JP2020535168A5 - - Google Patents

Info

Publication number

JP2020535168A5

JP2020535168A5 JP2020517516A JP2020517516A JP2020535168A5 JP 2020535168 A5 JP2020535168 A5 JP 2020535168A5 JP 2020517516 A JP2020517516 A JP 2020517516A JP 2020517516 A JP2020517516 A JP 2020517516A JP 2020535168 A5 JP2020535168 A5 JP 2020535168A5

Authority

JP

Japan

Prior art keywords

phenyl

salt

production method

cancer

salt according

Prior art date

2018-09-26

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

Links

• Espacenet
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• 150000003839 salts Chemical class 0.000 claims description 80
• -1 1-isobutyryl piperidine-4-yl Chemical group 0.000 claims description 64
• 238000004519 manufacturing process Methods 0.000 claims description 58
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
• 239000002904 solvent Substances 0.000 claims description 34
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 32
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
• 239000000243 solution Substances 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 238000000634 powder X-ray diffraction Methods 0.000 claims description 25
• 239000002002 slurry Substances 0.000 claims description 16
• 150000001875 compounds Chemical class 0.000 claims description 14
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 10
• 239000011976 maleic acid Substances 0.000 claims description 10
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 10
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
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• 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 8
• 238000010438 heat treatment Methods 0.000 claims description 8
• 238000000034 method Methods 0.000 claims description 8
• 238000003756 stirring Methods 0.000 claims description 8
• 201000011510 cancer Diseases 0.000 claims description 6
• WVPZJYCGPGSZHW-UHFFFAOYSA-N 2,4-dioxo-3-phenyl-1-propan-2-ylpyrimidine-5-carboxamide Chemical group C(C)(C)N1C(N(C(C(=C1)C(=O)N)=O)C1=CC=CC=C1)=O WVPZJYCGPGSZHW-UHFFFAOYSA-N 0.000 claims description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
• 206010025323 Lymphomas Diseases 0.000 claims description 4
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• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
• 239000007864 aqueous solution Substances 0.000 claims description 4
• 239000000706 filtrate Substances 0.000 claims description 4
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• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
• 208000009746 Adult T-Cell Leukemia-Lymphoma Diseases 0.000 claims description 2
• 208000016683 Adult T-cell leukemia/lymphoma Diseases 0.000 claims description 2
• 208000003950 B-cell lymphoma Diseases 0.000 claims description 2
• 206010005003 Bladder cancer Diseases 0.000 claims description 2
• 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
• 206010014733 Endometrial cancer Diseases 0.000 claims description 2
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 2
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 2
• 208000017604 Hodgkin disease Diseases 0.000 claims description 2
• 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 2
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
• 206010052178 Lymphocytic lymphoma Diseases 0.000 claims description 2
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
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• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
• 206010038389 Renal cancer Diseases 0.000 claims description 2
• 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
• 208000033559 Waldenström macroglobulinemia Diseases 0.000 claims description 2
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• 208000029742 colonic neoplasm Diseases 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
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• 201000004101 esophageal cancer Diseases 0.000 claims description 2
• 208000005017 glioblastoma Diseases 0.000 claims description 2
• 201000010536 head and neck cancer Diseases 0.000 claims description 2
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
• 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 2
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• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 201000009410 rhabdomyosarcoma Diseases 0.000 claims description 2
• 239000000741 silica gel Substances 0.000 claims description 2
• 229910002027 silica gel Inorganic materials 0.000 claims description 2
• 201000000849 skin cancer Diseases 0.000 claims description 2
• 239000007787 solid Substances 0.000 claims description 2
• 201000002510 thyroid cancer Diseases 0.000 claims description 2
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
• 239000003814 drug Substances 0.000 claims 5
• 238000001816 cooling Methods 0.000 claims 1
• 210000002768 hair cell Anatomy 0.000 claims 1
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• 102000001253 Protein Kinase Human genes 0.000 description 2
• 108060006633 protein kinase Proteins 0.000 description 2
• 210000004027 cell Anatomy 0.000 description 1
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