NO129298B - - Google Patents
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- Publication number
- NO129298B NO129298B NO03799/70*[A NO379970A NO129298B NO 129298 B NO129298 B NO 129298B NO 379970 A NO379970 A NO 379970A NO 129298 B NO129298 B NO 129298B
- Authority
- NO
- Norway
- Prior art keywords
- pyrazolo
- phthalazine
- dione
- phenyl
- acyl
- Prior art date
Links
- -1 halo-lower-alkyl Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 150000001263 acyl chlorides Chemical class 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052760 oxygen Chemical group 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000155 melt Substances 0.000 description 5
- KCOLJRSQFLZEAB-UHFFFAOYSA-N 3,4-dihydro-2h-phthalazin-1-one Chemical compound C1=CC=C2C(=O)NNCC2=C1 KCOLJRSQFLZEAB-UHFFFAOYSA-N 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HIIJDRFUBFGPPU-UHFFFAOYSA-N pyrazolo[4,3-f]phthalazin-1-one Chemical class C1(N=NC=2C=CC=3C=NN=CC3C21)=O HIIJDRFUBFGPPU-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QDESIROZCLVZHE-UHFFFAOYSA-N 3-(diethylamino)-2-methyl-10H-pyrazolo[1,2-b]phthalazine-1,5-dione Chemical compound CC1=C(N2N(CC3=CC=CC=C3C2=O)C1=O)N(CC)CC QDESIROZCLVZHE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PWYRMTCDRYCZAB-UHFFFAOYSA-N 2-acetyl-3-(diethylamino)-10H-pyrazolo[1,2-b]phthalazine-1,5-dione Chemical compound C(C)(=O)C1=C(N2N(CC3=CC=CC=C3C2=O)C1=O)N(CC)CC PWYRMTCDRYCZAB-UHFFFAOYSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2388569 | 1969-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129298B true NO129298B (ro) | 1974-03-25 |
Family
ID=11210636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO03799/70*[A NO129298B (ro) | 1969-10-27 | 1970-10-08 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS4911400B1 (ro) |
| AT (1) | AT299192B (ro) |
| BE (1) | BE757053A (ro) |
| BR (1) | BR6915003D0 (ro) |
| CA (1) | CA978528A (ro) |
| CH (1) | CH525225A (ro) |
| DK (1) | DK125473B (ro) |
| FI (1) | FI50530C (ro) |
| FR (1) | FR2070168B1 (ro) |
| GB (1) | GB1265617A (ro) |
| IL (1) | IL35307A (ro) |
| NL (1) | NL141876B (ro) |
| NO (1) | NO129298B (ro) |
| PL (1) | PL81126B1 (ro) |
| RO (2) | RO58872A (ro) |
| SE (1) | SE385894B (ro) |
| SU (1) | SU375848A3 (ro) |
| ZA (1) | ZA706248B (ro) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL139974B (nl) * | 1969-03-05 | 1973-10-15 | Lepetit Spa | Werkwijze voor de bereiding van ftalazinederivaten met ontsteking tegengaande werking, werkwijze voor de bereiding van therapeutische preparaten die deze bevatten, alsmede gevormde therapeutische preparaten verkregen volgens deze werkwijze. |
-
0
- BE BE757053D patent/BE757053A/xx unknown
-
1969
- 1969-12-11 BR BR215003/69A patent/BR6915003D0/pt unknown
-
1970
- 1970-09-14 ZA ZA706248A patent/ZA706248B/xx unknown
- 1970-09-17 GB GB1265617D patent/GB1265617A/en not_active Expired
- 1970-09-17 IL IL35307A patent/IL35307A/xx unknown
- 1970-09-30 PL PL1970143586A patent/PL81126B1/pl unknown
- 1970-10-07 JP JP45087579A patent/JPS4911400B1/ja active Pending
- 1970-10-08 NO NO03799/70*[A patent/NO129298B/no unknown
- 1970-10-15 CA CA095,663A patent/CA978528A/en not_active Expired
- 1970-10-20 NL NL707015333A patent/NL141876B/xx unknown
- 1970-10-23 FI FI702855A patent/FI50530C/fi active
- 1970-10-26 RO RO74572A patent/RO58872A/ro unknown
- 1970-10-26 RO RO64790A patent/RO58992A/ro unknown
- 1970-10-26 CH CH1578770A patent/CH525225A/fr not_active IP Right Cessation
- 1970-10-26 SU SU1489443A patent/SU375848A3/ru active
- 1970-10-26 DK DK543270AA patent/DK125473B/da unknown
- 1970-10-27 FR FR707038762A patent/FR2070168B1/fr not_active Expired
- 1970-10-27 SE SE7014481A patent/SE385894B/xx unknown
- 1970-10-27 AT AT964770A patent/AT299192B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL141876B (nl) | 1974-04-16 |
| FI50530C (fi) | 1976-04-12 |
| ZA706248B (en) | 1971-05-27 |
| DE2051800B2 (de) | 1976-07-01 |
| FR2070168B1 (ro) | 1973-08-10 |
| BE757053A (fr) | 1971-03-16 |
| GB1265617A (ro) | 1972-03-01 |
| BR6915003D0 (pt) | 1973-05-24 |
| SE385894B (sv) | 1976-07-26 |
| IL35307A (en) | 1974-01-14 |
| SU375848A3 (ro) | 1973-03-23 |
| IL35307A0 (en) | 1970-11-30 |
| FR2070168A1 (ro) | 1971-09-10 |
| FI50530B (ro) | 1975-12-31 |
| RO58872A (ro) | 1976-10-15 |
| RO58992A (ro) | 1975-10-15 |
| DK125473B (da) | 1973-02-26 |
| AT299192B (de) | 1972-06-12 |
| CA978528A (en) | 1975-11-25 |
| CH525225A (fr) | 1972-07-15 |
| PL81126B1 (ro) | 1975-08-30 |
| NL7015333A (ro) | 1971-04-29 |
| JPS4911400B1 (ro) | 1974-03-16 |
| DE2051800A1 (de) | 1971-06-09 |
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