NO811630L - Imidazoazolalkensyreamider, nye mellomprodukter for deres fremstilling, deres fremstilling og deres anvendelse som legemiddel - Google Patents

Imidazoazolalkensyreamider, nye mellomprodukter for deres fremstilling, deres fremstilling og deres anvendelse som legemiddel

Info

Publication number: NO811630L
Authority: NO; Norway
Prior art keywords: alkyl; phenyl; general formula; alkoxy; atoms
Prior art date: 1980-05-29

Application number

NO811630A

Other languages

English (en)

Norwegian (no)

Inventor

Horst Meyer

Harald Horstmann

Eike Moeller

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.)

1980-05-29

Filing date

1981-05-13

Publication date

1981-11-30

1980-05-29 Priority claimed from DE19803020421 external-priority patent/DE3020421A1/de

1980-11-15 Priority claimed from DE19803043158 external-priority patent/DE3043158A1/de

1981-05-13 Application filed by Bayer Ag filed Critical Bayer Ag

1981-11-30 Publication of NO811630L publication Critical patent/NO811630L/no

Links

239000002253 acid Substances 0.000 title claims description 25
238000002360 preparation method Methods 0.000 title claims description 14
239000013067 intermediate product Substances 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims description 97
125000004432 carbon atom Chemical group C* 0.000 claims description 65
229910052739 hydrogen Inorganic materials 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 48
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 47
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
125000003545 alkoxy group Chemical group 0.000 claims description 41
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
229910052717 sulfur Inorganic materials 0.000 claims description 39
229910052757 nitrogen Inorganic materials 0.000 claims description 37
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 27
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
239000000460 chlorine Chemical group 0.000 claims description 26
229910052801 chlorine Inorganic materials 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 24
238000000034 method Methods 0.000 claims description 24
239000011737 fluorine Chemical group 0.000 claims description 23
229910052731 fluorine Inorganic materials 0.000 claims description 23
-1 cyano, hydroxyl Chemical group 0.000 claims description 22
125000003118 aryl group Chemical group 0.000 claims description 18
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
229910052794 bromium Chemical group 0.000 claims description 16
229910052736 halogen Chemical group 0.000 claims description 16
150000002367 halogens Chemical group 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
125000001153 fluoro group Chemical group F* 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
239000003960 organic solvent Substances 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
125000000304 alkynyl group Chemical group 0.000 claims description 10
150000001728 carbonyl compounds Chemical class 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 8
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
150000002429 hydrazines Chemical class 0.000 claims description 6
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
125000003373 pyrazinyl group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
125000005493 quinolyl group Chemical group 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
125000005956 isoquinolyl group Chemical group 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
239000000969 carrier Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 4
230000005494 condensation Effects 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-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
150000001408 amides Chemical class 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
150000002148 esters Chemical class 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
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 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 6
TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims 3
125000001931 aliphatic group Chemical group 0.000 claims 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000000725 suspension Substances 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
241000700159 Rattus Species 0.000 description 7
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
239000000243 solution Substances 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000000126 substance Substances 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
239000002585 base Substances 0.000 description 5
230000001882 diuretic effect Effects 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
230000029142 excretion Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000002934 diuretic Substances 0.000 description 4
239000000706 filtrate Substances 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
229960003531 phenolsulfonphthalein Drugs 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
230000003424 uricosuric effect Effects 0.000 description 4
210000002700 urine Anatomy 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
241000699670 Mus sp. Species 0.000 description 3
208000004880 Polyuria Diseases 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
239000013543 active substance Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
230000000894 saliuretic effect Effects 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007858 starting material Substances 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
125000004522 1,3,4-thiadiazol-5-yl group Chemical group S1C=NN=C1* 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
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
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
150000001299 aldehydes Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
229940030600 antihypertensive agent Drugs 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
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
229940030606 diuretics Drugs 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
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 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
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000004575 stone Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
QBBKKFZGCDJDQK-SSDOTTSWSA-N (2r)-2-ethylpiperidine Chemical compound CC[C@@H]1CCCCN1 QBBKKFZGCDJDQK-SSDOTTSWSA-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
UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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 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
QBBKKFZGCDJDQK-UHFFFAOYSA-N 2-ethylpiperidine Chemical compound CCC1CCCCN1 QBBKKFZGCDJDQK-UHFFFAOYSA-N 0.000 description 1
UMZCLZPXPCNKML-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole Chemical class C1=NC2=NCSC2=N1 UMZCLZPXPCNKML-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
101150034533 ATIC gene Proteins 0.000 description 1
208000009304 Acute Kidney Injury Diseases 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
240000002470 Amphicarpaea bracteata Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
101100257262 Caenorhabditis elegans soc-1 gene Proteins 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
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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
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 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000276498 Pollachius virens Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
208000033626 Renal failure acute Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
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
229940116731 Uricosuric agent Drugs 0.000 description 1
GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
201000011040 acute kidney failure Diseases 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000008055 alkyl aryl sulfonates 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
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 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
239000007900 aqueous suspension Substances 0.000 description 1
239000002969 artificial stone Substances 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
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000036772 blood pressure Effects 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
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
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001514 detection method Methods 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
238000007865 diluting Methods 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
230000002497 edematous effect Effects 0.000 description 1
239000008151 electrolyte solution Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 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
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
235000019264 food flavour enhancer Nutrition 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
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
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
159000000014 iron salts Chemical class 0.000 description 1
OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical group OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 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
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
230000014759 maintenance of location Effects 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000004060 metabolic process 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
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
YPEWWOUWRRQBAX-UHFFFAOYSA-N n,n-dimethyl-3-oxobutanamide Chemical compound CN(C)C(=O)CC(C)=O YPEWWOUWRRQBAX-UHFFFAOYSA-N 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
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003208 petroleum Substances 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
239000010773 plant oil Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000021395 porridge 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
235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 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
238000003756 stirring Methods 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
238000004809 thin layer chromatography Methods 0.000 description 1
239000003440 toxic substance Substances 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
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

NO811630A 1980-05-29 1981-05-13 Imidazoazolalkensyreamider, nye mellomprodukter for deres fremstilling, deres fremstilling og deres anvendelse som legemiddel NO811630L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19803020421 DE3020421A1 (de)	1980-05-29	1980-05-29	Imidazoazolalkensaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln
DE19803043158 DE3043158A1 (de)	1980-11-15	1980-11-15	Imidazoazolalkensaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln

Publications (1)

Publication Number	Publication Date
NO811630L true NO811630L (no)	1981-11-30

Family

ID=25785736

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO811630A NO811630L (no)	1980-05-29	1981-05-13	Imidazoazolalkensyreamider, nye mellomprodukter for deres fremstilling, deres fremstilling og deres anvendelse som legemiddel
NO854688A NO854688L (no)	1980-05-29	1985-11-22	Imidazoazolkarbonylforbindelser og deres anvendelse som mellomprodukter for fremstilling av legemidler

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO854688A NO854688L (no)	1980-05-29	1985-11-22	Imidazoazolkarbonylforbindelser og deres anvendelse som mellomprodukter for fremstilling av legemidler

Country Status (13)

Country	Link
US (1)	US4444770A (da)
EP (1)	EP0041215B1 (da)
AU (1)	AU543307B2 (da)
CA (1)	CA1188690A (da)
DE (1)	DE3173607D1 (da)
DK (1)	DK233281A (da)
ES (1)	ES8203897A1 (da)
FI (1)	FI70900C (da)
GR (1)	GR74557B (da)
HU (1)	HU186887B (da)
IL (1)	IL62960A (da)
NO (2)	NO811630L (da)
PT (1)	PT73058B (da)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3208437A1 (de) *	1982-03-09	1983-09-15	Bayer Ag, 5090 Leverkusen	Imidazothiadiazolalkencarbonsaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln
DE3329621A1 (de) *	1983-08-17	1985-02-28	Bayer Ag, 5090 Leverkusen	Aminoalkyl-imidazothiadiazol-alkencarbonsaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln
IT1213175B (it) *	1984-06-06	1989-12-14	Mediolanum Farmaceutici Srl	Derivati imidazotiazolmetilen-acetidrazidi, loro preparazione e composizioni farmaceutiche ad attivita'diuretica.
DE3542662A1 (de) *	1985-12-03	1987-06-04	Bayer Ag	Imidazothiadiazinalkensaeureamide, verfahren zu ihrer herstellung, zwischenprodukte zu ihrer herstellung und ihre verwendung zur behandlung von krankheiten
DE3542661A1 (de) *	1985-12-03	1987-06-04	Bayer Ag	Imidazopyridazinalkensaeureamide, verfahren zu ihrer herstellung, zwischenprodukte zu ihrer herstellung
TW438796B (en) *	1996-05-15	2001-06-07	Hoffmann La Roche	2,4-diaminopyrimidine derivatives, the manufacture process thereof, and the antibiotically-active pharmaceutical composition containing the same
WO2004111060A1 (en) *	2003-06-13	2004-12-23	Aegera Therapeutics Inc.	IMIDAZO[2,1-b]-1,3,4-THIADIAZOLE SULFOXIDES AND SULFONES
