DE1695314A1 - Verfahren zur Herstellung von 1-Phenyl-2,3-dimethyl-4-(2-Bicyclo-[2,2,1]heptyl)-amino-3-pyrazolon-5-on - Google Patents
Verfahren zur Herstellung von 1-Phenyl-2,3-dimethyl-4-(2-Bicyclo-[2,2,1]heptyl)-amino-3-pyrazolon-5-onInfo
- Publication number
- DE1695314A1 DE1695314A1 DE19671695314 DE1695314A DE1695314A1 DE 1695314 A1 DE1695314 A1 DE 1695314A1 DE 19671695314 DE19671695314 DE 19671695314 DE 1695314 A DE1695314 A DE 1695314A DE 1695314 A1 DE1695314 A1 DE 1695314A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- dimethyl
- amino
- bicyclo
- heptyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 2-bicyclo- [2,2,1] heptyl Chemical group 0.000 title description 2
- 230000002829 reductive effect Effects 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000010970 precious metal Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N 1-Pyrroline Chemical compound C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- FQMNVNKBWNEVMK-UHFFFAOYSA-J barium(2+);platinum(2+);disulfate Chemical compound [Ba+2].[Pt+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O FQMNVNKBWNEVMK-UHFFFAOYSA-J 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- UKPBEPCQTDRZSE-UHFFFAOYSA-N cyclizine hydrochloride Chemical compound Cl.C1CN(C)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 UKPBEPCQTDRZSE-UHFFFAOYSA-N 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 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
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B3/00—Ohmic-resistance heating
- H05B3/0004—Devices wherein the heating current flows through the material to be heated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK0062072 | 1967-04-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1695314A1 true DE1695314A1 (de) | 1971-03-18 |
Family
ID=7230412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671695314 Pending DE1695314A1 (de) | 1967-04-22 | 1967-04-22 | Verfahren zur Herstellung von 1-Phenyl-2,3-dimethyl-4-(2-Bicyclo-[2,2,1]heptyl)-amino-3-pyrazolon-5-on |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE713366A (cs) |
| CH (1) | CH487162A (cs) |
| DE (1) | DE1695314A1 (cs) |
| ES (1) | ES353584A1 (cs) |
| FR (1) | FR7416M (cs) |
| GB (1) | GB1155010A (cs) |
| IL (1) | IL29750A (cs) |
| NL (1) | NL6805391A (cs) |
-
1967
- 1967-04-22 DE DE19671695314 patent/DE1695314A1/de active Pending
-
1968
- 1968-04-03 CH CH488868A patent/CH487162A/de not_active IP Right Cessation
- 1968-04-03 IL IL29750A patent/IL29750A/en unknown
- 1968-04-08 BE BE713366D patent/BE713366A/xx unknown
- 1968-04-17 NL NL6805391A patent/NL6805391A/xx unknown
- 1968-04-18 GB GB08285/68A patent/GB1155010A/en not_active Expired
- 1968-04-22 ES ES353584A patent/ES353584A1/es not_active Expired
- 1968-04-22 FR FR148948A patent/FR7416M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH487162A (de) | 1970-03-15 |
| NL6805391A (cs) | 1968-10-23 |
| BE713366A (cs) | 1968-10-08 |
| IL29750A0 (en) | 1968-06-20 |
| FR7416M (cs) | 1969-11-12 |
| IL29750A (en) | 1971-11-29 |
| GB1155010A (en) | 1969-06-11 |
| ES353584A1 (es) | 1969-10-01 |
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