CA1069051A - Pharmaceutical composition containing 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxypropane - Google Patents
Pharmaceutical composition containing 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxypropaneInfo
- Publication number
- CA1069051A CA1069051A CA239,503A CA239503A CA1069051A CA 1069051 A CA1069051 A CA 1069051A CA 239503 A CA239503 A CA 239503A CA 1069051 A CA1069051 A CA 1069051A
- Authority
- CA
- Canada
- Prior art keywords
- composition according
- bis
- pharmaceutically acceptable
- yloxy
- weight
- 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
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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- 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
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Inorganic Chemistry (AREA)
- Birds (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Zoology (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Medicinal Preparation (AREA)
Abstract
ABSTRACT
There are provided pharmaceutical compositions for the treatment of mouth ulcers in man, the compositions being in the form of a gel, paint or paste and comprising from 0.01 to 20% by weight of 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxypropane or a pharmaceutically acceptable salt thereof in association with a suitable pharmaceutically acceptable adjuvant, diluent or carrier.
There are provided pharmaceutical compositions for the treatment of mouth ulcers in man, the compositions being in the form of a gel, paint or paste and comprising from 0.01 to 20% by weight of 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxypropane or a pharmaceutically acceptable salt thereof in association with a suitable pharmaceutically acceptable adjuvant, diluent or carrier.
Description
01/~/32 5~ 0 5
- 2 This inventi~n concerns pharmaceutical compositions.
1,3-B.is(2-carboxychro~on-5 y].oxy)-2-hydroxypropan~ and the p]~arJ~ceutically acceptable salts thereof are known compounds which are described and cl~imecl in British Patent N~ 1,1447905.
Th~ compounds are kno-nn to be o~ use in the treatment of medical disorders caused or exacerbated by products which arise from the coT~ination of certain types of antibody wi~h specific ~Itlgeil.
In r~n) it has been found that ~he disodium salt of 1,3-bis-(2-car.bo.xychromon~5-yloxy)-2-hydroxypropane is of exccptioTIal merit when a~nistered by i~halation in the treatment of asthn~.
We ha~re now ~ound that 193-bis(2 carboxychromon-5-yloxy~-2-hydrGxrpropane and the pha~maceutically acceptable salts thercof ar~ ~urprisingly of us~ in the treatment in man of aphthous stomatitis (~rLouth ulcers~.
Accordingly~ this in~rention pro~rides a pharmaceutical ¦composition in the forn o a gel, paint or paste cL Illprising fr~Tn 0.01 to 203 by weight of 1,3-bis~2-carbo.~ychromon-5-ylox~-)-2-hydroxypropane or a pharn~cel~Ltically acceptable salt ther~of in association with suitable pharmaceutically acceptable adjuvant, diluent or ~ar~ier.
~Pharmaceutically acce.~table salts of the bis-chrom~ne jinclude the alkali-metal, ~or ~x~T~le sodium or potassiuTn7 salt~
~25 and thc alkaline earth metal, for example calciuml or magnesium, ! - 2 - ~
~16911)5~
-,3 salts. An especially prefelred salt is the disodium salt.
lhc)se compositions, ~hich will naturally l)e applied directly to the afflicted site, prcferably contai~l from 0.5 to 15~o~ more preferahly rom 1 to 5~, for ex~nple from 1.5 to 2.5~9 by weight of the bis-chromone In gencral9 it is believed that a sl~illecl fo~nulation che~lis9: ~oul~ be able to produce a sa~isfactory composition having the desire~l parame~ers~
However, the following dctails are given ~or further guid ~ce as to the prcferred compositions.
The gel cor~ositions o~ the present inv~ntion contain fr~m O.S to 20~, preferably from 0.5 ~o l.O~o~ for example from 1 to 5~ by w~ight o~ a pharrnaceutically acceptable gelling agen~
- The gelling agent crnployed, which r~y be any pharmaeeutically acceptable gelling agent9 is preferably present in the composition in such an ~nount tha~
~le ccnposition is neither so mobile that it runs of~ t3le sitc to whic~l it is applied nor so stiff that it cannot easily be dispensecl or applied. ~lthough the amourlt to be incorporated for best results will vary with the particular gel~ing agent en~loyed, it is believed to be within the compe~Lcnce of any skilled fonnulation chemist to produce a ccmposition havLng the desired aracteris~ics.
