CH593284A5 - Phthalazino(2,3-b)phthalazine-5,12-dione prepn - from the 5,7,12-trione via 2-(o-carboxybenzyl)1(2H)-phthalazinone - Google Patents
Phthalazino(2,3-b)phthalazine-5,12-dione prepn - from the 5,7,12-trione via 2-(o-carboxybenzyl)1(2H)-phthalazinoneInfo
- Publication number
- CH593284A5 CH593284A5 CH569774A CH569774A CH593284A5 CH 593284 A5 CH593284 A5 CH 593284A5 CH 569774 A CH569774 A CH 569774A CH 569774 A CH569774 A CH 569774A CH 593284 A5 CH593284 A5 CH 593284A5
- Authority
- CH
- Switzerland
- Prior art keywords
- phthalazino
- dione
- phthalazinone
- phthalazine
- carboxybenzyl
- Prior art date
Links
- FJUUIBLJWJPZGM-UHFFFAOYSA-N 2-[(1-oxophthalazin-2-yl)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CN1C(=O)C2=CC=CC=C2C=N1 FJUUIBLJWJPZGM-UHFFFAOYSA-N 0.000 title claims description 10
- 239000002253 acid Substances 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- -1 lower alkanol Substances 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- CXSJGNHRBWJXEA-UHFFFAOYSA-N 5,12-dihydrophthalazino[3,2-b]phthalazine-7,14-dione Chemical compound C1C2=CC=CC=C2C(=O)N2N1C(=O)C1=CC=CC=C1C2 CXSJGNHRBWJXEA-UHFFFAOYSA-N 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910019020 PtO2 Inorganic materials 0.000 claims description 2
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 abstract description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract description 4
- 229910052782 aluminium Inorganic materials 0.000 abstract description 3
- 125000005907 alkyl ester group Chemical group 0.000 abstract description 2
- 229910052718 tin Inorganic materials 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 150000005215 alkyl ethers Chemical class 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000006476 reductive cyclization reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- KCOLJRSQFLZEAB-UHFFFAOYSA-N 3,4-dihydro-2h-phthalazin-1-one Chemical compound C1=CC=C2C(=O)NNCC2=C1 KCOLJRSQFLZEAB-UHFFFAOYSA-N 0.000 description 2
- YUSGMOVDBQKEQO-UHFFFAOYSA-N CCCCOC(C1=C(CN2N=CC3=CC=CC=C3C2=O)C=CC=C1)=O Chemical compound CCCCOC(C1=C(CN2N=CC3=CC=CC=C3C2=O)C=CC=C1)=O YUSGMOVDBQKEQO-UHFFFAOYSA-N 0.000 description 2
- XVECLRZXAWEQBU-UHFFFAOYSA-N CCOC(C1=C(CN2N=CC3=CC=CC=C3C2=O)C=CC=C1)=O Chemical compound CCOC(C1=C(CN2N=CC3=CC=CC=C3C2=O)C=CC=C1)=O XVECLRZXAWEQBU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- NKWOXRUJRCMCBH-UHFFFAOYSA-N 1,3-dihydroisoindol-2-amine Chemical class C1=CC=C2CN(N)CC2=C1 NKWOXRUJRCMCBH-UHFFFAOYSA-N 0.000 description 1
- KGLPWQKSKUVKMJ-UHFFFAOYSA-N 2,3-dihydrophthalazine-1,4-dione Chemical compound C1=CC=C2C(=O)NNC(=O)C2=C1 KGLPWQKSKUVKMJ-UHFFFAOYSA-N 0.000 description 1
- ZSCSUJZQCNTODA-UHFFFAOYSA-N 2-(bromomethyl)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1CBr ZSCSUJZQCNTODA-UHFFFAOYSA-N 0.000 description 1
- GSDIOOSPCUFPSE-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-2h-phthalazin-1-one Chemical class C1C=CC=C2C(=O)NNCC21 GSDIOOSPCUFPSE-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- DRTWNJQJYUBAMQ-UHFFFAOYSA-N phthalazino[2,3-b]phthalazine Chemical compound C1=CC=CC2=CN3N(C=C4C=CC=CC4=C3)C=C12 DRTWNJQJYUBAMQ-UHFFFAOYSA-N 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2020373 | 1973-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH593284A5 true CH593284A5 (en) | 1977-11-30 |
Family
ID=10142140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH569774A CH593284A5 (en) | 1973-04-27 | 1974-04-25 | Phthalazino(2,3-b)phthalazine-5,12-dione prepn - from the 5,7,12-trione via 2-(o-carboxybenzyl)1(2H)-phthalazinone |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5337880B2 (cs) |
| AR (1) | AR206889A1 (cs) |
| CA (1) | CA1016944A (cs) |
| CH (1) | CH593284A5 (cs) |
| CS (1) | CS179916B2 (cs) |
| DD (1) | DD113358A5 (cs) |
| ES (1) | ES425747A1 (cs) |
| HU (1) | HU167319B (cs) |
| NL (1) | NL7405321A (cs) |
| PL (1) | PL88727B1 (cs) |
| SU (1) | SU520916A3 (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025941A1 (de) * | 1979-09-19 | 1981-04-01 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyridazopyridazinderivate, Verfahren zu deren Herstellung und Arzneimittel enthaltend solche Pyridazopyridazinderivate |
-
1974
- 1974-01-01 AR AR25334874A patent/AR206889A1/es active
- 1974-04-19 NL NL7405321A patent/NL7405321A/xx unknown
- 1974-04-25 CH CH569774A patent/CH593284A5/fr not_active IP Right Cessation
- 1974-04-25 PL PL17058774A patent/PL88727B1/pl unknown
- 1974-04-26 JP JP4745374A patent/JPS5337880B2/ja not_active Expired
- 1974-04-26 CS CS301374A patent/CS179916B2/cs unknown
- 1974-04-26 SU SU2018859A patent/SU520916A3/ru active
- 1974-04-26 HU HULE000742 patent/HU167319B/hu unknown
- 1974-04-26 CA CA198,242A patent/CA1016944A/en not_active Expired
- 1974-04-26 DD DD17816174A patent/DD113358A5/xx unknown
- 1974-04-27 ES ES425747A patent/ES425747A1/es not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025941A1 (de) * | 1979-09-19 | 1981-04-01 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyridazopyridazinderivate, Verfahren zu deren Herstellung und Arzneimittel enthaltend solche Pyridazopyridazinderivate |
| US4341781A (en) | 1979-09-19 | 1982-07-27 | Hoffmann-La Roche Inc. | Pyridazopyridazine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5337880B2 (cs) | 1978-10-12 |
| PL88727B1 (cs) | 1976-09-30 |
| DD113358A5 (cs) | 1975-06-05 |
| NL7405321A (cs) | 1974-10-29 |
| ES425747A1 (es) | 1976-06-16 |
| CS179916B2 (en) | 1977-12-30 |
| SU520916A3 (ru) | 1976-07-05 |
| AR206889A1 (es) | 1976-08-31 |
| HU167319B (cs) | 1975-09-27 |
| JPS5013398A (cs) | 1975-02-12 |
| CA1016944A (en) | 1977-09-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |