JPWO2020247345A5 - - Google Patents
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- JPWO2020247345A5 JPWO2020247345A5 JP2021571903A JP2021571903A JPWO2020247345A5 JP WO2020247345 A5 JPWO2020247345 A5 JP WO2020247345A5 JP 2021571903 A JP2021571903 A JP 2021571903A JP 2021571903 A JP2021571903 A JP 2021571903A JP WO2020247345 A5 JPWO2020247345 A5 JP WO2020247345A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- salt
- cancer
- item
- dsc thermogram
- 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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- 150000003839 salts Chemical class 0.000 claims description 164
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 36
- 238000001757 thermogravimetry curve Methods 0.000 claims description 26
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 20
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 16
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 10
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 9
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- 239000005711 Benzoic acid Substances 0.000 claims description 8
- 102000008122 Casein Kinase I Human genes 0.000 claims description 8
- 108010049812 Casein Kinase I Proteins 0.000 claims description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 8
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000001361 adipic acid Substances 0.000 claims description 8
- 235000011037 adipic acid Nutrition 0.000 claims description 8
- 235000010233 benzoic acid Nutrition 0.000 claims description 8
- 230000000155 isotopic effect Effects 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 7
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 6
- 230000002062 proliferating effect Effects 0.000 claims description 6
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 4
- 239000004310 lactic acid Substances 0.000 claims description 4
- 235000014655 lactic acid Nutrition 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- 239000001630 malic acid Substances 0.000 claims description 4
- 235000011090 malic acid Nutrition 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- 239000011975 tartaric acid Substances 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 0.000 claims description 4
- 230000004580 weight loss Effects 0.000 claims description 4
- 238000012217 deletion Methods 0.000 claims description 3
- 230000037430 deletion Effects 0.000 claims description 3
- 239000006186 oral dosage form Substances 0.000 claims description 3
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 2
- 208000032612 Glial tumor Diseases 0.000 claims description 2
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims description 2
- 206010018338 Glioma Diseases 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 2
- 206010029260 Neuroblastoma Diseases 0.000 claims description 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 206010038389 Renal cancer Diseases 0.000 claims description 2
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 claims description 2
- 206010061934 Salivary gland cancer Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 2
- 206010057644 Testis cancer 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
- 208000002495 Uterine Neoplasms Diseases 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 201000010881 cervical cancer Diseases 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 201000004101 esophageal cancer Diseases 0.000 claims description 2
- 235000011087 fumaric acid Nutrition 0.000 claims description 2
- 206010017758 gastric 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
- 239000006207 intravenous dosage form Substances 0.000 claims description 2
- 201000010982 kidney cancer Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 201000000050 myeloid neoplasm Diseases 0.000 claims description 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 2
- 201000008968 osteosarcoma Diseases 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 239000006201 parenteral dosage form Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 239000001384 succinic acid Substances 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 claims description 2
- 201000003120 testicular cancer Diseases 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 206010046766 uterine cancer Diseases 0.000 claims description 2
- CLJAHIKYBCKHTP-UHFFFAOYSA-N 1-[5-chloro-4-[5-(cyclopropylmethyl)-1-methylpyrazol-4-yl]pyrimidin-2-yl]cyclohexane-1,4-diamine Chemical compound ClC=1C(=NC(=NC=1)C1(CCC(CC1)N)N)C=1C=NN(C=1CC1CC1)C CLJAHIKYBCKHTP-UHFFFAOYSA-N 0.000 claims 4
- 208000003053 chromosome 5q deletion syndrome Diseases 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 12
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962856605P | 2019-06-03 | 2019-06-03 | |
| US62/856,605 | 2019-06-03 | ||
| PCT/US2020/035654 WO2020247345A1 (en) | 2019-06-03 | 2020-06-02 | Non-hygroscopic crystalline salts of a pyrazole compound, and pharmaceutical compositions and use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022535850A JP2022535850A (ja) | 2022-08-10 |
| JPWO2020247345A5 true JPWO2020247345A5 (https=) | 2023-06-09 |
| JP2022535850A5 JP2022535850A5 (https=) | 2023-06-09 |
Family
ID=71787173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021571903A Pending JP2022535850A (ja) | 2019-06-03 | 2020-06-02 | ピラゾール化合物の非吸湿性結晶塩、ならびにその医薬組成物および使用 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US12428399B2 (https=) |
| EP (1) | EP3976600A1 (https=) |
| JP (1) | JP2022535850A (https=) |
| KR (1) | KR20220041050A (https=) |
| CN (1) | CN114423752B (https=) |
| AU (1) | AU2020288163B2 (https=) |
| BR (1) | BR112021024330A2 (https=) |
| CA (1) | CA3142271A1 (https=) |
| IL (1) | IL288547B2 (https=) |
| MX (1) | MX2021014842A (https=) |
| SG (1) | SG11202113211PA (https=) |
| TW (1) | TWI866977B (https=) |
| WO (1) | WO2020247345A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20230047732A1 (en) * | 2020-01-13 | 2023-02-16 | Biotheryx, Inc. | Pyrazolylpyrimidines and use thereof |
| WO2022204220A1 (en) * | 2021-03-24 | 2022-09-29 | Biotheryx, Inc. | Pyrazolylpyrimidines for treating malignant solid tumor |
| US20230053307A1 (en) * | 2021-07-19 | 2023-02-16 | Buddhist Tzu Chi Medical Foundation | Method for preventing or treating skin disorders and conditions |
| WO2025199440A1 (en) * | 2024-03-21 | 2025-09-25 | Edgewood Oncology | Methods of treating liposarcoma using a pyrazole compound |
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-
2020
- 2020-06-02 IL IL288547A patent/IL288547B2/en unknown
- 2020-06-02 SG SG11202113211PA patent/SG11202113211PA/en unknown
- 2020-06-02 BR BR112021024330A patent/BR112021024330A2/pt unknown
- 2020-06-02 EP EP20746478.5A patent/EP3976600A1/en active Pending
- 2020-06-02 JP JP2021571903A patent/JP2022535850A/ja active Pending
- 2020-06-02 MX MX2021014842A patent/MX2021014842A/es unknown
- 2020-06-02 AU AU2020288163A patent/AU2020288163B2/en active Active
- 2020-06-02 TW TW109118526A patent/TWI866977B/zh active
- 2020-06-02 KR KR1020217042889A patent/KR20220041050A/ko active Pending
- 2020-06-02 US US17/596,023 patent/US12428399B2/en active Active
- 2020-06-02 WO PCT/US2020/035654 patent/WO2020247345A1/en not_active Ceased
- 2020-06-02 CN CN202080055602.0A patent/CN114423752B/zh active Active
- 2020-06-02 CA CA3142271A patent/CA3142271A1/en active Pending
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