PL438192A1 - Naproxen derivative and method for producing naproxen derivative - Google Patents
Naproxen derivative and method for producing naproxen derivativeInfo
- Publication number
- PL438192A1 PL438192A1 PL438192A PL43819221A PL438192A1 PL 438192 A1 PL438192 A1 PL 438192A1 PL 438192 A PL438192 A PL 438192A PL 43819221 A PL43819221 A PL 43819221A PL 438192 A1 PL438192 A1 PL 438192A1
- Authority
- PL
- Poland
- Prior art keywords
- naproxen
- derivative
- methoxynaphthalen
- amino acid
- producing
- Prior art date
Links
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical class C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 229940024606 amino acid Drugs 0.000 abstract 3
- RVDUTAJUOSJFPW-XFNAGHOKSA-N (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21.C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 RVDUTAJUOSJFPW-XFNAGHOKSA-N 0.000 abstract 2
- 229930182821 L-proline Natural products 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 229960002429 proline Drugs 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- -1 methoxynaphthalen-2-yl Chemical group 0.000 abstract 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- 230000005588 protonation Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/401—Proline; Derivatives thereof, e.g. captopril
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
-
- 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
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem zgłoszenia jest pochodna naproksenu, która charakteryzuje się tym, że ma postać soli organicznej o wzorze, w której kation jest pochodzenia aminokwasowego i stanowi pochodną aminokwasu w postaci estru etylowego, izopropylowego, propylowego i butylowego L-proliny i ma anion (2S)-2-(6-metoksynaftalen-2-ylo)propanianowy Zgłoszenie obejmuje też sposób wytwarzania pochodnej naproksenu, według wynalazku, polegający na reakcji estru alkilowego aminokwasu z kwasem (2S)-2-(6-metoksynaftalen-2-ylo)propanowym w ilości stechiometrycznej, charakteryzuje się tym, że do kwasu metoksynaftalen-2-ylo)propanowego dodaje się ester etylowy, izopropylowy, propylowy lub butylowy L-proliny, a reakcję protonowania estru kwasem prowadzi się w środowisku bezrozpuszczalnikowym w temperaturze pokojowej, w czasie 5 - 45 minut.The subject of the application is a derivative of naproxen, which is characterized in that it is in the form of an organic salt of the formula in which the cation is of amino acid origin and is derived from the amino acid L-proline ethyl, isopropyl, propyl and butyl esters and has the anion (2S)-2 -(6-methoxynaphthalen-2-yl)propanoic acid The application also covers a method for producing a naproxen derivative according to the invention, consisting in the reaction of an amino acid alkyl ester with (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid in a stoichiometric amount, characterized in that L-proline ethyl, isopropyl, propyl or butyl ester is added to the methoxynaphthalen-2-yl)propanoic acid, and the reaction of protonation of the ester with the acid is carried out in a solvent-free environment at room temperature for 5 - 45 minutes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL438192A PL438192A1 (en) | 2021-06-18 | 2021-06-18 | Naproxen derivative and method for producing naproxen derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL438192A PL438192A1 (en) | 2021-06-18 | 2021-06-18 | Naproxen derivative and method for producing naproxen derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL438192A1 true PL438192A1 (en) | 2022-12-19 |
Family
ID=84487965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL438192A PL438192A1 (en) | 2021-06-18 | 2021-06-18 | Naproxen derivative and method for producing naproxen derivative |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL438192A1 (en) |
-
2021
- 2021-06-18 PL PL438192A patent/PL438192A1/en unknown
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