DK150604B - Analogifremgangsmaade til fremstilling af calciumoxaprozin - Google Patents
Analogifremgangsmaade til fremstilling af calciumoxaprozin Download PDFInfo
- Publication number
- DK150604B DK150604B DK183582A DK183582A DK150604B DK 150604 B DK150604 B DK 150604B DK 183582 A DK183582 A DK 183582A DK 183582 A DK183582 A DK 183582A DK 150604 B DK150604 B DK 150604B
- Authority
- DK
- Denmark
- Prior art keywords
- calcium
- oxaprozin
- oxaprozine
- salt
- preparing calcium
- Prior art date
Links
- OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 title abstract description 23
- 239000011575 calcium Substances 0.000 title abstract description 13
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title abstract description 12
- 229910052791 calcium Inorganic materials 0.000 title abstract description 12
- 238000000034 method Methods 0.000 title description 4
- 229960002739 oxaprozin Drugs 0.000 abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 5
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 229960005069 calcium Drugs 0.000 description 9
- -1 4,5-diphenyloxazol-2-yl Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019658 bitter taste Nutrition 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960002713 calcium chloride Drugs 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007910 chewable tablet Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 150000004685 tetrahydrates Chemical class 0.000 description 2
- CBOCVOKPQGJKKJ-UHFFFAOYSA-L Calcium formate Chemical compound [Ca+2].[O-]C=O.[O-]C=O CBOCVOKPQGJKKJ-UHFFFAOYSA-L 0.000 description 1
- BCZXFFBUYPCTSJ-UHFFFAOYSA-L Calcium propionate Chemical compound [Ca+2].CCC([O-])=O.CCC([O-])=O BCZXFFBUYPCTSJ-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 1
- 229940052299 calcium chloride dihydrate Drugs 0.000 description 1
- 229940044172 calcium formate Drugs 0.000 description 1
- 235000019255 calcium formate Nutrition 0.000 description 1
- 239000004281 calcium formate Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004442 gravimetric analysis Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 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 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicinal Preparation (AREA)
- Plural Heterocyclic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
o χ 150SG4
Den foreliggende opfindelse angår en analogifremgangs-måde til fremstilling af dét hidtil ukendte calciumoxaprozin.
Oxaprozin, nemlig 3“(4,5-diphenyloxazol-2-yl)propion-syre har vist interessant antiinflammatorisk aktivitet og 5 er for tiden ved at undergå kliniske forsøg ved afprøvning på mennesker som antiinflammatorisk middel.
Uheldigvis har oxaprozin en meget bitter smag. Dette kan maskeres i brug ved at lave doseringsformerne som kapsler eller filmovertrukne tabletter. Hvor der imidlertid kræves 10 meget store enkeltdoser af oxaprozin, er denne løsning på problemet ikke. tilfredsstillende. Forsøg er derfor gennemført for at finde frem til farmaceutiske præparater, der tillader heldagsdosering på én gang. Sådanne præparater indbefatter tyggetabletter indeholdende en forholdsvis stor mængde oxaprozin 15 og suspensioner. Oxaprozins bitre smag har vist sig at være en ulempe hos sådanne præparater.
Der er nu fremstillet forskellige salte af oxaprozin, hvoraf ét ved den herved foretagne forskning har vist sig at overvinde ovenstående mangler, idet det er konstateret, at 20 calciumsaltet ikke har stamsyrens bitterhed. Derimod er oxaprozins natriumsalt på den anden side ganske bittert.
Ifølge den foreliggende opfindelse tilvejebringes derfor en fremgangsmåde til fremstilling af calciumoxaprozin, dvs. calciumsaltet af 3-(4,5-diphenyloxazol-2-yl)propionsyre, hvil-25 ken fremgangsmåde er ejendommelig ved, at oxaprozin, fortrinsvis i form af et vandopløseligt salt, navnlig et alkalimetalsalt, behandles med en kilde til calciumioner, især calcium-chlorid, fortrinsvis ved at omsættes i vandig opløsning.
Det vandopløselige salt kan ud over et alkalimetalsalt, 30 f.eks. natrium- eller kaliumsaltet, være et ammoniumsalt eller et aminsalt. Kilden til calciumioner kan ud over calciumchlo-rid f.eks. være calciumnitrat, calciumacetat eller calcium-formiat i vandig opløsning.
