KR830008973A - d-2-(6-메톡시-2-나프틸)-프로피온산의 제조방법 - Google Patents
d-2-(6-메톡시-2-나프틸)-프로피온산의 제조방법 Download PDFInfo
- Publication number
- KR830008973A KR830008973A KR1019820001353A KR820001353A KR830008973A KR 830008973 A KR830008973 A KR 830008973A KR 1019820001353 A KR1019820001353 A KR 1019820001353A KR 820001353 A KR820001353 A KR 820001353A KR 830008973 A KR830008973 A KR 830008973A
- Authority
- KR
- South Korea
- Prior art keywords
- naphthyl
- methoxy
- propionic acid
- mixture
- nickel
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 7
- 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims 6
- 229910000838 Al alloy Inorganic materials 0.000 claims 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 238000005984 hydrogenation reaction Methods 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910000990 Ni alloy Inorganic materials 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000000654 additive Substances 0.000 claims 3
- 230000000996 additive effect Effects 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 238000005695 dehalogenation reaction Methods 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 239000007868 Raney catalyst Substances 0.000 claims 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims 2
- 239000003610 charcoal Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 229910052987 metal hydride Inorganic materials 0.000 claims 2
- 150000004681 metal hydrides Chemical class 0.000 claims 2
- 229910052759 nickel Inorganic materials 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 2
- 239000012279 sodium borohydride Substances 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- -1 5-bromo-6-methoxy-2-naphthyl Chemical group 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- XLVAVZLFABUPKX-UHFFFAOYSA-J S(=O)(=O)([O-])[O-].[Cu+4].S(=O)(=O)([O-])[O-] Chemical compound S(=O)(=O)([O-])[O-].[Cu+4].S(=O)(=O)([O-])[O-] XLVAVZLFABUPKX-UHFFFAOYSA-J 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims 1
- 229910045601 alloy Inorganic materials 0.000 claims 1
- 239000000956 alloy Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 1
- 229910010277 boron hydride Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011159 matrix material Substances 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (14)
- 아래 I식의 d-2-(6-메톡시-2-나프틸)-프로피온산을 제조하는 방법에 있어서,상기 제조방법은 할로(halo)가 할로겐원자로 나타내는 다음 II식의 d- 및 ℓ-2-(5-할로-6-메톡시-2-나프틸)-프로피온산 혼합물을 광학불활성유기 또는 무기염기의 존재하에 대략 실내온도와 약 65℃사이의 온도에서 톨루엔 및 메타놀 혼합물로 부터 각종 용적비율로 선택된 용매계 속에 용해된 N-메칠-D-글루카민으로 처리하고,불용성인 d-이성체의 N-메칠-D-글루카민염을 회수한 후에, 상기 염을 강력한 광산과 접촉시키므로서 이때 다음 III식의 d-2-(5-할로-6-메톡시-2-나프틸)-프로피온산화합물이 얻어지며,그 화합물을 대략 실내온도와 약 100℃사이의 온도하에 약 1시간 내지 약 4시간 동안 알칼리성매질 속에서 5-위치에 있는 할로겐원자를 수소원자에 의한 완전치환을 제공할 수 있는 적절한 수소첨가계로 처리하므로서 촉매탈할로겐화 시키는 제조방법.
- 청구범위 1에서, d- 및 ℓ-2-(5-할로-6-메톡시-2-나프틸)-프로피온산 혼합물을 주로 라세미 혼합인 것을 특징으로 하는 제조방법.
- 청구범위 2에서, 주로 라세미 혼합물인 d- 및 ℓ-2-(5-할로-6-메톡시-2-나프틸)-프로피온산의 각 몰량을 위에서 N-메칠-D-글루카민의 대략 1/2몰량이 사용되는 제조방법.
- 청구범위 1에서 할로는 취소원자로 되는 제조방법.
- 청구범위 1에서 톨루엔 및 메타놀 혼합물은 4/1 또는 3/1(V/V)혼합물로 되는 제조방법.
- 청구범위 1에서 광학분할이 이루어지는 온도는 대략 실내 온도 내지 약 55℃ 사이에서 선정되는 제조방법.
- 청구범위 1에서 수소첨가제는 파라디움/목탄 또는 이산화백금과 혼합된 금속수소화물과 전이금속의 혼합물, 데바르다의 합금과 혼합된 금속수소화물의 혼합물, 라네이 낵켈과 포수(抱水)히느러진, 닉켈/알루미늄합금과 포수히드라진의 혼합물로부터 선정되는 제조방법.
- 청구범위 7에서 수소첨가제는 파리디움/목탄과 수소화붕소 니트리움인 것을 특징으로 하는 제조방법.
- 청구범위 7에서 수소첨가제는 5포수황산동와 수소화붕소 나트륨인 것을 특징으로하는 제조방법.
- 청구범위 7에서 수소첨가제는 라네이닉켈 또는 50/50(중량으로) 닉켈알루미늄합금 및 포수히드라진인 것을 특징으로 하는 제조방법.
- 청구범위 1에서 탈할로겐화는 라네이 닉켈 또는 닉켈/알미늄합금 및 포수히드라진 들이 수소첨가게로서 사용될 때에는 대략 실내온도와 약 50℃사이의 온도에서 실시되는 제조방법.
- 아래 I식의 d-2-(6-메톡시-2-나프틸)-프로피온산을 제조하는 방법에 있어서,상기 제조법은 다음 X식의 주로 라세비 혼합물인 d- 및 1-2-(5-브로모-6-메톡시-2-나프틸)-프로피온산의 1몰량을 반응용제로서 4/1(V/V) 톨루엔/메타놀혼합물의 존재하에, 또한 트리에칠아민 약 1/2몰량의 존재하에 대략 실내온도와 약 55℃사이의 온도에서 약 1/2몰비율의 N-메칠-D-글루카민으로 처리하고,d-이성체의 불용성 N-메칠-D-글루카민염을 회수한 후에 상기 염을 강력한 광산과 접촉시키므로서 다음 X식의 d-2-(5-브로모-6-메톡시-2-나프틸)-프로피온산 화합물이 얻어지며,상기 화합물을 알칼리성 매칠 속에서 대략 실내온도와 약 100℃사이의 온도하에 약 1시간 내지 약 4시간 동안 5-위치에 있는 할로겐원자를 수소원자에 의한 완전치환 제공할 수 있는 수소첨가계로 처리하므로서 촉매탈할로겐화시키며, 이때 상기 수소첨가제는 5% 파라디움/목탄과 수소화붕소나트륨, 닉켈/알미늄합금과 100% 포수히드라진, 라네이 닉켈과 100% 포수히드라진으로부터 선정되는 단계로 이루어지는 제조방법.
- 청구범위 12에 수소첨가제는 라네이닉켈 또는 50/50(중량으로) 닉켈/알미늄 합금, 그리고 100% 포수히드라진인 것을 특징으로 하는 제조방법.
- d-2-(5-브로모-6-메톡시-2-나프틸) 프로피온산의 N-메칠-D-글루카민염.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3385A/81 | 1981-04-01 | ||
| IT03385/81A IT1168387B (it) | 1981-04-01 | 1981-04-01 | Procedimento per la preparazione dell'acido 2-(6-metossi-2-naftil)-propionico |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830008973A true KR830008973A (ko) | 1983-12-16 |
| KR860001547B1 KR860001547B1 (ko) | 1986-10-04 |
Family
ID=11106122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8201353A KR860001547B1 (ko) | 1981-04-01 | 1982-03-29 | d-2-(6-메톡시-2-나프틸)-프로피온산의 제조방법 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4423244A (ko) |
| JP (1) | JPS57176925A (ko) |
| KR (1) | KR860001547B1 (ko) |
| AR (1) | AR230614A1 (ko) |
| AT (1) | AT390253B (ko) |
| BE (1) | BE892689A (ko) |
| CA (1) | CA1190939A (ko) |
| CH (1) | CH651289A5 (ko) |
| DE (1) | DE3212170A1 (ko) |
| DK (2) | DK157076C (ko) |
| ES (1) | ES8302622A1 (ko) |
| FI (1) | FI78455C (ko) |
| FR (1) | FR2504918B1 (ko) |
| GB (1) | GB2098981B (ko) |
| GR (1) | GR76062B (ko) |
| HU (1) | HU186852B (ko) |
| IE (1) | IE52378B1 (ko) |
| IL (1) | IL65298A (ko) |
| IT (1) | IT1168387B (ko) |
| LU (1) | LU84044A1 (ko) |
| NL (1) | NL8201307A (ko) |
| NO (1) | NO157733B (ko) |
| PT (1) | PT74677B (ko) |
| SE (2) | SE453492C (ko) |
| YU (1) | YU42606B (ko) |
| ZA (1) | ZA822145B (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS262412B2 (en) * | 1982-05-27 | 1989-03-14 | Syntex Pharma Int | Process for preparing d-2-/6-methoxy-2-naphthyl/propionic acid |
| FI831820L (fi) * | 1982-05-27 | 1983-11-28 | Syntex Pharma Int | Foerfarande foer framstaellning av d-2-(6-metoxi-2-naftyl)-propionsyra och dess farmaceutiskt godtagbara salter samt av nya mellanprodukter anvaenda vid deras framstaellning |
| US4723033A (en) * | 1982-11-24 | 1988-02-02 | Syntex Pharmaceuticals International Ltd. | Manufacture of optically active α-arylalkanoic acids and precursors thereof |
| IT1174084B (it) * | 1984-05-10 | 1987-07-01 | Blaschim Spa | Procentimento per preparare il naproxen |
| US4814497A (en) * | 1986-05-12 | 1989-03-21 | Ethyl Corporation | Dehalogenation process |
| IT1238008B (it) * | 1990-02-08 | 1993-06-21 | Alfa Wassermann Spa | Procedimento per la debromurazione di 2-sostituiti-5-bromo- 6-metossinaftaleni |
| FR2686877B1 (fr) * | 1992-01-31 | 1995-03-24 | Hoechst France | Procede de preparation de l'acide orthohydroxyphenylacetique. |
| JPH0646907U (ja) * | 1992-12-10 | 1994-06-28 | リョービ株式会社 | すべり勾配面加工用治具 |
| US5574183A (en) * | 1995-01-24 | 1996-11-12 | Albemarle Corporation | Preparation of optically active aliphatic carboxylic acids |
| US6552078B2 (en) | 1999-10-27 | 2003-04-22 | Nobex Corp | 6-methoxy-2-naphthylacetic acid prodrugs |
| TWI262791B (en) | 1999-10-27 | 2006-10-01 | Nobex Corp | 6-methoxy-2-naphthylacetic acid prodrugs |
| US6436990B1 (en) | 1999-10-27 | 2002-08-20 | Nobex Corporation | 6-methoxy-2-naphthylacetic acid prodrugs |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3904682A (en) * | 1967-01-13 | 1975-09-09 | Syntex Corp | 2-(6{40 -Methoxy-2{40 -naphthyl)acetic acid |
| US3637767A (en) * | 1968-07-30 | 1972-01-25 | Syntex Corp | 2-(6'-methoxynaphth-2'-yl)propylene oxide and 5'-halo derivatives |
| US3686183A (en) * | 1969-03-24 | 1972-08-22 | Syntex Corp | Preparation of optical isomers of arylalkylacetic acids |
| CA936171A (en) * | 1970-09-09 | 1973-10-30 | Syntex Corporation | Process for preparing 2-(6-methoxy-2-naphthyl) propionic acid and 2-(6-methoxy-2-naphthyl)-1-propanol |
| CH641432A5 (de) * | 1978-07-19 | 1984-02-29 | Syntex Pharma Int | Verfahren zur aufspaltung von racemischer 6-methoxy-alpha-methyl-2-naphthalinessigsaeure in die optischen antipoden. |
| PH15674A (en) * | 1979-07-06 | 1983-03-11 | Syntex Corp | Process for the resolution of d,1 2-(6-methoxy-2-naphthyl)propionic acid |
-
1981
- 1981-04-01 IT IT03385/81A patent/IT1168387B/it active
-
1982
- 1982-03-21 IL IL65298A patent/IL65298A/xx not_active IP Right Cessation
- 1982-03-29 KR KR8201353A patent/KR860001547B1/ko not_active IP Right Cessation
- 1982-03-29 ZA ZA822145A patent/ZA822145B/xx unknown
- 1982-03-29 US US06/362,679 patent/US4423244A/en not_active Expired - Lifetime
- 1982-03-30 LU LU84044A patent/LU84044A1/fr unknown
- 1982-03-30 PT PT74677A patent/PT74677B/pt unknown
- 1982-03-30 NL NL8201307A patent/NL8201307A/nl not_active Application Discontinuation
- 1982-03-30 ES ES510931A patent/ES8302622A1/es not_active Expired
- 1982-03-30 BE BE2/59651A patent/BE892689A/fr not_active IP Right Cessation
- 1982-03-30 GR GR67765A patent/GR76062B/el unknown
- 1982-03-31 HU HU82994A patent/HU186852B/hu not_active IP Right Cessation
- 1982-03-31 CA CA000400096A patent/CA1190939A/en not_active Expired
- 1982-03-31 SE SE8202050A patent/SE453492C/sv not_active IP Right Cessation
- 1982-03-31 DK DK147482A patent/DK157076C/da not_active IP Right Cessation
- 1982-03-31 AT AT0127082A patent/AT390253B/de not_active IP Right Cessation
- 1982-03-31 IE IE770/82A patent/IE52378B1/en not_active IP Right Cessation
- 1982-03-31 NO NO821088A patent/NO157733B/no unknown
- 1982-03-31 AR AR288954A patent/AR230614A1/es active
- 1982-03-31 CH CH1987/82A patent/CH651289A5/de not_active IP Right Cessation
- 1982-03-31 JP JP57054723A patent/JPS57176925A/ja active Granted
- 1982-03-31 FR FR8205530A patent/FR2504918B1/fr not_active Expired
- 1982-03-31 FI FI821121A patent/FI78455C/fi not_active IP Right Cessation
- 1982-03-31 YU YU720/82A patent/YU42606B/xx unknown
- 1982-04-01 DE DE19823212170 patent/DE3212170A1/de active Granted
- 1982-04-01 GB GB8209661A patent/GB2098981B/en not_active Expired
-
1985
- 1985-04-09 SE SE8501744A patent/SE466199B/sv not_active IP Right Cessation
-
1989
- 1989-05-26 DK DK256589A patent/DK256589A/da not_active Application Discontinuation
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