NO843108L - Aminoalkyl-imidazotiadiazol-alkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendelse i legemidler - Google Patents

Aminoalkyl-imidazotiadiazol-alkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendelse i legemidler

Info

Publication number: NO843108L
Authority: NO; Norway
Prior art keywords: alkyl; optionally; nitrogen; aryl; trifluoromethyl
Prior art date: 1983-08-17

Application number

NO843108A

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.)

1983-08-17

Filing date

1984-08-02

Publication date

1985-02-18

1984-08-02 Application filed by Bayer Ag filed Critical Bayer Ag

1985-02-18 Publication of NO843108L publication Critical patent/NO843108L/no

Links

238000002360 preparation method Methods 0.000 title claims description 15
239000003814 drug Substances 0.000 title description 5
239000000543 intermediate Substances 0.000 title description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 92
125000000217 alkyl group Chemical group 0.000 claims description 90
229910052757 nitrogen Inorganic materials 0.000 claims description 58
125000003118 aryl group Chemical group 0.000 claims description 46
229910052739 hydrogen Inorganic materials 0.000 claims description 44
239000001257 hydrogen Substances 0.000 claims description 44
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 42
229910052736 halogen Inorganic materials 0.000 claims description 40
150000002367 halogens Chemical group 0.000 claims description 40
125000004432 carbon atom Chemical group C* 0.000 claims description 38
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 38
229910052717 sulfur Inorganic materials 0.000 claims description 36
125000003545 alkoxy group Chemical group 0.000 claims description 29
229910052760 oxygen Inorganic materials 0.000 claims description 29
125000003710 aryl alkyl group Chemical group 0.000 claims description 27
229920006395 saturated elastomer Polymers 0.000 claims description 27
125000005842 heteroatom Chemical group 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 24
239000001301 oxygen Substances 0.000 claims description 24
125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
238000000034 method Methods 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
239000011593 sulfur Substances 0.000 claims description 21
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
150000001408 amides Chemical class 0.000 claims description 11
150000001728 carbonyl compounds Chemical class 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000004663 dialkyl amino group Chemical group 0.000 claims description 9
125000002541 furyl group Chemical group 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
125000003373 pyrazinyl group Chemical group 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 9
125000001544 thienyl group Chemical group 0.000 claims description 9
229910052799 carbon Chemical group 0.000 claims description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 5
239000002934 diuretic Substances 0.000 claims description 5
125000005956 isoquinolyl group Chemical group 0.000 claims description 5
125000005493 quinolyl group Chemical group 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
230000003424 uricosuric effect Effects 0.000 claims description 5
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 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
150000003869 acetamides Chemical class 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
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
125000005265 dialkylamine group Chemical group 0.000 claims description 3
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
229940116731 Uricosuric agent Drugs 0.000 claims description 2
230000003276 anti-hypertensive effect Effects 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims 6
230000002686 anti-diuretic effect Effects 0.000 claims 1
229940124538 antidiuretic agent Drugs 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
230000007935 neutral effect Effects 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
239000000725 suspension Substances 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
241000700159 Rattus Species 0.000 description 7
-1 phenyl- Chemical group 0.000 description 7
239000000126 substance Substances 0.000 description 7
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
239000002585 base Substances 0.000 description 6
239000000203 mixture 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
150000007513 acids Chemical class 0.000 description 5
230000001882 diuretic effect Effects 0.000 description 5
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 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
239000003795 chemical substances by application Substances 0.000 description 4
229960003531 phenolsulfonphthalein Drugs 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
BOXRDDIXJOUZLV-UHFFFAOYSA-N 2h-imidazo[4,5-d]thiadiazole Chemical class N1SC2=NC=NC2=N1 BOXRDDIXJOUZLV-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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
241000282472 Canis lupus familiaris Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
208000004880 Polyuria Diseases 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
230000029142 excretion Effects 0.000 description 3
238000009472 formulation Methods 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000000894 saliuretic effect Effects 0.000 description 3
210000002700 urine Anatomy 0.000 description 3
ARVAEGFCONISNP-UHFFFAOYSA-N 2-(diethylaminomethyl)-6-phenylimidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde Chemical compound N1=C2SC(CN(CC)CC)=NN2C(C=O)=C1C1=CC=CC=C1 ARVAEGFCONISNP-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
230000008033 biological extinction Effects 0.000 description 2
150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
238000001816 cooling Methods 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
229940030606 diuretics Drugs 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
229910052740 iodine Inorganic materials 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000010992 reflux Methods 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
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000005303 weighing Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
208000009304 Acute Kidney Injury Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000723345 Chrysophyllum Species 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-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
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
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
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons 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
230000004071 biological effect Effects 0.000 description 1
230000036765 blood level Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
239000011575 calcium Substances 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
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
150000001805 chlorine compounds Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000008151 electrolyte solution Substances 0.000 description 1
239000003995 emulsifying agent 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
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000001802 infusion Methods 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
230000014759 maintenance of location Effects 0.000 description 1
238000002483 medication Methods 0.000 description 1
239000000155 melt Substances 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
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus 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
231100000614 poison Toxicity 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
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000028327 secretion Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 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
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000005106 triarylsilyl group Chemical group 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 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
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- 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

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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)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO843108A 1983-08-17 1984-08-02 Aminoalkyl-imidazotiadiazol-alkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendelse i legemidler NO843108L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3329621A DE3329621A1 (de)	1983-08-17	1983-08-17	Aminoalkyl-imidazothiadiazol-alkencarbonsaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln

Publications (1)

Publication Number	Publication Date
NO843108L true NO843108L (no)	1985-02-18

Family

ID=6206712

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO843108A NO843108L (no)	1983-08-17	1984-08-02	Aminoalkyl-imidazotiadiazol-alkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendelse i legemidler

Country Status (16)

Country	Link
US (1)	US4588723A (fr)
EP (1)	EP0141072A3 (fr)
JP (1)	JPS6058989A (fr)
KR (1)	KR850001762A (fr)
AU (1)	AU3111184A (fr)
CA (1)	CA1234113A (fr)
DE (1)	DE3329621A1 (fr)
DK (1)	DK394384A (fr)
ES (7)	ES535054A0 (fr)
FI (1)	FI843226A7 (fr)
GR (1)	GR80133B (fr)
HU (1)	HU190969B (fr)
IL (1)	IL72678A0 (fr)
NO (1)	NO843108L (fr)
PT (1)	PT79084B (fr)
ZA (1)	ZA846378B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3670080D1 (de) *	1985-12-23	1990-05-10	Zambeletti Spa L	Azacyclische verbindungen, verfahren zur ihrer herstellung und ihre verwendung als pharmazeutika.
DE102005010215A1 (de) *	2005-03-05	2006-09-07	Bayer Cropscience Ag	Heterobicyclische Acrylamide
EP2682395A1 (fr) *	2012-07-04	2014-01-08	Laboratorios Del. Dr. Esteve, S.A.	Dérivés d'imidazo[2,1-b]thiazole, leur préparation et leur utilisation comme médicaments

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NO811630L (no) *	1980-05-29	1981-11-30	Bayer Ag	Imidazoazolalkensyreamider, nye mellomprodukter for deres fremstilling, deres fremstilling og deres anvendelse som legemiddel

1983
- 1983-08-17 DE DE3329621A patent/DE3329621A1/de not_active Withdrawn
1984
- 1984-07-24 AU AU31111/84A patent/AU3111184A/en not_active Abandoned
- 1984-07-26 US US06/634,851 patent/US4588723A/en not_active Expired - Fee Related
- 1984-08-02 NO NO843108A patent/NO843108L/no unknown
- 1984-08-06 EP EP84109291A patent/EP0141072A3/fr not_active Withdrawn
- 1984-08-10 ES ES535054A patent/ES535054A0/es active Granted
- 1984-08-14 PT PT79084A patent/PT79084B/pt unknown
- 1984-08-14 IL IL72678A patent/IL72678A0/xx unknown
- 1984-08-15 CA CA000461031A patent/CA1234113A/fr not_active Expired
- 1984-08-15 FI FI843226A patent/FI843226A7/fi not_active Application Discontinuation
- 1984-08-16 HU HU843114A patent/HU190969B/hu unknown
- 1984-08-16 ZA ZA846378A patent/ZA846378B/xx unknown
- 1984-08-16 KR KR1019840004913A patent/KR850001762A/ko not_active Withdrawn
- 1984-08-16 DK DK394384A patent/DK394384A/da not_active Application Discontinuation
- 1984-08-16 JP JP59170086A patent/JPS6058989A/ja active Pending
- 1984-08-17 GR GR80133A patent/GR80133B/el unknown
1985
- 1985-06-14 ES ES544220A patent/ES8604242A1/es not_active Expired
- 1985-06-14 ES ES544215A patent/ES8604237A1/es not_active Expired
- 1985-06-14 ES ES544219A patent/ES8604241A1/es not_active Expired
- 1985-06-14 ES ES544216A patent/ES8604238A1/es not_active Expired
- 1985-06-14 ES ES544217A patent/ES8604239A1/es not_active Expired
- 1985-06-14 ES ES544218A patent/ES8604240A1/es not_active Expired

Also Published As

Publication number	Publication date
GR80133B (en)	1984-12-19
DK394384D0 (da)	1984-08-16
ES544218A0 (es)	1986-01-16
ES8604237A1 (es)	1986-01-16
ES8600768A1 (es)	1985-10-16
ES8604242A1 (es)	1986-01-16
HUT36130A (en)	1985-08-28
AU3111184A (en)	1985-02-21
HU190969B (en)	1986-12-28
PT79084A (en)	1984-09-01
PT79084B (en)	1986-08-14
ES535054A0 (es)	1985-10-16
FI843226A7 (fi)	1985-02-18
IL72678A0 (en)	1984-11-30
ZA846378B (en)	1985-05-29
EP0141072A3 (fr)	1986-01-08
ES544216A0 (es)	1986-01-16
ES544215A0 (es)	1986-01-16
ES544217A0 (es)	1986-01-16
FI843226A0 (fi)	1984-08-15
ES8604239A1 (es)	1986-01-16
US4588723A (en)	1986-05-13
EP0141072A2 (fr)	1985-05-15
DK394384A (da)	1985-02-18
ES8604241A1 (es)	1986-01-16
ES544219A0 (es)	1986-01-16
CA1234113A (fr)	1988-03-15
ES544220A0 (es)	1986-01-16
DE3329621A1 (de)	1985-02-28
ES8604240A1 (es)	1986-01-16
KR850001762A (ko)	1985-04-01
ES8604238A1 (es)	1986-01-16
JPS6058989A (ja)	1985-04-05

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NO140424B (no)	1979-05-21	Analogifremgangsmaate for fremstilling av farmakologisk aktive indolderivater
EP2432776A1 (fr)	2012-03-28	Méthylsulfanylpyrimidines utiles en tant qu'agents anti-inflammatoires, analgésiques, et anti-épileptiques
NO162965B (no)	1989-12-04	Analogifremgangsmaate for fremstilling av terapeutisk aktive alfa-(2-okso-2,4,5,6,7,7a-heksahydrotieno-(3,2-c)-5-pyridyl)-fenyl-eddiksyre-derivater.
HU213113B (en)	1997-02-28	Process for producing 2-aminobenzoxazole and 2-amino-benzothiazole derivatives and pharmaceutical compositions containing them
UA58589C2 (uk)	2003-08-15	Тієнілазолілалкоксіетанаміни, спосіб їх одержання, проміжні продукти для їх одержання та фармацевтична композиція
JPS6253504B2 (fr)	1987-11-10
NO811630L (no)	1981-11-30	Imidazoazolalkensyreamider, nye mellomprodukter for deres fremstilling, deres fremstilling og deres anvendelse som legemiddel
DK149024B (da)	1985-12-23	Analogifremgangsmaade til fremstilling af krystallinske vandoploeselige salte af n-(2-pyridyl)-2-methyl-4-hydroxy-2h-1,2-benzothiazin-3-carboxamid-1,1-dioxid
JP2010095550A (ja)	2010-04-30	キノリン誘導体
US4086353A (en)	1978-04-25	Certain azolinylamino (azolidinylimino) indazoles
US4087526A (en)	1978-05-02	(3-Amino-5-substituted-6-fluoropyrazinoyl or pyrazamido)-guanidines and their derivatives bearing substituents on the guanidino nitrogens
NL8303311A (nl)	1984-04-16	Piperazinederivaten met anti-cholinergische en/of anti-histamineactiviteit.
NO161678B (no)	1989-06-05	Analogifremgangsmaate for fremstilling av metylendifosfonsyrederivater med antireumatiske egenskaper.
US6800623B2 (en)	2004-10-05	Method of treating schizophrenia
CS203135B2 (en)	1981-02-27	Method of producing racemic or optically active pyrimido/1,2a/heterocyclic compounds
NO137387B (no)	1977-11-14	Analogifremgangsm}te til fremstilling av 5-metyltiopyrimidiner med terapeutisk virkning
US4521619A (en)	1985-06-04	Therapeutically useful sulphur-containing benzylidene derivatives
US3787419A (en)	1974-01-22	N-substituted-alpha,alpha,alpha-trifluoro-m-toluamides
PL128998B1 (en)	1984-03-31	Process for preparing novel 2-amino-3-benzoylphenylacetamides and their derivatives
CS217979B2 (en)	1983-02-25	Method of making the cycloalcanonoximether
US4588723A (en)	1986-05-13	Aminoalkyl-imidazothiadiazole-alkenecarboxylic acid amides, intermediates for their preparation and their use in medicaments
NO830611L (no)	1983-09-12	Imidazotiadiazolalkenkarboksylsyreamider, nye mellomprodukter til deres fremstilling, deres fremstilling og deres anvendles i legemidler
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
NO761537L (fr)	1976-11-15
KR20000029564A (ko)	2000-05-25	5ＨＴ2ｃ길항제및Ｄ2길항제를함유하는약제학적조성물