US3293261A - 1-isopropyl-3-phenyl-5-aminopyrazole - Google Patents
1-isopropyl-3-phenyl-5-aminopyrazole Download PDFInfo
- Publication number
- US3293261A US3293261A US380681A US38068164A US3293261A US 3293261 A US3293261 A US 3293261A US 380681 A US380681 A US 380681A US 38068164 A US38068164 A US 38068164A US 3293261 A US3293261 A US 3293261A
- Authority
- US
- United States
- Prior art keywords
- aminopyrazole
- isopropyl
- phenyl
- ethanol
- compounds
- 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
- BCLGGAULDBHZDU-UHFFFAOYSA-N 5-phenyl-2-propan-2-ylpyrazol-3-amine Chemical compound C1=C(N)N(C(C)C)N=C1C1=CC=CC=C1 BCLGGAULDBHZDU-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- ZJRCIQAMTAINCB-UHFFFAOYSA-N benzoylacetonitrile Chemical compound N#CCC(=O)C1=CC=CC=C1 ZJRCIQAMTAINCB-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
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D231/38—Nitrogen atoms
Definitions
- These new pyrazole compounds possess pharmocological activity being particularly distinguished by their ability to produce skeletal muscle relaxation upon administration to animals. Thus they are useful as muscle relaxants.
- the compounds of Formula I are readily produced. They may :be simply prepared by bringing together benzoylacetonitrile and the appropriate hydrazine, preferably in the presence of a solvent.
- An illustrative reaction scheme is:
- R has the significance aforestated.
- nitrile and the hydrazine are placed in an inert reaction solvent such as ethanol and the mixture preferably subjected to the influence of heat. Upon completion of the reaction the mixture is cooled and the precipitated solid recovered in conventional fashion. Recrystallization of the obtained product may be efiected in the usual manner. Suitable recrystallization media are the lower alkanols such as ethanol and methanol.
- the compounds of this invention are readily formulated in a variety of pharmaceutical forms of the solid or liquid type using excipients and adjuvants with which incompatability is absent.
- Exemplary solid forms consist of magnesium stearate, sucrose, talc, stearic acid, agar pectin or acacia which may take the shape of tablets or powders.
- Exemplary liquid forms consist of peanut oil, olive oil, sesame oil and water. The liquid forms may be dispensed in capsules or as suspensions. In the case of veterinary application, the compounds may be placed in the feed or drinking water of animals.
- the material may be recrystallized again from methanol to yield 60 g., M.P. 95.5-96 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
United States Eatent 6 "ice 3,293,261 I-ISOPROPYL-3-PI-ENYL-5-AM1NOPYRAZOLE Harry R. Snyder, Jrx, Norwich, N.Y., assignor to The Norwich Pharmacal Company, Norwich, N.Y., a corporation of New York No Drawing. Filed July 6, 1964, Ser. No. 380,681 1 Claim. (Cl. 260-310) This invention relates to pyrazole compounds, particularly those of the formula:
U-C 8H5 HzNiN N wherein R is a isopropyl or 2-hydroxyethyl group.
These new pyrazole compounds possess pharmocological activity being particularly distinguished by their ability to produce skeletal muscle relaxation upon administration to animals. Thus they are useful as muscle relaxants.
The compounds of Formula I are readily produced. They may :be simply prepared by bringing together benzoylacetonitrile and the appropriate hydrazine, preferably in the presence of a solvent. An illustrative reaction scheme is:
wherein R has the significance aforestated.
In carrying out the reaction the nitrile and the hydrazine are placed in an inert reaction solvent such as ethanol and the mixture preferably subjected to the influence of heat. Upon completion of the reaction the mixture is cooled and the precipitated solid recovered in conventional fashion. Recrystallization of the obtained product may be efiected in the usual manner. Suitable recrystallization media are the lower alkanols such as ethanol and methanol.
The compounds of this invention are readily formulated in a variety of pharmaceutical forms of the solid or liquid type using excipients and adjuvants with which incompatability is absent. Exemplary solid forms consist of magnesium stearate, sucrose, talc, stearic acid, agar pectin or acacia which may take the shape of tablets or powders. Exemplary liquid forms consist of peanut oil, olive oil, sesame oil and water. The liquid forms may be dispensed in capsules or as suspensions. In the case of veterinary application, the compounds may be placed in the feed or drinking water of animals.
3 ,293,261 Patented Dec. 20, 1966 In order that this invention may be readily available to and understood by those skilled in the art the following examples are appended:
EXAMPLE I (U-788) 1-is0pr0pyl-3-phenyl-5-aminopyrazole' Benzoylaoetonitrile (94 g., 0.65 mole) and isopropylhydrazine (48 g., 0.65 mole) are placed in a flask together with ethanol. The reaction mixture is refluxed for four hours. The alcohol is removed under reduced pressure to leave a syrupy residue which slowly crystallizes. The crude material is recrystallized from a minimum amount of methanol to yield 78 g. M.P. 93-95" C.
The material may be recrystallized again from methanol to yield 60 g., M.P. 95.5-96 C.
Analysis.Calcd for C H N C, 71.61; H, 7.51; N, 20.88. Found: C, 71.43; H, 7.65
EXAMPLE II (U-768) 1- (2-hydroxyethyl) -3-phenyZ-5-aminopyrazole Benzoylacetonitrile (290 g., 2.0 moles) and 2-hydr0xyethylhydrazine (152 g., 2.0 moles) are placed in a flask together with ethanol (1000 ml.). The mixture is refluxed for four hours, cooled, and filtered to yield 297 g. (73%) of product, M.P. 147.5149.5 C. Evaporation of the filtrate followed by recrystallization of the residue aflords another 28 g. of product; total yield is 325 g. This may be recrystallized from ethanol, M.P. 149150 C.
Analysis for C H N O.Calcd: C, 65.00; H, 6.45; N, 20.68. Found: C, 65.27; H, 6.52; N, 21.11.
What is claimed is:
1-isopr0pyl-3-phenyl-5-aminopyrazole.
7 References Cited by the Examiner UNITED STATES PATENTS 2,987,523 6/1961 Staub 260-4110 2,989,539 6/1961 Anderson 26031O 3,211,743 10/ 1965 Schmidt 2603 10 OTHER REFERENCES Alberti: Gaz. Chim. Italiana, vol. 89, pages 1017-32 (1959).
Searles et al.: Jour. Org. Chem., vol. 19, page 928 (1954 WALTER A. MODANCE, Primary Examiner.
N. TROUSOF, Assistant Examiner.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US380681A US3293261A (en) | 1964-07-06 | 1964-07-06 | 1-isopropyl-3-phenyl-5-aminopyrazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US380681A US3293261A (en) | 1964-07-06 | 1964-07-06 | 1-isopropyl-3-phenyl-5-aminopyrazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3293261A true US3293261A (en) | 1966-12-20 |
Family
ID=23502081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US380681A Expired - Lifetime US3293261A (en) | 1964-07-06 | 1964-07-06 | 1-isopropyl-3-phenyl-5-aminopyrazole |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3293261A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008056A1 (en) * | 1978-08-10 | 1980-02-20 | Bayer Ag | N-substituted pyrazole derivatives, process for their preparation and N-hydroxyalkylpyrazoles obtained in the course of this process |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2987523A (en) * | 1961-06-06 | Process for the production of j-methyl- | ||
| US2989539A (en) * | 1961-06-20 | J-amino-x-phenylpyrazoles and method | ||
| US3211743A (en) * | 1965-10-12 | Chj-chs-oh |
-
1964
- 1964-07-06 US US380681A patent/US3293261A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2987523A (en) * | 1961-06-06 | Process for the production of j-methyl- | ||
| US2989539A (en) * | 1961-06-20 | J-amino-x-phenylpyrazoles and method | ||
| US3211743A (en) * | 1965-10-12 | Chj-chs-oh |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008056A1 (en) * | 1978-08-10 | 1980-02-20 | Bayer Ag | N-substituted pyrazole derivatives, process for their preparation and N-hydroxyalkylpyrazoles obtained in the course of this process |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2108438C2 (en) | 4-(4-Methoxy-benzyl)-imidazolidin-2-one | |
| US3254093A (en) | Process for preparing pyrazoles | |
| US3318905A (en) | 1-substituted 3-dialkylaminoalkoxy-in-dazoles and 1-substituted-3-hydroxyindazoles | |
| DE2654665A1 (en) | 1-ARYL-2- (1-IMIDAZOLYL) -ALKYLSULFIDE, THE METHOD FOR THEIR MANUFACTURE AND THEIR USE IN MEDICINAL PRODUCTS | |
| US3293261A (en) | 1-isopropyl-3-phenyl-5-aminopyrazole | |
| CH511867A (en) | Hypotensive n-pyrazinoyl-ethyl-piperazines | |
| US3364227A (en) | Polymethylenepyrazoles | |
| CH441366A (en) | Process for the preparation of substituted hydrazine compounds | |
| Van den Bos et al. | Investigations on pesticidal phosphorus compounds I. Fungicides, insecticides and acaricides derived from 3‐amino‐1, 2, 4‐triazole | |
| US3663564A (en) | Urazoles and their production | |
| JPH03246282A (en) | Triazolyl hydrazide derivative, method for producing the same, pharmaceutical composition for anti-angina or prevention of gastric ulcer containing the derivative as an active ingredient, and method for producing the same | |
| US2483381A (en) | Beta-dihydro-inylamine and the acid addition salts thereof | |
| US3158599A (en) | Nu-(arylcarbamoyl)- and nu-(arylthiocarbamoyl)-glucosamines | |
| US2618658A (en) | 2,2-dimethyl-3-hydroxypropylamine and process for its preparation | |
| EP0589491A1 (en) | Butenoic acid derivatives | |
| US3154543A (en) | Preparation of 5-aminofurans | |
| US3060192A (en) | Production of enantiomers of alphamethyl-phenethyl hydrazine and intermediate | |
| US2970159A (en) | Hydrazine derivatives | |
| US2855400A (en) | 2-methyl-pyridine-4-carboxylic acid derivatives | |
| US3062881A (en) | 1-(cycloalkanoyl)- and 1-(tri-alkyl-acetyl)-2, 2-(di-substituted)-hydrazine compounds | |
| US3232956A (en) | N-substituted-5-nitro-2-furamidines | |
| AT256114B (en) | Process for the preparation of new benzodiazepine derivatives | |
| US2704754A (en) | Pharmaceuticals | |
| US3072726A (en) | N1-cycloalkanoyl and n1-[alpha-tri-alkyl]-alkanoyl-hydrazides and derivatives thereof | |
| US3121113A (en) | 1-benzyloxy-3-acyl-ureas |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: NORWICH EATON PHARMACEUTICALS, INC., 17 EATON AVE. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:MORTON-NORWICH PRODUCTS, INC., A CORP. OF DE;REEL/FRAME:004085/0126 Effective date: 19820609 |