DE2230675A1 - Diuretisches und antihypertensives mittel - Google Patents
Diuretisches und antihypertensives mittelInfo
- Publication number
- DE2230675A1 DE2230675A1 DE2230675A DE2230675A DE2230675A1 DE 2230675 A1 DE2230675 A1 DE 2230675A1 DE 2230675 A DE2230675 A DE 2230675A DE 2230675 A DE2230675 A DE 2230675A DE 2230675 A1 DE2230675 A1 DE 2230675A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- pyrazolone
- ethanol
- ethyl ester
- acid ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000002934 diuretic Substances 0.000 title claims description 10
- 230000001882 diuretic effect Effects 0.000 title claims description 8
- 239000002220 antihypertensive agent Substances 0.000 title claims description 6
- 229940030600 antihypertensive agent Drugs 0.000 title claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims 1
- 125000005521 carbonamide group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 176
- -1 phenanthrenyl radical Chemical class 0.000 description 69
- 235000019441 ethanol Nutrition 0.000 description 66
- 239000000243 solution Substances 0.000 description 36
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- XLTPBSBNLKQLHB-UHFFFAOYSA-N ethyl 3-amino-3-ethoxyprop-2-enoate Chemical compound CCOC(N)=CC(=O)OCC XLTPBSBNLKQLHB-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- 239000013078 crystal Substances 0.000 description 17
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 230000029142 excretion Effects 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 241000700159 Rattus Species 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 235000015424 sodium Nutrition 0.000 description 6
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 125000004494 ethyl ester group Chemical group 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
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 230000000894 saliuretic effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 210000002700 urine Anatomy 0.000 description 4
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-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
- 239000012670 alkaline solution Substances 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- BUKHSQBUKZIMLB-UHFFFAOYSA-L potassium;sodium;dichloride Chemical compound [Na+].[Cl-].[Cl-].[K+] BUKHSQBUKZIMLB-UHFFFAOYSA-L 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 3
- 239000003826 tablet 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
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229940030606 diuretics Drugs 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 238000003304 gavage Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000004526 pharmaceutical effect Effects 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YXLOOEQTKMDKRW-UHFFFAOYSA-N (2,3-dichlorophenyl)methylhydrazine Chemical compound NNCC1=CC=CC(Cl)=C1Cl YXLOOEQTKMDKRW-UHFFFAOYSA-N 0.000 description 1
- QSARTMGKCJEEOA-UHFFFAOYSA-N (2,4,5-trichlorophenyl)methylhydrazine Chemical compound NNCC1=CC(Cl)=C(Cl)C=C1Cl QSARTMGKCJEEOA-UHFFFAOYSA-N 0.000 description 1
- MOXMLBBLTBHKOW-UHFFFAOYSA-N (2,4-dichlorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Cl)C=C1Cl MOXMLBBLTBHKOW-UHFFFAOYSA-N 0.000 description 1
- QKUSRPMMOKELAO-UHFFFAOYSA-N (2,4-dimethylphenyl)methylhydrazine Chemical compound CC1=CC=C(CNN)C(C)=C1 QKUSRPMMOKELAO-UHFFFAOYSA-N 0.000 description 1
- JAQZKBKDMHKOBT-UHFFFAOYSA-N (2,5-dichlorophenyl)methylhydrazine Chemical compound NNCC1=CC(Cl)=CC=C1Cl JAQZKBKDMHKOBT-UHFFFAOYSA-N 0.000 description 1
- KJOOVLJGVFOGOL-UHFFFAOYSA-N (2,5-dimethylphenyl)methylhydrazine Chemical compound CC1=CC=C(C)C(CNN)=C1 KJOOVLJGVFOGOL-UHFFFAOYSA-N 0.000 description 1
- FUJFXSUHLRUWEC-UHFFFAOYSA-N (2,6-dichlorophenyl)methylhydrazine Chemical compound NNCC1=C(Cl)C=CC=C1Cl FUJFXSUHLRUWEC-UHFFFAOYSA-N 0.000 description 1
- OHOLTPDWHLBTJD-UHFFFAOYSA-N (2-bromophenyl)methylhydrazine Chemical compound NNCC1=CC=CC=C1Br OHOLTPDWHLBTJD-UHFFFAOYSA-N 0.000 description 1
- BMCMWXOVSVJGOR-UHFFFAOYSA-N (2-chlorophenyl)methylhydrazine Chemical compound NNCC1=CC=CC=C1Cl BMCMWXOVSVJGOR-UHFFFAOYSA-N 0.000 description 1
- OOMBRKGIWITBLL-UHFFFAOYSA-N (2-fluorophenyl)methylhydrazine Chemical compound NNCC1=CC=CC=C1F OOMBRKGIWITBLL-UHFFFAOYSA-N 0.000 description 1
- IXRQTCDPQZMNSN-UHFFFAOYSA-N (2-methylphenyl)methylhydrazine Chemical compound CC1=CC=CC=C1CNN IXRQTCDPQZMNSN-UHFFFAOYSA-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
- OMBMILBFFMGAJD-UHFFFAOYSA-N (3,4-dichlorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Cl)C(Cl)=C1 OMBMILBFFMGAJD-UHFFFAOYSA-N 0.000 description 1
- YKYYWSASOAPYST-UHFFFAOYSA-N (3,4-dimethylphenyl)methylhydrazine Chemical compound CC1=CC=C(CNN)C=C1C YKYYWSASOAPYST-UHFFFAOYSA-N 0.000 description 1
- DLPOEUZVERZKMO-UHFFFAOYSA-N (3,5-dichlorophenyl)methylhydrazine Chemical compound NNCC1=CC(Cl)=CC(Cl)=C1 DLPOEUZVERZKMO-UHFFFAOYSA-N 0.000 description 1
- ZUFKJOBIQWYVSA-UHFFFAOYSA-N (3-bromo-4-chlorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Cl)C(Br)=C1 ZUFKJOBIQWYVSA-UHFFFAOYSA-N 0.000 description 1
- VUJAAGDKMIUIFQ-UHFFFAOYSA-N (3-bromophenyl)methylhydrazine Chemical compound NNCC1=CC=CC(Br)=C1 VUJAAGDKMIUIFQ-UHFFFAOYSA-N 0.000 description 1
- VOCCPRCLJDTWEH-UHFFFAOYSA-N (3-chloro-4-methylphenyl)methylhydrazine Chemical compound CC1=CC=C(CNN)C=C1Cl VOCCPRCLJDTWEH-UHFFFAOYSA-N 0.000 description 1
- LZWGHTUFBHAOHN-UHFFFAOYSA-N (3-chlorophenyl)methylhydrazine Chemical compound NNCC1=CC=CC(Cl)=C1 LZWGHTUFBHAOHN-UHFFFAOYSA-N 0.000 description 1
- SAVAJKHGIQLPDD-UHFFFAOYSA-N (3-fluorophenyl)methylhydrazine Chemical compound NNCC1=CC=CC(F)=C1 SAVAJKHGIQLPDD-UHFFFAOYSA-N 0.000 description 1
- PUAGXICSGKDMTF-UHFFFAOYSA-N (3-iodophenyl)methylhydrazine Chemical compound NNCC1=CC=CC(I)=C1 PUAGXICSGKDMTF-UHFFFAOYSA-N 0.000 description 1
- LRDZBVAFUXSPGH-UHFFFAOYSA-N (3-methylphenyl)methylhydrazine Chemical compound CC1=CC=CC(CNN)=C1 LRDZBVAFUXSPGH-UHFFFAOYSA-N 0.000 description 1
- UVLKAHYGKLRXON-UHFFFAOYSA-N (3-nitrophenyl)methylhydrazine Chemical compound NNCC1=CC=CC([N+]([O-])=O)=C1 UVLKAHYGKLRXON-UHFFFAOYSA-N 0.000 description 1
- KWZJFFIYJILLRX-UHFFFAOYSA-N (4-bromo-3-chlorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Br)C(Cl)=C1 KWZJFFIYJILLRX-UHFFFAOYSA-N 0.000 description 1
- SABLROJJEJTWTE-UHFFFAOYSA-N (4-bromophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Br)C=C1 SABLROJJEJTWTE-UHFFFAOYSA-N 0.000 description 1
- TYDHJVQGBWGEPT-UHFFFAOYSA-N (4-chloro-3-methylphenyl)methylhydrazine Chemical compound CC1=CC(CNN)=CC=C1Cl TYDHJVQGBWGEPT-UHFFFAOYSA-N 0.000 description 1
- OEMUGKBHGOCMKZ-UHFFFAOYSA-N (4-chlorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Cl)C=C1 OEMUGKBHGOCMKZ-UHFFFAOYSA-N 0.000 description 1
- YMMCBGIHBVKZGD-UHFFFAOYSA-N (4-fluorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(F)C=C1 YMMCBGIHBVKZGD-UHFFFAOYSA-N 0.000 description 1
- AQURFXLIZXOCLU-UHFFFAOYSA-N (4-methoxyphenyl)methylhydrazine Chemical compound COC1=CC=C(CNN)C=C1 AQURFXLIZXOCLU-UHFFFAOYSA-N 0.000 description 1
- XPBBLOVWHBLPMK-UHFFFAOYSA-N (4-methylphenyl)methylhydrazine Chemical compound CC1=CC=C(CNN)C=C1 XPBBLOVWHBLPMK-UHFFFAOYSA-N 0.000 description 1
- XUPNPQDJSZKHLN-UHFFFAOYSA-N (4-nitrophenyl)methylhydrazine Chemical compound NNCC1=CC=C([N+]([O-])=O)C=C1 XUPNPQDJSZKHLN-UHFFFAOYSA-N 0.000 description 1
- GCDLQAOATMBBDF-UHFFFAOYSA-N (4-phenylphenyl)methylhydrazine Chemical compound C1=CC(CNN)=CC=C1C1=CC=CC=C1 GCDLQAOATMBBDF-UHFFFAOYSA-N 0.000 description 1
- XVIBUTVRALYGDZ-UHFFFAOYSA-N (5-chloro-2-fluorophenyl)methylhydrazine Chemical compound NNCC1=CC(Cl)=CC=C1F XVIBUTVRALYGDZ-UHFFFAOYSA-N 0.000 description 1
- SNBIXINOMWMLIV-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethylhydrazine Chemical compound NNCC1=CC=C2OCOC2=C1 SNBIXINOMWMLIV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OEXAUCHTSVKKAO-UHFFFAOYSA-N 1-benzyl-1-butylhydrazine Chemical compound CCCCN(N)CC1=CC=CC=C1 OEXAUCHTSVKKAO-UHFFFAOYSA-N 0.000 description 1
- 125000006184 2,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-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
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006188 2-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006185 3,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006186 3,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C([H])=C1C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006506 3-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
- 125000006500 3-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC(F)(F)F)=C1[H])C([H])([H])* 0.000 description 1
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 1
- IFFKJNUVHWQCCD-UHFFFAOYSA-N 4-(hydrazinylmethyl)benzonitrile Chemical compound NNCC1=CC=C(C#N)C=C1 IFFKJNUVHWQCCD-UHFFFAOYSA-N 0.000 description 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 125000002528 4-isopropyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006491 4-t-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000173 4-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC(F)(F)F)C([H])([H])* 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000009304 Acute Kidney Injury Diseases 0.000 description 1
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- 208000010201 Exanthema Diseases 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 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
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 208000033626 Renal failure acute Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 201000011040 acute kidney failure Diseases 0.000 description 1
- 208000012998 acute renal failure Diseases 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 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
- 125000004414 alkyl thio 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
- 150000001411 amidrazones Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 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
- 239000003085 diluting agent Substances 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002497 edematous effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005048 flame photometry Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000011010 flushing procedure Methods 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
- 229960002442 glucosamine Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 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
- 210000003097 mucus Anatomy 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006187 pill 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
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 239000008117 stearic acid Substances 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2230675A DE2230675A1 (de) | 1972-06-23 | 1972-06-23 | Diuretisches und antihypertensives mittel |
| LU67748A LU67748A1 (enExample) | 1972-06-23 | 1973-06-06 | |
| IL42562A IL42562A (en) | 1972-06-23 | 1973-06-20 | Pharmaceutical compositions containing 3-amino-pyrazol-5-ones |
| NL7308648A NL7308648A (enExample) | 1972-06-23 | 1973-06-21 | |
| AU57200/73A AU478762B2 (en) | 1973-06-21 | Medicinal use of pyrazolone derivatives | |
| BE132532A BE801227A (fr) | 1972-06-23 | 1973-06-21 | Nouveau medicament diuretique et anti-hypertensif |
| IE1036/73A IE37835B1 (en) | 1972-06-23 | 1973-06-22 | Medicinal use of pyrazolone derivatives |
| ZA734240A ZA734240B (en) | 1972-06-23 | 1973-06-22 | Medicinal use of pyrazolone derivatives |
| FR7322954A FR2189071B1 (enExample) | 1972-06-23 | 1973-06-22 | |
| GB2978673A GB1391052A (en) | 1972-06-23 | 1973-06-22 | Medicinal use of pyrazolone derivatives |
| US05/515,448 US3950528A (en) | 1972-06-23 | 1974-10-17 | 1-Substituted-3-amino-pyrazol-5-ones |
| US05/637,861 US4061653A (en) | 1972-06-23 | 1975-12-04 | 1-Substituted-3-amino-pyrazol-5-ones |
| US05/756,179 US4076943A (en) | 1972-06-23 | 1977-01-03 | 1-Substituted-3-amino-pyrazol-5-ones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2230675A DE2230675A1 (de) | 1972-06-23 | 1972-06-23 | Diuretisches und antihypertensives mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2230675A1 true DE2230675A1 (de) | 1974-01-10 |
Family
ID=5848526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2230675A Withdrawn DE2230675A1 (de) | 1972-06-23 | 1972-06-23 | Diuretisches und antihypertensives mittel |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE801227A (enExample) |
| DE (1) | DE2230675A1 (enExample) |
| FR (1) | FR2189071B1 (enExample) |
| GB (1) | GB1391052A (enExample) |
| IE (1) | IE37835B1 (enExample) |
| IL (1) | IL42562A (enExample) |
| LU (1) | LU67748A1 (enExample) |
| NL (1) | NL7308648A (enExample) |
| ZA (1) | ZA734240B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4081596A (en) * | 1973-04-17 | 1978-03-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| USRE30420E (en) * | 1973-04-17 | 1980-10-21 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4288446A (en) * | 1973-04-17 | 1981-09-08 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
-
1972
- 1972-06-23 DE DE2230675A patent/DE2230675A1/de not_active Withdrawn
-
1973
- 1973-06-06 LU LU67748A patent/LU67748A1/xx unknown
- 1973-06-20 IL IL42562A patent/IL42562A/en unknown
- 1973-06-21 NL NL7308648A patent/NL7308648A/xx unknown
- 1973-06-21 BE BE132532A patent/BE801227A/xx unknown
- 1973-06-22 FR FR7322954A patent/FR2189071B1/fr not_active Expired
- 1973-06-22 GB GB2978673A patent/GB1391052A/en not_active Expired
- 1973-06-22 IE IE1036/73A patent/IE37835B1/xx unknown
- 1973-06-22 ZA ZA734240A patent/ZA734240B/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4081596A (en) * | 1973-04-17 | 1978-03-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| USRE30420E (en) * | 1973-04-17 | 1980-10-21 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4288446A (en) * | 1973-04-17 | 1981-09-08 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
Also Published As
| Publication number | Publication date |
|---|---|
| IE37835B1 (en) | 1977-10-26 |
| FR2189071A1 (enExample) | 1974-01-25 |
| NL7308648A (enExample) | 1973-12-27 |
| GB1391052A (en) | 1975-04-16 |
| FR2189071B1 (enExample) | 1977-09-09 |
| AU5720073A (en) | 1975-01-09 |
| IL42562A (en) | 1977-05-31 |
| BE801227A (fr) | 1973-12-21 |
| IE37835L (en) | 1973-12-23 |
| ZA734240B (en) | 1974-05-29 |
| IL42562A0 (en) | 1973-08-29 |
| LU67748A1 (enExample) | 1973-08-16 |
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