JP7367147B2 - テルペノイドアミノアルコール誘導体を精製するための方法 - Google Patents
テルペノイドアミノアルコール誘導体を精製するための方法 Download PDFInfo
- Publication number
- JP7367147B2 JP7367147B2 JP2022129165A JP2022129165A JP7367147B2 JP 7367147 B2 JP7367147 B2 JP 7367147B2 JP 2022129165 A JP2022129165 A JP 2022129165A JP 2022129165 A JP2022129165 A JP 2022129165A JP 7367147 B2 JP7367147 B2 JP 7367147B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- formula
- terpenoid
- amino alcohol
- represented
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims description 59
- -1 terpenoid amino alcohol Chemical class 0.000 title claims description 57
- MKPMHJQMNACGDI-UHFFFAOYSA-N 1-methyl-4-prop-1-en-2-ylcyclohex-2-en-1-ol Chemical compound CC(=C)C1CCC(C)(O)C=C1 MKPMHJQMNACGDI-UHFFFAOYSA-N 0.000 claims description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 238000002425 crystallisation Methods 0.000 claims description 16
- 230000008025 crystallization Effects 0.000 claims description 16
- 239000000543 intermediate Substances 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 10
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 claims description 9
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 238000006735 epoxidation reaction Methods 0.000 claims description 5
- 229940087305 limonene Drugs 0.000 claims description 5
- 235000001510 limonene Nutrition 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000006728 Cope elimination reaction Methods 0.000 claims description 4
- 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 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 229960001270 d- tartaric acid Drugs 0.000 claims description 4
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 claims description 4
- 238000010791 quenching Methods 0.000 claims description 4
- 230000000171 quenching effect Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims description 2
- DYTUAOUIQFNOIH-UHFFFAOYSA-N 2,3-diethyl-2,3-dihydroxybutanedioic acid Chemical compound CCC(O)(C(O)=O)C(O)(CC)C(O)=O DYTUAOUIQFNOIH-UHFFFAOYSA-N 0.000 claims description 2
- NNOOMJWLTGIZKY-UHFFFAOYSA-N 2,3-ditert-butyl-2,3-dihydroxybutanedioic acid Chemical compound CC(C)(C)C(O)(C(O)=O)C(O)(C(O)=O)C(C)(C)C NNOOMJWLTGIZKY-UHFFFAOYSA-N 0.000 claims description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 229960002510 mandelic acid Drugs 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 150000001414 amino alcohols Chemical class 0.000 claims 1
- 229960004106 citric acid Drugs 0.000 claims 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims 1
- 235000010265 sodium sulphite Nutrition 0.000 claims 1
- 150000003505 terpenes Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 14
- MKPMHJQMNACGDI-VHSXEESVSA-N (1S,4R)-p-Mentha-2,8-dien-1-ol Chemical compound CC(=C)[C@@H]1CC[C@](C)(O)C=C1 MKPMHJQMNACGDI-VHSXEESVSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229940099369 (+)- limonene Drugs 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- 229910004373 HOAc Inorganic materials 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical group CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 229910020350 Na2WO4 Inorganic materials 0.000 description 1
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940124347 antiarthritic drug Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 description 1
- 229950011318 cannabidiol Drugs 0.000 description 1
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- PCXRACLQFPRCBB-ZWKOTPCHSA-N dihydrocannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)C)CCC(C)=C1 PCXRACLQFPRCBB-ZWKOTPCHSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical group C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ORQWTLCYLDRDHK-UHFFFAOYSA-N phenylselanylbenzene Chemical group C=1C=CC=CC=1[Se]C1=CC=CC=C1 ORQWTLCYLDRDHK-UHFFFAOYSA-N 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
H2O(223kg)、Na2WO4・H2O(10kg)、臭化ヘキサデシルトリメチルアンモニウム(CTAB、10.4kg)、45%NaOH(aq)(2.9kg)、H2SO4(3.2kg)、H3PO4(5.2kg)、リモネン(650kg)、及びジクロロメタン(1625kg)をタンクに混合・撹拌した後、50%H2O2(372kg)を当該反応混合物に加えた。反応完了後、クエンチングのためにNa2S2O3(82kg)及びH2O(390kg)を加えて、相分離になった。有機相を減圧下で濃縮し、下記式I及びIIで示される粗中間体を含む混合物(711kg)を、更なる精製なしで、次の工程に向けて集めた。
反応タンクに式I及びIIの粗中間体の混合物をジメチルアミン(520kg)水溶液及びMeOH(650kg)と混合した後、約50℃~60℃のタンク内温度に24時間加熱した。その後、反応混合物を濃縮し、抽出のためにトルエン(195kg)及びH2O(390kg)を加えた。別のトルエン(195kg)で水相を抽出した後、2つの有機相を合わせた。さらに、更なる反応に用いられるために、有機相の濃縮後、残留物(すなわち、式Vの粗化合物)を回収した。
実施例2に得られた残留物1(260kg)の酸化反応は、IPA(189kg)中のH2O2(293kg)でおよそ60℃で行われた。その後、反応混合物を約25℃に冷却し、Na2SO3(50kg)及びH2O(150kg)で反応をクエンチした。濾過及び蒸留により、320kgの残留物を獲得した。その後、(+)-p-メンタ-2,8-ジエン-1-オール(110kg)は、コープ脱離後に得られ、蒸留により精製された。
Claims (20)
- 式V’で表されるテルペノイドアミノアルコール誘導体を精製する方法であって、
下記式V’で表される粗テルペノイドアミノアルコール誘導体を提供する工程、
前記式V’で表される粗テルペノイドアミノアルコール誘導体の酸/塩基結晶化処理を行って、下記式V”で表される有機酸塩を得る工程、並びに
前記式V”で表される有機酸塩を、NaOHと、トルエン、シクロペンチルメチルエーテル、ジエチルエーテル、及びジメトキシエタンから選ばれる少なくとも1つの溶媒と反応して、精製した式V’で表されるテルペノイドアミノアルコール誘導体を得る工程、を含み、
式中、R、R1及びR2が、それぞれ独立して、置換又は無置換C1-C6アルキルである、方法。 - 前記酸/塩基結晶化処理は、塩基とする前記式V’で表される粗テルペノイドアミノアルコール誘導体と有機酸とを、有機溶媒又は有機/水溶液に混合することで行われる、請求項1に記載の方法。
- 前記有機酸は、L-酒石酸、D-酒石酸、酢酸、クエン酸、カンファースルホン酸、マンデル酸、(+)-ジ-tert-ブチル酒石酸、(+)-ジエチル酒石酸、メタンスルホン酸、又はそれらの組合せである、請求項3に記載の方法。
- 混合物における前記有機酸と前記塩基の比率は、1:1~1:3である、請求項3に記載の方法。
- 混合物における前記有機酸と前記塩基の比率は、1:1である、請求項5に記載の方法。
- 前記有機溶媒は、イソプロピルアルコールである、請求項3に記載の方法。
- 前記有機/水溶液は、アセトン/H2O溶液である、請求項3に記載の方法。
- 前記酸/塩基結晶化処理が、-5℃~30℃の温度で行われる、請求項1に記載の方法。
- 前記温度は、5℃~15℃の範囲である、請求項9に記載の方法。
- 前記精製した式V’で表されるテルペノイドアミノアルコール誘導体をイソプロピルアルコール又はアセトン/H2O溶液で洗浄する工程をさらに含む、請求項1に記載の方法。
- 前記酸化は、イソプロピルアルコール又はアセトン/H2O溶液に行われる、請求項12に記載の方法。
- 前記酸化は、50℃~70℃の温度で行われる、請求項12に記載の方法。
- 前記酸化をNa2SO3及びH2Oでクエンチする工程をさらに含む、請求項12に記載の方法。
- コープ脱離後、前記反応混合物を蒸留する工程をさらに含む、請求項12に記載の方法。
- 前記混合物の反応は、50℃~60℃の温度で行われる、請求項17に記載の方法。
- 前記アルコールは、メタノールである、請求項17に記載の方法。
- リモネンのエポキシ化を行って、前記混合物を提供する工程をさらに含む、請求項17に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17/467,974 | 2021-09-07 | ||
US17/467,974 US11739050B2 (en) | 2021-09-07 | 2021-09-07 | Method for purification of terpenoid amino alcohol derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2023038912A JP2023038912A (ja) | 2023-03-17 |
JP7367147B2 true JP7367147B2 (ja) | 2023-10-23 |
Family
ID=81324904
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2022129165A Active JP7367147B2 (ja) | 2021-09-07 | 2022-08-15 | テルペノイドアミノアルコール誘導体を精製するための方法 |
Country Status (4)
Country | Link |
---|---|
US (1) | US11739050B2 (ja) |
EP (1) | EP4144717A1 (ja) |
JP (1) | JP7367147B2 (ja) |
TW (1) | TWI828123B (ja) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003252836A (ja) | 2002-02-28 | 2003-09-10 | Daicel Chem Ind Ltd | 光学活性なトランス−2−アミノシクロアルカノール又はその塩の製造方法 |
JP2006524247A (ja) | 2003-04-24 | 2006-10-26 | マリンクロッド・インコーポレイテッド | (+)−p−メンタ−2,8−ジエン−1−オールの製造方法 |
JP2008169204A (ja) | 2006-12-15 | 2008-07-24 | Sumitomo Chemical Co Ltd | (1r,2r)−2−アミノ−1−シクロペンタノールの製造方法 |
CN109734554A (zh) | 2019-02-25 | 2019-05-10 | 江苏暨明医药科技有限公司 | 一种反式-薄荷基-2,8-二烯-1-醇的合成工艺 |
CN110143847A (zh) | 2019-06-06 | 2019-08-20 | 南京焕然生物科技有限公司 | 一种1s,4r-1-甲基-4-(1-甲基乙烯基)-2-环己烯-1-醇的制备方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH646933A5 (fr) | 1981-05-04 | 1984-12-28 | Firmenich & Cie | Procede pour la preparation de (+)-p-mentha-2,8-diene-1-ol. |
DE4140174A1 (de) * | 1990-12-19 | 1992-07-02 | Kali Chemie Pharma Gmbh | Alkylaminoalkylamin- und-aether-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
US5420353A (en) * | 1994-03-11 | 1995-05-30 | Merck & Co., Inc. | Regiospecific process to make cis-1-amino-2-alkanol from epoxide |
TW525075B (en) * | 2001-09-10 | 2003-03-21 | Systex Corp | Transaction system of digital merchandise and method therefor |
TW591047B (en) * | 2002-11-19 | 2004-06-11 | Chung Shan Inst Of Science | Process for preparing poly(urea-urethane) |
CN109890378A (zh) * | 2016-10-27 | 2019-06-14 | 三得利控股株式会社 | Foxo1活性阻碍用组合物 |
-
2021
- 2021-09-07 US US17/467,974 patent/US11739050B2/en active Active
-
2022
- 2022-03-31 EP EP22166124.2A patent/EP4144717A1/en active Pending
- 2022-04-25 TW TW111115642A patent/TWI828123B/zh active
- 2022-08-15 JP JP2022129165A patent/JP7367147B2/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003252836A (ja) | 2002-02-28 | 2003-09-10 | Daicel Chem Ind Ltd | 光学活性なトランス−2−アミノシクロアルカノール又はその塩の製造方法 |
JP2006524247A (ja) | 2003-04-24 | 2006-10-26 | マリンクロッド・インコーポレイテッド | (+)−p−メンタ−2,8−ジエン−1−オールの製造方法 |
JP2008169204A (ja) | 2006-12-15 | 2008-07-24 | Sumitomo Chemical Co Ltd | (1r,2r)−2−アミノ−1−シクロペンタノールの製造方法 |
CN109734554A (zh) | 2019-02-25 | 2019-05-10 | 江苏暨明医药科技有限公司 | 一种反式-薄荷基-2,8-二烯-1-醇的合成工艺 |
CN110143847A (zh) | 2019-06-06 | 2019-08-20 | 南京焕然生物科技有限公司 | 一种1s,4r-1-甲基-4-(1-甲基乙烯基)-2-环己烯-1-醇的制备方法 |
Non-Patent Citations (1)
Title |
---|
Tetrahedron Letters,2013年,Vol.54, No.1,p. 52-54 |
Also Published As
Publication number | Publication date |
---|---|
US20230103071A1 (en) | 2023-03-30 |
TWI828123B (zh) | 2024-01-01 |
EP4144717A1 (en) | 2023-03-08 |
US11739050B2 (en) | 2023-08-29 |
TW202311214A (zh) | 2023-03-16 |
JP2023038912A (ja) | 2023-03-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN113880903B (zh) | 莫那比拉韦的制备方法 | |
EP3490973B1 (en) | Polymorphic forms of belinostat and processes for preparation thereof | |
WO2021046636A1 (en) | Cannabinoid derivatives, precursors and uses | |
JP2021504418A (ja) | 2−(5−メトキシイソクロマン−1−イル)−4,5−ジヒドロ−1h−イミダゾールおよびその硫酸水素塩の製造方法 | |
JP4841129B2 (ja) | ペナム結晶の製造法 | |
US6495700B1 (en) | Process for producing phenserine and its analog | |
JP7367147B2 (ja) | テルペノイドアミノアルコール誘導体を精製するための方法 | |
ES2446365T3 (es) | Procedimiento de preparación de neramexane | |
JP2015511582A (ja) | 3−メチルスルホニルプロピオニトリルを調製するプロセス | |
JP2013544768A (ja) | ビカルタミドの調製方法 | |
CN105439837B (zh) | 6-溴异香草醛的合成方法 | |
CN110615751B (zh) | 一种2-氧代硫代丙酰胺的制备方法 | |
US20220024960A1 (en) | Improved synthesis of an expoxidation-catalyst | |
EP2307373A1 (en) | A process for preparing atovaquone and associate intermediates | |
EP2197273A1 (en) | Process for preparing r-gossypol l-phenylalaninol dienamine | |
JP3829273B2 (ja) | 光学活性なフラバノン及びクロマノン類の製造法 | |
CN112250533B (zh) | (s)-1-(3-乙氧基-4-甲氧基苯基)-2-(甲磺酰基)乙胺的合成方法 | |
CN112811970B (zh) | 一种2-烷氧基-2-环戊烯-1-酮的制备方法 | |
JP2000198779A (ja) | 3―アルキルフラバノノ―ル誘導体の精製法 | |
KR101733084B1 (ko) | 실로도신의 결정형의 제조방법 | |
WO2024033632A1 (en) | An improved process for preparing antiviral phosphonate analogues | |
JP6433809B2 (ja) | 1−(3−ヒドロキシメチルピリジル−2−)−2−フェニル−4−メチルピペラジンの製造方法 | |
KR101142052B1 (ko) | 자나미비어의 제조방법 | |
KR20000018793A (ko) | 1,2-벤즈이소티아졸린-3-온의 제조방법 | |
JP4225600B2 (ja) | クロモン類の製造法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20220815 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20230719 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230801 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230927 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20231003 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20231011 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7367147 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |