DE2230792A1 - 3-amino-pyrazolone-(5), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel - Google Patents
3-amino-pyrazolone-(5), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittelInfo
- Publication number
- DE2230792A1 DE2230792A1 DE2230792A DE2230792A DE2230792A1 DE 2230792 A1 DE2230792 A1 DE 2230792A1 DE 2230792 A DE2230792 A DE 2230792A DE 2230792 A DE2230792 A DE 2230792A DE 2230792 A1 DE2230792 A1 DE 2230792A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- radical
- substituted
- pyrazolone
- alkyl
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 229940126601 medicinal product Drugs 0.000 title 1
- -1 Carbonamido Chemical group 0.000 claims description 47
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 150000001411 amidrazones Chemical class 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000002934 diuretic Substances 0.000 claims description 5
- 230000001882 diuretic effect Effects 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 239000002220 antihypertensive agent Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000002429 hydrazines Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229940030600 antihypertensive agent Drugs 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 179
- 235000019441 ethanol Nutrition 0.000 description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 36
- XLTPBSBNLKQLHB-UHFFFAOYSA-N ethyl 3-amino-3-ethoxyprop-2-enoate Chemical compound CCOC(N)=CC(=O)OCC XLTPBSBNLKQLHB-UHFFFAOYSA-N 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 241000700159 Rattus Species 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 230000029142 excretion Effects 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 238000006243 chemical reaction Methods 0.000 description 8
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 235000015424 sodium Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YTLYLLTVENPWFT-UHFFFAOYSA-N 3-aminoprop-2-enoic acid Chemical class NC=CC(O)=O YTLYLLTVENPWFT-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000000894 saliuretic effect Effects 0.000 description 4
- 210000002700 urine Anatomy 0.000 description 4
- SABLROJJEJTWTE-UHFFFAOYSA-N (4-bromophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Br)C=C1 SABLROJJEJTWTE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000004526 pharmaceutical effect Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- 239000007858 starting material Substances 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
- QSARTMGKCJEEOA-UHFFFAOYSA-N (2,4,5-trichlorophenyl)methylhydrazine Chemical compound NNCC1=CC(Cl)=C(Cl)C=C1Cl QSARTMGKCJEEOA-UHFFFAOYSA-N 0.000 description 2
- QKUSRPMMOKELAO-UHFFFAOYSA-N (2,4-dimethylphenyl)methylhydrazine Chemical compound CC1=CC=C(CNN)C(C)=C1 QKUSRPMMOKELAO-UHFFFAOYSA-N 0.000 description 2
- KJOOVLJGVFOGOL-UHFFFAOYSA-N (2,5-dimethylphenyl)methylhydrazine Chemical compound CC1=CC=C(C)C(CNN)=C1 KJOOVLJGVFOGOL-UHFFFAOYSA-N 0.000 description 2
- OHOLTPDWHLBTJD-UHFFFAOYSA-N (2-bromophenyl)methylhydrazine Chemical compound NNCC1=CC=CC=C1Br OHOLTPDWHLBTJD-UHFFFAOYSA-N 0.000 description 2
- MYNJXMGVVBFZHF-UHFFFAOYSA-N (2-chloro-4-fluorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(F)C=C1Cl MYNJXMGVVBFZHF-UHFFFAOYSA-N 0.000 description 2
- IXRQTCDPQZMNSN-UHFFFAOYSA-N (2-methylphenyl)methylhydrazine Chemical compound CC1=CC=CC=C1CNN IXRQTCDPQZMNSN-UHFFFAOYSA-N 0.000 description 2
- YKYYWSASOAPYST-UHFFFAOYSA-N (3,4-dimethylphenyl)methylhydrazine Chemical compound CC1=CC=C(CNN)C=C1C YKYYWSASOAPYST-UHFFFAOYSA-N 0.000 description 2
- ZUFKJOBIQWYVSA-UHFFFAOYSA-N (3-bromo-4-chlorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Cl)C(Br)=C1 ZUFKJOBIQWYVSA-UHFFFAOYSA-N 0.000 description 2
- VUJAAGDKMIUIFQ-UHFFFAOYSA-N (3-bromophenyl)methylhydrazine Chemical compound NNCC1=CC=CC(Br)=C1 VUJAAGDKMIUIFQ-UHFFFAOYSA-N 0.000 description 2
- VOCCPRCLJDTWEH-UHFFFAOYSA-N (3-chloro-4-methylphenyl)methylhydrazine Chemical compound CC1=CC=C(CNN)C=C1Cl VOCCPRCLJDTWEH-UHFFFAOYSA-N 0.000 description 2
- PUAGXICSGKDMTF-UHFFFAOYSA-N (3-iodophenyl)methylhydrazine Chemical compound NNCC1=CC=CC(I)=C1 PUAGXICSGKDMTF-UHFFFAOYSA-N 0.000 description 2
- LRDZBVAFUXSPGH-UHFFFAOYSA-N (3-methylphenyl)methylhydrazine Chemical compound CC1=CC=CC(CNN)=C1 LRDZBVAFUXSPGH-UHFFFAOYSA-N 0.000 description 2
- UVLKAHYGKLRXON-UHFFFAOYSA-N (3-nitrophenyl)methylhydrazine Chemical compound NNCC1=CC=CC([N+]([O-])=O)=C1 UVLKAHYGKLRXON-UHFFFAOYSA-N 0.000 description 2
- KWZJFFIYJILLRX-UHFFFAOYSA-N (4-bromo-3-chlorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Br)C(Cl)=C1 KWZJFFIYJILLRX-UHFFFAOYSA-N 0.000 description 2
- HNSMCIGVJAAADX-UHFFFAOYSA-N (4-chloro-3-methoxyphenyl)methylhydrazine Chemical compound COC1=CC(CNN)=CC=C1Cl HNSMCIGVJAAADX-UHFFFAOYSA-N 0.000 description 2
- TYDHJVQGBWGEPT-UHFFFAOYSA-N (4-chloro-3-methylphenyl)methylhydrazine Chemical compound CC1=CC(CNN)=CC=C1Cl TYDHJVQGBWGEPT-UHFFFAOYSA-N 0.000 description 2
- JRBYEYSVCBDBQO-UHFFFAOYSA-N (4-iodophenyl)methylhydrazine Chemical compound NNCC1=CC=C(I)C=C1 JRBYEYSVCBDBQO-UHFFFAOYSA-N 0.000 description 2
- XPBBLOVWHBLPMK-UHFFFAOYSA-N (4-methylphenyl)methylhydrazine Chemical compound CC1=CC=C(CNN)C=C1 XPBBLOVWHBLPMK-UHFFFAOYSA-N 0.000 description 2
- XUPNPQDJSZKHLN-UHFFFAOYSA-N (4-nitrophenyl)methylhydrazine Chemical compound NNCC1=CC=C([N+]([O-])=O)C=C1 XUPNPQDJSZKHLN-UHFFFAOYSA-N 0.000 description 2
- GCDLQAOATMBBDF-UHFFFAOYSA-N (4-phenylphenyl)methylhydrazine Chemical compound C1=CC(CNN)=CC=C1C1=CC=CC=C1 GCDLQAOATMBBDF-UHFFFAOYSA-N 0.000 description 2
- HWYNHHNNZIWSAA-UHFFFAOYSA-N (4-propan-2-ylphenyl)methylhydrazine Chemical compound CC(C)C1=CC=C(CNN)C=C1 HWYNHHNNZIWSAA-UHFFFAOYSA-N 0.000 description 2
- DXWPGWVZIREAMJ-UHFFFAOYSA-N (8-chloronaphthalen-2-yl)methylhydrazine Chemical compound C1=CC=C(Cl)C2=CC(CNN)=CC=C21 DXWPGWVZIREAMJ-UHFFFAOYSA-N 0.000 description 2
- SNBIXINOMWMLIV-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethylhydrazine Chemical compound NNCC1=CC=C2OCOC2=C1 SNBIXINOMWMLIV-UHFFFAOYSA-N 0.000 description 2
- DIWDIDLCINRQFW-UHFFFAOYSA-N 2,3-dihydro-1h-inden-5-ylmethylhydrazine Chemical compound NNCC1=CC=C2CCCC2=C1 DIWDIDLCINRQFW-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 229920001615 Tragacanth Polymers 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
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- 238000002425 crystallisation Methods 0.000 description 2
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- 239000003085 diluting agent Substances 0.000 description 2
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- 238000003304 gavage Methods 0.000 description 2
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- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 210000003097 mucus Anatomy 0.000 description 2
- 150000007530 organic bases Chemical class 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 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
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- OOMBRKGIWITBLL-UHFFFAOYSA-N (2-fluorophenyl)methylhydrazine Chemical compound NNCC1=CC=CC=C1F OOMBRKGIWITBLL-UHFFFAOYSA-N 0.000 description 1
- FSPHMABFSTZECX-UHFFFAOYSA-N (2-nitrophenyl)methylhydrazine Chemical compound NNCC1=CC=CC=C1[N+]([O-])=O FSPHMABFSTZECX-UHFFFAOYSA-N 0.000 description 1
- VGVVXPMCVIYNOR-UHFFFAOYSA-N (2-phenylphenyl)methylhydrazine Chemical compound NNCC1=CC=CC=C1C1=CC=CC=C1 VGVVXPMCVIYNOR-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
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- 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)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (33)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2230792A DE2230792A1 (de) | 1972-06-23 | 1972-06-23 | 3-amino-pyrazolone-(5), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| RO7375048A RO71819A (ro) | 1972-06-23 | 1973-06-06 | Procedeu pentru prepararea de 3-amino-pirazolone-(5) |
| AU57051/73A AU478915B2 (en) | 1973-06-18 | 3-amino-pyrazolones-(5) processes for their manufacture and their use as medicines | |
| BG023919A BG22819A3 (bg) | 1972-06-23 | 1973-06-19 | Метод за получаване на 3--амино-пиразолони-(5) |
| NL7308575A NL7308575A (enrdf_load_stackoverflow) | 1972-06-23 | 1973-06-20 | |
| IL42560A IL42560A (en) | 1972-06-23 | 1973-06-20 | 1 - ethylmethyl - 3 - amino - pyrazole - 5 - helium and their salts and process for their production |
| CH897973A CH592632A5 (enrdf_load_stackoverflow) | 1972-06-23 | 1973-06-20 | |
| AT544673A AT323735B (de) | 1972-06-23 | 1973-06-20 | Verfahren zur herstellung von neuen 3-amino-pyrazolonen-(5) und ihren salzen |
| SE7308721A SE401181B (sv) | 1972-06-23 | 1973-06-20 | Sett att framstella nya 3-aminopyrazolon-(5)-er avsedda att anvendas som lekemedel |
| SU1938995A SU472503A3 (ru) | 1972-06-23 | 1973-06-20 | Способ получени производных 3аминопиразолона-5 |
| DD171728A DD109874A5 (enrdf_load_stackoverflow) | 1972-06-23 | 1973-06-21 | |
| LU67854A LU67854A1 (enrdf_load_stackoverflow) | 1972-06-23 | 1973-06-21 | |
| BE132533A BE801228A (fr) | 1972-06-23 | 1973-06-21 | Nouvelles 3-amino-pyrazolones-(5) leur procede de preparation et medicaments les contenant |
| EG235/73A EG11039A (en) | 1972-06-23 | 1973-06-21 | Method for preparation of 3-pyrazol-5-one bayer ag |
| JP48069262A JPS4962463A (enrdf_load_stackoverflow) | 1972-06-23 | 1973-06-21 | |
| DK349573A DK133468C (da) | 1972-06-23 | 1973-06-22 | Analogifremgangsmade til fremstilling af 1-benzyl-3-amino-pyrazoloner-(5). |
| ZA734244A ZA734244B (en) | 1972-06-23 | 1973-06-22 | 3-amino-pyrazol-5-ones,processes for their manufacture and their use as medicines |
| IE1035/73A IE37834B1 (en) | 1972-06-23 | 1973-06-22 | 3-amino-pyrazolones-(5),processes for their manufacture and their use as medicines |
| ES416167A ES416167A1 (es) | 1972-06-23 | 1973-06-22 | Procedimiento para la produccion de 3-amino-pirazolonas- (5). |
| NO2618/73A NO137196C (no) | 1972-06-23 | 1973-06-22 | Analogifremgangsm}te til fremstilling av terapeutisk aktive 1-benzyl-3-amino-pyrazoloner-(5) |
| PL1973163511A PL87665B1 (enrdf_load_stackoverflow) | 1972-06-23 | 1973-06-22 | |
| FR7322955A FR2189072B1 (enrdf_load_stackoverflow) | 1972-06-23 | 1973-06-22 | |
| AR248701A AR205329A1 (es) | 1972-06-23 | 1973-06-22 | Procedimiento para la produccion de nuevas o-aminopirazolonas-(5) |
| HUBA2942A HU168358B (enrdf_load_stackoverflow) | 1972-06-23 | 1973-06-22 | |
| OA54946A OA04432A (fr) | 1972-06-23 | 1973-06-22 | Procédé de préparation de 3-amino-pyrazolones-(5). |
| CA174,778A CA1017752A (en) | 1972-06-23 | 1973-06-22 | 1-substituted-3-amino-pyrazol-5-ones |
| GB2978573A GB1391051A (en) | 1972-06-23 | 1973-06-22 | 3-amino-pyrazolones-5, processes for their manufacture and their use as medicines |
| KR7301005A KR780000147B1 (en) | 1972-06-23 | 1973-06-23 | Processes for the manufacture of 3-amino-pyrazolones-(5) and their use as medicine |
| US05/515,448 US3950528A (en) | 1972-06-23 | 1974-10-17 | 1-Substituted-3-amino-pyrazol-5-ones |
| PH16674A PH11606A (en) | 1972-06-23 | 1975-01-03 | Method for treating oedematus,hypertonic conditions and acute renal failure using 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 |
| HK112/76*UA HK11276A (en) | 1972-06-23 | 1976-03-04 | 3-amino-pyrazolones-(5), processes for their manufacture and their use as medicines |
| 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 |
|---|---|---|---|
| DE2230792A DE2230792A1 (de) | 1972-06-23 | 1972-06-23 | 3-amino-pyrazolone-(5), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2230792A1 true DE2230792A1 (de) | 1974-01-17 |
Family
ID=5848604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2230792A Withdrawn DE2230792A1 (de) | 1972-06-23 | 1972-06-23 | 3-amino-pyrazolone-(5), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Country Status (29)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP0180707A1 (de) * | 1984-10-04 | 1986-05-14 | Bayer Ag | Verfahren zur Herstellung von Muzolimin |
-
1972
- 1972-06-23 DE DE2230792A patent/DE2230792A1/de not_active Withdrawn
-
1973
- 1973-06-06 RO RO7375048A patent/RO71819A/ro unknown
- 1973-06-19 BG BG023919A patent/BG22819A3/xx unknown
- 1973-06-20 NL NL7308575A patent/NL7308575A/xx not_active Application Discontinuation
- 1973-06-20 CH CH897973A patent/CH592632A5/xx not_active IP Right Cessation
- 1973-06-20 SU SU1938995A patent/SU472503A3/ru active
- 1973-06-20 IL IL42560A patent/IL42560A/en unknown
- 1973-06-20 AT AT544673A patent/AT323735B/de not_active IP Right Cessation
- 1973-06-20 SE SE7308721A patent/SE401181B/xx unknown
- 1973-06-21 DD DD171728A patent/DD109874A5/xx unknown
- 1973-06-21 LU LU67854A patent/LU67854A1/xx unknown
- 1973-06-21 JP JP48069262A patent/JPS4962463A/ja active Pending
- 1973-06-21 EG EG235/73A patent/EG11039A/xx active
- 1973-06-21 BE BE132533A patent/BE801228A/xx unknown
- 1973-06-22 CA CA174,778A patent/CA1017752A/en not_active Expired
- 1973-06-22 DK DK349573A patent/DK133468C/da active
- 1973-06-22 ZA ZA734244A patent/ZA734244B/xx unknown
- 1973-06-22 AR AR248701A patent/AR205329A1/es active
- 1973-06-22 HU HUBA2942A patent/HU168358B/hu unknown
- 1973-06-22 GB GB2978573A patent/GB1391051A/en not_active Expired
- 1973-06-22 PL PL1973163511A patent/PL87665B1/pl unknown
- 1973-06-22 FR FR7322955A patent/FR2189072B1/fr not_active Expired
- 1973-06-22 IE IE1035/73A patent/IE37834B1/xx unknown
- 1973-06-22 OA OA54946A patent/OA04432A/xx unknown
- 1973-06-22 NO NO2618/73A patent/NO137196C/no unknown
- 1973-06-22 ES ES416167A patent/ES416167A1/es not_active Expired
- 1973-06-23 KR KR7301005A patent/KR780000147B1/ko not_active Expired
-
1975
- 1975-01-03 PH PH16674A patent/PH11606A/en unknown
-
1976
- 1976-03-04 HK HK112/76*UA patent/HK11276A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP0180707A1 (de) * | 1984-10-04 | 1986-05-14 | Bayer Ag | Verfahren zur Herstellung von Muzolimin |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |