KR850008485A - 나프록센의 제조방법 - Google Patents
나프록센의 제조방법 Download PDFInfo
- Publication number
- KR850008485A KR850008485A KR1019850003178A KR850003178A KR850008485A KR 850008485 A KR850008485 A KR 850008485A KR 1019850003178 A KR1019850003178 A KR 1019850003178A KR 850003178 A KR850003178 A KR 850003178A KR 850008485 A KR850008485 A KR 850008485A
- Authority
- KR
- South Korea
- Prior art keywords
- naphthyl
- chloro
- methoxy
- zinc
- acid
- Prior art date
Links
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 title claims 3
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 title claims 3
- 229960002009 naproxen Drugs 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- RPURXCRKUMBNJK-UHFFFAOYSA-N 1-chloro-2-methoxynaphthalene Chemical compound C1=CC=CC2=C(Cl)C(OC)=CC=C21 RPURXCRKUMBNJK-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- -1 ester compound Chemical class 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 229940102001 zinc bromide Drugs 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000011787 zinc oxide Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Pyrane Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 나프록센 [=(S)-2′-(6′-메톡시-2′-나프틸)-프로피은산]을 제조함에 있어서, a) 프리델-크라프트 반응에 따라 1-클로로-2-메톡시-나프탈렌을 다음 구조식,(여기서, X′ 및 X″는 동일 또는 상이한 것으로서, 염소 또는 브롬이다)의 화합물과 반응시키는 공정, b) 위에서 얻은 (S)-2-할로-1-(5′-클로로-6′-메톡시-2′-나프틸)-프로판-1-은을 대응하는 오로로-포름산염의 존재하에 저급지방족 알코올로 케탈화시키는 공정, c) 이 케탈화합물을 아연 무기유도체 존재하에 전위시켜서 알킬 (S)-2-(5′-클로로-6′-메톡시-2′-나프틸)-프로피오네이트를 얻는 공정, d) 이 에스테르 화합물을 산성 조건하에 가수분해시켜 (S)-2-(5′-클로로-6′-메톡시-2′-나프틸)-프로피은산을 얻는 공정, 그리고 e) 상기 산을 수소 첨가시키는 공정의 결합으로 구성된 것이 특징인 나프록센의 제조방법.
- 제1항에 있어서, 공정 e)가 공정 d) 보다 미리 진행되는 방법.
- 제2항에 있어서, 수소첨가가 중성 또는 산성조건에서 진행되는 방법.
- 제1항 내지 제3항중 임의의 항에 있어서, 공정 b)에서 메탄올 및 오르토-포름산메틸이 사용되는 방법.
- 제1항 내지 제4항중 임의의 항에 있어서, 공정 c)에서 사용되는 아연유도체가 염화아연, 브롬화아연 또는 산화아연인 방법.
- 제1항 내지 제5항중 임의의 항에 있어서, 공정 a)에서의 가수분해가 염산, 포름산 또는 초산을 사용하여 60℃ 이하의 온도에서 진행되는 방법.※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT20859/84A IT1174084B (it) | 1984-05-10 | 1984-05-10 | Procentimento per preparare il naproxen |
IT20859A/84 | 1984-05-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR850008485A true KR850008485A (ko) | 1985-12-18 |
Family
ID=11173137
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019850003178A KR850008485A (ko) | 1984-05-10 | 1985-05-10 | 나프록센의 제조방법 |
Country Status (16)
Country | Link |
---|---|
US (2) | US4736061A (ko) |
EP (1) | EP0163338B1 (ko) |
JP (1) | JPS6193135A (ko) |
KR (1) | KR850008485A (ko) |
AT (1) | ATE29486T1 (ko) |
AU (1) | AU579368B2 (ko) |
CA (1) | CA1238341A (ko) |
DE (1) | DE3560576D1 (ko) |
DK (1) | DK205685A (ko) |
ES (1) | ES542917A0 (ko) |
FI (1) | FI851847L (ko) |
IL (1) | IL75130A (ko) |
IT (1) | IT1174084B (ko) |
NO (1) | NO160437C (ko) |
PT (1) | PT80411B (ko) |
ZA (1) | ZA853411B (ko) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1221916B (it) * | 1987-03-13 | 1990-08-23 | Blaschim Spa | Metodo migliorato epr acilare un derivato del naftalene |
IT1227537B (it) * | 1987-07-28 | 1991-04-12 | Zambon Spa | Processo per la preparazione dell'acido s(+)-2-(6-metossi-2-naftil)- propionico |
IT1235649B (it) * | 1988-12-22 | 1992-09-18 | Zambon Spa | Processo per la preparazione del 2-metossi-6-propionil-naftalene per acilazione del 2-metossi-naftalene |
US5360938A (en) * | 1991-08-21 | 1994-11-01 | Union Carbide Chemicals & Plastics Technology Corporation | Asymmetric syntheses |
IT1251958B (it) * | 1991-10-18 | 1995-05-27 | Zambon Spa | Processo per la dealogenazione di derivati del naftalene |
US5792886A (en) * | 1997-01-08 | 1998-08-11 | Albemarle Corporation | Production of racemic 2-(6-methoxy-2-naphthyl) propionic acid of precursors thereof |
US6080888A (en) * | 1997-01-08 | 2000-06-27 | Albemarle Corporation | Preparation of olefinic compounds and carboxylic derivatives thereof |
US6096920A (en) * | 1997-01-08 | 2000-08-01 | Albemarle Corporation | Preparation of carboxylic compounds and their derivatives |
US5874614A (en) * | 1997-12-11 | 1999-02-23 | Albemarle Corporation | Sodium (S)-2-(6-methoxy-2-naphthyl)propionate monohydrate |
US5859292A (en) * | 1997-12-11 | 1999-01-12 | Albemarle Corporation | Preparation of high purity sodium (S)-2(6-methoxy-2-naphthyl)propionate |
SK16482002A3 (sk) * | 2002-11-20 | 2004-06-08 | Slovakofarma, A. S. | Spôsob prípravy substituovaných derivátov 2-aryl alkánových kyselín |
CN109761803A (zh) * | 2019-01-29 | 2019-05-17 | 湖南九典制药股份有限公司 | 一种萘普生关键中间体的合成方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3884950A (en) * | 1973-12-13 | 1975-05-20 | Toray Silicone Co | Organopolysiloxane composition having improved heat stability |
US4107439A (en) * | 1976-06-16 | 1978-08-15 | The Upjohn Company | Process for preparing arylalkanoic acid derivatives |
IE50898B1 (en) * | 1980-02-26 | 1986-08-06 | Blaschim Spa | Process for preparing esters of 2-(6'-methoxy-2'-naphthyl)-propionic acid via rearrangement of new ketals of 2-halo-1-(6'-methoxy-2'-naphthyl)-propan-1-one |
IT1168387B (it) * | 1981-04-01 | 1987-05-20 | Alfa Farmaceutici Spa | Procedimento per la preparazione dell'acido 2-(6-metossi-2-naftil)-propionico |
JPS5810525A (ja) * | 1981-06-15 | 1983-01-21 | Sagami Chem Res Center | 光学活性な1−芳香族基置換−1−アルカノン類の製造方法 |
IT1167476B (it) * | 1981-07-23 | 1987-05-13 | Blasinachim Spa | Procedimento per preparare acidi alcanoici o i loro esteri mediante riarrangiamento di alfa-alogeno-chetoni in mezzo protico e in presenza di un sale di un metallo non nobile |
FI82680C (fi) * | 1981-12-11 | 1991-04-10 | Syntex Pharma Int | Framstaellning av - arylalkansyror. |
US4510321A (en) * | 1983-01-31 | 1985-04-09 | Allied Corporation | Autoxidative cleavage of ketones in the presence of pulverized alkali metal hydroxide |
DE3461525D1 (en) * | 1984-02-02 | 1987-01-15 | Zambon Spa | Process for preparing alpha-arylalkanoic acids |
IT1173369B (it) * | 1984-02-24 | 1987-06-24 | Zambon Spa | Processo per la preparazione di acidi alfa-arilalcanoici otticamente attivi |
-
1984
- 1984-05-10 IT IT20859/84A patent/IT1174084B/it active
-
1985
- 1985-05-01 EP EP85200682A patent/EP0163338B1/en not_active Expired
- 1985-05-01 DE DE8585200682T patent/DE3560576D1/de not_active Expired
- 1985-05-01 AT AT85200682T patent/ATE29486T1/de not_active IP Right Cessation
- 1985-05-06 ZA ZA853411A patent/ZA853411B/xx unknown
- 1985-05-06 AU AU41998/85A patent/AU579368B2/en not_active Ceased
- 1985-05-08 PT PT80411A patent/PT80411B/pt not_active IP Right Cessation
- 1985-05-08 ES ES542917A patent/ES542917A0/es active Granted
- 1985-05-08 NO NO851828A patent/NO160437C/no unknown
- 1985-05-08 CA CA000481094A patent/CA1238341A/en not_active Expired
- 1985-05-08 IL IL75130A patent/IL75130A/xx unknown
- 1985-05-09 DK DK205685A patent/DK205685A/da not_active Application Discontinuation
- 1985-05-09 FI FI851847A patent/FI851847L/fi not_active Application Discontinuation
- 1985-05-10 US US06/732,735 patent/US4736061A/en not_active Expired - Fee Related
- 1985-05-10 JP JP60098156A patent/JPS6193135A/ja active Pending
- 1985-05-10 KR KR1019850003178A patent/KR850008485A/ko not_active Application Discontinuation
-
1987
- 1987-12-23 US US07/137,366 patent/US4864063A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
ES8603373A1 (es) | 1986-01-01 |
FI851847L (fi) | 1985-11-11 |
NO160437B (no) | 1989-01-09 |
PT80411B (en) | 1986-12-15 |
ATE29486T1 (de) | 1987-09-15 |
IT8420859A0 (it) | 1984-05-10 |
DE3560576D1 (en) | 1987-10-15 |
US4736061A (en) | 1988-04-05 |
DK205685A (da) | 1985-11-11 |
AU579368B2 (en) | 1988-11-24 |
FI851847A0 (fi) | 1985-05-09 |
JPS6193135A (ja) | 1986-05-12 |
ES542917A0 (es) | 1986-01-01 |
EP0163338A1 (en) | 1985-12-04 |
US4864063A (en) | 1989-09-05 |
NO160437C (no) | 1989-04-19 |
IT1174084B (it) | 1987-07-01 |
IT8420859A1 (it) | 1985-11-10 |
EP0163338B1 (en) | 1987-09-09 |
CA1238341A (en) | 1988-06-21 |
DK205685D0 (da) | 1985-05-09 |
ZA853411B (en) | 1986-03-26 |
NO851828L (no) | 1985-11-11 |
AU4199885A (en) | 1985-11-14 |
IL75130A0 (en) | 1985-09-29 |
PT80411A (en) | 1985-06-01 |
IL75130A (en) | 1988-07-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR850008485A (ko) | 나프록센의 제조방법 | |
Corey et al. | New methods for the oxidation of aldehydes to carboxylic acids and esters | |
McElvain et al. | The preparation, alcoholysis and reduction of cyanoacetaldehyde diethylacetal. Malonaldehyde tetraethylacetal | |
KR860000236A (ko) | 유기산의 트리테르페닐의 에스테르의 제조방법 | |
KR830003465A (ko) | 콜레스테롤 합성의 치환 피라논 억제제의 제조방법 | |
KR940011422A (ko) | 방향족 알데하이드의 제조방법 | |
US2759966A (en) | Esters of phenyl substituted dihydroxybenzoic acids | |
KR880000376A (ko) | 페닐 α-플루오로아크릴레이트의 제조방법 | |
KR920007975A (ko) | d-2-(6-메톡시-2-나프틸)-프로피온산의 제조방법 및 그 중간체 | |
McBee et al. | The Chemistry of 1, 1, 1-Trifluoropropanone. II. 1 The Reactions of 4-Methyl-1, 1, 1, 5, 5, 5-hexafluoro-3-penten-2-one with Methylmagnesium Iodide2, 3 | |
KR870009978A (ko) | 알파, 베타-불포화 카보닐 화합물의 촉매적 가수분해 방법 | |
EP0138521B1 (en) | Process for preparing d-alpha-(6-methoxy-2-naphthyl)propionic acid | |
JPH0662488B2 (ja) | バルプロ酸の製造方法 | |
Zelinski et al. | Preparation of 2-Cyanotetrahydropyran | |
KR870009981A (ko) | 2,3,4,5-테트라플루오로벤조일 아세테이트의 제조방법 | |
YU et al. | Acid-Catalyzed Condensation of Phenols and Keto Acids | |
Adams et al. | The structure of monocrotaline. III. Monocrotalic acid | |
JPS54122220A (en) | Preparation of high purity isoprenyl acetic acid | |
KR910007956A (ko) | 21-데스옥시프레드니솔론 17-에스테르의 제조방법 | |
Marvel et al. | New Compounds. m-Bromo-n-alkylbenzenes | |
JPS6121941B2 (ko) | ||
ES545150A0 (es) | Procedimiento para la preparacion de hidratos de fluoral y de hexafluoracetona puros a partir de hemiacetales | |
KR840001940A (ko) | 5-페닐-2s-펜탄올의 입체특이적 합성법 | |
JPS5492915A (en) | Preparation of beta-hydroxyamino acid | |
SU56886A1 (ru) | Способ получени моно- и диалкилированных и ацилированных производных кетоэнолов |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E601 | Decision to refuse application |