CH387642A - 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: CH387642A
Authority: CH; Switzerland
Prior art keywords: benzothiadiazine; dihydro; sep; sulfamyl; starting materials
Prior art date: 1958-03-03

Application number

CH18463A

Other languages

German (de)

English (en)

Inventor

Destevens George

Harvey Werner Lincoln

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.)

1958-03-03

Filing date

1959-02-19

Publication date

1965-02-15

1959-02-19 Application filed by Ciba Geigy filed Critical Ciba Geigy

1965-02-15 Publication of CH387642A publication Critical patent/CH387642A/de

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 4
-1 haloalkyl radical Chemical class 0.000 claims description 11
239000007858 starting material Substances 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims 1
ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 claims 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
150000003839 salts Chemical class 0.000 description 6
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
239000007788 liquid Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
239000003795 chemical substances by application Substances 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
239000002934 diuretic Substances 0.000 description 2
229910052744 lithium Inorganic materials 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
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
235000011118 potassium hydroxide Nutrition 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
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 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
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
OKXYPUDKVYVJDI-UHFFFAOYSA-N 3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)NCNC2=C1 OKXYPUDKVYVJDI-UHFFFAOYSA-N 0.000 description 1
CVTBWXDLAWVRNO-UHFFFAOYSA-N 3-(bromomethyl)-6-chloro-1,1-dioxo-3,4-dihydro-2h-1$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
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 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
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
235000007265 Myrrhis odorata Nutrition 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
240000004760 Pimpinella anisum Species 0.000 description 1
235000012550 Pimpinella anisum Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-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
244000061121 Rauvolfia serpentina 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
241000489523 Veratrum Species 0.000 description 1
230000002378 acidificating effect Effects 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
229930013930 alkaloid Natural products 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 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
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
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 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
235000012000 cholesterol Nutrition 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
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 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
239000011521 glass Substances 0.000 description 1
229960002474 hydralazine Drugs 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000001452 natriuretic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 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
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux 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
229910052708 sodium Inorganic materials 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture 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
239000000725 suspension 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
238000004809 thin layer chromatography Methods 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
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
- C07D285/26—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals
- C07D285/28—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
- C07D285/26—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals
- C07D285/30—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals with hydrocarbon radicals, substituted by hetero atoms, attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH18463A 1958-03-03 1959-02-19 Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden CH387642A (de)

Applications Claiming Priority (10)

Application Number	Priority Date	Filing Date
US71845258A	1958-03-03	1958-03-03
US72724258A	1958-04-09	1958-04-09
US74058258A	1958-06-09	1958-06-09
US75162058A	1958-07-29	1958-07-29
US76448258A	1958-09-29	1958-09-29
DEC0028409		1959-02-27
DEC0028408		1959-02-27
DEC0024178		1959-02-27
DEC0024176		1959-02-27
DEC0024177		1959-02-27

Publications (1)

Publication Number	Publication Date
CH387642A true CH387642A (de)	1965-02-15

Family

ID=27579177

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
CH18463A CH387642A (de)	1958-03-03	1959-02-19	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
CH18163A CH377365A (de)	1958-03-03	1959-02-19	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
CH6978359A CH371454A (de)	1958-03-03	1959-02-19	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
CH18063A CH376514A (de)	1958-03-03	1959-02-19	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
CH18163A CH377365A (de)	1958-03-03	1959-02-19	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
CH6978359A CH371454A (de)	1958-03-03	1959-02-19	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
CH18063A CH376514A (de)	1958-03-03	1959-02-19	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden

Country Status (6)

Country	Link
CH (4)	CH387642A (fr)
DE (4)	DE1445574A1 (fr)
FR (2)	FR1217929A (fr)
GB (1)	GB861367A (fr)
MY (1)	MY6200051A (fr)
OA (2)	OA01178A (fr)

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US3200117A (en) *	1962-10-03	1965-08-10	Hoffmann La Roche	Derivatives of 1, 2, 4-benzothiadiazine-7-sulfonamide-1, 1-dioxide
DE2642140C2 (de) *	1976-09-20	1982-10-28	Degussa Ag, 6000 Frankfurt	Verfahren zur Herstellung von Benzoylcyanid
DE8700284U1 (de) *	1987-01-07	1987-04-30	Ernst Reiner GmbH & Co KG, 7743 Furtwangen	Post-Datumstempel
RU2214405C2 (ru) *	1998-02-18	2003-10-20	НьюроСёрч А/С	Новые соединения и их применение в качестве положительных модуляторов амра-рецепторов
US6943159B1 (en)	1998-02-18	2005-09-13	Neurosearch A/S	Compounds and their use as positive AMPA receptor modulators
US6982251B2 (en)	2000-12-20	2006-01-03	Schering Corporation	Substituted 2-azetidinones useful as hypocholesterolemic agents
KR20070120617A (ko)	2001-01-26	2007-12-24	쉐링 코포레이션	치환된 아제티딘온 화합물을 포함하는 약제학적 조성물
US7071181B2 (en)	2001-01-26	2006-07-04	Schering Corporation	Methods and therapeutic combinations for the treatment of diabetes using sterol absorption inhibitors
IL156445A0 (en)	2001-01-26	2004-01-04	Schering Corp	Combinations of peroxisome proliferator-activated receptor (ppar) activator(s) and sterol absorption inhibitor(s) and treatments for vascular indications
US7053080B2 (en)	2001-09-21	2006-05-30	Schering Corporation	Methods and therapeutic combinations for the treatment of obesity using sterol absorption inhibitors
EP1429756B1 (fr)	2001-09-21	2006-11-22	Schering Corporation	Methodes et combinaisons therapeutiques utiles pour le traitement du xanthome effectue avec des inhibiteurs d'absorption du sterol
US7056906B2 (en)	2001-09-21	2006-06-06	Schering Corporation	Combinations of hormone replacement therapy composition(s) and sterol absorption inhibitor(s) and treatments for vascular conditions in post-menopausal women
EA200500234A1 (ru)	2002-08-19	2005-08-25	Пфайзер Продактс Инк.	Комбинированная терапия гиперпролиферативных болезней
CA2504916A1 (fr)	2002-11-06	2004-05-27	Schering Corporation	Inhibiteurs d'absorption de cholesterol pour le traitement de troubles auto-immuns
WO2004081004A1 (fr)	2003-03-07	2004-09-23	Schering Corporation	Composes d'azetidinone substitues, formulations et utilisations de ceux-ci pour traiter l'hypercholesterolemie
WO2004081002A1 (fr)	2003-03-07	2004-09-23	Schering Corporation	Composes d'azetidinone substitues, leurs formulations et utilisations en vue du traitement de l'hypercholesterolemie
DE602004018617D1 (de)	2003-03-07	2009-02-05	Schering Corp	Substituierte azetidinon-derivate, deren pharmazeutische formulierungen und deren verwendung zur behandlung von hypercholesterolemia
US7459442B2 (en)	2003-03-07	2008-12-02	Schering Corporation	Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof
US7741317B2 (en)	2005-10-21	2010-06-22	Bristol-Myers Squibb Company	LXR modulators
US7888376B2 (en)	2005-11-23	2011-02-15	Bristol-Myers Squibb Company	Heterocyclic CETP inhibitors
ATE547394T1 (de)	2006-12-01	2012-03-15	Bristol Myers Squibb Co	N-((3-benzyl)-2,2-(bis-phenyl)-propan-1- aminderivate als cetp-hemmer für die behandlung von atherosklerose und herz-kreislauf- erkrankungen
US8969514B2 (en)	2007-06-04	2015-03-03	Synergy Pharmaceuticals, Inc.	Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
WO2008151257A2 (fr)	2007-06-04	2008-12-11	Synergy Pharmaceuticals Inc.	Agonistes de guanylase cyclase utiles pour le traitement de troubles gastro-intestinaux, d'inflammation, de cancer et d'autres troubles
ES2627848T3 (es)	2008-06-04	2017-07-31	Synergy Pharmaceuticals Inc.	Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos
ES2624828T3 (es)	2008-07-16	2017-07-17	Synergy Pharmaceuticals Inc.	Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros
US9616097B2 (en)	2010-09-15	2017-04-11	Synergy Pharmaceuticals, Inc.	Formulations of guanylate cyclase C agonists and methods of use
US9708367B2 (en)	2013-03-15	2017-07-18	Synergy Pharmaceuticals, Inc.	Agonists of guanylate cyclase and their uses
EP2968439A2 (fr)	2013-03-15	2016-01-20	Synergy Pharmaceuticals Inc.	Compositions utiles pour le traitement de troubles gastro-intestinaux
CN105143203A (zh)	2013-04-17	2015-12-09	辉瑞大药厂	用于治疗心血管疾病的n-哌啶-3-基苯甲酰胺衍生物
PL3004138T3 (pl)	2013-06-05	2024-07-29	Bausch Health Ireland Limited	Ultra-oczyszczeni agoniści peptydowi cyklazy guanylanowej C, sposób ich uzyskiwania i ich zastosowanie
WO2016055901A1 (fr)	2014-10-08	2016-04-14	Pfizer Inc.	Composés d'amide substitué
WO2020150473A2 (fr)	2019-01-18	2020-07-23	Dogma Therapeutics, Inc.	Inhibiteurs de pcsk9 et leurs procédés d'utilisation

1958
- 1958-12-16 FR FR781736A patent/FR1217929A/fr not_active Expired
1959
- 1959-02-19 CH CH18463A patent/CH387642A/de unknown
- 1959-02-19 CH CH18163A patent/CH377365A/de unknown
- 1959-02-19 CH CH6978359A patent/CH371454A/de unknown
- 1959-02-19 CH CH18063A patent/CH376514A/de unknown
- 1959-02-27 DE DE19591445574 patent/DE1445574A1/de active Pending
- 1959-02-27 DE DEC18496A patent/DE1112079B/de active Pending
- 1959-02-27 DE DE19591445007 patent/DE1445007A1/de active Pending
- 1959-02-27 DE DE19591445005 patent/DE1445005A1/de active Pending
- 1959-03-02 GB GB7209/59A patent/GB861367A/en not_active Expired
- 1959-03-03 FR FR788246A patent/FR1264468A/fr not_active Expired
1962
- 1962-12-30 MY MY51/62A patent/MY6200051A/xx unknown
1964
- 1964-12-31 OA OA51359A patent/OA01178A/fr unknown
1965
- 1965-06-29 OA OA52080A patent/OA03826A/fr unknown

Also Published As

Publication number	Publication date
DE1445007A1 (de)	1968-10-24
CH376514A (de)	1964-04-15
MY6200051A (en)	1962-12-31
DE1112079B (de)	1961-08-03
FR1264468A (fr)	1961-06-23
DE1445005A1 (de)	1968-10-24
DE1445006A1 (de)	1968-10-24
CH377365A (de)	1964-05-15
OA01178A (fr)	1969-01-25
DE1445008A1 (de)	1968-10-24
CH371454A (de)	1963-08-31
DE1445006B2 (fr)	1975-05-07
DE1445574A1 (de)	1969-01-16
GB861367A (en)	1961-02-22
OA03826A (fr)	1971-12-24
FR1217929A (fr)	1960-05-06

Publication	Publication Date	Title
CH377365A (de)	1964-05-15	Verfahren zur Herstellung von Sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
DE1914571B2 (de)	1978-01-12	L-3hydroxy-6-oxomorphinan-verbindungen
AT223199B (de)	1962-09-10	Verfahren zur Herstellung von neuen 3,4-Dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
DE1620572B1 (de)	1971-10-14	Pyrido Ä2,3-bÜ Ä1,4Ü benzodiazepinderivate und ein Verfahren zu ihrer Herstellung
AT222117B (de)	1962-07-10	Verfahren zur Herstellung neuer Azabenz-imidazole
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
AT224642B (de)	1962-12-10	Verfahren zur Herstellung von neuen 3,4-Dihydro-1,2,4-benzothiadiazin-1,1-dioxyden
AT239227B (de)	1965-03-25	Verfahren zur Herstellung des neuen 6-Chlor-7-sulfamyl-3, 4-dihydro-1, 2, 4-benzothiadiazin-1, 1-dioxyds
AT287720B (de)	1971-02-10	Verfahren zur Herstellung von neuen 1-(2-Pyridyl)-1,2,3,4-tetrahydro-isochinolinen sowie deren Säureadditionssalzen
DE1812073A1 (de)	1969-07-10	Verfahren zur Herstellung neuer tricyclischer Verbindungen und neue tricyclische Verbindungen
DE2015321A1 (en)	1970-10-08	Novel guanidine derivs
AT262255B (de)	1968-06-10	Verfahren zur Herstellung des neuen 2-(2',3',5',6'-Tetramethylbenzyl)-2-propylamins und dessen Salze
AT347423B (de)	1978-12-27	Verfahren zur herstellung von neuen 7- aminobenzocycloheptenen und von deren salzen
AT255422B (de)	1967-07-10	Verfahren zur Herstellung von neuen Iminodibenzylderivaten
AT236378B (de)	1964-10-26	Verfahren zur Herstellung von neuen tricyclischen Verbindungen
AT200142B (de)	1958-10-25	Verfahren zur Herstellung von neuen Pyrazolidinderivaten
DE1493513A1 (de)	1969-05-14	Neue Anthranilsaeurederivate
AT221523B (de)	1962-06-12	Verfahren zur Herstellung von neuen 3,4-Dihydro-1,2,4-benzothiadiazin-1,1-dioxyden und deren Salzen
AT332408B (de)	1976-09-27	Verfahren zur herstellung neuer chinolinverbindungen und ihrer salze
AT238202B (de)	1965-01-25	Verfahren zur Herstellung von neuen Isochinolinderivaten
AT221089B (de)	1962-05-10	Verfahren zur Herstellung neuer Azabenz-imidazole
AT205968B (de)	1959-10-26	Verfahren zur Herstellung neuer Benzimidazole
AT345838B (de)	1978-10-10	Verfahren zur herstellung von neuen tricyclischen verbindungen und ihren saeure- additionssalzen
DE1966128A1 (de)	1971-08-12	Neue 5-Phenyl-1H-1,5-benzodiazepin-2,4-dione
AT294809B (de)	1971-12-10	Verfahren zur Herstellung von neuen p-Aminobenzoesäureaniliden und deren Salzen