NO121342B - - Google Patents
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- Publication number
- NO121342B NO121342B NO0322/68A NO32268A NO121342B NO 121342 B NO121342 B NO 121342B NO 0322/68 A NO0322/68 A NO 0322/68A NO 32268 A NO32268 A NO 32268A NO 121342 B NO121342 B NO 121342B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- phthalazino
- bromomethyl
- nitro
- benzoyl chloride
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 12
- ZSCSUJZQCNTODA-UHFFFAOYSA-N 2-(bromomethyl)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1CBr ZSCSUJZQCNTODA-UHFFFAOYSA-N 0.000 claims description 6
- KCOLJRSQFLZEAB-UHFFFAOYSA-N 3,4-dihydro-2h-phthalazin-1-one Chemical compound C1=CC=C2C(=O)NNCC2=C1 KCOLJRSQFLZEAB-UHFFFAOYSA-N 0.000 claims description 6
- ZLHNYIHIHQEHJQ-UHFFFAOYSA-N N,N'-Diacetylhydrazine Chemical compound CC(=O)NNC(C)=O ZLHNYIHIHQEHJQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- CXSJGNHRBWJXEA-UHFFFAOYSA-N 5,12-dihydrophthalazino[3,2-b]phthalazine-7,14-dione Chemical class C1C2=CC=CC=C2C(=O)N2N1C(=O)C1=CC=CC=C1C2 CXSJGNHRBWJXEA-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- -1 amino compound Chemical class 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- FACXGJANFZCRTJ-UHFFFAOYSA-N 2,3-diacetyl-4H-phthalazin-1-one Chemical compound C(C)(=O)N1C(C2=CC=CC=C2CN1C(C)=O)=O FACXGJANFZCRTJ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- CLPDGZLMLHDCOY-UHFFFAOYSA-N n-(3-oxo-1h-2-benzofuran-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2COC(=O)C2=C1 CLPDGZLMLHDCOY-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 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
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VJQUJFBMLKJQIY-UHFFFAOYSA-N 2-(bromomethyl)-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1CBr VJQUJFBMLKJQIY-UHFFFAOYSA-N 0.000 description 1
- IRLIEBWRMLYJQL-UHFFFAOYSA-N 2-(bromomethyl)-5-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CBr)C(C(Cl)=O)=C1 IRLIEBWRMLYJQL-UHFFFAOYSA-N 0.000 description 1
- ZIJZDNKZJZUROE-UHFFFAOYSA-N 6-amino-3h-2-benzofuran-1-one Chemical compound NC1=CC=C2COC(=O)C2=C1 ZIJZDNKZJZUROE-UHFFFAOYSA-N 0.000 description 1
- RNWGZXAHUPFXLL-UHFFFAOYSA-N 6-nitro-3h-2-benzofuran-1-one Chemical compound [O-][N+](=O)C1=CC=C2COC(=O)C2=C1 RNWGZXAHUPFXLL-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4842/67A GB1199482A (en) | 1967-02-01 | 1967-02-01 | Novel-Phthalazino [2,3-b] Pthalazine Derivatives, the preparation thereof and Compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121342B true NO121342B (fr) | 1971-02-15 |
Family
ID=9784823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO0322/68A NO121342B (fr) | 1967-02-01 | 1968-01-25 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3557108A (fr) |
| AT (1) | AT275530B (fr) |
| BE (1) | BE710210A (fr) |
| CH (1) | CH484153A (fr) |
| DE (1) | DE1695381B2 (fr) |
| DK (1) | DK117568B (fr) |
| ES (1) | ES350001A0 (fr) |
| FI (1) | FI47664C (fr) |
| FR (2) | FR1583197A (fr) |
| GB (1) | GB1199482A (fr) |
| IL (1) | IL29345A (fr) |
| NL (1) | NL6800912A (fr) |
| NO (1) | NO121342B (fr) |
| SE (1) | SE335348B (fr) |
| YU (1) | YU31941B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1289189A (fr) * | 1970-01-27 | 1972-09-13 | ||
| GB1412527A (en) * | 1973-04-27 | 1975-11-05 | Lepetit Spa | Method for the preparation of phthalqzino o2,3-b phthalazine-5 14h, 12 7h-dione |
-
1967
- 1967-02-01 GB GB4842/67A patent/GB1199482A/en not_active Expired
-
1968
- 1968-01-16 US US698139A patent/US3557108A/en not_active Expired - Lifetime
- 1968-01-18 IL IL29345A patent/IL29345A/en unknown
- 1968-01-19 NL NL6800912A patent/NL6800912A/xx unknown
- 1968-01-22 FI FI680167A patent/FI47664C/fi active
- 1968-01-24 DK DK26668AA patent/DK117568B/da unknown
- 1968-01-25 NO NO0322/68A patent/NO121342B/no unknown
- 1968-01-27 DE DE19681695381 patent/DE1695381B2/de active Granted
- 1968-01-30 FR FR1583197D patent/FR1583197A/fr not_active Expired
- 1968-01-31 CH CH145068A patent/CH484153A/fr not_active IP Right Cessation
- 1968-01-31 SE SE01305/68A patent/SE335348B/xx unknown
- 1968-01-31 AT AT96168A patent/AT275530B/de active
- 1968-01-31 ES ES350001A patent/ES350001A0/es active Pending
- 1968-02-01 BE BE710210D patent/BE710210A/xx unknown
- 1968-02-01 YU YU0239/68A patent/YU31941B/xx unknown
- 1968-04-29 FR FR149898A patent/FR7422M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1583197A (fr) | 1969-10-24 |
| ES350001A0 (es) | 1969-04-16 |
| GB1199482A (en) | 1970-07-22 |
| FI47664B (fr) | 1973-10-31 |
| IL29345A (en) | 1971-07-28 |
| NL6800912A (fr) | 1968-08-02 |
| BE710210A (fr) | 1968-06-17 |
| FI47664C (fi) | 1974-02-11 |
| YU23968A (en) | 1973-08-31 |
| AT275530B (de) | 1969-10-27 |
| DE1695381C3 (fr) | 1973-10-11 |
| DE1695381B2 (de) | 1973-03-08 |
| SE335348B (fr) | 1971-05-24 |
| FR7422M (fr) | 1969-11-12 |
| DK117568B (da) | 1970-05-11 |
| DE1695381A1 (de) | 1972-04-06 |
| YU31941B (en) | 1974-02-28 |
| CH484153A (fr) | 1970-01-15 |
| US3557108A (en) | 1971-01-19 |
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