KR101944575B1 - 부제 촉매를 사용하는 2고리형 화합물의 광학 분할 방법 - Google Patents
부제 촉매를 사용하는 2고리형 화합물의 광학 분할 방법 Download PDFInfo
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- KR101944575B1 KR101944575B1 KR1020147015916A KR20147015916A KR101944575B1 KR 101944575 B1 KR101944575 B1 KR 101944575B1 KR 1020147015916 A KR1020147015916 A KR 1020147015916A KR 20147015916 A KR20147015916 A KR 20147015916A KR 101944575 B1 KR101944575 B1 KR 101944575B1
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- -1 bicyclic compound Chemical class 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 26
- 230000003287 optical effect Effects 0.000 title abstract description 7
- 239000011982 enantioselective catalyst Substances 0.000 title 1
- 150000001412 amines Chemical class 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 89
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 10
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 3
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 3
- 235000011009 potassium phosphates Nutrition 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 9
- 239000003446 ligand Substances 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- HDXYTIYVVNJFLU-HTQZYQBOSA-N (2r,5r)-2,5-bis(methoxymethyl)pyrrolidine Chemical compound COC[C@H]1CC[C@H](COC)N1 HDXYTIYVVNJFLU-HTQZYQBOSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- QEGONAXSXKFDLY-UHFFFAOYSA-N 3-ethylbicyclo[3.2.0]hept-3-en-6-one Chemical compound C1C(CC)=CC2C(=O)CC21 QEGONAXSXKFDLY-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- 108090000312 Calcium Channels Proteins 0.000 description 2
- 102000003922 Calcium Channels Human genes 0.000 description 2
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- FMNRMKKPPATKBJ-UHFFFAOYSA-N [7-[hydroxy(diphenyl)methyl]-1H-azepin-3-yl]-diphenylmethanol Chemical compound N1C(=CC=CC(=C1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1 FMNRMKKPPATKBJ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 208000004296 neuralgia Diseases 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QEGONAXSXKFDLY-HTQZYQBOSA-N (1r,5s)-3-ethylbicyclo[3.2.0]hept-3-en-6-one Chemical compound C1C(CC)=C[C@H]2C(=O)C[C@H]21 QEGONAXSXKFDLY-HTQZYQBOSA-N 0.000 description 1
- LPEYVMFVDGLNHH-MRXNPFEDSA-N (2R)-2-[bis(4-fluorophenyl)methyl]pyrrolidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)[C@@H]1NCCC1 LPEYVMFVDGLNHH-MRXNPFEDSA-N 0.000 description 1
- FRXBWKFANYNBEO-SSDOTTSWSA-N (2r)-2-(ethoxymethyl)pyrrolidine Chemical compound CCOC[C@H]1CCCN1 FRXBWKFANYNBEO-SSDOTTSWSA-N 0.000 description 1
- CHPRFKYDQRKRRK-ZCFIWIBFSA-N (2r)-2-(methoxymethyl)pyrrolidine Chemical compound COC[C@H]1CCCN1 CHPRFKYDQRKRRK-ZCFIWIBFSA-N 0.000 description 1
- CVINTVJDIQIIGZ-SNVBAGLBSA-N (2r)-2-(phenoxymethyl)pyrrolidine Chemical compound C([C@@H]1NCCC1)OC1=CC=CC=C1 CVINTVJDIQIIGZ-SNVBAGLBSA-N 0.000 description 1
- XSIXKZCGXXPTET-MRVPVSSYSA-N (2r)-2-(propan-2-yloxymethyl)pyrrolidine Chemical compound CC(C)OC[C@H]1CCCN1 XSIXKZCGXXPTET-MRVPVSSYSA-N 0.000 description 1
- VWXSCKOHAKPRKK-MRVPVSSYSA-N (2r)-2-[(2-methylpropan-2-yl)oxymethyl]pyrrolidine Chemical compound CC(C)(C)OC[C@H]1CCCN1 VWXSCKOHAKPRKK-MRVPVSSYSA-N 0.000 description 1
- PHKHWUVAUXBNPC-HXUWFJFHSA-N (2r)-2-[bis(3,5-dimethylphenyl)methyl]pyrrolidine Chemical compound CC1=CC(C)=CC(C([C@@H]2NCCC2)C=2C=C(C)C=C(C)C=2)=C1 PHKHWUVAUXBNPC-HXUWFJFHSA-N 0.000 description 1
- PYHLAJOBUXIDJW-GOSISDBHSA-N (2r)-2-[bis(4-methylphenyl)methyl]pyrrolidine Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)[C@@H]1NCCC1 PYHLAJOBUXIDJW-GOSISDBHSA-N 0.000 description 1
- RIWFUAUXWIEOTK-RXMQYKEDSA-N 1,1,1-trifluoro-n-[[(2r)-pyrrolidin-2-yl]methyl]methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NC[C@H]1CCCN1 RIWFUAUXWIEOTK-RXMQYKEDSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- CSXLVARCOLLWPI-RXMQYKEDSA-N 1-[(2R)-pyrrolidin-2-yl]tetrazole Chemical compound C1CN[C@@H](C1)n1cnnn1 CSXLVARCOLLWPI-RXMQYKEDSA-N 0.000 description 1
- VYXNJCCBPKNMBN-UHFFFAOYSA-N 1-nonylsulfinylnonane Chemical group CCCCCCCCCS(=O)CCCCCCCCC VYXNJCCBPKNMBN-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 1
- YRKRGYRYEQYTOH-UHFFFAOYSA-N 4-methylpyrrolidin-2-one Chemical compound CC1CNC(=O)C1 YRKRGYRYEQYTOH-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229960002870 gabapentin Drugs 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000000508 neurotrophic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 1
