CA1056828A - Preparation de derives de type 2,1,4-benzothiadiazine - Google Patents

Preparation de derives de type 2,1,4-benzothiadiazine

Info

Publication number: CA1056828A
Authority: CA; Canada
Prior art keywords: methyl; carbamate; phenoxy; nitro; formula
Prior art date: 1973-06-26
Legal status (The legal status 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 status listed.): Expired

Application number

CA275,194A

Other languages

English (en)

Inventor

Heinz Loewe

Dieter Duwel

Reinhard Kirsch

Josef Urbanietz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1973-06-26

Filing date

1977-03-31

Publication date

1979-06-19

1973-06-26 Priority claimed from DE2332486A external-priority patent/DE2332486A1/de

1974-06-25 Priority claimed from CA203,354A external-priority patent/CA1025454A/fr

1977-03-31 Application filed by Hoechst AG filed Critical Hoechst AG

1977-03-31 Priority to CA275,194A priority Critical patent/CA1056828A/fr

1979-06-19 Application granted granted Critical

1979-06-19 Publication of CA1056828A publication Critical patent/CA1056828A/fr

Status Expired legal-status Critical Current

Links

NLXPDNKIQMAKCH-UHFFFAOYSA-N 1h-2,1,4-benzothiadiazine Chemical class C1=CC=C2NSC=NC2=C1 NLXPDNKIQMAKCH-UHFFFAOYSA-N 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 title claims abstract description 9
238000000034 method Methods 0.000 claims abstract description 19
150000001340 alkali metals Chemical class 0.000 claims abstract description 6
XDIFNJUJJYNUIN-UHFFFAOYSA-N (2-nitrophenyl)carbamothioyl carbamate Chemical compound C(N)(OC(NC1=C(C=CC=C1)[N+](=O)[O-])=S)=O XDIFNJUJJYNUIN-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
239000012670 alkaline solution Substances 0.000 claims abstract description 5
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims abstract description 5
150000004965 peroxy acids Chemical class 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
229910052801 chlorine Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 claims 1
241001465754 Metazoa Species 0.000 abstract description 6
150000003568 thioethers Chemical class 0.000 abstract description 5
244000045947 parasite Species 0.000 abstract description 4
239000002246 antineoplastic agent Substances 0.000 abstract description 2
229940127089 cytotoxic agent Drugs 0.000 abstract description 2
201000010099 disease Diseases 0.000 abstract description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
125000001424 substituent group Chemical group 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract 1
238000002844 melting Methods 0.000 description 72
230000008018 melting Effects 0.000 description 72
-1 methoxy, ethoxy, propoxy, isopropoxy Chemical group 0.000 description 43
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 14
150000001875 compounds Chemical class 0.000 description 13
239000000203 mixture Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000013543 active substance Substances 0.000 description 9
238000004519 manufacturing process Methods 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002585 base Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000007658 benzothiadiazines Chemical class 0.000 description 4
230000000694 effects Effects 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
150000001556 benzimidazoles Chemical class 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
235000013601 eggs Nutrition 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
238000011282 treatment Methods 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
RGJVVCCIZKLJRL-UHFFFAOYSA-N 2-chloro-3-nitro-1h-pyridin-4-one Chemical compound OC1=CC=NC(Cl)=C1[N+]([O-])=O RGJVVCCIZKLJRL-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
ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
YRWLZFXJFBZBEY-UHFFFAOYSA-N N-(6-butyl-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 YRWLZFXJFBZBEY-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
210000003608 fece Anatomy 0.000 description 2
150000002500 ions Chemical class 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
OPXLLQIJSORQAM-UHFFFAOYSA-N mebendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1C(=O)C1=CC=CC=C1 OPXLLQIJSORQAM-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000011593 sulfur Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
YPSTVMOYFVCBAS-UHFFFAOYSA-N 1-nitro-1-thiophen-2-ylurea Chemical class [N+](=O)([O-])N(C(=O)N)C=1SC=CC=1 YPSTVMOYFVCBAS-UHFFFAOYSA-N 0.000 description 1
WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical compound C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 description 1
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
FSGTULQLEVAYRS-UHFFFAOYSA-N 4,5-dichloro-2-nitroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O FSGTULQLEVAYRS-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
NXPKLPJNWFHUSK-UHFFFAOYSA-N C(N)(OC(C)CC)=O.O(C1=CC=CC=C1)C1=CC2=C(N=CN2)C=C1 Chemical compound C(N)(OC(C)CC)=O.O(C1=CC=CC=C1)C1=CC2=C(N=CN2)C=C1 NXPKLPJNWFHUSK-UHFFFAOYSA-N 0.000 description 1
QQPBIBKTTJBCTN-UHFFFAOYSA-N C(N)(OCC(NC1=C(C=CC(=C1)OC1=CC=CC=C1)[N+](=O)[O-])=S)=O Chemical compound C(N)(OCC(NC1=C(C=CC(=C1)OC1=CC=CC=C1)[N+](=O)[O-])=S)=O QQPBIBKTTJBCTN-UHFFFAOYSA-N 0.000 description 1
NFOLEKQSKIQPKQ-UHFFFAOYSA-N CC1=CC=C(OC2=CC3=C(N=CN3)C=C2)C=C1 Chemical compound CC1=CC=C(OC2=CC3=C(N=CN3)C=C2)C=C1 NFOLEKQSKIQPKQ-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241001126268 Cooperia Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000243976 Haemonchus Species 0.000 description 1
241000243974 Haemonchus contortus Species 0.000 description 1
241000920462 Heterakis Species 0.000 description 1
241001547406 Hyostrongylus Species 0.000 description 1
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 1
206010061217 Infestation Diseases 0.000 description 1
241000510960 Oesophagostomum Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241001494479 Pecora Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
241000282849 Ruminantia Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000244174 Strongyloides Species 0.000 description 1
241000193803 Therea Species 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
241000243796 Trichostrongylus colubriformis Species 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000000507 anthelmentic effect Effects 0.000 description 1
229940124339 anthelmintic agent Drugs 0.000 description 1
239000000921 anthelmintic agent Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 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
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
238000005352 clarification Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
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150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
244000000013 helminth Species 0.000 description 1
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
229910052500 inorganic mineral Chemical class 0.000 description 1
238000002955 isolation Methods 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
239000011707 mineral Chemical class 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000008063 pharmaceutical solvent Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
YOSOSDBZAUWJJT-UHFFFAOYSA-L sodium dithionite monohydrate Chemical compound O.[Na+].[Na+].[O-]S(=O)S([O-])=O YOSOSDBZAUWJJT-UHFFFAOYSA-L 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000003460 sulfonic acids Chemical class 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
239000002562 thickening agent Substances 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CA275,194A 1973-06-26 1977-03-31 Preparation de derives de type 2,1,4-benzothiadiazine Expired CA1056828A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA275,194A CA1056828A (fr)	1973-06-26	1977-03-31	Preparation de derives de type 2,1,4-benzothiadiazine

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE2332486A DE2332486A1 (de)	1973-06-25	1973-06-26	2-carbalkoxy-amino-benzimidazol-5(6)phenylaether, ihre herstellung und verwendung in mitteln gegen helminthen
CA203,354A CA1025454A (fr)	1973-06-26	1974-06-25	Ethers 2-carbalkoxy-amino-benzimidazole-5(6)-phenyl, etc.
CA275,194A CA1056828A (fr)	1973-06-26	1977-03-31	Preparation de derives de type 2,1,4-benzothiadiazine

Publications (1)

Publication Number	Publication Date
CA1056828A true CA1056828A (fr)	1979-06-19

Family

ID=27163521

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA275,194A Expired CA1056828A (fr)	1973-06-26	1977-03-31	Preparation de derives de type 2,1,4-benzothiadiazine

Country Status (1)

Country	Link
CA (1)	CA1056828A (fr)

1977
- 1977-03-31 CA CA275,194A patent/CA1056828A/fr not_active Expired

Publication	Publication Date	Title
US3954791A (en)	1976-05-04	Anthelmintically active 2-carbalkoxy-amino-benzimidazole-5(6)-phenyl ethers
JPS5939428B2 (ja)	1984-09-22	駆虫効果を有する５（６）−ベンゼン環置換ベンズイミダゾ−ル−２−カルバメ−ト誘導体の製造方法
US4188486A (en)	1980-02-12	2-Substituted benzimidazole compounds
FI71148B (fi)	1986-08-14	Foerfarande foer framstaellning av nya antihypertensiva 4h-1,2,4-triazolo(4,3-a)kinoxalin-4-oner
IE42109B1 (en)	1980-06-04	5(6)-substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
US4259344A (en)	1981-03-31	Sulfur-containing benzimidazole derivatives
US4002640A (en)	1977-01-11	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
US3965113A (en)	1976-06-22	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
CA2211444C (fr)	2002-07-09	Nouveaux derives de benzimidazole, de benzoxazole et de benzothiazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CA1059135A (fr)	1979-07-24	Derives anthelminthiques de la 2-carbalkoxyamino-5 (6)-phenylsulfonyloxybenzimidazole et procede pour leur fabrication
CA1059136A (fr)	1979-07-24	Derives anthelminthiques d'esters phenyliques de l'acide 2-carbalkoxyaminobenzimidazolyl-5 (6) sulfonique et procede pour leur fabrication
CA1287631C (fr)	1991-08-13	Derives de substitution en 5 de pyrimidin-6-amine
US3928375A (en)	1975-12-23	Anthelmintically active 2-carbalkoxy-amino-benzimidazolyl-5(6)-amino-phenyl ethers
CS268191B2 (en)	1990-03-14	Method of new 4,5-dihydrooxazole derivatives production
CA1056828A (fr)	1979-06-19	Preparation de derives de type 2,1,4-benzothiadiazine
US4192880A (en)	1980-03-11	2-Substituted benzimidazole compounds
US4010272A (en)	1977-03-01	Anthelmintically active basically substituted 2-carbalkoxy-amino-benzimidazolyl-5(6)-phenyl ethers and -ketones
US3984561A (en)	1976-10-05	Anthelmintically active 2-carbalkoxy-amino-benzimidazole-5(6)-phenyl ethers and method for using the same
EP0358571A1 (fr)	1990-03-14	Thioformamidines, leur préparation et leur application en tant que médicaments
EP0412529B1 (fr)	1994-03-09	Dérivés d'imidazole, procédé de leur préparation et agents anti-ulcère les contenant
NO174465B (no)	1994-01-31	Analogifremgangsmaate ved fremstilling av terapeutisk 1-acyl- 2,3-dihydro-4-(1H)-kinolinon-4-oksimderi-vater
JPS5976050A (ja)	1984-04-28	置換されたベンゼンスルホン酸エステルおよびそれらの製造法
DE4341663A1 (de)	1995-06-08	Anellierte 2-Oxopiperazine, ihre Herstellung und Verwendung
JP2816974B2 (ja)	1998-10-27	ベンズイミダゾール誘導体およびその製造法ならびにこれを含有する抗潰瘍剤
NO763196L (no)	1977-03-22	Fremgangsm}te til fremstilling av antelmintisk virksomme 2-karbalkoksyamino-5(6)-fenyl-sulfonyloksy-benzimidazoler.