US3178441A - Pyridyl-pyrazolidine 3-ones - Google Patents
Pyridyl-pyrazolidine 3-ones Download PDFInfo
- Publication number
- US3178441A US3178441A US243598A US24359862A US3178441A US 3178441 A US3178441 A US 3178441A US 243598 A US243598 A US 243598A US 24359862 A US24359862 A US 24359862A US 3178441 A US3178441 A US 3178441A
- Authority
- US
- United States
- Prior art keywords
- phenyl
- general formula
- pyridyl
- pyrazolidone
- pyrazolidine
- 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 - Lifetime
Links
- -1 PYRAZOLIDIN-3-ONE COMPOUND Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical compound O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- KKLMJYDGZSAIQX-UHFFFAOYSA-N 2-(n-hydroxyanilino)acetic acid Chemical compound OC(=O)CN(O)C1=CC=CC=C1 KKLMJYDGZSAIQX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- ABZPCWYIRGIXJP-UHFFFAOYSA-N ethyl 3-pyridin-4-ylprop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=NC=C1 ABZPCWYIRGIXJP-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- NVXLIZQNSVLKPO-UHFFFAOYSA-N Glucosereductone Chemical compound O=CC(O)C=O NVXLIZQNSVLKPO-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004285 Potassium sulphite Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229960005219 gentisic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- HAYWTXQRYXYRAF-UHFFFAOYSA-N hydron;pyrazolidin-3-one;chloride Chemical compound Cl.O=C1CCNN1 HAYWTXQRYXYRAF-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- KRTLKPFLTASKCG-UHFFFAOYSA-N pyridin-4-ylhydrazine Chemical compound NNC1=CC=NC=C1 KRTLKPFLTASKCG-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/30—Developers
- G03C5/3028—Heterocyclic compounds
- G03C5/3035—Heterocyclic compounds containing a diazole ring
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/305—Additives other than developers
Definitions
- R R and R are the same or different and are hydrogen atoms or hydrocarbon groups.
- the compound l-phenyl- 3-pyrazolidone has received widespread commercial use, for which purpose it is customarily employed in association with another photographic developing substance with which it exhibits a superadditive effect.
- it may be used in association with hydroquinone, hydroxyphenyl glycine, gentisic acid, ascorbic acid, reductone and other substances.
- 3-pyrazolidone derivatives as defined below are extremely useful developing agents latl high vpI-l values and have a substantially greater solu- 1 ity.
- R may be, for example, furyl, thienyl, pyrryl, indolyl, pyridyl, thiazolyl, piperidyl, morpholinyl, pyrrolidinyl or benziminazolyl.
- R may be, for example, a phenyl group or an alkyl-, alkoxy-, halogenor other substituted phenyl group, or any of the heterocycles referred to above.
- R -CH CH--COOR (IV) where R is a hydrocarbon group and the other symbols have the meanings hereinbefore assigned.
- R with an orthophenylene diamine.
- the new developing substances of the present inven-' tion may be used in the same manner as 1-phenyl-3- pyrazolidone, but at pH values above 9.5, in association with hydroquinone, hydroxyphenyl glycine, or any other known developing agent with which the new compounds exert a superadditive effect.
- EXAMPLE 3 l-phenyl-5-4'-pyridylpyrazolidind-one
- the method of Example 1 was used with ethyl 3-4- pyridylacrylate.
- the pyrazolidin-3-one formed colourless plates, M. Pt. 161-162, by crystallisation from a mixture of ethanol and water.
- EXAMPLE 4 1 -p-chlr0pIze1zyI-5 -3 '-pyridylpyrazolidin-3-0ne
- EXAMPLE 5 1,5-bis-4-pyridylpyraz0lidin-3-0ne
- a solution of sodium (3.2 g.) in ethanol 100 ml.) was refluxed for 16 hours with 4-hydrazinopyridine (11.5 g.) and ethyl 3-4-pyridylacrylate (18.7 g.).
- the residue obtained after evaporation of the solvent under reduced pressure was refluxed with concentrated hydrochloric acid (80 ml.) for 2 /2 hours.
- the cooled solution was filtered, and the filtrate treated with crystalline sodium acetate (100 g.).
- EXAMPLE 8 5 -2-bcnzim inazolyl-I -phenyl pyraz0lidin-3-0r1e A mixture of 3-oxo-1-phenylpyrazolidine-S-carboxylic acid (5.0 g.), o-phenylene-diamine (2.62 g.), and 4 N hydrochloric acid (25 ml.) was refluxed for 2 hours.
- the solution was filtered hot (charcoal), and the cooled filtrate was neutralised with aqueous ammonia.
- EXAMPLE 9 5-2-benzimidaz0lyl-1-p-tolylpyraz0lidin-3-0ne hydrochloride A mixture of 3-oxo-1-p-tolylpyrazolidine-S-carboxylic acid (3.32 g.), o-phenylene diamine (1.63 g.), and 4 N hydrochloric acid (16 ml.) was refluxed for 2 hours. The crystalline solid which separated was collected after cooling the mixture, and was crystallised from dilute hydrochloric acid, to give the pyrazolidin-3-one hydrochloride a cream-coloured prisms, M. Pt. 265-267 (decomp).
