IE45282B1 - Pharmaceutical tablet formulation - Google Patents
Pharmaceutical tablet formulationInfo
- Publication number
- IE45282B1 IE45282B1 IE1038/77A IE103877A IE45282B1 IE 45282 B1 IE45282 B1 IE 45282B1 IE 1038/77 A IE1038/77 A IE 1038/77A IE 103877 A IE103877 A IE 103877A IE 45282 B1 IE45282 B1 IE 45282B1
- Authority
- IE
- Ireland
- Prior art keywords
- formulation according
- active ingredient
- weight
- diluent
- formulation
- Prior art date
Links
Classifications
-
- 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
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2009—Inorganic compounds
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
Abstract
There is described a pharmaceutical tablet formulation comprising an anti-allergic drug having sodium cromoglycate like activity, as active ingredient, in combination with a lubricant and a diluent (and preferably also a flow aid and a binder) the low aid, binder, lubricant and diluent containing no material capable of causing an adverse reaction in an allergic patient. Unit dosage forms of 6,7,8,9-tetrahydro-4-oxo-10-propyl-4H-naphtho¢2,3-b!pyran-2-carboxylic acid and 6,7,8,9-tetrahydro-S-hydroxy-4-oxo-10-propyl-4H-naphtho¢2,3-b!pyran-2-ccarboxylic acid are also described. The formulations and unit dosage forms are indicated for use in the treatment of allergies.
Description
This invention relates to a novel formulation.
It has for a number of years been Inown to formulate a variety of anti-allergic drugs with various excipients in order to present the drugs in a convenient pharmaceutically acceptable form. However 5 a number of the excipients have been found to be, or contain, materials to which some patients are allergic. Thus the anomolous situation has arisen in which it has been proposed that a group of patients who’ may be particularly prone to allergies should be treated with an anti-allergic drug which has been formulated with
1° a material capable of causing an adverse, e.g allergic, reaction.
According to the invention we provide a pharmaceutical tablet formulation comprising an anti-allergic pyran-4-one compound having sodium cromoglycate like'activity, as active ingredient, in combination with a lubricant and a diluent, the lubricant and diluent containing no material capable of causing an allergic reaction in an allergic patient.
The formulation preferably also contains a flow aid and/or a binder, the flow aid and/or the binder containing no material • capable of causing an allergicreaction in an allergic patient.
2° The material capable of causing an alergic reaction in the patient may be a material, which contains residual traces of an anti-biotic such as penicillin or may be a material containing an actually or
- 2 - 3 potentially allergenic material.
Material wdiich is not actually or potentially allergenic is material which will not result in increased hypersensitivity of the individual treated to the material. The material should not be capable of eliciting an immune response, either anti-body or cell mediated. The material should also not combine with protein to for;.! a hapten carrier system and should not activate tha complement pathways in formation of CSa or C3a.
We particularly prefer there to be no proteinaceous material 10 in the formulation. Examples of materials which should be excluded from the formulation are gelatin, starch, starch derivatives (e.g sodium starch glycollate) and acacia. Materials which contain traces of protein because of their origin, e.g lactose; or method of manufacture, e.g maltose-dextrose combinations produced by enzyme treatment (and sold under the Trade Mark Emdcx) should also be excluded from the formulation.
The formation of the cablet may comprise the steps of wet granulation, dry granulation, melting, moulding, enteric coating, film coating or formation into controlled release form. However we prefer to use a composition which can be compressed into a tablet directly without an intermediate, e.g. a wet. or dry granulation, stage.
The flow aid may be, for example, purified talc or silicon dioxide and especially colloidal silicon dioxide having a mean particle size of about 12 mM.
- 3 48282
- 4 Tiie binder may be, for example, polyvinylpyrrolidone or methyl cellulose.
The lubricant may be, for example, stearic acid, a metallic stearate, a polyethylene glycol of molecular weight of 4,000 or more, or purified talc.
The diluent, which may also serve as disintegrant, may be microcrystalline cellulose, or a cellulose derivative, e.g a cellulose ether such as methyl cellulose; or sodium bicarbonate or dibasic calcium phosphate. The formulation may also comprise a disintegrant eb a entity separate from the diluent. Vihen the disintegrant is a separate entity it should contain no material capable of causing an allergic reaction in an allergic patient.
The formulation may be made by dry mixing the active ingredient with the other ingredients,’ e.g the flow aid, binder, lubricant and diluent/disintegrant, for example in a powder blending machine. The mixing may be carried out in Wo stages, the blend., or parts thereof, being sieved through an appropriate screen (e.g 60 mesh, 250 micron) at the «2nd of a first stage in order to disperse any persistant aggregates. The sieved powder may then be mixed further. The resulting mixture may then be compressed in a tablet forming machine.
The active ingredient may ba any suitable anti-allergic gyran-4-one, having sodium cromoglycate like activity. A drug having sodium cromoglycate like activity is able to inhibit the release of
- 4 :3282 pharmacological mediators which result from the in vivo combination of certain types of anti-body and specific antigen, for example the combination of reaginic antibody .and specific antigen (see Example 27 of British Patent Specification No 1,292,601 - the rat passive cutaneous anaphylaxis test).
The active ingredients may be characterised by the following biological tests and results thereof.
The compound is first tested in the rat passive cutaneous anaphylaxis test. If the compound does not show significant inhibition of allergic manifestations at 20 mg/kg intrancritoneally (i.p) or intravenously (i.v) in this test, its activity is generally too low. Various other biological tests may bo used to show that the compound exhibits its anti-allergy activity as an inhibitor of mediators of anaphylaxis rather than as, for example an end organ antagonist, cholinergic or anti-cholinergic, and adenyl cyclase stimulator. Therefore, tests to see if the compound inhibits the effect of histamine, serotonin, and slow reacting substance of anaphylaxis (SRSA), that is, that the compound is an end organ antagonist of the mediators, may be enoloyed. Such tests are well known and include contraction of guinea pig ileum in the presence- of mcthylsergide for serotonin activity. If activity is stili observed in these systems, it is due to histamine action. A further check on histamine is through the spectrafluorimetric assay described by Shore, Burkhalter and Cohn, Journal of Pharmacology and Experimental Therapeutics, Vol 127 page 132. Active ingredients according to the invention are not end organ antagonists.
If the results from these tests show that the active ingredient is not an end organ antagonist further tests may be run to show that the compound is not exhibiting its activity through cholinergicity or anti-cholinergicity, e.g.
by the reversal of acetylcholine induced guinea pig tracheal t
chain contraction. An active ingredient will not be a cholinergic or anti-cholinergic.
Specific groups of active ingredients are to be found 10 among the pyran-4-one-2-oarboxylic acids, and suitable derivatives thereof, e.g. those described in Patent Specification Nos. 35506, 29563 and Patent Specification No.
32345 and West German Patent Specification No. 2,553,688.
Particularly preferred are the pyran-4-one compounds 15 of Patent Specification No. 29563 and British Patent Specificat ion No. 1,230,087 and West German Patent Specification No. 2,553,688. More specifically we prefer 1,3-bis(2-carboxychromon-5-yloxy)propan-2-ol or a pharmaceutically acceptable derivative, e.g. salt such as the disodium salt, thereof;
this latter is commonly known as sodium '3 ΰ 2 8 2
- 7 cromoglycate or cromolyn sodium. As further preferred compounds there may be mentioned 6,7,S,3-tctrahydro-4-oxo-10~propyl-4!lnapntho/72,3-b27pZra!1--2-carbo?;ylic acid and pharmaceutically acceptable derivatives thereof (collectively referred to herein
S as 'active ingredient B') and 6,7,8,9-tetrahydro-5-hydroxy-4-oxo10-propyl-4II-naphtho£2,3-b27pyran-2-carboxylic acid and pharmaceutically acceptable derivatives thereof (collectively referred to herein as 'active ingredient A'). When using the pyran 4 - one compounds described in this paragraph we prefer the composition not to contain di- or tri- basic cations. Pharmaceutically acceptable derivatives within the meaning of active ingredient A or B include pharmaceutically acceptable salts, esters and amides of the 2-carboxylic acid group. Suitable salts include ammonium, alkali metal (e.g sodium, potassium and lithium) salts and salts with suitable organic bases, e.g salts with hydroxylamine, lower alkylamines such as niethylamine or ethylamine, with substituted lower alkylamines, e.g hydroxy substituted alkylamines such as tris(hydroxymethyl)mcthylaminc, or with simple monocyclic nitrogen heterocyclic compounds, e.g piperidine or morpholine. Suitable esters include simple lower alkyl esters, e.g the ethyl, ester, esters derived from alcohols containing basic groups, e.g di-lower alkyl amino substituted slkanols such as the β -(diethoxyaraino)-ethyl ester, and acyloxy alkyl asters, e.g a lower acyl-lcwer alkyl ester such as the pivaloyloxymethyl ester, or a bis-ester derived from a dihydroxy
- 7 ¢3383
- 8 coinpound, e.g a di(hydroxy-lower allyl) ether, e.g the bis-2oxapropan-l,3-diyl ester. The pharmaceutically acceptable salts of the basic esters, e.g the hydrochloride, may also be used.
