CA1142434A - Pharmaceutical composition - Google Patents
Pharmaceutical compositionInfo
- Publication number
- CA1142434A CA1142434A CA000344803A CA344803A CA1142434A CA 1142434 A CA1142434 A CA 1142434A CA 000344803 A CA000344803 A CA 000344803A CA 344803 A CA344803 A CA 344803A CA 1142434 A CA1142434 A CA 1142434A
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- hydroxy
- propylthio
- hept
- enoic acid
- 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.)
- Expired
Links
Abstract
ABSTRACT OF THE DISCLOSURE
A novel pharmaceutical composition is provided herein. It con-sists essentially of 7.alpha.-{2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3.alpha.,5.alpha.-dihydroxycyclopent-1-yl}-hept-5-enoic acid and propane-1,2-diol.
Such formulation is stable over long periods of time without special storage conditions having to be maintained.
A novel pharmaceutical composition is provided herein. It con-sists essentially of 7.alpha.-{2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3.alpha.,5.alpha.-dihydroxycyclopent-1-yl}-hept-5-enoic acid and propane-1,2-diol.
Such formulation is stable over long periods of time without special storage conditions having to be maintained.
Description
z~
The invention relates to a novel phar~aceutical composition which contains the pharmaceutically active compound 7~ -~2-[3-(3-chloro-phenoxy)-2-hydroxy-propylthio]-3 ~ ,5 ~ -dihydroxycyclopent-1-yl~-hept-5-enoic acid and a specific excipient or carrier therefor.
7~ -~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5 ~-dihydroxycyclopent-l-yl~-hept-5-enoic acid, which is a compound analogous to prostaglandin, has achieved particular significance in veterinary medicine. It is active in the sexual organs and thus participates in sperm migration, ovulation, fertilization, nidation, luteolysis and uterus contraction. This gives rise to very diverse applications and indications, e.g., estrus induction, cycle synchronization, induction of - labour, termination of undesired pregnancy, persistent corpus luteum, healing of corpus-luteum-cysts and follicule-lutein-cysts, and chronic endometritis, in very diverse species of animals, for example, cattle, horses, pigs and sheep.
Because of its great zootechnical significance, the most impor-tant of these indications is cycle synchronization, for which the targets hitherto have mainly been cattle. In cattle, luteolytic action of 7 ~-~2[3-(3-chlorophenoy)-2-hydroxy-propylthio]-3~C,5 ~ -dihydroxycyclopent-1-yl~-hept-5-enoic acid effects involution of the corpus luteum and the ~ compound i5 therefore active in the perlod of the 5th to the 16th day of ; the cycle. After this luteolysis, a follicle capable of ovulation forms with great reliability and after 2 - 3 days estrus and ow lation take place.
7 ~-{2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3O~,5~ -dihydroxycyclopent-l-yl}-hept-5-enoic acid already has the full desired activity at a dosage which is many times less than that required with the naturally oCcurring prostaglandin F2~. The very good tolerance which exists at the same time is retained, even at considerable overdosages, ~! 30 which can be administered without side effects. Compositions containing -- 1 -- ~
., , 7~-~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5 ~ -dihydroxycyclo-pent-l-yl~-hept~5-enoic acid can be administered intramuscularly, sub-cutaneously, intravenously, intrauterinely, intraperitonously. The intramuscular administration is preferred.
7~-{2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3~ ,5~-dihydroxycyclopent-l-yl~-hept-5-enoic acid is known from German Offen-legungsschrift 2,513,371. 7~-~2-[3-(3-chlorophenoxy)-2-hydroxy-propyl-thio]-3 ~,5e~-dihydroxycyclopent-1-yl~-hept-5-enoic acid is a markedly lipophilic substance which is virtually insoluble in water. It has been found in the past that it is not possible significantly to improve the solubility of 7~ 2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5 ~-dihydroxycyclopent-l-yl~-hept-5-enoic acid in water, even by the addition of very diverse surface-active agents. While an opaque solution of this type can be administered intramuscularly without difficulty, there is a very great danger that the solution then no longer contains the full amount of active ingredient when it is used, since the lipophilic compound 7~-~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3~ 95 ~-dihydroxycyclo-pent-l-y~hept-5-enoic acid can settle in very small droplets on the walls of the vessel.
It is an object, therefore, of a broad aspect of this invention to provide a novel composition containing 7~-~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3~ ,5 ~ -dihydroxycyclopent-l-yl~ hept-5-enoic acid in which 7~-~2-[3(3 chlorophenoxy)-2-hydroxy-propylthio]-3 ~ ,5 ~-dihydroxy-cyclopent-l-yl~hept-5-enoic acid is readily soluble and which enables a composition to be prepared which is stable for a long period without special storage conditions having to be maintained.
By a broad aspect of this invention, a pharmaceutical composition is provided which consists essentially of 7~ -~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5~ -dihydroxycyclopent-1-yl~-hept-5-enoic acid and propane-1,2-diol.
By a variant thereof, the concentration of 7~-~2-[3-~3-chloro-phenoxy)-2-hydroxy-propylthio]-3 ~,5 ~-dihydroxycyclopent-l-yl~hept 5-enoic acid is between 0.0001 and 20 g/l.
Thus, it has ncw surprisingly been found that propane-1,2-diol meets all of the requirements which are made of an excipient for a pharma-ceutical composition, especially an injection solution, of 7~ -~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5:~-dihydroxycyclopent-1-yl3hept-5-enoic acid. It has been found that 7O~-~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5 ~-dihydroxycyclopent-1-yl~hept-5-enoic acid is very readily soluble in propane-1,2-diol, so that the desired completely clear injection solution can be prepared without difficulty.
Moreoverg when propane-1,2-diol is used as the solvent, an injection solution is obtained which,surprisingly, is stable for several years without a special preservative having to be added and without special storage conditions having to be maintained.
This characteristic of the solution of 70~-~2-[3-(3-chloro-pheno~y)-2-hydroxy-propylthio]-3OC,5 ~-dihydroxycyclopent-1-yl~hept-5-enoic acid in propane-1,2-diol is of extremely great importance precisely in the case of its use in veterinary medicine, which in most cases has to be carried out in the open air, since a possibility for storage under special storage condltions does not usually exist.
The pharmaceutical solutions according to aspects of the inven-tion are prepared, for example, by adding propane-1,2-diol to 7O~- 2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5~ -dihydroxycyclopent-l-yl~-- hept-5-enoic acid under aseptic conditions, with protection against light and with the exclusion of traces of water, and if necessary warming to temperatures of up to 80C. and preferably of up to 50C., with stirring, until a clear solution has formed. If necessary, the solution may be cooled and/or may be made up to the desired volume with propane-1,2-diol, with stirring.
4;~34 The concentrations of the pharmaceuti~al solutions of aspects of this invention which can be prepared in this way are appropriately between 0.0001 and 20 g/l, preferably be~ween 0.001 and 10 g/l and in particular 7.5 g/l.
The pharmaceutical solutions of aspects of this invention can be filled into ampoules or vials and each ampoule or vial can contain between 0.1 and 1000 mg oE 7~ -~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3~,5 d-dihydroxycyclopent-1-yl~-hept 5-enoic acid, depending on its size and on the concentration of t'he solution.
Filling of this type is carried out under aseptic conditions, with protection against light and with the substantially complete exclusion of traces of water. For example, a vacuum is applied to the batch vessels and the vessels are filled with an inert gas, appropriately nitrogen.
The clear,'homogeneous solution of 7~ -~2-[3-(3-chlorophenoxy)-
The invention relates to a novel phar~aceutical composition which contains the pharmaceutically active compound 7~ -~2-[3-(3-chloro-phenoxy)-2-hydroxy-propylthio]-3 ~ ,5 ~ -dihydroxycyclopent-1-yl~-hept-5-enoic acid and a specific excipient or carrier therefor.
7~ -~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5 ~-dihydroxycyclopent-l-yl~-hept-5-enoic acid, which is a compound analogous to prostaglandin, has achieved particular significance in veterinary medicine. It is active in the sexual organs and thus participates in sperm migration, ovulation, fertilization, nidation, luteolysis and uterus contraction. This gives rise to very diverse applications and indications, e.g., estrus induction, cycle synchronization, induction of - labour, termination of undesired pregnancy, persistent corpus luteum, healing of corpus-luteum-cysts and follicule-lutein-cysts, and chronic endometritis, in very diverse species of animals, for example, cattle, horses, pigs and sheep.
