CH382745A - Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden - Google Patents

Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden

Info

Publication number: CH382745A
Authority: CH; Switzerland
Prior art keywords: formula; dihydro; formaldehyde; benzothiadiazine; sulfamyl
Prior art date: 1958-07-31

Application number

CH7602559A

Other languages

German (de)

English (en)

Inventor

Bennet Magerison Richard

Charles Shabica Anthony

Benjamin Ziegler John

Original Assignee

Ciba Geigy

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1958-07-31

Filing date

1959-07-21

Publication date

1964-10-15

1959-05-12 Priority claimed from US812579A external-priority patent/US3095446A/en

1959-07-21 Application filed by Ciba Geigy filed Critical Ciba Geigy

1964-10-15 Publication of CH382745A publication Critical patent/CH382745A/de

Links

238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
229930040373 Paraformaldehyde Natural products 0.000 claims description 4
229920002866 paraformaldehyde Polymers 0.000 claims description 4
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
229940061627 chloromethyl methyl ether Drugs 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
229910000039 hydrogen halide Inorganic materials 0.000 claims 1
239000012433 hydrogen halide Substances 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
-1 alkyl radicals Chemical class 0.000 description 11
239000000243 solution Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
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 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000002934 diuretic Substances 0.000 description 2
230000001882 diuretic effect Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-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
SZLZWPPUNLXJEA-UHFFFAOYSA-N 11,17-dimethoxy-18-[3-(3,4,5-trimethoxy-phenyl)-acryloyloxy]-yohimbane-16-carboxylic acid methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(OC)C1OC(=O)C=CC1=CC(OC)=C(OC)C(OC)=C1 SZLZWPPUNLXJEA-UHFFFAOYSA-N 0.000 description 1
IDYGWCRGOWDFAM-UHFFFAOYSA-N 4-amino-6-(trifluoromethyl)benzene-1,3-disulfonyl chloride Chemical compound FC(C1=C(C=C(C(N)=C1)S(=O)(=O)Cl)S(=O)(=O)Cl)(F)F IDYGWCRGOWDFAM-UHFFFAOYSA-N 0.000 description 1
NFYAJBONLJKHDP-UHFFFAOYSA-N 4-amino-6-methylbenzene-1,3-disulfonyl chloride Chemical compound CC1=CC(N)=C(S(Cl)(=O)=O)C=C1S(Cl)(=O)=O NFYAJBONLJKHDP-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
CVBMAZKKCSYWQR-BPJCFPRXSA-N Deserpidine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cccc3 CVBMAZKKCSYWQR-BPJCFPRXSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
208000003098 Ganglion Cysts Diseases 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
RNPABQVCNAUEIY-GUQYYFCISA-N Germine Chemical compound O1[C@@]([C@H](CC[C@]23C)O)(O)[C@H]3C[C@@H](O)[C@@H]([C@]3(O)[C@@H](O)[C@H](O)[C@@H]4[C@]5(C)O)[C@@]12C[C@H]3[C@@H]4CN1[C@H]5CC[C@H](C)C1 RNPABQVCNAUEIY-GUQYYFCISA-N 0.000 description 1
229930189630 Protoveratrine Natural products 0.000 description 1
HYTGGNIMZXFORS-MGYKWWNKSA-N Protoveratrine A Chemical compound O1[C@@]([C@H](CC[C@]23C)OC(=O)[C@@](C)(O)CC)(O)[C@H]3[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]3[C@@]12C[C@H]1[C@H](CN2[C@@H](CC[C@H](C)C2)[C@@]2(C)O)[C@@H]2[C@@H](O)[C@H](OC(=O)[C@H](C)CC)[C@@]31O HYTGGNIMZXFORS-MGYKWWNKSA-N 0.000 description 1
241000208332 Rauvolfia Species 0.000 description 1
SZLZWPPUNLXJEA-FMCDHCOASA-N Rescinnamine Natural products O=C(O[C@H]1[C@@H](OC)[C@@H](C(=O)OC)[C@@H]2[C@H](C1)CN1[C@@H](c3[nH]c4c(c3CC1)ccc(OC)c4)C2)/C=C/c1cc(OC)c(OC)c(OC)c1 SZLZWPPUNLXJEA-FMCDHCOASA-N 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000005400 Synovial Cyst Diseases 0.000 description 1
241000112708 Vates Species 0.000 description 1
241000489523 Veratrum Species 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 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
239000000872 buffer Substances 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
239000002775 capsule Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229960001993 deserpidine Drugs 0.000 description 1
ISMCNVNDWFIXLM-WCGOZPBSSA-N deserpidine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 ISMCNVNDWFIXLM-WCGOZPBSSA-N 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
XEHVFKKSDRMODV-UHFFFAOYSA-N ethynyl Chemical compound C#[C] XEHVFKKSDRMODV-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
108010020084 germin Proteins 0.000 description 1
RNPABQVCNAUEIY-UHFFFAOYSA-N germine Natural products O1C(C(CCC23C)O)(O)C3CC(O)C(C3(O)C(O)C(O)C4C5(C)O)C12CC3C4CN1C5CCC(C)C1 RNPABQVCNAUEIY-UHFFFAOYSA-N 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
229960002474 hydralazine Drugs 0.000 description 1
DMDGGSIALPNSEE-UHFFFAOYSA-N hydroflumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O DMDGGSIALPNSEE-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical class O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
229960004011 methenamine Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000001452 natriuretic effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229960001965 rescinnamine Drugs 0.000 description 1
SMSAPZICLFYVJS-QEGASFHISA-N rescinnamine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1 SMSAPZICLFYVJS-QEGASFHISA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 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
125000001424 substituent group Chemical group 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
210000002435 tendon Anatomy 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229940057613 veratrum Drugs 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
239000000080 wetting agent Substances 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)

CH7602559A 1958-07-31 1959-07-21 Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden CH382745A (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US75216558A	1958-07-31	1958-07-31
US76380658A	1958-09-29	1958-09-29
US812579A US3095446A (en)	1959-05-12	1959-05-12	Haloalkylaniline disulfonyl chlorides

Publications (1)

Publication Number	Publication Date
CH382745A true CH382745A (de)	1964-10-15

Family

ID=27419422

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7602559A CH382745A (de)	1958-07-31	1959-07-21	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden

Country Status (2)

Country	Link
CH (1)	CH382745A (da)
DK (1)	DK111073B (da)

1959
- 1959-07-21 CH CH7602559A patent/CH382745A/de unknown
- 1959-07-29 DK DK271759A patent/DK111073B/da unknown

Also Published As

Publication number	Publication date
DK111073B (da)	1968-05-27

Publication	Publication Date	Title
CH377365A (de)	1964-05-15	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
DE1793745A1 (de)	1973-05-30	Arylsubstituierte biguanide
DE2646676A1 (de)	1977-04-28	Pyrimidonderivate, verfahren zu ihrer herstellung und daraus hergestellte arzneimittel
DE2138331A1 (de)	1972-02-03	Thioacetamidverbindungen, Verfahren zu ihrer Herstellung und Arzneimittel
DE1023039B (de)	1958-01-23	Verfahren zur Herstellung von 5-Piperazino-pyridazon-(6)-verbindungen
CH382745A (de)	1964-10-15	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
EP0177907B1 (de)	1988-06-01	Neue 2-Pyridin-thiol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE3128386C2 (da)	1987-06-19
DE2417063C2 (de)	1982-05-13	Tricyclische Sulfoximid-Derivate
DE1802297A1 (de)	1969-07-24	Verfahren zur Herstellung von neuen Isopropyl-Derivaten
AT242700B (de)	1965-09-27	Verfahren zur Herstellung von neuen 3,4-Dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
DE1745778C3 (de)	1975-03-20	1-Methyl-2- eckige Klammer auf 2-(2-thienyl)-vinyl eckige Klammer zu -Delta hoch 2- tetrahydropyrimidin
DE924632C (de)	1955-03-07	Verfahren zur Herstellung von Dialkylxanthinabkoemmlingen
DE1301820B (de)	1969-08-28	5-[4-Phenylpiperazinoalkyl]-tetrazolderivate
DE1093370B (de)	1960-11-24	Verfahren zur Herstellung von 7-Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
DE1090215B (de)	1960-10-06	Verfahren zur Herstellung von Phenthiazinderivaten
DE1545955A1 (de)	1969-11-20	Verfahren zur Herstellung von Benzodiazepin-Derivaten
DE1966132B2 (de)	1981-07-23	7-Chlor-2-hydroxy-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin
AT223195B (de)	1962-09-10	Verfahren zur Herstellung von neuen 3,4-Dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
AT234696B (de)	1964-07-10	Verfahren zur Herstellung des neuen 3-Dichlormethyl-6-trifluormethyl-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyds
AT221523B (de)	1962-06-12	Verfahren zur Herstellung von neuen 3,4-Dihydro-1,2,4-benzothiadiazin-1,1-dioxyden und deren Salzen
DE1770104C3 (de)	1979-08-23	2- [(3,4-Dichlorphenoxy)-methyl] -2-unidazolin und seine Salze
CH382750A (de)	1964-10-15	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-pyrido-1,2,4-thiadiazin-1,1-dioxyden
DE867093C (de)	1953-02-16	Verfahren zur Herstellung von basischen Colchicinderivaten
DE1568552B2 (de)	1975-01-16	N-acylierte i-Chlorbenzol-24-disultonamJde und Verfahren zu ihrer Herstellung