BE475834A - - Google Patents
Info
- Publication number
- BE475834A BE475834A BE475834DA BE475834A BE 475834 A BE475834 A BE 475834A BE 475834D A BE475834D A BE 475834DA BE 475834 A BE475834 A BE 475834A
- Authority
- BE
- Belgium
- Prior art keywords
- compound
- penicillin
- formula
- adjuvant
- group
- Prior art date
Links
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 130
- 239000002671 adjuvant Substances 0.000 claims description 127
- 230000000240 adjuvant Effects 0.000 claims description 127
- 229940049954 Penicillin Drugs 0.000 claims description 120
- 229960000626 benzylpenicillin Drugs 0.000 claims description 120
- 239000000203 mixture Substances 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- 230000036826 Excretion Effects 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 31
- 230000029142 excretion Effects 0.000 claims description 31
- 239000000047 product Substances 0.000 claims description 26
- -1 alkyl radical Chemical class 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 210000002381 Plasma Anatomy 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 9
- 210000003734 Kidney Anatomy 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 239000005711 Benzoic acid Substances 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 230000024924 glomerular filtration Effects 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 210000001035 Gastrointestinal Tract Anatomy 0.000 claims description 5
- 210000000738 Kidney Tubules Anatomy 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 230000001225 therapeutic Effects 0.000 claims description 5
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 210000002919 epithelial cells Anatomy 0.000 claims description 4
- 230000000268 renotropic Effects 0.000 claims description 4
- ISHFVIZDQFUPBN-UHFFFAOYSA-N 4-(pentylsulfamoyl)benzoic acid Chemical compound CCCCCNS(=O)(=O)C1=CC=C(C(O)=O)C=C1 ISHFVIZDQFUPBN-UHFFFAOYSA-N 0.000 claims description 3
- 238000010348 incorporation Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 231100000404 nontoxic agent Toxicity 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000000875 corresponding Effects 0.000 claims 2
- 239000012467 final product Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 230000003301 hydrolyzing Effects 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N Methyl radical Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N Methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000003159 antacid agent Substances 0.000 claims 1
- 230000001458 anti-acid Effects 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 230000002588 toxic Effects 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 239000000243 solution Substances 0.000 description 55
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
- 210000004369 Blood Anatomy 0.000 description 38
- 239000008280 blood Substances 0.000 description 38
- 239000002775 capsule Substances 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000003610 charcoal Substances 0.000 description 18
- FKHIFSZMMVMEQY-UHFFFAOYSA-N Talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 16
- 239000000391 magnesium silicate Substances 0.000 description 16
- 229940099273 magnesium trisilicate Drugs 0.000 description 16
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 16
- 235000019793 magnesium trisilicate Nutrition 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 239000008101 lactose Substances 0.000 description 11
- GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 229920002261 Corn starch Polymers 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000004320 controlled atmosphere Methods 0.000 description 8
- 239000008120 corn starch Substances 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-Ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 7
- 239000007937 lozenge Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000008188 pellet Substances 0.000 description 7
- 238000003379 elimination reaction Methods 0.000 description 6
- 238000001990 intravenous administration Methods 0.000 description 6
- 230000020477 pH reduction Effects 0.000 description 6
- 239000000454 talc Substances 0.000 description 6
- 235000012222 talc Nutrition 0.000 description 6
- 229910052623 talc Inorganic materials 0.000 description 6
- 229960000583 Acetic Acid Drugs 0.000 description 5
- 229920000569 Gum karaya Polymers 0.000 description 5
- 229940039371 Karaya Gum Drugs 0.000 description 5
- 241000934878 Sterculia Species 0.000 description 5
- 230000017531 blood circulation Effects 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000007927 intramuscular injection Substances 0.000 description 5
- 239000000231 karaya gum Substances 0.000 description 5
- 235000010494 karaya gum Nutrition 0.000 description 5
- BLFLLBZGZJTVJG-UHFFFAOYSA-N Benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 4
- IQFVPQOLBLOTPF-HKXUKFGYSA-L Congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002285 corn oil Substances 0.000 description 4
- 235000005687 corn oil Nutrition 0.000 description 4
