SU545258A3 - Способ получени 1-замещенных пиразолонов-5 или их солей - Google Patents

Способ получени 1-замещенных пиразолонов-5 или их солей

Info

Publication number: SU545258A3
Authority: SU; USSR - Soviet Union
Prior art keywords: methyl; amino; pyrazolone; ethyl; ester
Prior art date: 1973-04-17

Application number

SU2017874A

Other languages

English (en)

Russian (ru)

Inventor

Меллер Эйке

Менг Карл

Вехингер Эгберт

Горстманн Гаральд

Original Assignee

Байер Аг (Фирма)

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-04-17

Filing date

1974-04-15

Publication date

1977-01-30

1974-04-15 Application filed by Байер Аг (Фирма) filed Critical Байер Аг (Фирма)

1977-01-30 Application granted granted Critical

1977-01-30 Publication of SU545258A3 publication Critical patent/SU545258A3/ru

Links

238000000034 method Methods 0.000 title claims description 6
150000003839 salts Chemical class 0.000 title claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
125000004494 ethyl ester group Chemical group 0.000 claims description 24
-1 aralkoxy Chemical group 0.000 claims description 19
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
150000001242 acetic acid derivatives Chemical class 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
150000003460 sulfonic acids Chemical class 0.000 claims description 2
239000002184 metal Substances 0.000 claims 3
229910052751 metal Inorganic materials 0.000 claims 3
125000003342 alkenyl group Chemical group 0.000 claims 2
150000002739 metals Chemical class 0.000 claims 2
125000003710 aryl alkyl group Chemical group 0.000 claims 1
150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
150000004679 hydroxides Chemical class 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000003107 substituted aryl group Chemical group 0.000 claims 1
239000000047 product Substances 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
150000001408 amides Chemical class 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000000203 mixture Substances 0.000 description 5
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
150000001298 alcohols Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
GWLKCPXYBLCEKC-UHFFFAOYSA-N 1,2-dichloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1Cl GWLKCPXYBLCEKC-UHFFFAOYSA-N 0.000 description 1
ZHVMMRGELMHLJB-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)ethylhydrazine Chemical compound NNC(C)C1=CC=C(Cl)C(Cl)=C1 ZHVMMRGELMHLJB-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
LIHUTSFYFGCWQP-UHFFFAOYSA-N 2-cyano-n-methylacetamide Chemical compound CNC(=O)CC#N LIHUTSFYFGCWQP-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OQWSVCXXAYKEFF-UHFFFAOYSA-N Brucin Natural products COc1cc2N3C4C5C(CC3=O)OC=CC6CN7CCC4(C7CC56)c2cc1OC OQWSVCXXAYKEFF-UHFFFAOYSA-N 0.000 description 1
240000005109 Cryptomeria japonica Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
RYSHIRFTLKZVIH-UHFFFAOYSA-N N,N-diethylcyanoacetamide Chemical compound CCN(CC)C(=O)CC#N RYSHIRFTLKZVIH-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
FONFJFUBWWRBKA-UHFFFAOYSA-N [N].[I] Chemical compound [N].[I] FONFJFUBWWRBKA-UHFFFAOYSA-N 0.000 description 1
UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase 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
230000008033 biological extinction Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000004803 chlorobenzyl 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
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
BZEVNDPHINRVAB-UHFFFAOYSA-N ethane ethanol Chemical compound CC.CCO.CCO.CCO BZEVNDPHINRVAB-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 1
OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
PWKKBTPSCGLYBR-UHFFFAOYSA-N hexyl 2-cyanoacetate Chemical compound CCCCCCOC(=O)CC#N PWKKBTPSCGLYBR-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
MGZNARROBKPUST-UHFFFAOYSA-N n-butyl-2-cyanoacetamide Chemical compound CCCCNC(=O)CC#N MGZNARROBKPUST-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 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
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
238000011197 physicochemical method Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 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
238000003786 synthesis reaction Methods 0.000 description 1
BFNYNEMRWHFIMR-UHFFFAOYSA-N tert-butyl 2-cyanoacetate Chemical compound CC(C)(C)OC(=O)CC#N BFNYNEMRWHFIMR-UHFFFAOYSA-N 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 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)
Plural Heterocyclic Compounds (AREA)

SU2017874A 1973-04-17 1974-04-15 Способ получени 1-замещенных пиразолонов-5 или их солей SU545258A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2319280A DE2319280A1 (de)	1973-04-17	1973-04-17	1-substituierte pyrazolone-(5), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel

Publications (1)

Publication Number	Publication Date
SU545258A3 true SU545258A3 (ru)	1977-01-30

Family

ID=5878315

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
SU2017874A SU545258A3 (ru)	1973-04-17	1974-04-15	Способ получени 1-замещенных пиразолонов-5 или их солей
SU2114556A SU545257A3 (ru)	1973-04-17	1975-03-19	Способ получени 1-замещенных пиразолонов-5 или их солей
SU2115104A SU544372A3 (ru)	1973-04-17	1975-03-19	Способ получени 3-аминопиразолонов -(5) или их солей

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
SU2114556A SU545257A3 (ru)	1973-04-17	1975-03-19	Способ получени 1-замещенных пиразолонов-5 или их солей
SU2115104A SU544372A3 (ru)	1973-04-17	1975-03-19	Способ получени 3-аминопиразолонов -(5) или их солей

Country Status (8)

Country	Link
BE (1)	BE813747A (fr)
CS (1)	CS189629B2 (fr)
DE (1)	DE2319280A1 (fr)
PL (1)	PL102081B1 (fr)
RO (1)	RO69470A2 (fr)
SU (3)	SU545258A3 (fr)
YU (1)	YU280681A (fr)
ZA (1)	ZA742381B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2356906C2 (ru) *	2002-08-08	2009-05-27	Киссеи Фармасьютикал Ко., Лтд.	Производные пиразола, лекарственные композиции, содержащие эти производные, их применение в медицине и промежуточные соединения для их получения

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2363139A1 (de) *	1973-12-19	1975-07-10	Bayer Ag	1-substituierte pyrazolone-(5), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE3306366A1 (de) *	1983-02-24	1984-08-30	Bayer Ag, 5090 Leverkusen	Muzolimin enthaltende arzneimittel, deren verwendung und verfahren zu deren herstellung
DE3436383A1 (de) *	1984-10-04	1986-04-10	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von pyrazolonderivaten

1973
- 1973-04-17 DE DE2319280A patent/DE2319280A1/de not_active Withdrawn
1974
- 1974-04-02 CS CS742370A patent/CS189629B2/cs unknown
- 1974-04-15 RO RO197485201Q patent/RO69470A2/fr unknown
- 1974-04-15 SU SU2017874A patent/SU545258A3/ru active
- 1974-04-16 PL PL1974196003A patent/PL102081B1/pl unknown
- 1974-04-16 BE BE143223A patent/BE813747A/fr not_active IP Right Cessation
- 1974-04-16 ZA ZA00742381A patent/ZA742381B/xx unknown
1975
- 1975-03-19 SU SU2114556A patent/SU545257A3/ru active
- 1975-03-19 SU SU2115104A patent/SU544372A3/ru active
1981
- 1981-12-02 YU YU02806/81A patent/YU280681A/xx unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2356906C2 (ru) *	2002-08-08	2009-05-27	Киссеи Фармасьютикал Ко., Лтд.	Производные пиразола, лекарственные композиции, содержащие эти производные, их применение в медицине и промежуточные соединения для их получения

Also Published As

Publication number	Publication date
RO69470A2 (fr)	1981-11-05
SU544372A3 (ru)	1977-01-25
ZA742381B (en)	1975-04-30
SU545257A3 (ru)	1977-01-30
DE2319280A1 (de)	1974-11-07
CS189629B2 (en)	1979-04-30
PL102081B1 (pl)	1979-02-28
BE813747A (fr)	1974-10-16
YU280681A (en)	1982-06-30

Publication	Publication Date	Title
SU649312A3 (ru)	1979-02-25	Способ получени 4-(полиалкоксифенил)2-пирролидонов
CA1274831A (fr)	1990-10-02	Preparation d'esters pyridine-2,3-dicarboxylate substitues et disubstitues
CN1190961A (zh)	1998-08-19	N－取代的3－羟基吡唑类化合物的制备方法
GB2036722A (en)	1980-07-02	2-Methyl-dihydropyridines
SU545258A3 (ru)	1977-01-30	Способ получени 1-замещенных пиразолонов-5 или их солей
PL96883B1 (pl)	1978-01-31	Sposob wytwarzania nowych 1-podstawionych pirazolonow-/5/
KR960001913B1 (ko)	1996-02-06	3-시아노-4-아릴-피롤의 제조방법
Hegde et al.	1993	Synthesis of 1, 6‐dihydro‐5‐hydroxy‐6‐oxo‐3‐(trifluoromethyl)‐4‐pyridazinecarboxylates
Graham et al.	1949	Investigation of Pyrazole Compounds. VIII. 1 Synthesis and Acylation of Pyrazolones Derived from Hydrazine and Methylhydrazine
US4436921A (en)	1984-03-13	1-(4-Aminobenzyl)-2,3-dioxopiperazine derivatives, acid addition salts thereof and process for producing same
Dragovich et al.	2007	Regiospecific synthesis of 1, 5-disubstituted-1H-pyrazoles containing differentiated 3, 4-dicarboxylic acid esters via Suzuki coupling of the corresponding 5-trifluoromethane sulfonates
US5066825A (en)	1991-11-19	Process for preparing a naphthalene derivative
US4317920A (en)	1982-03-02	Arylacetic acid derivatives
SK36694A3 (en)	1995-02-08	Method of preparation of aminotriazine derivatives
US4958030A (en)	1990-09-18	Process for the preparation of 3-phenylpyrrole derivatives
Kakehi et al.	1990	Preparation of new nitrogen-bridged heterocycles. 21. A facile synthesis of 2-indolizinethiols using new protecting groups.
EP2818461A1 (fr)	2014-12-31	Procédé de préparation de dérivés d'acide 6-trifluoromethylpyridine-3-carboxylique à partir de 4,4,4-trifluoro-3-oxobutanoyl de chlorure
JPH0753711B2 (ja)	1995-06-07	新規なピロリノン類及びその製法
US3442893A (en)	1969-05-06	Steroid analogs
US4459407A (en)	1984-07-10	1-(4-Aminobenzyl)-2,3-dioxopiperazine derivatives and salts thereof
CA1052383A (fr)	1979-04-10	Derives de triazole-1,2,4
EP0714892A1 (fr)	1996-06-05	Dérivés de 1H-Pyrrolo[1,2-b][1,2,4]triazole et leur préparation via dérivés de 1H-1,2,4-triazole
CA2226768A1 (fr)	1998-07-16	Procede de preparation d'esters 1-alkyl-pyrazole-5-carboxyliques
US3123616A (en)	1964-03-03	C o nxe
EP3741745B1 (fr)	2023-04-26	Procédé de fabrication de dérivé de n-alcoxycarbonylpipéridine, et intermédiaire de celui-ci

SU545258A3 - Способ получени 1-замещенных пиразолонов-5 или их солей - Google Patents

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