SU578869A3 - Способ получени 4-окси-3-нитрокарбостирилов - Google Patents
Способ получени 4-окси-3-нитрокарбостириловInfo
- Publication number
- SU578869A3 SU578869A3 SU7402031653A SU2031653A SU578869A3 SU 578869 A3 SU578869 A3 SU 578869A3 SU 7402031653 A SU7402031653 A SU 7402031653A SU 2031653 A SU2031653 A SU 2031653A SU 578869 A3 SU578869 A3 SU 578869A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydroxy
- found
- acid
- oxy
- nitro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 67
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 33
- 229960000583 acetic acid Drugs 0.000 claims 27
- 239000000203 mixture Substances 0.000 claims 21
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 20
- 229910017604 nitric acid Inorganic materials 0.000 claims 20
- 239000000243 solution Substances 0.000 claims 19
- 239000007787 solid Substances 0.000 claims 18
- 239000000047 product Substances 0.000 claims 17
- 239000000725 suspension Substances 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 15
- -1 araloxy Chemical group 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 12
- 239000012362 glacial acetic acid Substances 0.000 claims 12
- 238000001816 cooling Methods 0.000 claims 11
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
- 238000006396 nitration reaction Methods 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- 239000000126 substance Substances 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 238000001953 recrystallisation Methods 0.000 claims 6
- 150000002431 hydrogen Chemical group 0.000 claims 5
- 150000002828 nitro derivatives Chemical class 0.000 claims 5
- 159000000000 sodium salts Chemical class 0.000 claims 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 4
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- WVMBPWMAQDVZCM-UHFFFAOYSA-N N-methylanthranilic acid Chemical compound CNC1=CC=CC=C1C(O)=O WVMBPWMAQDVZCM-UHFFFAOYSA-N 0.000 claims 3
- 150000001448 anilines Chemical class 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000013078 crystal Substances 0.000 claims 3
- 238000001035 drying Methods 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 239000000706 filtrate Substances 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 3
- 238000010992 reflux Methods 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims 2
- MZVAAWXYMDEDLD-UHFFFAOYSA-N 3-nitro-1h-quinolin-2-one Chemical compound C1=CC=C2C=C([N+]([O-])=O)C(O)=NC2=C1 MZVAAWXYMDEDLD-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000005606 carbostyryl group Chemical group 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 125000005504 styryl group Chemical group 0.000 claims 2
- TZPZMVZGJVYAML-REOHCLBHSA-N (2s)-2-(oxaloamino)propanoic acid Chemical class OC(=O)[C@H](C)NC(=O)C(O)=O TZPZMVZGJVYAML-REOHCLBHSA-N 0.000 claims 1
- RKZDBJLZURXMRV-UHFFFAOYSA-N 1-ethyl-4-hydroxy-3-nitroquinolin-2-one Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C(=O)N(CC)C2=C1 RKZDBJLZURXMRV-UHFFFAOYSA-N 0.000 claims 1
- LVABRAQYWIRWEC-UHFFFAOYSA-N 1-hydroxy-3-nitroquinolin-2-one Chemical compound C1=CC=C2C=C([N+]([O-])=O)C(=O)N(O)C2=C1 LVABRAQYWIRWEC-UHFFFAOYSA-N 0.000 claims 1
- BBEOAXDWSOBKMN-UHFFFAOYSA-N 2-(ethylamino)-5-methylbenzoic acid Chemical compound CCNC1=CC=C(C)C=C1C(O)=O BBEOAXDWSOBKMN-UHFFFAOYSA-N 0.000 claims 1
- SPEGUNZOHLFGCL-UHFFFAOYSA-N 2-(ethylamino)benzoic acid Chemical compound CCNC1=CC=CC=C1C(O)=O SPEGUNZOHLFGCL-UHFFFAOYSA-N 0.000 claims 1
- JAKHLQNEMUMGKP-UHFFFAOYSA-N 3,4-diethylaniline Chemical compound CCC1=CC=C(N)C=C1CC JAKHLQNEMUMGKP-UHFFFAOYSA-N 0.000 claims 1
- SHZUGBYEPDMAPC-UHFFFAOYSA-N 4-hydroxy-3-nitro-1h-quinolin-2-one Chemical compound C1=CC=C2C(=O)C([N+]([O-])=O)=C(O)NC2=C1 SHZUGBYEPDMAPC-UHFFFAOYSA-N 0.000 claims 1
- OXSZQTDCCMODLE-UHFFFAOYSA-N 4-hydroxy-6-methyl-1h-quinolin-2-one Chemical compound N1C(O)=CC(=O)C2=CC(C)=CC=C21 OXSZQTDCCMODLE-UHFFFAOYSA-N 0.000 claims 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- YMZASLVENRUONX-UHFFFAOYSA-N 8-bromo-4-hydroxy-1h-quinolin-2-one Chemical compound C1=CC=C(Br)C2=NC(O)=CC(O)=C21 YMZASLVENRUONX-UHFFFAOYSA-N 0.000 claims 1
- OECNFSGXQMTYMK-UHFFFAOYSA-N 8-chloro-4-hydroxy-1h-quinolin-2-one Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1Cl OECNFSGXQMTYMK-UHFFFAOYSA-N 0.000 claims 1
- LECKIZBROZNBDM-UHFFFAOYSA-N 8-chloro-4-hydroxy-3-nitro-1h-quinolin-2-one Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C(=O)NC2=C1Cl LECKIZBROZNBDM-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 241001585714 Nola Species 0.000 claims 1
- JLNMSNDDYBZCIB-UHFFFAOYSA-N OOOOS Chemical compound OOOOS JLNMSNDDYBZCIB-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 101150110027 Plppr4 gene Proteins 0.000 claims 1
- 101150112740 Srgn gene Proteins 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- KURZCZMGELAPSV-UHFFFAOYSA-N [Br].[I] Chemical compound [Br].[I] KURZCZMGELAPSV-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 230000004071 biological effect Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000013256 coordination polymer Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 239000003517 fume Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 230000000802 nitrating effect Effects 0.000 claims 1
- 238000005121 nitriding Methods 0.000 claims 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229920000137 polyphosphoric acid Polymers 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000012262 resinous product Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000012265 solid product Substances 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000013638 trimer Substances 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2400073A GB1453863A (en) | 1973-05-19 | 1973-05-19 | Pharmaceutical compositions comprising nitrocarbostyrils for the treatment of allergic and immunological hypersensitivity |
| GB2431773 | 1973-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU578869A3 true SU578869A3 (ru) | 1977-10-30 |
Family
ID=26256830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402031653A SU578869A3 (ru) | 1973-05-19 | 1974-05-17 | Способ получени 4-окси-3-нитрокарбостирилов |
Country Status (21)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065457A (en) * | 1973-05-19 | 1977-12-27 | Beecham Group Limited | 4-Hydroxy-3-nitro-carbostyril compounds |
| US4192876A (en) * | 1975-07-23 | 1980-03-11 | Sandoz, Inc. | 4-Hydroxy-3-nitro-quinoline-2(1H)-ones |
| DE2631317A1 (de) * | 1975-07-23 | 1977-02-17 | Sandoz Ag | Organische verbindungen, ihre verwendung und herstellung |
| JPS5919095B2 (ja) * | 1977-06-22 | 1984-05-02 | 大塚製薬株式会社 | キノリン誘導体及びその製造法 |
| JPH0681744B2 (ja) * | 1986-10-06 | 1994-10-19 | 三菱化成株式会社 | ２，４−ジオキシキノリン誘導体の製造方法 |
| US5622965A (en) * | 1993-03-12 | 1997-04-22 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon, Eugene Oregon | 4-hydroxy-3-nitro-1,2-dihydroquinolin-2-ones and the use thereof as excitatory amino acid and glycine receptor antagonists |
-
1973
- 1973-05-19 GB GB2400073A patent/GB1453863A/en not_active Expired
-
1974
- 1974-05-15 IE IE1039/74A patent/IE39269B1/xx unknown
- 1974-05-17 FR FR7417170A patent/FR2229414B1/fr not_active Expired
- 1974-05-17 NL NL7406711A patent/NL7406711A/xx not_active Application Discontinuation
- 1974-05-17 DE DE2424076A patent/DE2424076A1/de active Pending
- 1974-05-17 IL IL44849A patent/IL44849A/xx unknown
- 1974-05-17 SE SE7406631A patent/SE7406631L/xx unknown
- 1974-05-17 SU SU7402031653A patent/SU578869A3/ru active
- 1974-05-17 AT AT409674A patent/AT334373B/de not_active IP Right Cessation
- 1974-05-17 ES ES426427A patent/ES426427A1/es not_active Expired
- 1974-05-17 HU HUBE1198A patent/HU168001B/hu unknown
- 1974-05-17 FI FI1531/74A patent/FI153174A7/fi unknown
- 1974-05-17 DK DK273074AA patent/DK137043B/da unknown
- 1974-05-17 CH CH683674A patent/CH601243A5/xx not_active IP Right Cessation
- 1974-05-17 CA CA200,335A patent/CA1030539A/en not_active Expired
- 1974-05-20 AR AR253837A patent/AR201506A1/es active
- 1974-05-20 PH PH15854A patent/PH10621A/en unknown
- 1974-05-20 DD DD178631A patent/DD112126A5/xx unknown
- 1974-05-20 ZM ZM79/74A patent/ZM7974A1/xx unknown
- 1974-05-20 JP JP49056448A patent/JPS5030884A/ja active Pending
- 1974-06-18 IN IN1344/CAL/74A patent/IN139603B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE39269L (en) | 1974-11-19 |
| PH10621A (en) | 1977-07-19 |
| AU6915874A (en) | 1975-11-20 |
| DK137043C (enrdf_load_stackoverflow) | 1978-06-05 |
| FI153174A7 (enrdf_load_stackoverflow) | 1974-11-20 |
| ATA409674A (de) | 1976-05-15 |
| NL7406711A (enrdf_load_stackoverflow) | 1974-11-21 |
| IL44849A0 (en) | 1974-07-31 |
| CA1030539A (en) | 1978-05-02 |
| SE7406631L (enrdf_load_stackoverflow) | 1974-11-20 |
| FR2229414A1 (enrdf_load_stackoverflow) | 1974-12-13 |
| DK137043B (da) | 1978-01-09 |
| IE39269B1 (en) | 1978-08-30 |
| FR2229414B1 (enrdf_load_stackoverflow) | 1977-11-10 |
| JPS5030884A (enrdf_load_stackoverflow) | 1975-03-27 |
| IN139603B (enrdf_load_stackoverflow) | 1976-07-10 |
| AR201506A1 (es) | 1975-03-21 |
| AT334373B (de) | 1976-01-10 |
| IL44849A (en) | 1978-04-30 |
| HU168001B (enrdf_load_stackoverflow) | 1976-02-28 |
| ES426427A1 (es) | 1976-09-16 |
| GB1453863A (en) | 1976-10-27 |
| DE2424076A1 (de) | 1974-12-05 |
| CH601243A5 (enrdf_load_stackoverflow) | 1978-06-30 |
| ZM7974A1 (en) | 1974-12-20 |
| DD112126A5 (enrdf_load_stackoverflow) | 1975-03-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3700673A (en) | 3-4-dihydrobenzo(b) (1,7)naphthyridin-1(2h)-ones | |
| US3266990A (en) | Derivatives of quinazoline | |
| SU578869A3 (ru) | Способ получени 4-окси-3-нитрокарбостирилов | |
| SU578000A3 (ru) | Способ получени производных 3-нитрокумарина или их солей | |
| SU862820A3 (ru) | Способ получени производных изохинолини | |
| CA1173445A (en) | Quinolone derivatives and their use as pharmaceuticals | |
| Fairfull et al. | 918. Some derivatives of 1: 6-diazapyrene and 4: 5–6: 7-dibenzo-1: 3-diaza cyclo hepta-2: 4: 6-triene | |
| US2149335A (en) | Azo dye intermediates and methods of preparing them | |
| SU589917A3 (ru) | Способ получени производных пиримидина | |
| US2650226A (en) | Furo and thieno quinaldines and process for making same | |
| US2701252A (en) | Isoindolenine compounds | |
| US2389147A (en) | 4' methoxy 5 halogeno diphenylamino 2' carboxyl compound and process for producing the same | |
| SU564809A3 (ru) | Способ получени 6-аза-1,2дигидро-3н-1,4-бензодиазепинов или их солей | |
| Perkin et al. | CCLXXIII.—Derivatives of tetrahydrocarbazole. Part IV | |
| DE2922231C2 (enrdf_load_stackoverflow) | ||
| US1950876A (en) | Thiazoline dye and method of preparing it | |
| SU584782A3 (ru) | Способ получени производных аминоимидазоизохинолина или их солей | |
| SU999967A3 (ru) | Способ получени 6-N-замещенных 6-амино-3-пиридазинилгидразинов или их солей | |
| Reed | 115. Hydroacridones. Synthesis and dehydrogenation | |
| JPH09183913A (ja) | ピロロ〔２，１−ａ〕イソキノリン染料 | |
| SU582766A3 (ru) | Способ получени производных 3-хинолинкарбоновой кислоты или их солей | |
| JPS61178970A (ja) | 新規２−置換された１，４−ベンゾジアゼピンの製法 | |
| HU181054B (en) | Process for producing triptamine derivatives | |
| Pratt et al. | The Preparation of Piperazine. | |
| US2441665A (en) | Diamines |