GB732820A - Process for preparing 1,4-diphenyl-3,5-diketopyrazolidine and its derivatives - Google Patents
Process for preparing 1,4-diphenyl-3,5-diketopyrazolidine and its derivativesInfo
- Publication number
- GB732820A GB732820A GB25727/53A GB2572753A GB732820A GB 732820 A GB732820 A GB 732820A GB 25727/53 A GB25727/53 A GB 25727/53A GB 2572753 A GB2572753 A GB 2572753A GB 732820 A GB732820 A GB 732820A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diketo
- diphenyl
- pyrazolidine
- alkyl
- aralkyl
- 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.)
- Expired
Links
- ZZMSHBOVYPIYOB-UHFFFAOYSA-N 1,4-diphenylpyrazolidine-3,5-dione Chemical compound O=C1NN(C=2C=CC=CC=2)C(=O)C1C1=CC=CC=C1 ZZMSHBOVYPIYOB-UHFFFAOYSA-N 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 229940067157 phenylhydrazine Drugs 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000007529 inorganic bases Chemical class 0.000 abstract 2
- 150000007530 organic bases Chemical class 0.000 abstract 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 2
- VVDPMDVGFLVBGN-UHFFFAOYSA-N 1,2,4-triphenylpyrazolidine-3,5-dione Chemical compound O=C1C(C=2C=CC=CC=2)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VVDPMDVGFLVBGN-UHFFFAOYSA-N 0.000 abstract 1
- UGEIAEWCPVXUKE-UHFFFAOYSA-N 1,4-dibenzylpyrazolidine-3,5-dione Chemical class C(C1=CC=CC=C1)N1NC(C(C1=O)CC1=CC=CC=C1)=O UGEIAEWCPVXUKE-UHFFFAOYSA-N 0.000 abstract 1
- XQKKQQHRIQLLKD-UHFFFAOYSA-N 1-methyl-2,4-diphenylpyrazolidine-3,5-dione Chemical compound C1(=CC=CC=C1)N1N(C(C(C1=O)C1=CC=CC=C1)=O)C XQKKQQHRIQLLKD-UHFFFAOYSA-N 0.000 abstract 1
- HQEMXYMDPMITCK-UHFFFAOYSA-N 4-benzylpyrazolidine-3,5-dione Chemical class O=C1NNC(=O)C1CC1=CC=CC=C1 HQEMXYMDPMITCK-UHFFFAOYSA-N 0.000 abstract 1
- -1 4-n-butyl- Chemical group 0.000 abstract 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 1,4-diphenyl-3,5-diketo-pyrazolidine and its derivatives having the formula <FORM:0732820/IV (b)/1> wherein R1 represents hydrogen, alkyl, aryl or aralkyl and R2 represents hydrogen, alkyl or aralkyl, and their salts with inorganic or organic bases. They are prepared by condensing phenyl malonic acid, its dialkyl esters, esteramide or dihalide with phenyl hydrazine or its alkyl-, aralkyl-, or aryl-substituted derivatives and, if desired, reacting the 1,4-diphenyl-3,5-diketo-pyrazolidine obtained with alkyl- or aralkyl-halides in the presence of alkaline agents. N-acyl-phenyl hydrazine or its b -alkyl derivatives may be used instead of phenyl hydrazine. Examples describe the preparation of 1,4-diphenyl-3,5-diketo-pyrazolidine (by various methods) and its sodium salt; 1,4-diphenyl-2-methyl - 3,5 - diketo - pyrazolidine; 1,2,4-triphenyl - 3,5 - diketo - pyrazolidine and its 4-methyl derivative; 1,4-diphenyl-4-methyl-, 4-ethyl-, 4-n-butyl-, and 4-benzyl-3,5-diketo-pyrazolidines; and 1,4-diphenyl-2-benzyl-4-methyl- and 2,4-dibenzyl-3,5-diketo-pyrazolidines.ALSO:Salts of 1,4-diphenyl-3,5-diketo-pyrazolidine, and its derivatives, with inorganic and organic bases may be used in aqueous solutions for injecting for analgesic and antipyretic purposes. The parent compounds correspond to the general formula <FORM:0732820/VI/1> wherein R1 and R2 represent hydrogen, alkyl or aralkyl, and R1 may also be aryl. The salts may be combined in aqueous solution with known analgesics, e.g. 4-dimethyl-amino-1-phenyl-2,3-dimethyl-pyrazolone, to form concentrations of 15 per cent and higher of each component and having a pH of 7 to 8.5.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE732820X | 1952-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB732820A true GB732820A (en) | 1955-06-29 |
Family
ID=6639926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25727/53A Expired GB732820A (en) | 1952-09-18 | 1953-09-17 | Process for preparing 1,4-diphenyl-3,5-diketopyrazolidine and its derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB732820A (en) |
-
1953
- 1953-09-17 GB GB25727/53A patent/GB732820A/en not_active Expired
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