JP2018519332A5 - - Google Patents
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- JP2018519332A5 JP2018519332A5 JP2017568244A JP2017568244A JP2018519332A5 JP 2018519332 A5 JP2018519332 A5 JP 2018519332A5 JP 2017568244 A JP2017568244 A JP 2017568244A JP 2017568244 A JP2017568244 A JP 2017568244A JP 2018519332 A5 JP2018519332 A5 JP 2018519332A5
- Authority
- JP
- Japan
- Prior art keywords
- benzenesulfonamide
- oxoimidazolidin
- cancer
- alkyl
- fluorophenyl
- 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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- 150000001875 compounds Chemical class 0.000 claims description 36
- 206010028980 Neoplasm Diseases 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 201000011510 cancer Diseases 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
- 125000001475 halogen functional group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 206010033128 Ovarian cancer Diseases 0.000 claims description 8
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 7
- 208000026310 Breast neoplasm Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 6
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 6
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 6
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- 201000005202 lung cancer Diseases 0.000 claims description 6
- 208000020816 lung neoplasm Diseases 0.000 claims description 6
- 201000001441 melanoma Diseases 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 201000011549 stomach cancer Diseases 0.000 claims description 6
- 201000002510 thyroid cancer Diseases 0.000 claims description 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 5
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 5
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
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- 239000000651 prodrug Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
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- 208000005017 glioblastoma Diseases 0.000 claims description 4
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- 208000014829 head and neck neoplasm Diseases 0.000 claims description 4
- 230000001146 hypoxic effect Effects 0.000 claims description 4
- 201000008129 pancreatic ductal adenocarcinoma Diseases 0.000 claims description 4
- 230000030833 cell death Effects 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 3
- MTZLLKHAIMENRQ-UHFFFAOYSA-N 4-(3-cyclohexyl-2-oxoimidazolidin-1-yl)benzenesulfonamide Chemical compound C1(CCCCC1)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O MTZLLKHAIMENRQ-UHFFFAOYSA-N 0.000 claims description 2
- NBSLWOQVDXHMGP-UHFFFAOYSA-N 4-(3-cyclopentyl-2-oxoimidazolidin-1-yl)benzenesulfonamide Chemical compound C1(CCCC1)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O NBSLWOQVDXHMGP-UHFFFAOYSA-N 0.000 claims description 2
- PSRKSQXJSCNCBR-UHFFFAOYSA-N 4-[2-oxo-3-(3,4,5-trimethoxyphenyl)imidazolidin-1-yl]benzenesulfonamide Chemical compound O=C1N(CCN1C1=CC(=C(C(=C1)OC)OC)OC)C1=CC=C(C=C1)S(=O)(=O)N PSRKSQXJSCNCBR-UHFFFAOYSA-N 0.000 claims description 2
- QVLMPIQNPKEIPZ-UHFFFAOYSA-N 4-[2-oxo-3-[4-(trifluoromethyl)phenyl]imidazolidin-1-yl]benzenesulfonamide Chemical compound O=C1N(CCN1C1=CC=C(C=C1)C(F)(F)F)C1=CC=C(C=C1)S(=O)(=O)N QVLMPIQNPKEIPZ-UHFFFAOYSA-N 0.000 claims description 2
- SGCKOJXZNTVQLM-UHFFFAOYSA-N 4-[3-(2,4-difluorophenyl)-2-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound FC1=C(C=CC(=C1)F)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O SGCKOJXZNTVQLM-UHFFFAOYSA-N 0.000 claims description 2
- RPIFFSSUFQKDGF-UHFFFAOYSA-N 4-[3-(2-fluoro-4-methoxyphenyl)-2-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound FC1=C(C=CC(=C1)OC)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O RPIFFSSUFQKDGF-UHFFFAOYSA-N 0.000 claims description 2
- PTXLRHZELJCNJM-UHFFFAOYSA-N 4-[3-(2-fluorophenyl)-2-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound FC1=C(C=CC=C1)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O PTXLRHZELJCNJM-UHFFFAOYSA-N 0.000 claims description 2
- DSJYWCCBODHQGZ-UHFFFAOYSA-N 4-[3-(3,4-difluorophenyl)-2-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound FC=1C=C(C=CC=1F)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O DSJYWCCBODHQGZ-UHFFFAOYSA-N 0.000 claims description 2
- GZTKOIAVJDBSIN-UHFFFAOYSA-N 4-[3-(3,5-difluorophenyl)-2-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound FC=1C=C(C=C(C=1)F)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O GZTKOIAVJDBSIN-UHFFFAOYSA-N 0.000 claims description 2
- OXYDLUALOWNOGG-UHFFFAOYSA-N 4-[3-(3,5-dimethylphenyl)-2-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound CC=1C=C(C=C(C=1)C)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O OXYDLUALOWNOGG-UHFFFAOYSA-N 0.000 claims description 2
- HBTDDPWUVQOBEA-UHFFFAOYSA-N 4-[3-(3-chloro-4-fluorophenyl)-2-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound ClC=1C=C(C=CC=1F)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O HBTDDPWUVQOBEA-UHFFFAOYSA-N 0.000 claims description 2
- DAFRLQUJYTXPNY-UHFFFAOYSA-N 4-[3-(3-fluorophenyl)-2-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound FC=1C=C(C=CC=1)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O DAFRLQUJYTXPNY-UHFFFAOYSA-N 0.000 claims description 2
- PVBBZQVAYSHPKC-UHFFFAOYSA-N 4-[3-(4-bromo-2-fluorophenyl)-2-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound BrC1=CC(=C(C=C1)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O)F PVBBZQVAYSHPKC-UHFFFAOYSA-N 0.000 claims description 2
- LRVMSXMESQWOFK-UHFFFAOYSA-N 4-[3-(4-butoxy-2-fluorophenyl)-2-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound C(CCC)OC1=CC(=C(C=C1)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O)F LRVMSXMESQWOFK-UHFFFAOYSA-N 0.000 claims description 2
- KYGXSNQBNXNQDC-UHFFFAOYSA-N 4-[3-(4-butoxyphenyl)-2-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound C(CCC)OC1=CC=C(C=C1)N1C(N(CC1)C1=CC=C(C=C1)S(=O)(=O)N)=O KYGXSNQBNXNQDC-UHFFFAOYSA-N 0.000 claims description 2
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| KR20210000564A (ko) | 2019-06-25 | 2021-01-05 | 공주대학교 산학협력단 | 신규 아만타딘 유도체 화합물 및 이의 용도 |
| CN111233786B (zh) * | 2020-02-04 | 2021-11-26 | 中国人民解放军军事科学院军事医学研究院 | 含五元杂环的苯磺酰胺类化合物及其制备方法和用途 |
| ES3014428T3 (en) * | 2020-06-02 | 2025-04-22 | Univ Yeditepe | 2-(3-(2-methyl-6-(p-tolyl) pyridine-3-yl) ureido) benzenesulfonamide and derivatives as inhibitor of carbonic anhydrase ix for the treatment of cancer |
| TR202014185A2 (tr) * | 2020-09-08 | 2022-03-21 | Anadolu Ueniversitesi | BAZI YENİ 4-(2-((5-(SÜBSTİTÜEAMİNO)-1,3,4-TİYADİAZOL-2-İL)TİYO)ASETİL)BENZENSÜLFONAMİD TÜREVLERİ ve SÖZ KONUSU TÜREVLERİN SENTEZİ İÇİN BİR YÖNTEM |
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