DE2010040A1 - Phthalazinderivate und Verfahren zu ihrer Herstellung - Google Patents
Phthalazinderivate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2010040A1 DE2010040A1 DE19702010040 DE2010040A DE2010040A1 DE 2010040 A1 DE2010040 A1 DE 2010040A1 DE 19702010040 DE19702010040 DE 19702010040 DE 2010040 A DE2010040 A DE 2010040A DE 2010040 A1 DE2010040 A1 DE 2010040A1
- Authority
- DE
- Germany
- Prior art keywords
- dione
- dihydro
- phthalazine
- hydrogen
- phenyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 19
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 20
- -1 alkyl radical Chemical class 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 150000001263 acyl chlorides Chemical class 0.000 claims description 4
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001477 organic nitrogen group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- PKOSFWBEGLOCNY-UHFFFAOYSA-N 3-methyl-3-phenyl-1,2-dihydropyrazole Chemical compound C=1C=CC=CC=1C1(C)NNC=C1 PKOSFWBEGLOCNY-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- KCOLJRSQFLZEAB-UHFFFAOYSA-N 3,4-dihydro-2h-phthalazin-1-one Chemical compound C1=CC=C2C(=O)NNCC2=C1 KCOLJRSQFLZEAB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 2
- ZSCSUJZQCNTODA-UHFFFAOYSA-N 2-(bromomethyl)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1CBr ZSCSUJZQCNTODA-UHFFFAOYSA-N 0.000 description 2
- AKGCIXHOZCUKPI-UHFFFAOYSA-N 2-butyl-1,3-dihydropyrazole Chemical compound CCCCN1CC=CN1 AKGCIXHOZCUKPI-UHFFFAOYSA-N 0.000 description 2
- JFJWVJAVVIQZRT-UHFFFAOYSA-N 2-phenyl-1,3-dihydropyrazole Chemical compound C1C=CNN1C1=CC=CC=C1 JFJWVJAVVIQZRT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- NFKAWBGFIMBUMB-UHFFFAOYSA-N 1-phenylpentan-2-one Chemical compound CCCC(=O)CC1=CC=CC=C1 NFKAWBGFIMBUMB-UHFFFAOYSA-N 0.000 description 1
- XYCPCNPKYFWBHZ-UHFFFAOYSA-N 2-(bromomethyl)-2-phenylhexanoyl chloride Chemical compound BrCC(C(=O)Cl)(C1=CC=CC=C1)CCCC XYCPCNPKYFWBHZ-UHFFFAOYSA-N 0.000 description 1
- JIHPRHKSKPWDHL-UHFFFAOYSA-N 2-(bromomethyl)hexanoyl chloride Chemical compound BrCC(C(=O)Cl)CCCC JIHPRHKSKPWDHL-UHFFFAOYSA-N 0.000 description 1
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
- WHLQWRYLRFHDLG-UHFFFAOYSA-N 3,4-dihydropyridazine Chemical compound C1CN=NC=C1 WHLQWRYLRFHDLG-UHFFFAOYSA-N 0.000 description 1
- KGBYMMNGCFTHHV-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2,3-dihydro-1H-pyrazole Chemical compound COC1=CC=C(C=C1)C1C=CNN1 KGBYMMNGCFTHHV-UHFFFAOYSA-N 0.000 description 1
- HLQATVNBENMQCZ-UHFFFAOYSA-N 3-bromo-2-phenylpropanoyl chloride Chemical compound ClC(=O)C(CBr)C1=CC=CC=C1 HLQATVNBENMQCZ-UHFFFAOYSA-N 0.000 description 1
- IHBVNSPHKMCPST-UHFFFAOYSA-N 3-bromopropanoyl chloride Chemical compound ClC(=O)CCBr IHBVNSPHKMCPST-UHFFFAOYSA-N 0.000 description 1
- QYGRKSUICHLREH-UHFFFAOYSA-N 3-methyl-2,3-dihydro-1h-pyrazole Chemical compound CC1NNC=C1 QYGRKSUICHLREH-UHFFFAOYSA-N 0.000 description 1
- XUAKCLDDDITRQM-UHFFFAOYSA-N 3-methyl-2-phenyl-1,3-dihydropyrazole Chemical compound CC1C=CNN1C1=CC=CC=C1 XUAKCLDDDITRQM-UHFFFAOYSA-N 0.000 description 1
- LRTRXDSAJLSRTG-UHFFFAOYSA-N 4-bromobutanoyl chloride Chemical compound ClC(=O)CCCBr LRTRXDSAJLSRTG-UHFFFAOYSA-N 0.000 description 1
- SZEGYGDHHJMUQY-UHFFFAOYSA-N 4-butyl-1,2-dihydropyrazol-3-one Chemical compound CCCCC1=CNNC1=O SZEGYGDHHJMUQY-UHFFFAOYSA-N 0.000 description 1
- TYWCCQQJFXUKRN-UHFFFAOYSA-N 4-methyl-1,2-dihydropyrazol-3-one Chemical compound CC1=CNNC1=O TYWCCQQJFXUKRN-UHFFFAOYSA-N 0.000 description 1
- NALZICDOTSAOTC-UHFFFAOYSA-N 4-methyl-5-phenylpyrazolidin-3-one Chemical compound N1NC(=O)C(C)C1C1=CC=CC=C1 NALZICDOTSAOTC-UHFFFAOYSA-N 0.000 description 1
- KEZKHFASBRGVMY-UHFFFAOYSA-N 5-(4-methoxyphenyl)pyrazolidin-3-one Chemical compound C1=CC(OC)=CC=C1C1NNC(=O)C1 KEZKHFASBRGVMY-UHFFFAOYSA-N 0.000 description 1
- WYVJDRGXWOXCCH-UHFFFAOYSA-N 5-methylpyrazolidin-3-one Chemical compound CC1CC(=O)NN1 WYVJDRGXWOXCCH-UHFFFAOYSA-N 0.000 description 1
- QSCDISPKCBTNDK-UHFFFAOYSA-N 5-phenylpyrazolidin-3-one Chemical compound N1NC(=O)CC1C1=CC=CC=C1 QSCDISPKCBTNDK-UHFFFAOYSA-N 0.000 description 1
- KWOPYXYNJVELIT-UHFFFAOYSA-N C1(=CC=CC=C1)N1NC=CCC1 Chemical compound C1(=CC=CC=C1)N1NC=CCC1 KWOPYXYNJVELIT-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1366769 | 1969-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2010040A1 true DE2010040A1 (de) | 1970-09-10 |
Family
ID=11144568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702010040 Granted DE2010040A1 (de) | 1969-03-05 | 1970-03-04 | Phthalazinderivate und Verfahren zu ihrer Herstellung |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE746751A (enrdf_load_stackoverflow) |
| DE (1) | DE2010040A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2034667A1 (enrdf_load_stackoverflow) |
| NL (1) | NL139974B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE757053A (fr) * | 1969-10-27 | 1971-03-16 | Lepetit Spa | Derives de phtalazines, leur preparation et leur utilisation |
-
1970
- 1970-02-10 NL NL7001848A patent/NL139974B/xx unknown
- 1970-03-02 BE BE746751D patent/BE746751A/xx unknown
- 1970-03-03 FR FR7007571A patent/FR2034667A1/fr active Granted
- 1970-03-04 DE DE19702010040 patent/DE2010040A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE746751A (fr) | 1970-08-17 |
| NL139974B (nl) | 1973-10-15 |
| NL7001848A (enrdf_load_stackoverflow) | 1970-09-08 |
| FR2034667A1 (en) | 1970-12-11 |
| FR2034667B1 (enrdf_load_stackoverflow) | 1973-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |