TW202116752A

TW202116752A - 吡唑衍生物之鹽及吡唑衍生物之製劑

吡唑衍生物之鹽及吡唑衍生物之製劑 Download PDF

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Publication number: TW202116752A
Authority: TW; Taiwan
Prior art keywords: salt; preparation; phenyl; group; alkyl
Prior art date: 2019-07-08

Application number

TW109123069A

Other languages

English (en)

Chinese (zh)

Inventor

杉本八郎

奥田充顕

中野眞人

髙見真子

Original Assignee

日商綠色科技股份有限公司

Priority date

2019-07-08

Filing date

2020-07-08

Publication date

2021-05-01

2020-07-08 Application filed by 日商綠色科技股份有限公司 filed Critical 日商綠色科技股份有限公司

2021-05-01 Publication of TW202116752A publication Critical patent/TW202116752A/zh

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238000002360 preparation method Methods 0.000 title claims abstract description 136
150000003839 salts Chemical class 0.000 title claims abstract description 99
150000003217 pyrazoles Chemical class 0.000 title claims abstract description 24
-1 alkyl sulfate ester salt Chemical class 0.000 claims abstract description 468
239000007962 solid dispersion Substances 0.000 claims abstract description 58
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 44
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 26
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
125000001424 substituent group Chemical group 0.000 claims description 110
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 78
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
150000008052 alkyl sulfonates Chemical class 0.000 claims description 42
239000000243 solution Substances 0.000 claims description 41
229920002554 vinyl polymer Polymers 0.000 claims description 37
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims description 35
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 32
239000000126 substance Substances 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 24
238000002844 melting Methods 0.000 claims description 24
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238000001694 spray drying Methods 0.000 claims description 24
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
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LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 13
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HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical class CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 claims description 12
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102000013498 tau Proteins Human genes 0.000 claims description 9
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DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 5
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AMBZHNVCLPHAKA-NSJFVGFPSA-N 6-[(e)-2-[5-[(e)-2-[2-methoxy-4-(pyridin-2-ylmethoxy)phenyl]ethenyl]-1h-pyrazol-3-yl]ethenyl]-1h-indole Chemical compound C=1C=C(\C=C\C=2NN=C(\C=C\C=3C=C4NC=CC4=CC=3)C=2)C(OC)=CC=1OCC1=CC=CC=N1 AMBZHNVCLPHAKA-NSJFVGFPSA-N 0.000 claims description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
150000001413 amino acids Chemical class 0.000 claims description 3
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206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
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230000000694 effects Effects 0.000 description 13
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RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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238000007922 dissolution test Methods 0.000 description 10
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ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 10
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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150000001412 amines Chemical class 0.000 description 6
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