JPS5965075A - （±）−２−（６−メトキシ−２−ナフチル）プロピオン酸の光学分割法 - Google Patents
（±）−２−（６−メトキシ−２−ナフチル）プロピオン酸の光学分割法Info
- Publication number
- JPS5965075A JPS5965075A JP17456882A JP17456882A JPS5965075A JP S5965075 A JPS5965075 A JP S5965075A JP 17456882 A JP17456882 A JP 17456882A JP 17456882 A JP17456882 A JP 17456882A JP S5965075 A JPS5965075 A JP S5965075A
- Authority
- JP
- Japan
- Prior art keywords
- naphthyl
- propionic acid
- medoxy
- salt
- methoxy
- 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.)
- Granted
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 20
- CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 48
- 235000019260 propionic acid Nutrition 0.000 claims description 24
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 21
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 13
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- DKVIPUUJSKIQFZ-UHFFFAOYSA-N 2-naphthalen-2-ylpropanoic acid Chemical compound C1=CC=CC2=CC(C(C(O)=O)C)=CC=C21 DKVIPUUJSKIQFZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 abstract description 19
- -1 2-(6-Methoxy-2-naphthyl)propionic acid 4-methyl-piperidine salt Chemical class 0.000 abstract description 8
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 8
- 230000000202 analgesic effect Effects 0.000 abstract description 2
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 2
- SEVXEIGENOCFRM-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)propanoic acid;4-methylpiperidine Chemical compound CC1CCNCC1.C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 SEVXEIGENOCFRM-UHFFFAOYSA-N 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QHIHDPRSJIBZKU-UHFFFAOYSA-N 1-methyl-4-naphthalen-1-ylnaphthalene Chemical group C12=CC=CC=C2C(C)=CC=C1C1=CC=CC2=CC=CC=C12 QHIHDPRSJIBZKU-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical class CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- VKCNNDPZFOVURD-UHFFFAOYSA-N 2-naphthalen-1-ylpropanoic acid Chemical class C1=CC=C2C(C(C(O)=O)C)=CC=CC2=C1 VKCNNDPZFOVURD-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XHKYACWISXFMHD-UHFFFAOYSA-N n-[bis(dimethylamino)phosphoryl]-n-methylmethanamine;methylsulfinylmethane Chemical compound CS(C)=O.CN(C)P(=O)(N(C)C)N(C)C XHKYACWISXFMHD-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17456882A JPS5965075A (ja) | 1982-10-06 | 1982-10-06 | （±）−２−（６−メトキシ−２−ナフチル）プロピオン酸の光学分割法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17456882A JPS5965075A (ja) | 1982-10-06 | 1982-10-06 | （±）−２−（６−メトキシ−２−ナフチル）プロピオン酸の光学分割法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11513990A Division JPH02288843A (ja) | 1990-05-02 | 1990-05-02 | ２―（６―メトキシ―２―ナフチル）プロピオン酸４―メチルピペリジン塩 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5965075A true JPS5965075A (ja) | 1984-04-13 |
| JPH0259817B2 JPH0259817B2 (enrdf_load_stackoverflow) | 1990-12-13 |
Family
ID=15980830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17456882A Granted JPS5965075A (ja) | 1982-10-06 | 1982-10-06 | （±）−２−（６−メトキシ−２−ナフチル）プロピオン酸の光学分割法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5965075A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0298395B1 (en) * | 1987-07-10 | 1992-01-29 | PROFARMACO NOBEL S.r.l. | A process for the optical resolution of 2-(6-methoxy-2-naphthyl) propionic acid |
| JP2012521392A (ja) * | 2009-03-26 | 2012-09-13 | ポクセル・エスアーエス | 優先晶出法を利用したジヒドロ−１，３，５トリアジンラセミ体のエナンチオマー分離のための方法 |
-
1982
- 1982-10-06 JP JP17456882A patent/JPS5965075A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0298395B1 (en) * | 1987-07-10 | 1992-01-29 | PROFARMACO NOBEL S.r.l. | A process for the optical resolution of 2-(6-methoxy-2-naphthyl) propionic acid |
| JP2012521392A (ja) * | 2009-03-26 | 2012-09-13 | ポクセル・エスアーエス | 優先晶出法を利用したジヒドロ−１，３，５トリアジンラセミ体のエナンチオマー分離のための方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0259817B2 (enrdf_load_stackoverflow) | 1990-12-13 |
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