CS212740B2 - Method of preparing clear solutions for parenteral administration - Google Patents
Method of preparing clear solutions for parenteral administration Download PDFInfo
- Publication number
- CS212740B2 CS212740B2 CS7435A CS3574A CS212740B2 CS 212740 B2 CS212740 B2 CS 212740B2 CS 7435 A CS7435 A CS 7435A CS 3574 A CS3574 A CS 3574A CS 212740 B2 CS212740 B2 CS 212740B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- water
- solution
- formula
- sulfonamide
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 35
- 238000007911 parenteral administration Methods 0.000 title claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 229940124530 sulfonamide Drugs 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 22
- -1 2-pyrimidyl Chemical group 0.000 claims description 18
- 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 claims description 17
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 claims description 3
- 229960000973 sulfadimethoxine Drugs 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- LDBTVAXGKYIFHO-UHFFFAOYSA-N diaveridine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CN=C(N)N=C1N LDBTVAXGKYIFHO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims 1
- 229960004306 sulfadiazine Drugs 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 8
- 239000007924 injection Substances 0.000 abstract description 8
- 239000007864 aqueous solution Substances 0.000 abstract description 4
- 238000001802 infusion Methods 0.000 abstract description 3
- 230000000451 tissue damage Effects 0.000 abstract description 3
- 231100000827 tissue damage Toxicity 0.000 abstract description 3
- 210000003462 vein Anatomy 0.000 abstract description 3
- 230000035602 clotting Effects 0.000 abstract description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 2
- IQIWPLPOZHJNMX-UHFFFAOYSA-N 2-methyl-3-phenylpropanenitrile Chemical compound N#CC(C)CC1=CC=CC=C1 IQIWPLPOZHJNMX-UHFFFAOYSA-N 0.000 abstract 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 1
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 71
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 46
- 239000000203 mixture Substances 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 230000003389 potentiating effect Effects 0.000 description 15
- 229960001082 trimethoprim Drugs 0.000 description 14
- 229960005404 sulfamethoxazole Drugs 0.000 description 13
- 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 13
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 12
- 229960004106 citric acid Drugs 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 229960004543 anhydrous citric acid Drugs 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 description 4
- 229960002673 sulfacetamide Drugs 0.000 description 4
- 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 class 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 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 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 3
- 230000000973 chemotherapeutic effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 241000167854 Bourreria succulenta Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 235000019693 cherries Nutrition 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000003978 infusion fluid Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 2
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-UHFFFAOYSA-N 0.000 description 2
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- IEAAAQXTROJCRL-UHFFFAOYSA-N 5-[(2,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound COC1=CC(OC)=C(OC)C=C1CC1=CN=C(N)N=C1N IEAAAQXTROJCRL-UHFFFAOYSA-N 0.000 description 1
- DGKKGLAEGKBLCW-UHFFFAOYSA-N 5-[(7-methoxy-1,3-benzodioxol-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2OCOC=2C(OC)=CC=1CC1=CN=C(N)N=C1N DGKKGLAEGKBLCW-UHFFFAOYSA-N 0.000 description 1
