JP2019521111A5 - - Google Patents
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- JP2019521111A5 JP2019521111A5 JP2018564345A JP2018564345A JP2019521111A5 JP 2019521111 A5 JP2019521111 A5 JP 2019521111A5 JP 2018564345 A JP2018564345 A JP 2018564345A JP 2018564345 A JP2018564345 A JP 2018564345A JP 2019521111 A5 JP2019521111 A5 JP 2019521111A5
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenoxy
- acetamide
- piperidin
- cancer
- substituted
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 21
- 239000008194 pharmaceutical composition Substances 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 13
- 125000001153 fluoro group Chemical group F* 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 10
- 241000124008 Mammalia Species 0.000 claims 9
- 208000002780 macular degeneration Diseases 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 206010064930 age-related macular degeneration Diseases 0.000 claims 7
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 5
- 230000001684 chronic effect Effects 0.000 claims 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- 208000009956 adenocarcinoma Diseases 0.000 claims 4
- 229940000425 combination drug Drugs 0.000 claims 4
- 208000005017 glioblastoma Diseases 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 208000032839 leukemia Diseases 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 210000000056 organ Anatomy 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- 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
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- -1 chloro, bromo, iodo Chemical group 0.000 claims 3
- 208000030533 eye disease Diseases 0.000 claims 3
- 125000004474 heteroalkylene group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 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
- 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
- 125000001424 substituent group Chemical group 0.000 claims 3
- SDAFDLHADBQPAW-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenoxy)acetyl]piperidin-3-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CN(CCC2)C(COC2=CC=C(C=C2)Cl)=O)C=C1 SDAFDLHADBQPAW-UHFFFAOYSA-N 0.000 claims 2
- HUAGZYGFJWLPIW-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-(4-chlorophenoxy)propanoyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)C(CCOC2=CC=C(C=C2)Cl)=O)C=C1 HUAGZYGFJWLPIW-UHFFFAOYSA-N 0.000 claims 2
- IEFPRYVHZMCMLW-UHFFFAOYSA-N 4-[[2-(4-chlorophenoxy)acetyl]amino]-1-[3-(4-chlorophenoxy)propyl]piperidine-2-carboxylic acid Chemical compound ClC1=CC=C(OCC(=O)NC2CC(N(CC2)CCCOC2=CC=C(C=C2)Cl)C(=O)O)C=C1 IEFPRYVHZMCMLW-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
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 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
- 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
- 239000005556 hormone Substances 0.000 claims 2
- 229940088597 hormone Drugs 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
- 230000037361 pathway Effects 0.000 claims 2
- 201000002510 thyroid cancer Diseases 0.000 claims 2
- CLNAHCAPVFLXMG-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)acetyl]-N-[2-(4-chlorophenyl)ethyl]piperidine-4-carboxamide Chemical compound ClC1=CC=C(CCNC(=O)C2CCN(CC2)C(COC2=CC=C(C=C2)Cl)=O)C=C1 CLNAHCAPVFLXMG-UHFFFAOYSA-N 0.000 claims 1
- RQKPXUAOOBRMNF-SEJPIABJSA-N 2-(4-chlorophenoxy)-N-[(1R,5S)-8-[3-(4-chlorophenoxy)propyl]-8-azabicyclo[3.2.1]octan-3-yl]acetamide Chemical compound Clc1ccc(OCCCN2[C@H]3CC[C@@H]2CC(C3)NC(=O)COc2ccc(Cl)cc2)cc1 RQKPXUAOOBRMNF-SEJPIABJSA-N 0.000 claims 1
- LTKPWMPNGQGTKP-NHCUHLMSSA-N 2-(4-chlorophenoxy)-N-[1-[(1R,2R)-2-(4-chlorophenoxy)cyclopropanecarbonyl]piperidin-4-yl]acetamide Chemical compound Clc1ccc(OCC(=O)NC2CCN(CC2)C(=O)[C@@H]2C[C@H]2Oc2ccc(Cl)cc2)cc1 LTKPWMPNGQGTKP-NHCUHLMSSA-N 0.000 claims 1
- PYRNCZPMBRVYQL-HTAPYJJXSA-N 2-(4-chlorophenoxy)-N-[1-[(1R,2R)-2-[(4-chlorophenyl)methyl]cyclopropanecarbonyl]piperidin-4-yl]acetamide Chemical compound Clc1ccc(C[C@H]2C[C@H]2C(=O)N2CCC(CC2)NC(=O)COc2ccc(Cl)cc2)cc1 PYRNCZPMBRVYQL-HTAPYJJXSA-N 0.000 claims 1
- LTKPWMPNGQGTKP-RTWAWAEBSA-N 2-(4-chlorophenoxy)-N-[1-[(1R,2S)-2-(4-chlorophenoxy)cyclopropanecarbonyl]piperidin-4-yl]acetamide Chemical compound Clc1ccc(OCC(=O)NC2CCN(CC2)C(=O)[C@@H]2C[C@@H]2Oc2ccc(Cl)cc2)cc1 LTKPWMPNGQGTKP-RTWAWAEBSA-N 0.000 claims 1
- PYRNCZPMBRVYQL-JTSKRJEESA-N 2-(4-chlorophenoxy)-N-[1-[(1S,2R)-2-[(4-chlorophenyl)methyl]cyclopropanecarbonyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(C[C@@H]2[C@H](C2)C(=O)N2CCC(CC2)NC(COC2=CC=C(C=C2)Cl)=O)C=C1 PYRNCZPMBRVYQL-JTSKRJEESA-N 0.000 claims 1
- RXLGTJKEZRYHDT-LJQANCHMSA-N 2-(4-chlorophenoxy)-N-[1-[(2R)-3-(4-chlorophenoxy)-2-hydroxypropyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)C[C@H](COC2=CC=C(C=C2)Cl)O)C=C1 RXLGTJKEZRYHDT-LJQANCHMSA-N 0.000 claims 1
- RXLGTJKEZRYHDT-IBGZPJMESA-N 2-(4-chlorophenoxy)-N-[1-[(2S)-3-(4-chlorophenoxy)-2-hydroxypropyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)C[C@@H](COC2=CC=C(C=C2)Cl)O)C=C1 RXLGTJKEZRYHDT-IBGZPJMESA-N 0.000 claims 1
- ICRMSNZUVYLWPJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(3,4-dichlorophenoxy)ethyl]-3-fluoropiperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2C(CN(CC2)CCOC2=CC(=C(C=C2)Cl)Cl)F)C=C1 ICRMSNZUVYLWPJ-UHFFFAOYSA-N 0.000 claims 1
- SXOVROMRPMIVNU-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenoxy)acetyl]-3-fluoropiperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2C(CN(CC2)C(COC2=CC=C(C=C2)Cl)=O)F)C=C1 SXOVROMRPMIVNU-UHFFFAOYSA-N 0.000 claims 1
- IPZNJYJIAZIITG-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenoxy)acetyl]-3-methylpiperidin-4-yl]acetamide Chemical compound CC1CN(CCC1NC(=O)COc1ccc(Cl)cc1)C(=O)COc1ccc(Cl)cc1 IPZNJYJIAZIITG-UHFFFAOYSA-N 0.000 claims 1
- NZFYVDSLZDHEAB-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenoxy)acetyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)C(COC2=CC=C(C=C2)Cl)=O)C=C1 NZFYVDSLZDHEAB-UHFFFAOYSA-N 0.000 claims 1
- KCRGFNUBHMUFNZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenoxy)ethyl]-3-fluoropiperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2C(CN(CC2)CCOC2=CC=C(C=C2)Cl)F)C=C1 KCRGFNUBHMUFNZ-UHFFFAOYSA-N 0.000 claims 1
