GB1582692A - Sulphonamide/trimethoprim solutions - Google Patents
Sulphonamide/trimethoprim solutions Download PDFInfo
- Publication number
- GB1582692A GB1582692A GB29575/77A GB2957577A GB1582692A GB 1582692 A GB1582692 A GB 1582692A GB 29575/77 A GB29575/77 A GB 29575/77A GB 2957577 A GB2957577 A GB 2957577A GB 1582692 A GB1582692 A GB 1582692A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polyvinylpyrrolidone
- solution
- trimethoprim
- mixture
- value
- 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
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 title claims description 46
- 229960001082 trimethoprim Drugs 0.000 title claims description 46
- 229940124530 sulfonamide Drugs 0.000 title claims description 21
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 59
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 59
- 239000000243 solution Substances 0.000 claims description 59
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 58
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 150000003456 sulfonamides Chemical class 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 16
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 16
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 15
- CYFLXLSBHQBMFT-UHFFFAOYSA-N sulfamoxole Chemical compound O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=C(N)C=C1 CYFLXLSBHQBMFT-UHFFFAOYSA-N 0.000 claims description 15
- YZMCKZRAOLZXAZ-UHFFFAOYSA-N sulfisomidine Chemical compound CC1=NC(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 YZMCKZRAOLZXAZ-UHFFFAOYSA-N 0.000 claims description 15
- 229960001975 sulfisomidine Drugs 0.000 claims description 15
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 13
- 229960001363 sulfamoxole Drugs 0.000 claims description 13
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 12
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 12
- 235000010265 sodium sulphite Nutrition 0.000 claims description 12
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 10
- 239000004615 ingredient Substances 0.000 claims description 8
- 239000002674 ointment Substances 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 108010010803 Gelatin Proteins 0.000 claims description 5
- 239000008273 gelatin Substances 0.000 claims description 5
- 229920000159 gelatin Polymers 0.000 claims description 5
- 235000019322 gelatine Nutrition 0.000 claims description 5
- 235000011852 gelatine desserts Nutrition 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 150000001451 organic peroxides Chemical class 0.000 claims description 5
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 4
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 4
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 4
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 claims description 4
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 4
- 229950004959 sorbitan oleate Drugs 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 235000015110 jellies Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 235000010268 sodium methyl p-hydroxybenzoate Nutrition 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000008274 jelly Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
- 229960005404 sulfamethoxazole Drugs 0.000 description 6
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 6
- 229960000686 benzalkonium chloride Drugs 0.000 description 5
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920000058 polyacrylate Polymers 0.000 description 5
- -1 sulfamethoxazole Chemical class 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 229940057995 liquid paraffin Drugs 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229960000541 cetyl alcohol Drugs 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000003889 eye drop Substances 0.000 description 3
- 229940012356 eye drops Drugs 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003978 infusion fluid Substances 0.000 description 3
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 3
- 235000019477 peppermint oil Nutrition 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- 239000003871 white petrolatum Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920002907 Guar gum Polymers 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 239000003221 ear drop Substances 0.000 description 2
- 229940047652 ear drops Drugs 0.000 description 2
- 239000003885 eye ointment Substances 0.000 description 2
- 239000000665 guar gum Substances 0.000 description 2
- 235000010417 guar gum Nutrition 0.000 description 2
- 229960002154 guar gum Drugs 0.000 description 2
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 125000002081 peroxide group Chemical group 0.000 description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 2
- 239000000286 vaginal jelly Substances 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- QSCDJPXGCZNSNJ-UHFFFAOYSA-N 4-amino-n-(4,5-dimethyl-1,3-oxazol-2-yl)benzenesulfonamide;5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=C(N)C=C1.COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 QSCDJPXGCZNSNJ-UHFFFAOYSA-N 0.000 description 1
- WZRJTRPJURQBRM-UHFFFAOYSA-N 4-amino-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide;5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1.COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 WZRJTRPJURQBRM-UHFFFAOYSA-N 0.000 description 1
- 150000005168 4-hydroxybenzoic acids Chemical class 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001599 direct drying Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940100657 nasal ointment Drugs 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004290 sodium methyl p-hydroxybenzoate Substances 0.000 description 1
