IL42560A - 1 - ethylmethyl - 3 - amino - pyrazole - 5 - helium and their salts and process for their production - Google Patents
1 - ethylmethyl - 3 - amino - pyrazole - 5 - helium and their salts and process for their productionInfo
- Publication number
- IL42560A IL42560A IL42560A IL4256073A IL42560A IL 42560 A IL42560 A IL 42560A IL 42560 A IL42560 A IL 42560A IL 4256073 A IL4256073 A IL 4256073A IL 42560 A IL42560 A IL 42560A
- Authority
- IL
- Israel
- Prior art keywords
- amino
- pyrazol
- group
- general formula
- ethanol
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- -1 sulphamoyl Chemical group 0.000 claims abstract description 28
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 125000003282 alkyl amino 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 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 229910052740 iodine Inorganic materials 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 157
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 9
- 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 description 7
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 7
- 150000001411 amidrazones Chemical class 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- ACOIYJJFAXRSHM-UHFFFAOYSA-N 5-aminopyrazol-3-one Chemical class NC1=CC(=O)N=N1 ACOIYJJFAXRSHM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 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 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 239000004411 aluminium Substances 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 229960002442 glucosamine Drugs 0.000 claims 1
- 159000000014 iron salts Chemical class 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 18
- 239000002934 diuretic Substances 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 230000001882 diuretic effect Effects 0.000 abstract description 4
- 230000000894 saliuretic effect Effects 0.000 abstract description 4
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- XSFKCGABINPZRK-UHFFFAOYSA-N 4-aminopyrazol-3-one Chemical class NC1=CN=NC1=O XSFKCGABINPZRK-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
- 239000002253 acid Substances 0.000 description 40
- 238000002844 melting Methods 0.000 description 38
- 230000008018 melting Effects 0.000 description 38
- 239000000243 solution Substances 0.000 description 38
- 125000004494 ethyl ester group Chemical group 0.000 description 29
- 238000003756 stirring Methods 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 25
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 24
- 230000029142 excretion Effects 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 241000700159 Rattus Species 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- YTLYLLTVENPWFT-UHFFFAOYSA-N 3-aminoprop-2-enoic acid Chemical class NC=CC(O)=O YTLYLLTVENPWFT-UHFFFAOYSA-N 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- XLTPBSBNLKQLHB-UHFFFAOYSA-N ethyl 3-amino-3-ethoxyprop-2-enoate Chemical compound CCOC(N)=CC(=O)OCC XLTPBSBNLKQLHB-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 210000002700 urine Anatomy 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- DTDHQQPOMUQSMA-UHFFFAOYSA-N ethyl 3-amino-2-ethoxyprop-2-enoate Chemical compound CCOC(=O)C(=CN)OCC DTDHQQPOMUQSMA-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
- 150000002429 hydrazines Chemical class 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
- QKUSRPMMOKELAO-UHFFFAOYSA-N (2,4-dimethylphenyl)methylhydrazine Chemical compound CC1=CC=C(CNN)C(C)=C1 QKUSRPMMOKELAO-UHFFFAOYSA-N 0.000 description 2
- OOMBRKGIWITBLL-UHFFFAOYSA-N (2-fluorophenyl)methylhydrazine Chemical compound NNCC1=CC=CC=C1F OOMBRKGIWITBLL-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
- NRAZPMKRDZYKGM-UHFFFAOYSA-N (3-ethylphenyl)methylhydrazine Chemical compound CCC1=CC=CC(CNN)=C1 NRAZPMKRDZYKGM-UHFFFAOYSA-N 0.000 description 2
- SAVAJKHGIQLPDD-UHFFFAOYSA-N (3-fluorophenyl)methylhydrazine Chemical compound NNCC1=CC=CC(F)=C1 SAVAJKHGIQLPDD-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
- SABLROJJEJTWTE-UHFFFAOYSA-N (4-bromophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Br)C=C1 SABLROJJEJTWTE-UHFFFAOYSA-N 0.000 description 2
- YMMCBGIHBVKZGD-UHFFFAOYSA-N (4-fluorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(F)C=C1 YMMCBGIHBVKZGD-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
- 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
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- XNYCYBBGRXJOCO-UHFFFAOYSA-N 5-amino-2-[(3-bromo-4-chlorophenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=C(Cl)C(Br)=C1 XNYCYBBGRXJOCO-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- RYSHIRFTLKZVIH-UHFFFAOYSA-N N,N-diethylcyanoacetamide Chemical compound CCN(CC)C(=O)CC#N RYSHIRFTLKZVIH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 229940030606 diuretics Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 239000011780 sodium chloride Substances 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
- 229940116362 tragacanth Drugs 0.000 description 2
- 235000010487 tragacanth Nutrition 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 1
- IXRQTCDPQZMNSN-UHFFFAOYSA-N (2-methylphenyl)methylhydrazine Chemical compound CC1=CC=CC=C1CNN IXRQTCDPQZMNSN-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
- LGYQGASEWMVLDF-UHFFFAOYSA-N (3,4-dibromophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Br)C(Br)=C1 LGYQGASEWMVLDF-UHFFFAOYSA-N 0.000 description 1
- FAKTXRHJGGNPCG-UHFFFAOYSA-N (3,4-diethylphenyl)methylhydrazine Chemical compound CCC1=CC=C(CNN)C=C1CC FAKTXRHJGGNPCG-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
- ZUFKJOBIQWYVSA-UHFFFAOYSA-N (3-bromo-4-chlorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(Cl)C(Br)=C1 ZUFKJOBIQWYVSA-UHFFFAOYSA-N 0.000 description 1
- FQAZMGYQHZYAQR-UHFFFAOYSA-N (3-butoxyphenyl)methylhydrazine Chemical compound CCCCOC1=CC=CC(CNN)=C1 FQAZMGYQHZYAQR-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
- XAORWJJKXUCVQP-UHFFFAOYSA-N (3-methyl-4-propylphenyl)methylhydrazine Chemical compound CCCC1=CC=C(CNN)C=C1C XAORWJJKXUCVQP-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
- IZSXKLRDDQUEGY-UHFFFAOYSA-N (3-propylphenyl)methylhydrazine Chemical compound CCCC1=CC=CC(CNN)=C1 IZSXKLRDDQUEGY-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
- IAFCITUSAGIDIH-UHFFFAOYSA-N (4-butoxyphenyl)methylhydrazine Chemical compound CCCCOC1=CC=C(CNN)C=C1 IAFCITUSAGIDIH-UHFFFAOYSA-N 0.000 description 1
- PTFHUJCUFFSGIA-UHFFFAOYSA-N (4-butylphenyl)methylhydrazine Chemical compound CCCCC1=CC=C(CNN)C=C1 PTFHUJCUFFSGIA-UHFFFAOYSA-N 0.000 description 1
- OSEUIXWRVRPACB-UHFFFAOYSA-N (4-chloro-3-ethoxyphenyl)methylhydrazine Chemical compound CCOC1=CC(CNN)=CC=C1Cl OSEUIXWRVRPACB-UHFFFAOYSA-N 0.000 description 1
- HNSMCIGVJAAADX-UHFFFAOYSA-N (4-chloro-3-methoxyphenyl)methylhydrazine Chemical compound COC1=CC(CNN)=CC=C1Cl HNSMCIGVJAAADX-UHFFFAOYSA-N 0.000 description 1
- YUBWRJFBZNBNKZ-UHFFFAOYSA-N (4-ethylphenyl)methylhydrazine Chemical compound CCC1=CC=C(CNN)C=C1 YUBWRJFBZNBNKZ-UHFFFAOYSA-N 0.000 description 1
- JRBYEYSVCBDBQO-UHFFFAOYSA-N (4-iodophenyl)methylhydrazine Chemical compound NNCC1=CC=C(I)C=C1 JRBYEYSVCBDBQO-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
- FHCLSOWEUAPQHY-UHFFFAOYSA-N (4-propylphenyl)methylhydrazine Chemical compound CCCC1=CC=C(CNN)C=C1 FHCLSOWEUAPQHY-UHFFFAOYSA-N 0.000 description 1
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical class N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- HRGQEKKNLHJZGZ-UHFFFAOYSA-N 2-methylpropyl 2-cyanoacetate Chemical compound CC(C)COC(=O)CC#N HRGQEKKNLHJZGZ-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 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
- DFKKJQABUJCNLE-UHFFFAOYSA-N 4-(hydrazinylmethyl)phenol Chemical compound NNCC1=CC=C(O)C=C1 DFKKJQABUJCNLE-UHFFFAOYSA-N 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
- KUWAZEXJGOUYDO-UHFFFAOYSA-N 5-amino-2-(naphthalen-2-ylmethyl)-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=C(C=CC=C2)C2=C1 KUWAZEXJGOUYDO-UHFFFAOYSA-N 0.000 description 1
- NMONQDRBGVKMIJ-UHFFFAOYSA-N 5-amino-2-[(1-bromocyclohexa-2,4-dien-1-yl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1(Br)C=CC=CC1 NMONQDRBGVKMIJ-UHFFFAOYSA-N 0.000 description 1
- JEFVLIROFVCYFG-UHFFFAOYSA-N 5-amino-2-[(2,4,5-trichlorophenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC(Cl)=C(Cl)C=C1Cl JEFVLIROFVCYFG-UHFFFAOYSA-N 0.000 description 1
- WHQOKVDGOHKGKM-UHFFFAOYSA-N 5-amino-2-[(2-chloro-4-fluorophenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=C(F)C=C1Cl WHQOKVDGOHKGKM-UHFFFAOYSA-N 0.000 description 1
- XXDRSEAVUZLRMI-UHFFFAOYSA-N 5-amino-2-[(2-methylphenyl)methyl]-1h-pyrazol-3-one Chemical compound CC1=CC=CC=C1CN1C(=O)C=C(N)N1 XXDRSEAVUZLRMI-UHFFFAOYSA-N 0.000 description 1
- SYLCUGJZCYXXOW-UHFFFAOYSA-N 5-amino-2-[(2-nitrophenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=CC=C1[N+]([O-])=O SYLCUGJZCYXXOW-UHFFFAOYSA-N 0.000 description 1
- NPNXOUNGVXGLOG-UHFFFAOYSA-N 5-amino-2-[(3-butoxyphenyl)methyl]-1h-pyrazol-3-one Chemical compound CCCCOC1=CC=CC(CN2C(C=C(N)N2)=O)=C1 NPNXOUNGVXGLOG-UHFFFAOYSA-N 0.000 description 1
- IDUNFMRCUPDMCT-UHFFFAOYSA-N 5-amino-2-[(3-fluorophenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=CC(F)=C1 IDUNFMRCUPDMCT-UHFFFAOYSA-N 0.000 description 1
- NBGCNSRGVBGWKS-UHFFFAOYSA-N 5-amino-2-[(3-nitrophenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=CC([N+]([O-])=O)=C1 NBGCNSRGVBGWKS-UHFFFAOYSA-N 0.000 description 1
- ZKOFIMQWKBOZRX-UHFFFAOYSA-N 5-amino-2-[(4-chloro-3-methylphenyl)methyl]-1h-pyrazol-3-one Chemical compound C1=C(Cl)C(C)=CC(CN2C(C=C(N)N2)=O)=C1 ZKOFIMQWKBOZRX-UHFFFAOYSA-N 0.000 description 1
- IEVPZTYKWHTDON-UHFFFAOYSA-N 5-amino-2-[(4-fluorophenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=C(F)C=C1 IEVPZTYKWHTDON-UHFFFAOYSA-N 0.000 description 1
- XAGMZPIKYXQBNQ-UHFFFAOYSA-N 5-amino-2-[(4-methylphenyl)methyl]-1h-pyrazol-3-one Chemical compound C1=CC(C)=CC=C1CN1C(=O)C=C(N)N1 XAGMZPIKYXQBNQ-UHFFFAOYSA-N 0.000 description 1
- QEFJQRIUBCGBNA-UHFFFAOYSA-N 5-amino-2-[(4-nitrophenyl)methyl]-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1CC1=CC=C([N+]([O-])=O)C=C1 QEFJQRIUBCGBNA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000820057 Ithone Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 235000003407 Sigesbeckia orientalis Nutrition 0.000 description 1
- 240000003801 Sigesbeckia orientalis Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- DMMFSCDINNZFAG-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]methylhydrazine Chemical compound NNCC1=CC=CC=C1C(F)(F)F DMMFSCDINNZFAG-UHFFFAOYSA-N 0.000 description 1
- TVQQKOLNFGDRKY-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]methylhydrazine Chemical compound NNCC1=CC=C(OC(F)(F)F)C=C1 TVQQKOLNFGDRKY-UHFFFAOYSA-N 0.000 description 1
- QYZCPOGLBTUVLP-UHFFFAOYSA-N [4-chloro-3-(trifluoromethyl)phenyl]methylhydrazine Chemical compound NNCC1=CC=C(Cl)C(C(F)(F)F)=C1 QYZCPOGLBTUVLP-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- RCUIWQWWDLZNMS-UHFFFAOYSA-N benzyl 2-cyanoacetate Chemical compound N#CCC(=O)OCC1=CC=CC=C1 RCUIWQWWDLZNMS-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 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
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000006278 bromobenzyl group Chemical group 0.000 description 1
- DJACTCNGCHPGOI-UHFFFAOYSA-N butyl 2-cyanoacetate Chemical compound CCCCOC(=O)CC#N DJACTCNGCHPGOI-UHFFFAOYSA-N 0.000 description 1
- 125000006487 butyl benzyl group Chemical group 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical class OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- WXMSGMOIAQWILS-UHFFFAOYSA-N ethyl 2-ethoxyprop-2-enoate Chemical compound CCOC(=C)C(=O)OCC WXMSGMOIAQWILS-UHFFFAOYSA-N 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
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- PWKKBTPSCGLYBR-UHFFFAOYSA-N hexyl 2-cyanoacetate Chemical compound CCCCCCOC(=O)CC#N PWKKBTPSCGLYBR-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- MGZNARROBKPUST-UHFFFAOYSA-N n-butyl-2-cyanoacetamide Chemical compound CCCCNC(=O)CC#N MGZNARROBKPUST-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BESQLCCRQYTQQI-UHFFFAOYSA-N propan-2-yl 2-cyanoacetate Chemical compound CC(C)OC(=O)CC#N BESQLCCRQYTQQI-UHFFFAOYSA-N 0.000 description 1
- NLFIMXLLXGTDME-UHFFFAOYSA-N propyl 2-cyanoacetate Chemical compound CCCOC(=O)CC#N NLFIMXLLXGTDME-UHFFFAOYSA-N 0.000 description 1
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical compound O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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)
- 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)
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 (2)
| Publication Number | Publication Date |
|---|---|
| IL42560A0 IL42560A0 (en) | 1973-08-29 |
| IL42560A true IL42560A (en) | 1977-05-31 |
Family
ID=5848604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42560A IL42560A (en) | 1972-06-23 | 1973-06-20 | 1 - ethylmethyl - 3 - amino - pyrazole - 5 - helium and their salts and process for their production |
Country Status (29)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2319278C2 (de) * | 1973-04-17 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Pharmazeutisches Mittel |
| USRE30420E (en) * | 1973-04-17 | 1980-10-21 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| DE3436383A1 (de) * | 1984-10-04 | 1986-04-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von pyrazolonderivaten |
-
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
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