DE102005010215A1 (de) *	2005-03-05	2006-09-07	Bayer Cropscience Ag	Heterobicyclische Acrylamide
EP2193133B1 (en)	2007-09-27	2015-08-19	Fundación Centro Nacional de Investigaciones Oncológicas Carlos III	Imidazolothiadiazoles for use as protein kinase inhibitors
US8318928B2 (en) *	2008-12-15	2012-11-27	Glenmark Pharmaceuticals, S.A.	Fused imidazole carboxamides as TRPV3 modulators
ES2548571T3 (es)	2009-04-02	2015-10-19	Fundación Centro Nacional De Investigaciones Oncológicas Carlos Iii	Derivados de imidazo[2,1-b][1,3,4]tiadiazol
WO2011045646A1 (en) *	2009-10-13	2011-04-21	Council Of Scientific & Industrial Research	Imidazothiazole-chalcone derivatives as potential anticancer agents and process for the preparation thereof
MX2012005678A (es)	2009-11-16	2012-09-07	Univ California	Enhibidores de cinasas.
EP2855489B1 (en)	2012-04-26	2017-01-04	Bristol-Myers Squibb Company	Imidazothiadiazole and imidazopyridazine derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation
EA201491967A1 (ru)	2012-04-26	2015-03-31	Бристол-Майерс Сквибб Компани	Производные имидазотиадиазола в качестве ингибиторов активируемых протеазой рецепторов 4 (par4) для лечения агрегации тромбоцитов
SMT201700457T1 (it)	2012-04-26	2017-11-15	Bristol Myers Squibb Co	DERlVATI IMIDAZOTIADIAZOLICI E IMIDAZOPIRAZINICI COME INIBITORI DEL RECETTORE ATTIVATO DA PROTEASI 4 (PAR4) PER IL TRATTAMENTO DELL'AGGREGAZIONE PIASTRINICA
WO2018005591A1 (en)	2016-06-29	2018-01-04	Universite De Montreal	Biarylmethyl heterocycles
CA3158333A1 (en)	2019-10-21	2021-04-29	Novartis Ag	Compounds and compositions for the treatment of parasitic diseases

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3615639A (en) *	1967-10-23	1971-10-26	Eastman Kodak Co	Direct positive silver halide emulsions containing dyes as electron acceptors and spectral sensitizers
US3804823A (en) *	1972-02-15	1974-04-16	Eastman Kodak Co	Heterocyclic containing monoazo compounds
US4042583A (en) *	1973-09-20	1977-08-16	Pfizer Inc.	Imidazo[2,1-b]thiazole and thiazolo[3,2-a]-benzimidazole quaternary salts as hypoglycemic agents and growth promotants
OA04806A (fr) *	1973-12-10	1980-08-31	Bayer Ag	Nouveaux esters triazolothiazolyliques d'acide (thiono)-phosphorique (phosphonique), leur procédé de préparation et leur application comme insecticides et acaricides.
AT340414B (de) *	1975-02-18	1977-12-12	Plantex Ltd	Verfahren zur herstellung von neuen imidazo(2,1-b)thiazolderivaten und ihren salzen
US4263311A (en) *	1976-09-27	1981-04-21	Smithkline Corporation	5,6-Phenyl-2,3-dihydroimidazo [2,1-b] thiazoles
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
DE2902763A1 (de) *	1979-01-25	1980-08-07	Basf Ag	Basische farbstoffe