- 229940001482 sodium sulfite Drugs 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229940006995 sulfamethoxazole and trimethoprim Drugs 0.000 description 1
- 229940007000 sulfamoxole and trimethoprim Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940044950 vaginal gel Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2631780A DE2631780C3 (de) | 1976-07-15 | 1976-07-15 | Sulfonamid-Trimethoprim-Lösungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1582692A true GB1582692A (en) | 1981-01-14 |
Family
ID=5983056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29575/77A Expired GB1582692A (en) | 1976-07-15 | 1977-07-14 | Sulphonamide/trimethoprim solutions |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5312416A (enrdf_load_stackoverflow) |
| BE (1) | BE856847A (enrdf_load_stackoverflow) |
| DE (1) | DE2631780C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2361103A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1582692A (enrdf_load_stackoverflow) |
| IN (1) | IN145551B (enrdf_load_stackoverflow) |
| ZA (1) | ZA774215B (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5008255A (en) * | 1989-01-12 | 1991-04-16 | Alcon Laboratories, Inc. | Method for enhancing solubility of trimethoprim with sodium sulfacetamide, and synergistic pharmaceutical compositions derived therefrom |
| EP1025858A4 (en) * | 1998-08-28 | 2009-03-11 | Eisai R&D Man Co Ltd | DRUGS WITH REDUCED BITTERNESS ETC. |
| CN113952296A (zh) * | 2021-11-15 | 2022-01-21 | 山东新华制药股份有限公司 | 一种复方磺胺甲噁唑注射液的制备方法 |
| CN116098909A (zh) * | 2023-02-14 | 2023-05-12 | 中牧全药(南京)动物药品有限公司 | 磺胺嘧啶二甲氧苄啶混悬液及其制备方法 |
| CN117599069A (zh) * | 2023-12-15 | 2024-02-27 | 江苏福润德科技有限公司 | 复方磺胺嘧啶混悬液的生产工艺 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54148019A (en) * | 1978-05-11 | 1979-11-19 | Tanto Kk | Binding and joining material for porcelain tile |
| EP0009559B1 (de) * | 1978-08-01 | 1982-08-25 | Ciba-Geigy Ag | Stabile flüssige Arzneimittelformulierung, ihre Herstellung und Verwendung |
| DE2963408D1 (en) * | 1978-08-01 | 1982-09-16 | Ciba Geigy Ag | Stable medicinal solution on the basis of 2,6-diamino-5-(3',4',5'-trimethoxybenzyl)-pyrimidine(trimethoprim) and a sulphonamide, process for preparing and using it |
| JPS55102517A (en) * | 1979-01-30 | 1980-08-05 | Shionogi & Co Ltd | Preparation of sulfamethoxazole-trimethoprim complex for administration via body cavity |
| JPS6196812A (ja) * | 1984-10-17 | 1986-05-15 | Murata Mfg Co Ltd | 電子部品 |
| US5510387A (en) * | 1992-11-16 | 1996-04-23 | Nikolai Borisovich Leonidov | Antimicrobial interferon-inducing medicament |
| WO1994010977A1 (en) * | 1992-11-16 | 1994-05-26 | Leonidov Nikolai B | Anti-microbial and interferon-inducing pharmaceutical compound |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE642734A (enrdf_load_stackoverflow) * | 1963-02-08 | |||
| CH544053A (de) * | 1966-05-09 | 1973-11-15 | Hoffmann La Roche | Verfahren zur Herstellung von Sulfonamidderivaten |
| GB1361491A (en) * | 1971-06-05 | 1974-07-24 | Pfizer Ltd | Process for the production of oxytetracycline solutions |
| GB1538903A (en) * | 1975-04-11 | 1979-01-24 | Nelson Res & Dev | Carrier for a topically applied physiologically active agent or cosmetic agent |
| DE2538678A1 (de) * | 1975-08-30 | 1977-03-03 | Boehringer Mannheim Gmbh | Injizierbare loesungen |
| DK136934B (da) * | 1976-02-06 | 1977-12-19 | Rosco As | Fremgangsmåde til fremstilling af en klar, stabil, injicerbar opløsning indeholdende et sulfonamid og en potentiator. |
| DE2627706C2 (de) * | 1976-06-21 | 1982-11-18 | Saarstickstoff-Fatol Gmbh, 6685 Schiffweiler | Verfahren zur Herstellung von neutralen beständigen, mit Wasser zu klaren Lösungen verdünnbaren Sulfonamid-Potentiatorlösungen |
-
1976
- 1976-07-15 DE DE2631780A patent/DE2631780C3/de not_active Expired
-
1977
- 1977-06-27 IN IN960/CAL/77A patent/IN145551B/en unknown
- 1977-07-12 FR FR7721535A patent/FR2361103A1/fr active Granted
- 1977-07-14 GB GB29575/77A patent/GB1582692A/en not_active Expired
- 1977-07-14 ZA ZA00774215A patent/ZA774215B/xx unknown
- 1977-07-15 BE BE179371A patent/BE856847A/xx unknown
- 1977-07-15 JP JP8434477A patent/JPS5312416A/ja active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5008255A (en) * | 1989-01-12 | 1991-04-16 | Alcon Laboratories, Inc. | Method for enhancing solubility of trimethoprim with sodium sulfacetamide, and synergistic pharmaceutical compositions derived therefrom |
| EP1025858A4 (en) * | 1998-08-28 | 2009-03-11 | Eisai R&D Man Co Ltd | DRUGS WITH REDUCED BITTERNESS ETC. |
| CN113952296A (zh) * | 2021-11-15 | 2022-01-21 | 山东新华制药股份有限公司 | 一种复方磺胺甲噁唑注射液的制备方法 |
| CN113952296B (zh) * | 2021-11-15 | 2023-10-13 | 山东新华制药股份有限公司 | 一种复方磺胺甲噁唑注射液的制备方法 |
| CN116098909A (zh) * | 2023-02-14 | 2023-05-12 | 中牧全药(南京)动物药品有限公司 | 磺胺嘧啶二甲氧苄啶混悬液及其制备方法 |
| CN116098909B (zh) * | 2023-02-14 | 2024-05-24 | 中牧全药(南京)动物药品有限公司 | 磺胺嘧啶二甲氧苄啶混悬液及其制备方法 |
| CN117599069A (zh) * | 2023-12-15 | 2024-02-27 | 江苏福润德科技有限公司 | 复方磺胺嘧啶混悬液的生产工艺 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2631780B2 (de) | 1980-10-09 |
| FR2361103B1 (enrdf_load_stackoverflow) | 1981-04-30 |
| ZA774215B (en) | 1978-07-26 |
| DE2631780C3 (de) | 1981-11-19 |
| JPS5312416A (en) | 1978-02-03 |
| BE856847A (fr) | 1978-01-16 |
| DE2631780A1 (de) | 1978-01-19 |
| IN145551B (enrdf_load_stackoverflow) | 1978-11-04 |
| FR2361103A1 (fr) | 1978-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |