BE569297A - - Google Patents
Info
- Publication number
- BE569297A BE569297A BE569297DA BE569297A BE 569297 A BE569297 A BE 569297A BE 569297D A BE569297D A BE 569297DA BE 569297 A BE569297 A BE 569297A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- sulfonyl
- alkyl
- benzene
- hydroxy
- Prior art date
Links
- -1 alkali metal salts Chemical class 0.000 claims description 27
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 18
- 230000000875 corresponding Effects 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229940090121 Sulfonylureas for blood glucose lowering Drugs 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl N-sulfonylcarbamate Chemical class CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 claims description 11
- 239000011780 sodium chloride Substances 0.000 claims description 9
- 229940093912 Gynecological Sulfonamides Drugs 0.000 claims description 8
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 claims description 8
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229940026752 topical Sulfonamides Drugs 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 5
- 238000005809 transesterification reaction Methods 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 238000010504 bond cleavage reaction Methods 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 1
- 230000003000 nontoxic Effects 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 227
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- 235000019441 ethanol Nutrition 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- XNWFRZJHXBZDAG-UHFFFAOYSA-N ethylene glycol monomethyl ether Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 201000009910 diseases by infectious agent Diseases 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 150000003456 sulfonamides Chemical class 0.000 description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- OFVLGDICTFRJMM-WESIUVDSSA-N Tetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O OFVLGDICTFRJMM-WESIUVDSSA-N 0.000 description 5
- 229960002180 Tetracycline Drugs 0.000 description 5
- 239000004098 Tetracycline Substances 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 235000019364 tetracycline Nutrition 0.000 description 5
- 241000223932 Eimeria tenella Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CXLBYPJSAWOYSI-UHFFFAOYSA-N ethyl N-methyl-N-(4-methylphenyl)sulfonylcarbamate Chemical compound CCOC(=O)N(C)S(=O)(=O)C1=CC=C(C)C=C1 CXLBYPJSAWOYSI-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-N-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 3
- 208000003495 Coccidiosis Diseases 0.000 description 3
- 206010023076 Isosporiasis Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- 235000020188 drinking water Nutrition 0.000 description 3
- 239000003651 drinking water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000035876 healing Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- XOBKSJJDNFUZPF-UHFFFAOYSA-N methoxyethyl Chemical group CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000001225 therapeutic Effects 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- 210000004369 Blood Anatomy 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N Chloroformic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 230000003178 anti-diabetic Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 description 1
- YCIHPQHVWDULOY-FMZCEJRJSA-N (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O YCIHPQHVWDULOY-FMZCEJRJSA-N 0.000 description 1
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 1
- GPOYJVWXGJBMOK-UHFFFAOYSA-N 1-phenoxy-4-phenylbenzene Chemical group C=1C=C(C=2C=CC=CC=2)C=CC=1OC1=CC=CC=C1 GPOYJVWXGJBMOK-UHFFFAOYSA-N 0.000 description 1
- IWEYZXWPWNBRLG-UHFFFAOYSA-N 2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(N)(=O)=O IWEYZXWPWNBRLG-UHFFFAOYSA-N 0.000 description 1
- YUYXBLYSKPNXPT-UHFFFAOYSA-N 3-methylbutane-1-sulfonamide Chemical compound CC(C)CCS(N)(=O)=O YUYXBLYSKPNXPT-UHFFFAOYSA-N 0.000 description 1
- MLTGAVXHWSDGIS-UHFFFAOYSA-N 4-ethylbenzenesulfonamide Chemical class CCC1=CC=C(S(N)(=O)=O)C=C1 MLTGAVXHWSDGIS-UHFFFAOYSA-N 0.000 description 1
- MSFQEZBRFPAFEX-UHFFFAOYSA-N 4-methoxybenzenesulfonamide Chemical class COC1=CC=C(S(N)(=O)=O)C=C1 MSFQEZBRFPAFEX-UHFFFAOYSA-N 0.000 description 1
- XOZPKUQZIDQKCC-UHFFFAOYSA-N 6-methyl-7-thiabicyclo[4.1.0]hepta-2,4-diene Chemical compound C1=CC=CC2(C)C1S2 XOZPKUQZIDQKCC-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- LHQIAMRGAWPQOG-UHFFFAOYSA-N C(C(C)C)S(=O)(=O)NC(=O)N Chemical compound C(C(C)C)S(=O)(=O)NC(=O)N LHQIAMRGAWPQOG-UHFFFAOYSA-N 0.000 description 1
- MATSUQAPTKRAIZ-UHFFFAOYSA-N C(CCC)S(=O)(=O)NC(=O)NC(C)=O Chemical compound C(CCC)S(=O)(=O)NC(=O)NC(C)=O MATSUQAPTKRAIZ-UHFFFAOYSA-N 0.000 description 1
- BGSLZUFNYUSZHB-UHFFFAOYSA-N C(CCCCCC)S(=O)(=O)NC(=O)N Chemical compound C(CCCCCC)S(=O)(=O)NC(=O)N BGSLZUFNYUSZHB-UHFFFAOYSA-N 0.000 description 1
- SGXHNBVJMTXCPY-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C(C)C)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C(C)C)C SGXHNBVJMTXCPY-UHFFFAOYSA-N 0.000 description 1
- NCIWGJSMUVSPPP-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCCCCCCCCCC)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCCCCCCCCCC)C NCIWGJSMUVSPPP-UHFFFAOYSA-N 0.000 description 1
- CORVQXYAQRYBPW-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)N(C(=O)NC(C)=O)C(CCCC(CC)=O)=O Chemical compound C1(=CC=CC=C1)S(=O)(=O)N(C(=O)NC(C)=O)C(CCCC(CC)=O)=O CORVQXYAQRYBPW-UHFFFAOYSA-N 0.000 description 1
- QKMZRTPNTOPHPH-UHFFFAOYSA-N C1(CCCCC1)S(=O)(=O)NC(=O)NC(C)=O Chemical compound C1(CCCCC1)S(=O)(=O)NC(=O)NC(C)=O QKMZRTPNTOPHPH-UHFFFAOYSA-N 0.000 description 1
- 101700055557 CNBD2 Proteins 0.000 description 1
- 241000224483 Coccidia Species 0.000 description 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N Cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
- 102000016736 Cyclins Human genes 0.000 description 1
- 108050006400 Cyclins Proteins 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N Dodecanol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 210000003238 Esophagus Anatomy 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 210000000936 Intestines Anatomy 0.000 description 1
- 230000036740 Metabolism Effects 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N Methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- NWIFRSJMWOEKNP-UHFFFAOYSA-N N-[(4-methylphenyl)sulfonylcarbamoyl]acetamide Chemical compound CC(=O)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 NWIFRSJMWOEKNP-UHFFFAOYSA-N 0.000 description 1
- MOIQCUSEEYCGON-UHFFFAOYSA-N S(=O)(=O)=C(OC(NC)=O)C Chemical class S(=O)(=O)=C(OC(NC)=O)C MOIQCUSEEYCGON-UHFFFAOYSA-N 0.000 description 1
- JHKKZPVCSDCSSF-UHFFFAOYSA-N S(=O)(=O)=NC(=O)N.CCC Chemical compound S(=O)(=O)=NC(=O)N.CCC JHKKZPVCSDCSSF-UHFFFAOYSA-N 0.000 description 1
- BZKICOFSQOWHPW-UHFFFAOYSA-N ST023535 Chemical compound C=1C(=C2OCCBr)CC(C=3OCCBr)=CC(C4(C)CCCCC4)=CC=3CC(C=3OCCBr)=CC(C4(C)CCCCC4)=CC=3CC(C=3OCCBr)=CC(C4(C)CCCCC4)=CC=3CC2=CC=1C1(C)CCCCC1 BZKICOFSQOWHPW-UHFFFAOYSA-N 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N Sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-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