- FBWNZQIMXQRATR-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenoxy)ethyl]-3-hydroxypiperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2C(CN(CC2)CCOC2=CC=C(C=C2)Cl)O)C=C1 FBWNZQIMXQRATR-UHFFFAOYSA-N 0.000 claims 1
- UAJNIHNUERTJJJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenoxy)ethyl]-3-methylpiperidin-4-yl]acetamide Chemical compound CC1CN(CCOc2ccc(Cl)cc2)CCC1NC(=O)COc1ccc(Cl)cc1 UAJNIHNUERTJJJ-UHFFFAOYSA-N 0.000 claims 1
- CVIUEZUCLHVQFN-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-(4-chlorophenyl)cyclopropanecarbonyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)C(=O)C2C(C2)C2=CC=C(C=C2)Cl)C=C1 CVIUEZUCLHVQFN-UHFFFAOYSA-N 0.000 claims 1
- TWPTUJLPTQIUHG-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[2-[(5-chloro-1,2-thiazol-3-yl)oxy]ethyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC(=NS1)OCCN1CCC(CC1)NC(COC1=CC=C(C=C1)Cl)=O TWPTUJLPTQIUHG-UHFFFAOYSA-N 0.000 claims 1
- CUVFHRREYFDAJM-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-(3,4-dichlorophenoxy)propyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)CCCOC2=CC(=C(C=C2)Cl)Cl)C=C1 CUVFHRREYFDAJM-UHFFFAOYSA-N 0.000 claims 1
- FWYAKPGRSZBDDO-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-(4-chlorophenoxy)-2-fluoropropyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)CC(COC2=CC=C(C=C2)Cl)F)C=C1 FWYAKPGRSZBDDO-UHFFFAOYSA-N 0.000 claims 1
- RXLGTJKEZRYHDT-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-(4-chlorophenoxy)-2-hydroxypropyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)CC(COC2=CC=C(C=C2)Cl)O)C=C1 RXLGTJKEZRYHDT-UHFFFAOYSA-N 0.000 claims 1
- PTQVOFDUNFRWQS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-(4-chlorophenoxy)-2-methoxypropyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)CC(COC2=CC=C(C=C2)Cl)OC)C=C1 PTQVOFDUNFRWQS-UHFFFAOYSA-N 0.000 claims 1
- WKDWVZMPHCVMQO-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-(4-chlorophenoxy)propyl]-2-oxopiperidin-4-yl]acetamide Chemical compound Clc1ccc(OCCCN2CCC(CC2=O)NC(=O)COc2ccc(Cl)cc2)cc1 WKDWVZMPHCVMQO-UHFFFAOYSA-N 0.000 claims 1
- VUWKMCVNOMZWBB-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-(4-chlorophenoxy)propyl]piperidin-4-yl]-N-methylacetamide Chemical compound ClC1=CC=C(OCC(=O)N(C)C2CCN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1 VUWKMCVNOMZWBB-UHFFFAOYSA-N 0.000 claims 1
- NCAZTXKTUWOOJG-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-(4-chlorophenoxy)propyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1 NCAZTXKTUWOOJG-UHFFFAOYSA-N 0.000 claims 1
- IADNPAQXHWUHTH-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-(5-chloropyridin-2-yl)oxypropyl]piperidin-4-yl]acetamide Chemical compound Clc1ccc(OCC(=O)NC2CCN(CCCOc3ccc(Cl)cn3)CC2)cc1 IADNPAQXHWUHTH-UHFFFAOYSA-N 0.000 claims 1
- SRPCPZZPWPQOGO-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-(6-chloropyridin-3-yl)oxypropyl]piperidin-4-yl]acetamide Chemical compound Clc1ccc(OCC(=O)NC2CCN(CCCOc3ccc(Cl)nc3)CC2)cc1 SRPCPZZPWPQOGO-UHFFFAOYSA-N 0.000 claims 1
- RRPHUGRQHSANRS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[3-[(5-chloro-1,2-thiazol-3-yl)oxy]propyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC(=NS1)OCCCN1CCC(CC1)NC(COC1=CC=C(C=C1)Cl)=O RRPHUGRQHSANRS-UHFFFAOYSA-N 0.000 claims 1
- RQTIPCTVVLRVMM-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[4-(4-chlorophenyl)butanoyl]-3-fluoropiperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2C(CN(CC2)C(CCCC2=CC=C(C=C2)Cl)=O)F)C=C1 RQTIPCTVVLRVMM-UHFFFAOYSA-N 0.000 claims 1
- LXLVCKWJABXRDF-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[1-[4-(4-chlorophenyl)butanoyl]piperidin-4-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)C(CCCC2=CC=C(C=C2)Cl)=O)C=C1 LXLVCKWJABXRDF-UHFFFAOYSA-N 0.000 claims 1
- YHGOTMIRLUEPJH-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[2-[1-[2-(4-chlorophenoxy)acetyl]piperidin-3-yl]ethyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCCC2CN(CCC2)C(COC2=CC=C(C=C2)Cl)=O)C=C1 YHGOTMIRLUEPJH-UHFFFAOYSA-N 0.000 claims 1
- BFIZWKIJTFXDRR-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[2-[2-(4-chlorophenoxy)acetyl]-2-azabicyclo[2.2.1]heptan-5-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2C3CN(C(C2)C3)C(COC2=CC=C(C=C2)Cl)=O)C=C1 BFIZWKIJTFXDRR-UHFFFAOYSA-N 0.000 claims 1
- YBCDJKCLFFCWRJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[2-[3-(4-chlorophenoxy)-2-hydroxypropyl]-2-azabicyclo[2.2.1]heptan-5-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2C3CN(C(C2)C3)CC(COC2=CC=C(C=C2)Cl)O)C=C1 YBCDJKCLFFCWRJ-UHFFFAOYSA-N 0.000 claims 1
- JOAQZBRSUYTBKU-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[2-[3-(4-chlorophenoxy)propyl]-2-azabicyclo[2.2.1]heptan-5-yl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NC2C3CN(C(C2)C3)CCCOC2=CC=C(C=C2)Cl)C=C1 JOAQZBRSUYTBKU-UHFFFAOYSA-N 0.000 claims 1
- YORRSFUJEUOIAW-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[2-(4-chlorophenoxy)acetyl]piperidin-4-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CCN(CC2)C(COC2=CC=C(C=C2)Cl)=O)C=C1 YORRSFUJEUOIAW-UHFFFAOYSA-N 0.000 claims 1
- AYUPSTWRQYVNSF-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-[[1-[3-(4-chlorophenoxy)propyl]piperidin-4-yl]methyl]acetamide Chemical compound ClC1=CC=C(OCC(=O)NCC2CCN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1 AYUPSTWRQYVNSF-UHFFFAOYSA-N 0.000 claims 1
- CUUAMCCAKPMQPY-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl]acetamide Chemical compound C1=CC(Cl)=CC=C1OCCN1CCC(NC(=O)COC=2C=CC(Cl)=CC=2)CC1 CUUAMCCAKPMQPY-UHFFFAOYSA-N 0.000 claims 1
- JGMKZRVBSKAODJ-UHFFFAOYSA-N 2-[4-[[2-(4-chlorophenoxy)acetyl]amino]piperidin-1-yl]-4-(3,4-dichlorophenoxy)butanoic acid Chemical compound ClC1=CC=C(OCC(=O)NC2CCN(CC2)C(C(=O)O)CCOC2=CC(=C(C=C2)Cl)Cl)C=C1 JGMKZRVBSKAODJ-UHFFFAOYSA-N 0.000 claims 1
- BWECGZMXFKNDRC-UHFFFAOYSA-N 4-(4-chlorophenoxy)-2-[4-[[2-(3,4-dichlorophenoxy)acetyl]amino]piperidin-1-yl]butanoic acid Chemical compound ClC1=CC=C(OCCC(C(=O)O)N2CCC(CC2)NC(COC2=CC(=C(C=C2)Cl)Cl)=O)C=C1 BWECGZMXFKNDRC-UHFFFAOYSA-N 0.000 claims 1
- MUQWCCOAJINMHS-UHFFFAOYSA-N 4-(4-chlorophenoxy)-2-[4-[[2-(4-chlorophenoxy)acetyl]amino]piperidin-1-yl]butanoic acid Chemical compound ClC1=CC=C(OCCC(C(=O)O)N2CCC(CC2)NC(COC2=CC=C(C=C2)Cl)=O)C=C1 MUQWCCOAJINMHS-UHFFFAOYSA-N 0.000 claims 1
