CH437340A - Procédé de préparation de l'acide N-(2,3-diméthylphényl)-anthranilique - Google Patents
Procédé de préparation de l'acide N-(2,3-diméthylphényl)-anthraniliqueInfo
- Publication number
- CH437340A CH437340A CH541263A CH541263A CH437340A CH 437340 A CH437340 A CH 437340A CH 541263 A CH541263 A CH 541263A CH 541263 A CH541263 A CH 541263A CH 437340 A CH437340 A CH 437340A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- phenyl
- acid
- mixture
- water
- Prior art date
Links
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 7
- -1 2, 3-dimethyl phenyl Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- 239000000203 mixture Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- FMKFZGUOVGWMSZ-UHFFFAOYSA-N 1,3-bis(2,3-dimethylphenyl)quinazoline-2,4-dione Chemical compound CC1=C(C=CC=C1C)N1C(N(C(C2=CC=CC=C12)=O)C1=C(C(=CC=C1)C)C)=O FMKFZGUOVGWMSZ-UHFFFAOYSA-N 0.000 description 2
- OPDUMRSBESYOCQ-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)-3,1-benzoxazine-2,4-dione Chemical compound CC1=CC=CC(N2C(OC(=O)C3=CC=CC=C32)=O)=C1C OPDUMRSBESYOCQ-UHFFFAOYSA-N 0.000 description 2
- DVOJLELFMOKLKC-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)indole-2,3-dione Chemical compound CC1=CC=CC(N2C3=CC=CC=C3C(=O)C2=O)=C1C DVOJLELFMOKLKC-UHFFFAOYSA-N 0.000 description 2
- AGYCCJAMVLQWDU-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)quinazoline-2,4-dione Chemical compound CC1=CC=CC(N2C(NC(=O)C3=CC=CC=C32)=O)=C1C AGYCCJAMVLQWDU-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DUQDEEVOZDZJGQ-UHFFFAOYSA-N (2,3-dimethylphenyl)azanium;chloride Chemical compound Cl.CC1=CC=CC(N)=C1C DUQDEEVOZDZJGQ-UHFFFAOYSA-N 0.000 description 1
- VQTDSHRCXQARNR-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)-2,4-dihydro-3,1-benzoxazine Chemical compound CC1=C(C=CC=C1C)N1COCC2=C1C=CC=C2 VQTDSHRCXQARNR-UHFFFAOYSA-N 0.000 description 1
- YYVGQADTDYBHHR-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)-2h-3,1-benzoxazin-4-one Chemical compound CC1=CC=CC(N2C3=CC=CC=C3C(=O)OC2)=C1C YYVGQADTDYBHHR-UHFFFAOYSA-N 0.000 description 1
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 1
- AIBJYJJPJNCJFE-UHFFFAOYSA-N 2-(2,3-dimethylphenoxy)-4-methylquinoline Chemical compound CC1=C(OC2=NC3=CC=CC=C3C(=C2)C)C=CC=C1C AIBJYJJPJNCJFE-UHFFFAOYSA-N 0.000 description 1
- FLMBKYGDNISFJD-UHFFFAOYSA-N 2-(2,3-dimethylphenoxy)-4-phenoxyquinazoline Chemical compound O(C1=CC=CC=C1)C1=NC(=NC2=CC=CC=C12)OC1=C(C(=CC=C1)C)C FLMBKYGDNISFJD-UHFFFAOYSA-N 0.000 description 1
- PFEIMKNQOIFKSW-UHFFFAOYSA-N 2-chloro-4-methylquinoline Chemical compound C1=CC=C2C(C)=CC(Cl)=NC2=C1 PFEIMKNQOIFKSW-UHFFFAOYSA-N 0.000 description 1
- ZAXXHUNCROLIFL-UHFFFAOYSA-N 2-chloro-4-phenoxyquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1OC1=CC=CC=C1 ZAXXHUNCROLIFL-UHFFFAOYSA-N 0.000 description 1
- RJJVRQMAZPAELO-UHFFFAOYSA-N 6,12-bis(2,3-dimethylphenoxy)benzo[c][1,5]benzodiazocine Chemical compound CC1=C(OC2=C3C(=NC(=C4C(=N2)C=CC=C4)OC2=C(C(=CC=C2)C)C)C=CC=C3)C=CC=C1C RJJVRQMAZPAELO-UHFFFAOYSA-N 0.000 description 1
- OJTMDSOQFLNSHQ-UHFFFAOYSA-N 8,9-diazatricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,8,10,12,14-octaene Chemical compound C1=CN=NC2=CC=CC=C2C2=CC=CC=C21 OJTMDSOQFLNSHQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 240000008100 Brassica rapa Species 0.000 description 1
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- RQELNTXXDLIOOL-UHFFFAOYSA-N CC1=C(OC2=NC3=CC=CC=C3C(=N2)OC2=C(C(=CC=C2)C)C)C=CC=C1C Chemical compound CC1=C(OC2=NC3=CC=CC=C3C(=N2)OC2=C(C(=CC=C2)C)C)C=CC=C1C RQELNTXXDLIOOL-UHFFFAOYSA-N 0.000 description 1
- XTZPGZMURPMMEL-UHFFFAOYSA-N CC1=CC=CC(N(C2=CC=CC=C2C(N2C)=O)C2=O)=C1C Chemical compound CC1=CC=CC(N(C2=CC=CC=C2C(N2C)=O)C2=O)=C1C XTZPGZMURPMMEL-UHFFFAOYSA-N 0.000 description 1
- RSULNTCAMCCGTC-UHFFFAOYSA-N CN1C(=NC2=CC=CC=C2C1=O)OC1=C(C(=CC=C1)C)C Chemical compound CN1C(=NC2=CC=CC=C2C1=O)OC1=C(C(=CC=C1)C)C RSULNTCAMCCGTC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 229940097789 heavy mineral oil Drugs 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 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
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA858228 | 1962-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH437340A true CH437340A (fr) | 1967-06-15 |
Family
ID=4141560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH541263A CH437340A (fr) | 1962-09-18 | 1963-04-30 | Procédé de préparation de l'acide N-(2,3-diméthylphényl)-anthranilique |
Country Status (6)
| Country | Link |
|---|---|
| BR (1) | BR6348807D0 (OSRAM) |
| CH (1) | CH437340A (OSRAM) |
| DE (1) | DE1190951B (OSRAM) |
| ES (1) | ES287547A1 (OSRAM) |
| FR (1) | FR1572121A (OSRAM) |
| NL (1) | NL292083A (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10161767A1 (de) * | 2001-12-15 | 2003-06-26 | Merck Patent Gmbh | 2-Guanidino-4-heterocyclyl-chinazoline |
| CL2004000409A1 (es) * | 2003-03-03 | 2005-01-07 | Vertex Pharma | Compuestos derivados de 2-(cilo sustituido)-1-(amino u oxi sustituido)-quinazolina, inhibidores de canales ionicos de sodio y calcio dependientes de voltaje; composicion farmaceutica; y uso del compuesto en el tratamiento de dolor agudo, cronico, neu |
| CN102786512A (zh) * | 2012-05-31 | 2012-11-21 | 中国人民解放军军事医学科学院毒物药物研究所 | N-芳基不饱和稠环叔胺类化合物及其制备方法和抗肿瘤应用 |
-
0
- NL NL292083D patent/NL292083A/xx unknown
-
1963
- 1963-04-30 BR BR14880763A patent/BR6348807D0/pt unknown
- 1963-04-30 CH CH541263A patent/CH437340A/fr unknown
- 1963-04-30 ES ES287547A patent/ES287547A1/es not_active Expired
- 1963-04-30 FR FR1572121D patent/FR1572121A/fr not_active Expired
- 1963-04-30 DE DEP31707A patent/DE1190951B/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1190951B (de) | 1965-04-15 |
| BR6348807D0 (pt) | 1973-07-19 |
| ES287547A1 (es) | 1963-06-16 |
| NL292083A (OSRAM) | |
| FR1572121A (OSRAM) | 1969-06-27 |
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| CH639369A5 (fr) | Benzamides heterocycliques substitues et leurs procedes de preparation. | |
| DE1670200A1 (de) | Neue arylsubstituierte Piperazinylcarbonsaeureanilide und Verfahren zu deren Herstellung | |
| CH437340A (fr) | Procédé de préparation de l'acide N-(2,3-diméthylphényl)-anthranilique | |
| KR100330609B1 (ko) | 3-이속사졸카복실산의 제조방법 | |
| MC1007A1 (fr) | Nouveau procédé de préparation du N-(diéthylaminoéthyl)-2-méthoxy-4-amino-5-chlorobenzamide | |
| CH636350A5 (fr) | Derives de l'acide 2-/(4-quinoleinyl) amino/ 5-fluorobenzoique, leurs procedes de preparation et les compositions pharmaceutiques les renfermant. | |
| KR800001699B1 (ko) | 아미노-페닐-에탄올 아민의 제조방법 | |
| FR2528840A1 (fr) | N-(3-(4-(3-fluorobenzyloxy) phenoxy)propyl) morpholine, son procede de preparation et son application en therapeutique | |
| CH667873A5 (fr) | Derive de n-imidazolidinylmethyl benzamide. | |
| CH392508A (fr) | Procédé de préparation d'esters de 3-phényl-3-pyrrolidinols | |
| CH414667A (fr) | Procédé de préparation de l'acide N-(2,3-diméthyl-phényl)-anthranilique | |
| BE817776Q (fr) | Nouveaux derives de 5-phenyl-tetrazoles | |
| JPS60204772A (ja) | イソオキサゾール誘導体の調製方法 | |
| CH534681A (de) | Verfahren zur Herstellung neuer Phenylpiperidinderivate | |
| CH624094A5 (en) | Process for the preparation of 5-amino-2-propargyloxy-N-n-butylbenzamide | |
| FR2549828A1 (fr) | Procede de preparation de chlorhydrate de trimethobenzamide | |
| FR2575469A1 (fr) | N-imidazolylmethyl-diphenylazomethines, leur preparation et leur application en therapeutique | |
| FR2636329A2 (fr) | Nouveaux derives de la pyridine, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant | |
| CH455739A (fr) | Procédé de préparation de diphénylacétamides | |
| DE1147212B (de) | Verfahren zur Herstellung von Aldehyden | |
| BE501130A (OSRAM) | ||
| BE684910A (OSRAM) | ||
| BE501303A (OSRAM) | ||
| CH346221A (fr) | Procédé de préparation de dérivés de la pipérazine | |
| BE704368A (fr) | Acides p-alkenyloxy-, p-alkynyloxy- et p-cycloalkenyloxyphenylacetiques substitues et leurs procedes de preparation. |