WO1996033701A1 - Inhibiting photodecomposition of 3-substituted-2-oxindoles - Google Patents
Inhibiting photodecomposition of 3-substituted-2-oxindoles Download PDFInfo
- Publication number
- WO1996033701A1 WO1996033701A1 PCT/IB1995/000287 IB9500287W WO9633701A1 WO 1996033701 A1 WO1996033701 A1 WO 1996033701A1 IB 9500287 W IB9500287 W IB 9500287W WO 9633701 A1 WO9633701 A1 WO 9633701A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- red
- yellow
- dye
- lake
- thienyl
- Prior art date
Links
- 0 *C(C(c1cc(*)c(*)cc1N1C(N)=O)C1=O)=O Chemical compound *C(C(c1cc(*)c(*)cc1N1C(N)=O)C1=O)=O 0.000 description 4
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—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
- A61K31/33—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
- A61K31/403—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 condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4883—Capsule finishing, e.g. dyeing, aromatising, polishing
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- This invention relates to the inhibition of photodecomposition of certain 3- substituted-2-oxindole-1-carboxamides of the formula
- X is H, Cl or F
- Y is H or Cl
- R is benzyl or thienyl, each optionally substituted with Cl or F.
- X is H, fluoro, chloro, brorno, (C ⁇ C alkyl, (C 3 -C 7 )cycloalkyl.
- C C 4 alkoxy, (C,-C 4 )alkylthio, trifluoromethyl, (C--C 4 )alkylsulfinyl, (C,-C 4 )alkylsulfonyl, nitro, phenyl, (C 2 -C 4 )alkanoyl, benzoyl, thenoyl, (C 1 -C 4 )alkanamido, benzamido or N,N-dialkylsulfamoyl having 1 to 3 carbons in each of said alkyls;
- Y is, H, fluoro, chloro, bromo, (C,-C 4 )alkyl, (C 3 -C 7 )cycloalkyl, (C,-C 4 )alkoxy, (C,-C 4 )
- R 3 and R 4 are each H, fluoro, chloro, (C,-C 4 )alkyl, (C r C 4 )alkoxy or trifluoromethyl.
- That patent also discloses that said 2-oxindole-1-carboxamides are inhibitors of cyclooxygenase and lipoxygenase, possess analgesic activity in mammals and are useful in treatment of pain and alleviation of symptoms of chronic diseases such as inflammation and pain associated with rheumatoid arthritis and osteoarthritis.
- U.S. Patent 4,556,672 discloses certain 3-acyl substituted- 2-oxindole- 1 -carboxamides of the formula
- X is H, Cl or F
- Y is H or Cl
- R is benzyl or thienyl, each optionally substituted with Cl or F; said photodecomposition resulting from light emanating from a light source which comprises introducing a light absorbing means between said compound and said light source.
- said light absorbing means is a dye selected from the group consisting of yellow #6, red #40, red #3, yellow lake #6, red lake #40 and red lake #3. in a further preferred method of this invention said light absorbing means is yellow #6.
- this invention relates to a tablet comprising a pharmaceutically active ingredient selected from a compound of the formula
- X is H, Cl or F
- Y is H or Cl
- R is benzyl or thienyl, each optionally substituted with Cl or F; said tablet being coated with a coating containing a sufficient amount of yellow dye #6, red dye #40, red dye #3, yellow lake #6, red lake #40 and red lake #3 to inhibit photodecomposition of said pharmaceutically active ingredient.
- this invention comprises a coated tablet wherein said coating contains yellow dye #6 in sufficient amount to inhibit photodecomposition of said pharmaceutically active ingredient.
- this invention comprises a capsule comprising a pharmaceutically active ingredient selected from a compound of the formula
- X is H, Cl or F
- Y is H or Cl
- R is benzyl or thienyl, each optionally substituted with Cl or F; said capsule shell containing a sufficient amount of yellow dye #6, red dye #40, red dye #3, yellow lake #6, red lake #40 and red lake #3 to inhibit photodecomposition of said pharmaceutically active ingredient.
