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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| US20200270232A1 (en) * | 2019-02-25 | 2020-08-27 | Praxis Biotech LLC | Inhibitors of integrated stress response pathway |
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2017
- 2017-06-07 US US16/307,513 patent/US10851053B2/en not_active Expired - Fee Related
- 2017-06-07 CN CN201780045519.3A patent/CN109563034A/zh active Pending
- 2017-06-07 AU AU2017279027A patent/AU2017279027A1/en not_active Abandoned
- 2017-06-07 JP JP2018564292A patent/JP2019521109A/ja active Pending
- 2017-06-07 WO PCT/IB2017/053370 patent/WO2017212423A1/en not_active Ceased
- 2017-06-07 RU RU2018146946A patent/RU2018146946A/ru not_active Application Discontinuation
- 2017-06-07 CA CA3026983A patent/CA3026983A1/en not_active Abandoned
- 2017-06-07 BR BR112018075615A patent/BR112018075615A2/pt not_active Application Discontinuation
- 2017-06-07 EP EP17732235.1A patent/EP3468948A1/en not_active Withdrawn
- 2017-06-07 KR KR1020197000188A patent/KR20190015492A/ko not_active Withdrawn
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