SK8732003A3 - Isoindolin-1-one glucokinase activators - Google Patents

Isoindolin-1-one glucokinase activators Download PDF

Info

Publication number: SK8732003A3
Authority: SK; Slovakia
Prior art keywords: oxo; cyclohexyl; dihydro; propionamide; isoindol
Prior art date: 2000-12-13

Application number

SK873-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Kevin Richard Guertin

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

2000-12-13

Filing date

2001-12-07

Publication date

2004-04-06

2001-12-07 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2004-04-06 Publication of SK8732003A3 publication Critical patent/SK8732003A3/sk

Links

PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 title claims description 6
102000030595 Glucokinase Human genes 0.000 title abstract description 44
108010021582 Glucokinase Proteins 0.000 title abstract description 44
239000012190 activator Substances 0.000 title abstract description 15
-1 Isoindolin-1-one-substituted propionamide Chemical class 0.000 claims abstract description 110
208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 13
238000011282 treatment Methods 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 89
229940080818 propionamide Drugs 0.000 claims description 86
238000000034 method Methods 0.000 claims description 54
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
229910052799 carbon Inorganic materials 0.000 claims description 40
125000001072 heteroaryl group Chemical group 0.000 claims description 40
230000008878 coupling Effects 0.000 claims description 35
238000010168 coupling process Methods 0.000 claims description 35
238000005859 coupling reaction Methods 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 29
150000001721 carbon Chemical group 0.000 claims description 26
229910052757 nitrogen Chemical group 0.000 claims description 26
125000005843 halogen group Chemical group 0.000 claims description 20
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 15
125000005842 heteroatom Chemical group 0.000 claims description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
125000002950 monocyclic group Chemical group 0.000 claims description 12
HAZJQNXTVYBGMP-QGZVFWFLSA-N (2r)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound O=C([C@@H](CC1CCCCC1)N1C(C2=CC=CC=C2C1)=O)NC1=NC=CS1 HAZJQNXTVYBGMP-QGZVFWFLSA-N 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 11
150000001408 amides Chemical class 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
239000001301 oxygen Chemical group 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
125000000335 thiazolyl group Chemical group 0.000 claims description 8
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 7
230000008569 process Effects 0.000 claims description 7
125000003373 pyrazinyl group Chemical group 0.000 claims description 7
125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
VIPWGMMDZOTSGY-IBGZPJMESA-N (2s)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)-n-pyridin-2-ylpropanamide Chemical compound O=C([C@H](CC1CCCCC1)N1C(C2=CC=CC=C2C1)=O)NC1=CC=CC=N1 VIPWGMMDZOTSGY-IBGZPJMESA-N 0.000 claims description 5
239000002671 adjuvant Substances 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