- Light absorbing means means materials which block all or most wave lengths of light such as opaque glass or metals; or materials which absorb light with wave lengths of less than 600 nm such as ultra violet stabilizers or dyes.
- the light absorbing means may be used in packaging materials such as blister packages, sachets or bottles.
- Chemical light absorbing means such as ultraviolet stabilizers may be incorporated in packaging material including blister packages, sachets or bottles or are preferably incorporated in capsule shells or tablet coatings. Chemical light absorbing means may also be mixed directly with the active ingredient prior to tableting or placing in a capsule shell.
- the compounds protected by this invention are acidic and form base salts. All such base salts are within the scope of this invention and can be formed as taught by these patents.
- Such suitable salts include both the organic and inorganic types and include, but are not limited to, the salts formed with ammonia, organic amines, alkali metal hydroxides, alkali metal carbonates, alkali metal bicarbonates, alkali metal hydrides, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth metal carbonates, alkaline earth metal hydrides and alkaline earth metal alkoxides.
- bases which form such base salts include ammonia, primary amines, such as n-propylamine, n-butyiamine, aniline, cyclohexylamine, benzylamine, p-toluidine, ethanolamine and glucamine; secondary amines, such as diethylamine, diethanolamine, N-methylglucamine, N-methylaniline, morpholine, pyrroiidine and piperidine; tertiary amines, such as triethylamine, triethanolamine, N,N-dimethyianiline, N-ethylpiperidine and N-methyimorpholine; hydroxides, such as sodium hydroxide; alkoxides such as sodium ethoxide and potassium methoxide; hydrides such as calcium hydride and sodium hydride; and carbonates such as potassium carbonate and sodium carbonate.
- primary amines such as n-propylamine, n-butyiamine, ani
- Preferred salts are those of sodium, potassium, ammonium, ethanolamine, diethanolamine and triethanolamine. Particularly preferred are the sodium salts.
- the compounds to which this invention is applicable include soivates such as the hemihydrates and monohydrates of the compounds hereinabove described.
- Red and yellow dyes have been found effective in preventing contact of light and the associated light-induced degradation of 3-substituted oxindole-1-carboxamides.
- Preferred dyes are FD&C red #40, FD&C red #3 and FD&C yellow #6. Yellow #6 is especially preferred.
- the dyes are effective in preventing light-induced degradation of 3-substituted-oxindoie-1-carboxamides when mixed with the oxindole, applied to a preformed tablet in a coating, or in a gelatin capsule containing the oxindole.
- the preferred method is the coating of tablets.
- Film coating of pharmaceutical tablets is well known in the art and is described, for example, in United States Patents 4,828,841 ; 3,981 ,948; and 3,802,896 which are hereby incorporated by reference.
- Film coating materials such as white Opadry, Opadry II, Surelease, Aquacoat and Eudragit which are suitable for formulation with the selected dye are commercially available from Colorcon, West Point, PA; FMC Corp., Philadelphia, PA; Rohm Pharma, We ' iterstadt, Germany respectively.
- Dyes may also be formulated into gelatin capsules which are then filled with the oxindole.
- the technology for preparing capsules is well known to those of ordinary skill in this art. Capsules incorporating selected dyes are available commercially from
- 3,784,684 describes the incorporation of opacifers and dyes in gelatine capsule shells.
- the amount of dye in the coating or capsule shell is not critical except that sufficient dye must be incorporated to absorb any incident light. We have found that 1.2-2.8 mgAablet of yellow #6 prevented decomposition while in capsule shells 0.28 to 0.5 mg/capsule afforded light stability.
- a typical formulation of the coated tablets of this invention may be prepared as follows:
- LC assay results for these lots are summarized in the table below. All samples were analyzed in triplicate. Assay values for the uncoated tablets were close to the intended 100 mg/g. Levels of thiophene-2-carboxylic acid, 6-chloro-1H- quinazoline-2,4-dione, thiophene-2-carboxylic acid 1-carbamoyl-5-chloro-2-oxo-2,3- dihydro 1 H-indol-3-yl ester, 6-chloro-2-hydroxy-quinazoline-4-carboxylic acid and unknown #3 for the uncoated tablets increased significantly in the light cabinet (compared to 5°C control). No significant degradation was observed for the tablet cores stored at 5°C, 30°C or 50°C.
- the above ingredients were mixed and a portion roller compacted, then milled and reblended with the remaining ingredients, lubricated and encapsulated in gelatin capsules obtained from Capsugel, a division of Warner-Lambert Company.
- a preferred lubricant is sodium laurel sulfate.
- the capsules contained FD&C yellow dye 0.2651 % of total dry weight in the capsule body and 0.1768% in the cap.
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- Health & Medical Sciences (AREA)
- Chemical & Material 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)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (30)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
UA96041574A UA42739C2 (uk) | 1995-04-24 | 1995-04-24 | Спосіб інгібування фоторозкладу фармацевтично активних сполук, таблетка та капсула, що їх містять |
PCT/IB1995/000287 WO1996033701A1 (en) | 1995-04-24 | 1995-04-24 | Inhibiting photodecomposition of 3-substituted-2-oxindoles |
EP95914494A EP0827399A1 (en) | 1995-04-24 | 1995-04-24 | Inhibiting photodecomposition of 3-substituted-2-oxindoles |
RU96108120A RU2109510C1 (ru) | 1995-04-24 | 1995-04-24 | Способ ингибирования, таблетка и капсула |
JP8532298A JPH10506635A (ja) | 1995-04-24 | 1995-04-24 | 3−置換−2−オキシンドールの光分解阻止 |
SK512-96A SK51296A3 (en) | 1995-04-24 | 1995-04-24 | Inhibiting photodecomposition of 3-substituted-2-oxindol-1- -carboxamides, a tablet and a capsule |
APAP/P/1996/000787A AP607A (en) | 1995-04-24 | 1996-03-07 | Inhibiting photodecomposition of 3-substituted-2-oxindoles. |
ARP960101956A AR002728A1 (es) | 1995-04-24 | 1996-03-28 | Un procedimiento para inhibir la fotodescomposicion de 2-oxindol-1- carboxamidas 3-sustituidas y una composicion farmaceutica que comprende dichaoxindol-carboxamida asi inhibida. |
TR96/00300A TR199600300A2 (tr) | 1995-04-24 | 1996-04-10 | 3-ornatilmis-2-oksindollerin isikla ayrismasinin önlenmesi. |
IL11796996A IL117969A0 (en) | 1995-04-24 | 1996-04-18 | Inhibiting photodecomposition of 3-substituted-2-oxinoles |
SG1996009306A SG64924A1 (en) | 1995-04-24 | 1996-04-19 | Inhibiting photodecompostion of 3-substituted-2- oxindoles |
IS4339A IS4339A (is) | 1995-04-24 | 1996-04-19 | Hömlun ljóssundurliðunar á 3-setnum-2-oxindólum |
RO96-00843A RO113305B1 (ro) | 1995-04-24 | 1996-04-22 | Procedeu de inhibare a descompunerii la lumina a 2-oxindolilor-1-carboxamide-3-substituiti |
CO96019210A CO4700418A1 (es) | 1995-04-24 | 1996-04-22 | Inhibicion de la fotodescomposicion de 2-oxindoles 3-susti- tuidos |
PE1996000275A PE34397A1 (es) | 1995-04-24 | 1996-04-22 | Inhibicion de la fotodescomposicion de 2-oxindoles 3-sustituidos |
CN96105084A CN1053667C (zh) | 1995-04-24 | 1996-04-22 | 抑制3-取代的-2-羟吲哚的光分解 |
KR1019960012356A KR100189585B1 (ko) | 1995-04-24 | 1996-04-23 | 3-치환-2-옥신돌의 광분해 억제 방법 |
HU9601057A HU216544B (hu) | 1995-04-24 | 1996-04-23 | Eljárás 3-helyzetben szubsztituált 2-oxindolok fény hatására történő bomlásának gátlására és a vegyületeket tartalmazó tabletta, kapszula és gyógyszerkészítmény |