Because of its great zootechnical significance, the most impor-tant of these indications is cycle synchronization, for which the targets hitherto have mainly been cattle. In cattle, luteolytic action of 7 ~-~2[3-(3-chlorophenoy)-2-hydroxy-propylthio]-3~C,5 ~ -dihydroxycyclopent-1-yl~-hept-5-enoic acid effects involution of the corpus luteum and the ~ compound i5 therefore active in the perlod of the 5th to the 16th day of ; the cycle. After this luteolysis, a follicle capable of ovulation forms with great reliability and after 2 - 3 days estrus and ow lation take place.
7 ~-{2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3O~,5~ -dihydroxycyclopent-l-yl}-hept-5-enoic acid already has the full desired activity at a dosage which is many times less than that required with the naturally oCcurring prostaglandin F2~. The very good tolerance which exists at the same time is retained, even at considerable overdosages, ~! 30 which can be administered without side effects. Compositions containing -- 1 -- ~
., , 7~-~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5 ~ -dihydroxycyclo-pent-l-yl~-hept~5-enoic acid can be administered intramuscularly, sub-cutaneously, intravenously, intrauterinely, intraperitonously. The intramuscular administration is preferred.
7~-{2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3~ ,5~-dihydroxycyclopent-l-yl~-hept-5-enoic acid is known from German Offen-legungsschrift 2,513,371. 7~-~2-[3-(3-chlorophenoxy)-2-hydroxy-propyl-thio]-3 ~,5e~-dihydroxycyclopent-1-yl~-hept-5-enoic acid is a markedly lipophilic substance which is virtually insoluble in water. It has been found in the past that it is not possible significantly to improve the solubility of 7~ 2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5 ~-dihydroxycyclopent-l-yl~-hept-5-enoic acid in water, even by the addition of very diverse surface-active agents. While an opaque solution of this type can be administered intramuscularly without difficulty, there is a very great danger that the solution then no longer contains the full amount of active ingredient when it is used, since the lipophilic compound 7~-~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3~ 95 ~-dihydroxycyclo-pent-l-y~hept-5-enoic acid can settle in very small droplets on the walls of the vessel.
It is an object, therefore, of a broad aspect of this invention to provide a novel composition containing 7~-~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3~ ,5 ~ -dihydroxycyclopent-l-yl~ hept-5-enoic acid in which 7~-~2-[3(3 chlorophenoxy)-2-hydroxy-propylthio]-3 ~ ,5 ~-dihydroxy-cyclopent-l-yl~hept-5-enoic acid is readily soluble and which enables a composition to be prepared which is stable for a long period without special storage conditions having to be maintained.
By a broad aspect of this invention, a pharmaceutical composition is provided which consists essentially of 7~ -~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5~ -dihydroxycyclopent-1-yl~-hept-5-enoic acid and propane-1,2-diol.
By a variant thereof, the concentration of 7~-~2-[3-~3-chloro-phenoxy)-2-hydroxy-propylthio]-3 ~,5 ~-dihydroxycyclopent-l-yl~hept 5-enoic acid is between 0.0001 and 20 g/l.
Thus, it has ncw surprisingly been found that propane-1,2-diol meets all of the requirements which are made of an excipient for a pharma-ceutical composition, especially an injection solution, of 7~ -~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5:~-dihydroxycyclopent-1-yl3hept-5-enoic acid. It has been found that 7O~-~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5 ~-dihydroxycyclopent-1-yl~hept-5-enoic acid is very readily soluble in propane-1,2-diol, so that the desired completely clear injection solution can be prepared without difficulty.
Moreoverg when propane-1,2-diol is used as the solvent, an injection solution is obtained which,surprisingly, is stable for several years without a special preservative having to be added and without special storage conditions having to be maintained.