- RNWMSFXMEDHASR-UHFFFAOYSA-N 5-benzylpyridine-2,4-diamine Chemical class C1=NC(N)=CC(N)=C1CC1=CC=CC=C1 RNWMSFXMEDHASR-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 241000606790 Haemophilus Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 239000004285 Potassium sulphite Substances 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 206010037075 Protozoal infections Diseases 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007958 cherry flavor Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- SZMNOLSLNRNAJC-UHFFFAOYSA-N formaldehyde;propane-1,2,3-triol Chemical compound O=C.OCC(O)CO SZMNOLSLNRNAJC-UHFFFAOYSA-N 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- RAYLUPYCGGKXQO-UHFFFAOYSA-N n,n-dimethylacetamide;hydrate Chemical compound O.CN(C)C(C)=O RAYLUPYCGGKXQO-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003182 parenteral nutrition solution 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
- 239000002798 polar solvent Substances 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- QVOMDXSQDOBBMW-UHFFFAOYSA-L potassium metabisulphite Chemical compound [K+].[K+].[O-]S(=O)OS([O-])=O QVOMDXSQDOBBMW-UHFFFAOYSA-L 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002135 sulfadimidine Drugs 0.000 description 1
- 229960000654 sulfafurazole Drugs 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
-
- 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
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- 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)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB69073A GB1469521A (en) | 1973-01-05 | 1973-01-05 | Antimicrobial preparations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS212740B2 true CS212740B2 (en) | 1982-03-26 |
Family
ID=9708818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS7435A CS212740B2 (en) | 1973-01-05 | 1974-01-03 | Method of preparing clear solutions for parenteral administration |
Country Status (31)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1596044A (en) * | 1977-04-14 | 1981-08-19 | Wellcome Found | Veterinary compositions |
| DE2731013C2 (de) * | 1977-07-08 | 1982-07-15 | Lentia Gmbh | Verfahren zur Herstellung einer wäßrigen Infusionslösung |
| 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 |
| HU180740B (en) * | 1979-11-27 | 1983-04-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing sulfonamide-containing,injectable pharmaceutical composition of prolongated activity |
| CH647412A5 (de) * | 1980-03-25 | 1985-01-31 | Hoffmann La Roche | Pharmazeutische praeparate. |
| HU212498B (en) * | 1992-11-06 | 1996-07-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing water-soluble pharmaceutical compositions, containing sulfachlorpyridazin-sodium and trimethoprim |
| DE4331147A1 (de) | 1993-09-14 | 1995-03-16 | Nycomed Arzneimittel Gmbh | Intravenös verabreichbare, wäßrige Lösung |
| WO2018229659A1 (en) | 2017-06-13 | 2018-12-20 | 3M Innovative Properties Company | Modified polytetrafluoroethylene and aqueous dispersion containing the same |
| EP3527634A1 (en) | 2018-02-15 | 2019-08-21 | 3M Innovative Properties Company | Fluoropolymers and fluoropolymer dispersions |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1028204A (en) * | 1963-06-28 | 1966-05-04 | May & Baker Ltd | Veterinary coccidiostatic compositions |
| BR6915082D0 (pt) * | 1969-05-16 | 1973-03-08 | Wellcome Found | Processo de preparacao de benzil-pirimidinas |
| RO67383A (ro) * | 1970-10-22 | 1981-07-30 | The Wellcome Foundation Ltd,Gb | Procedeu pentru prepararea unor 2,4-diamino-5-benzilpirimidine |
| GB1407971A (en) * | 1971-04-16 | 1975-10-01 | Wellcome Found | 2,4-diamino -4-3,4,5-triethoxybenzyl pyrimidine and methods of preparation therefor |
| BE787236A (fr) * | 1971-08-05 | 1973-02-05 | Wellcome Found | Compositions de potentialisation |
-
1973
- 1973-01-05 GB GB69073A patent/GB1469521A/en not_active Expired
- 1973-12-27 ZM ZM201/73A patent/ZM20173A1/xx unknown
-
1974
- 1974-01-01 AR AR251788A patent/AR204521A1/es active
- 1974-01-02 AT AT2274*#A patent/AT331986B/de not_active IP Right Cessation
- 1974-01-02 HU HU74WE00000498A patent/HU171200B/hu unknown
- 1974-01-02 FI FI8/74A patent/FI55296C/fi active
- 1974-01-03 CS CS7435A patent/CS212740B2/cs unknown
- 1974-01-03 BE BE139505A patent/BE809378A/xx not_active IP Right Cessation
- 1974-01-03 DD DD175822A patent/DD111156A5/xx unknown
- 1974-01-03 CA CA189,371A patent/CA1014067A/en not_active Expired
- 1974-01-03 SE SE7400031A patent/SE430847B/xx not_active IP Right Cessation
- 1974-01-03 DK DK4074AA patent/DK138006B/da not_active IP Right Cessation
- 1974-01-03 IE IE10/74A patent/IE38713B1/xx unknown
- 1974-01-03 ZA ZA00740061A patent/ZA7461B/xx unknown
- 1974-01-03 DD DD182544A patent/DD115120A5/xx unknown
- 1974-01-03 AU AU64136/74A patent/AU472758B2/en not_active Expired
- 1974-01-03 DE DE2400218A patent/DE2400218A1/de not_active Withdrawn
- 1974-01-03 IN IN19/CAL/1974A patent/IN138511B/en unknown
- 1974-01-03 NO NO740022A patent/NO140578C/no unknown
- 1974-01-03 CH CH3574A patent/CH616930A5/de not_active IP Right Cessation
- 1974-01-03 FR FR7400111A patent/FR2213060B1/fr not_active Expired
- 1974-01-03 IL IL43954A patent/IL43954A/en unknown
- 1974-01-04 JP JP450774A patent/JPS5344531B2/ja not_active Expired
- 1974-01-04 MW MW1/74*UA patent/MW174A1/xx unknown
- 1974-01-04 NL NLAANVRAGE7400094,A patent/NL183927C/xx not_active IP Right Cessation
- 1974-01-05 PH PH7415374A patent/PH12388A/en unknown
- 1974-03-22 CY CY1070A patent/CY1070A/xx unknown
- 1974-06-07 ES ES427078A patent/ES427078A1/es not_active Expired
-
1979
- 1979-03-26 CH CH279379A patent/CH616931A5/de not_active IP Right Cessation
- 1979-03-26 CH CH279479A patent/CH628335A5/de not_active IP Right Cessation
- 1979-03-26 CH CH279579A patent/CH616932A5/de not_active IP Right Cessation
-
1980
- 1980-02-21 IT IT8047967A patent/IT8047967A0/it unknown
- 1980-07-12 KE KE3065A patent/KE3065A/xx unknown
- 1980-08-14 HK HK442/80A patent/HK44280A/xx unknown
-
1981
- 1981-12-30 MY MY146/81A patent/MY8100146A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3985876A (en) | Chemotherapeutic solutions containing a sulphur and a salt of a 2,4-diamino-5-benzylpyrimidine | |
| US5536735A (en) | Pharmaceutical composition | |
| HU226778B1 (en) | Injection and injection kit containing omeprazole and its analogs | |
| FI79944B (fi) | Oxikam-derivat innehaollande farmaceutiska kompositioner och deras framstaellningsfoerfarande. | |
| RU2000121556A (ru) | Новые трициклические производные (варианты), фармацевтическая композиция (варианты), способ подавления иммуной реакции или лечения и /или предупреждения аллергических заболеваний (варианты) | |
| HU194048B (en) | Process for producing liquide compositions containing dihydropyridines as active components | |
| CS212740B2 (en) | Method of preparing clear solutions for parenteral administration | |
| US6211185B1 (en) | Concentrate comprising a sulfonamide in solution, a 2,4-diaminopyrimidine in stable suspension within said solution, and a suspending agent | |
| FI87993C (fi) | Foerfarande foer framstaellning av alkaliska injektionsloesningar av torasemid innehaollande vatten, som aer faerdiga foer injicering | |
| NO168048B (no) | Dispersjonspolymerer, fremgangsmaate til deres fremstilling og deres anvendelse. | |
| SK5392002A3 (en) | Formulation of substituted benzimidazoles | |
| AU599034B2 (en) | Furosemide salts | |
| US4031214A (en) | Sulphonamide and 2,4-diaminopyrimidine injectable suspension | |
| JPH0216730B2 (enrdf_load_html_response) | ||
| KR880001751B1 (ko) | 설폰아미드-강화제 용액의 제조방법 | |
| KR840002014B1 (ko) | 약학적 제제의 제조방법 | |
| IE48607B1 (en) | Medicinal formulation | |
| NZ210247A (en) | Anthelmintic compositions containing levamisole derivatives | |
| EP0022342B1 (en) | Sulfonamide solutions | |
| US3278536A (en) | Pyrimethamine salt with 2, 6-dihydroxyisonicotinic acid | |
| US2463461A (en) | Aqueous solutions of riboflavin | |
| US3856971A (en) | Method of combating filariasis in dogs | |
| US20020183287A1 (en) | Method of producing a concentrate comprising a sulfonamide in solution, a 2,4-diaminopyrimidine in stable suspension within said solution | |
| RU2419431C1 (ru) | ПРОИЗВОДНЫЕ β-КАРБОЛИНА, ОБЛАДАЮЩИЕ ПРОТИВОТУБЕРКУЛЕЗНОЙ АКТИВНОСТЬЮ, ИХ ПРИМЕНЕНИЯ ДЛЯ ПРОИЗВОДСТВА ЛЕКАРСТВЕННОГО СРЕДСТВА, СПОСОБ ИХ СИНТЕЗА, А ТАКЖЕ НОВЫЕ МЕТОДЫ ЛЕЧЕНИЯ С ИХ ИСПОЛЬЗОВАНИЕМ | |
| DE2445400A1 (de) | Injizierbare therapeutische zubereitungen |