PL81343B1 - - Google Patents
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- PL81343B1 PL81343B1 PL1967123925A PL12392567A PL81343B1 PL 81343 B1 PL81343 B1 PL 81343B1 PL 1967123925 A PL1967123925 A PL 1967123925A PL 12392567 A PL12392567 A PL 12392567A PL 81343 B1 PL81343 B1 PL 81343B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- formula
- chloro
- dichloro
- give
- Prior art date
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 126
- -1 4-fluorophenylsulfamoyl Chemical group 0.000 claims description 104
- 239000002253 acid Substances 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 52
- 125000001931 aliphatic group Chemical group 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 239000007858 starting material Substances 0.000 claims description 28
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 21
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 16
- KTWCBPNVALETHA-UHFFFAOYSA-N 2,4-dichloro-5-(phenylsulfamoyl)benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(S(=O)(=O)NC=2C=CC=CC=2)=C1Cl KTWCBPNVALETHA-UHFFFAOYSA-N 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- ADGDDISMOKXBCG-UHFFFAOYSA-N 4-chloro-2-(furan-2-ylmethylamino)-5-(phenylsulfamoyl)benzoic acid Chemical compound OC(=O)C1=CC(S(=O)(=O)NC=2C=CC=CC=2)=C(Cl)C=C1NCC1=CC=CO1 ADGDDISMOKXBCG-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 6
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- HOFZUHZPCFZJAA-UHFFFAOYSA-N 2,4-dichloro-5-[(4-methylphenyl)sulfamoyl]benzoic acid Chemical compound ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(NC1=CC=C(C=C1)C)(=O)=O HOFZUHZPCFZJAA-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 claims description 3
- HCAUYQLDJTWXAV-UHFFFAOYSA-N 2,4-dichloro-5-[(2-chlorophenyl)sulfamoyl]benzoic acid Chemical compound OC(=O)C1=C(Cl)C=C(Cl)C(=C1)S(=O)(=O)NC1=C(Cl)C=CC=C1 HCAUYQLDJTWXAV-UHFFFAOYSA-N 0.000 claims description 2
- OTSLSIROCRGQKW-UHFFFAOYSA-N 2,4-dichloro-5-[(3-chlorophenyl)sulfamoyl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(S(=O)(=O)NC=2C=C(Cl)C=CC=2)=C1Cl OTSLSIROCRGQKW-UHFFFAOYSA-N 0.000 claims description 2
- NRPBJEMEHKHKFB-UHFFFAOYSA-N 2,4-dichloro-5-[(4-methoxyphenyl)sulfamoyl]benzoic acid Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC(C(O)=O)=C(Cl)C=C1Cl NRPBJEMEHKHKFB-UHFFFAOYSA-N 0.000 claims description 2
- UUDUWVNKUYFIRG-UHFFFAOYSA-N 2,4-dichloro-5-[(4-nitrophenyl)sulfamoyl]benzoic acid Chemical compound ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(NC1=CC=C(C=C1)[N+](=O)[O-])(=O)=O UUDUWVNKUYFIRG-UHFFFAOYSA-N 0.000 claims description 2
- VNMHHVDXXHZGDU-UHFFFAOYSA-N 3,4-dihydro-2h-pyran-2-ylmethanamine Chemical compound NCC1CCC=CO1 VNMHHVDXXHZGDU-UHFFFAOYSA-N 0.000 claims description 2
- YHEFQZRLXFULTL-UHFFFAOYSA-N 5-[(4-acetamidophenyl)sulfamoyl]-2,4-dichlorobenzoic acid Chemical compound ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(NC1=CC=C(C=C1)NC(C)=O)(=O)=O YHEFQZRLXFULTL-UHFFFAOYSA-N 0.000 claims description 2
- NFNJUJDXCXINGF-UHFFFAOYSA-N Cl.ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(NC1=CC=C(C=C1)N)(=O)=O Chemical compound Cl.ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(NC1=CC=C(C=C1)N)(=O)=O NFNJUJDXCXINGF-UHFFFAOYSA-N 0.000 claims description 2
- PPGUIZHEMNCHTN-UHFFFAOYSA-N ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(NC1=CC=C(C=C1)C(F)(F)F)(=O)=O Chemical compound ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(NC1=CC=C(C=C1)C(F)(F)F)(=O)=O PPGUIZHEMNCHTN-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 14
- DLTMPHWJUYBJGY-UHFFFAOYSA-N 2,4-dichloro-5-[(4-fluorophenyl)sulfamoyl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(S(=O)(=O)NC=2C=CC(F)=CC=2)=C1Cl DLTMPHWJUYBJGY-UHFFFAOYSA-N 0.000 claims 1
- HCYZZYSWBCKMOZ-UHFFFAOYSA-N 2,4-dichloro-5-[[3-(trifluoromethyl)phenyl]sulfamoyl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(S(=O)(=O)NC=2C=C(C=CC=2)C(F)(F)F)=C1Cl HCYZZYSWBCKMOZ-UHFFFAOYSA-N 0.000 claims 1
- OAZOBYBYAKXURF-UHFFFAOYSA-N 2-(sulfamoylamino)benzoic acid Chemical compound NS(=O)(=O)NC1=CC=CC=C1C(O)=O OAZOBYBYAKXURF-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 85