VPMSFNVPKXVXRA-UHFFFAOYSA-N n-(5-chloro-1,3-thiazol-2-yl)-3-cyclopentyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound S1C(Cl)=CN=C1NC(=O)C(N1C(C2=CC=CC=C2C1)=O)CC1CCCC1 VPMSFNVPKXVXRA-UHFFFAOYSA-N 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
AVZFDRVTBXTFED-LJQANCHMSA-N (2r)-n-(5-bromopyridin-2-yl)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound N1=CC(Br)=CC=C1NC(=O)[C@H](N1C(C2=CC=CC=C2C1)=O)CC1CCCCC1 AVZFDRVTBXTFED-LJQANCHMSA-N 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
SGQYBUJEJYXKCH-UHFFFAOYSA-N n-(1,3-thiazol-2-yl)propanamide Chemical compound CCC(=O)NC1=NC=CS1 SGQYBUJEJYXKCH-UHFFFAOYSA-N 0.000 claims description 4
VEMZDALOYZQAEW-QHCPKHFHSA-N (2s)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)-n-quinolin-2-ylpropanamide Chemical compound C([C@@H](C(NC=1N=C2C=CC=CC2=CC=1)=O)N1C(C2=CC=CC=C2C1)=O)C1CCCCC1 VEMZDALOYZQAEW-QHCPKHFHSA-N 0.000 claims description 3
BVNOVXGXNDLFON-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(4-methylsulfonyl-3-oxo-1h-isoindol-2-yl)-n-pyrazin-2-ylpropanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)S(=O)(=O)C)C(=O)NC=1N=CC=NC=1)C1CCCCC1 BVNOVXGXNDLFON-KRWDZBQOSA-N 0.000 claims description 3
FSHQEAUMFQXYOM-SFHVURJKSA-N (2s)-3-cyclohexyl-2-(7-methylsulfonyl-3-oxo-1h-isoindol-2-yl)-n-pyrazin-2-ylpropanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)S(=O)(=O)C)C(=O)NC=1N=CC=NC=1)C1CCCCC1 FSHQEAUMFQXYOM-SFHVURJKSA-N 0.000 claims description 3
ABUMTHLKVAXGJG-SFHVURJKSA-N (2s)-3-cyclohexyl-2-(7-methylsulfonyl-3-oxo-1h-isoindol-2-yl)-n-pyrimidin-4-ylpropanamide Chemical compound C([C@H](N1C(=O)C=2C=CC=C(C=2C1)S(=O)(=O)C)C(=O)NC=1N=CN=CC=1)C1CCCCC1 ABUMTHLKVAXGJG-SFHVURJKSA-N 0.000 claims description 3
HSVROUFTDPBEOI-FQEVSTJZSA-N (2s)-3-cyclohexyl-n-(4-methylpyridin-2-yl)-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound CC1=CC=NC(NC(=O)[C@H](CC2CCCCC2)N2C(C3=CC=CC=C3C2)=O)=C1 HSVROUFTDPBEOI-FQEVSTJZSA-N 0.000 claims description 3
HEMJGYNZNHUXMQ-FQEVSTJZSA-N (2s)-n-(1,3-benzoxazol-2-yl)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C([C@@H](C(NC=1OC2=CC=CC=C2N=1)=O)N1C(C2=CC=CC=C2C1)=O)C1CCCCC1 HEMJGYNZNHUXMQ-FQEVSTJZSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
238000011321 prophylaxis Methods 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 3
FXJNEBZFBPOSTM-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(4-methylsulfonyl-3-oxo-1h-isoindol-2-yl)-n-pyrimidin-4-ylpropanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)S(=O)(=O)C)C(=O)NC=1N=CN=CC=1)C1CCCCC1 FXJNEBZFBPOSTM-KRWDZBQOSA-N 0.000 claims description 2
JKHHPJPIEXQNBA-FQEVSTJZSA-N (2s)-n-(1,3-benzothiazol-2-yl)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C([C@@H](C(NC=1SC2=CC=CC=C2N=1)=O)N1C(C2=CC=CC=C2C1)=O)C1CCCCC1 JKHHPJPIEXQNBA-FQEVSTJZSA-N 0.000 claims description 2
JFZLHUCEJYRSNM-HNNXBMFYSA-N (2s)-n-(5-chloro-1,3-thiazol-2-yl)-3-cyclohexyl-2-(4-fluoro-3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)F)C(=O)NC=1SC(Cl)=CN=1)C1CCCCC1 JFZLHUCEJYRSNM-HNNXBMFYSA-N 0.000 claims description 2
XDZPUUOXMDFXIF-IBGZPJMESA-N (2s)-n-(5-chloropyridin-2-yl)-3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)[C@@H](N1C(C2=CC=CC=C2C1)=O)CC1CCCCC1 XDZPUUOXMDFXIF-IBGZPJMESA-N 0.000 claims description 2
PLENEAJJYFHWBP-HNNXBMFYSA-N (2s)-n-cyclohexyl-n-(2-methylpyrimidin-4-yl)-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound O=C([C@@H](N1C(C2=CC=CC=C2C1)=O)C)N(C=1N=C(C)N=CC=1)C1CCCCC1 PLENEAJJYFHWBP-HNNXBMFYSA-N 0.000 claims description 2
MCSTZKDFCAKYAJ-UHFFFAOYSA-N 3-cyclohexyl-2-(3-oxo-1h-isoindol-2-yl)-n-pyrimidin-4-ylpropanamide Chemical compound C1CCCCC1CC(N1C(C2=CC=CC=C2C1)=O)C(=O)NC1=CC=NC=N1 MCSTZKDFCAKYAJ-UHFFFAOYSA-N 0.000 claims description 2
BHGICAYVWJMPOK-UHFFFAOYSA-N 3-cyclooctyl-2-(3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1CCCCCCC1CC(N1C(C2=CC=CC=C2C1)=O)C(=O)NC1=NC=CS1 BHGICAYVWJMPOK-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000013543 active substance Substances 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
NSCIJCDEXRVCMK-UHFFFAOYSA-N n-(5-chloro-1,3-thiazol-2-yl)-3-cycloheptyl-2-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound S1C(Cl)=CN=C1NC(=O)C(N1C(C2=CC=CC=C2C1)=O)CC1CCCCCC1 NSCIJCDEXRVCMK-UHFFFAOYSA-N 0.000 claims description 2
230000000069 prophylactic effect Effects 0.000 claims description 2
AESJIZQMLZJCIX-KRWDZBQOSA-N (2s)-3-cyclohexyl-2-(4-fluoro-3-oxo-1h-isoindol-2-yl)-n-pyrazin-2-ylpropanamide Chemical compound C([C@H](N1CC=2C=CC=C(C=2C1=O)F)C(=O)NC=1N=CC=NC=1)C1CCCCC1 AESJIZQMLZJCIX-KRWDZBQOSA-N 0.000 claims 1
PIINXYKJQGMIOZ-UHFFFAOYSA-N 1,2-dipyridin-2-ylethane-1,2-dione Chemical compound C=1C=CC=NC=1C(=O)C(=O)C1=CC=CC=N1 PIINXYKJQGMIOZ-UHFFFAOYSA-N 0.000 claims 1
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125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
230000003914 insulin secretion Effects 0.000 abstract description 6
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230000035772 mutation Effects 0.000 description 1
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DWKULHYELSMWDJ-UHFFFAOYSA-N n-[3-[1-[(2-chloro-6-fluorophenyl)methyl]benzimidazol-2-yl]propyl]-2-methoxyacetamide Chemical compound COCC(=O)NCCCC1=NC2=CC=CC=C2N1CC1=C(F)C=CC=C1Cl DWKULHYELSMWDJ-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
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238000000746 purification Methods 0.000 description 1
150000003216 pyrazines Chemical class 0.000 description 1
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RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
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GACTWZZMVMUKNG-ZXXMMSQZSA-N sorbitol 6-phosphate Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)COP(O)(O)=O GACTWZZMVMUKNG-ZXXMMSQZSA-N 0.000 description 1
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WAPJVSYAZYVYAB-UHFFFAOYSA-N tert-butyl 2-(benzhydrylideneamino)-3-cycloheptylpropanoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=NC(C(=O)OC(C)(C)C)CC1CCCCCC1 WAPJVSYAZYVYAB-UHFFFAOYSA-N 0.000 description 1
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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
230000000699 topical effect Effects 0.000 description 1
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230000009261 transgenic effect Effects 0.000 description 1
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239000003643 water by type Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (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)
Engineering & Computer Science (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Hematology (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Breeding Of Plants And Reproduction By Means Of Culturing (AREA)

SK873-2003A 2000-12-13 2001-12-07 Isoindolin-1-one glucokinase activators SK8732003A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US25527300P	2000-12-13	2000-12-13
US31871501P	2001-09-13	2001-09-13
PCT/EP2001/014404 WO2002048106A2 (en)	2000-12-13	2001-12-07	Isoindolin-1-one glucokinase activators

Publications (1)

Publication Number	Publication Date
SK8732003A3 true SK8732003A3 (en)	2004-04-06

Family

ID=26944583

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK873-2003A SK8732003A3 (en)	2000-12-13	2001-12-07	Isoindolin-1-one glucokinase activators

Country Status (35)

Country	Link
US (1)	US6482951B2 (cs)
EP (1)	EP1349856B1 (cs)
JP (1)	JP4021766B2 (cs)
KR (1)	KR100520651B1 (cs)
CN (1)	CN1247574C (cs)
AT (1)	ATE297922T1 (cs)
AU (2)	AU2002238415B2 (cs)
BG (1)	BG107903A (cs)
BR (1)	BR0116169A (cs)
CA (1)	CA2430579C (cs)
CY (1)	CY1105587T1 (cs)
CZ (1)	CZ20031882A3 (cs)
DE (1)	DE60111570T2 (cs)
DK (1)	DK1349856T3 (cs)
EG (1)	EG24358A (cs)
ES (1)	ES2243578T3 (cs)
HR (1)	HRP20030450B1 (cs)
HU (1)	HUP0400587A3 (cs)
IL (2)	IL156264A0 (cs)
MA (1)	MA26973A1 (cs)
MX (1)	MXPA03005170A (cs)
MY (1)	MY136741A (cs)
NO (1)	NO325810B1 (cs)
NZ (1)	NZ526236A (cs)
PA (1)	PA8534601A1 (cs)
PE (1)	PE20020593A1 (cs)
PL (1)	PL366006A1 (cs)
PT (1)	PT1349856E (cs)
RS (1)	RS50933B (cs)
RU (1)	RU2249590C2 (cs)
SI (1)	SI1349856T1 (cs)
SK (1)	SK8732003A3 (cs)
TW (1)	TWI294876B (cs)
UY (1)	UY27069A1 (cs)
WO (1)	WO2002048106A2 (cs)

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Publication number	Publication date
JP2004521095A (ja)	2004-07-15
MXPA03005170A (es)	2003-09-22
HRP20030450B1 (en)	2006-02-28
KR20030064817A (ko)	2003-08-02
PT1349856E (pt)	2005-09-30
DE60111570T2 (de)	2006-05-11
HRP20030450A2 (en)	2005-04-30
ATE297922T1 (de)	2005-07-15
RS50933B (sr)	2010-08-31
IL156264A (en)	2010-11-30
SI1349856T1 (en)	2005-10-31
CN1247574C (zh)	2006-03-29
HUP0400587A3 (en)	2011-03-28
RU2249590C2 (ru)	2005-04-10
NO20032674L (no)	2003-06-12
NO20032674D0 (no)	2003-06-12
US20020082260A1 (en)	2002-06-27
BG107903A (bg)	2004-02-27
DK1349856T3 (da)	2005-10-17
PA8534601A1 (es)	2002-08-26
NZ526236A (en)	2004-12-24
CA2430579A1 (en)	2002-06-20
BR0116169A (pt)	2003-12-23
PL366006A1 (en)	2005-01-24
YU47703A (sh)	2006-05-25
CY1105587T1 (el)	2010-07-28
CN1481382A (zh)	2004-03-10
UY27069A1 (es)	2002-07-31
HUP0400587A2 (hu)	2004-06-28
HK1063314A1 (en)	2004-12-24
AU2002238415B2 (en)	2007-01-04
EG24358A (en)	2009-03-04
WO2002048106A3 (en)	2002-11-28
CZ20031882A3 (cs)	2003-12-17
JP4021766B2 (ja)	2007-12-12
AU3841502A (en)	2002-06-24
PE20020593A1 (es)	2002-07-06
MY136741A (en)	2008-11-28
WO2002048106A2 (en)	2002-06-20
MA26973A1 (fr)	2004-12-20
US6482951B2 (en)	2002-11-19
TWI294876B (en)	2008-03-21
EP1349856A2 (en)	2003-10-08
NO325810B1 (no)	2008-07-21
IL156264A0 (en)	2004-01-04
CA2430579C (en)	2010-01-26
ES2243578T3 (es)	2005-12-01
DE60111570D1 (de)	2005-07-21
EP1349856B1 (en)	2005-06-15
KR100520651B1 (ko)	2005-10-11

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Publication	Publication Date	Title
JP4021766B2 (ja)	2007-12-12	イソインドリン−１−オンのグルコキナーゼアクチベーター
AU2002238415A1 (en)	2002-08-29	Isoindolin-1-one glucokinase activators
EP1549638B1 (en)	2007-10-03	Indole-3-carboxamides as glucokinase (gk) activators
JP3971189B2 (ja)	2007-09-05	ｐ−アミノ置換フェニルアミドグルコキナーゼ活性化物質
AU2001265914A1 (en)	2002-02-07	Para-amine substituted phenylamide glucokinase activators
MXPA02010745A (es)	2003-03-10	Activadores de glucocinasa heteroaromaticos de alquinil-fenilo.
ZA200304265B (en)	2004-08-30	Isoindolin-1-one glucokinase activators.