Betegnelsen calciumoxaprozin omfatter alle former af calciumoxaprozin, inklusive tetrahydratet, som fremkommer under visse omstændigheder.
o 150604
Det her omhandlede calciumoxaprozin kan anvendes i et velsmagende farmaceutisk præparat til oral indgivelse, hvilket præparat foruden calciumoxaprozin indeholder en farmaceutisk bærer.
5 De farmaceutiske præparater indbefatter faste og fly dende sammensætninger. En hvilken som helst hensigtsmæssig bærer, som er kendt inden for teknikken, kan anvendes i det farmaceutiske middel. I et sådant middel er bæreren almindeligvis fast eller flydende eller foreligger som en blanding 10 af et fast eller flydende bærestof.
Fortrinsvis foreligger den farmaceutiske sammensætning i enhedsdoseringsform såsom tabletter eller kapsler. I en sådan form er midlet underinddelt i enhedsdoser indeholdende passende mængder af den aktive bestanddel. Mængden af aktiv 15 bestanddel i en enhedsdosisform kan varieres eller indstilles fra 100 mg eller mindre til 800 mg eller mere, alt i overensstemmelse med det særlige behov. Fortrinsvis er calciumoxaprozin til stede i en mængde fra 200 til 750 mg, men især fra 400 til 750 mg.
20
Eksempel β-(4,5-diphenyioxazol-2-yl)propionsyrecalciumsalt β-(4,5-diphenyloxazol-2-yl)propionsyre ("oxaprozin") omdannes til sit natriumsalt ved at omrøre syren (6 kg) i 25 60 kg destilleret vand og 1,85 kg 46 til 48%'s flydende na triumhydroxid. En filtreret opløsning af 2,44 kg calcium-chlorid-dihydrat B.P. (British Pharmacopeia) i destilleret vand tilsættes, og den i overskriften anførte forbindelse fældes som et hvidt fast stof. Dette indsamles på vakuumfilter 30 og vaskes med destilleret vand, indtil filtratet er chlorid-frit. Produktet tørres i luftovn, hvilket giver et udbytte på 6,7 kg (98% af det teoretiske) af den i overskriften anførte forbindelse som tetrahydrat.
35
3 1506 0A
o
Analyse, beregnet for (^8^4^3^ 2 Ca, 41^0: C = 62,0%, H = 5,17%, N = 4,02% fundet: C = 61,48%, H = 5,02%, N = 3,67%. Calciumindholdet er ved gravimetrisk analyse bestemt 5 til 6,4% (teoretisk calciumindhold 5,75%).
Forsøg
Calciumsaltet fra eksempel 1 bringes på præparatform som tyggetabletter. Disse viser sig at være ganske velsmagen-10 de i modsætning til lignende oxaprozintabletter, der er så bitre, at de faktisk ikke er til at holde ud at have i munden.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8113074 | 1981-04-28 | ||
| GB8113074 | 1981-04-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK183582A DK183582A (da) | 1982-10-29 |
| DK150604B true DK150604B (da) | 1987-04-13 |
| DK150604C DK150604C (da) | 1987-12-07 |
Family
ID=10521427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK183582A DK150604C (da) | 1981-04-28 | 1982-04-23 | Analogifremgangsmaade til fremstilling af calciumoxaprozin |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US4465838A (da) |
| EP (1) | EP0063884B1 (da) |
| JP (1) | JPS57181072A (da) |
| KR (1) | KR880000871B1 (da) |
| AT (1) | ATE14015T1 (da) |
| AU (1) | AU544975B2 (da) |
| CA (1) | CA1169867A (da) |
| CS (1) | CS236674B2 (da) |
| DD (1) | DD202017A5 (da) |
| DE (1) | DE3264400D1 (da) |
| DK (1) | DK150604C (da) |
| ES (1) | ES8307230A1 (da) |
| FI (1) | FI71314C (da) |
| GR (1) | GR75913B (da) |
| HU (1) | HU185276B (da) |
| IE (1) | IE52909B1 (da) |
| IL (1) | IL65443A (da) |
| MY (1) | MY8700599A (da) |
