC1 OMYYVTZOFGFXRH-GXDHUFHOSA-N 0.000 claims 1
- FAGVPXDHYNJFCC-XDJHFCHBSA-N (e)-3-cyclooctyl-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCCCCC1 FAGVPXDHYNJFCC-XDJHFCHBSA-N 0.000 claims 1
- LPANTTLHGJJATA-UKTHLTGXSA-N (e)-3-cyclopentyl-2-(3,4-dichlorophenyl)-n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/C1CCCC1 LPANTTLHGJJATA-UKTHLTGXSA-N 0.000 claims 1
- NNARSRDJXJIIAK-VGOFMYFVSA-N (e)-4-cyclopentyl-2-(3,4-difluorophenyl)-n-(1,3-thiazol-2-yl)but-2-enamide Chemical compound C1=C(F)C(F)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/CC1CCCC1 NNARSRDJXJIIAK-VGOFMYFVSA-N 0.000 claims 1
- COSUEEHOZUFBOZ-GZTJUZNOSA-N (e)-4-cyclopentyl-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)but-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC=CN=1)=C/CC1CCCC1 COSUEEHOZUFBOZ-GZTJUZNOSA-N 0.000 claims 1
- UVUKJGDYSUGMBE-GXDHUFHOSA-N (e)-4-methyl-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)pent-2-enamide Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(=C/C(C)C)\C(=O)NC1=NC=CS1 UVUKJGDYSUGMBE-GXDHUFHOSA-N 0.000 claims 1
- XOWGQNFXTWHUGV-XNTDXEJSSA-N (e)-n-(5-bromo-1,3-thiazol-2-yl)-3-cycloheptyl-2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC(Br)=CN=1)=C/C1CCCCCC1 XOWGQNFXTWHUGV-XNTDXEJSSA-N 0.000 claims 1
- DAFVQCLKJHTEOW-NTEUORMPSA-N (e)-n-(5-bromo-1,3-thiazol-2-yl)-3-cyclohexyl-2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC(Br)=CN=1)=C/C1CCCCC1 DAFVQCLKJHTEOW-NTEUORMPSA-N 0.000 claims 1
- JOISSXZRHSAVRM-XNTDXEJSSA-N (e)-n-(5-bromo-1,3-thiazol-2-yl)-3-cyclopentyl-2-(4-methylsulfonylphenyl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC(Br)=CN=1)=C/C1CCCC1 JOISSXZRHSAVRM-XNTDXEJSSA-N 0.000 claims 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- AYMLWTSRYUWEOX-QGOAFFKASA-N ethyl 2-[[(e)-4-cyclopentyl-2-(4-methylsulfonylphenyl)but-2-enoyl]amino]-1,3-thiazole-5-carboxylate Chemical compound S1C(C(=O)OCC)=CN=C1NC(=O)C(\C=1C=CC(=CC=1)S(C)(=O)=O)=C\CC1CCCC1 AYMLWTSRYUWEOX-QGOAFFKASA-N 0.000 claims 1
- 239000011148 porous material Substances 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 description 15
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 11
- 239000008103 glucose Substances 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 4
- 230000003914 insulin secretion Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 102000005548 Hexokinase Human genes 0.000 description 3
- 108700040460 Hexokinases Proteins 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 210000003494 hepatocyte Anatomy 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 101150109586 Gk gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 208000035180 MODY Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 210000003719 b-lymphocyte Anatomy 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
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- 206010012601 diabetes mellitus Diseases 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 230000014101 glucose homeostasis Effects 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
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- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical class O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- CSBZOZVZNPXUDW-UHFFFAOYSA-N benzyl carbamoyl carbonate Chemical group NC(=O)OC(=O)OCC1=CC=CC=C1 CSBZOZVZNPXUDW-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical class ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000009229 glucose formation Effects 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000004777 loss-of-function mutation Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 210000004738 parenchymal cell Anatomy 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- UIYOVVYZPVVUMJ-UHFFFAOYSA-N tert-butyl carbamoyl carbonate Chemical group CC(C)(C)OC(=O)OC(N)=O UIYOVVYZPVVUMJ-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
- 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
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/50—Y being a hydrogen or an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17078399P | 1999-12-15 | 1999-12-15 |
Publications (1)
