NO128369B - - Google Patents
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- Publication number
- NO128369B NO128369B NO393168A NO393168A NO128369B NO 128369 B NO128369 B NO 128369B NO 393168 A NO393168 A NO 393168A NO 393168 A NO393168 A NO 393168A NO 128369 B NO128369 B NO 128369B
- Authority
- NO
- Norway
- Prior art keywords
- benzothiadiazine
- disulfamylaniline
- chloro
- general formula
- sulfamyl
- Prior art date
Links
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- QLGJNQICDRXXGG-UHFFFAOYSA-N (disulfamoylamino)benzene Chemical compound NS(=O)(=O)N(S(N)(=O)=O)C1=CC=CC=C1 QLGJNQICDRXXGG-UHFFFAOYSA-N 0.000 claims description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 7
- IHJCXVZDYSXXFT-UHFFFAOYSA-N chloraminophenamide Chemical compound NC1=CC(Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O IHJCXVZDYSXXFT-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 239000002934 diuretic Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 230000001882 diuretic effect Effects 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 230000001452 natriuretic effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 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 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 230000010933 acylation Effects 0.000 description 8
- 238000005917 acylation reaction Methods 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 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 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000003918 potentiometric titration Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- UOCUSOBVEHOMMB-UHFFFAOYSA-N 2h-1$l^{6},2,3-benzothiadiazine 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)NN=CC2=C1 UOCUSOBVEHOMMB-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000007658 benzothiadiazines Chemical class 0.000 description 2
- -1 disulfamyl-aniline compound Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- CGVXNZNOSZFBCD-UHFFFAOYSA-N 1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound N1=CNS(=O)(=O)C2=CC(S(=O)(=O)N)=CC=C21 CGVXNZNOSZFBCD-UHFFFAOYSA-N 0.000 description 1
- MJERGERFTHOTKE-UHFFFAOYSA-N 2-amino-5-chlorobenzene-1,4-disulfonamide Chemical compound ClC1=CC(=C(N)C=C1S(N)(=O)=O)S(N)(=O)=O MJERGERFTHOTKE-UHFFFAOYSA-N 0.000 description 1
- YRXAPDMJILMLSU-UHFFFAOYSA-N 4-amino-6-bromobenzene-1,3-disulfonamide Chemical compound NC1=CC(Br)=C(S(N)(=O)=O)C=C1S(N)(=O)=O YRXAPDMJILMLSU-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
- IBNXNSNZXLVXSJ-UHFFFAOYSA-N 4-amino-6-nitrobenzene-1,3-disulfonamide Chemical compound NC1=CC([N+]([O-])=O)=C(S(N)(=O)=O)C=C1S(N)(=O)=O IBNXNSNZXLVXSJ-UHFFFAOYSA-N 0.000 description 1
- BOZSDDFQWJUBNG-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1S(N)(=O)=O BOZSDDFQWJUBNG-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
- CAAKQRQFOMKFGK-UHFFFAOYSA-N 6-bromo-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(Br)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O CAAKQRQFOMKFGK-UHFFFAOYSA-N 0.000 description 1
- YYWLICGCICEVGT-UHFFFAOYSA-N 6-fluoro-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(F)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O YYWLICGCICEVGT-UHFFFAOYSA-N 0.000 description 1
- OGXNOHZPFAKPAC-UHFFFAOYSA-N 6-methoxy-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound N1C=NS(=O)(=O)C2=C1C=C(OC)C(S(N)(=O)=O)=C2 OGXNOHZPFAKPAC-UHFFFAOYSA-N 0.000 description 1
- IWBSWYWGBOZUQZ-UHFFFAOYSA-N 6-methyl-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound N1=CNS(=O)(=O)C2=C1C=C(C)C(S(N)(=O)=O)=C2 IWBSWYWGBOZUQZ-UHFFFAOYSA-N 0.000 description 1
- SFQURDGCJHTBMC-UHFFFAOYSA-N 6-nitro-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C([N+]([O-])=O)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O SFQURDGCJHTBMC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- AJTSGHFOJGUPKV-UHFFFAOYSA-N ClC1=CC2=C(N=CNS2(=O)=O)C=C1S(N)(=O)=O Chemical compound ClC1=CC2=C(N=CNS2(=O)=O)C=C1S(N)(=O)=O AJTSGHFOJGUPKV-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6454067 | 1967-10-06 | ||
| JP8173167 | 1967-12-20 | ||
| JP528068 | 1968-01-29 | ||
| JP1277368 | 1968-02-28 | ||
| JP1396668 | 1968-03-04 | ||
| JP1812268 | 1968-03-19 | ||
| JP2391768 | 1968-04-10 | ||
| JP4403368 | 1968-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128369B true NO128369B (pt) | 1973-11-05 |
Family
ID=27571550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO393168A NO128369B (pt) | 1967-10-06 | 1968-10-04 |
Country Status (2)
| Country | Link |
|---|---|
| FI (1) | FI49979C (pt) |
| NO (1) | NO128369B (pt) |
-
1968
- 1968-10-04 NO NO393168A patent/NO128369B/no unknown
- 1968-10-04 FI FI280468A patent/FI49979C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| FI49979B (pt) | 1975-07-31 |
| FI49979C (fi) | 1975-11-10 |
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