KR20010041814A - 단백질 티로신 포스파타제（ｐｔｐａｓｅｓ）의 조절제 - Google Patents

Info

Publication number

KR20010041814A

KR20010041814A KR1020007010093A KR20007010093A KR20010041814A KR 20010041814 A KR20010041814 A KR 20010041814A KR 1020007010093 A KR1020007010093 A KR 1020007010093A KR 20007010093 A KR20007010093 A KR 20007010093A KR 20010041814 A KR20010041814 A KR 20010041814A

Authority

KR

South Korea

Prior art keywords

amino

dihydro

thieno

oxalyl

carboxylic acid

Prior art date

1998-03-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

Links

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• 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 title claims abstract description 95
• 108020000494 protein-tyrosine phosphatase Proteins 0.000 title claims abstract description 95
• -1 PTPα Proteins 0.000 claims abstract description 429
• 150000001875 compounds Chemical class 0.000 claims abstract description 202
• 239000000203 mixture Substances 0.000 claims abstract description 108
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 57
• 230000000694 effects Effects 0.000 claims abstract description 47
• 201000010099 disease Diseases 0.000 claims abstract description 45
• 238000000034 method Methods 0.000 claims abstract description 35
• 230000001965 increasing effect Effects 0.000 claims abstract description 34
• 239000000122 growth hormone Substances 0.000 claims abstract description 32
• 102000018997 Growth Hormone Human genes 0.000 claims abstract description 30
• 108010051696 Growth Hormone Proteins 0.000 claims abstract description 30
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 27
• 238000003786 synthesis reaction Methods 0.000 claims abstract description 25
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 23
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• 230000002829 reductive effect Effects 0.000 claims abstract description 20
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 20
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• 238000011282 treatment Methods 0.000 claims abstract description 18
• 230000004044 response Effects 0.000 claims abstract description 14
• 208000001132 Osteoporosis Diseases 0.000 claims abstract description 13
• 229940088597 hormone Drugs 0.000 claims abstract description 13
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• 208000035473 Communicable disease Diseases 0.000 claims abstract description 11
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• 208000002705 Glucose Intolerance Diseases 0.000 claims abstract description 10
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 10
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• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims abstract description 10
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• 125000003118 aryl group Chemical group 0.000 claims description 111
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• 229910052739 hydrogen Inorganic materials 0.000 claims description 74
• 239000001257 hydrogen Substances 0.000 claims description 74
• 125000000217 alkyl group Chemical group 0.000 claims description 69
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
• 150000002431 hydrogen Chemical class 0.000 claims description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims description 34
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 239000002253 acid Substances 0.000 claims description 28
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
• 229920006395 saturated elastomer Polymers 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 21
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 20
• 230000003287 optical effect Effects 0.000 claims description 20
• 125000004122 cyclic group Chemical group 0.000 claims description 19
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
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• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 239000001301 oxygen Chemical group 0.000 claims description 12
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• 102000004169 proteins and genes Human genes 0.000 claims description 12
• 229910052717 sulfur Chemical group 0.000 claims description 12
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• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 11
• 125000004104 aryloxy group Chemical group 0.000 claims description 11
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• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• LZNNMMKMGKFYLL-UHFFFAOYSA-N 2h-pyran-3-carboxylic acid Chemical compound OC(=O)C1=CC=COC1 LZNNMMKMGKFYLL-UHFFFAOYSA-N 0.000 claims description 9
• 125000004043 oxo group Chemical group O=* 0.000 claims description 9
• DCWXELXMIBXGTH-QMMMGPOBSA-N phosphonotyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-QMMMGPOBSA-N 0.000 claims description 9
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• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
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• 125000005110 aryl thio group Chemical group 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• DWLHTIPCWYOEMT-UHFFFAOYSA-N 2h-thiopyran-3-carboxylic acid Chemical compound OC(=O)C1=CC=CSC1 DWLHTIPCWYOEMT-UHFFFAOYSA-N 0.000 claims description 6
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 239000000463 material Substances 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 6
• 150000001299 aldehydes Chemical class 0.000 claims description 5
• 125000005157 alkyl carboxy group Chemical group 0.000 claims description 5
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000002552 dosage form Substances 0.000 claims description 5
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• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
• 150000003951 lactams Chemical class 0.000 claims description 5
• DEBZQUFVQZPPLC-UHFFFAOYSA-N 2h-chromene-3-carboxylic acid Chemical compound C1=CC=C2OCC(C(=O)O)=CC2=C1 DEBZQUFVQZPPLC-UHFFFAOYSA-N 0.000 claims description 4
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 150000003949 imides Chemical class 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• ISZAWTJNJSOJQB-UHFFFAOYSA-N 2-(oxaloamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound C1CCCC2=C1SC(NC(=O)C(=O)O)=C2C(O)=O ISZAWTJNJSOJQB-UHFFFAOYSA-N 0.000 claims description 3
• ZIMJSFGMHLCHIV-UHFFFAOYSA-N 2-(oxaloamino)-6-(2-phenylethyl)-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxylic acid Chemical compound C1CC=2C(C(O)=O)=C(NC(=O)C(=O)O)SC=2CN1CCC1=CC=CC=C1 ZIMJSFGMHLCHIV-UHFFFAOYSA-N 0.000 claims description 3
• RYJQIVLCRVQLAY-UHFFFAOYSA-N 2-(oxaloamino)-6-(pyridin-2-ylmethyl)-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxylic acid Chemical compound C1CC=2C(C(O)=O)=C(NC(=O)C(=O)O)SC=2CN1CC1=CC=CC=N1 RYJQIVLCRVQLAY-UHFFFAOYSA-N 0.000 claims description 3
• CPBBXECXUZCULL-UHFFFAOYSA-N 2-(oxaloamino)-6-(pyridin-3-ylmethyl)-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxylic acid Chemical compound C1CC=2C(C(O)=O)=C(NC(=O)C(=O)O)SC=2CN1CC1=CC=CN=C1 CPBBXECXUZCULL-UHFFFAOYSA-N 0.000 claims description 3
• XUGANLGVQLASCQ-UHFFFAOYSA-N 2-(oxaloamino)-6-(pyridin-4-ylmethyl)-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxylic acid Chemical compound C1CC=2C(C(O)=O)=C(NC(=O)C(=O)O)SC=2CN1CC1=CC=NC=C1 XUGANLGVQLASCQ-UHFFFAOYSA-N 0.000 claims description 3
• FSCFWZSWPCIYDY-UHFFFAOYSA-N 2-(oxaloamino)-6-oxo-5,7-dihydro-4h-1-benzothiophene-3-carboxylic acid Chemical compound C1C(=O)CCC2=C1SC(NC(=O)C(=O)O)=C2C(O)=O FSCFWZSWPCIYDY-UHFFFAOYSA-N 0.000 claims description 3
• ZIBMATWHOAGNTR-UHFFFAOYSA-N 2-(oxalyl-amino)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid Chemical compound C1NCCC2=C1SC(NC(=O)C(=O)O)=C2C(O)=O ZIBMATWHOAGNTR-UHFFFAOYSA-N 0.000 claims description 3
• SNNOZMNTPOIDSI-UHFFFAOYSA-N 2-(oxalyl-amino)-4,7-dihydro-5h-thieno[2,3-c]pyran-3-carboxylic acid Chemical compound C1OCCC2=C1SC(NC(=O)C(=O)O)=C2C(O)=O SNNOZMNTPOIDSI-UHFFFAOYSA-N 0.000 claims description 3
• ZPDVRWNOCOREGF-UHFFFAOYSA-N 2-(oxalyl-amino)-4,7-dihydro-5h-thieno[2,3-c]thiopyran-3-carboxylic acid Chemical compound C1SCCC2=C1SC(NC(=O)C(=O)O)=C2C(O)=O ZPDVRWNOCOREGF-UHFFFAOYSA-N 0.000 claims description 3
• NIIJYLAODPZYTB-UHFFFAOYSA-N 2-[[6-hydroxy-3-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]amino]-2-oxoacetic acid Chemical compound C1C(O)CCC2=C1SC(NC(=O)C(O)=O)=C2CO NIIJYLAODPZYTB-UHFFFAOYSA-N 0.000 claims description 3
• NKHDPHJFMYZNMI-UHFFFAOYSA-N 6-(oxaloamino)-1h-indole-7-carboxylic acid Chemical compound OC(=O)C(=O)NC1=CC=C2C=CNC2=C1C(O)=O NKHDPHJFMYZNMI-UHFFFAOYSA-N 0.000 claims description 3
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• CEOJCMQCQZMARJ-UHFFFAOYSA-N 6-[(3-methoxyphenyl)methyl]-2-(oxaloamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxylic acid Chemical compound COC1=CC=CC(CN2CC3=C(C(=C(NC(=O)C(O)=O)S3)C(O)=O)CC2)=C1 CEOJCMQCQZMARJ-UHFFFAOYSA-N 0.000 claims description 3
• DNUOCYUTEIKZFI-UHFFFAOYSA-N 6-benzyl-2-(oxaloamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxylic acid Chemical compound C1CC=2C(C(O)=O)=C(NC(=O)C(=O)O)SC=2CN1CC1=CC=CC=C1 DNUOCYUTEIKZFI-UHFFFAOYSA-N 0.000 claims description 3
• WCLCDQBGCADVSY-UHFFFAOYSA-N 6-ethoxycarbonylpyridine-3-carboxylic acid Chemical compound CCOC(=O)C1=CC=C(C(O)=O)C=N1 WCLCDQBGCADVSY-UHFFFAOYSA-N 0.000 claims description 3
• CLPLHASNHDFGBI-UHFFFAOYSA-N 6-methyl-2-(oxaloamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxylic acid Chemical compound C1N(C)CCC2=C1SC(NC(=O)C(O)=O)=C2C(O)=O CLPLHASNHDFGBI-UHFFFAOYSA-N 0.000 claims description 3
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