- EXAMPLE 10 The following is a suitable developer composition according to the invention:
- R is selected from the group consisting of 2- pyridyl, 3-pyridyl and 4-pyridyl and R is selected from the class consisting of phenyl, halophen'yl and tolyl.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB45466/61A GB997033A (en) | 1961-12-19 | 1961-12-19 | Pyrazolidinone derivatives |
| GB45465/61A GB985653A (en) | 1961-12-19 | 1961-12-19 | Pyrazolidone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3178441A true US3178441A (en) | 1965-04-13 |
Family
ID=26265596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US243598A Expired - Lifetime US3178441A (en) | 1961-12-19 | 1962-12-10 | Pyridyl-pyrazolidine 3-ones |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3178441A (xx) |
| DE (1) | DE1445931A1 (xx) |
| GB (2) | GB997033A (xx) |
| NL (1) | NL286908A (xx) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4074051A (en) * | 1971-12-08 | 1978-02-14 | Minnesota Mining And Manufacturing Company | 3-Pyrazolidinone derivatives |
| US4095024A (en) * | 1975-01-31 | 1978-06-13 | Imperial Chemical Industries Limited | Process for the manufacture of 1-aryl-3-carboxypyrazolid-5-ones |
| US4550119A (en) * | 1983-05-23 | 1985-10-29 | Warner-Lambert Company | 2,4-Dihydro-5-[(substituted)phenyl]-4,4-disubstituted-3H-pyrazol-3-ones |
| US4551538A (en) * | 1984-12-20 | 1985-11-05 | American Home Products Corporation | Phenylpyrazolidine acetic acid derivatives |
| US5089515A (en) * | 1986-11-20 | 1992-02-18 | Mitsubishi Kasei Corporation | Lipid-peroxide formation inhibiting composition and novel compounds useful therefor |
| CN101333191B (zh) * | 2008-07-25 | 2013-04-03 | 浙江师范大学 | 一种2,5-二取代吡唑啉-3-酮类衍生物的制备方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2833779A (en) * | 1956-10-29 | 1958-05-06 | American Cyanamid Co | Substituted pyrazoles |
| US2981623A (en) * | 1954-03-15 | 1961-04-25 | Agfa Ag | Photographic developers |
| US3010827A (en) * | 1956-12-22 | 1961-11-28 | Agfa Ag | Photographic developer |
| US3041343A (en) * | 1959-10-14 | 1962-06-26 | Sandoz Ltd | 4-(thienyl-2'')-and 4-(pyridyl-3'')-5-aminopyrazoles |
-
0
- NL NL286908D patent/NL286908A/xx unknown
-
1961
- 1961-12-19 GB GB45466/61A patent/GB997033A/en not_active Expired
- 1961-12-19 GB GB45465/61A patent/GB985653A/en not_active Expired
-
1962
- 1962-12-10 US US243598A patent/US3178441A/en not_active Expired - Lifetime
- 1962-12-17 DE DE19621445931 patent/DE1445931A1/de active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2981623A (en) * | 1954-03-15 | 1961-04-25 | Agfa Ag | Photographic developers |
| US2833779A (en) * | 1956-10-29 | 1958-05-06 | American Cyanamid Co | Substituted pyrazoles |
| US3010827A (en) * | 1956-12-22 | 1961-11-28 | Agfa Ag | Photographic developer |
| US3041343A (en) * | 1959-10-14 | 1962-06-26 | Sandoz Ltd | 4-(thienyl-2'')-and 4-(pyridyl-3'')-5-aminopyrazoles |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4074051A (en) * | 1971-12-08 | 1978-02-14 | Minnesota Mining And Manufacturing Company | 3-Pyrazolidinone derivatives |
| US4095024A (en) * | 1975-01-31 | 1978-06-13 | Imperial Chemical Industries Limited | Process for the manufacture of 1-aryl-3-carboxypyrazolid-5-ones |
| US4550119A (en) * | 1983-05-23 | 1985-10-29 | Warner-Lambert Company | 2,4-Dihydro-5-[(substituted)phenyl]-4,4-disubstituted-3H-pyrazol-3-ones |
| US4551538A (en) * | 1984-12-20 | 1985-11-05 | American Home Products Corporation | Phenylpyrazolidine acetic acid derivatives |
| US5089515A (en) * | 1986-11-20 | 1992-02-18 | Mitsubishi Kasei Corporation | Lipid-peroxide formation inhibiting composition and novel compounds useful therefor |
| CN101333191B (zh) * | 2008-07-25 | 2013-04-03 | 浙江师范大学 | 一种2,5-二取代吡唑啉-3-酮类衍生物的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL286908A (xx) | |
| DE1445931A1 (de) | 1969-02-13 |
| GB985653A (en) | 1965-03-10 |
| GB997033A (en) | 1965-06-30 |
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