~ypical gelling agents which may be employed include hydroxypr~pylmethyl cellulose, sodium carbox~nethyl cellulose, carbox~polymethylene or PV~I/h~ (a copoly~er of methyl vinyl ether and maleic anhydride~.
The carrier employed is prefeTably water, although oth~r carriers may be employed if deslred, ~or exan~le glycerol, propylene glycol or a paraffill base.
.
~~ - 3 -.. . . . . .
- , ~
- . . : : . . ..
07/~37 1LI~Ç;9 The gels of the present invention prefcrably contain a complexing agent, for example the disodium salt o et]~ylenediamine tetraacetic acid (~DIA), since this preven~s the forrnation of msoluble hea~y metal salts o~ ~he bis-chromone1 Ihe co]nplexing S agent is preferably present in an amount of from 0.01 to 0.1 by weight of the gel.
The gels rnay be prepared by conventional gel-forming procedures, for example by dissolving the 1,3-bis(2-carbo~ychron~n -5-ylo~ 2 hydroxypropane or salt th~reof at an elevated temperature in the carrier, and coolin~ t],e solution to form the desired gel.
The paints of the present invention conta-in a liquid carrier, for exan~le water, and a thicXening agent, ~or ex~nple glycerol, soldi~n carboxymethylcellulose or pothyethylene glycol in an amount of from 0.5 to 2.0~ by weight of the paint.
The paints may be prepared by conventional paint-for mng procedures. For example, the ingredients may be rnixed ~nd blended to the desired consistency.
The past~ compositions of the present inven~ion contain one or more thickening agent, for example gelatin, pectin, zinc oxide, polyethylene glycol, starch, bentonite or a cellulose derivatiYe such as carboxymethyl cellulose, in an amou~t in total of from 2 to 30~ by weight of the paste, and an aqueo~s or li~uid paraffin base.
lhe paste composition rnay be prepared by conventional paste-forrning procedures. Thus, for exa~n)le, the ingredients rnay .
$3~g ~59L
simply be admixed, ~th heating if necessary to gi~e a homogeneous product followed by cooling, to give the desired paste. Any insoluble mat~ri~ls in the paste should desirably have a mass median diameter of less thanl50 microns.
1 5 me dosage to be administered ~ill depend to some extent on ¦ thê severity o ~he af~liction to be treated. However, a dosage of from 0.5 mg to 30.0 mg, preferably 1.5 mg to 20.Q mg of the bis-chro nc, administered in a gel, paint or pas~e directly on the afflicted site 1 to 4 ~mes a day ti.e. a preferred daily dosag~ of from 1.5 mg to 80.0 mg) is cvenerally found to be sa~isfactory.
~aturally, the compositions of the present invention may also contain flavouring or c~louring agents; preservatives, or other ¦ n~dic~nents as desired.
All the components of the compositions of the present inYentio.l are d^sirably sterile.
~his invention is further described, ~hough only by way of illustration, in the follo~ing Examples.
.. .. .. .. . , .. .. ~ . ~
: ~
~le following ingredie]lts ~ere foImulated into a gel as described below:
w!W
1~3-bist2--c~rbGxychromon-5-lyoxy) 2-hydroxypropane, disodi.ml salt 2.00 ¦ Disodiwn salt of ethy]enediamine 1 25 teiraacetic acid 0.01 J l-~droxypropylrnetllyl ce~lulose (5000 cp) 2.00 I ~Yater 95~99 1 . loo.oo .
.:
.
. ~
~ /32 '` lO~ S~
The bis-chromone and the disodium salt of ethylenedian~ne tetraacetic acid were dissolved in part of the water, and the solution was heated to 95~C. l~e hydroxypropyl methyl ccllulose was then disp~rsed into this solution, and the mixture was cool~d 5 with stirring in such a way as to avoid the incorporation of air.
- ~he remainder of the water was then added, and the mixture cooled to 4C overnight, with stirring to avoid the incorporation of air, to allow the hydroxypropyl methyl cellulose to dissolve. A
gel resulted of appropriate physical characteristics to render it suitable for application in ~he mou~h.
_ample i The following ingredients were formulated into a pam~. as described below:
1,3-bis(2-carboxychromon-5-yloxy)-2 hydroxypropane~
disodium salt 2.0 Ethyl alcohol ~90-0) 20.
Glycerol 20 0 Purified water 58.0 1~0.0 The disodium salt was dissolw d in part of the water, and the ethyl alcohol and glycerol were then added to the solution.
Finally, the remainder of the water was added to give a paint of acceptable characteristics~
2~ ~ 6 ~
, ' . .'. : ~
6911~5~
- 7; -Example 3 The following ingredients were forn~lated into a paste asdescribed below:
- ~ wJw 1,3 bis(2-carboxychromon^5-yloxy)-2-hydroxypropane, disodi~n salt (mass median diameter < 10 microns) 5.0 Bentoni~e 10.0 Glycerol 10.0 Distilled water 75.0 100~0 . . ...
The bentonite was heated a~ lSO~C for 1 hc.ur to st.erilise it, , and was then mixed Wi~l the disodi~ salt., The glycerol was then added with trituration, followed by the water. A paste resulted o~ acceptable quality.
.' ' ,.
, 20 . ' .
~5 . , "
. ~' -- ' ' : ':, -. . .
1,3-B.is(2-carboxychro~on-5 y].oxy)-2-hydroxypropan~ and the p]~arJ~ceutically acceptable salts thereof are known compounds which are described and cl~imecl in British Patent N~ 1,1447905.
Th~ compounds are kno-nn to be o~ use in the treatment of medical disorders caused or exacerbated by products which arise from the coT~ination of certain types of antibody wi~h specific ~Itlgeil.
In r~n) it has been found that ~he disodium salt of 1,3-bis-(2-car.bo.xychromon~5-yloxy)-2-hydroxypropane is of exccptioTIal merit when a~nistered by i~halation in the treatment of asthn~.
We ha~re now ~ound that 193-bis(2 carboxychromon-5-yloxy~-2-hydrGxrpropane and the pha~maceutically acceptable salts thercof ar~ ~urprisingly of us~ in the treatment in man of aphthous stomatitis (~rLouth ulcers~.
Accordingly~ this in~rention pro~rides a pharmaceutical ¦composition in the forn o a gel, paint or paste cL Illprising fr~Tn 0.01 to 203 by weight of 1,3-bis~2-carbo.~ychromon-5-ylox~-)-2-hydroxypropane or a pharn~cel~Ltically acceptable salt ther~of in association with suitable pharmaceutically acceptable adjuvant, diluent or ~ar~ier.
~Pharmaceutically acce.~table salts of the bis-chrom~ne jinclude the alkali-metal, ~or ~x~T~le sodium or potassiuTn7 salt~
~25 and thc alkaline earth metal, for example calciuml or magnesium, ! - 2 - ~
~16911)5~
-,3 salts. An especially prefelred salt is the disodium salt.
lhc)se compositions, ~hich will naturally l)e applied directly to the afflicted site, prcferably contai~l from 0.5 to 15~o~ more preferahly rom 1 to 5~, for ex~nple from 1.5 to 2.5~9 by weight of the bis-chromone In gencral9 it is believed that a sl~illecl fo~nulation che~lis9: ~oul~ be able to produce a sa~isfactory composition having the desire~l parame~ers~
However, the following dctails are given ~or further guid ~ce as to the prcferred compositions.
The gel cor~ositions o~ the present inv~ntion contain fr~m O.S to 20~, preferably from 0.5 ~o l.O~o~ for example from 1 to 5~ by w~ight o~ a pharrnaceutically acceptable gelling agen~
- The gelling agent crnployed, which r~y be any pharmaeeutically acceptable gelling agent9 is preferably present in the composition in such an ~nount tha~
~le ccnposition is neither so mobile that it runs of~ t3le sitc to whic~l it is applied nor so stiff that it cannot easily be dispensecl or applied. ~lthough the amourlt to be incorporated for best results will vary with the particular gel~ing agent en~loyed, it is believed to be within the compe~Lcnce of any skilled fonnulation chemist to produce a ccmposition havLng the desired aracteris~ics.