- RUDATBOHQWOJDD-UZVSRGJWSA-N Ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004848 alkoxyethyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 230000001580 bacterial Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 150000008331 benzenesulfonamides Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000003197 catalytic Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- YEJJFGYKPOEVPJ-UHFFFAOYSA-N cycloheptanesulfonamide Chemical compound NS(=O)(=O)C1CCCCCC1 YEJJFGYKPOEVPJ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- AAYHAFZXFMIUSN-UHFFFAOYSA-N cyclohexanesulfonamide Chemical compound NS(=O)(=O)C1CCCCC1 AAYHAFZXFMIUSN-UHFFFAOYSA-N 0.000 description 1
- VJPGNAIPMMGCSU-UHFFFAOYSA-N cyclohexylmethanesulfonamide Chemical compound NS(=O)(=O)CC1CCCCC1 VJPGNAIPMMGCSU-UHFFFAOYSA-N 0.000 description 1
- OPASRWWZEIMSOZ-UHFFFAOYSA-N cyclopentanesulfonamide Chemical compound NS(=O)(=O)C1CCCC1 OPASRWWZEIMSOZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- YPPVLWVYJSVLHI-UHFFFAOYSA-N ethyl N-(2-methoxyethyl)carbamate Chemical compound CCOC(=O)NCCOC YPPVLWVYJSVLHI-UHFFFAOYSA-N 0.000 description 1
- DFWQXANLGSXMKF-UHFFFAOYSA-N ethyl N-(4-methylphenyl)sulfonylcarbamate Chemical class CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 DFWQXANLGSXMKF-UHFFFAOYSA-N 0.000 description 1
- PKGNFJLDVFEWKR-UHFFFAOYSA-N ethyl N-ethyl-N-(4-methylphenyl)sulfonylcarbamate Chemical compound CCOC(=O)N(CC)S(=O)(=O)C1=CC=C(C)C=C1 PKGNFJLDVFEWKR-UHFFFAOYSA-N 0.000 description 1
- GZXSDYYWLZERLF-UHFFFAOYSA-N ethyl N-ethylcarbamate Chemical class CCNC(=O)OCC GZXSDYYWLZERLF-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting Effects 0.000 description 1
- 150000004665 fatty acids Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- XXRLNWSPPBSGMY-UHFFFAOYSA-N heptane-1-sulfonamide Chemical compound CCCCCCCS(N)(=O)=O XXRLNWSPPBSGMY-UHFFFAOYSA-N 0.000 description 1
- RMSHYQAVCSUECE-UHFFFAOYSA-N hexane-1-sulfonamide Chemical compound CCCCCCS(N)(=O)=O RMSHYQAVCSUECE-UHFFFAOYSA-N 0.000 description 1
- GDTYBLJDMHNTAX-UHFFFAOYSA-N hexylsulfonylurea Chemical compound CCCCCCS(=O)(=O)NC(N)=O GDTYBLJDMHNTAX-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000035786 metabolism Effects 0.000 description 1
- RARUETBKDGBHCE-UHFFFAOYSA-N naphthalen-2-ylsulfonylurea Chemical compound C1=CC=CC2=CC(S(=O)(=O)NC(=O)N)=CC=C21 RARUETBKDGBHCE-UHFFFAOYSA-N 0.000 description 1
- QWOKKHXWFDAJCZ-UHFFFAOYSA-N octane-1-sulfonamide Chemical compound CCCCCCCCS(N)(=O)=O QWOKKHXWFDAJCZ-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AZEPYUPSYWCRBG-UHFFFAOYSA-N p-Chlorobenzene sulfonyl urea Chemical compound NC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 AZEPYUPSYWCRBG-UHFFFAOYSA-N 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 description 1
- SJMCLWCCNYAWRQ-UHFFFAOYSA-N propane-2-sulfonamide Chemical compound CC(C)S(N)(=O)=O SJMCLWCCNYAWRQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- PHADAZBGNPFOGF-UHFFFAOYSA-M sodium;azanylidynemethanesulfinate Chemical compound [Na+].[O-]S(=O)C#N PHADAZBGNPFOGF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229960001663 sulfanilamide Drugs 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/53—X and Y not being nitrogen atoms, e.g. N-sulfonylcarbamic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE569297A true BE569297A (hr) |
Family
ID=188316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE569297D BE569297A (hr) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE569297A (hr) |
-
0
- BE BE569297D patent/BE569297A/fr unknown
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