NO961622A NO961622L (no) | 1995-04-24 | 1996-04-23 | Inhibering av fotospalting av 3-substituerte 2-oksindoler |
BG100531A BG100531A (en) | 1995-04-24 | 1996-04-23 | Method for inhibition of photodecomposition of 3-substituted 2-oxindoles |
YU25096A YU25096A (sh) | 1995-04-24 | 1996-04-23 | Inhibicija fotodekompozicije 3-supstituisanog-2-oksindola |
AU50851/96A AU692378B2 (en) | 1995-04-24 | 1996-04-23 | Inhibiting photodecomposition of 3-substituted-2-oxindoles |
NZ286432A NZ286432A (en) | 1995-04-24 | 1996-04-23 | Pharmaceutical compositions comprising 3-substituted-2-oxoindole-carboxamide derivatives and method of inhibition by photodecomposition thereof |
ZA9603210A ZA963210B (en) | 1995-04-24 | 1996-04-23 | Inhibiting photodecomposition of 3-substituted-2-oxindoles. |
MA24209A MA23848A1 (fr) | 1995-04-24 | 1996-04-23 | Procede pour inhiber la photodecomposition de 3-substitue-2-oxindoles |
HRPCT/IB95/00287A HRP960194A2 (en) | 1995-04-24 | 1996-04-23 | Inhibiting photodecomposition of 3-substituted-2-oxindoles |
OA60821A OA10286A (en) | 1995-04-24 | 1996-04-24 | Inhibiting photodecomposition of 3-substituted-2-oxindoles |
BR9602024A BR9602024A (pt) | 1995-04-24 | 1996-04-24 | Método para a inibição da fotodecomposição de um composto comprimido e cápsula compreendendo um ingrediente farmaceuticamente ativo |
SI9600133A SI9600133A (en) | 1995-04-24 | 1996-04-24 | Inhibiting photodecomposition of 3-substituted-2-oxindoles |
FI973988A FI973988A (sv) | 1995-04-24 | 1997-10-17 | Förhindrande av ljusförorsakad sönderdelning av 3-substituerade 2-oxindoler |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/IB1995/000287 WO1996033701A1 (en) | 1995-04-24 | 1995-04-24 | Inhibiting photodecomposition of 3-substituted-2-oxindoles |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996033701A1 true WO1996033701A1 (en) | 1996-10-31 |
Family
ID=36997502
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB1995/000287 WO1996033701A1 (en) | 1995-04-24 | 1995-04-24 | Inhibiting photodecomposition of 3-substituted-2-oxindoles |
Country Status (30)
Country | Link |
---|---|
EP (1) | EP0827399A1 (sv) |
JP (1) | JPH10506635A (sv) |
KR (1) | KR100189585B1 (sv) |
CN (1) | CN1053667C (sv) |
AP (1) | AP607A (sv) |
AR (1) | AR002728A1 (sv) |
AU (1) | AU692378B2 (sv) |
BG (1) | BG100531A (sv) |
BR (1) | BR9602024A (sv) |
CO (1) | CO4700418A1 (sv) |
FI (1) | FI973988A (sv) |
HR (1) | HRP960194A2 (sv) |
HU (1) | HU216544B (sv) |
IL (1) | IL117969A0 (sv) |
IS (1) | IS4339A (sv) |
MA (1) | MA23848A1 (sv) |
NO (1) | NO961622L (sv) |
NZ (1) | NZ286432A (sv) |
OA (1) | OA10286A (sv) |
PE (1) | PE34397A1 (sv) |
RO (1) | RO113305B1 (sv) |
RU (1) | RU2109510C1 (sv) |
SG (1) | SG64924A1 (sv) |
SI (1) | SI9600133A (sv) |
SK (1) | SK51296A3 (sv) |
TR (1) | TR199600300A2 (sv) |
UA (1) | UA42739C2 (sv) |
WO (1) | WO1996033701A1 (sv) |
YU (1) | YU25096A (sv) |
ZA (1) | ZA963210B (sv) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11246323B2 (en) | 2017-12-29 | 2022-02-15 | Kraft Foods Group Brands Llc | Oxidative stability of oil-in-water emulsions using natural stabilizers |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2246072A (en) * | 1990-07-20 | 1992-01-22 | Egyt Gyogyszervegyeszeti Gyar | Pharmaceutical compositions stabilised against light |
WO1994007488A1 (en) * | 1992-10-07 | 1994-04-14 | Pfizer Inc. | 3-substituted 2-oxindole-1-carboxamide pharmaceutical compositions |
-
1995
- 1995-04-24 JP JP8532298A patent/JPH10506635A/ja active Pending
- 1995-04-24 SK SK512-96A patent/SK51296A3/sk unknown
- 1995-04-24 EP EP95914494A patent/EP0827399A1/en not_active Ceased
- 1995-04-24 UA UA96041574A patent/UA42739C2/uk unknown
- 1995-04-24 WO PCT/IB1995/000287 patent/WO1996033701A1/en not_active Application Discontinuation
- 1995-04-24 RU RU96108120A patent/RU2109510C1/ru active
-
1996
- 1996-03-07 AP APAP/P/1996/000787A patent/AP607A/en active
- 1996-03-28 AR ARP960101956A patent/AR002728A1/es unknown
- 1996-04-10 TR TR96/00300A patent/TR199600300A2/xx unknown
- 1996-04-18 IL IL11796996A patent/IL117969A0/xx unknown
- 1996-04-19 SG SG1996009306A patent/SG64924A1/en unknown
- 1996-04-19 IS IS4339A patent/IS4339A/is unknown
- 1996-04-22 RO RO96-00843A patent/RO113305B1/ro unknown
- 1996-04-22 PE PE1996000275A patent/PE34397A1/es not_active Application Discontinuation
- 1996-04-22 CN CN96105084A patent/CN1053667C/zh not_active Expired - Fee Related
- 1996-04-22 CO CO96019210A patent/CO4700418A1/es unknown
- 1996-04-23 YU YU25096A patent/YU25096A/sh unknown
- 1996-04-23 KR KR1019960012356A patent/KR100189585B1/ko not_active IP Right Cessation
- 1996-04-23 NO NO961622A patent/NO961622L/no unknown
- 1996-04-23 BG BG100531A patent/BG100531A/xx unknown
- 1996-04-23 ZA ZA9603210A patent/ZA963210B/xx unknown
- 1996-04-23 NZ NZ286432A patent/NZ286432A/en unknown
- 1996-04-23 HR HRPCT/IB95/00287A patent/HRP960194A2/hr not_active Application Discontinuation
- 1996-04-23 AU AU50851/96A patent/AU692378B2/en not_active Ceased
- 1996-04-23 HU HU9601057A patent/HU216544B/hu not_active IP Right Cessation
- 1996-04-23 MA MA24209A patent/MA23848A1/fr unknown
- 1996-04-24 OA OA60821A patent/OA10286A/en unknown
- 1996-04-24 SI SI9600133A patent/SI9600133A/sl not_active IP Right Cessation
- 1996-04-24 BR BR9602024A patent/BR9602024A/pt active Search and Examination
-
1997
- 1997-10-17 FI FI973988A patent/FI973988A/sv unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2246072A (en) * | 1990-07-20 | 1992-01-22 | Egyt Gyogyszervegyeszeti Gyar | Pharmaceutical compositions stabilised against light |
WO1994007488A1 (en) * | 1992-10-07 | 1994-04-14 | Pfizer Inc. | 3-substituted 2-oxindole-1-carboxamide pharmaceutical compositions |
Non-Patent Citations (1)
Title |
---|
P.H. LIST ET AL.: "HAGERS HANDBUCH DER PHARMAZEUTISCHEN PRAXIS 4. EDITION VOL.7 PART A", SPRINGER-VERLAG, BERLIN (DE) * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11246323B2 (en) | 2017-12-29 | 2022-02-15 | Kraft Foods Group Brands Llc | Oxidative stability of oil-in-water emulsions using natural stabilizers |
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