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000002244 precipitate Substances 0.000 description 38
- 239000000203 mixture Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000155 melt Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000001953 recrystallisation Methods 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 210000002700 urine Anatomy 0.000 description 7
- MPUNAIYDVXJQBJ-UHFFFAOYSA-N 2,4-dichloro-5-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC(S(Cl)(=O)=O)=C(Cl)C=C1Cl MPUNAIYDVXJQBJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000002619 bicyclic group Chemical group 0.000 description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000002934 diuretic Substances 0.000 description 4
- 230000001882 diuretic effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- VASMTGOLJFHPPK-UHFFFAOYSA-N 2-(benzylamino)-4-chloro-5-(phenylsulfamoyl)benzoic acid Chemical compound C(C1=CC=CC=C1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NC1=CC=CC=C1)(=O)=O VASMTGOLJFHPPK-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- 208000004880 Polyuria Diseases 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-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
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- SULIWCUUYDLMPO-UHFFFAOYSA-N 2-(benzylamino)-4-chloro-5-[methyl(phenyl)sulfamoyl]benzoic acid Chemical compound CN(C1=CC=CC=C1)S(=O)(=O)C1=C(Cl)C=C(NCC2=CC=CC=C2)C(=C1)C(O)=O SULIWCUUYDLMPO-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- GSGIUUPEUHONLV-UHFFFAOYSA-N 4-chloro-2-(furan-2-ylmethylamino)-5-[(4-methylphenyl)sulfamoyl]benzoic acid Chemical compound C(C1=CC=CO1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NC1=CC=C(C=C1)C)(=O)=O GSGIUUPEUHONLV-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000035619 diuresis Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- DLFCAVBMDSKMEY-UHFFFAOYSA-M sodium;4-chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoate Chemical compound [Na+].C1=C(Cl)C(S(=O)(=O)N)=CC(C([O-])=O)=C1NCC1=CC=CO1 DLFCAVBMDSKMEY-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- KNXVOGGZOFOROK-UHFFFAOYSA-N trimagnesium;dioxido(oxo)silane;hydroxy-oxido-oxosilane Chemical compound [Mg+2].[Mg+2].[Mg+2].O[Si]([O-])=O.O[Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O KNXVOGGZOFOROK-UHFFFAOYSA-N 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/42—Halides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59898066A | 1966-12-05 | 1966-12-05 | |
| US67533067A | 1967-10-16 | 1967-10-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL81343B1 true PL81343B1 (fi) | 1975-08-30 |
Family
ID=27083205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1967123925A PL81343B1 (fi) | 1966-12-05 | 1967-12-05 |
Country Status (8)
| Country | Link |
|---|---|
| BG (3) | BG16740A3 (fi) |
| ES (1) | ES347918A1 (fi) |
| FI (1) | FI48073C (fi) |
| GR (1) | GR37781B (fi) |
| NO (1) | NO121839B (fi) |
| OA (1) | OA02544A (fi) |
| PL (1) | PL81343B1 (fi) |
| SE (1) | SE358385B (fi) |
-
1967
- 1967-11-22 NO NO170638A patent/NO121839B/no unknown
- 1967-12-02 ES ES347918A patent/ES347918A1/es not_active Expired
- 1967-12-02 FI FI673240A patent/FI48073C/fi active
- 1967-12-04 GR GR670137781A patent/GR37781B/el unknown
- 1967-12-04 SE SE16614/67A patent/SE358385B/xx unknown
- 1967-12-05 OA OA53114A patent/OA02544A/xx unknown
- 1967-12-05 PL PL1967123925A patent/PL81343B1/pl unknown
- 1967-12-06 BG BG013557A patent/BG16740A3/xx unknown
- 1967-12-06 BG BG008997A patent/BG15875A3/bg unknown
- 1967-12-06 BG BG013556A patent/BG15563A3/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE358385B (fi) | 1973-07-30 |
| FI48073C (fi) | 1974-06-10 |
| BG15875A3 (bg) | 1972-04-12 |
| BG16740A3 (bg) | 1973-02-15 |
| FI48073B (fi) | 1974-02-28 |
| OA02544A (fr) | 1970-05-05 |
| NO121839B (fi) | 1971-04-19 |
| GR37781B (el) | 1969-07-14 |
| BG15563A3 (bg) | 1976-04-29 |
| ES347918A1 (es) | 1969-06-01 |
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