This characteristic of the solution of 70~-~2-[3-(3-chloro-pheno~y)-2-hydroxy-propylthio]-3OC,5 ~-dihydroxycyclopent-1-yl~hept-5-enoic acid in propane-1,2-diol is of extremely great importance precisely in the case of its use in veterinary medicine, which in most cases has to be carried out in the open air, since a possibility for storage under special storage condltions does not usually exist.
The pharmaceutical solutions according to aspects of the inven-tion are prepared, for example, by adding propane-1,2-diol to 7O~- 2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3 ~,5~ -dihydroxycyclopent-l-yl~-- hept-5-enoic acid under aseptic conditions, with protection against light and with the exclusion of traces of water, and if necessary warming to temperatures of up to 80C. and preferably of up to 50C., with stirring, until a clear solution has formed. If necessary, the solution may be cooled and/or may be made up to the desired volume with propane-1,2-diol, with stirring.
4;~34 The concentrations of the pharmaceuti~al solutions of aspects of this invention which can be prepared in this way are appropriately between 0.0001 and 20 g/l, preferably be~ween 0.001 and 10 g/l and in particular 7.5 g/l.
The pharmaceutical solutions of aspects of this invention can be filled into ampoules or vials and each ampoule or vial can contain between 0.1 and 1000 mg oE 7~ -~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3~,5 d-dihydroxycyclopent-1-yl~-hept 5-enoic acid, depending on its size and on the concentration of t'he solution.
Filling of this type is carried out under aseptic conditions, with protection against light and with the substantially complete exclusion of traces of water. For example, a vacuum is applied to the batch vessels and the vessels are filled with an inert gas, appropriately nitrogen.
The clear,'homogeneous solution of 7~ -~2-[3-(3-chlorophenoxy)-
2-hydroxy-propylthio]-3 ~,5 ~-dihydroxycyclopent-1-yl~-hept-5-enoic acid in propane-1,2-diol is sterile-filtered, likewise under an inert gas atmosphere, preferably through a membrane filter with a pore width of O.2~um. The solution is then filled into sterilized containers, again under an inert gas atmosphere, and the containers are sealed under sterile conditions.
These'novel pharmaceutical compositions of aspects of this inven-tion are preEerably administered in a dosage of 0.001 to 1 mg per kg weight of the species treated and in particular 0.005 to 0.1 mg per kg weight of the species treated. The dosage depends on the species treated, the mode of administration and the purpose of the treatment and can, there-fore, also be above or below the values indicated above.
If, for example, it is deslred to utilize the estrus-synchronizing action of 7~ -~2-[3-~3-chlorophenoxy)-2-hydroxy-propylthio]-3~C,SO~-dihydroxycyclopent-l-yl}hept-5-enoic acid, it is particularly advantageous to inject 0.1 mg to 20 mg, preferably 0.5 mg to 15 mg and in particular ~L~L4Z4~
lo 5 mg to 10 mg of the active ing t intramuscularly into cattle (C~lS
or heifers). In case the phase of the cycle is unknown, the first injec-tion is administered at any time that will suit and the following second injection is administered lO to 12 days later. If the phase of the cycle is known, however, it is advantageous to administer the effective dose by a single injection between the 5th day and the 16th day of the cycle, preferably between the 7th day and the 12th day of tne cycle. It is also possible to inject several partial doses, optionally divided over a period of several days. It is also possible to synchronize the estrus in other useful animals, for example, in sheep, pigs, horses and dogs, by adminis-tration of 7~-~2-[3-(3-chlorophenoxy~-2-hydroxy-propylthio]-3 ~,5~ -dihydroxycyclopent-l-yl~-hept-5-enoic acid. The effective dose varies as a function of the average body weight of the species treated and can be determined without difficulty by those skilled in the art, with the aid of the nominal values indicated above for cattle.
The following Example shows the preparation of a pharmaceutical solution according to one aspect of this invention.
Example 280 g of propane-1,2-diol are added to 2.25 g of 7~ -~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3vC,5 ~ -dihydroxycyclopent-l-yl ~hept-5-enoic acid, the mix~ure is warmed at 40-50C., with stirring, until a solution forms. The solution is cooled to 20C. and made up to 311 g with propane-1,2-diol.
,. I
These'novel pharmaceutical compositions of aspects of this inven-tion are preEerably administered in a dosage of 0.001 to 1 mg per kg weight of the species treated and in particular 0.005 to 0.1 mg per kg weight of the species treated. The dosage depends on the species treated, the mode of administration and the purpose of the treatment and can, there-fore, also be above or below the values indicated above.
If, for example, it is deslred to utilize the estrus-synchronizing action of 7~ -~2-[3-~3-chlorophenoxy)-2-hydroxy-propylthio]-3~C,SO~-dihydroxycyclopent-l-yl}hept-5-enoic acid, it is particularly advantageous to inject 0.1 mg to 20 mg, preferably 0.5 mg to 15 mg and in particular ~L~L4Z4~
lo 5 mg to 10 mg of the active ing t intramuscularly into cattle (C~lS
or heifers). In case the phase of the cycle is unknown, the first injec-tion is administered at any time that will suit and the following second injection is administered lO to 12 days later. If the phase of the cycle is known, however, it is advantageous to administer the effective dose by a single injection between the 5th day and the 16th day of the cycle, preferably between the 7th day and the 12th day of tne cycle. It is also possible to inject several partial doses, optionally divided over a period of several days. It is also possible to synchronize the estrus in other useful animals, for example, in sheep, pigs, horses and dogs, by adminis-tration of 7~-~2-[3-(3-chlorophenoxy~-2-hydroxy-propylthio]-3 ~,5~ -dihydroxycyclopent-l-yl~-hept-5-enoic acid. The effective dose varies as a function of the average body weight of the species treated and can be determined without difficulty by those skilled in the art, with the aid of the nominal values indicated above for cattle.
The following Example shows the preparation of a pharmaceutical solution according to one aspect of this invention.
Example 280 g of propane-1,2-diol are added to 2.25 g of 7~ -~2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3vC,5 ~ -dihydroxycyclopent-l-yl ~hept-5-enoic acid, the mix~ure is warmed at 40-50C., with stirring, until a solution forms. The solution is cooled to 20C. and made up to 311 g with propane-1,2-diol.
,. I
Claims (4)
1. Pharmaceutical composition, consisting essentially of 7.alpha.-{2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3.alpha.,5.alpha.-dihydroxycyclo-pent-l-yl} -hept-5-enoic acid and propane-1,2-diol.
2. Pharmaceutical composition according to claim 1 wherein the concentration of the solution of 7.alpha.-{2-[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3.alpha.,5.alpha. -dihydroxycyclopent-1-yl}-hept-5-enoic acid in propane-1,2-diol is between 0.0001 and 20 g/l.
3. Pharmaceutical composition according to claim 1 wherein the concentration of the solution of 7.alpha.-{2[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3.alpha.,5.alpha. -dihydroxycyclopent-l-yl}-hept-5-enoic acid in propane-1,2-diol is between 0.001 and 10 g/l.
4. Pharmaceutical composition according to claim 1 wherein the concentration of the solution of 7.alpha.-{2[3-(3-chlorophenoxy)-2-hydroxy-propylthio]-3.alpha.,5.alpha. -dihydroxycyclopent-l-yl}-hept-5-enoic acid in propane-1,2-diol is 7.5 g/l.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000344803A CA1142434A (en) | 1980-01-31 | 1980-01-31 | Pharmaceutical composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000344803A CA1142434A (en) | 1980-01-31 | 1980-01-31 | Pharmaceutical composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1142434A true CA1142434A (en) | 1983-03-08 |
Family
ID=4116145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000344803A Expired CA1142434A (en) | 1980-01-31 | 1980-01-31 | Pharmaceutical composition |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1142434A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3530821A1 (en) * | 1985-08-29 | 1987-03-05 | Merck Patent Gmbh | LAPROSTIOLIC SOLUTION |
-
1980
- 1980-01-31 CA CA000344803A patent/CA1142434A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3530821A1 (en) * | 1985-08-29 | 1987-03-05 | Merck Patent Gmbh | LAPROSTIOLIC SOLUTION |
| US4742082A (en) * | 1985-08-29 | 1988-05-03 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Solution of luprostiol and 1,2,-propanediol and methods of preparation and use |
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| MKEX | Expiry |