JP2020507618A5 - - Google Patents
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- JP2020507618A5 JP2020507618A5 JP2019545281A JP2019545281A JP2020507618A5 JP 2020507618 A5 JP2020507618 A5 JP 2020507618A5 JP 2019545281 A JP2019545281 A JP 2019545281A JP 2019545281 A JP2019545281 A JP 2019545281A JP 2020507618 A5 JP2020507618 A5 JP 2020507618A5
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- JP
- Japan
- Prior art keywords
- formula
- crystalline
- powder
- ray diffraction
- further characterized
- 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.)
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- 238000000634 powder X-ray diffraction Methods 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 13
- 239000003960 organic solvent Substances 0.000 claims 12
- 239000002585 base Substances 0.000 claims 9
- 238000000113 differential scanning calorimetry Methods 0.000 claims 9
- 238000002411 thermogravimetry Methods 0.000 claims 9
- 238000001757 thermogravimetry curve Methods 0.000 claims 9
- 230000004580 weight loss Effects 0.000 claims 9
- 238000000034 method Methods 0.000 claims 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- -1 tosylate ion Chemical class 0.000 claims 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 238000001179 sorption measurement Methods 0.000 claims 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000002140 halogenating effect Effects 0.000 claims 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 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 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229940006460 bromide ion Drugs 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- 150000004692 metal hydroxides Chemical class 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical group CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 150000003459 sulfonic acid esters Chemical class 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- KPSLMMMHDPNHFH-UHFFFAOYSA-N Cc1c(CCCO)c(C)n[nH]1 Chemical compound Cc1c(CCCO)c(C)n[nH]1 KPSLMMMHDPNHFH-UHFFFAOYSA-N 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022162530A JP2022183220A (ja) | 2017-02-17 | 2022-10-07 | Ａｇ－１０、その中間体及びその塩の調製方法 |
| JP2024178238A JP2024177569A (ja) | 2017-02-17 | 2024-10-10 | Ａｇ－１０、その中間体及びその塩の調製方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762460576P | 2017-02-17 | 2017-02-17 | |
| US62/460,576 | 2017-02-17 | ||
| PCT/US2018/000025 WO2018151815A1 (en) | 2017-02-17 | 2018-02-16 | Processes for preparing ag-10, its intermediates, and salts thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022162530A Division JP2022183220A (ja) | 2017-02-17 | 2022-10-07 | Ａｇ－１０、その中間体及びその塩の調製方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020507618A JP2020507618A (ja) | 2020-03-12 |
| JP2020507618A5 true JP2020507618A5 (https=) | 2021-03-25 |
| JP7157752B2 JP7157752B2 (ja) | 2022-10-20 |
Family
ID=63166944
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019545281A Active JP7157752B2 (ja) | 2017-02-17 | 2018-02-16 | Ａｇ－１０、その中間体及びその塩の調製方法 |
| JP2022162530A Pending JP2022183220A (ja) | 2017-02-17 | 2022-10-07 | Ａｇ－１０、その中間体及びその塩の調製方法 |
| JP2024178238A Pending JP2024177569A (ja) | 2017-02-17 | 2024-10-10 | Ａｇ－１０、その中間体及びその塩の調製方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022162530A Pending JP2022183220A (ja) | 2017-02-17 | 2022-10-07 | Ａｇ－１０、その中間体及びその塩の調製方法 |
| JP2024178238A Pending JP2024177569A (ja) | 2017-02-17 | 2024-10-10 | Ａｇ－１０、その中間体及びその塩の調製方法 |
Country Status (17)
| Country | Link |
|---|---|
| US (5) | US10513497B2 (https=) |
| EP (1) | EP3582773A4 (https=) |
| JP (3) | JP7157752B2 (https=) |
| KR (3) | KR102874295B1 (https=) |
| CN (3) | CN116730920A (https=) |
| AU (2) | AU2018222739C1 (https=) |
| CA (1) | CA3051357A1 (https=) |
| CL (1) | CL2019002321A1 (https=) |
| EA (1) | EA201991921A1 (https=) |
| IL (3) | IL298196A (https=) |
| MA (1) | MA47511A (https=) |
| MX (3) | MX2021015220A (https=) |
| NZ (2) | NZ797275A (https=) |
| SG (1) | SG11201906922TA (https=) |
| TW (3) | TW202515849A (https=) |
| WO (1) | WO2018151815A1 (https=) |
| ZA (1) | ZA202407964B (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102874295B1 (ko) | 2017-02-17 | 2025-10-20 | 에이도스 테라퓨틱스, 인코포레이티드 | Ag-10, 이의 중간체, 및 이의 염을 제조하는 방법 |
| US11058668B2 (en) * | 2018-03-23 | 2021-07-13 | Eidos Therapeutics, Inc. | Methods of treating TTR amyloidosis using AG10 |
| IL325404A (en) | 2018-08-17 | 2026-02-01 | Eidos Therapeutics Inc | Spice formulations containing 3-(3-(5,3-dimethyl-1h-pyrazol-4-yl)propoxy)-4-fluorobenzoic acid |
| WO2020128816A2 (en) | 2018-12-20 | 2020-06-25 | Pfizer Inc. | Pharmaceutical compositions and methods comprising a combination of a benzoxazole transthyretin stabilizer and an additional therapeutic agent |
| WO2022112919A1 (en) | 2020-11-25 | 2022-06-02 | Pfizer Inc. | (aza)benzothiazolyl substituted pyrazole compounds |
| WO2023009612A1 (en) | 2021-07-28 | 2023-02-02 | Protego Biopharma, Inc. | Acoramidis (3-(3-(3,5-dimethyl-1h-pyrazol-4-yl)propoxy)-4-fluorobenzoic acid) derivatives for stabilizing transthyretin (tts) and inhibiting tts misfolding for the treatment of e.g. peripheral ttr amyloidosis |
| WO2023052652A1 (en) | 2021-10-01 | 2023-04-06 | Sandoz Ag | Crystalline form of acoramidis hydrochloride |
| WO2025220043A1 (en) * | 2024-04-18 | 2025-10-23 | Dr. Reddy's Laboratories Limited | Solid state forms of acoramidis and process for their preparation |
| WO2026050334A1 (en) | 2024-08-29 | 2026-03-05 | Alexion Pharmaceuticals, Inc. | Transthyretin stabilizers and methods of use thereof |
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