NO130998B - - Google Patents
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- Publication number
- NO130998B NO130998B NO14509962A NO14509962A NO130998B NO 130998 B NO130998 B NO 130998B NO 14509962 A NO14509962 A NO 14509962A NO 14509962 A NO14509962 A NO 14509962A NO 130998 B NO130998 B NO 130998B
- Authority
- NO
- Norway
- Prior art keywords
- chloro
- dihydro
- dioxide
- sulfamyl
- benzothiadiazine
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims 5
- 239000004744 fabric Substances 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 239000000835 fiber Substances 0.000 claims 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- 238000010924 continuous production Methods 0.000 claims 1
- 230000008021 deposition Effects 0.000 claims 1
- 238000005192 partition Methods 0.000 claims 1
- 239000002356 single layer Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000012209 synthetic fiber Substances 0.000 claims 1
- 229920002994 synthetic fiber Polymers 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 113
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 62
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
- -1 aralkyl radical Chemical class 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 31
- 239000000203 mixture Substances 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- 239000000155 melt Substances 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- IHJCXVZDYSXXFT-UHFFFAOYSA-N chloraminophenamide Chemical compound NC1=CC(Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O IHJCXVZDYSXXFT-UHFFFAOYSA-N 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 239000012047 saturated solution Substances 0.000 description 11
- 229930040373 Paraformaldehyde Natural products 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 229920002866 paraformaldehyde Polymers 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical compound NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 description 4
- OKXYPUDKVYVJDI-UHFFFAOYSA-N 3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)NCNC2=C1 OKXYPUDKVYVJDI-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 4
- OLGOYXCALUVMCM-UHFFFAOYSA-N 6-chloro-3-methyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)NC(C)NC2=C1 OLGOYXCALUVMCM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- JVGZNWQUTQMUFN-UHFFFAOYSA-N C(CCCC)C1NS(C2=C(N1)C=CC=C2)(=O)=O Chemical compound C(CCCC)C1NS(C2=C(N1)C=CC=C2)(=O)=O JVGZNWQUTQMUFN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical group S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical class Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- HNFUIXOBWCFVAJ-UHFFFAOYSA-N 2,2-diethoxy-n,n-diethylethanamine Chemical compound CCOC(OCC)CN(CC)CC HNFUIXOBWCFVAJ-UHFFFAOYSA-N 0.000 description 2
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 2
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
- ILEKCYUSYWEDPL-UHFFFAOYSA-N 6-chloro-3-(chloromethyl)-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(CCl)NS2(=O)=O ILEKCYUSYWEDPL-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- PBMSDDUZCQVTJM-UHFFFAOYSA-N C(CCC)C1NS(C2=C(N1)C=C(C(=C2)S(N)(=O)=O)Cl)(=O)=O Chemical compound C(CCC)C1NS(C2=C(N1)C=C(C(=C2)S(N)(=O)=O)Cl)(=O)=O PBMSDDUZCQVTJM-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- HGBFRHCDYZJRAO-UHFFFAOYSA-N butizide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)NC(CC(C)C)NC2=C1 HGBFRHCDYZJRAO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000001452 natriuretic effect Effects 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- 229940100595 phenylacetaldehyde Drugs 0.000 description 2
