US3577549A - Treatment of pain or inflammation with p-benzoyl-phenylacetic acid or o-benzoyl-phenylacetic acid - Google Patents
Treatment of pain or inflammation with p-benzoyl-phenylacetic acid or o-benzoyl-phenylacetic acid Download PDFInfo
- Publication number
- US3577549A US3577549A US751379A US3577549DA US3577549A US 3577549 A US3577549 A US 3577549A US 751379 A US751379 A US 751379A US 3577549D A US3577549D A US 3577549DA US 3577549 A US3577549 A US 3577549A
- Authority
- US
- United States
- Prior art keywords
- benzoyl
- phenylacetic acid
- weight
- tablets
- treatment
- 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 - Lifetime
Links
- ILZOEMNCWIVMLT-UHFFFAOYSA-N 2-(4-benzoylphenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C(=O)C1=CC=CC=C1 ILZOEMNCWIVMLT-UHFFFAOYSA-N 0.000 title description 8
- RWOPZYIDUDXHIB-UHFFFAOYSA-N 2-(2-benzoylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1C(=O)C1=CC=CC=C1 RWOPZYIDUDXHIB-UHFFFAOYSA-N 0.000 title description 2
- 206010061218 Inflammation Diseases 0.000 title description 2
- 230000004054 inflammatory process Effects 0.000 title description 2
- 239000003826 tablet Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 9
- 239000006188 syrup Substances 0.000 description 8
- 235000020357 syrup Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 4
- 235000019759 Maize starch Nutrition 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- PASHVRUKOFIRIK-UHFFFAOYSA-L calcium sulfate dihydrate Chemical compound O.O.[Ca+2].[O-]S([O-])(=O)=O PASHVRUKOFIRIK-UHFFFAOYSA-L 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229960003424 phenylacetic acid Drugs 0.000 description 4
- 239000003279 phenylacetic acid Substances 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- -1 ammonium ions Chemical class 0.000 description 3
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000002662 enteric coated tablet Substances 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- YVKSMFUEDUPYIF-UHFFFAOYSA-N 3-oxo-2,3-diphenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C(=O)C1=CC=CC=C1 YVKSMFUEDUPYIF-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 101800004538 Bradykinin Proteins 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102100035792 Kininogen-1 Human genes 0.000 description 1
- 108010093008 Kinins Proteins 0.000 description 1
- 102000002397 Kinins Human genes 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229960001777 castor oil Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
Definitions
- the daily dose of the active ingredient may be from about 25 to 750 mg. per day depending on the age, weight, and condition of the patient.
- the present invention accordingly provides pharmaceutical compositions valuable in the treatment of inflamma- David Jack and Deryck Rhodes, London, England, as- 5 signors to Allen & Hanburys Limited, London, England tory conditions and also in conditions where the use of an No Drawing. Filed Aug. 9, 1968, Ser. No. 751,379 analgesic or antipyretic agent is indicated. Claims P y, application Great Britain, Allg- 1967, The compositions may be formulated for use in human 38,424/67 and veterinary medicine for therapeutic purposes.
- the unit dosage f may contain 5 250 mg f ingredients have anti-inflammatory and analgetic activity.
- the active ingredient They may be administered in dosage unit form-
- the carrier or diluent may be solid or a liquid.
- the composition of the present invention may exist in the form of, for example, capsules, supposi
- This invention relates to Pharmaceutical P tories or tablets which may include binders and lubricants More Particularly it relalfis i0 pharmaifeutical Composi' and which may be coated.
- the composition may be in unit dosage form, such geslc actlyltyas sterile solutions in ampoules for parenteral administra-
- the Compositions Provided y this invention Contain tion or solutions or suspensions in soft gelatine capsules as active ingredient either P' y -p y acid of for oral administration, or the compositions may be for Formula I o'benloyl-phenylacetic acid of Formula II example, suspensions or solutions for 'oral administration.
- ples of salts are those wherein the acidic hydrogen in the p-Benzoyl-phenylacetic acid 1,000 acids of Formulae I and II are replaced by one equivalent Calcium sulphate dihydrate 750 of a cation of an alkali metal such as sodium or potas- Dry maize starch 240 sium.
- Non-metallic cations include the ammonium ion, Magnesium stearate l0 substituted organic ammonium ions derived from primary secondary and tertiary amines and quaternary ammonium of Powdered P'benzoyl"phen ylacetlc acld was ions mixed with 750 g.
- Magnesium stearate 100 10 kg. of powdered p-benzoyl-phenyl acetic acid was mixed with 7.5 kg. of calcium sulphate dihydrate and sufficient of a solution of low viscosity sodium carboxymethylcellulose to produce a damp cohesive mass. This was granulated by passing through a 16 mesh sieve. The granules were dried at 4550 C. and passed through a 20 mesh sieve. The sieved granules were mixed with 2.4 kg. of maize starch and 100 g. of magnesium stearate. The lubricated granules were compressed on a suitable tablet machine using diameter deep concave punches to produce tablets of average weight about 200 mg. for coating.
