CN101374835A - 作为PTPase抑制剂的取代的咪唑衍生物、组合物和使用方法 - Google Patents
作为PTPase抑制剂的取代的咪唑衍生物、组合物和使用方法 Download PDFInfo
- Publication number
- CN101374835A CN101374835A CNA2007800039423A CN200780003942A CN101374835A CN 101374835 A CN101374835 A CN 101374835A CN A2007800039423 A CNA2007800039423 A CN A2007800039423A CN 200780003942 A CN200780003942 A CN 200780003942A CN 101374835 A CN101374835 A CN 101374835A
- Authority
- CN
- China
- Prior art keywords
- phenyl
- alkyl
- compound
- imidazoles
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 title claims abstract description 42
- 108020000494 protein-tyrosine phosphatase Proteins 0.000 title claims abstract description 42
- 239000000203 mixture Chemical class 0.000 title claims description 96
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- 150000002460 imidazoles Chemical class 0.000 title abstract description 22
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 228
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- 125000000068 chlorophenyl group Chemical group 0.000 claims description 300
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 102
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- 125000003118 aryl group Chemical group 0.000 claims description 48
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Classifications
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- 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
- C07D417/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
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Abstract
Description
实施例 | 名称 | LC/MS(m/z) |
15 | 5-{4-[2-(4′-环己基-联苯-4-基甲基)-4-(2,4-二氟-苯基)-咪唑-1-基]-2-甲基-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 653(M+H)+ |
16 | 5-{4-[4-(4-氯-苯基)-2-(4′-环己基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 637(M+H)+ |
17 | 5-{4-[4-(2-氯-苯基)-2-(4′-环己基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 637(M+H)+ |
18 | 5-{4-[2-(4′-环己基-联苯-4-基甲基)-4-(2,6-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 671(M+H)+ |
19 | 5-{4-[2-(4′-环己基-联苯-4-基甲基)-4-(2,4,6-三氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 705(M+H)+ |
20 | 5-{4-[4-(2-氯-4-氟-苯基)-2-(4′-环己基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 655(M+H)+ |
实施例 | 名称 | LC/MS(m/z) |
26 | 5-{3-[4-(2,4-二氯-苯基)-2-(3′-甲磺酰基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 667(M+H)+ |
27 | 5-{3-[2-(3′-环己烷磺酰基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 735(M+H)+ |
28 | 5-{3-[2-(4′-环己烷磺酰基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 735(M+H)+ |
29 | 5-{3-[4-(2,4-二氯-苯基)-2-(3′-丙氧基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 647(M+H)+ |
30 | 5-{3-[2-(3′-丁氧基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 661(M+H)+ |
31 | 5-(3-{4-(2,4-二氯-苯基)-2-[3′-(4,4,4-三氟-丁氧基)-联苯-4-基甲基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 715(M+H)+ |
32 | 5-{3-[4-(2,4-二氯-苯基)-2-(3′-乙氧基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 633(M+H)+ |
33 | 5-{3-[2-(3′-环己基甲氧基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 701(M+H)+ |
34 | 5-(3-{4-(2,4-二氯-苯基)-2-[3′-(3-甲基-丁氧基)-联苯-4-基甲基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 675(M+H)+ |
35 | 5-{3-[2-(3′-环戊基甲氧基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 687(M+H)+ |
36 | 5-{3-[2-(3′-环己氧基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 687(M+H)+ |
37 | 5-(3-{4-(2,4-二氯-苯基)-2-[3′-(2,2-二甲基-丙氧基)-联苯-4-基甲基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 675(M+H)+ |
38 | 5-{3-[2-(3′-叔-丁氧基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 661(M+H)+ |
39 | 5-{3-[2-[3′-(2-环己基-乙氧基)-联苯-4-基甲基]-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 715(M+H)+ |
40 | 5-{3-[2-[3′-(2-环戊基-乙氧基)-联苯-4-基甲基]-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 701(M+H)+ |
41 | 5-{3-[4-(2,4-二氯-苯基)-2-(3′-苯乙氧基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 709(M+H)+ |
42 | 5-(3-{4-(2,4-二氯-苯基)-2-[3′-(4,4-二甲基-戊基)-联苯-4-基甲基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 687(M+H)+ |
43 | 5-{3-[2-[3′-(2-环己基-乙基)-联苯-4-基甲基]-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 699(M+H)+ |
44 | 5-(3-{4-(2,4-二氯-苯基)-2-[3′-(3,3-二甲基-丁基硫烷基)-联苯-4-基甲基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 705(M+H)+ |
实施例 | 名称 | LC/MS(m/z) |
58 | 5-{5-[2-(4′-环己基-联苯-4-基甲基)-4-(2,4-二氟-苯基)-咪唑-1-基]-2-甲基-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 653(M+H)+ |
59 | 5-{5-[2-(4′-环己基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-2-甲基-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 685(M+H)+ |
60 | 5-{5-[2-(4′-环己基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-2-甲氧基-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 701(M+H)+ |
61 | 5-{3-[2-(4′-环己基-联苯-4-基甲基)-4-(2,6-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 671(M+H)+ |
62 | 5-{3-[2-(4′-环己基-联苯-4-基甲基)-4-(2,4,6-三氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 705(M+H)+ |
63 | 5-(3-{4-(2,6-二氯-苯基)-2-[3′-(3,3-二甲基-丁氧基)-联苯-4-基甲基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 689(M+H)+ |
64 | 5-{3-[2-(3′-环己基甲氧基-联苯-4-基甲基)-4-(2,6-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 701(M+H)+ |
65 | 5-(3-{4-(2,4-二氟-苯基)-2-[3′-(3,3-二甲基-丁氧基)-联苯-4-基甲基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 657(M+H)+ |
实施例 | 名称 | LC/MS(m/z) |
78 | 5-{4-[2-(4′-叔丁基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-4-乙基-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 673(M+H)+ |
79 | 5-{4-[2-(4′-叔丁基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-4,4-二甲基-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 673(M+H)+ |
80 | 1-{4-[2-(4′-叔丁基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-2,2-二氧代-硫杂-1,3-二氮杂-螺[4.5]癸-4-酮 | 713(M+H)+ |
实施例 | 名称 | LC/MS(m/z) |
86 | 5-(3-{4-(2,4-二氯-苯基)-2-{4′-[(3R)-3-苯基-吡咯烷-1-基]-联苯-4-基甲基}-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 734(M+H)+ |
87 | 5-{3-[2-{4′-[(3S)-3-环己基-吡咯烷-1-基]-联苯-4-基甲基}-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 740(M+H)+ |
88 | 5-{3-[2-{4′-[(3R)-3-环己基-吡咯烷-1-基]-联苯-4-基甲基}-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 740(M+H)+ |
89 | 5-{3-[2-{3′-[(3S)-3-环己基-吡咯烷-1-基]-联苯-4-基甲基}-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 740(M+H)+ |
实施例 | 名称 | LC/MS(m/z) |
101 | 5-{4-[4-(2,4-二氯-苯基)-2-(4′-异丁基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 645(M+H)+ |
102 | 5-{4-[4-(2,4-二氯-苯基)-2-(4′-吗啉-4-基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 674(M+H)+ |
103 | 5-{4-[2-(4′-丁基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 645(M+H)+ |
104 | 5-{4-[4-(2,4-二氯-苯基)-2-(4′-哌啶-1-基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 672(M+H)+ |
105 | 5-{4-[4-(2,4-二氯-苯基)-2-(4′-异丙基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 631(M+H)+ |
106 | 5-{4-[2-(3′-硝基-4′-异丁基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 690(M+H)+ |
实施例 | 名称 | LC/MS(m/z) |
121 | 5-{3-[4-(2,4-二氯-苯基)-2-(4′-哌啶-1-基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 672(M+H)+ |
122 | 5-{3-[2-(3′-硝基-4′-异丁基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 690(M+H)+ |
实施例 | 名称 | LC/MS(m/z) |
125 | 5-{3-[4-(2,4-二氯-苯基)-2-(2′-氟-5′-丙氧基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 665(M+H)+ |
126 | 5-{3-[2-(2′-丁氧基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 661(M+H)+ |
127 | 5-(3-{4-(2,4-二氯-苯基)-2-[4′-(3,3-二甲基-丁氧基)-联苯-4-基甲基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 689(M+H)+ |
128 | 5-{3-[4-(2,4-二氯-苯基)-2-(4′-异丁氧基-联苯-4-基甲基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 689(M+H)+ |
129 | 5-{3-[2-(4′-环己基甲氧基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 701(M+H)+ |
130 | 5-(3-{4-(2,4-二氯-苯基)-2-[4′-(3,3-二甲基-丁基硫烷基)-联苯-4-基甲基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 705(M+H)+ |
实施例 | 名称 | LC/MS(m/z) |
146 | 5-{3-氯-4-[2-(4′-环己基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 705(M+H)+ |
147 | 5-{4-[2-(4′-环己基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-3-三氟甲基-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 739(M+H)+ |
148 | 5-{4-[2-(4′-环己基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-3-氟-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 689(M+H)+ |
实施例 | 名称 | LC/MS(m/z) |
156 | 5-{3-[2-[4′-(2-环己基-乙基)-联苯-4-基甲基]-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 699(M+H)+ |
157 | 5-(3-{4-(2,4-二氯-苯基)-2-[4′-(3,3-二甲基-丁基)-联苯-4-基甲基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 673(M+H)+ |
158 | 5-{3-[2-(4′-环己基甲基-联苯-4-基甲基)-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 685(M+H)+ |
159 | 5-(3-{4-(2,4-二氯-苯基)-2-[4′-(4-甲基-戊基)-联苯-4-基甲基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 673(M+H)+ |
实施例 | 名称 | LC/MS(m/z) |
168 | 5-{3-[4-(2,4-二氯-苯基)-2-(4-己-1-烯基-苄基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 595(M+H)+ |
169 | 5-(3-{4-(2,4-二氯-苯基)-2-[4-(3,3-二甲基-丁-1-烯基)-苄基]-咪唑-1-基}-苯基)-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 595(M+H)+ |
170 | 5-{3-[2-[4-(2-环己基-乙烯基)-苄基]-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 595(M+H)+ |
171 | 5-{4-[2-[3′-(2-环己基-乙氧基)-联苯-4-基甲基]-4-(2,4-二氯-苯基)-咪唑-1-基]-苯基}-1,2,5-噻二唑烷-3-酮-1,1-二氧化物 | 715(M+H)+ |
Claims (59)
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US76325606P | 2006-01-30 | 2006-01-30 | |
US60/763,256 | 2006-01-30 | ||
PCT/US2007/002675 WO2007089857A2 (en) | 2006-01-30 | 2007-01-30 | Substituted imidazole derivatives and their use as ptpase inhibitors |
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US (3) | US7723369B2 (zh) |
EP (1) | EP1991544B1 (zh) |
JP (1) | JP5180099B2 (zh) |
KR (1) | KR20080094806A (zh) |
CN (1) | CN101374835B (zh) |
AU (1) | AU2007211319B9 (zh) |
BR (1) | BRPI0707338A2 (zh) |
CA (1) | CA2637024C (zh) |
EA (1) | EA019385B1 (zh) |
HK (1) | HK1127342A1 (zh) |
IL (1) | IL192557A (zh) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114761413A (zh) * | 2019-11-08 | 2022-07-15 | 明知大学校产学协力团 | 碳青霉烯水解D类β-内酰胺酶抑制剂及其制备方法 |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ548208A (en) * | 2004-02-12 | 2010-09-30 | Transtech Pharma Inc | Substituted azole derivatives, compositions, and methods of use |
CN101374835B (zh) * | 2006-01-30 | 2012-04-25 | 转化技术制药公司 | 作为PTPase抑制剂的取代的咪唑衍生物、组合物和使用方法 |
CA2764387A1 (en) | 2009-06-05 | 2010-12-09 | Link Medicine Corporation | Aminopyrrolidinone derivatives and uses thereof |
JPWO2011007819A1 (ja) | 2009-07-17 | 2012-12-27 | 塩野義製薬株式会社 | ラクタムまたはベンゼンスルホンアミド化合物を含有する医薬 |
JP5398076B2 (ja) * | 2009-12-10 | 2014-01-29 | 四国化成工業株式会社 | 2−(ブロモベンジル)−4−(ブロモフェニル)−5−メチルイミダゾール化合物 |
JP5398075B2 (ja) * | 2010-01-13 | 2014-01-29 | 四国化成工業株式会社 | 4−(ジクロロフェニル)−2−(4−フルオロベンジル)−5−メチルイミダゾール化合物 |
KR101898610B1 (ko) | 2010-08-31 | 2018-09-14 | 서울대학교산학협력단 | PPARδ 활성물질의 태자 재프로그래밍 용도 |
US9040525B2 (en) | 2010-10-08 | 2015-05-26 | Mochida Pharmaceutical Co., Ltd. | Cyclic amide derivative |
WO2012094580A2 (en) | 2011-01-07 | 2012-07-12 | High Point Pharmaceuticals, Llc | Compounds that modulate oxidative stress |
CA2834465A1 (en) | 2011-04-28 | 2012-11-01 | Mochida Pharmaceutical Co., Ltd. | Cyclic amide derivative |
WO2017053706A1 (en) * | 2015-09-23 | 2017-03-30 | The General Hospital Corporation | Tead transcription factor autopalmitoylation inhibitors |
DK3359528T3 (en) | 2015-10-07 | 2022-03-07 | Mitobridge Inc | Ppar agonists, compounds, pharmaceutical compositions, and methods of use thereof |
KR102430906B1 (ko) | 2016-04-13 | 2022-08-10 | 미토브리지, 인크. | Ppar 효능제, 화합물, 제약 조성물, 및 그의 사용 방법 |
EP4108659A1 (en) | 2016-06-07 | 2022-12-28 | Jacobio Pharmaceuticals Co., Ltd. | Novel heterocyclic derivatives useful as shp2 inhibitors |
AU2018239542C1 (en) | 2017-03-23 | 2021-02-11 | Jacobio Pharmaceuticals Co., Ltd. | Novel heterocyclic derivatives useful as SHP2 inhibitors |
WO2022035805A1 (en) * | 2020-08-10 | 2022-02-17 | Dana-Farber Cancer Institute, Inc. | Substituted 1,2,4-oxadiazoles as small molecule inhibitors of ubiquitin-specific protease 28 |
Family Cites Families (95)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63276054A (ja) | 1987-05-07 | 1988-11-14 | Hitachi Chem Co Ltd | 電子写真感光体 |
DE69026851T2 (de) | 1989-02-14 | 1996-10-31 | Wako Pure Chem Ind Ltd | Verfahren zur Erhöhung von Chemilumineszenz |
DE69311145T2 (de) | 1992-01-23 | 1998-02-05 | Inst Francais Du Petrole | Katalysator für die Alkylierung von Olefinen |
WO1993018029A1 (en) | 1992-03-13 | 1993-09-16 | Merck Sharp & Dohme Limited | Imidazole, triazole and tetrazole derivatives |
US5348969A (en) | 1992-04-03 | 1994-09-20 | Bristol-Myers Squibb Company | Diphenyloxazolyl-oxazoles as platelet aggregation inhibitors |
WO1994008982A1 (en) | 1992-10-13 | 1994-04-28 | Nippon Soda Co., Ltd. | Oxazole and thiazole derivatives |
ES2157991T3 (es) | 1993-09-14 | 2001-09-01 | Merck & Co Inc | Cadn que codifica una nueva proteina humana, la tirosin-fosfatasa. |
US5616601A (en) | 1994-07-28 | 1997-04-01 | Gd Searle & Co | 1,2-aryl and heteroaryl substituted imidazolyl compounds for the treatment of inflammation |
DE69635048T2 (de) | 1995-06-12 | 2006-02-16 | G.D. Searle & Co. | Mittel, enthaltend einen cyclooxygenase-2 inhibitor und einen 5-lipoxygenase inhibitor |
US5700816A (en) | 1995-06-12 | 1997-12-23 | Isakson; Peter C. | Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitor and a leukotriene A4 hydrolase inhibitor |
US6388076B1 (en) | 1995-06-19 | 2002-05-14 | Ontogen Corporation | Protein tyrosine phosphatase-inhibiting compounds |
US5753687A (en) | 1995-06-19 | 1998-05-19 | Ontogen Corporation | Modulators of proteins with phosphotryrosine recognition units |
JP3849157B2 (ja) | 1995-08-01 | 2006-11-22 | 東ソー株式会社 | 2−イミダゾリン類の製造法 |
US6238902B1 (en) | 1996-03-22 | 2001-05-29 | Genentech, Inc. | Protein tyrosine phosphatases |
US5958957A (en) | 1996-04-19 | 1999-09-28 | Novo Nordisk A/S | Modulators of molecules with phosphotyrosine recognition units |
AU740425B2 (en) * | 1996-12-16 | 2001-11-01 | Ontogen Corporation | Modulators of proteins with phosphotyrosine recognition units |
US5840721A (en) | 1997-07-09 | 1998-11-24 | Ontogen Corporation | Imidazole derivatives as MDR modulators |
GB9715816D0 (en) | 1997-07-25 | 1997-10-01 | Black James Foundation | Histamine H receptor ligands |
FR2767527B1 (fr) | 1997-08-25 | 1999-11-12 | Pf Medicament | Derives de piperazines indoliques, utiles comme medicaments et procede de preparation |
ATE268750T1 (de) | 1997-08-28 | 2004-06-15 | Biovitrum Ab | Proteintyrosinphosphatase inhibitoren |
AU9253798A (en) | 1997-09-23 | 1999-04-12 | Novo Nordisk A/S | Modules of protein tyrosine phosphatases (ptpases) |
US5972986A (en) | 1997-10-14 | 1999-10-26 | G.D. Searle & Co. | Method of using cyclooxygenase-2 inhibitors in the treatment and prevention of neoplasia |
US6159944A (en) * | 1998-02-27 | 2000-12-12 | Synchroneuron, Llc | Method for treating painful conditions of the anal region and compositions therefor |
US20020002199A1 (en) | 1998-03-12 | 2002-01-03 | Lone Jeppesen | Modulators of protein tyrosine phosphatases (ptpases) |
US6262044B1 (en) | 1998-03-12 | 2001-07-17 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPASES) |
US6699896B1 (en) | 1998-05-12 | 2004-03-02 | Wyeth | Oxazole-aryl-carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
AU4072799A (en) | 1998-05-12 | 1999-12-13 | American Home Products Corporation | 2,3,5-substituted biphenyls useful in the treatment of insulin resistance and hyperglycemia |
US20030194745A1 (en) | 1998-06-26 | 2003-10-16 | Mcdowell Robert S. | Cysteine mutants and methods for detecting ligand binding to biological molecules |
US6605753B1 (en) | 1998-07-24 | 2003-08-12 | Merck & Co., Inc. | Protein tyrosine phosphate-1B (PTP-1B) deficient mice and uses thereof |
US6174874B1 (en) | 1998-09-21 | 2001-01-16 | Merck Frosst Canada & Co. | Phosphonic acids derivatives as inhibitors of protein tyrosine phosphate 1B (PTP-1B) |
AU1543600A (en) | 1998-12-11 | 2000-07-03 | Mcgill University | Therapeutic and diagnostic uses of protein tyrosine phosphatase tc-ptp |
JP4221129B2 (ja) | 1999-02-15 | 2009-02-12 | 富士フイルム株式会社 | 含窒素ヘテロ環化合物、有機発光素子材料、有機発光素子 |
CA2372116A1 (en) | 1999-05-14 | 2000-11-23 | Claude Dufresne | Phosphonic and carboxylic acid derivatives as inhibitors of protein tyrosine phosphatase-1b (ptp-1b) |
DE60007697T2 (de) | 1999-07-21 | 2004-12-09 | F. Hoffmann-La Roche Ag | Triazolderivate |
CA2382789A1 (en) | 1999-08-27 | 2001-03-08 | Sugen, Inc. | Phosphate mimics and methods of treatment using phosphatase inhibitors |
US6410556B1 (en) | 1999-09-10 | 2002-06-25 | Novo Nordisk A/S | Modulators of protein tyrosine phosphateses (PTPases) |
EP1652839A3 (en) | 1999-10-28 | 2006-07-05 | Daiichi Pharmaceutical Co., Ltd. | Drug efflux pump inhibitor |
US6624182B1 (en) | 1999-11-25 | 2003-09-23 | Ciba Specialty Chemicals Corporation | Hydroxyphenylvinylthiazoles |
US6777433B2 (en) | 1999-12-22 | 2004-08-17 | Merck Frosst Canada & Co. | Protein tyrosine phosphatase 1B (PTP-1B) inhibitors containing two ortho-substituted aromatic phosphonates |
JP2003518129A (ja) | 1999-12-22 | 2003-06-03 | メルク フロスト カナダ アンド カンパニー | タンパク質チロシンホスファターゼ1b(ptp−1b)のインヒビターとなるホスホン酸誘導体 |
EP1244677A1 (en) | 1999-12-22 | 2002-10-02 | Merck Frosst Canada Inc. | Phosphonic acid biaryl derivatives as inhibitors of protein tyrosine phosphatase 1b (ptp-1b) |
WO2001046204A1 (en) | 1999-12-22 | 2001-06-28 | Merck Frosst Canada & Co. | Aromatic phosphonates as protein tyrosine phosphatase 1b (ptp-1b) inhibitors |
AU2336001A (en) | 1999-12-22 | 2001-07-03 | Merck Frosst Canada & Co. | Phosphonic acid derivatives as inhibitors of protein tyrosine phosphatase 1b (ptp-1b) |
WO2001053530A1 (en) | 2000-01-18 | 2001-07-26 | Human Genome Sciences, Inc. | Human protein tyrosine phosphatase polynucleotides, polypeptides, and antibodies |
TWI284639B (en) | 2000-01-24 | 2007-08-01 | Shionogi & Co | A compound having thrombopoietin receptor agonistic effect |
CA2435507A1 (en) | 2000-02-14 | 2001-08-23 | Ceptyr, Inc. | Improved assay for protein tyrosine phosphatases |
WO2001070754A1 (en) | 2000-03-22 | 2001-09-27 | Merck Frosst Canada & Co. | Sulfur substituted aryldifluoromethylphosphonic acids as ptp-1b inhibitors |
US6627647B1 (en) | 2000-03-23 | 2003-09-30 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 1-(4-aminophenyl)imidazoles and their use as anti-inflammatory agents |
EP1284260A4 (en) | 2000-05-22 | 2004-03-31 | Takeda Chemical Industries Ltd | TYROSINE PHOSPHATASE INHIBITORS |
DE60135752D1 (en) | 2000-07-06 | 2008-10-23 | Array Biopharma Inc | Tyrosinderivate als phosphatase inhibitoren |
US6613903B2 (en) | 2000-07-07 | 2003-09-02 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPases) |
US20020099073A1 (en) | 2000-07-07 | 2002-07-25 | Andersen Henrik Sune | Modulators of protein tyrosine phosphatases (PTPases) |
US20020035137A1 (en) | 2000-08-29 | 2002-03-21 | Gang Liu | Amino (oxo) acetic acid protein tyrosine phosphatase inhibitors |
US6972340B2 (en) | 2000-08-29 | 2005-12-06 | Abbott Laboratories | Selective protein tyrosine phosphatatase inhibitors |
US6472545B2 (en) | 2000-08-29 | 2002-10-29 | Abbott Laboratories | Protein tyrosine phosphatase inhibitors |
US20020169157A1 (en) | 2000-08-29 | 2002-11-14 | Gang Liu | Selective protein tyrosine phosphatatase inhibitors |
US6627767B2 (en) | 2000-08-29 | 2003-09-30 | Abbott Laboratories | Amino(oxo) acetic acid protein tyrosine phosphatase inhibitors |
GB0022079D0 (en) | 2000-09-08 | 2000-10-25 | Inst Of Molecul & Cell Biology | Novel protein tyrosine phosphatase inhibitor |
JP2002114768A (ja) | 2000-10-11 | 2002-04-16 | Japan Tobacco Inc | 2−(2,5−ジハロゲン−3,4−ジヒドロキシフェニル)アゾール化合物及びそれを含有してなる医薬組成物 |
US20030108883A1 (en) | 2001-02-13 | 2003-06-12 | Rondinone Cristina M. | Methods for identifying compounds that inhibit or reduce PTP1B expression |
US20030120073A1 (en) | 2001-04-25 | 2003-06-26 | Seto Christopher T. | Alpha-ketocarboxylic acid based inhibitors of phosphoryl tyrosine phosphatases |
JP2002322054A (ja) | 2001-04-26 | 2002-11-08 | Dai Ichi Seiyaku Co Ltd | 薬剤排出ポンプ阻害薬 |
WO2002102813A1 (en) | 2001-06-20 | 2002-12-27 | Merck Frosst Canada & Co. | Aryldifluoromethylphosphonic acids for treatment of diabetes |
US20030064979A1 (en) | 2001-06-29 | 2003-04-03 | Hansen Thomas Kruse | Method of inhibiting PTP 1B and /or T-cell PTP and/or other PTPases with an Asp residue at position 48 |
US20030170660A1 (en) | 2001-07-11 | 2003-09-11 | Sondergaard Helle Bach | P387L variant in protein tyrosine phosphatase-1B is associated with type 2 diabetes and impaired serine phosphorylation of PTP-1B in vitro |
CA2463441A1 (en) | 2001-10-12 | 2003-05-08 | Bayer Pharmaceuticals Corporation | Phenyl substituted 5-membered nitrogen containing heterocycles for the treatment of obesity |
ATE348828T1 (de) | 2001-10-19 | 2007-01-15 | Transtech Pharma Inc | Beta-carbolin-derivate als ptp-inhibitoren |
US7022730B2 (en) | 2001-10-19 | 2006-04-04 | Transtech Pharma, Inc. | Bis-heteroaryl alkanes as therapeutic agents |
CA2469228A1 (en) | 2001-12-03 | 2003-06-12 | Japan Tobacco Inc. | Azole compound and medicinal use thereof |
JP2003231679A (ja) | 2001-12-03 | 2003-08-19 | Japan Tobacco Inc | アゾール化合物及びその医薬用途 |
US6642381B2 (en) | 2001-12-27 | 2003-11-04 | Hoffman-La Roche Inc. | Pyrimido[5,4-e][1,2,4]triazine-5,7-diamine compounds as protein tyrosine phosphatase inhibitors |
US20030180827A1 (en) | 2002-01-04 | 2003-09-25 | Aventis Pharma Deutschland Gmbh. | Highly sensitive and continuous protein tyrosine phosphatase test using 6,8-difluoro-4-methylumbelliferyl phosphate |
US20030215899A1 (en) | 2002-02-13 | 2003-11-20 | Ceptyr, Inc. | Reversible oxidation of protein tyrosine phosphatases |
US6784205B2 (en) | 2002-03-01 | 2004-08-31 | Sunesis Pharmaceuticals, Inc. | Compounds that modulate the activity of PTP-1B and TC-PTP |
CN101597262A (zh) | 2002-03-05 | 2009-12-09 | 特兰斯泰克制药公司 | 抑制配体与高级糖化终产物受体相互作用的单和双环吡咯衍生物 |
CN1646508A (zh) | 2002-04-03 | 2005-07-27 | 诺瓦提斯公司 | 作为ptp酶1b抑制剂的5-取代的1,1-二氧代-1,2,5-噻二唑烷-3-酮衍生物 |
EP1494667A1 (en) | 2002-04-12 | 2005-01-12 | Pfizer Japan Inc. | Imidazole compounds as anti-inflammatory and analgesic agents |
JP2003313172A (ja) | 2002-04-23 | 2003-11-06 | Tosoh Corp | N−置換イミダゾール化合物の製造方法 |
JP4529342B2 (ja) | 2002-04-23 | 2010-08-25 | 東ソー株式会社 | 環状アミジニウム有機酸塩の製造方法 |
WO2003093498A1 (en) | 2002-04-29 | 2003-11-13 | The Ohio State University | Inhibition of protein tyrosine phosphatases and sh2 domains by a neutral phosphotyrosine mimetic |
US20040009946A1 (en) | 2002-05-23 | 2004-01-15 | Ceptyr, Inc. | Modulation of PTP1B expression and signal transduction by RNA interference |
US6849761B2 (en) | 2002-09-05 | 2005-02-01 | Wyeth | Substituted naphthoic acid derivatives useful in the treatment of insulin resistance and hyperglycemia |
EP1402888A1 (en) | 2002-09-18 | 2004-03-31 | Jerini AG | The use of substituted carbocyclic compounds as rotamases inhibitors |
WO2004062664A1 (en) | 2002-12-30 | 2004-07-29 | Vertex Pharmaceuticals Incorporated | Sulfhydantoins as phosphate isosteres for use as phosphatase inhibitors in the treatment of cancer and autoimmune disorders |
US7144911B2 (en) | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
US7279576B2 (en) | 2002-12-31 | 2007-10-09 | Deciphera Pharmaceuticals, Llc | Anti-cancer medicaments |
WO2004071448A2 (en) | 2003-02-12 | 2004-08-26 | Transtech Pharma Inc. | Substituted azole derivatives as inhibitors of protein tyrosine phosphatases |
CN1747936A (zh) | 2003-02-12 | 2006-03-15 | 特兰斯泰克制药公司 | 作为治疗试剂的取代吡咯衍生物 |
US20040167188A1 (en) | 2003-02-14 | 2004-08-26 | Zhili Xin | Protein-tyrosine phosphatase inhibitors and uses thereof |
MXPA05010945A (es) | 2003-04-09 | 2005-11-25 | Japan Tobacco Inc | Compuesto pentaciclico heteroaromatico y uso medicinal del mismo. |
WO2005035551A2 (en) * | 2003-10-08 | 2005-04-21 | Incyte Corporation | Inhibitors of proteins that bind phosphorylated molecules |
NZ548208A (en) * | 2004-02-12 | 2010-09-30 | Transtech Pharma Inc | Substituted azole derivatives, compositions, and methods of use |
US8119666B2 (en) * | 2005-12-08 | 2012-02-21 | Novartis Ag | 1,2,5-thiazolidine derivatives useful for treating conditions mediated by protein tyrosine phosphatases (PTPase) |
BRPI0619547A2 (pt) * | 2005-12-08 | 2011-10-04 | Novartis Ag | 1,1,3-trioxo-1,2,5-tiadiazolidinas, composição farmacêutica e uso das mesmas |
CN101374835B (zh) * | 2006-01-30 | 2012-04-25 | 转化技术制药公司 | 作为PTPase抑制剂的取代的咪唑衍生物、组合物和使用方法 |
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- 2007-01-30 AU AU2007211319A patent/AU2007211319B9/en not_active Ceased
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- 2007-01-30 JP JP2008553332A patent/JP5180099B2/ja not_active Expired - Fee Related
- 2007-01-30 KR KR1020087021180A patent/KR20080094806A/ko not_active Application Discontinuation
- 2007-01-30 ZA ZA200805648A patent/ZA200805648B/xx unknown
- 2007-01-30 BR BRPI0707338-0A patent/BRPI0707338A2/pt not_active IP Right Cessation
- 2007-01-30 WO PCT/US2007/002675 patent/WO2007089857A2/en active Application Filing
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- 2007-01-30 EP EP07763040.8A patent/EP1991544B1/en active Active
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2009
- 2009-06-03 HK HK09104978.9A patent/HK1127342A1/xx not_active IP Right Cessation
-
2010
- 2010-01-11 US US12/685,178 patent/US8404731B2/en not_active Expired - Fee Related
-
2012
- 2012-03-06 US US13/412,747 patent/US20120196906A1/en not_active Abandoned
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114761413A (zh) * | 2019-11-08 | 2022-07-15 | 明知大学校产学协力团 | 碳青霉烯水解D类β-内酰胺酶抑制剂及其制备方法 |
CN114761413B (zh) * | 2019-11-08 | 2024-04-12 | 明知大学校产学协力团 | 碳青霉烯水解D类β-内酰胺酶抑制剂及其制备方法 |
Also Published As
Publication number | Publication date |
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CN101374835B (zh) | 2012-04-25 |
KR20080094806A (ko) | 2008-10-24 |
US7723369B2 (en) | 2010-05-25 |
NZ569329A (en) | 2011-09-30 |
AU2007211319B2 (en) | 2012-01-19 |
IL192557A (en) | 2013-09-30 |
US20120196906A1 (en) | 2012-08-02 |
HK1127342A1 (en) | 2009-09-25 |
CA2637024C (en) | 2013-05-14 |
US20100113331A1 (en) | 2010-05-06 |
EA200870218A1 (ru) | 2009-02-27 |
JP2009525340A (ja) | 2009-07-09 |
EA019385B1 (ru) | 2014-03-31 |
AU2007211319A1 (en) | 2007-08-09 |
BRPI0707338A2 (pt) | 2011-05-03 |
US20070191385A1 (en) | 2007-08-16 |
WO2007089857A3 (en) | 2008-06-26 |
CA2637024A1 (en) | 2007-08-09 |
AU2007211319B9 (en) | 2012-05-31 |
US8404731B2 (en) | 2013-03-26 |
EP1991544B1 (en) | 2018-08-15 |
EP1991544A2 (en) | 2008-11-19 |
IL192557A0 (en) | 2009-02-11 |
WO2007089857A2 (en) | 2007-08-09 |
ZA200805648B (en) | 2009-09-30 |
JP5180099B2 (ja) | 2013-04-10 |
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