- 125000000286 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
- 238000002360 preparation method Methods 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- VNSJUZIHZNZLKM-UHFFFAOYSA-N 1,1,2-triethoxyethane Chemical compound CCOCC(OCC)OCC VNSJUZIHZNZLKM-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SSFAUOAQOOISRQ-UHFFFAOYSA-N 2,2-diethoxy-n,n-dimethylethanamine Chemical compound CCOC(CN(C)C)OCC SSFAUOAQOOISRQ-UHFFFAOYSA-N 0.000 description 1
- GHTDAXTYNRRXEC-UHFFFAOYSA-N 2,2-diethoxy-n-methylethanamine Chemical compound CCOC(CNC)OCC GHTDAXTYNRRXEC-UHFFFAOYSA-N 0.000 description 1
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 1
- PDZYOCOHQGFKLC-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)acetaldehyde Chemical compound COC1=CC(CC=O)=CC(OC)=C1OC PDZYOCOHQGFKLC-UHFFFAOYSA-N 0.000 description 1
- YGHDVPXYUQDBER-UHFFFAOYSA-N 2-(3-methylphenyl)acetaldehyde Chemical compound CC1=CC=CC(CC=O)=C1 YGHDVPXYUQDBER-UHFFFAOYSA-N 0.000 description 1
- MWSNYBOKRSGWAN-UHFFFAOYSA-N 2-(4-chlorophenyl)acetaldehyde Chemical compound ClC1=CC=C(CC=O)C=C1 MWSNYBOKRSGWAN-UHFFFAOYSA-N 0.000 description 1
- OVXJWSYBABKZMD-UHFFFAOYSA-N 2-chloro-1,1-diethoxyethane Chemical compound CCOC(CCl)OCC OVXJWSYBABKZMD-UHFFFAOYSA-N 0.000 description 1
- IAHZBRPNDIVNNR-UHFFFAOYSA-N 2-ethoxyacetaldehyde Chemical compound CCOCC=O IAHZBRPNDIVNNR-UHFFFAOYSA-N 0.000 description 1
- IQVAERDLDAZARL-UHFFFAOYSA-N 2-phenylpropanal Chemical compound O=CC(C)C1=CC=CC=C1 IQVAERDLDAZARL-UHFFFAOYSA-N 0.000 description 1
- JTGKLBDOZYMAEA-UHFFFAOYSA-N 2-thiophen-2-ylacetaldehyde Chemical compound O=CCC1=CC=CS1 JTGKLBDOZYMAEA-UHFFFAOYSA-N 0.000 description 1
- CVTBWXDLAWVRNO-UHFFFAOYSA-N 3-(bromomethyl)-6-chloro-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(CBr)NS2(=O)=O CVTBWXDLAWVRNO-UHFFFAOYSA-N 0.000 description 1
- AAHIYAKUVPMLMX-UHFFFAOYSA-N 3-(diethylamino)-2,2-dimethylpropanal Chemical compound CCN(CC)CC(C)(C)C=O AAHIYAKUVPMLMX-UHFFFAOYSA-N 0.000 description 1
- OETUDWYVNUKHJY-UHFFFAOYSA-N 4-amino-6-chloro-1-n,3-n-dimethylbenzene-1,3-disulfonamide Chemical compound CNS(=O)(=O)C1=CC(S(=O)(=O)NC)=C(Cl)C=C1N OETUDWYVNUKHJY-UHFFFAOYSA-N 0.000 description 1
- YIZXGHNDQUYDDF-UHFFFAOYSA-N 4-amino-6-chlorobenzene-1,3-disulfonyl chloride Chemical compound NC1=CC(Cl)=C(S(Cl)(=O)=O)C=C1S(Cl)(=O)=O YIZXGHNDQUYDDF-UHFFFAOYSA-N 0.000 description 1
- OBRVGHAGEZLLGG-UHFFFAOYSA-N 4-amino-6-fluorobenzene-1,3-disulfonamide Chemical compound FC=1C(=CC(=C(N)C1)S(N)(=O)=O)S(N)(=O)=O OBRVGHAGEZLLGG-UHFFFAOYSA-N 0.000 description 1
- IJHBKNKFSJLONU-UHFFFAOYSA-N 4-amino-6-methoxybenzene-1,3-disulfonamide Chemical compound COC1=CC(N)=C(S(N)(=O)=O)C=C1S(N)(=O)=O IJHBKNKFSJLONU-UHFFFAOYSA-N 0.000 description 1
- JGFQDYAUPNZBMU-UHFFFAOYSA-N 4-amino-6-methylbenzene-1,3-disulfonamide Chemical compound CC1=CC(N)=C(S(N)(=O)=O)C=C1S(N)(=O)=O JGFQDYAUPNZBMU-UHFFFAOYSA-N 0.000 description 1
- RQGVTBLIPBGVQH-UHFFFAOYSA-N 4-chloro-6-(methylamino)benzene-1,3-disulfonamide Chemical compound CNC1=CC(Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O RQGVTBLIPBGVQH-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- RUVACBDPACKCQD-UHFFFAOYSA-N 6-bromo-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(Br)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O RUVACBDPACKCQD-UHFFFAOYSA-N 0.000 description 1
- JAQGUQBUUALVON-UHFFFAOYSA-N 6-chloro-1,1-dioxo-3-(2-phenylethyl)-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-7-sulfonamide Chemical compound C1(=CC=CC=C1)CCC1NS(C2=C(N1)C=C(C(=C2)S(N)(=O)=O)Cl)(=O)=O JAQGUQBUUALVON-UHFFFAOYSA-N 0.000 description 1
- CHYSTVUTFXVHBU-UHFFFAOYSA-N 6-chloro-1,1-dioxo-3-(3,4,5-trimethoxyphenyl)-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound COC1=C(OC)C(OC)=CC(C2NS(=O)(=O)C3=CC(=C(Cl)C=C3N2)S(N)(=O)=O)=C1 CHYSTVUTFXVHBU-UHFFFAOYSA-N 0.000 description 1
- YPDKVAXWZXEANV-UHFFFAOYSA-N 6-chloro-1,1-dioxo-3-phenyl-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2C1=CC=CC=C1 YPDKVAXWZXEANV-UHFFFAOYSA-N 0.000 description 1
- AGXFADDNQIWXSX-UHFFFAOYSA-N 6-chloro-1,1-dioxo-3-propyl-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-7-sulfonamide Chemical compound C(CC)C1NS(C2=C(N1)C=C(C(=C2)S(N)(=O)=O)Cl)(=O)=O AGXFADDNQIWXSX-UHFFFAOYSA-N 0.000 description 1
- KOBWIKFYTHTBBQ-UHFFFAOYSA-N 6-chloro-2-ethyl-1,1-dioxo-3,4-dihydro-1lambda6,2,4-benzothiadiazine-7-sulfonamide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(CC)CNC2=C1 KOBWIKFYTHTBBQ-UHFFFAOYSA-N 0.000 description 1
- CNSCONHVBQJXDB-UHFFFAOYSA-N 6-chloro-2-methyl-1,1-dioxo-3,4-dihydro-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)CNC2=C1 CNSCONHVBQJXDB-UHFFFAOYSA-N 0.000 description 1
- SPEJBSPBBQWGMM-UHFFFAOYSA-N 6-chloro-3-(2-methylphenyl)-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound CC1=CC=CC=C1C1NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C2N1 SPEJBSPBBQWGMM-UHFFFAOYSA-N 0.000 description 1
- HSEYPMAIZGZYAC-UHFFFAOYSA-N 6-chloro-4-methyl-1,1-dioxo-2,3-dihydro-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound NS(=O)(=O)C1=C(Cl)C=C2N(C)CNS(=O)(=O)C2=C1 HSEYPMAIZGZYAC-UHFFFAOYSA-N 0.000 description 1
- DFQSFXTVRYWSNI-UHFFFAOYSA-N 6-chloro-N,2,3-trimethyl-1,1-dioxo-3,4-dihydro-1lambda6,2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)NC)=CC2=C1NC(C)N(C)S2(=O)=O DFQSFXTVRYWSNI-UHFFFAOYSA-N 0.000 description 1
- QBFRPGRSZWPABV-UHFFFAOYSA-N 6-fluoro-1,1-dioxo-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(F)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O QBFRPGRSZWPABV-UHFFFAOYSA-N 0.000 description 1
- BGZDIKVIOYLLOV-UHFFFAOYSA-N 6-methoxy-1,1-dioxo-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-7-sulfonamide Chemical compound COc1cc2NCNS(=O)(=O)c2cc1S(N)(=O)=O BGZDIKVIOYLLOV-UHFFFAOYSA-N 0.000 description 1
- PFHLGOOYVFGCPT-UHFFFAOYSA-N 6-methyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound N1CNS(=O)(=O)C2=C1C=C(C)C(S(N)(=O)=O)=C2 PFHLGOOYVFGCPT-UHFFFAOYSA-N 0.000 description 1
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
- BWSSMIJUDVUASQ-UHFFFAOYSA-N Benzylhydrochlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 BWSSMIJUDVUASQ-UHFFFAOYSA-N 0.000 description 1
- XWIMGTAOCKNOJW-UHFFFAOYSA-N C(C)NS(=O)(=O)C1=C(N)C=C(C(=C1)S(NCC)(=O)=O)Cl Chemical compound C(C)NS(=O)(=O)C1=C(N)C=C(C(=C1)S(NCC)(=O)=O)Cl XWIMGTAOCKNOJW-UHFFFAOYSA-N 0.000 description 1
- GSSFRHCSNMSXEJ-UHFFFAOYSA-N CN(C)Cl[N+](=O)[O-] Chemical compound CN(C)Cl[N+](=O)[O-] GSSFRHCSNMSXEJ-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- BZPSXPLHELNUQK-UHFFFAOYSA-N NS(C(C(Cl)=C1)=CC2=C1NC(CC(C=C1)=CC=C1Cl)NS2(=O)=O)(=O)=O Chemical compound NS(C(C(Cl)=C1)=CC2=C1NC(CC(C=C1)=CC=C1Cl)NS2(=O)=O)(=O)=O BZPSXPLHELNUQK-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- PYVUMAGVCSQCBD-UHFFFAOYSA-N bemetizide Chemical compound N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C(C)C1=CC=CC=C1 PYVUMAGVCSQCBD-UHFFFAOYSA-N 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
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- GZDYCKLIQUPOIR-UHFFFAOYSA-N n-(2,2-diethoxyethyl)acetamide Chemical compound CCOC(OCC)CNC(C)=O GZDYCKLIQUPOIR-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21F—PAPER-MAKING MACHINES; METHODS OF PRODUCING PAPER THEREON
- D21F11/00—Processes for making continuous lengths of paper, or of cardboard, or of wet web for fibre board production, on paper-making machines
- D21F11/02—Processes for making continuous lengths of paper, or of cardboard, or of wet web for fibre board production, on paper-making machines of the Fourdrinier type
- D21F11/04—Processes for making continuous lengths of paper, or of cardboard, or of wet web for fibre board production, on paper-making machines of the Fourdrinier type paper or board consisting on two or more layers
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21F—PAPER-MAKING MACHINES; METHODS OF PRODUCING PAPER THEREON
- D21F9/00—Complete machines for making continuous webs of paper
- D21F9/02—Complete machines for making continuous webs of paper of the Fourdrinier type
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Nonwoven Fabrics (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0034434 | 1961-07-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO130998B true NO130998B (xx) | 1974-12-09 |
| NO130998C NO130998C (xx) | 1975-03-25 |
Family
ID=7095547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO14509962A NO130998C (xx) | 1961-07-14 | 1962-07-13 |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH402587A (xx) |
| DE (1) | DE1411296A1 (xx) |
| FI (1) | FI48211C (xx) |
| GB (1) | GB1017372A (xx) |
| NO (1) | NO130998C (xx) |
| SE (1) | SE328763B (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103726383A (zh) * | 2013-04-22 | 2014-04-16 | 太仓派欧技术咨询服务有限公司 | 一种玻璃纤维浆料流动导向的层状导流架 |
-
1961
- 1961-07-14 DE DE19611411296 patent/DE1411296A1/de active Pending
-
1962
- 1962-07-13 FI FI134262A patent/FI48211C/fi active
- 1962-07-13 SE SE790262A patent/SE328763B/xx unknown
- 1962-07-13 CH CH844162A patent/CH402587A/de unknown
- 1962-07-13 NO NO14509962A patent/NO130998C/no unknown
- 1962-07-16 GB GB2731862A patent/GB1017372A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH402587A (de) | 1965-11-15 |
| FI48211C (fi) | 1974-07-10 |
| FI48211B (xx) | 1974-04-01 |
| SE328763B (xx) | 1970-09-21 |
| GB1017372A (en) | 1966-01-19 |
| DE1411296A1 (de) | 1969-07-31 |
| NO130998C (xx) | 1975-03-25 |
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