NO830611L - Imidazotiadiazolalkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendles i legemidler - Google Patents

Imidazotiadiazolalkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendles i legemidler

Info

Publication number: NO830611L
Authority: NO; Norway
Prior art keywords: alkyl; different; optionally; general formula; halogen
Prior art date: 1982-03-09

Application number

NO830611A

Other languages

English (en)

Norwegian (no)

Inventor

Axel Ingendoh

Horst Meyer

Bernward Garthoff

Original Assignee

Bayer 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.)

1982-03-09

Filing date

1983-02-22

Publication date

1983-09-12

1983-02-22 Application filed by Bayer Ag filed Critical Bayer Ag

1983-09-12 Publication of NO830611L publication Critical patent/NO830611L/no

Links

150000001408 amides Chemical class 0.000 title claims abstract description 14
238000002360 preparation method Methods 0.000 title claims description 14
239000003814 drug Substances 0.000 title claims description 6
239000000543 intermediate Substances 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 72
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
239000001257 hydrogen Substances 0.000 claims abstract description 45
229910052736 halogen Inorganic materials 0.000 claims abstract description 41
150000002367 halogens Chemical group 0.000 claims abstract description 41
125000003545 alkoxy group Chemical group 0.000 claims abstract description 35
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 33
229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
125000003118 aryl group Chemical group 0.000 claims abstract description 26
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 25
239000001301 oxygen Substances 0.000 claims abstract description 24
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
229910052717 sulfur Inorganic materials 0.000 claims abstract description 22
239000002253 acid Substances 0.000 claims abstract description 21
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 18
125000005842 heteroatom Chemical group 0.000 claims abstract description 16
229920006395 saturated elastomer Polymers 0.000 claims abstract description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 14
-1 NH or N-alkyl Chemical compound 0.000 claims abstract description 13
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
125000001424 substituent group Chemical group 0.000 claims abstract description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 9
239000005864 Sulphur Substances 0.000 claims abstract description 8
125000004122 cyclic group Chemical group 0.000 claims abstract description 8
125000002541 furyl group Chemical group 0.000 claims abstract description 8
125000004076 pyridyl group Chemical group 0.000 claims abstract description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 8
239000002934 diuretic Substances 0.000 claims abstract description 7
125000001544 thienyl group Chemical group 0.000 claims abstract description 7
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
150000001412 amines Chemical class 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
229940030606 diuretics Drugs 0.000 claims abstract description 4
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 4
125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 4
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
229940116731 Uricosuric agent Drugs 0.000 claims abstract description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 4
125000004432 carbon atom Chemical group C* 0.000 claims description 58
150000002431 hydrogen Chemical class 0.000 claims description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 22
238000000034 method Methods 0.000 claims description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
150000001728 carbonyl compounds Chemical class 0.000 claims description 11
239000003960 organic solvent Substances 0.000 claims description 11
239000011593 sulfur Substances 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
230000003424 uricosuric effect Effects 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
239000000969 carrier Substances 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
150000003869 acetamides Chemical class 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
230000004913 activation Effects 0.000 claims description 3
239000002220 antihypertensive agent Substances 0.000 claims description 3
229940030600 antihypertensive agent Drugs 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
150000001299 aldehydes Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
125000004971 nitroalkyl group Chemical group 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
201000010099 disease Diseases 0.000 claims 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
229910052799 carbon Inorganic materials 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
125000005493 quinolyl group Chemical group 0.000 claims 1
239000003383 uricosuric agent Substances 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 7
239000000126 substance Substances 0.000 description 7
BOXRDDIXJOUZLV-UHFFFAOYSA-N 2h-imidazo[4,5-d]thiadiazole Chemical class N1SC2=NC=NC2=N1 BOXRDDIXJOUZLV-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
210000002700 urine Anatomy 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 3
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000013543 active substance Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
230000001882 diuretic effect Effects 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
230000029142 excretion Effects 0.000 description 3
238000009472 formulation Methods 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
229960003531 phenolsulfonphthalein Drugs 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
230000000894 saliuretic effect Effects 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
GLYQQFBHCFPEEU-UHFFFAOYSA-N 5-bromo-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(Br)S1 GLYQQFBHCFPEEU-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
230000008033 biological extinction Effects 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
125000005265 dialkylamine group Chemical group 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003792 electrolyte Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
238000011010 flushing procedure Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000003826 tablet Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
LDDMACCNBZAMSG-BDVNFPICSA-N (2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal Chemical compound CN[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO LDDMACCNBZAMSG-BDVNFPICSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
OVTYQHASJXYMLQ-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole-2-sulfonamide Chemical class C1=NC2=NC(S(=O)(=O)N)SC2=N1 OVTYQHASJXYMLQ-UHFFFAOYSA-N 0.000 description 1
101150090724 3 gene Proteins 0.000 description 1
208000009304 Acute Kidney Injury Diseases 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
239000004097 EU approved flavor enhancer Substances 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
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
208000033626 Renal failure acute Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
201000011040 acute kidney failure Diseases 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
238000010171 animal model Methods 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
239000002969 artificial stone Substances 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
230000036765 blood level Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000002497 edematous effect Effects 0.000 description 1
239000008151 electrolyte solution Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
244000243234 giant cane Species 0.000 description 1
229960002442 glucosamine Drugs 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
159000000014 iron salts Chemical class 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000007788 liquid Substances 0.000 description 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 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
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
150000004760 silicates Chemical class 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
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
125000005106 triarylsilyl group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
210000003932 urinary bladder Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Hematology (AREA)
Diabetes (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Lubricants (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Macromonomer-Based Addition Polymer (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO830611A 1982-03-09 1983-02-22 Imidazotiadiazolalkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendles i legemidler NO830611L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19823208437 DE3208437A1 (de)	1982-03-09	1982-03-09	Imidazothiadiazolalkencarbonsaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln

Publications (1)

Publication Number	Publication Date
NO830611L true NO830611L (no)	1983-09-12

Family

ID=6157723

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO830611A NO830611L (no)	1982-03-09	1983-02-22	Imidazotiadiazolalkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendles i legemidler

Country Status (12)

Country	Link
US (4)	US4585873A (fr)
EP (1)	EP0088323B1 (fr)
JP (1)	JPS58162593A (fr)
AT (1)	ATE26984T1 (fr)
AU (1)	AU1193483A (fr)
CA (1)	CA1215710A (fr)
DE (2)	DE3208437A1 (fr)
DK (1)	DK113283A (fr)
ES (1)	ES8401086A1 (fr)
GR (1)	GR77427B (fr)
NO (1)	NO830611L (fr)
ZA (1)	ZA831574B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE102005010215A1 (de) *	2005-03-05	2006-09-07	Bayer Cropscience Ag	Heterobicyclische Acrylamide
US8563550B2 (en)	2007-09-27	2013-10-22	Centro Nacional De Investigaciones Oncologicas (Cnio)	Imidazolothiadiazoles for use as protein kinase inhibitors
DK2414369T3 (en)	2009-04-02	2015-09-21	Fundacion Ct Nac Investigaciones Oncologicas Carlos Iii	Imidazo [2,1-b] [1,3,4] thiadiazole derivatives
US9173887B2 (en)	2010-12-22	2015-11-03	Abbvie Inc.	Hepatitis C inhibitors and uses thereof
CN114787167B (zh)	2019-10-21	2024-06-21	诺华股份有限公司	用于治疗寄生虫病的化合物及组合物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3946031A (en) *	1973-10-04	1976-03-23	Syntex Inc.	2-Substituted-1,2,4-thiadiazolo-[2,3-a]-benzimidazoles
DE2823686A1 (de) *	1978-05-31	1979-12-06	Bayer Ag	Imidazo eckige klammer auf 2.1-b eckige klammer zu eckige klammer auf 1.3.4 eckige klammer zu -thiadiazole
NO811630L (no) *	1980-05-29	1981-11-30	Bayer Ag	Imidazoazolalkensyreamider, nye mellomprodukter for deres fremstilling, deres fremstilling og deres anvendelse som legemiddel

1982
- 1982-03-09 DE DE19823208437 patent/DE3208437A1/de not_active Withdrawn
1983
- 1983-02-22 NO NO830611A patent/NO830611L/no unknown
- 1983-02-22 US US06/468,737 patent/US4585873A/en not_active Expired - Fee Related
- 1983-02-28 DE DE8383101929T patent/DE3371339D1/de not_active Expired
- 1983-02-28 EP EP83101929A patent/EP0088323B1/fr not_active Expired
- 1983-02-28 AT AT83101929T patent/ATE26984T1/de active
- 1983-03-01 AU AU11934/83A patent/AU1193483A/en not_active Abandoned
- 1983-03-04 JP JP58034671A patent/JPS58162593A/ja active Pending
- 1983-03-07 CA CA000423009A patent/CA1215710A/fr not_active Expired
- 1983-03-07 GR GR70699A patent/GR77427B/el unknown
- 1983-03-08 ZA ZA831574A patent/ZA831574B/xx unknown
- 1983-03-08 DK DK113283A patent/DK113283A/da not_active Application Discontinuation
- 1983-03-08 ES ES520398A patent/ES8401086A1/es not_active Expired
1985
- 1985-10-21 US US06/789,689 patent/US4657905A/en not_active Expired - Fee Related
1986
- 1986-07-01 US US06/880,752 patent/US4703125A/en not_active Expired - Fee Related
- 1986-07-11 US US06/884,561 patent/US4709031A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US4703125A (en)	1987-10-27
JPS58162593A (ja)	1983-09-27
US4585873A (en)	1986-04-29
ATE26984T1 (de)	1987-05-15
DE3208437A1 (de)	1983-09-15
DK113283D0 (da)	1983-03-08
US4709031A (en)	1987-11-24
DE3371339D1 (en)	1987-06-11
ES520398A0 (es)	1983-12-01
ZA831574B (en)	1983-12-28
EP0088323A3 (en)	1984-08-01
CA1215710A (fr)	1986-12-23
AU1193483A (en)	1983-09-15
ES8401086A1 (es)	1983-12-01
EP0088323B1 (fr)	1987-05-06
DK113283A (da)	1983-09-10
US4657905A (en)	1987-04-14
EP0088323A2 (fr)	1983-09-14
GR77427B (fr)	1984-09-14

Publication	Publication Date	Title
US4307095A (en)	1981-12-22	Method of treating schizophrenia with cycloalkltriazoles
US4399136A (en)	1983-08-16	Pyrazolopyridazine antihypertensives
WO2010132999A1 (fr)	2010-11-25	Méthylsulfanylpyrimidines utiles en tant qu'agents anti-inflammatoires, analgésiques, et anti-épileptiques
PT89020B (pt)	1993-02-26	Processo para a preparacao de 3-{4(1-substituidas -4-piperazinil)butil}-4-tiazolidinonas e de composicoes farmaceuticas que as contem
NO811630L (no)	1981-11-30	Imidazoazolalkensyreamider, nye mellomprodukter for deres fremstilling, deres fremstilling og deres anvendelse som legemiddel
NO315373B1 (no)	2003-08-25	Spirosykliske metallprotease-inhibitorer
US3472848A (en)	1969-10-14	3-hydroxy and 3-mercapto-pyrazinoyl-guanidines,corresponding ethers and thioethers and processes for their preparation
DK168010B1 (da)	1994-01-17	Tetrahydroisoquinolinforbindelser og farmaceutisk middel indeholdende en saadan forbindelse
NO830611L (no)	1983-09-12	Imidazotiadiazolalkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendles i legemidler
Thirtle	1946	2-Mercaptopyridine
DK162999B (da)	1992-01-06	Imidazoquinazolinforbindelse samt fremgangsmaade til fremstilling deraf
US4054652A (en)	1977-10-18	Dihydro- and tetrahydro- iminothiazines
KR900004828B1 (ko)	1990-07-07	페닐-나프티리딘의 제조방법
US4091105A (en)	1978-05-23	2-Imino-3-aminothiazolidines and indoleamine-N-methyltransferase inhibition
CS244145B2 (en)	1986-07-17	Method of 4,5,6,7-tetrahydrothiazolo-(5,4-c)pyridine derivatives production
DK155009B (da)	1989-01-23	Analogifremgangsmaade til fremstilling af thienooe2,3-eaa-1,2-thiazin-1,1-dioxidderivat eller farmaceutisk tolerable salte heraf samt udgangsmateriale til brug ved fremgangsmaaden
US3787419A (en)	1974-01-22	N-substituted-alpha,alpha,alpha-trifluoro-m-toluamides
DK170047B1 (da)	1995-05-08	Med basiske heterocycliske grupper substituerede 5-halogen-thienoisothiazol-3(2H)-on-1,1-dioxider og salte deraf, fremgangsmåde til fremstilling af sådanne forbindelser, farmaceutiske præparater indeholdende disse forbindelser og forbindelsernes anvendelse ved fremstilling af lægemidler til behandling af angsttilstande
US4325952A (en)	1982-04-20	Method of treating abstinence syndrome with cycloaklyltriazoles
US4025508A (en)	1977-05-24	6-(Trifluoromethyl)-benzothiadiazines
US3752820A (en)	1973-08-14	Substituted-1,2,3,4-tetrahydrobenzothieno(3,2-c)pyridine derivatives
JPS6130676B2 (fr)	1986-07-15
US4397849A (en)	1983-08-09	Benzothiazine derivatives
CS227001B2 (en)	1984-04-16	Method of preparing thiazoloisoquinoline derivatives
US4588723A (en)	1986-05-13	Aminoalkyl-imidazothiadiazole-alkenecarboxylic acid amides, intermediates for their preparation and their use in medicaments