JP2019521109A5 - - Google Patents
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- JP2019521109A5 JP2019521109A5 JP2018564292A JP2018564292A JP2019521109A5 JP 2019521109 A5 JP2019521109 A5 JP 2019521109A5 JP 2018564292 A JP2018564292 A JP 2018564292A JP 2018564292 A JP2018564292 A JP 2018564292A JP 2019521109 A5 JP2019521109 A5 JP 2019521109A5
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenoxy
- acetamide
- methyl
- pyrrolidin
- cancer
- 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.)
- Pending
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- 125000001153 fluoro group Chemical group F* 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 22
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 20
- 239000008194 pharmaceutical composition Substances 0.000 claims 17
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 10
- 241000124008 Mammalia Species 0.000 claims 9
- 208000002780 macular degeneration Diseases 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims 8
- 206010064930 age-related macular degeneration Diseases 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 5
- 230000001684 chronic effect Effects 0.000 claims 5
- 208000009956 adenocarcinoma Diseases 0.000 claims 4
- -1 chloro, bromo, iodo Chemical group 0.000 claims 4
- 229940000425 combination drug Drugs 0.000 claims 4
- 208000005017 glioblastoma Diseases 0.000 claims 4
- 208000032839 leukemia Diseases 0.000 claims 4
- 210000000056 organ Anatomy 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- AFYGYUNVBUNUMP-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(6-chloropyridin-3-yl)oxyacetyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)C(COC=2C=NC(=CC=2)Cl)=O)C=C1 AFYGYUNVBUNUMP-UHFFFAOYSA-N 0.000 claims 3
- 208000030090 Acute Disease Diseases 0.000 claims 3
- 206010068873 Adenosquamous cell carcinoma Diseases 0.000 claims 3
- 208000017667 Chronic Disease Diseases 0.000 claims 3
- 206010018404 Glucagonoma Diseases 0.000 claims 3
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 3
- 206010038389 Renal cancer Diseases 0.000 claims 3
- 208000006336 acinar cell carcinoma Diseases 0.000 claims 3
- 201000008395 adenosquamous carcinoma Diseases 0.000 claims 3
- 229940034982 antineoplastic agent Drugs 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 208000030533 eye disease Diseases 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 206010022498 insulinoma Diseases 0.000 claims 3
- 201000010985 invasive ductal carcinoma Diseases 0.000 claims 3
- 201000010982 kidney cancer Diseases 0.000 claims 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 3
- 201000001441 melanoma Diseases 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 201000002528 pancreatic cancer Diseases 0.000 claims 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 3
- 208000021255 pancreatic insulinoma Diseases 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- YABQYIDNNXZBLP-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1 YABQYIDNNXZBLP-UHFFFAOYSA-N 0.000 claims 2
- 206010003571 Astrocytoma Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000012609 Cowden disease Diseases 0.000 claims 2
- 201000002847 Cowden syndrome Diseases 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 208000032612 Glial tumor Diseases 0.000 claims 2
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims 2
- 206010018338 Glioma Diseases 0.000 claims 2
- 206010020631 Hypergammaglobulinaemia benign monoclonal Diseases 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 2
- 201000010536 head and neck cancer Diseases 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 125000004474 heteroalkylene group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 239000005556 hormone Substances 0.000 claims 2
- 229940088597 hormone Drugs 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 201000005328 monoclonal gammopathy of uncertain significance Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 230000037361 pathway Effects 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 201000002510 thyroid cancer Diseases 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- DTOOBYVMEKEJOW-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC=C(C=C2)Cl)C=CC(=C1)F DTOOBYVMEKEJOW-UHFFFAOYSA-N 0.000 claims 1
- PVXZAVFISRNWJY-UHFFFAOYSA-N 2-(4-chloro-3-fluorophenoxy)-N-[[1-[2-(4-chlorophenoxy)acetyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound Fc1cc(OCC(=O)NCC2CCN(C2)C(=O)COc2ccc(Cl)cc2)ccc1Cl PVXZAVFISRNWJY-UHFFFAOYSA-N 0.000 claims 1
- AOKIYDJGQNOMQN-UHFFFAOYSA-N 2-(4-chloro-3-fluorophenoxy)-N-[[1-[3-(4-chloro-3-fluorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=C(C=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC(=C(C=C2)Cl)F)C=C1)F AOKIYDJGQNOMQN-UHFFFAOYSA-N 0.000 claims 1
- YYYSGWZVPDPIQL-UHFFFAOYSA-N 2-(4-chloro-3-fluorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=C(C=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1)F YYYSGWZVPDPIQL-UHFFFAOYSA-N 0.000 claims 1
- BUYDDANXXSXDKU-UHFFFAOYSA-N 2-(4-chloro-3-methylphenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=C(C=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1)C BUYDDANXXSXDKU-UHFFFAOYSA-N 0.000 claims 1
- FLXOOBPIISWSLO-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[2-[2-(4-chlorophenoxy)acetyl]-2,7-diazaspiro[4.4]nonan-7-yl]ethanone Chemical compound C1N(CCC11CN(CC1)C(COC1=CC=C(C=C1)Cl)=O)C(COC1=CC=C(C=C1)Cl)=O FLXOOBPIISWSLO-UHFFFAOYSA-N 0.000 claims 1
- LPJDUXJIABXGGI-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[3-[[2-(4-chlorophenoxy)ethylamino]methyl]pyrrolidin-1-yl]ethanone Chemical compound ClC1=CC=C(OCC(=O)N2CC(CC2)CNCCOC2=CC=C(C=C2)Cl)C=C1 LPJDUXJIABXGGI-UHFFFAOYSA-N 0.000 claims 1
- MYNDWAZXXRDFHT-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[5-[2-(4-chlorophenoxy)acetyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl]ethanone Chemical compound Clc1ccc(OCC(=O)N2CC3CN(CC3C2)C(=O)COc2ccc(Cl)cc2)cc1 MYNDWAZXXRDFHT-UHFFFAOYSA-N 0.000 claims 1
- IQDLXEJFEJRGIX-CSXXPUDCSA-N 2-(4-chlorophenoxy)-N-[(1S,5R)-3-[2-(4-chlorophenoxy)acetyl]-3-azabicyclo[3.2.0]heptan-6-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2[C@H]3CN(C[C@H]3C2)C(COC2=CC=C(C=C2)Cl)=O)C=C1 IQDLXEJFEJRGIX-CSXXPUDCSA-N 0.000 claims 1
- DDLOSEMFQHOHSQ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenoxy)acetyl]pyrrolidin-3-yl]acetamide Chemical compound Clc1ccc(OCC(=O)NC2CCN(C2)C(=O)COc2ccc(Cl)cc2)cc1 DDLOSEMFQHOHSQ-UHFFFAOYSA-N 0.000 claims 1
- JJFMAWBYNVPZFE-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenoxy)acetyl]pyrrolidin-3-yl]oxyacetamide Chemical compound ClC1=CC=C(OCC(=O)NOC2CN(CC2)C(COC2=CC=C(C=C2)Cl)=O)C=C1 JJFMAWBYNVPZFE-UHFFFAOYSA-N 0.000 claims 1
- RDMWEWGUUKHYQF-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenyl)cyclopropanecarbonyl]pyrrolidin-3-yl]oxyacetamide Chemical compound ClC1=CC=C(OCC(=O)NOC2CN(CC2)C(=O)C2C(C2)C2=CC=C(C=C2)Cl)C=C1 RDMWEWGUUKHYQF-UHFFFAOYSA-N 0.000 claims 1
- KCCOFXZASKSAJV-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-(4-chlorophenoxy)propanoyl]pyrrolidin-3-yl]oxyacetamide Chemical compound ClC1=CC=C(OCC(=O)NOC2CN(CC2)C(CCOC2=CC=C(C=C2)Cl)=O)C=C1 KCCOFXZASKSAJV-UHFFFAOYSA-N 0.000 claims 1
- FDXMRZKBWRLGNS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[2-[1-[2-(4-chlorophenoxy)acetyl]pyrrolidin-3-yl]ethyl]acetamide Chemical compound Clc1ccc(OCC(=O)NCCC2CCN(C2)C(=O)COc2ccc(Cl)cc2)cc1 FDXMRZKBWRLGNS-UHFFFAOYSA-N 0.000 claims 1
- NJOTXDBUDMUVMT-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[2-[2-(4-chlorophenoxy)acetyl]-2-azaspiro[4.5]decan-8-yl]acetamide Chemical compound Clc1ccc(OCC(=O)NC2CCC3(CCN(C3)C(=O)COc3ccc(Cl)cc3)CC2)cc1 NJOTXDBUDMUVMT-UHFFFAOYSA-N 0.000 claims 1
- WECGRPLVFNVBOS-OAHLLOKOSA-N 2-(4-chlorophenoxy)-N-[[(3R)-1-[2-(4-chlorophenoxy)acetyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC[C@@H]2CN(CC2)C(COC2=CC=C(C=C2)Cl)=O)C=C1 WECGRPLVFNVBOS-OAHLLOKOSA-N 0.000 claims 1
- UAUXVMNQQOCUFA-QRWMCTBCSA-N 2-(4-chlorophenoxy)-N-[[(3R)-1-[3-(4-chlorophenoxy)propyl]-5-methylpyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC[C@@H]2CN(C(C2)C)CCCOC2=CC=C(C=C2)Cl)C=C1 UAUXVMNQQOCUFA-QRWMCTBCSA-N 0.000 claims 1
- YABQYIDNNXZBLP-QGZVFWFLSA-N 2-(4-chlorophenoxy)-N-[[(3R)-1-[3-(4-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC[C@@H]2CN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1 YABQYIDNNXZBLP-QGZVFWFLSA-N 0.000 claims 1
- WECGRPLVFNVBOS-HNNXBMFYSA-N 2-(4-chlorophenoxy)-N-[[(3S)-1-[2-(4-chlorophenoxy)acetyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC[C@H]2CN(CC2)C(COC2=CC=C(C=C2)Cl)=O)C=C1 WECGRPLVFNVBOS-HNNXBMFYSA-N 0.000 claims 1
- YABQYIDNNXZBLP-KRWDZBQOSA-N 2-(4-chlorophenoxy)-N-[[(3S)-1-[3-(4-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC[C@H]2CN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1 YABQYIDNNXZBLP-KRWDZBQOSA-N 0.000 claims 1
- IKOSSBXOSHFJDL-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)acetyl]-3-fluoropyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2(CN(CC2)C(COC2=CC=C(C=C2)Cl)=O)F)C=C1 IKOSSBXOSHFJDL-UHFFFAOYSA-N 0.000 claims 1
- HFAOETXPQBJFEJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)acetyl]-3-methylpyrrolidin-3-yl]methyl]acetamide Chemical compound CC1(CNC(=O)COc2ccc(Cl)cc2)CCN(C1)C(=O)COc1ccc(Cl)cc1 HFAOETXPQBJFEJ-UHFFFAOYSA-N 0.000 claims 1
- TVDBVWWGFKIMKH-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)acetyl]-5-methylpyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(C(C2)C)C(COC2=CC=C(C=C2)Cl)=O)C=C1 TVDBVWWGFKIMKH-UHFFFAOYSA-N 0.000 claims 1
- WECGRPLVFNVBOS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)acetyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)C(COC2=CC=C(C=C2)Cl)=O)C=C1 WECGRPLVFNVBOS-UHFFFAOYSA-N 0.000 claims 1
- KJWVSICNWIGTDS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)ethyl]-3-fluoropyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2(CN(CC2)CCOC2=CC=C(C=C2)Cl)F)C=C1 KJWVSICNWIGTDS-UHFFFAOYSA-N 0.000 claims 1
- RAJKMQRMPBKJST-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)ethyl]-3-methylpyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2(CN(CC2)CCOC2=CC=C(C=C2)Cl)C)C=C1 RAJKMQRMPBKJST-UHFFFAOYSA-N 0.000 claims 1
- KNBFPVWLBFDPKT-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)ethyl]-5-methylpyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(C(C2)C)CCOC2=CC=C(C=C2)Cl)C=C1 KNBFPVWLBFDPKT-UHFFFAOYSA-N 0.000 claims 1
- MZJJKNKFKQWUKH-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)ethyl]-5-oxopyrrolidin-3-yl]methyl]acetamide Chemical compound Clc1ccc(OCCN2CC(CNC(=O)COc3ccc(Cl)cc3)CC2=O)cc1 MZJJKNKFKQWUKH-UHFFFAOYSA-N 0.000 claims 1
- IQFZJDLJRNUJHE-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)ethyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)CCOC2=CC=C(C=C2)Cl)C=C1 IQFZJDLJRNUJHE-UHFFFAOYSA-N 0.000 claims 1
- YTXUEADHMVKIHM-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenyl)cyclopropanecarbonyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)C(=O)C2C(C2)C2=CC=C(C=C2)Cl)C=C1 YTXUEADHMVKIHM-UHFFFAOYSA-N 0.000 claims 1
- JZBQPJWHVPTWOI-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(5-chloropyridin-3-yl)oxyacetyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound Clc1ccc(OCC(=O)NCC2CCN(C2)C(=O)COc2cncc(Cl)c2)cc1 JZBQPJWHVPTWOI-UHFFFAOYSA-N 0.000 claims 1
- HGRFNMQDLWEPBE-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(6-chloropyridin-3-yl)oxyethyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound Clc1ccc(OCC(=O)NCC2CCN(CCOc3ccc(Cl)nc3)C2)cc1 HGRFNMQDLWEPBE-UHFFFAOYSA-N 0.000 claims 1
- CVYBZHDFCLWFMW-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(2,4-dichlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)CCCOC2=C(C=C(C=C2)Cl)Cl)C=C1 CVYBZHDFCLWFMW-UHFFFAOYSA-N 0.000 claims 1
- QIDGWWVXTLOKDM-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(3,4-dichlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC(=C(C=C2)Cl)Cl)C=C1 QIDGWWVXTLOKDM-UHFFFAOYSA-N 0.000 claims 1
- ZFYQMNAAPWIHMC-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(3-chlorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC(=CC=C2)Cl)C=C1 ZFYQMNAAPWIHMC-UHFFFAOYSA-N 0.000 claims 1
- KKHLYVXEZXRVLM-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)-2-hydroxypropyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)CC(COC2=CC=C(C=C2)Cl)O)C=C1 KKHLYVXEZXRVLM-UHFFFAOYSA-N 0.000 claims 1
- SEIBDHYNJPBSRY-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propanoyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound Clc1ccc(OCCC(=O)N2CCC(CNC(=O)COc3ccc(Cl)cc3)C2)cc1 SEIBDHYNJPBSRY-UHFFFAOYSA-N 0.000 claims 1
- BISDYPUAIKBWDZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]-2-oxopyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2C(N(CC2)CCCOC2=CC=C(C=C2)Cl)=O)C=C1 BISDYPUAIKBWDZ-UHFFFAOYSA-N 0.000 claims 1
- NUUQDTIUVLINLY-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]-3-fluoropyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2(CN(CC2)CCCOC2=CC=C(C=C2)Cl)F)C=C1 NUUQDTIUVLINLY-UHFFFAOYSA-N 0.000 claims 1
- VDBIMXSTBYWFCL-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]-3-hydroxypyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2(CN(CC2)CCCOC2=CC=C(C=C2)Cl)O)C=C1 VDBIMXSTBYWFCL-UHFFFAOYSA-N 0.000 claims 1
- ZELOVWZLSPATIT-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]-4-hydroxypyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2O)CCCOC2=CC=C(C=C2)Cl)C=C1 ZELOVWZLSPATIT-UHFFFAOYSA-N 0.000 claims 1
- KBRBPHDEHHLPFZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]-5-oxopyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(C(C2)=O)CCCOC2=CC=C(C=C2)Cl)C=C1 KBRBPHDEHHLPFZ-UHFFFAOYSA-N 0.000 claims 1
- FGBBNTJNNYCNLD-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-fluorophenoxy)propyl]pyrrolidin-3-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CN(CC2)CCCOC2=CC=C(C=C2)F)C=C1 FGBBNTJNNYCNLD-UHFFFAOYSA-N 0.000 claims 1
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| CN120097859A (zh) * | 2019-02-19 | 2025-06-06 | 加利福尼亚大学董事会 | Nurr1受体调节剂 |
| CA3130511A1 (en) * | 2019-02-25 | 2020-09-03 | Praxis Biotech LLC | Inhibitors of integrated stress response pathway |
| EP3959198A1 (en) * | 2019-04-23 | 2022-03-02 | Evotec International GmbH | Modulators of the integrated stress response pathway |
| MX2021012904A (es) | 2019-04-23 | 2022-01-18 | Evotec Int Gmbh | Moduladores de la via de respuesta al estres integrada. |
| WO2020252207A1 (en) | 2019-06-12 | 2020-12-17 | Praxis Biotech LLC | Modulators of integrated stress response pathway |
| JP7699595B2 (ja) | 2020-01-28 | 2025-06-27 | エヴォテック・インターナショナル・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 統合的ストレス応答経路の調節因子 |
| CN115190813B (zh) | 2020-03-11 | 2024-10-15 | 埃沃特克国际有限责任公司 | 整合应激反应途径的调节剂 |
| EP4232447A1 (en) | 2020-10-22 | 2023-08-30 | Evotec International GmbH | Modulators of the integrated stress response pathway |
| RS66455B1 (sr) | 2020-10-22 | 2025-02-28 | Evotec Int Gmbh | Modulatori puta integrisanog odgovora na stres |
| EP4232153A1 (en) | 2020-10-22 | 2023-08-30 | Evotec International GmbH | Modulators of the integrated stress response pathway |
| CN117062817A (zh) * | 2021-01-13 | 2023-11-14 | 斯瑞福治疗股份有限公司 | 用于抑制sgk-1的吡唑并[3,4-d]嘧啶-6-基-磺酰胺衍生物 |
| CN116332818B (zh) * | 2021-12-22 | 2023-12-15 | 王喆明 | 四氢吡咯衍生物及其应用 |
| CN116789888B (zh) * | 2023-05-04 | 2025-11-18 | 浙江大学 | 一种能够减轻器官缺血再灌注损伤的抗自由基聚合物及其制备方法和用途 |
| CN116751147A (zh) * | 2023-06-28 | 2023-09-15 | 深圳市茵诺圣生物科技有限公司 | 一种5-氨甲基-2-吡咯烷酮的合成方法 |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI95572C (fi) | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| DE60023878T2 (de) * | 1999-05-18 | 2006-07-20 | Teijin Ltd. | Heilmittel und vorbeugung für mit chemokinen verbundenen erkrankungen |
| IL148079A0 (en) | 1999-08-24 | 2002-09-12 | Medarex Inc | Human ctla-4 antibodies and compositions containing the same |
| US7605238B2 (en) | 1999-08-24 | 2009-10-20 | Medarex, Inc. | Human CTLA-4 antibodies and their uses |
| US6515013B2 (en) * | 2000-07-13 | 2003-02-04 | Abbott Laboratories | 1,3-disubstituted and 1,3,3-trisubstituted pyrrolidines as histamine-3 receptor ligands and their therapeutic applications |
| JP2002105073A (ja) * | 2000-09-27 | 2002-04-10 | Shionogi & Co Ltd | 新規マトリックスメタロプロテアーゼ阻害剤 |
| EP1343782B1 (en) | 2000-12-21 | 2009-05-06 | SmithKline Beecham Corporation | Pyrimidineamines as angiogenesis modulators |
| SE0100326D0 (sv) | 2001-02-02 | 2001-02-02 | Astrazeneca Ab | New compounds |
| MXPA04008796A (es) | 2002-03-13 | 2004-11-26 | Janssen Pharmaceutica Nv | Derivados de carbonilamino como novedosos inhibidores de desacetilasa de histona. |
| ES2350687T3 (es) | 2002-07-03 | 2011-01-26 | Ono Pharmaceutical Co., Ltd. | Composiciones de inmunopotenciación. |
| CN1753912B (zh) | 2002-12-23 | 2011-11-02 | 惠氏公司 | 抗pd-1抗体及其用途 |
| US7563869B2 (en) | 2003-01-23 | 2009-07-21 | Ono Pharmaceutical Co., Ltd. | Substance specific to human PD-1 |
| WO2004071449A2 (en) * | 2003-02-12 | 2004-08-26 | Bristol-Myers Squibb Company | Lactams as modulators of chemokine receptor activity |
| US7435830B2 (en) | 2004-03-03 | 2008-10-14 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
| EP1781670A1 (en) * | 2004-07-22 | 2007-05-09 | Cumbre Pharmaceuticals Inc. | Rifamycin derivatives for treating microbial infections |
| GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| RU2494107C2 (ru) | 2005-05-09 | 2013-09-27 | Оно Фармасьютикал Ко., Лтд. | Моноклональные антитела человека к белку программируемой смерти 1 (pd-1) и способы лечения рака с использованием анти-pd-1-антител самостоятельно или в комбинации с другими иммунотерапевтическими средствами |
| CN104356236B (zh) | 2005-07-01 | 2020-07-03 | E.R.施贵宝&圣斯有限责任公司 | 抗程序性死亡配体1(pd-l1)的人单克隆抗体 |
| CN101678989A (zh) * | 2007-04-20 | 2010-03-24 | 因维斯塔技术有限公司 | 具有张力控制的紧凑连续的越端退纱（oeto)轴架 |
| WO2008150231A1 (en) | 2007-06-08 | 2008-12-11 | Astrazeneca Ab | New heterocyclic compounds for treatment of respiratory, airway or inflammatory disorders |
| HRP20131167T1 (hr) | 2007-06-18 | 2014-01-03 | Merck Sharp & Dohme B.V. | Antitijela za humani receptor programirane smrti pd-1 |
| WO2009114335A2 (en) | 2008-03-12 | 2009-09-17 | Merck & Co., Inc. | Pd-1 binding proteins |
| WO2010098788A2 (en) | 2008-08-25 | 2010-09-02 | Amplimmune, Inc. | Pd-i antagonists and methods for treating infectious disease |
| KR101814408B1 (ko) | 2008-09-26 | 2018-01-04 | 다나-파버 캔서 인스티튜트 인크. | 인간 항-ｐｄ-１, ｐｄ-ｌ１, 및 ｐｄ-ｌ2 항체 및 그의 용도 |
| JP2010095453A (ja) * | 2008-10-14 | 2010-04-30 | Kaneka Corp | 光学活性１−アリール−３−ピロリジノールの製造法 |
| AU2009333580B2 (en) | 2008-12-09 | 2016-07-07 | Genentech, Inc. | Anti-PD-L1 antibodies and their use to enhance T-cell function |
| NZ628923A (en) | 2009-11-24 | 2016-02-26 | Medimmune Ltd | Targeted binding agents against b7-h1 |
| WO2011066342A2 (en) | 2009-11-24 | 2011-06-03 | Amplimmune, Inc. | Simultaneous inhibition of pd-l1/pd-l2 |
| US20110280877A1 (en) | 2010-05-11 | 2011-11-17 | Koji Tamada | Inhibition of B7-H1/CD80 interaction and uses thereof |
| US9428490B2 (en) * | 2011-07-29 | 2016-08-30 | Karyopharm Therapeutics Inc. | Nuclear transport modulators and uses thereof |
| JP6238459B2 (ja) | 2011-08-01 | 2017-11-29 | ジェネンテック， インコーポレイテッド | Ｐｄ−１軸結合アンタゴニストとｍｅｋ阻害剤を使用する癌の治療方法 |
| WO2013065712A1 (ja) * | 2011-10-31 | 2013-05-10 | 東レ株式会社 | ジアザスピロウレア誘導体及びその医薬用途 |
| CN113967253A (zh) | 2012-05-15 | 2022-01-25 | 百时美施贵宝公司 | 通过破坏pd-1/pd-l1信号传输的免疫治疗 |
| CA2886433C (en) | 2012-10-04 | 2022-01-04 | Dana-Farber Cancer Institute, Inc. | Human monoclonal anti-pd-l1 antibodies and methods of use |
| JP5799117B2 (ja) * | 2013-02-05 | 2015-10-21 | 大日本住友製薬株式会社 | ウラシル誘導体からなる医薬 |
| CA2904794C (en) | 2013-03-15 | 2021-11-23 | Peter Walter | Modulators of the eif2alpha pathway |
| US20160318856A1 (en) * | 2013-09-11 | 2016-11-03 | The Brigham And Women's Hospital, Inc. | Substituted Urea eIF2alpha Kinase Activators |
| EP3110794A1 (en) | 2014-02-27 | 2017-01-04 | Merck Patent GmbH | Heterocyclic compounds as nav channel inhibitors and uses thereof |
-
2017
- 2017-06-07 KR KR1020197000188A patent/KR20190015492A/ko not_active Withdrawn
- 2017-06-07 WO PCT/IB2017/053370 patent/WO2017212423A1/en not_active Ceased
- 2017-06-07 CA CA3026983A patent/CA3026983A1/en not_active Abandoned
- 2017-06-07 JP JP2018564292A patent/JP2019521109A/ja active Pending
- 2017-06-07 CN CN201780045519.3A patent/CN109563034A/zh active Pending
- 2017-06-07 RU RU2018146946A patent/RU2018146946A/ru not_active Application Discontinuation
- 2017-06-07 BR BR112018075615A patent/BR112018075615A2/pt not_active Application Discontinuation
- 2017-06-07 US US16/307,513 patent/US10851053B2/en not_active Expired - Fee Related
- 2017-06-07 AU AU2017279027A patent/AU2017279027A1/en not_active Abandoned
- 2017-06-07 EP EP17732235.1A patent/EP3468948A1/en not_active Withdrawn
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