| NZ (1) | NZ200247A (da) |
| PH (1) | PH18053A (da) |
| PL (1) | PL136322B1 (da) |
| PT (1) | PT74794B (da) |
| ZA (1) | ZA822355B (da) |
| ZW (1) | ZW7482A1 (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5380738A (en) * | 1993-05-21 | 1995-01-10 | Monsanto Company | 2-substituted oxazoles further substituted by 4-fluorophenyl and 4-methylsulfonylphenyl as antiinflammatory agents |
| US6726928B2 (en) * | 1994-10-28 | 2004-04-27 | R.P. Scherer Technologies, Inc. | Process for preparing solid dosage forms for unpalatable pharmaceuticals |
| NZ332861A (en) * | 1996-05-20 | 2000-08-25 | G | Potassium, sodium and tris oxaprozin salt pharmaceutical formulations |
| US7358254B2 (en) * | 2001-07-13 | 2008-04-15 | Bristol-Myers Squibb Company | Method for treating atherosclerosis employing an aP2 inhibitor and combination |
| PE20061303A1 (es) * | 2005-03-30 | 2006-12-07 | Astion Dev As | Composicion farmaceutica que comprende oxaprozina |
| AU2006228869A1 (en) * | 2005-03-30 | 2006-10-05 | Astion Pharma A/S | Oxaprozin or a closely related compound for the treatment of eczema |
| PL2340296T3 (pl) * | 2008-08-26 | 2015-03-31 | Dorf Ketal Chemicals I Private Ltd | Nowy dodatek do hamowania korozji kwasowej i sposób stosowania nowego dodatku |
| KR20140065862A (ko) * | 2012-11-22 | 2014-05-30 | 에스케이케미칼주식회사 | 발포성 속붕해성 이매티닙 제제 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1206403A (en) * | 1966-12-15 | 1970-09-23 | Wyeth John & Brother Ltd | Oxazoles |
| GB1245087A (en) * | 1967-10-26 | 1971-09-02 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| US3578671A (en) * | 1967-11-06 | 1971-05-11 | Wyeth John & Brother Ltd | Oxazoles |
-
1982
- 1982-03-31 IE IE766/82A patent/IE52909B1/en not_active IP Right Cessation
- 1982-04-05 ZA ZA822355A patent/ZA822355B/xx unknown
- 1982-04-05 CA CA000400464A patent/CA1169867A/en not_active Expired
- 1982-04-06 NZ NZ200247A patent/NZ200247A/en unknown
- 1982-04-06 IL IL65443A patent/IL65443A/xx not_active IP Right Cessation
- 1982-04-06 AU AU82378/82A patent/AU544975B2/en not_active Expired
- 1982-04-07 EP EP82301839A patent/EP0063884B1/en not_active Expired
- 1982-04-07 AT AT82301839T patent/ATE14015T1/de not_active IP Right Cessation
- 1982-04-07 DE DE8282301839T patent/DE3264400D1/de not_active Expired
- 1982-04-09 GR GR67879A patent/GR75913B/el unknown
- 1982-04-15 FI FI821324A patent/FI71314C/fi not_active IP Right Cessation
- 1982-04-15 ZW ZW74/82A patent/ZW7482A1/xx unknown
- 1982-04-22 PH PH27171A patent/PH18053A/en unknown
- 1982-04-23 DK DK183582A patent/DK150604C/da not_active IP Right Cessation
- 1982-04-23 JP JP57069463A patent/JPS57181072A/ja active Granted
- 1982-04-26 PL PL1982236145A patent/PL136322B1/pl unknown
- 1982-04-26 PT PT74794A patent/PT74794B/pt unknown
- 1982-04-26 KR KR8201829A patent/KR880000871B1/ko not_active Expired
- 1982-04-26 US US06/371,904 patent/US4465838A/en not_active Expired - Lifetime
- 1982-04-27 ES ES511730A patent/ES8307230A1/es not_active Expired
- 1982-04-27 HU HU821325A patent/HU185276B/hu unknown
- 1982-04-27 DD DD82239350A patent/DD202017A5/de not_active IP Right Cessation
- 1982-04-28 CS CS823052A patent/CS236674B2/cs unknown
-
1984
- 1984-07-11 US US06/629,704 patent/US4532253A/en not_active Expired - Lifetime
-
1987
- 1987-12-30 MY MY599/87A patent/MY8700599A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |