GB2120935A - Fat-soluble vitamin preparation - Google Patents

Fat-soluble vitamin preparation Download PDF

Info

Publication number
GB2120935A
GB2120935A GB08307543A GB8307543A GB2120935A GB 2120935 A GB2120935 A GB 2120935A GB 08307543 A GB08307543 A GB 08307543A GB 8307543 A GB8307543 A GB 8307543A GB 2120935 A GB2120935 A GB 2120935A
Authority
GB
United Kingdom
Prior art keywords
vitamin
ester
soluble
oil
fat
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
GB08307543A
Other versions
GB8307543D0 (en
GB2120935B (en
Inventor
Yoshinori Yamamoto
Taizo Okada
Shigeo Morioka
Tsutomu Kaneko
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sato Pharmaceutical Co Ltd
Original Assignee
Sato Pharmaceutical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sato Pharmaceutical Co Ltd filed Critical Sato Pharmaceutical Co Ltd
Publication of GB8307543D0 publication Critical patent/GB8307543D0/en
Publication of GB2120935A publication Critical patent/GB2120935A/en
Application granted granted Critical
Publication of GB2120935B publication Critical patent/GB2120935B/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Nutrition Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

An oil-soluble composition contains fat-soluble vitamin B2 butyrate with an oily solubilizing agent comprising a glycerin ester of a fatty acid, a sorbitan ester of a fatty acid, a polyoxyethylenesorbitan ester of a fatty acid, or a mixture of these esters. The vitamin is present in an amount of up to 25% by weight of the composition. The oil-soluble composition can be formulated in soft, hard or micro capsules.

Description

SPECIFICATION Oil-soluble composition containing fat-soluble vitamin This invention relates to an oil-soluble composition containing a fat-soluble vitamin with prolonged clearness and stability, and more particularlyto an oil-soluble composition containing a fat-soluble vitamin, which comprises up to 25% by weight of vitamin B2 butyrate and at least one of glycerin esters of fatty acid, sorbitan esters of fatty acid and polyoxyethylenesorbitan esters of fatty acid as an oily solubilizing agent.
Vitamin B2 butyrate ester as a fat-soluble vitamin has been recently regarded as being clinically important in lowering peroxide lipids and improving abnormal HDL-C and LDL values of blood, etc.
Heretofore, vitamin B2 butyrate has been used in a powdery form as prepared into tablets, granules, or powder, or in an aqueous solution form or in an oil suspension form. An oil-soluble composition containing a small content, for example, up to about 1% by weight, of vitamin B2 bytyrate has been used in medicine, food, etc., but it has been difficult to prepare an oil-soluble composition with a high content, good clearness and good stability.
The present invention provides an oil-soluble composition containing a fat-soluble vitamin free from the above-mentioned disadvanages, where up to 25% by weight of vitamin B2 butyrate is contained.
According to the present invention, an oil-soluble composition containing a fat-soluble vitamin is provided, which composing, in vitamin B2 butyrate, as an oily solubilizing agent a glycerin mono-ester or a mixture of glycerin mono- and di- and/or tri-ester of fatty acid having 4 to 18 carbon atoms; a sorbitan mono-ester or a mixture of sorbitan mono- and di- and/or tri-ester of fatty acid having 12 to 18 carbon atoms; and polyoxyethylenesorbitan mono-ester or a mixture of polyoxyethylenesorbitan mono-, di- and/or tri-ester of fatty acid having 12 to 18 carbon atoms; or a mixture of said esters. The POE number of polyoxyethylenesorbitan ester of fatty acid is 2 to 30; and the vitamin B2 butyrate being contained up to 25% by weight, on the basis of the total composition.
According to the present invention, an oil-soluble composition with good stability containing up to 25% by weight of vitamin B2 butyrate therein can be obtained, which can be preserved stably for a long time without any turbidity and any deposition of crystals.
As the oily solubilizing agent for combining with the vitamin B2 butyrate according to the present invention, the followings are enumerated.
(1) glycerin mono-ester or the mixture of glycerin mono- and di- and/or tri-ester of fatty acid having 4 to 18, preferably 6 to 12 carbon atoms, in which preferably at least 40% by weight of mono-ester of fatty acid is included.
(2) sorbitan mono-ester or the mixture of sorbitan mono- and di- and/or tri-ester of fatty acid having 12 to 18, in which preferably at least 40% by weight of mono-ester of fatty acid is included, (3) polyoxyethylenesorbitan mono-ester or the mixture of polyoxyethylenesorbitan mono- and di- and/or tri-ester of fatty acid having 12 to 1-8, preferably 18 carbon atoms, in which POE number is 2 to 30, preferably 20 and preferably at least 40% by weight of mono-ester of fatty acid is included, and (4) the mixture thereof.
The oil-soluble composition according to the present invention can contain up to 25% by weight of vitamin B2 butyrate by using at least one of specific glycerin esters of fatty acid, sorbitan esters of fatty acid and polyoxyethylenesorbitan esters of fatty acid in contrast to the conventional low content, for example, up to 1% by weight. According to the present invention an unexpected prolonged clearness and stability even with such a high content can be attained.
Above 25% by weight of vitamin B2 butyrate, it is difficult to prepare the oil-soluble composition, and above 30% by weight, its preparation is impossible.
The oil-soluble composition of the present invention can be combined with such fat-soluble vitamin as vitamin A, vitamin E, vitamin D, etc., and such vegetable oils as rice oil, wheat germ oil, soybean oil, cotton seed oil, rapeseed oil, peanut oil, etc., as occasion demands.
The present oil-soluble composition containing vitamin B2 butyrate or further containing therein the other fat-soluble vitamins or vegetable oils can be used as prepared into soft capsules, hard capsules, or microcapsules.
The present invention will be described in detail below, referring to Examples which is not limitative of the present invention.
Example 1 According to the present invention, oil-soluble compositions were prepared by mixing 2, 10 and 25% by weight of vitamin B2 butyrate with 98, 90 and 75% by weight of oil-solubilizing agents (A) - (G) given below, respectively, and the turbidity of the compositions was measured by Poic integrating sphere-type turbidimeter with their respective filtration-purified single oil-solubilizing agents as control to investigate the clearness.
(A) sorbitan ester of lauric acid (monoester content: about 60%) 100% (B) sorbitan ester of oleic acid. POE (20) (monoester content: about 80%) 100% (C) glycerin ester of of caprylic acid (monoester content: about 55%) 100n/ (D) sorbitan ester of oleic acid. POE (20) (monoester content: about 80%) 10% sorbitan ester of oleic acid (monoester content about 90%) 90% (E) sorbitan ester of stearic acid. POE (20) (monoester content: about 40%) 10% glycerin ester of oleic acid (monoester content: about 40%) 90% (F) glycerin ester of caprylic acid (monoester content: about 95%) 92% sorbitan ester of lauric acid (monoester content: about 60%) 8% (G) sorbitan ester of lauric acid (monoester content: about 60%) 8% sorbitan ester of oleic acid.POE (20) (monoester content: about 90%) 7% glycerin ester of caproic acid (monoester content: about 60%) 85% Results of measurements of the individual samples were given in Table 1.
TABLE 1 (unit: ppm) Sample Present Composition Example 1 Measurement (A) (B) (C) (D) (E) (F) (G) Right after preparation 0.001 0.002 0.000 0.003 0.003 0.001 0.002 3 months after preparation, 25 C 0.004 0.005 0.002 0.007 0.010 0.004 0.004 3 years after preparation, 25 C 0.029 0.037 0.019 0.041 0.051 0.021 0.023 2 weeks after prepartion, 25 C, 91% RH 0.029 0.035 0.017 0.046 0.049 0.025 0.025 2 months after preparation, 25 C, 91% RH 0.039 0.046 0.035 0.053 0.065 0.040 0.038 Composition Vitamin B2 butyrate: 2 wt. % oily solubilizing agent:: 98 wt. % Right after preparation 0.002 0.003 0.000 0.004 0.004 0.002 0.001 3 months after preparation, 25 C 0.010 0.010 0.003 0.010 0.011 0.009 0.007 3 years after preparation, 25 C 0.028 0.039 0.019 0.043 0.053 0.024 0.029 2 weeks after preparation, 25 C, 91% RH 0.030 0.036 0.026 0.044 0.049 0.030 0.038 2 months after preparation, 25 C, 91% RH 0.045 0.048 0.039 0.067 0.068 0.051 0.061 Composition Vitamin B2 butyrate: 10 wt. % oily solubilizing agent: 90 wt. % Right after preparation 0.003 0.005 0.000 0.006 0.006 0.006 0.004 3 months after preparation, 25 C 0.015 0.014 0.009 0.016 0.017 0.016 0.015 3 years after preparation, 25 C 0.040 0.042 0.024 0.049 0.060 0.027 0.034 2 weeks after preparation, 25 C, 91% RH 0.059 0.067 0.051 0.075 0.084 0.063 0.066 2 months after preparation, 25 C, 91% RH 0.108 0.113 0.077 1.008 1.011 0.079 0.084 Composition Vitamin B2 butyrate: : 25 wt. % oily solubilizing agent: 75 wt. % Example 2 According to the present invention, further oil-soluble compositions were prepared by mixing 2, 10, and 25% by weight of vitamin B2 butyrate with 50,45 and 45% by weight of oily solubilizing agents (H) - (N) given below and 48,45, and 30% by weight in total of vegetable oil and other soluble vitamin (H) - (N) given below, respectively and the tubidity of the respective compositions was measured in the same manner as in Example 1 to investigate the clearness.
(H) sorbitan ester of oleic acid (monoester content: about 90%) 60% vegetable oil 20% fat-soluble vitamin 20% (I) sorbitan ester of oleic acid. POE (20) (monoester content: about 80%) 60% vegetable oil 20% fat-soluble vitamin 20% (J) glycerin ester of caprylic acid (monoester content: about 55%) 60% vegetable oil 20% fat-soluble viamin 20% (K) sorbitan ester of oleic acid.POE (20) (monoester content: about 80%) 7% sorbitan ester of lauric acid (monoester content: about 60%) 53% vegetable oil 20% fat-soluble vitamin 20% (L) sorbitan ester of stearic acid; POE (20) (monoester content: about 40%) 7% glycerin ester of oleic acid (monoester content: about 40%) 53% vegetable oil 20% fat-soluble vitamin 20% (M) sorbitan ester of oleic acid (monoester content: about 90%) 10% glycerin ester of caprylic acid (monoester content: about 55%) 50% vegetable oil 20% fat-soluble vitamin 20% (N) sorbitan ester of stearic acid (monoester content: about 50%) 8% sorbitan ester of oleic aicd. POE (20) (monoester content: about 90%) 7% glycerin ester of caprylic acid (monoester content: about 60%) 45% vegetable oil 20% fat-soluble vitamin 20% (as the vegetable oil were used rapeseed oil, wheat germ oil, etc. and as the fat-soluble vitamin were used vitamin A, vitamin E, etc.) Results of measurement of the individual samples were given in Table 2.
TABLE 2 (unit: ppm) Sample Present Composition Example 1 Measurement (H) (I) (J) (K) (L) (M) (N) Right after preparation 0.003 0.003 0.000 0.003 0.002 0.003 0.003 3 months after preparation, 25 C 0.009 0.010 0.001 0.010 0.005 0.005 0.006 3 years after preparation, 25 C 0.050 0.052 0.019 0.058 0.027 0.029 0.025 2 weeks after preparation, 25 C, 91% RH 0.042 0.051 0.017 0.057 0.026 0.033 0.028 2 months after preparation, 25 C, 91% RH 0.055 0.058 0.036 0.059 0.044 0.049 0.036 Composition Vitamin B2 butyrate: 2 wt. % Total of vegetable oil and fat-soluble vitamin 48 wt. % and oily solubilizing agent:: 50 wt. % Right after preparation 0.004 0.005 0.000 0.005 0.003 0.003 0.002 3 months after preparation, 25 C 0.011 0.014 0.003 0.017 0.015 0.016 0.010 3 years after preparation, 25 C 0.055 0.060 0.019 0.060 0.029 0.029 0.027 2 weeks after preparation, 25 C, 91% RH 0.045 0.055 0.027 0.055 0.030 0.031 0.030 2 months after preparation, 25 C, 91% RH 0.068 0.072 0.039 0.074 0.062 0.060 0.049 Composition Vitamin B2 butyrate: 10 wt. % Total of vegetable oil and fat-soluble vitamin 45 wt. % and oily solubilizing agent: 45 wt. % TABLE 2 (unit: ppm) Sample Present Composition Example 1 Measurement (H) (I) (J) (K) (L) (M) (N) Right after preparation 0.006 0.008 0.009 0.005 0.005 0.005 0.003 3 months after preparation, 25 C 0.018 0.021 0.011 0.025 0.018 0.019 0.016 3 years after preparation, 25 C 0.062 0.073 0.026 0.075 0.035 0.039 0.033 2 weeks after preparation, 25 C, 91% RH 0.092 0.098 0.054 0.115 0.065 0.074 0.068 2 months after preparation, 25 C, 91% RH 1.009 1.034 0.078 1.035 0.092 0.096 0.082 Composition Vitamin B2 butyrate: 25 wt. % Total of vegetable oil and fat-soluble vitamin 30 wt. % and oily solubilizing agent:: 45 wt. % Comparative Example In contrast to the present oil-soluble compositions, the following compositions (0) - (Z) were prepared by mixing 2 and 10% by weight of vitamin B2 butyrate with 98 and 90% by weight of single vegetable oil or a mixture of vegetable oil and fat-soluble vitamin, respectively, and the turbidity of the individual compositions was measured in the same manner as in Example 1 to investigate the clearness.
(O) Rapeseed oil 100% (P) Wheat germ oil 100% (Q) Soybean oil 100% (R) Rapeseed oil 60% fat-soluble vitamin 40% (S) Peanut oil 60% fat-soluble vitamin 40% (T) Wheat germ oil 60% fat-soluble vitamin 40% (as the fat-soluble vitamin were used vitamin A, vitamin E, etc.).
Results of measurement of the individual samples are given in Table 3.
TABLE 3 (unit: ppm) Sample Comparative Example Measurement (O) (P) (Q) (R) (S) (T) Right after preparation 14.19 14.67 16.03 14.19 14.01 16.15 3 months after preparation, 25 C 47.29 59.64 72.08 47.30 55.37 80.48 3 years after prepration, 25 C 536.0 731.0 1036.2 506.3 531.1 1133.3 2 weeks after preparation, 25 C, 91% RH - - - - - 2 months after preparation, 25 C, 91% RH - - - - - Composition Vitamin B2 butyrate: 2 wt. % Total of vegetable oil and fat-soluble vitamin 98 wt. % or vegetable oil 98 wt. % Right after preparation 2610.0 2800.0 2840.0 2010.0 2210.0 2300.0 3 months after preparation, 25 C - - - - - 3 years after preparation, 25 C - - - - - 2 weeks after preparation, 25 C, 91% RH - - - - - 2 months after preparation, 25 C, 91% RH - - - - - Composition Vitamin B2 butyrate:: 10 wt. % Total of vegetable oil and fat-soluble vitamin 90 wt. % or vegetable oil 90 et. % Results of Examples 1 and 2 and Comparative Example, that is, the results shown in Tables 1,2 and 3 are summarized as follows: (1) In the case of mixing 2% by weight of vitamin B2 butyrate, the turbidity of the individual compositions (A) -(G) and (H) - (N) according to the present invention is much lower than that of the individual compositions (O) - (T) of comparative Example, i.e. Table 3 right after the preparation, and thus the clearness is much better.
After preservation for 3 months at 250C and for 3 years at 250C, the individual compositions according to the present invention have no difference in the clearness, whereas in comparative Example, the clearness was greatly lowered in accordance with the preservation time.
(2) In the case of mixing 10% by weight of vitamin B2 butyrate, there is no substantial difference in clearness from the case of mixing 2% by weight of vitamin B2 butyrate in all the compositions (A) - (G) and (H)- (N) right after the preparation and with time after the preparation, whereas in comparative Example (O) (T), the turbidity is considerably increased, as compared with the case of mixing 2% by weight of vitamin B2 butyrate and thus the clearness is considerably lowered.
(3) In the case of mixture 25% by weight of vitamin B2 butyrate the clearness in (A) - (G) and (H) - (N) are little lowered than that in the case of mixing 10% by weight of vitamin B2 butyrate right after the preparation and with time after the preparation, but is very distinguished, when compared with Comparative Example of mixing 2% by weight of vitamin B2 butyrate. In Comparative Example, the measurement is practially impossible.
As described above, the present oil-soluble composition containing fat-soluble vitamin has good clearness even with the maximum content of 25% by weight and the clearness is not substantially lowered and very stable even if preserved for a long time, as shown in Examples.

Claims (4)

1. An oil-soluble composition containing a fat-soluble vitamin characterized by composing, in vitamin B2 butyrate, as an oily solubilizing agent a a glycerin mono-ester or a mixture of glycerin mono- and di- and/or tri-ester of a fatty acid having 4 to 18 carbon atoms; a sobitan mono-ester or a mixture of sorbitan mono- and di- and/or tri-ester of a fatty acid having 12 to 18 carbon atoms; a polyoxyethylenesorbitan mono-ester or a mixture of polyoxyethylenesorbitan mono- and di- and/or tri-ester of a fatty acid having 12 to 18 carbon atoms, each POE number of the esters being 2 to 30; or a mixture of said esters, and therein a maximum composition ratio of said vitamin B2 butyrate is 25% by weight.
2. An oil-soluble composition containing a fat-soluble vitamin as claimed in Claim 1, in which the number of the carbon atoms of the fatty acid in glycerin ester of fatty acid is 6 to 12.
3. An oil-soluble composition containing a fat-soluble vitamin as claimed in Claim 1, in which POE number of poiyoxyethylenesorbitan ester of fatty acid is 20 and the number of the carbon atoms of the fatty acid in polyoxyethylenesorbitan ester of fatty acid is 18.
4. An oil-soluble composition containing a fat-soluble vitamin substantially as hereinbefore described in any of the Examples.
GB08307543A 1982-05-31 1983-03-18 Fat-soluble vitamin preparation Expired GB2120935B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP57091466A JPS58208215A (en) 1982-05-31 1982-05-31 Oil-soluble composition containing fat-soluble vitamin

Publications (3)

Publication Number Publication Date
GB8307543D0 GB8307543D0 (en) 1983-04-27
GB2120935A true GB2120935A (en) 1983-12-14
GB2120935B GB2120935B (en) 1985-10-23

Family

ID=14027151

Family Applications (1)

Application Number Title Priority Date Filing Date
GB08307543A Expired GB2120935B (en) 1982-05-31 1983-03-18 Fat-soluble vitamin preparation

Country Status (6)

Country Link
JP (1) JPS58208215A (en)
CH (1) CH656531A5 (en)
DE (1) DE3311008C2 (en)
FR (1) FR2527440B1 (en)
GB (1) GB2120935B (en)
SE (1) SE461892B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5759997A (en) * 1984-07-24 1998-06-02 Novartis Ag Cyclosporin galenic forms
US6475519B1 (en) 1997-01-30 2002-11-05 Novartis Ag Oil-free pharmaceutical compositions containing cyclosporin A
US7081445B2 (en) 1989-02-20 2006-07-25 Novartis Ag Cyclosporin galenic forms

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63130535A (en) * 1986-11-19 1988-06-02 Nisshin Kagaku Kk Antihistamine agent for oral administration
GB9325445D0 (en) 1993-12-13 1994-02-16 Cortecs Ltd Pharmaceutical formulations

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR8014M (en) * 1968-01-09 1970-07-27
US3962436A (en) * 1969-06-03 1976-06-08 Sumitomo Chemical Company, Limited Pharmaceutical compositions having controlled rate of gastro-intestinal absorption
NL7012460A (en) * 1970-08-22 1972-02-24
US3932634A (en) * 1973-06-28 1976-01-13 Pfizer Inc. High potency vitamin water dispersible formulations

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5759997A (en) * 1984-07-24 1998-06-02 Novartis Ag Cyclosporin galenic forms
US5977066A (en) * 1984-07-24 1999-11-02 Novartis Ag Cyclosporin galenic forms
US6306825B1 (en) 1984-07-24 2001-10-23 Novartis Ag Cyclosporin galenic forms
US6468968B2 (en) 1984-07-24 2002-10-22 Novartis Ag Cyclosporin galenic forms
US7081445B2 (en) 1989-02-20 2006-07-25 Novartis Ag Cyclosporin galenic forms
US7511014B2 (en) 1989-02-20 2009-03-31 Novartis Ag Cyclosporin galenic forms
US6475519B1 (en) 1997-01-30 2002-11-05 Novartis Ag Oil-free pharmaceutical compositions containing cyclosporin A
US6723339B2 (en) 1997-01-30 2004-04-20 Novartis Ag Oil-free pharmaceutical compositions containing cyclosporin A

Also Published As

Publication number Publication date
SE8301565L (en) 1983-12-01
SE8301565D0 (en) 1983-03-22
GB8307543D0 (en) 1983-04-27
JPS58208215A (en) 1983-12-03
JPH044299B2 (en) 1992-01-27
FR2527440B1 (en) 1987-05-15
CH656531A5 (en) 1986-07-15
DE3311008C2 (en) 1986-04-10
GB2120935B (en) 1985-10-23
FR2527440A1 (en) 1983-12-02
DE3311008A1 (en) 1983-12-01
SE461892B (en) 1990-04-09

Similar Documents

Publication Publication Date Title
EP0229652B1 (en) Stabilized tocopherol in dry, particulate, free-flowing form
DK173318B1 (en) Synergic antioxidant blend
US5077069A (en) Composition of natural antioxidants for the stabilization of polyunsaturated oils
CA2068028C (en) Liposoluble antioxidant mixture
CA2734477C (en) Antioxidant composition for marine oils comprising tocopherol, rosemary extract, ascorbic acid and green tea extract, said green tea extract comprising a polysaccharide carrier
US5310734A (en) Phospholipid composition
US5438044A (en) Phospholipid composition
US2935449A (en) Stabilized vitamin a compositions
GB2120935A (en) Fat-soluble vitamin preparation
US3012888A (en) Method for preparing a granular oilfree phosphatide product
NO301651B1 (en) Approach. for the protection of a fat, food, cosmetic or pharmaceutical product content. a fatty substance against oxidation, fat, cosmetic, animal fat and vegetable oil, and of coenzyme Q as an antioxidant
Earle et al. Essential fatty acids in the diet of the boll weevil, Anthonomus grandis Boheman (Coleoptera: Curculionidae)
US20040096512A1 (en) Phospholipid composition and use of same
EP0666300B1 (en) Method for inhibiting oxiation of oils and fats or fatty acids
US3458637A (en) Compositions stabilized with tocopheramine antioxidants
US2758924A (en) Stabilized vitamin preparations
IE922176A1 (en) Phospholipid composition
US2895878A (en) Compositions containing stabilized vitamin a materials
JPH0439397A (en) Antioxidant for fats and oils
JPS6320383A (en) Antioxidant
US3359167A (en) Vitamin a compositions
US2051257A (en) Stabilized organic compoistion
JP2021106508A (en) Anthocyanin stabilization method
JPH01157369A (en) Tocopherol emulsified composition
SI22341A (en) Antioxidative protection of polyunsaturated oils and products based on polyunsaturated oils

Legal Events

Date Code Title Description
PE20 Patent expired after termination of 20 years

Effective date: 20030317