CA1104931A - Compose pharmaceutique contenant de la sulphasalazine - Google Patents

Compose pharmaceutique contenant de la sulphasalazine

Info

Publication number: CA1104931A
Authority: CA; Canada
Prior art keywords: sulphasalazine; composition according; bis; active ingredient; propan
Prior art date: 1977-05-25
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

Application number

CA304,122A

Other languages

English (en)

Inventor

John L. Worsley

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Fisons Ltd

Original Assignee

Fisons Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-05-25

Filing date

1978-05-25

Publication date

1981-07-14

1978-05-25 Application filed by Fisons Ltd filed Critical Fisons Ltd

1981-07-14 Application granted granted Critical

1981-07-14 Publication of CA1104931A publication Critical patent/CA1104931A/fr

Status Expired legal-status Critical Current

Links

NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 title claims abstract description 26
229960001940 sulfasalazine Drugs 0.000 title claims abstract description 26
239000008194 pharmaceutical composition Substances 0.000 title claims abstract 4
239000000203 mixture Substances 0.000 claims abstract description 31
239000004480 active ingredient Substances 0.000 claims abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 11
229960000265 cromoglicic acid Drugs 0.000 claims abstract description 10
-1 activity Chemical compound 0.000 claims abstract description 5
230000000694 effects Effects 0.000 claims abstract description 5
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 claims abstract 8
150000003839 salts Chemical class 0.000 claims description 15
159000000000 sodium salts Chemical class 0.000 claims description 6
241000792859 Enema Species 0.000 claims description 4
239000007920 enema Substances 0.000 claims description 4
239000000829 suppository Substances 0.000 claims description 3
239000002552 dosage form Substances 0.000 claims description 2
229940095399 enema Drugs 0.000 claims description 2
239000012730 sustained-release form Substances 0.000 claims 1
VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 7
150000002148 esters Chemical class 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
241000124008 Mammalia Species 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
239000002245 particle Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
206010002198 Anaphylactic reaction Diseases 0.000 description 3
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 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
230000036783 anaphylactic response Effects 0.000 description 3
208000003455 anaphylaxis Diseases 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
210000001035 gastrointestinal tract Anatomy 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
238000000034 method Methods 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
241000894007 species Species 0.000 description 3
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
QFZTUWOWMRNMAH-UHFFFAOYSA-N 2h-pyran-2-carboxylic acid Chemical compound OC(=O)C1OC=CC=C1 QFZTUWOWMRNMAH-UHFFFAOYSA-N 0.000 description 2
208000011231 Crohn disease Diseases 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
206010036774 Proctitis Diseases 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
229940079360 enema for constipation Drugs 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
239000001993 wax Substances 0.000 description 2
JXYWFNAQESKDNC-BTJKTKAUSA-N (z)-4-hydroxy-4-oxobut-2-enoate;2-[(4-methoxyphenyl)methyl-pyridin-2-ylamino]ethyl-dimethylazanium Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 JXYWFNAQESKDNC-BTJKTKAUSA-N 0.000 description 1
BNRANURXPKRRKP-UHFFFAOYSA-N 1-[tert-butyl-[(4-methylphenyl)methyl]amino]-3-(1H-indol-4-yloxy)propan-2-ol Chemical compound Cc1ccc(CN(CC(O)COc2cccc3[nH]ccc23)C(C)(C)C)cc1 BNRANURXPKRRKP-UHFFFAOYSA-N 0.000 description 1
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
AUWRVKYHBXGIBK-UHFFFAOYSA-N 2-propyl-3,4-dihydronaphthalen-1-ol Chemical compound C(CC)C1=C(C2=CC=CC=C2CC1)O AUWRVKYHBXGIBK-UHFFFAOYSA-N 0.000 description 1
RVMGXWBCQGAWBR-UHFFFAOYSA-N 4-oxo-1-benzopyran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC(=O)C2=C1 RVMGXWBCQGAWBR-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000015943 Coeliac disease Diseases 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
239000001836 Dioctyl sodium sulphosuccinate Substances 0.000 description 1
208000007882 Gastritis Diseases 0.000 description 1
206010070840 Gastrointestinal tract irritation Diseases 0.000 description 1
206010018910 Haemolysis Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
206010040914 Skin reaction Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 1
239000007983 Tris buffer Substances 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
NYISNZSBPTZPPA-UHFFFAOYSA-N [H]C([H])([H])C([H])([H])C([H])([H])[Cr] Chemical compound [H]C([H])([H])C([H])([H])C([H])([H])[Cr] NYISNZSBPTZPPA-UHFFFAOYSA-N 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
102000030621 adenylate cyclase Human genes 0.000 description 1
108060000200 adenylate cyclase Proteins 0.000 description 1
XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229940081734 cellulose acetate phthalate Drugs 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
FIMJSWFMQJGVAM-UHFFFAOYSA-N chloroform;hydrate Chemical compound O.ClC(Cl)Cl FIMJSWFMQJGVAM-UHFFFAOYSA-N 0.000 description 1
OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
150000004777 chromones Chemical class 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229940061607 dibasic sodium phosphate Drugs 0.000 description 1
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000009501 film coating Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
201000005298 gastrointestinal allergy Diseases 0.000 description 1
125000005908 glyceryl ester group Chemical group 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002489 hematologic effect Effects 0.000 description 1
230000008588 hemolysis Effects 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
210000002011 intestinal secretion Anatomy 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002641 lithium Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002916 oxazoles Chemical class 0.000 description 1
238000012856 packing Methods 0.000 description 1
150000002943 palmitic acids Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
231100000430 skin reaction Toxicity 0.000 description 1
230000035483 skin reaction Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
206010043554 thrombocytopenia Diseases 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
239000011579 vitamin B4 Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000007964 xanthones Chemical class 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
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
- 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
- A61K31/655—Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds

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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA304,122A 1977-05-25 1978-05-25 Compose pharmaceutique contenant de la sulphasalazine Expired CA1104931A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB2197577		1977-05-25
GB21975/77		1977-05-25

Publications (1)

Publication Number	Publication Date
CA1104931A true CA1104931A (fr)	1981-07-14

Family

ID=10171891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA304,122A Expired CA1104931A (fr)	1977-05-25	1978-05-25	Compose pharmaceutique contenant de la sulphasalazine

Country Status (3)

Country	Link
BE (1)	BE867334A (fr)
CA (1)	CA1104931A (fr)
ZA (1)	ZA782993B (fr)

1978
- 1978-05-22 BE BE187920A patent/BE867334A/fr not_active IP Right Cessation
- 1978-05-24 ZA ZA00782993A patent/ZA782993B/xx unknown
- 1978-05-25 CA CA304,122A patent/CA1104931A/fr not_active Expired

Also Published As

Publication number	Publication date
ZA782993B (en)	1979-05-30
BE867334A (fr)	1978-11-22

Legal Events

Date	Code	Title	Description
1998-07-14	MKEX	Expiry

Publication	Publication Date	Title
CA1093970A (fr)	1981-01-20	Traduction non-disponible
ES2661723T3 (es)	2018-04-03	Forma galénica oral microparticulada para la liberación retardada y controlada de principios activos farmacéuticos
US4289751A (en)	1981-09-15	Effervescent enteric-coated formulation of soluble form of erythromycin and therapeutic use thereof
ES2463421T3 (es)	2014-05-27	Formulaciones de fármaco que tienen potencial adictivo reducido
DE69205971T2 (de)	1996-04-11	Orale dosierungsform mit verzögerter wirkstoffabgabe für die behandlung von intestinalen krankheiten.
JP2007532689A (ja)	2007-11-15	医薬有効成分の遅延性かつ調節性放出のための微粒子経口ガレヌス製剤
ES2529570T3 (es)	2015-02-23	Formulaciones multiparticuladas de pantoprazol
US5229134A (en)	1993-07-20	Pharmaceutical compositions
US4874613A (en)	1989-10-17	Taste concealing pharmaceutical dosage unit
US4702918A (en)	1987-10-27	Pharmaceutical preparations and a method of manufacturing them
US4765990A (en)	1988-08-23	Sustained-release nifedipine preparation
EP0640337B1 (fr)	2003-05-07	Composition pharmaceutique avec commencement et vitesse contrôlés de la libération
DE60132600T2 (de)	2009-01-29	Medikamente zur chemotherapeutischen behandlung von erkrankungen
PT85353B (pt)	1990-04-30	Processo de preparacao de composicoes farmaceuticas de libertacao controlada e de matriz a base de alcool alifatico e resina acrilica
ATE217188T1 (de)	2002-05-15	Granulierte pharmazeutische zusammensetzung
EP0871434B2 (fr)	2007-12-12	Composition pharmaceutique orale a liberation modifiee contenant 5-asa et procede de traitement de maladies intestinales
RU98111765A (ru)	2000-05-20	Фармацевтическая композиция для орального введения с модифицированным высвобождением, содержащая 5-аск, и способ лечения кишечных заболеваний
KR20030048410A (ko)	2003-06-19	경구투여용 조절방출배합물
ES2301635T3 (es)	2008-07-01	Derivados de la cumarina para su utilizacion como anticoagulantes.
KR900015724A (ko)	1990-11-10	메베버린 용량 형태
CA2083385C (fr)	2000-02-22	Suppositoire a degagement prolonge
JPH0148247B2 (fr)	1989-10-18
CA1104931A (fr)	1981-07-14	Compose pharmaceutique contenant de la sulphasalazine
BR112014013374B1 (pt)	2022-10-11	Comprimidos de acamprosato e usos de acamprosato referência cruzada aos pedidos relacionados
CA1099641A (fr)	1981-04-21	Traduction non-disponible