SK278340B6 - Separation method of (+)-2-(6-methoxy-2-naphtyl)propionic acid from mixture of (+) and (-)-2-(6-methoxy-2-naphtyl)propionic acids - Google Patents
Separation method of (+)-2-(6-methoxy-2-naphtyl)propionic acid from mixture of (+) and (-)-2-(6-methoxy-2-naphtyl)propionic acids Download PDFInfo
- Publication number
- SK278340B6 SK278340B6 SK4774-80A SK477480A SK278340B6 SK 278340 B6 SK278340 B6 SK 278340B6 SK 477480 A SK477480 A SK 477480A SK 278340 B6 SK278340 B6 SK 278340B6
- Authority
- SK
- Slovakia
- Prior art keywords
- methoxy
- naphthyl
- glucamine
- propionic acid
- salt
- Prior art date
Links
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- 238000000926 separation method Methods 0.000 title abstract 2
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- 238000000034 method Methods 0.000 claims abstract description 37
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- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
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- 239000012059 conventional drug carrier Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
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- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 210000000754 myometrium Anatomy 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 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 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008299 semisolid dosage form Substances 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- CDBRNDSHEYLDJV-UHFFFAOYSA-M sodium;2-(6-methoxynaphthalen-2-yl)propanoate Chemical compound [Na+].C1=C(C(C)C([O-])=O)C=CC2=CC(OC)=CC=C21 CDBRNDSHEYLDJV-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C07C51/50—Use of additives, e.g. for stabilisation
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/38—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
- C07C57/40—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic containing condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5525879A | 1979-07-06 | 1979-07-06 | |
| US06/097,118 US4246193A (en) | 1979-11-26 | 1979-11-26 | Process for the resolution of d,1 2-(6-methoxy-2-naphthyl)propionic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK278340B6 true SK278340B6 (en) | 1996-12-04 |
Family
ID=26734026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK4774-80A SK278340B6 (en) | 1979-07-06 | 1980-07-03 | Separation method of (+)-2-(6-methoxy-2-naphtyl)propionic acid from mixture of (+) and (-)-2-(6-methoxy-2-naphtyl)propionic acids |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0022529B1 (en, 2012) |
| JP (2) | JPS63313749A (en, 2012) |
| KR (1) | KR830000769B1 (en, 2012) |
| AR (1) | AR225927A1 (en, 2012) |
| AU (1) | AU544963B2 (en, 2012) |
| CA (1) | CA1135717A (en, 2012) |
| CZ (1) | CZ277725B6 (en, 2012) |
| DD (1) | DD153367A5 (en, 2012) |
| DE (3) | DE3051036C2 (en, 2012) |
| DK (2) | DK156051C (en, 2012) |
| ES (1) | ES8105691A1 (en, 2012) |
| FR (2) | FR2472557A1 (en, 2012) |
| GB (1) | GB2054579B (en, 2012) |
| GR (1) | GR68796B (en, 2012) |
| HK (1) | HK886A (en, 2012) |
| IE (1) | IE50000B1 (en, 2012) |
| IL (1) | IL60498A (en, 2012) |
| IN (1) | IN152737B (en, 2012) |
| IT (1) | IT1130490B (en, 2012) |
| MY (1) | MY8600452A (en, 2012) |
| NZ (1) | NZ194237A (en, 2012) |
| PH (4) | PH15674A (en, 2012) |
| PL (1) | PL133439B1 (en, 2012) |
| PT (1) | PT71486A (en, 2012) |
| RO (1) | RO80655B (en, 2012) |
| SK (1) | SK278340B6 (en, 2012) |
| YU (1) | YU42673B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1168387B (it) * | 1981-04-01 | 1987-05-20 | Alfa Farmaceutici Spa | Procedimento per la preparazione dell'acido 2-(6-metossi-2-naftil)-propionico |
| ZA828453B (en) * | 1981-12-08 | 1983-12-28 | Boots Co Plc | Therapeutic agents |
| IT1196197B (it) * | 1984-07-23 | 1988-11-10 | Ravizza Spa | Procedimento per la risoluzione dell'acido (+)(-) 2-(2'-(p-fluorofenil)--5'-benzossazolil)-propionico |
| GB9121279D0 (en) * | 1991-10-08 | 1991-11-20 | Cerestar Holding Bv | Process for the production of aminopolyols |
| US5574183A (en) * | 1995-01-24 | 1996-11-12 | Albemarle Corporation | Preparation of optically active aliphatic carboxylic acids |
| KR100678287B1 (ko) * | 2005-06-23 | 2007-02-02 | 한미약품 주식회사 | 클로피도그렐의 제조방법 및 이에 사용되는 중간체 |
| KR101170537B1 (ko) * | 2010-01-11 | 2012-08-01 | 김창운 | 해수의 자연순환이 가능한 내륙 내 바다양식 수조 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1668654B2 (de) * | 1967-01-13 | 1976-11-04 | Syntex Corp., Panama | 2-(6'-substituierte-2'-naphthyl)- propionsaeuren und -derivate, ihre herstellung und sie enthaltende arzneimittel |
| US3904682A (en) * | 1967-01-13 | 1975-09-09 | Syntex Corp | 2-(6{40 -Methoxy-2{40 -naphthyl)acetic acid |
| ZA70809B (en) * | 1969-03-24 | 1971-09-29 | Syntex Corp | Amine salts of 2-(6'-methoxy-2'-naphthyl)propionic acids and processes for the preparation thereof |
| US3686183A (en) * | 1969-03-24 | 1972-08-22 | Syntex Corp | Preparation of optical isomers of arylalkylacetic acids |
| US3904683A (en) * | 1972-08-10 | 1975-09-09 | Syntex Corp | Process for the resolution of d- and 1-2-(6-methoxy-2-naphthyl) propionic acid |
| GR64816B (en) * | 1977-03-08 | 1980-06-03 | Boots Co Ltd | Resolution of flurbiprofen ii/iii |
| 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. |
-
1980
- 1980-07-01 PH PH24217A patent/PH15674A/en unknown
- 1980-07-02 CA CA000355255A patent/CA1135717A/en not_active Expired
- 1980-07-02 PT PT71486A patent/PT71486A/pt active IP Right Revival
- 1980-07-03 SK SK4774-80A patent/SK278340B6/sk unknown
- 1980-07-03 YU YU1743/80A patent/YU42673B/xx unknown
- 1980-07-03 IT IT68053/80A patent/IT1130490B/it active
- 1980-07-03 CZ CS804774A patent/CZ277725B6/cs not_active IP Right Cessation
- 1980-07-04 IN IN774/CAL/80A patent/IN152737B/en unknown
- 1980-07-04 DE DE3051036A patent/DE3051036C2/de not_active Expired
- 1980-07-04 AU AU60121/80A patent/AU544963B2/en not_active Expired
- 1980-07-04 DK DK289080A patent/DK156051C/da not_active IP Right Cessation
- 1980-07-04 DE DE8080103828T patent/DE3063969D1/de not_active Expired
- 1980-07-04 RO RO101603A patent/RO80655B/ro unknown
- 1980-07-04 NZ NZ194237A patent/NZ194237A/en unknown
- 1980-07-04 EP EP80103828A patent/EP0022529B1/en not_active Expired
- 1980-07-04 ES ES493126A patent/ES8105691A1/es not_active Expired
- 1980-07-04 KR KR1019800002661A patent/KR830000769B1/ko not_active Expired
- 1980-07-04 PL PL1980225474A patent/PL133439B1/pl unknown
- 1980-07-04 DE DE19803025448 patent/DE3025448A1/de active Granted
- 1980-07-04 IE IE1396/80A patent/IE50000B1/en unknown
- 1980-07-04 GB GB8022029A patent/GB2054579B/en not_active Expired
- 1980-07-04 DD DD80222419A patent/DD153367A5/de unknown
- 1980-07-04 IL IL60498A patent/IL60498A/xx unknown
- 1980-07-04 GR GR62380A patent/GR68796B/el unknown
- 1980-07-04 AR AR281671A patent/AR225927A1/es active
- 1980-07-04 FR FR8015013A patent/FR2472557A1/fr active Granted
- 1980-12-31 FR FR8027894A patent/FR2470108A1/fr active Granted
-
1981
- 1981-05-15 PH PH25634A patent/PH16328A/en unknown
- 1981-05-15 PH PH25636A patent/PH16432A/en unknown
- 1981-05-15 PH PH25633A patent/PH16431A/en unknown
-
1986
- 1986-01-02 HK HK8/86A patent/HK886A/en not_active IP Right Cessation
- 1986-12-30 MY MY452/86A patent/MY8600452A/xx unknown
-
1988
- 1988-04-13 JP JP63089153A patent/JPS63313749A/ja active Granted
- 1988-05-03 DK DK239988A patent/DK239988A/da not_active Application Discontinuation
-
1989
- 1989-02-22 JP JP1040459A patent/JPH0249749A/ja active Granted
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