We prefer to use as active ingredient A or B the free 5 carboxylic acid or the sodium salt thereof. In particular we prefer to use the free carboxylic acid as it is more orally acceptable tlian the derivatives thereof.
We prefer the formulation to contain less than 505, and preferably between about 0.5 and 185 by weight of active ingredient A or B. Unexpectedly even with very small proportions of active ingredient A or B we have found that a lubricant is highly desirable. We prefer the lubricant to comprise up to 4.05, and preferably 0.2 to 4.05, by weight of the composition. We also prefer the composition to contain between about 0.1 and 5.05, e.g.
about 0.55, by weight of the flow aid. We prefer the binder to comprise from about 0.5 to 55 by weight of the composition, and the diluent/disintegrant to comprise from about 80 to 995 by weight of the composition.
We prefer tablet formulations containing an active ingredient
A to contain from 3 to 155, and more preferably from 4 to 3.05 by weight of water as such formulations.have advantageous flow and compression characteristics.
’282
Tablets according to the invention preferably Lave.· a diametral crushing strength of at least 1.5, and preferably from 3 to 7, 1φ Schleuniger (Dr K Schleuniger and Co, Zurich, Switzerland). We also prefer tliat the tablets arc such tint when tested using the disintegration test annaratus of the United States Pharmacopoeia XIX, using water as the medium, they disintegrate in less than 3C minutes. We also prefer that the tablets have a low friability.
In particular we prefer that, when 20 pre-dusted and weighed tablets are rotated in a Koche Friabilator drum (Shafer EGE, Wollish EG and Engel CE Journal of the American Pharmaceutical Association (1956) Vol 45 pages 114-116) at 25 ran for 8 minutes, and are then re-dusted, the tablet weight loss shall be less than 32., and more preferably less than 1’.
The unit dosages and other compositions of this invention, and ir. particular compositions containing sodium cromoglycate or an active ingredient A or B, are indicated for use in the treatment of allergic conditions, e.g asthma, (notably allergic asthma) and conditions of the gastrointestinal tract such as Crohn's disease, ulcerative colitis and proctitis. The unit dosages and other compositions are also indicated for use in the treatment of so-called 'intrinsic' asthma (in which no sensitivity to extrinsic antigen can be demonstrated). The unit dosages and other compositions are also indicated for use in the treatment of hay fever, urticaria and eczema.
We particularly prefer formulations containing l,3-bis(2- 9 ¢5282
- 10 carboxy-chromon-5-yloxy)prpp:in-2-ol or 6,7,8,9-toi.rahydro-5hydroxy-4-oxo-10-propyl-4H-naphthoZ72,3-bZ7pyran-2-carboxylic acid, or a pharinacsutically acceptable derivative of either thereof.
Ehasanaceutical formulations comprising fean 2 to 5Qmg of active ingredient AarB in unit dosage form are described and claimed in Patent Specification No.
The invention is illustrated, but in no way limited by the following Examples.
Example 1
Tablet mg/tablct
Micronised or milled 6,7,8,9-tetrahydro-Shydroxy-4-oxo-10-propyl-4I I-naphtho/2,3-b/ pyran-2-carboxylic acid 3.0 Colloidal silicon dioxide ’Aerosil 200’ (Aerosil is a Trade Mark) 0.5 Polyvinylpyrrolidone ’Plasdone’ K29-32 · (Plasdone is a Trade Marie) 2.0 Stearic acid 60 mesh 0.5 Macrocrystalline cellulose ’Avicel PH 101* (Avicel is a Trade Mark) 94.0
Approximately 100.0
Hie micronised or milled 6,7,8,9-tetrahydro-5-hydroxy-4-oxo10-pronyl-4n-naphthoZ2,3-b7pyran-2-cnrboxyIic acid was mixed with the colloidal silicon dioxide, polyvinylpyrrolidone, stearic acid and the microcrystalline cellulose in a high speed powder blender. The walls of the blender and its impeller blade were scraped down with a spatula after about 5 minutes mixing and the mixing was then continued until a suitable degree of mixing had been achieved.
To improve the flow and compression properties and to improve tablet stability on storage (with respect to crushing strength and
4-5 2.8 2 disintegration time) the moisture content of the blend was controlled within the range 3-155 w/w, and preferably within the range 4-105 w/w.
The final mixture was then compressed in a tablet forming machine to a diametral crushing strength of 5 kp Schlcuniger. Example 2 mg/tablet
Tablet
Sodium Cromoglycate B.P Sodium Bicarbonate , B.P Purified Talc
Total weight dry
200
150
366
The sodium cromoglycate and sodium bicarbonate were dry mixed together in a planetary mixer, then moistened with purified water,
IS approximately 20 parts of water being added to 100 parts by weight solids. The moistened material was passed through a 16 mesh screen then dried in a fluid bed drier, The purified talc was blended into the dry granules and the tablets compressed on 10 mm punches on a rotary tablet machine to a diametral crushing strength of
6-8 kp Schleunigcr.
4»
Example 3
Tablet mg/tablet
G, 7,8,9-Tetrahydro-4-oxo-10-pronyl-4nnaphtho£2,3-bJ7pyran-2-carboxylic acid micronised or milled 2S.0
Sodium bicarbonate B.P 75.0
Microcrystalline cel1ulose 'Avicel PH 101' 50.0
Methyl cellulose 20 B.P.C (added as 5¾ aqueous solution) 1.5
Stearic acid 60 mesh 3.0
154.5
The 6,7,8,9-tetraliydro-4-oxo-10-propyl-4H-naphthoZ72,3-1/7pyran-2-carboxylic acid, half the microcrystalline cellulose and the sodium bicarbonate were dry mixed together and moistened with a 5¾ aqueous solution of the methyl cellulose, adding appropriately
parts of solution to 100 parts by weight of powder. The t
moistened powder was granulated through a 16 mesh (1,000 micron) I screen, and fluid bed dried using an inlet air temperature of 60°C. ·
The dried granules were passed through a 16 mesh (1,000 micron) ;
i screen and mixed with the remaining microcrystalline cellulose and ί the stearic acid. The blend was compressed on a tablet forming j t
machine to a diametral crushing strenth of 4-7 kp Schleuniger. ;
Claims (11)
1. A pharmaceutical tablet formulation comprising an anti- allergic pyran-4-one having sodium cromoglycate life activity, as active ingredient, in combination with a lubricant and a diluent, the 5. lubricant and diluent containing no material capable of causing an allergic reaction in an allergic patient.
2. A formulation according to Claim 1 comprising 8 a ^'s, the tlow aid containing no material capable of causing an allergic reaction in an allergic patient. 10
3. A formulation according to Claim 1 or Claim 2 comprising a binder, the binder containing no material capable of causing an allergic reaction in an allergic patient.
4. A formulation according to any one of the preceding claims, wherein the diluent also serves as a disintegrant. 15 5. A formulation according to any one of the preceding claims comprising a disintegrant as an entity separate from the diluent. 6. A formulation according to any one of the preceding claims and comprising a flow aid, binder, lubricant and diluent containing no actually or potentially allergenic material. 20 7. A formulation according to any one of the preceding claims, which can be compressed into a tablet directly. 8. A formulation according to any one of the preceding claims, comprising purified talc or silicon dioxide as flow aid. . . - 13 - 14 9. A formulation according· to Claim 8, wherein tho flow aid is colloidal silicon dioxide. 2°· A formulation according to any one of the preceding claims, comprising polyvinylpyrrolidone or methyl cellulose as binder.
5. 11. A formulation according to any one of the preceding claims, wherein the diluent is microcrystalline cellulose, a cellulose ether, sodium bicarbonate or dibasic calcium phosphate. 12. A formulation according to any one of the preceding claims, wherein the active ingredient is l,3-bis(2-carboxychromon-510 yloxy)propan-2-ol or a pharmaceutically acceptable derivative thereof. 13. A formulation according to Claim 12, wherein the active ingredient is sodium cromoglycate. 14. A formulation according to any one of Claims 1 to 11, wherein 15 the active ingredient is
6. ,
7. ,
8. ,
9. -tetrahydro-4-oxo-10-propyl-4HnaphthoZ72,3-b27pyvan-2-carboxylic acid, or a pharmaceutically acceptable derivative thereof. 15. A formulation according to any one of Claims 1 to n, wherein the active ingredient is 6,7,8,9-tetrahydro-5-hydrcxy-4-oxo-1020 propyl-4H-naphtho/72,3~fcC7pyraft-2-carboxylic acid, or a pharmaceutically acceptable derivative thereof. 16. A formulation according to Claim 14, wherein the active ingredient is 6,7, S,9“tetrahydro-5-hydroxy-4-oxo-10-propyl-4H-naph.br o /2,3-b J pyran-Z-carboxylic acid. 25 17. A formulation according to Claim 15, wherein the active - 14 l s 3 s a - 15 ingredlent is 6,7,3, 9-tetrahydro·- S-hydroxy-4-oxo·· 10-propyl-411naphtho£”2,3--b27pyren~ 2-carboxylic acid. 15. A formulation according to 3ny one of Claims 14 to 17 containing less than 501 by weight of active ingredient. S. IS- A formulation according to Claim 18 containing from 0.5 to 181 by weight of active ingredient. 20. A fci-siula;.lor according to any one of Claims 14 to 19 containing from 0.1 to 5.05 by weight of flow aid. 21, A fcimulation according to any one cf Claims I4to 20
10. Wherein the binder comprises from 0.5 to 55 by weight of the composition. <2. A formulation according to anv one of Claims 14 to 21 wherein the diluent comprises from SO to 995 by weight of the composition. IS 23. Λ formulation according to any one of Claims 14 to 22 wherein the lubricant comprises from 0.2 to 4.05 by weight of the composition. 24. A formulation according to any one of Claims 1 to 11,15 or 17 tc 23 containing 6,7,3,9-tetrah.ydro-5-hydroxy-4-oxo-10-propyl“ 20 4H-na0itho£’2,3-bJ7pyran-2“carbQxylic acid, or a pharmaceutically acceptable derivative thereof, and from 3 to 155 by weight of water. 25. A formulation according to Claim 24 containing from 4 to 105 by weight of water- 15 . 4 b ¢5 θ 2 _ 2 _ 26. A formulation according to any one of the preceding claims in the form of a tablet having a diametral crushing strength of at least 1.5 kp Schleuniger. 27. A formulation according to Claim 26, wherein the tablet lias 5 a diametral crushing strength of from 3 to 7 kp Schleuniger. 28. A formulation according to any one of the preceding claims in the form of a tablet which, when tested using the disintegration test apparatus of the United States Pharmacopoeia XIX, using water as the medium, disintegrates in less than 30 minutes. 10 29. A pharmaceutical formulation substantially as hereinbefore described ih any ope of the Examples. 30. A method of making a formulation according to Claim 1, which comprises mixing the ingredients. 31. A method according to Claim 3Q wherein the mixing is
11. 15 carried out in two stages, the blend being sieved through a fine screen at the end of the first stage.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE2005/80A IE45283B1 (en) | 1976-05-21 | 1977-05-20 | Pharmaceutical formulation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB20984/76A GB1570993A (en) | 1976-05-21 | 1976-05-21 | Pharmaceutical tablet formulation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE45282L IE45282L (en) | 1977-11-21 |
| IE45282B1 true IE45282B1 (en) | 1982-07-28 |
Family
ID=10155196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1038/77A IE45282B1 (en) | 1976-05-21 | 1977-05-20 | Pharmaceutical tablet formulation |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS52143220A (en) |
| AU (1) | AU511269B2 (en) |
| BE (1) | BE854690A (en) |
| CA (1) | CA1105835A (en) |
| DE (1) | DE2722917A1 (en) |
| DK (1) | DK218777A (en) |
| FI (1) | FI771587A (en) |
| FR (1) | FR2426460A1 (en) |
| GB (1) | GB1570993A (en) |
| IE (1) | IE45282B1 (en) |
| IL (1) | IL52102A0 (en) |
| LU (1) | LU77369A1 (en) |
| NL (1) | NL7705560A (en) |
| NO (1) | NO771765L (en) |
| NZ (1) | NZ184141A (en) |
| SE (1) | SE7705850L (en) |
| ZA (1) | ZA772989B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1595220A (en) * | 1977-12-23 | 1981-08-12 | Fisons Ltd | Tablets containing 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxypropane |
| US5447728A (en) * | 1992-06-15 | 1995-09-05 | Emisphere Technologies, Inc. | Desferrioxamine oral delivery system |
| CZ20032959A3 (en) | 2001-05-01 | 2004-01-14 | Pfizer Products Inc. | Process for preparing a pharmaceutical composition with low dosage of a medicament and having uniform distribution and efficiency of the medicament |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA753210B (en) * | 1974-06-14 | 1976-04-28 | Upjohn Co | Novel dosing regimen for intal biologues |
| IE41922B1 (en) * | 1974-11-09 | 1980-04-23 | Fisons Ltd | Pharmaceutical compositions containing bis-chromones |
| AT351530B (en) * | 1974-11-30 | 1979-07-25 | Fisons Ltd | PROCESS FOR THE PREPARATION OF NEW PYRAN-2-CARBONIC ACIDS, THEIR SALT, ESTER, AMIDES AND OPTICAL ISOMERS |
-
1976
- 1976-05-21 GB GB20984/76A patent/GB1570993A/en not_active Expired
-
1977
- 1977-05-16 IL IL52102A patent/IL52102A0/en unknown
- 1977-05-16 FR FR7714858A patent/FR2426460A1/en active Granted
- 1977-05-16 BE BE177619A patent/BE854690A/en unknown
- 1977-05-17 SE SE7705850A patent/SE7705850L/en unknown
- 1977-05-17 AU AU25214/77A patent/AU511269B2/en not_active Expired
- 1977-05-18 NZ NZ184141A patent/NZ184141A/en unknown
- 1977-05-18 DK DK218777A patent/DK218777A/en not_active Application Discontinuation
- 1977-05-18 LU LU77369A patent/LU77369A1/xx unknown
- 1977-05-18 ZA ZA00772989A patent/ZA772989B/en unknown
- 1977-05-19 JP JP5712777A patent/JPS52143220A/en active Pending
- 1977-05-19 CA CA278,833A patent/CA1105835A/en not_active Expired
- 1977-05-19 FI FI771587A patent/FI771587A/fi not_active Application Discontinuation
- 1977-05-20 NO NO771765A patent/NO771765L/en unknown
- 1977-05-20 NL NL7705560A patent/NL7705560A/en not_active Application Discontinuation
- 1977-05-20 DE DE19772722917 patent/DE2722917A1/en not_active Ceased
- 1977-05-20 IE IE1038/77A patent/IE45282B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1570993A (en) | 1980-07-09 |
| SE7705850L (en) | 1977-11-22 |
| NL7705560A (en) | 1977-11-23 |
| IL52102A0 (en) | 1977-07-31 |
| BE854690A (en) | 1977-11-16 |
| FI771587A (en) | 1977-11-22 |
| ZA772989B (en) | 1978-04-26 |
| LU77369A1 (en) | 1977-12-13 |
| DE2722917A1 (en) | 1977-12-01 |
| AU511269B2 (en) | 1980-08-07 |
| FR2426460A1 (en) | 1979-12-21 |
| NO771765L (en) | 1977-11-22 |
| DK218777A (en) | 1977-11-22 |
| AU2521477A (en) | 1978-11-23 |
| IE45282L (en) | 1977-11-21 |
| JPS52143220A (en) | 1977-11-29 |
| CA1105835A (en) | 1981-07-28 |
| NZ184141A (en) | 1979-06-19 |
| FR2426460B1 (en) | 1983-04-29 |
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