HRP20040953A2 - Substituted phenylacetamides and their use as glucokinase activators - Google Patents

Substituted phenylacetamides and their use as glucokinase activators

Info

Publication number: HRP20040953A2
Authority: HR; Croatia
Prior art keywords: phenyl; propionamide; chloro; methanesulfonyl; cyclopentyl
Prior art date: 2002-04-26

Application number

HR20040953A

Other languages

English (en)

Croatian (hr)

Inventor

Lea Corbett Wendy

Joseph

Haynes Nancy-Ellen

Robert

Paige

Jagdish

Sarabu Remakanth

Wang Ka

Original Assignee

F. Hoffmann - La Roche Ag

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.)

2002-04-26

Filing date

2004-10-12

Publication date

2005-06-30

2004-10-12 Application filed by F. Hoffmann - La Roche Ag filed Critical F. Hoffmann - La Roche Ag

2005-06-30 Publication of HRP20040953A2 publication Critical patent/HRP20040953A2/hr

Links

102000030595 Glucokinase Human genes 0.000 title description 23
108010021582 Glucokinase Proteins 0.000 title description 23
239000012190 activator Substances 0.000 title description 4
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 title 1
238000006243 chemical reaction Methods 0.000 claims description 205
150000001875 compounds Chemical class 0.000 claims description 190
-1 amino, hydroxyamino Chemical group 0.000 claims description 148
238000000034 method Methods 0.000 claims description 117
125000000217 alkyl group Chemical group 0.000 claims description 81
229910052799 carbon Inorganic materials 0.000 claims description 77
150000001721 carbon Chemical group 0.000 claims description 63
125000004414 alkyl thio group Chemical group 0.000 claims description 45
125000004432 carbon atom Chemical group C* 0.000 claims description 45
125000005843 halogen group Chemical group 0.000 claims description 43
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
125000001072 heteroaryl group Chemical group 0.000 claims description 38
125000005842 heteroatom Chemical group 0.000 claims description 37
239000001257 hydrogen Substances 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 32
229940080818 propionamide Drugs 0.000 claims description 29
125000004093 cyano group Chemical group *C#N 0.000 claims description 28
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 26
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
125000003277 amino group Chemical group 0.000 claims description 23
229910052717 sulfur Inorganic materials 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 20
150000002431 hydrogen Chemical class 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 17
125000001309 chloro group Chemical group Cl* 0.000 claims description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
125000004434 sulfur atom Chemical group 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
239000011593 sulfur Substances 0.000 claims description 11
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 11
125000004043 oxo group Chemical group O=* 0.000 claims description 10
230000008569 process Effects 0.000 claims description 10
XEANIURBPHCHMG-SWLSCSKDSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-[(1r)-3-oxocyclopentyl]-n-pyrazin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC=NC=1)C[C@@H]1CC(=O)CC1 XEANIURBPHCHMG-SWLSCSKDSA-N 0.000 claims description 9
238000011282 treatment Methods 0.000 claims description 9
VBTKTLBFIDYEIU-PESDSKBTSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-(3-hydroxycyclopentyl)-n-pyrazin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC=NC=1)CC1CC(O)CC1 VBTKTLBFIDYEIU-PESDSKBTSA-N 0.000 claims description 8
SWKXDUCWTBCCAM-UHFFFAOYSA-N n-(5-bromopyrazin-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-(oxan-4-yl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(Br)=NC=1)CC1CCOCC1 SWKXDUCWTBCCAM-UHFFFAOYSA-N 0.000 claims description 8
XEANIURBPHCHMG-WPZCJLIBSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-(3-oxocyclopentyl)-n-pyrazin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC=NC=1)CC1CC(=O)CC1 XEANIURBPHCHMG-WPZCJLIBSA-N 0.000 claims description 7
XEANIURBPHCHMG-IUODEOHRSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-[(1s)-3-oxocyclopentyl]-n-pyrazin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC=NC=1)C[C@H]1CC(=O)CC1 XEANIURBPHCHMG-IUODEOHRSA-N 0.000 claims description 7
VIWCFBHXOBWYBR-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-(3-methoxyiminocyclopentyl)-n-pyrazin-2-ylpropanamide Chemical compound C1C(=NOC)CCC1CC(C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)C(=O)NC1=CN=CC=N1 VIWCFBHXOBWYBR-UHFFFAOYSA-N 0.000 claims description 7
ITZHOKQQDWESOK-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-n-(5-cyanopyrazin-2-yl)-3-(oxan-4-yl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(=NC=1)C#N)CC1CCOCC1 ITZHOKQQDWESOK-UHFFFAOYSA-N 0.000 claims description 7
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
POINJIWOOVXOGT-UHFFFAOYSA-N n-(5-bromopyrazin-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-(3-methoxyiminocyclopentyl)propanamide Chemical compound C1C(=NOC)CCC1CC(C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)C(=O)NC1=CN=C(Br)C=N1 POINJIWOOVXOGT-UHFFFAOYSA-N 0.000 claims description 7
UUQXKMLSWUNATN-UHFFFAOYSA-N n-(5-bromopyrazin-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-(3-oxocyclopentyl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(Br)=NC=1)CC1CC(=O)CC1 UUQXKMLSWUNATN-UHFFFAOYSA-N 0.000 claims description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
NFRSYKWDHVNVAS-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-n-(5-methylpyrazin-2-yl)-3-(4-oxocyclohexyl)propanamide Chemical compound C1=NC(C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCC(=O)CC1 NFRSYKWDHVNVAS-QGZVFWFLSA-N 0.000 claims description 6
IICNFYZYAVVBJL-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-(3-oxocyclopentyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CC(=O)CC1 IICNFYZYAVVBJL-UHFFFAOYSA-N 0.000 claims description 6
XEANIURBPHCHMG-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-(3-oxocyclopentyl)-n-pyrazin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC=NC=1)CC1CC(=O)CC1 XEANIURBPHCHMG-UHFFFAOYSA-N 0.000 claims description 6
JDQPFGIJIRATKC-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-N-[5-[(E)-N'-hydroxycarbamimidoyl]pyrazin-2-yl]-3-(oxan-4-yl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(=NC=1)C(=N)NO)CC1CCOCC1 JDQPFGIJIRATKC-UHFFFAOYSA-N 0.000 claims description 6
KKECPVQKQAKOSW-UHFFFAOYSA-N 3-(2-hydroxycyclopentyl)-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC=CN=1)CC1C(O)CCC1 KKECPVQKQAKOSW-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000001246 bromo group Chemical group Br* 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
KVABINFFCIRQHU-ARLHGKGLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-(2-oxocyclopentyl)-n-pyrazin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC=NC=1)CC1C(=O)CCC1 KVABINFFCIRQHU-ARLHGKGLSA-N 0.000 claims description 5
UXTHNBRTTHVSCD-WPZCJLIBSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-n-(5-chloropyrazin-2-yl)-3-(4-hydroxyiminocyclohexyl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(Cl)=NC=1)CC1CCC(=NO)CC1 UXTHNBRTTHVSCD-WPZCJLIBSA-N 0.000 claims description 5
WVFZLCPVPANBTF-WPZCJLIBSA-N (2r)-n-(5-bromopyrazin-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-(4-hydroxyiminocyclohexyl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(Br)=NC=1)CC1CCC(=NO)CC1 WVFZLCPVPANBTF-WPZCJLIBSA-N 0.000 claims description 5
RYCHCSPJUJAUPK-OAHLLOKOSA-N (2r)-n-(5-bromopyrazin-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-(4-oxocyclohexyl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(Br)=NC=1)CC1CCC(=O)CC1 RYCHCSPJUJAUPK-OAHLLOKOSA-N 0.000 claims description 5
QTMMVTMICQNVFT-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-(2-hydroxycyclopentyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound OC1CCCC1CC(C=1C=C(Cl)C(Cl)=CC=1)C(=O)NC1=NC=CS1 QTMMVTMICQNVFT-UHFFFAOYSA-N 0.000 claims description 5
OKILZKXLQIJBNV-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-(2-hydroxycyclopentyl)-n-(methylcarbamoyl)propanamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(=O)NC(=O)NC)CC1CCCC1O OKILZKXLQIJBNV-UHFFFAOYSA-N 0.000 claims description 5
NTQYHMBFILUHFC-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-(3-hydroxycyclopentyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1C(O)CCC1CC(C=1C=C(Cl)C(Cl)=CC=1)C(=O)NC1=NC=CS1 NTQYHMBFILUHFC-UHFFFAOYSA-N 0.000 claims description 5
AZMIAZRFFYPCGH-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-(3-hydroxycyclopentyl)-n-(methylcarbamoyl)propanamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(=O)NC(=O)NC)CC1CCC(O)C1 AZMIAZRFFYPCGH-UHFFFAOYSA-N 0.000 claims description 5
NAVGMQXRKUDDLW-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-(2-hydroxyiminocyclopentyl)-n-pyrazin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC=NC=1)CC1C(=NO)CCC1 NAVGMQXRKUDDLW-UHFFFAOYSA-N 0.000 claims description 5
SEABPIZPZOCJSL-UHFFFAOYSA-N 3-(3-hydroxycyclopentyl)-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CC(O)CC1 SEABPIZPZOCJSL-UHFFFAOYSA-N 0.000 claims description 5
OJNXQSCXYYQIRL-UHFFFAOYSA-N 6-[[2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]-3-(oxan-2-yl)propanoyl]amino]pyridine-3-carboxylic acid Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(=CC=1)C(O)=O)CC1OCCCC1 OJNXQSCXYYQIRL-UHFFFAOYSA-N 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
SJRODUKFGFUHDL-UHFFFAOYSA-N methyl 6-[[2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]-3-(oxan-2-yl)propanoyl]amino]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1NC(=O)C(C=1C=C(C(=CC=1)S(C)(=O)=O)C(F)(F)F)CC1OCCCC1 SJRODUKFGFUHDL-UHFFFAOYSA-N 0.000 claims description 5
WVFZLCPVPANBTF-UHFFFAOYSA-N n-(5-bromopyrazin-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-(4-hydroxyiminocyclohexyl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(Br)=NC=1)CC1CCC(=NO)CC1 WVFZLCPVPANBTF-UHFFFAOYSA-N 0.000 claims description 5
RYCHCSPJUJAUPK-UHFFFAOYSA-N n-(5-bromopyrazin-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-(4-oxocyclohexyl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(Br)=NC=1)CC1CCC(=O)CC1 RYCHCSPJUJAUPK-UHFFFAOYSA-N 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
BOHHUFXPWFWWMG-ZGTCLIOFSA-N (2r)-2-(3,4-dichlorophenyl)-3-(oxan-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1[C@H](C(=O)NC=1SC=CN=1)CC1OCCCC1 BOHHUFXPWFWWMG-ZGTCLIOFSA-N 0.000 claims description 4
QQXUDIFSYPJALF-PESDSKBTSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-n-(5-chloropyrazin-2-yl)-3-(4-hydroxycyclohexyl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(Cl)=NC=1)CC1CCC(O)CC1 QQXUDIFSYPJALF-PESDSKBTSA-N 0.000 claims description 4
DEBCWOPFQYWQIX-OAHLLOKOSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-n-(5-chloropyrazin-2-yl)-3-(4-oxocyclohexyl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(Cl)=NC=1)CC1CCC(=O)CC1 DEBCWOPFQYWQIX-OAHLLOKOSA-N 0.000 claims description 4
YWVFWBLBUZOKBE-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-(2,2-difluorocyclopentyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound FC1(F)CCCC1CC(C=1C=C(Cl)C(Cl)=CC=1)C(=O)NC1=NC=CS1 YWVFWBLBUZOKBE-UHFFFAOYSA-N 0.000 claims description 4
NRTLMTJMKHBJAQ-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-(2-oxocyclopentyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(C(=O)NC=1SC=CN=1)CC1C(=O)CCC1 NRTLMTJMKHBJAQ-UHFFFAOYSA-N 0.000 claims description 4
MXGYNKOSFZQKKW-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-(3,3-difluorocyclopentyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1C(F)(F)CCC1CC(C=1C=C(Cl)C(Cl)=CC=1)C(=O)NC1=NC=CS1 MXGYNKOSFZQKKW-UHFFFAOYSA-N 0.000 claims description 4
QDGLBFNRXFXDQQ-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-(3-fluorocyclopentyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1C(F)CCC1CC(C=1C=C(Cl)C(Cl)=CC=1)C(=O)NC1=NC=CS1 QDGLBFNRXFXDQQ-UHFFFAOYSA-N 0.000 claims description 4
IRANGAJQIKKLAM-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-(3-methoxycyclopentyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1C(OC)CCC1CC(C=1C=C(Cl)C(Cl)=CC=1)C(=O)NC1=NC=CS1 IRANGAJQIKKLAM-UHFFFAOYSA-N 0.000 claims description 4
MDGRKUBRJZTHCC-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-(3-methoxyiminocyclopentyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1C(=NOC)CCC1CC(C=1C=C(Cl)C(Cl)=CC=1)C(=O)NC1=NC=CS1 MDGRKUBRJZTHCC-UHFFFAOYSA-N 0.000 claims description 4
ZWKHJNJQQRISKT-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-n-(methylcarbamoyl)-3-(3-oxocyclopentyl)propanamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(=O)NC(=O)NC)CC1CCC(=O)C1 ZWKHJNJQQRISKT-UHFFFAOYSA-N 0.000 claims description 4
PQQPOIDYDLETIS-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-n-(methylcarbamoyl)-3-(oxan-2-yl)propanamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(=O)NC(=O)NC)CC1CCCCO1 PQQPOIDYDLETIS-UHFFFAOYSA-N 0.000 claims description 4
SEUGWXDNBUQZJY-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-n-(methylcarbamoyl)-3-(oxolan-2-yl)propanamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(=O)NC(=O)NC)CC1CCCO1 SEUGWXDNBUQZJY-UHFFFAOYSA-N 0.000 claims description 4
ZTUPVKQZCNWTPJ-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-(2-methoxyiminocyclopentyl)-n-pyrazin-2-ylpropanamide Chemical compound CON=C1CCCC1CC(C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)C(=O)NC1=CN=CC=N1 ZTUPVKQZCNWTPJ-UHFFFAOYSA-N 0.000 claims description 4
ALQVHXBODSBABM-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-(3-hydroxy-3-methylcyclopentyl)-n-pyrazin-2-ylpropanamide Chemical compound C1C(C)(O)CCC1CC(C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)C(=O)NC1=CN=CC=N1 ALQVHXBODSBABM-UHFFFAOYSA-N 0.000 claims description 4
GXHXMLBXMHAFPH-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-(3-hydroxyiminocyclopentyl)-n-pyrazin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC=NC=1)CC1CC(=NO)CC1 GXHXMLBXMHAFPH-UHFFFAOYSA-N 0.000 claims description 4
GLNVJMFXTONFIB-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-(oxan-4-yl)-n-pyrazin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC=NC=1)CC1CCOCC1 GLNVJMFXTONFIB-UHFFFAOYSA-N 0.000 claims description 4
FCJWBSWAOPKNOK-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-(oxolan-3-yl)-n-pyrazin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC=NC=1)CC1COCC1 FCJWBSWAOPKNOK-UHFFFAOYSA-N 0.000 claims description 4
XRUDMDCAYVNXAE-KWCCSABGSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-[(2r)-oxolan-2-yl]-n-pyrazin-2-ylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC=NC=1)C[C@@H]1OCCC1 XRUDMDCAYVNXAE-KWCCSABGSA-N 0.000 claims description 4
GESAFELMZAUSAB-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-(2-oxocyclopentyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC=CN=1)CC1C(=O)CCC1 GESAFELMZAUSAB-UHFFFAOYSA-N 0.000 claims description 4
DDRNUAUZJJYKJF-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-(3-oxocyclopentyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CC(=O)CC1 DDRNUAUZJJYKJF-UHFFFAOYSA-N 0.000 claims description 4
OMHLZWORUWLWQD-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-(oxan-2-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC=CN=1)CC1OCCCC1 OMHLZWORUWLWQD-UHFFFAOYSA-N 0.000 claims description 4
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CPRNKFSLTVOMHN-UHFFFAOYSA-N methyl 2-(3,4-dichlorophenyl)-3-(3-methoxycyclopentyl)propanoate Chemical compound C1C(OC)CCC1CC(C(=O)OC)C1=CC=C(Cl)C(Cl)=C1 CPRNKFSLTVOMHN-UHFFFAOYSA-N 0.000 description 2
FICRQLPWDXPNSU-UHFFFAOYSA-N methyl 2-(3,4-dichlorophenyl)-3-[2-(oxan-2-yloxy)cyclopentyl]propanoate Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(=O)OC)CC1CCCC1OC1CCCCO1 FICRQLPWDXPNSU-UHFFFAOYSA-N 0.000 description 2
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UDHPLJHDAWCRSV-UHFFFAOYSA-N methyl 2-(3-chloro-4-methylsulfanylphenyl)-3-(oxan-4-yl)propanoate Chemical compound C=1C=C(SC)C(Cl)=CC=1C(C(=O)OC)CC1CCOCC1 UDHPLJHDAWCRSV-UHFFFAOYSA-N 0.000 description 2
CPTNXNUUYOXVDK-UHFFFAOYSA-N methyl 2-(3-chloro-4-methylsulfonylphenyl)-3-(4-oxocyclohexyl)propanoate Chemical compound C=1C=C(S(C)(=O)=O)C(Cl)=CC=1C(C(=O)OC)CC1CCC(=O)CC1 CPTNXNUUYOXVDK-UHFFFAOYSA-N 0.000 description 2
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BXHYXEYCMKAKRO-UHFFFAOYSA-N methyl 2-(3,4-dichlorophenyl)-3-(2,2-difluorocyclopentyl)propanoate Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(=O)OC)CC1CCCC1(F)F BXHYXEYCMKAKRO-UHFFFAOYSA-N 0.000 description 1
XMIINSJCNWYVTF-UHFFFAOYSA-N methyl 2-(3,4-dichlorophenyl)-3-(3,3-difluorocyclopentyl)propanoate Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(=O)OC)CC1CCC(F)(F)C1 XMIINSJCNWYVTF-UHFFFAOYSA-N 0.000 description 1
KDIUGQMHEWBIRG-UHFFFAOYSA-N methyl 2-(3,4-dichlorophenyl)-3-(6,10-dioxaspiro[4.5]decan-3-yl)propanoate Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(=O)OC)CC(C1)CCC21OCCCO2 KDIUGQMHEWBIRG-UHFFFAOYSA-N 0.000 description 1
HNTCDDPBCMOXPT-UHFFFAOYSA-N methyl 2-(3,4-dichlorophenyl)-3-(oxolan-2-yl)propanoate Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(=O)OC)CC1CCCO1 HNTCDDPBCMOXPT-UHFFFAOYSA-N 0.000 description 1
AGXGHYRXIFQONI-UHFFFAOYSA-N methyl 2-(3-chloro-4-methylsulfanylphenyl)-3-(1,4-dioxaspiro[4.5]decan-8-yl)propanoate Chemical compound C=1C=C(SC)C(Cl)=CC=1C(C(=O)OC)CC(CC1)CCC21OCCO2 AGXGHYRXIFQONI-UHFFFAOYSA-N 0.000 description 1
KSATUISADIBNFM-UHFFFAOYSA-N methyl 2-(3-chloro-4-methylsulfanylphenyl)-3-(6,10-dioxaspiro[4.5]decan-3-yl)propanoate Chemical compound C=1C=C(SC)C(Cl)=CC=1C(C(=O)OC)CC(C1)CCC21OCCCO2 KSATUISADIBNFM-UHFFFAOYSA-N 0.000 description 1
RVFFKCRQNNHDNG-JHJMLUEUSA-N methyl 2-(3-chloro-4-methylsulfanylphenyl)-3-[(2r)-oxolan-2-yl]propanoate Chemical compound C=1C=C(SC)C(Cl)=CC=1C(C(=O)OC)C[C@H]1CCCO1 RVFFKCRQNNHDNG-JHJMLUEUSA-N 0.000 description 1
NXYIHCSNZVWOQZ-UHFFFAOYSA-N methyl 2-(3-chloro-4-methylsulfonylphenyl)-3-(1,4-dioxaspiro[4.5]decan-8-yl)propanoate Chemical compound C=1C=C(S(C)(=O)=O)C(Cl)=CC=1C(C(=O)OC)CC(CC1)CCC21OCCO2 NXYIHCSNZVWOQZ-UHFFFAOYSA-N 0.000 description 1
LGWIDNCCGFCSBG-UHFFFAOYSA-N methyl 2-(3-chloro-4-methylsulfonylphenyl)-3-(3-oxocyclopentyl)propanoate Chemical compound C=1C=C(S(C)(=O)=O)C(Cl)=CC=1C(C(=O)OC)CC1CCC(=O)C1 LGWIDNCCGFCSBG-UHFFFAOYSA-N 0.000 description 1
BNELUTDOXMJGOE-UHFFFAOYSA-N methyl 2-(3-chloro-4-methylsulfonylphenyl)-3-(6,10-dioxaspiro[4.5]decan-3-yl)propanoate Chemical compound C=1C=C(S(C)(=O)=O)C(Cl)=CC=1C(C(=O)OC)CC(C1)CCC21OCCCO2 BNELUTDOXMJGOE-UHFFFAOYSA-N 0.000 description 1
FWGGQVSQRWLTLJ-JTDNENJMSA-N methyl 2-(3-chloro-4-methylsulfonylphenyl)-3-[(3r)-thian-3-yl]propanoate Chemical compound C=1C=C(S(C)(=O)=O)C(Cl)=CC=1C(C(=O)OC)C[C@H]1CCCSC1 FWGGQVSQRWLTLJ-JTDNENJMSA-N 0.000 description 1
FPAXVLRYGWWBRP-UHFFFAOYSA-N methyl 2-(4-methylsulfonylphenyl)-3-[2-(oxan-2-yloxy)cyclopentyl]propanoate Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(C(=O)OC)CC1CCCC1OC1CCCCO1 FPAXVLRYGWWBRP-UHFFFAOYSA-N 0.000 description 1
NOLYSGAWDCBXRV-UHFFFAOYSA-N methyl 2-(4-methylsulfonylphenyl)-3-[3-(oxan-2-yloxy)cyclopentyl]propanoate Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(C(=O)OC)CC(C1)CCC1OC1CCCCO1 NOLYSGAWDCBXRV-UHFFFAOYSA-N 0.000 description 1
XOLJZOGZMYWBHV-NFJWQWPMSA-N methyl 2-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[(2r)-oxolan-2-yl]propanoate Chemical compound C=1C=C(F)C(C(F)(F)F)=CC=1C(C(=O)OC)C[C@H]1CCCO1 XOLJZOGZMYWBHV-NFJWQWPMSA-N 0.000 description 1
ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 1
MYWWWNVEZBAKHR-UHFFFAOYSA-N methyl 3-(3-methoxy-3-oxopropyl)sulfanylpropanoate Chemical compound COC(=O)CCSCCC(=O)OC MYWWWNVEZBAKHR-UHFFFAOYSA-N 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
UCWQHVABVFGEJB-UHFFFAOYSA-N n-pyrazin-2-ylpropanamide Chemical compound CCC(=O)NC1=CN=CC=N1 UCWQHVABVFGEJB-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000008012 organic excipient Substances 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
ROTONRWJLXYJBD-UHFFFAOYSA-N oxan-2-ylmethanol Chemical compound OCC1CCCCO1 ROTONRWJLXYJBD-UHFFFAOYSA-N 0.000 description 1
URUUZIAJVSGYRC-UHFFFAOYSA-N oxan-3-one Chemical compound O=C1CCCOC1 URUUZIAJVSGYRC-UHFFFAOYSA-N 0.000 description 1
DCBKCZSYJRZBDB-UHFFFAOYSA-N oxan-4-ylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1CCOCC1 DCBKCZSYJRZBDB-UHFFFAOYSA-N 0.000 description 1
PCPUMGYALMOCHF-UHFFFAOYSA-N oxolan-3-ylmethanol Chemical compound OCC1CCOC1 PCPUMGYALMOCHF-UHFFFAOYSA-N 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
210000004738 parenchymal cell Anatomy 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
238000005897 peptide coupling reaction Methods 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
125000005561 phenanthryl group Chemical group 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
230000000291 postprandial effect Effects 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
239000001294 propane Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
230000006340 racemization Effects 0.000 description 1
230000029964 regulation of glucose metabolic process Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000012552 review Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
229910001958 silver carbonate Inorganic materials 0.000 description 1
229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
150000003527 tetrahydropyrans Chemical class 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
DSXFPRKPFJRPIB-UHFFFAOYSA-N thiolan-3-one Chemical compound O=C1CCSC1 DSXFPRKPFJRPIB-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 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
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
230000009261 transgenic effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000000080 wetting agent Substances 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/20—Nitrogen atoms
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Obesity (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Thiazole And Isothizaole Compounds (AREA)
Furan Compounds (AREA)
Pyrane Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