- KGIPMZXCKRJPQM-UHFFFAOYSA-N 4-[2-[(4-chlorophenoxy)methyl]imidazol-1-yl]-1-[3-(4-chlorophenoxy)propyl]piperidine Chemical compound ClC1=CC=C(OCC=2N(C=CN=2)C2CCN(CC2)CCCOC2=CC=C(C=C2)Cl)C=C1 KGIPMZXCKRJPQM-UHFFFAOYSA-N 0.000 claims 1
- QFDSCLWIILASNT-UHFFFAOYSA-N 6-chloro-N-[1-[3-(4-chlorophenoxy)propyl]piperidin-4-yl]-3,4-dihydro-2H-chromene-2-carboxamide Chemical compound ClC=1C=C2CCC(OC2=CC=1)C(=O)NC1CCN(CC1)CCCOC1=CC=C(C=C1)Cl QFDSCLWIILASNT-UHFFFAOYSA-N 0.000 claims 1
- OOWVALZPXYWWRL-UHFFFAOYSA-N 8-[2-(4-chlorophenoxy)acetyl]-3-[2-(4-chlorophenoxy)ethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound ClC1=CC=C(OCC(=O)N2CCC3(CN(C(O3)=O)CCOC3=CC=C(C=C3)Cl)CC2)C=C1 OOWVALZPXYWWRL-UHFFFAOYSA-N 0.000 claims 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000032467 Aplastic anaemia Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000014644 Brain disease Diseases 0.000 claims 1
- 208000011691 Burkitt lymphomas Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010008263 Cervical dysplasia Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000005590 Choroidal Neovascularization Diseases 0.000 claims 1
- 206010060823 Choroidal neovascularisation Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 208000035984 Colonic Polyps Diseases 0.000 claims 1
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 1
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 1
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 1
- 102100023580 Cyclic AMP-dependent transcription factor ATF-4 Human genes 0.000 claims 1
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 claims 1
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000006402 Ductal Carcinoma Diseases 0.000 claims 1
- 208000019878 Eales disease Diseases 0.000 claims 1
- 208000032274 Encephalopathy Diseases 0.000 claims 1
- 206010014733 Endometrial cancer Diseases 0.000 claims 1
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 1
- 206010014967 Ependymoma Diseases 0.000 claims 1
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-
2017
- 2017-06-07 CA CA3026982A patent/CA3026982A1/en active Pending
- 2017-06-07 KR KR1020197000186A patent/KR20190015748A/ko not_active Withdrawn
- 2017-06-07 WO PCT/IB2017/053372 patent/WO2017212425A1/en not_active Ceased
- 2017-06-07 JP JP2018564345A patent/JP2019521111A/ja active Pending
- 2017-06-07 CN CN201780048778.1A patent/CN109563071B/zh active Active
- 2017-06-07 EP EP17733530.4A patent/EP3468960B1/en active Active
- 2017-06-07 AU AU2017279029A patent/AU2017279029A1/en not_active Abandoned
- 2017-06-07 ES ES17733530T patent/ES2913929T3/es active Active
- 2017-06-07 US US16/307,507 patent/US20190298705A1/en not_active Abandoned
- 2017-06-07 RU RU2018145734A patent/RU2018145734A/ru not_active Application Discontinuation
- 2017-06-07 BR BR112018075598-2A patent/BR112018075598A2/pt not_active IP Right Cessation
-
2020
- 2020-06-11 US US16/898,667 patent/US11547704B2/en active Active
-
2022
- 2022-12-06 US US18/075,664 patent/US20230165848A1/en not_active Abandoned
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