Publication Number | Publication Date |
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ZA200203829B true ZA200203829B (en) | 2003-08-14 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200203829A ZA200203829B (en) | 1999-12-15 | 2002-05-14 | Trans olefinic glucokinase activators. |
Country Status (33)
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US (1) | US6353111B1 (zh) |
EP (1) | EP1242397B1 (zh) |
JP (1) | JP3824936B2 (zh) |
KR (1) | KR100502032B1 (zh) |
CN (1) | CN1185219C (zh) |
AR (1) | AR032752A1 (zh) |
AT (1) | ATE305461T1 (zh) |
AU (1) | AU781029B2 (zh) |
CA (1) | CA2392903C (zh) |
CO (1) | CO5050295A1 (zh) |
CZ (1) | CZ20022412A3 (zh) |
DE (1) | DE60022903T2 (zh) |
DK (1) | DK1242397T3 (zh) |
ES (1) | ES2249322T3 (zh) |
GC (1) | GC0000264A (zh) |
HK (1) | HK1054383B (zh) |
HR (1) | HRP20020514A2 (zh) |
HU (1) | HUP0203753A3 (zh) |
IL (2) | IL150083A0 (zh) |
JO (1) | JO2180B1 (zh) |
MA (1) | MA26855A1 (zh) |
MX (1) | MXPA02005874A (zh) |
MY (1) | MY125484A (zh) |
NO (1) | NO323142B1 (zh) |
NZ (1) | NZ518974A (zh) |
PE (1) | PE20011022A1 (zh) |
PL (1) | PL355815A1 (zh) |
RU (1) | RU2245332C2 (zh) |
TW (1) | TWI262916B (zh) |
UY (1) | UY26483A1 (zh) |
WO (1) | WO2001044216A1 (zh) |
YU (1) | YU41402A (zh) |
ZA (1) | ZA200203829B (zh) |
Families Citing this family (64)
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SE0102299D0 (sv) | 2001-06-26 | 2001-06-26 | Astrazeneca Ab | Compounds |
SE0102300D0 (sv) * | 2001-06-26 | 2001-06-26 | Astrazeneca Ab | Compounds |
SE0102764D0 (sv) * | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
KR101018318B1 (ko) | 2001-12-21 | 2011-03-04 | 노보 노르디스크 에이/에스 | Gk 활성제로서의 아미드 유도체 |
EP1485107A1 (en) | 2002-02-11 | 2004-12-15 | Vertex Pharmaceuticals Incorporated | Phospholipids as caspase inhibitor prodrugs |
JP4419571B2 (ja) | 2002-03-26 | 2010-02-24 | 萬有製薬株式会社 | 新規アミノベンズアミド誘導体 |
CN1678311A (zh) | 2002-06-27 | 2005-10-05 | 诺沃挪第克公司 | 用作治疗剂的芳基羰基衍生物 |
MXPA05000130A (es) | 2002-06-27 | 2005-02-17 | Novo Nordisk As | Derivados de aril-carbonilo como agentes terapeuticos. |
KR20050074959A (ko) * | 2002-10-03 | 2005-07-19 | 노파르티스 아게 | 제ii형 당뇨병 치료에 유용한 글루코키나아제 활성인자로서의 치환된 (티아졸-2-일)-아미드 또는 술폰아미드 |
GB0226930D0 (en) * | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
GB0226931D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
PE20040801A1 (es) | 2002-12-12 | 2004-11-25 | Hoffmann La Roche | Derivados de pirazina y piridina 5-sustituidos como activadores de glucoquinasa |
WO2004063194A1 (en) * | 2003-01-06 | 2004-07-29 | Eli Lilly And Company | Heteroaryl compounds |
PL378117A1 (pl) * | 2003-02-11 | 2006-03-06 | Prosidion Limited | Tricyklopodstawione związki amidowe |
JP4621198B2 (ja) * | 2003-02-11 | 2011-01-26 | プロシディオン・リミテッド | トリ(シクロ)置換アミドグルコキナーゼ活性化化合物 |
CN102516240A (zh) | 2004-01-06 | 2012-06-27 | 诺和诺德公司 | 杂芳基脲及其作为葡糖激酶活化剂的用途 |
EP2048137A1 (en) | 2004-02-18 | 2009-04-15 | AstraZeneca AB | Benzamide derivatives and their use as glucokinase activating agents. |
EP1737870A1 (en) * | 2004-04-02 | 2007-01-03 | Novartis AG | Thiazolopyridine derivates, pharmaceutical conditions containing them and methods of treating glucokinase mediated conditions |
AU2005229416B2 (en) * | 2004-04-02 | 2009-03-26 | Novartis Ag | Sulfonamide-thiazolpyridine derivatives as glucokinase activators useful the treatment of type 2 diabetes |
CA2563192A1 (en) * | 2004-04-21 | 2005-11-03 | Prosidion Limited | Tri(cyclo) substituted amide compounds |
TW200600086A (en) | 2004-06-05 | 2006-01-01 | Astrazeneca Ab | Chemical compound |
US20080026987A1 (en) * | 2004-06-17 | 2008-01-31 | Novo Nordisk A/S | Use of Liver-Selective Glucokinase Activators |
WO2006016194A1 (en) * | 2004-08-12 | 2006-02-16 | Prosidion Limited | Substituted phenylacetamides and their use as glucokinase activators |
EP1904466A1 (en) | 2005-07-08 | 2008-04-02 | Novo Nordisk A/S | Dicycloalkyl urea glucokinase activators |
EP1902052B1 (en) | 2005-07-09 | 2012-11-28 | AstraZeneca AB | Heteroaryl benzamide derivatives for use as glk activators in the treatment of diabetes |
EP1910317B1 (en) | 2005-07-20 | 2013-07-03 | Eli Lilly And Company | 1-amino linked compounds |
JP2007063225A (ja) * | 2005-09-01 | 2007-03-15 | Takeda Chem Ind Ltd | イミダゾピリジン化合物 |
CN101272784A (zh) | 2005-09-29 | 2008-09-24 | 塞诺菲-安万特股份有限公司 | 苯基-和吡啶基-1,2,4-噁二唑酮衍生物、它们的制备方法和它们作为药物的用途 |
GT200600429A (es) * | 2005-09-30 | 2007-04-30 | Compuestos organicos | |
GT200600428A (es) * | 2005-09-30 | 2007-05-21 | Compuestos organicos | |
EP1948644A1 (en) * | 2005-11-03 | 2008-07-30 | Prosidion Limited | Tricyclo substituted amides |
CN101312940B (zh) | 2005-11-17 | 2012-11-14 | 伊莱利利公司 | 胰高血糖素受体拮抗剂、制备和治疗用途 |
JP2009515997A (ja) * | 2005-11-18 | 2009-04-16 | タケダ サン ディエゴ インコーポレイテッド | グルコキナーゼ活性剤 |
JP5302012B2 (ja) | 2006-03-08 | 2013-10-02 | タケダ カリフォルニア インコーポレイテッド | グルコキナーゼ活性剤 |
PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
EP2049518B1 (en) * | 2006-05-31 | 2011-08-31 | Takeda San Diego, Inc. | Indazole and isoindole derivatives as glucokinase activating agents. |
WO2008024456A2 (en) | 2006-08-24 | 2008-02-28 | University Of Tennessee Research Foundation | Substituted acylanilides and methods of use thereof |
CL2007003061A1 (es) | 2006-10-26 | 2008-08-01 | Astrazeneca Ab | Compuestos derivados de 3,5-dioxi-benzamida; proceso de preparacion; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar una enfermedad mediada a traves de glk, tal como la diabetes tipo 2. |
US7902248B2 (en) * | 2006-12-14 | 2011-03-08 | Hoffmann-La Roche Inc. | Oxime glucokinase activators |
EP2091947A2 (en) | 2006-12-20 | 2009-08-26 | Takeda San Diego, Inc. | Glucokinase activators |
TW200831081A (en) | 2006-12-25 | 2008-08-01 | Kyorin Seiyaku Kk | Glucokinase activator |
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WO2009039944A1 (de) * | 2007-09-21 | 2009-04-02 | Sanofi-Aventis | Phenothiazin derivate mit doppelbindung, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
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BRPI0906888A2 (pt) | 2008-01-18 | 2015-11-03 | Astellas Pharma Inc | derivado de fenilacetamida |
PT2275414E (pt) * | 2008-04-28 | 2015-09-09 | Teijin Pharma Ltd | Derivado de amida do ácido ciclopentacrílico |
PE20141375A1 (es) | 2008-05-16 | 2014-10-23 | Takeda San Diego Inc | Activadores de glucoquinasa |
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NZ598232A (en) | 2009-07-31 | 2013-08-30 | Cadila Healthcare Ltd | Substituted benzamide derivatives as glucokinase (gk) activators |
KR100970871B1 (ko) * | 2009-11-30 | 2010-07-20 | 케이제이알디 (주) | 바닥재 어셈블리 및 바닥재의 시공방법 |
RU2551847C2 (ru) | 2009-12-04 | 2015-05-27 | Тайсо Фармасьютикал Ко., Лтд. | Производные 2-пиридона |
AU2011235212B2 (en) | 2010-03-31 | 2014-07-31 | The Scripps Research Institute | Reprogramming cells |
US9969683B2 (en) | 2012-07-13 | 2018-05-15 | Gtx, Inc. | Method of treating estrogen receptor (ER)-positive breast cancers with selective androgen receptor modulator (SARMS) |
US9622992B2 (en) | 2012-07-13 | 2017-04-18 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
EP3733170A1 (en) | 2012-07-13 | 2020-11-04 | Oncternal Therapeutics, Inc. | A method of treating androgen receptor (ar) -positive breast cancers with selective androgen receptor modulator (sarms) |
US10987334B2 (en) | 2012-07-13 | 2021-04-27 | University Of Tennessee Research Foundation | Method of treating ER mutant expressing breast cancers with selective androgen receptor modulators (SARMs) |
US10258596B2 (en) | 2012-07-13 | 2019-04-16 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
US10314807B2 (en) | 2012-07-13 | 2019-06-11 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
US9744149B2 (en) | 2012-07-13 | 2017-08-29 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
NO2921489T3 (zh) | 2012-11-13 | 2018-02-03 | ||
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GB8909574D0 (en) | 1989-04-26 | 1989-06-14 | Ici Plc | Chemical process |
US5169951A (en) | 1990-04-23 | 1992-12-08 | Ciba-Geigy Corporation | Process for preparing nematicidal compositions |
ES2226811T3 (es) * | 1999-03-29 | 2005-04-01 | F. Hoffmann-La Roche Ag | Activadores de glucoquinasa. |
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2000
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