- 201000009910 diseases by infectious agent Diseases 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000010255 intramuscular injection Methods 0.000 description 4
- 230000036470 plasma concentration Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-Aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L Calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
- OSASVXMJTNOKOY-UHFFFAOYSA-N Chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 3
- 229960004926 Chlorobutanol Drugs 0.000 description 3
- ZPWVASYFFYYZEW-UHFFFAOYSA-L Dipotassium phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 3
- HSMNQINEKMPTIC-UHFFFAOYSA-N N-(4-aminobenzoyl)glycine Chemical compound NC1=CC=C(C(=O)NCC(O)=O)C=C1 HSMNQINEKMPTIC-UHFFFAOYSA-N 0.000 description 3
- 208000008467 Subacute Bacterial Endocarditis Diseases 0.000 description 3
- 206010042276 Subacute endocarditis Diseases 0.000 description 3
- 229960004050 aminobenzoic acid Drugs 0.000 description 3
- 229960004567 aminohippuric acid Drugs 0.000 description 3
- 235000013539 calcium stearate Nutrition 0.000 description 3
- 239000008116 calcium stearate Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000011068 load Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 230000001698 pyrogenic Effects 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 3
- IUYFKLDRPZLAQQ-UHFFFAOYSA-N (3-nitrophenyl)methanesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(CS(Cl)(=O)=O)=C1 IUYFKLDRPZLAQQ-UHFFFAOYSA-N 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 235000016623 Fragaria vesca Nutrition 0.000 description 2
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N Hippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- IXNUSZATRHKNRW-UHFFFAOYSA-N NC=1C=C(CS(=O)(=O)NC2=CC=C(C(=O)O)C=C2)C=CC=1 Chemical compound NC=1C=C(CS(=O)(=O)NC2=CC=C(C(=O)O)C=C2)C=CC=1 IXNUSZATRHKNRW-UHFFFAOYSA-N 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 229940045860 White wax Drugs 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive Effects 0.000 description 2
- 235000012735 amaranth Nutrition 0.000 description 2
- 239000004178 amaranth Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- RERHJVNYJKZHLJ-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;2-(3,5-diiodo-4-oxopyridin-1-yl)acetate Chemical compound OCCNCCO.OC(=O)CN1C=C(I)C(=O)C(I)=C1 RERHJVNYJKZHLJ-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 210000004027 cells Anatomy 0.000 description 2
- 239000007891 compressed tablet Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- OWSFREMTZBBAKW-UHFFFAOYSA-N ethyl 4-(benzylsulfonylamino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NS(=O)(=O)CC1=CC=CC=C1 OWSFREMTZBBAKW-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000007970 homogeneous dispersion Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000000644 isotonic solution Substances 0.000 description 2
- 230000003000 nontoxic Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 235000010603 pastilles Nutrition 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- APGGSERFJKEWFG-UHFFFAOYSA-N 1-(chloromethyl)-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(CCl)=C1 APGGSERFJKEWFG-UHFFFAOYSA-N 0.000 description 1
- RVHDYDZMDKCAOE-UHFFFAOYSA-N 1-methyl-4-(4-nitrophenyl)sulfonylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 RVHDYDZMDKCAOE-UHFFFAOYSA-N 0.000 description 1
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- QIKUOKKSPSEHEY-UHFFFAOYSA-N 3-(benzylsulfonylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC(NS(=O)(=O)CC=2C=CC=CC=2)=C1 QIKUOKKSPSEHEY-UHFFFAOYSA-N 0.000 description 1
- MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 1
- LBCHJLKLZXSALP-UHFFFAOYSA-N 4-(2-phenylethylsulfonylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NS(=O)(=O)CCC1=CC=CC=C1 LBCHJLKLZXSALP-UHFFFAOYSA-N 0.000 description 1
- DVFCGSZRLJQHJA-UHFFFAOYSA-N 4-(4-aminophenoxy)benzoic acid Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(O)=O)C=C1 DVFCGSZRLJQHJA-UHFFFAOYSA-N 0.000 description 1
- ANJUQZCKLXYDJX-UHFFFAOYSA-N 4-(4-aminophenyl)sulfonylbenzoic acid Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 ANJUQZCKLXYDJX-UHFFFAOYSA-N 0.000 description 1
- SQJQLYOMPSJVQS-UHFFFAOYSA-N 4-(4-carboxyphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 SQJQLYOMPSJVQS-UHFFFAOYSA-N 0.000 description 1
- YAGOYAVZOJQMRT-UHFFFAOYSA-N 4-(benzenesulfonamido)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NS(=O)(=O)C1=CC=CC=C1 YAGOYAVZOJQMRT-UHFFFAOYSA-N 0.000 description 1
- CHOGMPPUSGFJEB-UHFFFAOYSA-N 4-(benzenesulfonamidomethyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CNS(=O)(=O)C1=CC=CC=C1 CHOGMPPUSGFJEB-UHFFFAOYSA-N 0.000 description 1
- PKXDNBNSQBZKFO-UHFFFAOYSA-N 4-(benzenesulfonyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=CC=C1 PKXDNBNSQBZKFO-UHFFFAOYSA-N 0.000 description 1
- BFIFVZLDXPWFOM-UHFFFAOYSA-N 4-(benzylsulfamoyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1S(=O)(=O)NCC1=CC=CC=C1 BFIFVZLDXPWFOM-UHFFFAOYSA-N 0.000 description 1
- ZOFLWJXPXAHZLI-UHFFFAOYSA-N 4-(benzylsulfonylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NS(=O)(=O)CC1=CC=CC=C1 ZOFLWJXPXAHZLI-UHFFFAOYSA-N 0.000 description 1
- SAYOYSGARAQFRR-UHFFFAOYSA-N 4-(dibenzylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 SAYOYSGARAQFRR-UHFFFAOYSA-N 0.000 description 1
- DMIYEZSENOLXIP-UHFFFAOYSA-N 4-(heptylsulfonylamino)benzoic acid Chemical compound CCCCCCCS(=O)(=O)NC1=CC=C(C(O)=O)C=C1 DMIYEZSENOLXIP-UHFFFAOYSA-N 0.000 description 1
- VNHSSBYXYMABJC-UHFFFAOYSA-N 4-[(2-phenylacetyl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)CC1=CC=CC=C1 VNHSSBYXYMABJC-UHFFFAOYSA-N 0.000 description 1
- CXOGYGMKNVZTHS-UHFFFAOYSA-N 4-[(3-nitrophenyl)sulfonylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 CXOGYGMKNVZTHS-UHFFFAOYSA-N 0.000 description 1
- JQDWCODPTYKORB-UHFFFAOYSA-N 4-[(4-acetamidophenyl)sulfonylamino]benzoic acid Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=C(C(O)=O)C=C1 JQDWCODPTYKORB-UHFFFAOYSA-N 0.000 description 1
- PTCSSXYPZOFISK-UHFFFAOYSA-N 4-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 PTCSSXYPZOFISK-UHFFFAOYSA-N 0.000 description 1
- DBMFYTQPPBBKHI-UHFFFAOYSA-N 4-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)C=C1 DBMFYTQPPBBKHI-UHFFFAOYSA-N 0.000 description 1
- ZESWUEBPRPGMTP-UHFFFAOYSA-N 4-nitrobenzamide Chemical compound NC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZESWUEBPRPGMTP-UHFFFAOYSA-N 0.000 description 1
- AQSCHALQLXXKKC-UHFFFAOYSA-N 4-phenylmethoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCC1=CC=CC=C1 AQSCHALQLXXKKC-UHFFFAOYSA-N 0.000 description 1
- WNLOVPITXSWKEZ-UHFFFAOYSA-N 4-sulfanilamidobenzoic acid Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=C(C(O)=O)C=C1 WNLOVPITXSWKEZ-UHFFFAOYSA-N 0.000 description 1
- 244000235603 Acacia catechu Species 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 235000006226 Areca catechu Nutrition 0.000 description 1
- 206010060945 Bacterial infection Diseases 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N Benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 230000036868 Blood Concentration Effects 0.000 description 1
- 229960004424 Carbon Dioxide Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-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
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 210000000981 Epithelium Anatomy 0.000 description 1
- 240000001441 Fragaria vesca Species 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 229940093912 Gynecological Sulfonamides Drugs 0.000 description 1
- BXPHUDHQIDMXCJ-UHFFFAOYSA-N N-benzyl-4-cyanobenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)NCC1=CC=CC=C1 BXPHUDHQIDMXCJ-UHFFFAOYSA-N 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N Pentylamine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L Sodium thiosulphate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 240000001058 Sterculia urens Species 0.000 description 1
- 235000015125 Sterculia urens Nutrition 0.000 description 1
- CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 230000001154 acute Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000000844 anti-bacterial Effects 0.000 description 1
- 230000003385 bacteriostatic Effects 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- PEWXRXAGXPYMIB-ANPZCEIESA-L calcium;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound [Ca+2].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 PEWXRXAGXPYMIB-ANPZCEIESA-L 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- XHFUVBWCMLLKOZ-UHFFFAOYSA-N ethyl 2-amino-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(N)=N1 XHFUVBWCMLLKOZ-UHFFFAOYSA-N 0.000 description 1
- YKZUCKYQJMJRJN-UHFFFAOYSA-N ethyl 4-[(3-nitrophenyl)methylsulfonylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NS(=O)(=O)CC1=CC=CC([N+]([O-])=O)=C1 YKZUCKYQJMJRJN-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N ethylene glycol monomethyl ether Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- HXIUMEKDVYLMOK-UHFFFAOYSA-N heptane-1-sulfonyl chloride Chemical compound CCCCCCCS(Cl)(=O)=O HXIUMEKDVYLMOK-UHFFFAOYSA-N 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002452 interceptive Effects 0.000 description 1
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- VZDNXXPBYLGWOS-UHFFFAOYSA-N methyl 3-aminobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1 VZDNXXPBYLGWOS-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 description 1
- KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000001340 slower Effects 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229960001663 sulfanilamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 229940026752 topical Sulfonamides Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE475834A true BE475834A (no) |
Family
ID=124402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE475834D BE475834A (no) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE475834A (no) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2608506A (en) * | 1949-08-20 | 1952-08-26 | Sharp & Dohme Inc | Arylsulfamyl benzoic acids |
-
0
- BE BE475834D patent/BE475834A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2608506A (en) * | 1949-08-20 | 1952-08-26 | Sharp & Dohme Inc | Arylsulfamyl benzoic acids |
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