ZA200702098B - 1,5-Diphenylpyrazoles - Google Patents
1,5-Diphenylpyrazoles Download PDFInfo
- Publication number
- ZA200702098B ZA200702098B ZA200702098A ZA200702098A ZA200702098B ZA 200702098 B ZA200702098 B ZA 200702098B ZA 200702098 A ZA200702098 A ZA 200702098A ZA 200702098 A ZA200702098 A ZA 200702098A ZA 200702098 B ZA200702098 B ZA 200702098B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrazole
- dihydroxyphenyl
- hydroxy
- phenyl
- chlorophenyl
- Prior art date
Links
- IDCXLYCLPHRSAZ-UHFFFAOYSA-N 1,5-diphenylpyrazole Chemical class C=1C=CC=CC=1N1N=CC=C1C1=CC=CC=C1 IDCXLYCLPHRSAZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 46
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 201000010099 disease Diseases 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 23
- 210000004027 cell Anatomy 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 206010028980 Neoplasm Diseases 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 12
- 230000005764 inhibitory process Effects 0.000 claims description 11
- 201000009030 Carcinoma Diseases 0.000 claims description 8
- -1 p-methoxybenzyloxy Chemical group 0.000 claims description 8
- 230000012846 protein folding Effects 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 208000031886 HIV Infections Diseases 0.000 claims description 5
- 230000033115 angiogenesis Effects 0.000 claims description 5
- 230000033228 biological regulation Effects 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 208000009889 Herpes Simplex Diseases 0.000 claims description 4
- 241000725643 Respiratory syncytial virus Species 0.000 claims description 4
- 238000004220 aggregation Methods 0.000 claims description 4
- 206010025135 lupus erythematosus Diseases 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 230000003612 virological effect Effects 0.000 claims description 4
- 241000283690 Bos taurus Species 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 208000035473 Communicable disease Diseases 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 230000001364 causal effect Effects 0.000 claims description 3
- 230000001842 fibrogenetic effect Effects 0.000 claims description 3
- 208000002672 hepatitis B Diseases 0.000 claims description 3
- 208000028867 ischemia Diseases 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 201000003076 Angiosarcoma Diseases 0.000 claims description 2
- 206010003571 Astrocytoma Diseases 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 206010004146 Basal cell carcinoma Diseases 0.000 claims description 2
- 206010004593 Bile duct cancer Diseases 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
- 208000005243 Chondrosarcoma Diseases 0.000 claims description 2
- 201000009047 Chordoma Diseases 0.000 claims description 2
- 208000006332 Choriocarcinoma Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 241000709687 Coxsackievirus Species 0.000 claims description 2
- 208000009798 Craniopharyngioma Diseases 0.000 claims description 2
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims description 2
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims description 2
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- 241000701022 Cytomegalovirus Species 0.000 claims description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
- 241001466953 Echovirus Species 0.000 claims description 2
- 201000009273 Endometriosis Diseases 0.000 claims description 2
- 241000709661 Enterovirus Species 0.000 claims description 2
- 241000991587 Enterovirus C Species 0.000 claims description 2
- 206010014967 Ependymoma Diseases 0.000 claims description 2
- 208000006168 Ewing Sarcoma Diseases 0.000 claims description 2
- 201000008808 Fibrosarcoma Diseases 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- 208000032612 Glial tumor Diseases 0.000 claims description 2
- 206010018338 Glioma Diseases 0.000 claims description 2
- 208000001258 Hemangiosarcoma Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 2
- 208000000185 Localized scleroderma Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 241000712079 Measles morbillivirus Species 0.000 claims description 2
- 208000000172 Medulloblastoma Diseases 0.000 claims description 2
- 206010027406 Mesothelioma Diseases 0.000 claims description 2
- 208000034578 Multiple myelomas Diseases 0.000 claims description 2
- 241000711386 Mumps virus Species 0.000 claims description 2
- 206010029260 Neuroblastoma Diseases 0.000 claims description 2
- 201000010133 Oligodendroglioma Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 241001631646 Papillomaviridae Species 0.000 claims description 2
- 208000007641 Pinealoma Diseases 0.000 claims description 2
- 206010035148 Plague Diseases 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
- 201000000582 Retinoblastoma Diseases 0.000 claims description 2
- 241000702670 Rotavirus Species 0.000 claims description 2
- 241000710799 Rubella virus Species 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 201000010208 Seminoma Diseases 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
- 208000014070 Vestibular schwannoma Diseases 0.000 claims description 2
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 208000004064 acoustic neuroma Diseases 0.000 claims description 2
- 208000009956 adenocarcinoma Diseases 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 201000007180 bile duct carcinoma Diseases 0.000 claims description 2
- 201000001531 bladder carcinoma Diseases 0.000 claims description 2
- 208000003362 bronchogenic carcinoma Diseases 0.000 claims description 2
- 201000010881 cervical cancer Diseases 0.000 claims description 2
- 238000002512 chemotherapy Methods 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 208000002445 cystadenocarcinoma Diseases 0.000 claims description 2
- 208000037828 epithelial carcinoma Diseases 0.000 claims description 2
- 208000025750 heavy chain disease Diseases 0.000 claims description 2
- 201000002222 hemangioblastoma Diseases 0.000 claims description 2
- 201000011066 hemangioma Diseases 0.000 claims description 2
- 208000005252 hepatitis A Diseases 0.000 claims description 2
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
- 230000008629 immune suppression Effects 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 206010022000 influenza Diseases 0.000 claims description 2
- 201000006334 interstitial nephritis Diseases 0.000 claims description 2
- 208000011379 keloid formation Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 206010024627 liposarcoma Diseases 0.000 claims description 2
- 201000005296 lung carcinoma Diseases 0.000 claims description 2
- 208000037829 lymphangioendotheliosarcoma Diseases 0.000 claims description 2
- 208000012804 lymphangiosarcoma Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 206010027191 meningioma Diseases 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 208000001611 myxosarcoma Diseases 0.000 claims description 2
- 201000008026 nephroblastoma Diseases 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 claims description 2
- 201000008968 osteosarcoma Diseases 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 208000004019 papillary adenocarcinoma Diseases 0.000 claims description 2
- 201000010198 papillary carcinoma Diseases 0.000 claims description 2
- 208000024724 pineal body neoplasm Diseases 0.000 claims description 2
- 201000004123 pineal gland cancer Diseases 0.000 claims description 2
- 208000005987 polymyositis Diseases 0.000 claims description 2
- 230000004224 protection Effects 0.000 claims description 2
- 230000004845 protein aggregation Effects 0.000 claims description 2
- 230000008929 regeneration Effects 0.000 claims description 2
- 238000011069 regeneration method Methods 0.000 claims description 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 208000008864 scrapie Diseases 0.000 claims description 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 206010042863 synovial sarcoma Diseases 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- 230000002381 testicular Effects 0.000 claims description 2
- 231100000419 toxicity Toxicity 0.000 claims description 2
- 230000001988 toxicity Effects 0.000 claims description 2
- 210000004881 tumor cell Anatomy 0.000 claims description 2
- 241000701161 unidentified adenovirus Species 0.000 claims description 2
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims description 2
- 244000052613 viral pathogen Species 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 28
- 239000012453 solvate Substances 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- MQPJENKLXPDGRC-UHFFFAOYSA-N 2,4-dihydroxy-N-methyl-5-[2-[4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]pyrazol-3-yl]-N-propylbenzamide Chemical compound C1=C(O)C(C(=O)N(C)CCC)=CC(C=2N(N=CC=2)C=2C=CC(OCCN3CCN(C)CC3)=CC=2)=C1O MQPJENKLXPDGRC-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- KBISKQRMAVEGRM-UHFFFAOYSA-N 2-[2-(2-aminophenyl)pyrazol-3-yl]-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=CC=C1N KBISKQRMAVEGRM-UHFFFAOYSA-N 0.000 claims 1
- HZHHYNUCSGAYRY-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)pyrazol-3-yl]-5-fluorophenol Chemical compound OC1=CC(F)=CC=C1C1=CC=NN1C1=CC=CC=C1Cl HZHHYNUCSGAYRY-UHFFFAOYSA-N 0.000 claims 1
- YAJUBFLISJNOLR-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)pyrazol-3-yl]-5-methoxy-4-phenylsulfanylphenol Chemical compound COC1=CC(O)=C(C=2N(N=CC=2)C=2C(=CC=CC=2)Cl)C=C1SC1=CC=CC=C1 YAJUBFLISJNOLR-UHFFFAOYSA-N 0.000 claims 1
- WZGNPQAUXLKTIU-UHFFFAOYSA-N 2-[2-(2-ethylphenyl)pyrazol-3-yl]-5-fluorophenol Chemical compound CCC1=CC=CC=C1N1C(C=2C(=CC(F)=CC=2)O)=CC=N1 WZGNPQAUXLKTIU-UHFFFAOYSA-N 0.000 claims 1
- QNZHGUBWIGVGQL-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)pyrazol-3-yl]-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=CC=C1F QNZHGUBWIGVGQL-UHFFFAOYSA-N 0.000 claims 1
- LTHYBLYRHBZEAS-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)pyrazol-3-yl]-5-fluorophenol Chemical compound C1=C(Cl)C(C)=CC=C1N1C(C=2C(=CC(F)=CC=2)O)=CC=N1 LTHYBLYRHBZEAS-UHFFFAOYSA-N 0.000 claims 1
- GWYVHZMOGKCNRO-UHFFFAOYSA-N 2-[2-(3-chloro-4-methylphenyl)pyrazol-3-yl]-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=C(C)C(Cl)=C1 GWYVHZMOGKCNRO-UHFFFAOYSA-N 0.000 claims 1
- FCTOKOGOLHDKRD-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)pyrazol-3-yl]-5-fluorophenol Chemical compound OC1=CC(F)=CC=C1C1=CC=NN1C1=CC=CC(Cl)=C1 FCTOKOGOLHDKRD-UHFFFAOYSA-N 0.000 claims 1
- SZORKPUBCDWUCS-UHFFFAOYSA-N 2-[2-(4-aminophenyl)pyrazol-3-yl]-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=C(N)C=C1 SZORKPUBCDWUCS-UHFFFAOYSA-N 0.000 claims 1
- WUWGPXRBAPUKQR-UHFFFAOYSA-N 2-[2-(4-bromophenyl)pyrazol-3-yl]-5-fluorophenol Chemical compound OC1=CC(F)=CC=C1C1=CC=NN1C1=CC=C(Br)C=C1 WUWGPXRBAPUKQR-UHFFFAOYSA-N 0.000 claims 1
- BSESSSOJSOJMBQ-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)pyrazol-3-yl]-5-fluorophenol Chemical compound OC1=CC(F)=CC=C1C1=CC=NN1C1=CC=C(Cl)C=C1 BSESSSOJSOJMBQ-UHFFFAOYSA-N 0.000 claims 1
- FLZDHVVIEJCKKI-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)pyrazol-3-yl]-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=C(Cl)C=C1 FLZDHVVIEJCKKI-UHFFFAOYSA-N 0.000 claims 1
- RWBMGGNDJCJXQB-UHFFFAOYSA-N 3-[5-(2,4-dihydroxyphenyl)pyrazol-1-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(N2C(=CC=N2)C=2C(=CC(O)=CC=2)O)=C1 RWBMGGNDJCJXQB-UHFFFAOYSA-N 0.000 claims 1
- PRIKFEMMBOAFQA-UHFFFAOYSA-N 3-[5-(2,4-dihydroxyphenyl)pyrazol-1-yl]benzonitrile Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=CC(C#N)=C1 PRIKFEMMBOAFQA-UHFFFAOYSA-N 0.000 claims 1
- UQORMSFORAMRSL-UHFFFAOYSA-N 3-[5-(4-fluoro-2-hydroxyphenyl)pyrazol-1-yl]benzonitrile Chemical compound OC1=CC(F)=CC=C1C1=CC=NN1C1=CC=CC(C#N)=C1 UQORMSFORAMRSL-UHFFFAOYSA-N 0.000 claims 1
- CTKVJWGTJBBKEM-UHFFFAOYSA-N 4-(2-fluorophenyl)sulfanyl-5-methoxy-2-[2-(4-nitrophenyl)pyrazol-3-yl]phenol Chemical compound COC1=CC(O)=C(C=2N(N=CC=2)C=2C=CC(=CC=2)[N+]([O-])=O)C=C1SC1=CC=CC=C1F CTKVJWGTJBBKEM-UHFFFAOYSA-N 0.000 claims 1
- PHXOKKWNTRTQTI-UHFFFAOYSA-N 4-(2-phenylpyrazol-3-yl)benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=CC=C1 PHXOKKWNTRTQTI-UHFFFAOYSA-N 0.000 claims 1
- WXRCEPYDWLAMPZ-UHFFFAOYSA-N 4-[1-(4-fluorophenyl)ethyl]-6-(2-phenylpyrazol-3-yl)benzene-1,3-diol Chemical compound C=1C(C=2N(N=CC=2)C=2C=CC=CC=2)=C(O)C=C(O)C=1C(C)C1=CC=C(F)C=C1 WXRCEPYDWLAMPZ-UHFFFAOYSA-N 0.000 claims 1
- DFLLTFIVFGNCEA-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)pyrazol-3-yl]-6-[2-(4-methylphenyl)ethyl]benzene-1,3-diol Chemical compound C1=CC(C)=CC=C1CCC1=CC(C=2N(N=CC=2)C=2C=C3OCCOC3=CC=2)=C(O)C=C1O DFLLTFIVFGNCEA-UHFFFAOYSA-N 0.000 claims 1
- PYVACOMHCAMMAT-UHFFFAOYSA-N 4-[2-(2,6-dichlorophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=C(Cl)C=CC=C1Cl PYVACOMHCAMMAT-UHFFFAOYSA-N 0.000 claims 1
- MDZAJHSAKUOMOL-UHFFFAOYSA-N 4-[2-(2,6-difluorophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=C(F)C=CC=C1F MDZAJHSAKUOMOL-UHFFFAOYSA-N 0.000 claims 1
- FJMGMLIDKNOGTR-UHFFFAOYSA-N 4-[2-(2-aminophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound NC1=CC=CC=C1N1C(C=2C(=CC(O)=CC=2)O)=CC=N1 FJMGMLIDKNOGTR-UHFFFAOYSA-N 0.000 claims 1
- JTALCEZAZYNQIX-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)ethyl]-6-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=C(C=2N(N=CC=2)C=2C=C3OCCOC3=CC=2)C=C1CCC1=CC=CC=C1Cl JTALCEZAZYNQIX-UHFFFAOYSA-N 0.000 claims 1
- RAWDXXVVKNWFMO-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)pyrazol-3-yl]-6-(2-fluoropropyl)benzene-1,3-diol Chemical compound C1=C(O)C(CC(F)C)=CC(C=2N(N=CC=2)C=2C(=CC=CC=2)Cl)=C1O RAWDXXVVKNWFMO-UHFFFAOYSA-N 0.000 claims 1
- XKWFQNKDUUWEFR-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)pyrazol-3-yl]-6-(2-pyridin-2-ylethyl)benzene-1,3-diol Chemical compound OC1=CC(O)=C(C=2N(N=CC=2)C=2C(=CC=CC=2)Cl)C=C1CCC1=CC=CC=N1 XKWFQNKDUUWEFR-UHFFFAOYSA-N 0.000 claims 1
- OPGACFWJMLILHY-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)pyrazol-3-yl]-6-(pyridin-2-ylmethylamino)benzene-1,3-diol Chemical compound OC1=CC(O)=C(C=2N(N=CC=2)C=2C(=CC=CC=2)Cl)C=C1NCC1=CC=CC=N1 OPGACFWJMLILHY-UHFFFAOYSA-N 0.000 claims 1
- IKEBBSQACJRIAP-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)pyrazol-3-yl]-6-[(4-fluorophenyl)methoxy]benzene-1,3-diol Chemical compound OC1=CC(O)=C(C=2N(N=CC=2)C=2C(=CC=CC=2)Cl)C=C1OCC1=CC=C(F)C=C1 IKEBBSQACJRIAP-UHFFFAOYSA-N 0.000 claims 1
- WQHVHFYVCZXYNS-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)pyrazol-3-yl]-6-[2-(2-fluorophenyl)ethyl]benzene-1,3-diol Chemical compound OC1=CC(O)=C(C=2N(N=CC=2)C=2C(=CC=CC=2)Cl)C=C1CCC1=CC=CC=C1F WQHVHFYVCZXYNS-UHFFFAOYSA-N 0.000 claims 1
- BJDFJILFCVPXJI-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)pyrazol-3-yl]-6-[2-(3-fluorophenyl)ethyl]benzene-1,3-diol Chemical compound OC1=CC(O)=C(C=2N(N=CC=2)C=2C(=CC=CC=2)Cl)C=C1CCC1=CC=CC(F)=C1 BJDFJILFCVPXJI-UHFFFAOYSA-N 0.000 claims 1
- XTBNIJVTOSWFKP-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)pyrazol-3-yl]-6-[2-(hydroxymethyl)piperidin-1-yl]sulfonylbenzene-1,3-diol Chemical compound OCC1CCCCN1S(=O)(=O)C1=CC(C=2N(N=CC=2)C=2C(=CC=CC=2)Cl)=C(O)C=C1O XTBNIJVTOSWFKP-UHFFFAOYSA-N 0.000 claims 1
- PTRIWRKMDXDOTQ-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)pyrazol-3-yl]-6-morpholin-4-ylsulfonylbenzene-1,3-diol Chemical compound OC1=CC(O)=C(S(=O)(=O)N2CCOCC2)C=C1C1=CC=NN1C1=CC=CC=C1Cl PTRIWRKMDXDOTQ-UHFFFAOYSA-N 0.000 claims 1
- SLSMPZVQZGBOOY-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)pyrazol-3-yl]-6-phenylbenzene-1,3-diol Chemical compound OC1=CC(O)=C(C=2C=CC=CC=2)C=C1C1=CC=NN1C1=CC=CC=C1Cl SLSMPZVQZGBOOY-UHFFFAOYSA-N 0.000 claims 1
- NXZPXDLYOVGQMR-UHFFFAOYSA-N 4-[2-(2-chlorophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=CC=C1Cl NXZPXDLYOVGQMR-UHFFFAOYSA-N 0.000 claims 1
- VNPQXXSQPZEVPB-UHFFFAOYSA-N 4-[2-(2-ethylphenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound CCC1=CC=CC=C1N1C(C=2C(=CC(O)=CC=2)O)=CC=N1 VNPQXXSQPZEVPB-UHFFFAOYSA-N 0.000 claims 1
- AKPHNAWWNHCCKQ-UHFFFAOYSA-N 4-[2-(2-fluorophenyl)pyrazol-3-yl]-6-(2-methoxy-2-phenylethyl)benzene-1,3-diol Chemical compound C=1C=CC=CC=1C(OC)CC(C(=CC=1O)O)=CC=1C1=CC=NN1C1=CC=CC=C1F AKPHNAWWNHCCKQ-UHFFFAOYSA-N 0.000 claims 1
- WKVUIZOLMMARBF-UHFFFAOYSA-N 4-[2-(2-fluorophenyl)pyrazol-3-yl]-6-[(4-methoxyphenyl)sulfonylmethyl]benzene-1,3-diol Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC1=CC(C=2N(N=CC=2)C=2C(=CC=CC=2)F)=C(O)C=C1O WKVUIZOLMMARBF-UHFFFAOYSA-N 0.000 claims 1
- PNRWSJCMZMBTOG-UHFFFAOYSA-N 4-[2-(2-fluorophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=CC=C1F PNRWSJCMZMBTOG-UHFFFAOYSA-N 0.000 claims 1
- WAZCTAMHGCTGEZ-UHFFFAOYSA-N 4-[2-(2-nitrophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=CC=C1[N+]([O-])=O WAZCTAMHGCTGEZ-UHFFFAOYSA-N 0.000 claims 1
- WGUZXAZENVSHQL-UHFFFAOYSA-N 4-[2-(3,5-dichlorophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC(Cl)=CC(Cl)=C1 WGUZXAZENVSHQL-UHFFFAOYSA-N 0.000 claims 1
- BTQRQSUSNLWOIY-UHFFFAOYSA-N 4-[2-(3-fluorophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=CC(F)=C1 BTQRQSUSNLWOIY-UHFFFAOYSA-N 0.000 claims 1
- NFTHTJOZZVSPGV-UHFFFAOYSA-N 4-[2-(3-hydroxyphenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC=CC(N2C(=CC=N2)C=2C(=CC(O)=CC=2)O)=C1 NFTHTJOZZVSPGV-UHFFFAOYSA-N 0.000 claims 1
- IOKDKKLVCQSIKK-UHFFFAOYSA-N 4-[2-(3-methylphenyl)pyrazol-3-yl]-6-phenylsulfanylbenzene-1,3-diol Chemical compound CC1=CC=CC(N2C(=CC=N2)C=2C(=CC(O)=C(SC=3C=CC=CC=3)C=2)O)=C1 IOKDKKLVCQSIKK-UHFFFAOYSA-N 0.000 claims 1
- WCOOIPCAPZYEMO-UHFFFAOYSA-N 4-[2-(3-nitrophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=CC([N+]([O-])=O)=C1 WCOOIPCAPZYEMO-UHFFFAOYSA-N 0.000 claims 1
- JOROFCSCDAEIGW-UHFFFAOYSA-N 4-[2-(4-aminophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound C1=CC(N)=CC=C1N1C(C=2C(=CC(O)=CC=2)O)=CC=N1 JOROFCSCDAEIGW-UHFFFAOYSA-N 0.000 claims 1
- UMEPRPFDQFLDDE-UHFFFAOYSA-N 4-[2-(4-bromophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=C(Br)C=C1 UMEPRPFDQFLDDE-UHFFFAOYSA-N 0.000 claims 1
- WPNBTHLLICXESI-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=C(Cl)C=C1 WPNBTHLLICXESI-UHFFFAOYSA-N 0.000 claims 1
- GRYDYYBMHYKGPY-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound C1=CC(O)=CC=C1N1C(C=2C(=CC(O)=CC=2)O)=CC=N1 GRYDYYBMHYKGPY-UHFFFAOYSA-N 0.000 claims 1
- UKXLYUXMKCXMDR-UHFFFAOYSA-N 4-[2-(4-methylphenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound C1=CC(C)=CC=C1N1C(C=2C(=CC(O)=CC=2)O)=CC=N1 UKXLYUXMKCXMDR-UHFFFAOYSA-N 0.000 claims 1
- YPTSQGFQTVBIMI-UHFFFAOYSA-N 4-[2-[2-nitro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O YPTSQGFQTVBIMI-UHFFFAOYSA-N 0.000 claims 1
- BGLYNIKOSOUHBJ-UHFFFAOYSA-N 4-[5-(2,4-dihydroxyphenyl)pyrazol-1-yl]-3-nitrobenzonitrile Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=C(C#N)C=C1[N+]([O-])=O BGLYNIKOSOUHBJ-UHFFFAOYSA-N 0.000 claims 1
- JSECODIJDMLRTQ-UHFFFAOYSA-N 4-[5-(2,4-dihydroxyphenyl)pyrazol-1-yl]-N-propylbenzamide Chemical compound C1=CC(C(=O)NCCC)=CC=C1N1C(C=2C(=CC(O)=CC=2)O)=CC=N1 JSECODIJDMLRTQ-UHFFFAOYSA-N 0.000 claims 1
- ZWIMNALRSOOABQ-UHFFFAOYSA-N 4-[5-(2,4-dihydroxyphenyl)pyrazol-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C(C=2C(=CC(O)=CC=2)O)=CC=N1 ZWIMNALRSOOABQ-UHFFFAOYSA-N 0.000 claims 1
- NLTZUNMRFDTCCO-UHFFFAOYSA-N 4-[5-(2,4-dihydroxyphenyl)pyrazol-1-yl]benzonitrile Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C1=CC=C(C#N)C=C1 NLTZUNMRFDTCCO-UHFFFAOYSA-N 0.000 claims 1
- LSDDCDLHYFBSSM-UHFFFAOYSA-N 4-[5-(2,4-dimethoxyphenyl)pyrazol-1-yl]aniline Chemical compound COC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=C(N)C=C1 LSDDCDLHYFBSSM-UHFFFAOYSA-N 0.000 claims 1
- AJTZYDQAYFXSFO-UHFFFAOYSA-N 4-[5-(2-hydroxy-4-methoxyphenyl)pyrazol-1-yl]benzonitrile Chemical compound OC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=C(C#N)C=C1 AJTZYDQAYFXSFO-UHFFFAOYSA-N 0.000 claims 1
- OLLPSFLCCMUXNW-UHFFFAOYSA-N 4-[5-(4-fluoro-2-hydroxyphenyl)pyrazol-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C(C=2C(=CC(F)=CC=2)O)=CC=N1 OLLPSFLCCMUXNW-UHFFFAOYSA-N 0.000 claims 1
- VTWMZMAEKSAVML-UHFFFAOYSA-N 4-[5-(4-fluoro-2-hydroxyphenyl)pyrazol-1-yl]benzonitrile Chemical compound OC1=CC(F)=CC=C1C1=CC=NN1C1=CC=C(C#N)C=C1 VTWMZMAEKSAVML-UHFFFAOYSA-N 0.000 claims 1
- ROIJHOWPTMDYSX-UHFFFAOYSA-N 4-[5-[2,4-bis(phenylmethoxy)phenyl]pyrazol-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C(C=2C(=CC(OCC=3C=CC=CC=3)=CC=2)OCC=2C=CC=CC=2)=CC=N1 ROIJHOWPTMDYSX-UHFFFAOYSA-N 0.000 claims 1
- LDULRVUBDTXKRW-UHFFFAOYSA-N 4-benzyl-6-[2-(2-chlorophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=C(C=2N(N=CC=2)C=2C(=CC=CC=2)Cl)C=C1CC1=CC=CC=C1 LDULRVUBDTXKRW-UHFFFAOYSA-N 0.000 claims 1
- LDEUHTMEKXHOCP-UHFFFAOYSA-N 4-bromo-6-[2-(2-chlorophenyl)pyrazol-3-yl]benzene-1,3-diol Chemical compound C1=C(Br)C(O)=CC(O)=C1C1=CC=NN1C1=CC=CC=C1Cl LDEUHTMEKXHOCP-UHFFFAOYSA-N 0.000 claims 1
- MMOWXHKNQZKRGK-UHFFFAOYSA-N 4-chloro-5-methyl-2-(2-phenylpyrazol-3-yl)phenol Chemical compound C1=C(Cl)C(C)=CC(O)=C1C1=CC=NN1C1=CC=CC=C1 MMOWXHKNQZKRGK-UHFFFAOYSA-N 0.000 claims 1
- MUVARASWBFVKDA-UHFFFAOYSA-N 5-(2,4-dimethoxyphenyl)-1-(4-nitrophenyl)pyrazole Chemical compound COC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=C([N+]([O-])=O)C=C1 MUVARASWBFVKDA-UHFFFAOYSA-N 0.000 claims 1