HR20040953A 2002-04-26 2004-10-12 Substituted phenylacetamides and their use as glucokinase activators HRP20040953A2 (en)

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Application Number	Priority Date	Filing Date	Title
US37616102P	2002-04-26	2002-04-26
PCT/EP2003/003844 WO2003095438A1 (en)	2002-04-26	2003-04-14	Substituted phenylacetamides and their use as glucokinase activators

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JP (1)	JP4091600B2 (ru)
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UA (1)	UA80427C2 (ru)
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US20030225283A1 (en)	2003-12-04
IL164780A (en)	2009-05-04
CA2482346C (en)	2010-03-09
JP4091600B2 (ja)	2008-05-28
CA2482346A1 (en)	2003-11-20
IL164780A0 (en)	2005-12-18
ATE346056T1 (de)	2006-12-15
NZ535706A (en)	2007-08-31
US7259166B2 (en)	2007-08-21
KR20040104633A (ko)	2004-12-10
DK1501815T3 (da)	2007-04-02
ES2276097T3 (es)	2007-06-16
TWI281917B (en)	2007-06-01
TW200402418A (en)	2004-02-16
EP1501815A1 (en)	2005-02-02
MY135222A (en)	2008-02-29
AU2003232204B8 (en)	2009-07-30
EA200401398A1 (ru)	2005-06-30
CN1649859A (zh)	2005-08-03
RS93604A (en)	2007-02-05
DE60309856D1 (de)	2007-01-04
PL373701A1 (en)	2005-09-05
US7105671B2 (en)	2006-09-12
DE60309856T2 (de)	2007-06-14
US20060178429A1 (en)	2006-08-10
JP2005535589A (ja)	2005-11-24
ZA200407986B (en)	2005-10-18
AU2003232204B2 (en)	2006-09-14
BR0309546A (pt)	2005-02-15
HK1078088A1 (en)	2006-03-03
AR039665A1 (es)	2005-03-02
AU2003232204A1 (en)	2003-11-11
UA80427C2 (en)	2007-09-25
NO20044534L (no)	2004-12-22
ECSP045382A (es)	2005-01-03
EA011297B1 (ru)	2009-02-27
UY27787A1 (es)	2003-10-31
EP1501815B1 (en)	2006-11-22
MA27113A1 (fr)	2004-12-20
WO2003095438A1 (en)	2003-11-20
WO2003095438A9 (en)	2004-12-23
PE20040451A1 (es)	2004-07-21
CN1329386C (zh)	2007-08-01
PA8572301A1 (es)	2004-05-26
KR100669587B1 (ko)	2007-01-15
GT200300096A (es)	2004-01-15
MXPA04010605A (es)	2004-12-13
PT1501815E (pt)	2007-01-31
TNSN04211A1 (fr)	2007-03-12

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Publication	Publication Date	Title
HRP20040953A2 (en)	2005-06-30	Substituted phenylacetamides and their use as glucokinase activators
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EP1305301B1 (en)	2005-06-15	Alpha-acyl and alpha-heteroatom-substituted benzene acetamide glucokinase activators
EP1282611B1 (en)	2004-10-20	Substituted phenylacetamides and their use as glucokinase activators
DE60014610T2 (de)	2006-03-09	Glukokinase aktivatoren
AU2001287600A1 (en)	2002-05-02	Alpha-acyl and Alpha-heteroatom-substituted Benzene Acetamide Glucokinase Activators
AU2003292229A1 (en)	2004-06-30	5-substituted-pyrazine or pyridine glucokinase activators