- the tablet cores were placed in a coating pan of suitable size. 200 ml. of a solution containing by weight of a polyvinylpyrrolidone and 2% by weight of polyethylene glycol 6000 in 66 o.p. industrial alcohol was applied. The solvents were caused to evaporate by means of cold air and the operation was repeated. The cores were heated to 45 C. by means of hot air and 200 ml. of a syrup containing 12% by weight of acacia gum and 66% by weight of sucrose applied. The tablets were allowed to roll until they were evenly coated with the syrup and were then dried by means of heated air. The last step was then repeated.
- the sugar coating was continued using a syrup containing 60% by weight of sucrose and 15% by weight of calcium phosphate until the average tablet weight was about 325 mg. Coating was continued using a syrup containing 66% by weight of sucrose and a suitable colouring agent until the average tablet weight was 350 mg. Finally the tablets were polished using conventionla techniques.
- EXAMPLE 3 Tablets 100,000 enteric coated tablets each containing 100 mg. of p-benzoyl-phenyl acetic acid were prepared in the following way:
- the tablet cores were prepared as in Example 2 above.
- the cores were rotated in a suitable coating pan and 200 ml. of a solution containing 10% by weight of a polyvinylpyrrolidone and 2% by weight of polyethylene glycol 6000 in 66 o.p. industrial alcohol was applied.
- the solvents were caused to evaporate by means of cold air and the operation was repeated.
- a film of cellulose acetate phthalate suitably plasticised was applied in a similar manner suflicient to enable the tablets to conform to the distintegration test for enteric coated tablets of the British Pharmacopoeia 1963, p. 1158.
- the cellulose acetate phthalate was applied in solution in suitable mixed solvents such as acetone/ alcohol mixtures containing non toxic plasticisers such as castor oil, benzyl benzoate or glyceryl triacetate.
- suitable mixed solvents such as acetone/ alcohol mixtures containing non toxic plasticisers such as castor oil, benzyl benzoate or glyceryl triacetate.
- o-Benzoyl-phenylacetic acid may be substituted for pbenzoyl-phenylacetic acid in the above examples.
- a method of treating a patient requiring analgetic or antiinflammatory treatment which comprises administering to said patient an analgesically and antiinflammatory effective non-toxic dose of a pharmaceutical composition comprising as active ingredient a member selected from the group consisting of p-benzoylphenylacetic acid, 0- benzoylphenylacetic acid, and physiologically acceptable salts thereof together with a pharmaceutically acceptable carrier.
- composition is administered orally to the patient.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB38424/67A GB1195294A (en) | 1967-08-21 | 1967-08-21 | Improvements in or relating to Pharmaceutical Compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3577549A true US3577549A (en) | 1971-05-04 |
Family
ID=10403346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US751379A Expired - Lifetime US3577549A (en) | 1967-08-21 | 1968-08-09 | Treatment of pain or inflammation with p-benzoyl-phenylacetic acid or o-benzoyl-phenylacetic acid |
Country Status (7)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4159986A (en) * | 1969-11-12 | 1979-07-03 | Roussel Uclaf | Novel thiophene-acetic acids |
| US4318918A (en) * | 1975-07-28 | 1982-03-09 | Roussel Uclaf | Novel salt of 5-(benzoyl)-thiophene-2-α-methyl-acetic acid |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT380166B (de) * | 1981-02-16 | 1986-04-25 | Ciba Geigy Ag | Verfahren zur herstellung topisch applizierbarer pharmazeutischer praeparate, enthaltend salze von alkancarbonsaeuren |
| AR242947A1 (es) * | 1983-06-15 | 1993-06-30 | Ciba Geigy | Procedimiento para la obtencion de derivados de acidos 4-benzoil-5-hidroxi-benzoilciclobuten-1-carboxilico y sus sales. |
-
1967
- 1967-08-21 GB GB38424/67A patent/GB1195294A/en not_active Expired
-
1968
- 1968-08-02 IE IE938/68A patent/IE32260B1/xx unknown
- 1968-08-02 BE BE718959D patent/BE718959A/xx unknown
- 1968-08-04 IL IL30488A patent/IL30488A/xx unknown
- 1968-08-08 NL NL6811322A patent/NL6811322A/xx unknown
- 1968-08-09 US US751379A patent/US3577549A/en not_active Expired - Lifetime
- 1968-08-20 FR FR163475A patent/FR7947M/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4159986A (en) * | 1969-11-12 | 1979-07-03 | Roussel Uclaf | Novel thiophene-acetic acids |
| US4318918A (en) * | 1975-07-28 | 1982-03-09 | Roussel Uclaf | Novel salt of 5-(benzoyl)-thiophene-2-α-methyl-acetic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| IE32260B1 (en) | 1973-05-30 |
| BE718959A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-02-03 |
| IL30488A (en) | 1974-05-16 |
| NL6811322A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-02-25 |
| IL30488A0 (en) | 1968-10-24 |
| GB1195294A (en) | 1970-06-17 |
| FR7947M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-05-25 |
| IE32260L (en) | 1969-02-21 |
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