- 229960001233 pregabalin Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/12—Formation of amino and carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/20—All rings being cycloaliphatic the ring system containing seven carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JPJP-P-2011-274965 | 2011-12-15 | ||
| JP2011274965 | 2011-12-15 | ||
| PCT/JP2012/082355 WO2013089188A1 (ja) | 2011-12-15 | 2012-12-13 | 不斉触媒を用いる二環性化合物の光学分割方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20140107250A KR20140107250A (ko) | 2014-09-04 |
| KR101944575B1 true KR101944575B1 (ko) | 2019-04-17 |
Family
ID=48612629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147015916A Active KR101944575B1 (ko) | 2011-12-15 | 2012-12-13 | 부제 촉매를 사용하는 2고리형 화합물의 광학 분할 방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9035103B2 (https=) |
| EP (1) | EP2792664B1 (https=) |
| JP (1) | JP6017451B2 (https=) |
| KR (1) | KR101944575B1 (https=) |
| CN (1) | CN103987687B (https=) |
| BR (1) | BR112014014432B1 (https=) |
| CA (1) | CA2859003C (https=) |
| ES (1) | ES2686929T3 (https=) |
| HU (1) | HUE040225T2 (https=) |
| IL (1) | IL233104A (https=) |
| IN (1) | IN2014MN01046A (https=) |
| TW (1) | TWI546281B (https=) |
| WO (1) | WO2013089188A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI635071B (zh) * | 2013-07-08 | 2018-09-11 | 第一三共股份有限公司 | 光學活性二環γ－胺基酸衍生物及其製造方法 |
| US10150723B2 (en) * | 2015-05-27 | 2018-12-11 | Novassay S.A. | Separation of enantiomers of 3-ethylbicyclo[3.2.0]hept-3-en-6-one |
| WO2024134671A1 (en) * | 2022-12-21 | 2024-06-27 | Bhisaj Pharmaceuticals Pvt Ltd | Preparation of 3-ethylbicyclo[3.2.0]hept-3-en-6-one |
| CN116903468B (zh) * | 2023-07-14 | 2024-01-26 | 山东新时代药业有限公司 | 一种米洛巴林中间体的制备方法 |
| CN117924061B (zh) * | 2024-01-17 | 2026-03-20 | 北京海步医药科技有限公司 | 一种3-烷基双环[3.2.0]庚-3-烯-6-酮的拆分方法 |
| CN119798105A (zh) * | 2025-01-10 | 2025-04-11 | 长治医学院 | 一种米洛巴林的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010110361A1 (ja) | 2009-03-26 | 2010-09-30 | 第一三共株式会社 | 二環性γ－アミノ酸誘導体の製造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0074856A3 (en) * | 1981-09-16 | 1984-02-01 | Glaxo Group Limited | Resolution of racemic bicycloheptenones |
| JPS60169434A (ja) * | 1984-02-14 | 1985-09-02 | Ube Ind Ltd | 光学活性なビシクロケトン類の製法 |
| HUP0004310A3 (en) | 1997-10-27 | 2001-11-28 | Warner Lambert Co | Cyclic amino acids, and derivatives thereof and pharmaceutical compositions comprising the said compounds as active agents |
| HN2000000224A (es) | 1999-10-20 | 2001-04-11 | Warner Lambert Co | Aminoacidos biciclicos como agentes farmaceuticos |
| BR0208922A (pt) | 2001-04-19 | 2004-04-20 | Warner Lambert Co | Aminoácidos bicìclicos ou tricìclicos fundidos |
| US7465730B2 (en) | 2002-07-11 | 2008-12-16 | Merck & Co. Inc. | Treatment of neuropathic pain with 6H-pyrrolo[3,4-d]pyridazine compounds |
| EP2657219B1 (en) * | 2007-09-28 | 2014-12-10 | Daiichi Sankyo Company, Limited | Intermediate for producing bicyclic y-amino acid derivative |
| JP5336751B2 (ja) | 2007-12-12 | 2013-11-06 | 日東電工株式会社 | 液晶性コーティング液および偏光膜 |
| EP2719676B1 (en) * | 2011-06-08 | 2017-12-13 | Daiichi Sankyo Company, Limited | Method for producing bicyclic compound via iminium salt |
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2012
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- 2012-12-13 JP JP2013549310A patent/JP6017451B2/ja active Active
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| WO2010110361A1 (ja) | 2009-03-26 | 2010-09-30 | 第一三共株式会社 | 二環性γ－アミノ酸誘導体の製造方法 |
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| BR112014014432A2 (pt) | 2017-06-13 |
| IL233104A (en) | 2016-08-31 |
| ES2686929T3 (es) | 2018-10-22 |
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| EP2792664B1 (en) | 2018-07-04 |
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| EP2792664A1 (en) | 2014-10-22 |
| CA2859003A1 (en) | 2013-06-20 |
| BR112014014432B1 (pt) | 2022-03-29 |
| HK1199017A1 (en) | 2015-06-19 |
| CN103987687B (zh) | 2015-12-02 |
| IN2014MN01046A (https=) | 2015-05-01 |
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| TW201332955A (zh) | 2013-08-16 |
| CN103987687A (zh) | 2014-08-13 |
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| CA2859003C (en) | 2016-11-01 |
| IL233104A0 (en) | 2014-08-03 |
| US9035103B2 (en) | 2015-05-19 |
| US20140296569A1 (en) | 2014-10-02 |
| HUE040225T2 (hu) | 2019-02-28 |
| TWI546281B (zh) | 2016-08-21 |
| JP6017451B2 (ja) | 2016-11-02 |
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