- RUHWZVWFLKYHOB-UHFFFAOYSA-N 5-[2-(2-chlorophenyl)pyrazol-3-yl]-2,4-dihydroxy-N-pyridin-3-ylbenzenesulfonamide Chemical compound OC1=CC(O)=C(S(=O)(=O)NC=2C=NC=CC=2)C=C1C1=CC=NN1C1=CC=CC=C1Cl RUHWZVWFLKYHOB-UHFFFAOYSA-N 0.000 claims 1
- JHHZIIHCZAFOLQ-UHFFFAOYSA-N 5-fluoro-2-(2-phenylpyrazol-3-yl)phenol Chemical compound OC1=CC(F)=CC=C1C1=CC=NN1C1=CC=CC=C1 JHHZIIHCZAFOLQ-UHFFFAOYSA-N 0.000 claims 1
- HNJCBIVJPWEKTG-UHFFFAOYSA-N 5-fluoro-2-[2-(2-methoxyphenyl)pyrazol-3-yl]phenol Chemical compound COC1=CC=CC=C1N1C(C=2C(=CC(F)=CC=2)O)=CC=N1 HNJCBIVJPWEKTG-UHFFFAOYSA-N 0.000 claims 1
- GJXKKFQRJPLLRY-UHFFFAOYSA-N 5-fluoro-2-[2-(3-fluorophenyl)pyrazol-3-yl]phenol Chemical compound OC1=CC(F)=CC=C1C1=CC=NN1C1=CC=CC(F)=C1 GJXKKFQRJPLLRY-UHFFFAOYSA-N 0.000 claims 1
- LVCNRFCKQXRJQA-UHFFFAOYSA-N 5-fluoro-2-[2-(3-methoxyphenyl)pyrazol-3-yl]phenol Chemical compound COC1=CC=CC(N2C(=CC=N2)C=2C(=CC(F)=CC=2)O)=C1 LVCNRFCKQXRJQA-UHFFFAOYSA-N 0.000 claims 1
- GMAHECNKCAMFPG-UHFFFAOYSA-N 5-fluoro-2-[2-(4-methoxyphenyl)pyrazol-3-yl]phenol Chemical compound C1=CC(OC)=CC=C1N1C(C=2C(=CC(F)=CC=2)O)=CC=N1 GMAHECNKCAMFPG-UHFFFAOYSA-N 0.000 claims 1
- FMJNNCUZOXVUPG-UHFFFAOYSA-N 5-fluoro-2-[2-(4-methylphenyl)pyrazol-3-yl]phenol Chemical compound C1=CC(C)=CC=C1N1C(C=2C(=CC(F)=CC=2)O)=CC=N1 FMJNNCUZOXVUPG-UHFFFAOYSA-N 0.000 claims 1
- WIRMRYCQDFIANE-UHFFFAOYSA-N 5-fluoro-2-[2-[3-(trifluoromethyl)phenyl]pyrazol-3-yl]phenol Chemical compound OC1=CC(F)=CC=C1C1=CC=NN1C1=CC=CC(C(F)(F)F)=C1 WIRMRYCQDFIANE-UHFFFAOYSA-N 0.000 claims 1
- RJDOAAHVSUONPU-UHFFFAOYSA-N 5-fluoro-2-[2-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]phenol Chemical compound OC1=CC(F)=CC=C1C1=CC=NN1C1=CC=C(C(F)(F)F)C=C1 RJDOAAHVSUONPU-UHFFFAOYSA-N 0.000 claims 1
- SSMSWAWUFBNYSK-UHFFFAOYSA-N 5-methoxy-2-(2-phenylpyrazol-3-yl)phenol Chemical compound OC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=CC=C1 SSMSWAWUFBNYSK-UHFFFAOYSA-N 0.000 claims 1
- AELZAJMTFIOHGC-UHFFFAOYSA-N 5-methoxy-2-[2-(2-nitrophenyl)pyrazol-3-yl]phenol Chemical compound OC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=CC=C1[N+]([O-])=O AELZAJMTFIOHGC-UHFFFAOYSA-N 0.000 claims 1
- AONYTLQZERKMOG-UHFFFAOYSA-N 5-methoxy-2-[2-(3-nitrophenyl)pyrazol-3-yl]phenol Chemical compound OC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=CC([N+]([O-])=O)=C1 AONYTLQZERKMOG-UHFFFAOYSA-N 0.000 claims 1
- SHQPPPDMSCBENL-UHFFFAOYSA-N 5-methoxy-2-[2-[2-nitro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]phenol Chemical compound OC1=CC(OC)=CC=C1C1=CC=NN1C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O SHQPPPDMSCBENL-UHFFFAOYSA-N 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- ORKOZADYLCVUFA-UHFFFAOYSA-N N-[4-[5-(2,4-dihydroxyphenyl)pyrazol-1-yl]phenyl]-2-phenylacetamide Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C(C=C1)=CC=C1NC(=O)CC1=CC=CC=C1 ORKOZADYLCVUFA-UHFFFAOYSA-N 0.000 claims 1
- KFDDXNJQZJIDEF-UHFFFAOYSA-N N-[4-[5-(2,4-dihydroxyphenyl)pyrazol-1-yl]phenyl]pyridine-4-carboxamide Chemical compound OC1=CC(O)=CC=C1C1=CC=NN1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1 KFDDXNJQZJIDEF-UHFFFAOYSA-N 0.000 claims 1
- QUASUYQNSIXGJL-UHFFFAOYSA-N N-ethyl-2,4-dihydroxy-5-[2-(2-methylphenyl)pyrazol-3-yl]benzenesulfonamide Chemical compound C1=C(O)C(S(=O)(=O)NCC)=CC(C=2N(N=CC=2)C=2C(=CC=CC=2)C)=C1O QUASUYQNSIXGJL-UHFFFAOYSA-N 0.000 claims 1
- IULVQUFRTVQVSY-UHFFFAOYSA-N OC1=C(C=CC(=C1)OC)C1=CC=NN1C1=C(C=CC=C1)N.OC1=C(C=CC(=C1)OC)C1=CC=NN1C1=C(C=CC=C1)[N+](=O)[O-] Chemical compound OC1=C(C=CC(=C1)OC)C1=CC=NN1C1=C(C=CC=C1)N.OC1=C(C=CC(=C1)OC)C1=CC=NN1C1=C(C=CC=C1)[N+](=O)[O-] IULVQUFRTVQVSY-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 210000001185 bone marrow Anatomy 0.000 claims 1
- 230000005907 cancer growth Effects 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 238000005661 deetherification reaction Methods 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- VMYJXHCSMQIPAU-UHFFFAOYSA-N n-[4-[5-(2,4-dimethoxyphenyl)pyrazol-1-yl]phenyl]-2-phenylacetamide Chemical compound COC1=CC(OC)=CC=C1C1=CC=NN1C(C=C1)=CC=C1NC(=O)CC1=CC=CC=C1 VMYJXHCSMQIPAU-UHFFFAOYSA-N 0.000 claims 1
- JIVJHTFCNJZIRM-UHFFFAOYSA-N n-[4-[5-(2,4-dimethoxyphenyl)pyrazol-1-yl]phenyl]pyridine-4-carboxamide Chemical compound COC1=CC(OC)=CC=C1C1=CC=NN1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1 JIVJHTFCNJZIRM-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 101710113864 Heat shock protein 90 Proteins 0.000 description 32
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 description 32
- 108090000623 proteins and genes Proteins 0.000 description 30
- 235000018102 proteins Nutrition 0.000 description 27
- 102000004169 proteins and genes Human genes 0.000 description 27
- 108010004889 Heat-Shock Proteins Proteins 0.000 description 11
- 102000002812 Heat-Shock Proteins Human genes 0.000 description 11
- 108010006519 Molecular Chaperones Proteins 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 102100039328 Endoplasmin Human genes 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- 230000006870 function Effects 0.000 description 7
- 108010017007 glucose-regulated proteins Proteins 0.000 description 7
- 230000027455 binding Effects 0.000 description 6
- 238000009739 binding Methods 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 6
- QTQAWLPCGQOSGP-GBTDJJJQSA-N geldanamycin Chemical class N1C(=O)\C(C)=C/C=C\[C@@H](OC)[C@H](OC(N)=O)\C(C)=C/[C@@H](C)[C@@H](O)[C@H](OC)C[C@@H](C)CC2=C(OC)C(=O)C=C1C2=O QTQAWLPCGQOSGP-GBTDJJJQSA-N 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 5
- VYGYNVZNSSTDLJ-HKCOAVLJSA-N monorden Natural products CC1CC2OC2C=C/C=C/C(=O)CC3C(C(=CC(=C3Cl)O)O)C(=O)O1 VYGYNVZNSSTDLJ-HKCOAVLJSA-N 0.000 description 5
- AECPBJMOGBFQDN-YMYQVXQQSA-N radicicol Chemical compound C1CCCC(=O)C[C@H]2[C@H](Cl)C(=O)CC(=O)[C@H]2C(=O)O[C@H](C)C[C@H]2O[C@@H]21 AECPBJMOGBFQDN-YMYQVXQQSA-N 0.000 description 5
- 229930192524 radicicol Natural products 0.000 description 5
- 108091006112 ATPases Proteins 0.000 description 4
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 4
- JRZJKWGQFNTSRN-UHFFFAOYSA-N Geldanamycin Natural products C1C(C)CC(OC)C(O)C(C)C=C(C)C(OC(N)=O)C(OC)CCC=C(C)C(=O)NC2=CC(=O)C(OC)=C1C2=O JRZJKWGQFNTSRN-UHFFFAOYSA-N 0.000 description 4
- 208000010496 Heart Arrest Diseases 0.000 description 4
- 102000005431 Molecular Chaperones Human genes 0.000 description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 230000035882 stress Effects 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 102100026973 Heat shock protein 75 kDa, mitochondrial Human genes 0.000 description 3
- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 3
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 3
- 208000006011 Stroke Diseases 0.000 description 3
- 102000018594 Tumour necrosis factor Human genes 0.000 description 3
- 108050007852 Tumour necrosis factor Proteins 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 230000006355 external stress Effects 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 230000000302 ischemic effect Effects 0.000 description 3
- 230000004807 localization Effects 0.000 description 3
- 150000003212 purines Chemical class 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 210000003660 reticulum Anatomy 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 2
- 206010019196 Head injury Diseases 0.000 description 2
- 208000016988 Hemorrhagic Stroke Diseases 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 208000023105 Huntington disease Diseases 0.000 description 2
- 208000013016 Hypoglycemia Diseases 0.000 description 2
- 206010021118 Hypotonia Diseases 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- 208000007379 Muscle Hypotonia Diseases 0.000 description 2
- YJQPYGGHQPGBLI-UHFFFAOYSA-N Novobiocin Natural products O1C(C)(C)C(OC)C(OC(N)=O)C(O)C1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-UHFFFAOYSA-N 0.000 description 2
- 101710204707 Transforming growth factor-beta receptor-associated protein 1 Proteins 0.000 description 2
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 230000006907 apoptotic process Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000002612 cardiopulmonary effect Effects 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000012866 crystallographic experiment Methods 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 210000002950 fibroblast Anatomy 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 239000003481 heat shock protein 90 inhibitor Substances 0.000 description 2
- 101150072994 hsp30 gene Proteins 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 208000001286 intracranial vasospasm Diseases 0.000 description 2
- 230000003211 malignant effect Effects 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- YJQPYGGHQPGBLI-KGSXXDOSSA-N novobiocin Chemical compound O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-KGSXXDOSSA-N 0.000 description 2
- 229960002950 novobiocin Drugs 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 229940076155 protein modulator Drugs 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 201000000980 schizophrenia Diseases 0.000 description 2
- 210000000278 spinal cord Anatomy 0.000 description 2
- 208000005809 status epilepticus Diseases 0.000 description 2
- AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- 230000006663 ubiquitin-proteasome pathway Effects 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 101710163595 Chaperone protein DnaK Proteins 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 1
- 102000013701 Cyclin-Dependent Kinase 4 Human genes 0.000 description 1
- 108010054814 DNA Gyrase Proteins 0.000 description 1
- 101100016370 Danio rerio hsp90a.1 gene Proteins 0.000 description 1
- 101100285708 Dictyostelium discoideum hspD gene Proteins 0.000 description 1
- 206010014498 Embolic stroke Diseases 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 102000005623 HSP27 Heat-Shock Proteins Human genes 0.000 description 1
- 108010045100 HSP27 Heat-Shock Proteins Proteins 0.000 description 1
- 101710178376 Heat shock 70 kDa protein Proteins 0.000 description 1
- 101710152018 Heat shock cognate 70 kDa protein Proteins 0.000 description 1
- 102100039170 Heat shock protein beta-6 Human genes 0.000 description 1
- 101710100489 Heat shock protein beta-6 Proteins 0.000 description 1
- MCAHMSDENAOJFZ-UHFFFAOYSA-N Herbimycin A Natural products N1C(=O)C(C)=CC=CC(OC)C(OC(N)=O)C(C)=CC(C)C(OC)C(OC)CC(C)C(OC)C2=CC(=O)C=C1C2=O MCAHMSDENAOJFZ-UHFFFAOYSA-N 0.000 description 1
- 101000763352 Homo sapiens Heat shock protein 75 kDa, mitochondrial Proteins 0.000 description 1
- 101001047681 Homo sapiens Tyrosine-protein kinase Lck Proteins 0.000 description 1
- 125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 108010058765 Oncogene Protein pp60(v-src) Proteins 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 208000024777 Prion disease Diseases 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 102100033479 RAF proto-oncogene serine/threonine-protein kinase Human genes 0.000 description 1
- 101710141955 RAF proto-oncogene serine/threonine-protein kinase Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 108050002653 Retinoblastoma protein Proteins 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 101100071627 Schizosaccharomyces pombe (strain 972 / ATCC 24843) swo1 gene Proteins 0.000 description 1
- 108010017842 Telomerase Proteins 0.000 description 1
- 102100024036 Tyrosine-protein kinase Lck Human genes 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- FPQFYIAXQDXNOR-QDKLYSGJSA-N alpha-Zearalenol Chemical class O=C1O[C@@H](C)CCC[C@H](O)CCC\C=C\C2=CC(O)=CC(O)=C21 FPQFYIAXQDXNOR-QDKLYSGJSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000003851 biochemical process Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 230000025084 cell cycle arrest Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000004637 cellular stress Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000002074 deregulated effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 108091006104 gene-regulatory proteins Proteins 0.000 description 1
- 102000034356 gene-regulatory proteins Human genes 0.000 description 1
- 230000008642 heat stress Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- MCAHMSDENAOJFZ-BVXDHVRPSA-N herbimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](OC)[C@@H](OC)C[C@H](C)[C@@H](OC)C2=CC(=O)C=C1C2=O MCAHMSDENAOJFZ-BVXDHVRPSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 230000004879 molecular function Effects 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 230000005959 oncogenic signaling Effects 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000009979 protective mechanism Effects 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 230000015909 regulation of biological process Effects 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000008684 selective degradation Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 108009000000 signalling pathways Proteins 0.000 description 1
- 108700026239 src Genes Proteins 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A61P25/12—Antiepileptics; Anticonvulsants for grand-mal
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- 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
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Biotechnology (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004039280A DE102004039280A1 (de) | 2004-08-13 | 2004-08-13 | 1,5-Diphenyl-pyrazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200702098B true ZA200702098B (en) | 2008-07-30 |
Family
ID=35262026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200702098A ZA200702098B (en) | 2004-08-13 | 2007-03-12 | 1,5-Diphenylpyrazoles |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7932401B2 (es) |
| EP (1) | EP1776346B1 (es) |
| JP (1) | JP4879895B2 (es) |
| KR (1) | KR20070040811A (es) |
| CN (1) | CN101006061A (es) |
| AR (1) | AR050454A1 (es) |
| AU (1) | AU2005274540B2 (es) |
| BR (1) | BRPI0514295A (es) |
| CA (1) | CA2576531C (es) |
| DE (1) | DE102004039280A1 (es) |
| ES (1) | ES2426189T3 (es) |
| MX (1) | MX2007001692A (es) |
| RU (1) | RU2007108859A (es) |
| WO (1) | WO2006018082A1 (es) |
| ZA (1) | ZA200702098B (es) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2007005940A (es) | 2004-11-18 | 2007-06-19 | Synta Pharmaceuticals Corp | Compuestos de triazol que modulan la actividad hsp90. |
| JP2008540395A (ja) * | 2005-05-03 | 2008-11-20 | ファイザー・インク | アミドレソルシノール化合物 |
| DE102006023336A1 (de) * | 2006-05-18 | 2007-11-22 | Merck Patent Gmbh | 1,5-Diphenyl-pyrazole II |
| DE102006023337A1 (de) * | 2006-05-18 | 2007-11-22 | Merck Patent Gmbh | Triazolderivate II |
| FR2907453B1 (fr) | 2006-10-24 | 2008-12-26 | Sanofi Aventis Sa | Nouveaux derives du fluorene,compositions les contenant et utilisation |
| US7932279B2 (en) | 2007-10-12 | 2011-04-26 | Arqule, Inc. | Substituted tetrazole compounds and uses thereof |
| LT5623B (lt) * | 2008-04-30 | 2010-01-25 | Biotechnologijos Institutas, , | 5-aril-4-(5-pakeistieji 2,4-dihidroksifenil)-1,2,3-tiadiazolai kaip hsp90 šaperono slopikliai ir tarpiniai junginiai jiems gauti |
| AR077405A1 (es) | 2009-07-10 | 2011-08-24 | Sanofi Aventis | Derivados del indol inhibidores de hsp90, composiciones que los contienen y utilizacion de los mismos para el tratamiento del cancer |
| FR2949467B1 (fr) | 2009-09-03 | 2011-11-25 | Sanofi Aventis | Nouveaux derives de 5,6,7,8-tetrahydroindolizine inhibiteurs d'hsp90, compositions les contenant et utilisation |
| WO2011133520A1 (en) | 2010-04-19 | 2011-10-27 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compounds and a egfr inhibitor |
| CA2853799A1 (en) | 2011-11-02 | 2013-05-10 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of hsp90 inhibitors with topoisomerase i inhibitors |
| AU2012332424A1 (en) | 2011-11-02 | 2014-06-05 | Synta Pharmaceuticals Corp. | Combination therapy of Hsp90 inhibitors with platinum-containing agents |
| WO2013074594A1 (en) | 2011-11-14 | 2013-05-23 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with braf inhibitors |
| WO2014199164A1 (en) * | 2013-06-12 | 2014-12-18 | Ampla Pharmaceuticals, Inc. | Diaryl substituted heteroaromatic compounds |
| WO2017155942A2 (en) | 2016-03-07 | 2017-09-14 | Northwestern University | Substituted heterocycles as c-myc targeting agents |
| US11142504B2 (en) | 2016-03-07 | 2021-10-12 | Northwestern University | Substituted heterocycles as c-MYC targeting agents |
| CA3073956A1 (en) * | 2017-09-03 | 2019-03-07 | Angion Biomedica Corp. | Vinylheterocycles as rho-associated coiled-coil kinase (rock) inhibitors |
| JP2022511287A (ja) * | 2018-08-31 | 2022-01-31 | ノースウェスタン ユニバーシティ | ｃ－ＭＹＣ標的剤としての置換複素環化合物 |
| CA3142351A1 (en) * | 2019-05-31 | 2020-12-03 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| WO2020257261A1 (en) | 2019-06-17 | 2020-12-24 | Northwestern University | SUBSTITUTED HETEROCYCLES AS c-MYC TARGETING AGENTS |
| TW202404957A (zh) * | 2022-06-29 | 2024-02-01 | 大陸商上海翰森生物醫藥科技有限公司 | 雜環類衍生物抑制劑、其製備方法和應用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5552426A (en) * | 1994-04-29 | 1996-09-03 | Eli Lilly And Company | Methods for treating a physiological disorder associated with β-amyloid peptide |
| AU776652B2 (en) | 1999-03-12 | 2004-09-16 | United States Of America, Represented By The Secretary, Department Of Health And Human Services, The | Method of inhibiting a chaperone protein |
| KR100850727B1 (ko) | 2000-11-02 | 2008-08-06 | 슬로안-케테링인스티튜트퍼캔서리서치 | 에이치에스피90에 결합하기 위한 소분자 조성물 |
| EP1450784A4 (en) | 2001-11-09 | 2005-02-09 | Conforma Therapeutics Corp | HSP90-INHIBITABLE ZEARALANOL COMPOUNDS AND METHOD FOR THEIR PREPARATION AND USE |
| AU2002356301A1 (en) * | 2001-12-21 | 2003-07-15 | Cancer Research Technology Ltd. | 3,4-diarylpyrazoles and their use in the therapy of cancer |
| FR2840303B1 (fr) * | 2002-05-31 | 2005-07-15 | Rhodia Chimie Sa | Procede d'arylation ou de vinylation ou d'alcylynation d'un compose nucleophile |
| TW200409759A (en) * | 2002-09-25 | 2004-06-16 | Wyeth Corp | Substituted 4-(indazol-3-yl)phenols |
| GB0228417D0 (en) * | 2002-12-05 | 2003-01-08 | Cancer Rec Tech Ltd | Pyrazole compounds |
| GB0229618D0 (en) | 2002-12-19 | 2003-01-22 | Cancer Rec Tech Ltd | Pyrazole compounds |
| WO2004110351A2 (en) | 2003-05-14 | 2004-12-23 | Anadys Pharmaceuticals, Inc. | Heterocyclic compounds for treating hepatitis c virus |
| DE102006023336A1 (de) * | 2006-05-18 | 2007-11-22 | Merck Patent Gmbh | 1,5-Diphenyl-pyrazole II |
-
2004
- 2004-08-13 DE DE102004039280A patent/DE102004039280A1/de not_active Withdrawn
-
2005
- 2005-07-14 BR BRPI0514295-4A patent/BRPI0514295A/pt not_active Application Discontinuation
- 2005-07-14 ES ES05759654T patent/ES2426189T3/es active Active
- 2005-07-14 RU RU2007108859/04A patent/RU2007108859A/ru unknown
- 2005-07-14 JP JP2007525198A patent/JP4879895B2/ja not_active Expired - Fee Related
- 2005-07-14 WO PCT/EP2005/007657 patent/WO2006018082A1/de active Application Filing
- 2005-07-14 MX MX2007001692A patent/MX2007001692A/es not_active Application Discontinuation
- 2005-07-14 EP EP05759654.6A patent/EP1776346B1/de not_active Not-in-force
- 2005-07-14 US US11/659,967 patent/US7932401B2/en not_active Expired - Fee Related
- 2005-07-14 CA CA2576531A patent/CA2576531C/en not_active Expired - Fee Related
- 2005-07-14 AU AU2005274540A patent/AU2005274540B2/en not_active Ceased
- 2005-07-14 CN CNA2005800275624A patent/CN101006061A/zh active Pending
- 2005-07-14 KR KR1020077003443A patent/KR20070040811A/ko not_active Application Discontinuation
- 2005-08-12 AR ARP050103374A patent/AR050454A1/es unknown
-
2007
- 2007-03-12 ZA ZA200702098A patent/ZA200702098B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007001692A (es) | 2007-04-12 |
| US7932401B2 (en) | 2011-04-26 |
| AU2005274540A1 (en) | 2006-02-23 |
| EP1776346B1 (de) | 2013-06-26 |
| RU2007108859A (ru) | 2008-09-20 |
| BRPI0514295A (pt) | 2008-06-10 |
| US20080085904A1 (en) | 2008-04-10 |
| AU2005274540B2 (en) | 2011-06-30 |
| ES2426189T3 (es) | 2013-10-21 |
| CN101006061A (zh) | 2007-07-25 |
| JP2008509175A (ja) | 2008-03-27 |
| DE102004039280A1 (de) | 2006-02-23 |
| CA2576531A1 (en) | 2006-02-23 |
| JP4879895B2 (ja) | 2012-02-22 |
| WO2006018082A1 (de) | 2006-02-23 |
| KR20070040811A (ko) | 2007-04-17 |
| CA2576531C (en) | 2013-04-16 |
| EP1776346A1 (de) | 2007-04-25 |
| AR050454A1 (es) | 2006-10-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200702098B (en) | 1,5-Diphenylpyrazoles | |
| CA2598017C (en) | Triazole derivatives | |
| ES2375114T3 (es) | Derivados de indazolamida. | |
| AU2006246744B2 (en) | 2-amino-4-phenylquinazoline derivates and their use as HSP90 modulators | |
| CN101743229B (zh) | 喹唑啉酰胺衍生物 | |
| US8816070B2 (en) | Triazole derivative as an HSP 90 inhibitor | |
| ES2494920T3 (es) | 3-(2-hidroxifenil)-pirazoles y su utilización como moduladores de la HSP90 | |
| CA2652393C (en) | 1,5-diphenylpyrazoles ii as hsp90 inhibitors | |
| CN101443003A (zh) | 三唑衍生物ⅱ | |
| CN101484425A (zh) | 用于治疗hsp90诱导的疾病的吲唑衍生物 | |
| SG171902A1 (en) | Quinazolinamide derivatives | |
| KR20100061817A (ko) | 1,3-디히드로이소인돌 유도체 | |
| CN101163707A (zh) | 噻吩并吡啶类化合物 | |
| AU2006278944A1 (en) | Adenine derivatives | |
| ES2548027T3 (es) | Derivados de quinazolina |