1981
- 1981-05-13 NO NO811630A patent/NO811630L/no unknown
- 1981-05-13 US US06/263,400 patent/US4444770A/en not_active Expired - Fee Related
- 1981-05-20 PT PT73058A patent/PT73058B/pt unknown
- 1981-05-21 AU AU70900/81A patent/AU543307B2/en not_active Ceased
- 1981-05-25 EP EP81104000A patent/EP0041215B1/de not_active Expired
- 1981-05-25 DE DE8181104000T patent/DE3173607D1/de not_active Expired
- 1981-05-26 IL IL62960A patent/IL62960A/xx unknown
- 1981-05-27 DK DK233281A patent/DK233281A/da not_active Application Discontinuation
- 1981-05-27 FI FI811630A patent/FI70900C/fi not_active IP Right Cessation
- 1981-05-27 CA CA000378454A patent/CA1188690A/en not_active Expired
- 1981-05-27 GR GR65080A patent/GR74557B/el unknown
- 1981-05-28 HU HU811597A patent/HU186887B/hu unknown
- 1981-05-28 ES ES502573A patent/ES8203897A1/es not_active Expired
1985
- 1985-11-22 NO NO854688A patent/NO854688L/no unknown

Also Published As

Publication number	Publication date
EP0041215B1 (de)	1986-01-29
FI811630L (fi)	1981-11-30
ES502573A0 (es)	1982-04-01
GR74557B (da)	1984-06-29
IL62960A (en)	1986-04-29
NO854688L (no)	1981-11-30
EP0041215A3 (en)	1982-04-14
DK233281A (da)	1981-11-30
AU543307B2 (en)	1985-04-18
FI70900B (fi)	1986-07-18
PT73058B (en)	1982-07-01
PT73058A (en)	1981-06-01
FI70900C (fi)	1986-10-27
IL62960A0 (en)	1981-07-31
HU186887B (en)	1985-10-28
CA1188690A (en)	1985-06-11
AU7090081A (en)	1981-12-03
EP0041215A2 (de)	1981-12-09
DE3173607D1 (en)	1986-03-13
US4444770A (en)	1984-04-24
ES8203897A1 (es)	1982-04-01

Publication	Publication Date	Title
DE69524114T2 (de)	2002-07-18	Naphthyridinonderivate
US4238492A (en)	1980-12-09	Phenoxyalkylcarboxylic acids
EP0041215B1 (de)	1986-01-29	Imidazoazolalkensäureamide, neue Zwischenprodukte zu ihrer Herstellung, ihre Herstellung und ihre Verwendung in Arzneimitteln
EP0173520B1 (en)	1990-01-03	Tricyclic oxindole antiinflammatory agents
JPH0253430B2 (da)	1990-11-16
JPH04247082A (ja)	1992-09-03	新スピロ〔４．５〕デカン化合物および医薬品組成物
IE48740B1 (en)	1985-05-01	N-(2-thiazolyl)amides and their use as anti-inflammatory and immunoregulatory agents
US4450159A (en)	1984-05-22	Carbamic acid derivatives as selective immunosuppresive agents
CZ294165B6 (cs)	2004-10-13	Farmaceutický prostředek obsahující @@oxobutanové kyseliny
US4054652A (en)	1977-10-18	Dihydro- and tetrahydro- iminothiazines
JPH0673012A (ja)	1994-03-15	４−イミノキノリン、その製法およびその使用
US4164579A (en)	1979-08-14	Hydroxythiazolidine-2-thiones
NO830611L (no)	1983-09-12	Imidazotiadiazolalkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendles i legemidler
IE46375B1 (en)	1983-05-18	3-imino-1,5,10,10a-tetrahydrothiazolo(3,4-b)isoquinoline derivatives
EP0055917B1 (en)	1984-11-21	New benzothiazine derivatives, processes for preparation thereof and use thereof
US4167571A (en)	1979-09-11	Thiazoline derivatives
EP0045602B1 (en)	1985-11-21	Novel polycyclic indole derivatives
US4801591A (en)	1989-01-31	2-alkenylene-thieno-1,2-thiazole derivatives with lipid-lowering activity
US4312869A (en)	1982-01-26	Monosubstituted piperazines
NO154840B (no)	1986-09-22	Analogifremgangsmaate til fremstilling av terapeutisk aktive substituerte 2-amino-3,4-dihydropyridinderivater.
JPH07309852A (ja)	1995-11-28	新規チアゾリジンジオン化合物
NO843108L (no)	1985-02-18	Aminoalkyl-imidazotiadiazol-alkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendelse i legemidler
GB2202532A (en)	1988-09-28	4-benzylthiophene(or furan)-2-sulfonamides as antiglaucoma agents
US3946019A (en)	1976-03-23	7H-Indolizino [5,6,7-IJ]isoquinoline derivatives
EP0094612A2 (en)	1983-11-23	Novel alkyloxazolylacetic acid derivative, processes for preparation and pharmaceutical compositions containing same