~ypical gelling agents which may be employed include hydroxypr~pylmethyl cellulose, sodium carbox~nethyl cellulose, carbox~polymethylene or PV~I/h~ (a copoly~er of methyl vinyl ether and maleic anhydride~.
The carrier employed is prefeTably water, although oth~r carriers may be employed if deslred, ~or exan~le glycerol, propylene glycol or a paraffill base.
.
~~ - 3 -.. . . . . .
- , ~
- . . : : . . ..
07/~37 1LI~Ç;9 The gels of the present invention prefcrably contain a complexing agent, for example the disodium salt o et]~ylenediamine tetraacetic acid (~DIA), since this preven~s the forrnation of msoluble hea~y metal salts o~ ~he bis-chromone1 Ihe co]nplexing S agent is preferably present in an amount of from 0.01 to 0.1 by weight of the gel.
The gels rnay be prepared by conventional gel-forming procedures, for example by dissolving the 1,3-bis(2-carbo~ychron~n -5-ylo~ 2 hydroxypropane or salt th~reof at an elevated temperature in the carrier, and coolin~ t],e solution to form the desired gel.
The paints of the present invention conta-in a liquid carrier, for exan~le water, and a thicXening agent, ~or ex~nple glycerol, soldi~n carboxymethylcellulose or pothyethylene glycol in an amount of from 0.5 to 2.0~ by weight of the paint.
The paints may be prepared by conventional paint-for mng procedures. For example, the ingredients may be rnixed ~nd blended to the desired consistency.
The past~ compositions of the present inven~ion contain one or more thickening agent, for example gelatin, pectin, zinc oxide, polyethylene glycol, starch, bentonite or a cellulose derivatiYe such as carboxymethyl cellulose, in an amou~t in total of from 2 to 30~ by weight of the paste, and an aqueo~s or li~uid paraffin base.
lhe paste composition rnay be prepared by conventional paste-forrning procedures. Thus, for exa~n)le, the ingredients rnay .
$3~g ~59L
simply be admixed, ~th heating if necessary to gi~e a homogeneous product followed by cooling, to give the desired paste. Any insoluble mat~ri~ls in the paste should desirably have a mass median diameter of less thanl50 microns.
1 5 me dosage to be administered ~ill depend to some extent on ¦ thê severity o ~he af~liction to be treated. However, a dosage of from 0.5 mg to 30.0 mg, preferably 1.5 mg to 20.Q mg of the bis-chro nc, administered in a gel, paint or pas~e directly on the afflicted site 1 to 4 ~mes a day ti.e. a preferred daily dosag~ of from 1.5 mg to 80.0 mg) is cvenerally found to be sa~isfactory.
~aturally, the compositions of the present invention may also contain flavouring or c~louring agents; preservatives, or other ¦ n~dic~nents as desired.
All the components of the compositions of the present inYentio.l are d^sirably sterile.
~his invention is further described, ~hough only by way of illustration, in the follo~ing Examples.
.. .. .. .. . , .. .. ~ . ~
: ~
~le following ingredie]lts ~ere foImulated into a gel as described below:
w!W
1~3-bist2--c~rbGxychromon-5-lyoxy) 2-hydroxypropane, disodi.ml salt 2.00 ¦ Disodiwn salt of ethy]enediamine 1 25 teiraacetic acid 0.01 J l-~droxypropylrnetllyl ce~lulose (5000 cp) 2.00 I ~Yater 95~99 1 . loo.oo .
.:
.
. ~
~ /32 '` lO~ S~
The bis-chromone and the disodium salt of ethylenedian~ne tetraacetic acid were dissolved in part of the water, and the solution was heated to 95~C. l~e hydroxypropyl methyl ccllulose was then disp~rsed into this solution, and the mixture was cool~d 5 with stirring in such a way as to avoid the incorporation of air.
- ~he remainder of the water was then added, and the mixture cooled to 4C overnight, with stirring to avoid the incorporation of air, to allow the hydroxypropyl methyl cellulose to dissolve. A
gel resulted of appropriate physical characteristics to render it suitable for application in ~he mou~h.
_ample i The following ingredients were formulated into a pam~. as described below:
1,3-bis(2-carboxychromon-5-yloxy)-2 hydroxypropane~
disodium salt 2.0 Ethyl alcohol ~90-0) 20.
Glycerol 20 0 Purified water 58.0 1~0.0 The disodium salt was dissolw d in part of the water, and the ethyl alcohol and glycerol were then added to the solution.
Finally, the remainder of the water was added to give a paint of acceptable characteristics~
2~ ~ 6 ~
, ' . .'. : ~
6911~5~
- 7; -Example 3 The following ingredients were forn~lated into a paste asdescribed below:
- ~ wJw 1,3 bis(2-carboxychromon^5-yloxy)-2-hydroxypropane, disodi~n salt (mass median diameter < 10 microns) 5.0 Bentoni~e 10.0 Glycerol 10.0 Distilled water 75.0 100~0 . . ...
The bentonite was heated a~ lSO~C for 1 hc.ur to st.erilise it, , and was then mixed Wi~l the disodi~ salt., The glycerol was then added with trituration, followed by the water. A paste resulted o~ acceptable quality.
.' ' ,.
, 20 . ' .
~5 . , "
. ~' -- ' ' : ':, -. . .
Claims (9)
1. A pharmaceutical composition in the form of a gel, paint or paste comprising from 0.01 to 20% by weight of 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxypropane or a pharmaceutically acceptable salt thereof in association with a suitable pharmaceutically acceptable adjuvant, diluent or carrier.
2. A composition according to claim 1 which contains a pharmaceutically acceptable alkali-metal or alkaline earth metal salt of 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxypropane.
3. A composition according to claim 2 wherein the alkali-metal salt is the disodiun salt.
4. A composition according to claim 1 which contains from 0.5 to 15% by weight of the 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxy-propane or pharmaceutically acceptable salt thereof.
5. A composition according to claim 1 in the form of a gel containing from 0.5 to 20% by weight of a pharmaceutically acceptable gelling agent.
6. A composition according to claim 5 wherein the gelling agent is selected from the group consisting of hydroxypropylmethyl cellulose, sodium carboxymethyl cellulose, carboxypolymethylene or a copolymer of methyl vinyl ether and maleic anhydride.
7. A composition according to claim 1 in the form of a paint comprising the active ingredient, a liquid carrier and from 0.5 to 2.0% by weight of a thickening agent.
8. A composition according to claim 7 wherein the thickening agent is selected from the group consisting of glycerol and polyethylene glycol.
9. A composition according to claim 1 in the form of a paste containing from 2 to 30% by weight of a thickening agent and an aqueous or liquid paraffin base.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB48591/74A GB1486841A (en) | 1974-11-09 | 1974-11-09 | Pharmaceutical compositions containing bis-chromones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1069051A true CA1069051A (en) | 1980-01-01 |
Family
ID=10449167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA239,503A Expired CA1069051A (en) | 1974-11-09 | 1975-11-10 | Pharmaceutical composition containing 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxypropane |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE835236A (en) |
| CA (1) | CA1069051A (en) |
| GB (1) | GB1486841A (en) |
| ZA (1) | ZA756989B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE891013A (en) * | 1980-11-05 | 1982-05-05 | Fisons Ltd | PHARMACEUTICAL COMPOSITIONS |
-
1974
- 1974-11-09 GB GB48591/74A patent/GB1486841A/en not_active Expired
-
1975
- 1975-11-04 BE BE161572A patent/BE835236A/en not_active IP Right Cessation
- 1975-11-07 ZA ZA756989A patent/ZA756989B/en unknown
- 1975-11-10 CA CA239,503A patent/CA1069051A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE835236A (en) | 1976-05-04 |
| ZA756989B (en) | 1976-11-24 |
| GB1486841A (en) | 1977-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |