IL42562A - Pharmaceutical compositions containing 3-amino-pyrazol-5-ones - Google Patents
Pharmaceutical compositions containing 3-amino-pyrazol-5-onesInfo
- Publication number
- IL42562A IL42562A IL42562A IL4256273A IL42562A IL 42562 A IL42562 A IL 42562A IL 42562 A IL42562 A IL 42562A IL 4256273 A IL4256273 A IL 4256273A IL 42562 A IL42562 A IL 42562A
- Authority
- IL
- Israel
- Prior art keywords
- amino
- pyrazol
- compound
- active ingredient
- salt
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 24
- ACOIYJJFAXRSHM-UHFFFAOYSA-N 5-aminopyrazol-3-one Chemical class NC1=CC(=O)N=N1 ACOIYJJFAXRSHM-UHFFFAOYSA-N 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 239000003085 diluting agent Substances 0.000 claims abstract description 28
- 239000003814 drug Substances 0.000 claims abstract description 24
- 239000004480 active ingredient Substances 0.000 claims abstract description 21
- -1 carbonamido Chemical group 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 239000011734 sodium Substances 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract 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 claims abstract description 8
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 8
- 239000003826 tablet Substances 0.000 claims abstract description 8
- 239000002775 capsule Substances 0.000 claims abstract description 7
- XXFKYVPYCORMHQ-UHFFFAOYSA-N 5-amino-2-[(4-bromophenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=C(Br)C=C1 XXFKYVPYCORMHQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000008298 dragée Substances 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 239000006187 pill Substances 0.000 claims abstract description 6
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 6
- 239000011591 potassium Substances 0.000 claims abstract description 6
- 239000004094 surface-active agent Substances 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 5
- 239000000829 suppository Substances 0.000 claims abstract description 5
- 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 claims abstract description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims abstract description 4
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229960002442 glucosamine Drugs 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- OBSLWIKITOYASJ-YDEIVXIUSA-N (3r,4r,5s,6r)-6-(hydroxymethyl)-3-(methylamino)oxane-2,4,5-triol Chemical class CN[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OBSLWIKITOYASJ-YDEIVXIUSA-N 0.000 claims abstract description 3
- DQPSGRGQVKFYCB-UHFFFAOYSA-N 5-amino-2-[(3,4-dimethylphenyl)methyl]-1h-pyrazol-3-one Chemical compound C1=C(C)C(C)=CC=C1CN1C(=O)C=C(N)N1 DQPSGRGQVKFYCB-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 29
- 241001465754 Metazoa Species 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- LZIZCFXUTHHUFV-UHFFFAOYSA-N 5-amino-2-[(4-chlorophenyl)methyl]-1h-pyrazol-3-one Chemical group N1C(N)=CC(=O)N1CC1=CC=C(Cl)C=C1 LZIZCFXUTHHUFV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 230000004060 metabolic process Effects 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims 1
- 239000005414 inactive ingredient Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 abstract 1
- 239000000644 isotonic solution Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000008174 sterile solution Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 184
- 235000019441 ethanol Nutrition 0.000 description 69
- 239000000243 solution Substances 0.000 description 42
- 239000002253 acid Substances 0.000 description 38
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 125000004494 ethyl ester group Chemical group 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000003756 stirring Methods 0.000 description 19
- 239000013078 crystal Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 230000029142 excretion Effects 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 241000700159 Rattus Species 0.000 description 9
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000002934 diuretic Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 210000002700 urine Anatomy 0.000 description 5
- 241000416162 Astragalus gummifer Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229920001615 Tragacanth Polymers 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 230000001427 coherent effect Effects 0.000 description 4
- 239000003792 electrolyte Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000000894 saliuretic effect Effects 0.000 description 4
- 239000000196 tragacanth Substances 0.000 description 4
- 235000010487 tragacanth Nutrition 0.000 description 4
- 229940116362 tragacanth Drugs 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 235000012216 bentonite Nutrition 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 230000004526 pharmaceutical effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007921 spray 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
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- PGKQKXFTQSASKN-UHFFFAOYSA-N 5-amino-2-[(2,5-dichlorophenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC(Cl)=CC=C1Cl PGKQKXFTQSASKN-UHFFFAOYSA-N 0.000 description 2
- NSHZFGXITCLAOF-UHFFFAOYSA-N 5-amino-2-[(3-chloro-4-methylphenyl)methyl]-1h-pyrazol-3-one Chemical compound C1=C(Cl)C(C)=CC=C1CN1C(=O)C=C(N)N1 NSHZFGXITCLAOF-UHFFFAOYSA-N 0.000 description 2
- XCOJGEZPUZLRLE-UHFFFAOYSA-N 5-amino-2-[(3-chlorophenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=CC(Cl)=C1 XCOJGEZPUZLRLE-UHFFFAOYSA-N 0.000 description 2
- FUCPRWCEWUOIFL-UHFFFAOYSA-N 5-amino-2-[(4-phenylphenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=C(C=2C=CC=CC=2)C=C1 FUCPRWCEWUOIFL-UHFFFAOYSA-N 0.000 description 2
- ZRFGRBBMYMLVGE-UHFFFAOYSA-N 5-amino-2-[[3-(trifluoromethyl)phenyl]methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=CC(C(F)(F)F)=C1 ZRFGRBBMYMLVGE-UHFFFAOYSA-N 0.000 description 2
- QITDLJYCHQTOGS-UHFFFAOYSA-N 5-amino-2-[[4-(trifluoromethoxy)phenyl]methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=C(OC(F)(F)F)C=C1 QITDLJYCHQTOGS-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 241000206672 Gelidium Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 150000001411 amidrazones Chemical class 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Chemical class 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229920002678 cellulose Chemical class 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 229940030606 diuretics Drugs 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
- XLTPBSBNLKQLHB-UHFFFAOYSA-N ethyl 3-amino-3-ethoxyprop-2-enoate Chemical compound CCOC(N)=CC(=O)OCC XLTPBSBNLKQLHB-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000047 product Substances 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
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000001993 wax 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
- QKUSRPMMOKELAO-UHFFFAOYSA-N (2,4-dimethylphenyl)methylhydrazine Chemical compound CC1=CC=C(CNN)C(C)=C1 QKUSRPMMOKELAO-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
- 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
- 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
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
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- 239000001117 sulphuric acid Substances 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
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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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
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 (2)
| Publication Number | Publication Date |
|---|---|
| IL42562A0 IL42562A0 (en) | 1973-08-29 |
| IL42562A true IL42562A (en) | 1977-05-31 |
Family
ID=5848526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42562A IL42562A (en) | 1972-06-23 | 1973-06-20 | Pharmaceutical compositions containing 3-amino-pyrazol-5-ones |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE801227A (en:Method) |
| DE (1) | DE2230675A1 (en:Method) |
| FR (1) | FR2189071B1 (en:Method) |
| GB (1) | GB1391052A (en:Method) |
| IE (1) | IE37835B1 (en:Method) |
| IL (1) | IL42562A (en:Method) |
| LU (1) | LU67748A1 (en:Method) |
| NL (1) | NL7308648A (en:Method) |
| ZA (1) | ZA734240B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE30420E (en) * | 1973-04-17 | 1980-10-21 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| DE2319278C2 (de) * | 1973-04-17 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Pharmazeutisches Mittel |
| US4081596A (en) * | 1973-04-17 | 1978-03-28 | 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 BE BE132532A patent/BE801227A/xx unknown
- 1973-06-21 NL NL7308648A patent/NL7308648A/xx unknown
- 1973-06-22 FR FR7322954A patent/FR2189071B1/fr not_active Expired
- 1973-06-22 ZA ZA734240A patent/ZA734240B/xx unknown
- 1973-06-22 GB GB2978673A patent/GB1391052A/en not_active Expired
- 1973-06-22 IE IE1036/73A patent/IE37835B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU5720073A (en) | 1975-01-09 |
| NL7308648A (en:Method) | 1973-12-27 |
| FR2189071B1 (en:Method) | 1977-09-09 |
| IE37835L (en) | 1973-12-23 |
| IE37835B1 (en) | 1977-10-26 |
| ZA734240B (en) | 1974-05-29 |
| IL42562A0 (en) | 1973-08-29 |
| BE801227A (fr) | 1973-12-21 |
| FR2189071A1 (en:Method) | 1974-01-25 |
| GB1391052A (en) | 1975-04-16 |
| LU67748A1 (en:Method) | 1973-08-16 |
| DE2230675A1 (de) | 1974-01-10 |
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