NO126177B - - Google Patents
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- Publication number
- NO126177B NO126177B NO03695/71*[A NO369571A NO126177B NO 126177 B NO126177 B NO 126177B NO 369571 A NO369571 A NO 369571A NO 126177 B NO126177 B NO 126177B
- Authority
- NO
- Norway
- Prior art keywords
- chloro
- nitropyridine
- amino
- aminophenylthio
- lower alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 20
- -1 N-acylated 2-amino-(2'-aminophenylthio)-3-nitro-pyridine Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- KWHAFGBGJHCFIH-UHFFFAOYSA-N 2-(3-nitropyridin-2-yl)sulfanylaniline Chemical compound NC1=CC=CC=C1SC1=NC=CC=C1[N+]([O-])=O KWHAFGBGJHCFIH-UHFFFAOYSA-N 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 11
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- SHCWQWRTKPNTEM-UHFFFAOYSA-N 2,6-dichloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1Cl SHCWQWRTKPNTEM-UHFFFAOYSA-N 0.000 description 6
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical class [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OXUOGFGPGGANJG-UHFFFAOYSA-N n-[2-(3-nitropyridin-2-yl)sulfanylphenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1SC1=NC=CC=C1[N+]([O-])=O OXUOGFGPGGANJG-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NGIRMPARLVGMPX-UHFFFAOYSA-N 2-amino-4-chlorobenzenethiol Chemical compound NC1=CC(Cl)=CC=C1S NGIRMPARLVGMPX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PLRYNFGZODCZEI-UHFFFAOYSA-N ClC1=CC=C(C(=N1)SC1=C(NC(C)=O)C=CC=C1)[N+](=O)[O-] Chemical compound ClC1=CC=C(C(=N1)SC1=C(NC(C)=O)C=CC=C1)[N+](=O)[O-] PLRYNFGZODCZEI-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- MJVZSRZTBDMYLX-UHFFFAOYSA-N 2,6-dichloropyridin-3-amine Chemical compound NC1=CC=C(Cl)N=C1Cl MJVZSRZTBDMYLX-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- RYHXWGNHKDQIHJ-UHFFFAOYSA-N n-[4-chloro-2-(3-nitropyridin-2-yl)sulfanylphenyl]acetamide Chemical compound CC(=O)NC1=CC=C(Cl)C=C1SC1=NC=CC=C1[N+]([O-])=O RYHXWGNHKDQIHJ-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- UKDZROJJLPDLDO-UHFFFAOYSA-N 10h-pyrido[3,2-b][1,4]benzothiazine Chemical compound C1=CN=C2NC3=CC=CC=C3SC2=C1 UKDZROJJLPDLDO-UHFFFAOYSA-N 0.000 description 1
- OBUGJYJQJWMOQO-UHFFFAOYSA-N 2,5-dichloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC(Cl)=CN=C1Cl OBUGJYJQJWMOQO-UHFFFAOYSA-N 0.000 description 1
- XERMPLQXCQQVGU-UHFFFAOYSA-N 2-amino-3-chlorobenzenethiol Chemical compound NC1=C(S)C=CC=C1Cl XERMPLQXCQQVGU-UHFFFAOYSA-N 0.000 description 1
- WKEYPPZTEITNHZ-UHFFFAOYSA-N 2-amino-4-bromobenzenethiol Chemical compound NC1=CC(Br)=CC=C1S WKEYPPZTEITNHZ-UHFFFAOYSA-N 0.000 description 1
- BQIJTPFBSNITMH-UHFFFAOYSA-N 2-amino-4-ethylbenzenethiol Chemical compound CCC1=CC=C(S)C(N)=C1 BQIJTPFBSNITMH-UHFFFAOYSA-N 0.000 description 1
- QCLMTLDABHUUBC-UHFFFAOYSA-N 2-amino-4-methylbenzenethiol Chemical compound CC1=CC=C(S)C(N)=C1 QCLMTLDABHUUBC-UHFFFAOYSA-N 0.000 description 1
- TYRZAGMAVZESQX-UHFFFAOYSA-N 2-amino-5-chlorobenzenethiol Chemical compound NC1=CC=C(Cl)C=C1S TYRZAGMAVZESQX-UHFFFAOYSA-N 0.000 description 1
- VUMZNLOQJGKGNE-UHFFFAOYSA-N 2-amino-5-methylbenzenethiol Chemical compound CC1=CC=C(N)C(S)=C1 VUMZNLOQJGKGNE-UHFFFAOYSA-N 0.000 description 1
- CUSZLHZMWOEZBU-UHFFFAOYSA-N 2-amino-6-chlorobenzenethiol Chemical compound NC1=CC=CC(Cl)=C1S CUSZLHZMWOEZBU-UHFFFAOYSA-N 0.000 description 1
- DJXMZLKYKIVBRU-UHFFFAOYSA-N 2-amino-6-methylbenzenethiol Chemical compound CC1=CC=CC(N)=C1S DJXMZLKYKIVBRU-UHFFFAOYSA-N 0.000 description 1
- 150000003930 2-aminopyridines Chemical class 0.000 description 1
- NZEYMNVLIWPZDW-UHFFFAOYSA-N 2-chloro-4,6-dimethyl-3-nitropyridine Chemical compound CC1=CC(C)=C([N+]([O-])=O)C(Cl)=N1 NZEYMNVLIWPZDW-UHFFFAOYSA-N 0.000 description 1
- WFPKNWVTBHSLPX-UHFFFAOYSA-N 2-chloro-4-ethyl-3-nitropyridine Chemical compound CCC1=CC=NC(Cl)=C1[N+]([O-])=O WFPKNWVTBHSLPX-UHFFFAOYSA-N 0.000 description 1
- JHARVUVBTAAPLA-UHFFFAOYSA-N 2-chloro-4-methyl-3-nitropyridine Chemical compound CC1=CC=NC(Cl)=C1[N+]([O-])=O JHARVUVBTAAPLA-UHFFFAOYSA-N 0.000 description 1
- MXZJAIFPQQEWDB-UHFFFAOYSA-N 2-chloro-5-ethyl-3-nitropyridine Chemical compound ClC1=NC=C(C=C1[N+](=O)[O-])CC MXZJAIFPQQEWDB-UHFFFAOYSA-N 0.000 description 1
- LUAJUWOJEFFNFE-UHFFFAOYSA-N 2-chloro-5-methyl-3-nitropyridine Chemical compound CC1=CN=C(Cl)C([N+]([O-])=O)=C1 LUAJUWOJEFFNFE-UHFFFAOYSA-N 0.000 description 1
- SWRNZSYPKYMFFB-UHFFFAOYSA-N 2-chloro-6-ethyl-3-nitropyridine Chemical compound CCC1=CC=C([N+]([O-])=O)C(Cl)=N1 SWRNZSYPKYMFFB-UHFFFAOYSA-N 0.000 description 1
- UIEVSGOVFXWCIK-UHFFFAOYSA-N 2-chloro-6-methyl-3-nitropyridine Chemical compound CC1=CC=C([N+]([O-])=O)C(Cl)=N1 UIEVSGOVFXWCIK-UHFFFAOYSA-N 0.000 description 1
- GWYXGAVKUBLXOG-UHFFFAOYSA-N 3-amino-4-chlorobenzenethiol Chemical compound NC1=CC(S)=CC=C1Cl GWYXGAVKUBLXOG-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NDTRUILHKVKGFL-UHFFFAOYSA-N 5-amino-6-hydroxy-1h-pyridin-2-one Chemical compound NC=1C=CC(=O)NC=1O NDTRUILHKVKGFL-UHFFFAOYSA-N 0.000 description 1
- QRBABRPBSDWTTE-UHFFFAOYSA-N 5-bromo-6-hydroxy-1h-pyridin-2-one Chemical compound OC=1NC(=O)C=CC=1Br QRBABRPBSDWTTE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 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 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR92828A FR1546478A (fr) | 1967-01-27 | 1967-01-27 | Nouveaux dérivés de l'acide benzoyl-3 phénylacétique et leur préparation |
| FR132526A FR94930E (fr) | 1967-01-27 | 1967-12-15 | Nouveaux dérivés de l'acide benzoyl-3 phénylacétique et leur préparation. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126177B true NO126177B (da) | 1973-01-02 |
Family
ID=26174596
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO0304/68A NO125672B (da) | 1967-01-27 | 1968-01-24 | |
| NO03695/71*[A NO126177B (da) | 1967-01-27 | 1971-10-07 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO0304/68A NO125672B (da) | 1967-01-27 | 1968-01-24 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3641127A (da) |
| AT (3) | AT281798B (da) |
| BE (1) | BE709964A (da) |
| CH (1) | CH484863A (da) |
| CY (1) | CY668A (da) |
| DE (1) | DE1668648C3 (da) |
| DK (2) | DK119153B (da) |
| ES (3) | ES349842A1 (da) |
| FI (1) | FI45953C (da) |
| FR (2) | FR1546478A (da) |
| GB (1) | GB1164585A (da) |
| IE (1) | IE31886B1 (da) |
| IL (1) | IL29377A (da) |
| LU (1) | LU55356A1 (da) |
| MY (1) | MY7300143A (da) |
| NL (1) | NL146485B (da) |
| NO (2) | NO125672B (da) |
| OA (1) | OA03403A (da) |
| SE (1) | SE346989B (da) |
| SU (1) | SU544364A3 (da) |
| YU (3) | YU32373B (da) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2460984A (en) * | 1944-06-06 | 1949-02-08 | Wright Aeronautical Corp | Pipe connection |
| FR2043472A1 (da) * | 1969-05-19 | 1971-02-19 | Rhone Poulenc Sa | |
| FR2202873A2 (en) * | 1972-10-16 | 1974-05-10 | Rhone Poulenc Sa | 3-benzoylphenyl acetic and 2-(3-benzoyl phenyl) - propionic acids prepn - for use as anti-inflammatories |
| OA04219A (fr) * | 1971-12-03 | 1979-12-31 | Rhone Poulenc Sa | Nouveau procédé de préparation de l'acide (benzol-3-phényl)-2 propionique et analogues. |
| FR2163875A5 (en) * | 1971-12-03 | 1973-07-27 | Rhone Poulenc Sa | 3-benzoylphenyl acetic and 2-(3-benzoyl phenyl) - propionic acids prepn - for use as anti-inflammatories |
| US3928415A (en) * | 1973-05-08 | 1975-12-23 | Cassella Farbwerke Mainkur Ag | Benzophenone derivatives and process for their production II |
| FR2278331A1 (fr) * | 1974-01-24 | 1976-02-13 | Roussel Uclaf | Nouveaux acides carboxyliques et leurs derives, leur application comme medicaments et leur procede de preparation |
| US4216326A (en) | 1975-01-20 | 1980-08-05 | Sterling Drug Inc. | Intermediates for preparing anti-inflammatory phenyl-lower-alkylamines |
| DE2646792C2 (de) * | 1975-10-23 | 1985-05-09 | Mitsubishi Petrochemical Co., Ltd., Tokio/Tokyo | Verfahren zur Herstellung einer α-(arylsubstituierten)-Propionsäure und/oder eines Esters derselben |
| YU39415B (en) * | 1978-04-10 | 1984-12-31 | Lek Tovarna Farmacevtskih | Process for preparing 2-(3-benzoyl-phenyl)-propionic acid |
| US4417052A (en) | 1980-02-15 | 1983-11-22 | Sterling Drug Inc. | Phenyl-lower-alkyl piperidines and pyrrolidines |
| DE3026402A1 (de) * | 1980-07-11 | 1982-02-04 | Syntex Corp., Palo Alto, Calif. | Die verwendung analgetischer und nicht-hormonaler, entzuendungshemmender mittel bei der behandlung von mikrovaskulaeren erkrankungen |
| AT370721B (de) * | 1981-02-24 | 1983-04-25 | Ciba Geigy Ag | Verfahren zur herstellung von neuen salzen der 2- (2,6-dichloranilino)-phenylessigsaeure, der |
| US5166141A (en) * | 1983-11-01 | 1992-11-24 | Scripps Clinic And Research Foundation | Immunostimulating 7-deaza-7-oxa- and 7-deaza-7-oxo-analogs of 8-substituted-guanine-9-(1'-beta-D-aldoglycosidyl) derivatives and methods of treating test animals |
| KR960002598B1 (ko) * | 1987-03-20 | 1996-02-23 | 니혼 세끼유 가가꾸 가부시끼가이샤 | α-(3-벤질페닐)프로피온산 유도체의 제조방법 |
| US4868214A (en) * | 1987-11-17 | 1989-09-19 | Analgesic Associates | Onset-hastened/enhanced analgesia |
| JP2518014B2 (ja) * | 1988-05-31 | 1996-07-24 | 日産化学工業株式会社 | α−置換酢酸の精製方法 |
| CA2023954C (en) * | 1989-10-17 | 1999-05-04 | Hiroyuki Nohira | Process for the optical resolution of 2-(3-benzoyl) phenylpropionic acid |
| US5071988A (en) * | 1989-10-27 | 1991-12-10 | American Home Products Corporation | Substituted benzoylbenzene-, biphenyl- and 2-oxazole-alkanoic acid derivatives |
| US5218124A (en) * | 1989-10-27 | 1993-06-08 | American Home Products Corporation | Substituted benzoylbenzene-, biphenyl- and 2-oxazole-alkanoic acid derivatives as inhibitors of pla2 and lipoxygenase |
| DE69210323T3 (de) * | 1991-07-31 | 1999-06-02 | Tessenderlo Chem Nv | Verfahren zur Alpha-Monoalkierung von Arylacetonitrilen, Arylacetoestern und Arylessigsäuren |
| DE4128787A1 (de) * | 1991-08-30 | 1993-03-04 | Bayer Ag | Neue zwischenprodukte und ihre verwendung bei der herstellung von s-ketoprofen |
| FR2687915B1 (fr) * | 1992-02-28 | 1995-05-05 | Rhone Poulenc Rorer Sa | Composition pharmaceutique utilisable comme analgesique contenant l'acide (benzoyl-3 phenyl)-2 propionique-(r). |
| US5331000A (en) * | 1992-03-09 | 1994-07-19 | Sepracor Inc. | Antipyretic and analgesic methods and compositions containing optically pure R(-) ketoprofen |
| ES2049647B1 (es) * | 1992-07-28 | 1994-12-16 | Menarini Lab | "procedimiento para la preparacion de nuevos derivados del acido 2-(3-benzoilfenil) propionico" |
| ES2058024B1 (es) * | 1992-11-10 | 1995-05-01 | Menarini Lab | Nuevo derivado arilpropionico, procedimiento de fabricacion del mismo y su utilizacion como analgesico. |
| DE4319438C1 (de) * | 1993-06-11 | 1994-06-01 | Gerd Dr Dr Geislinger | Arzneimittel auf der Grundlage von Ketoprofen zur Bekämpfung von Schmerzen und/oder Entzündungen und/oder Fieber an Menschen und Tieren |
| WO1995025511A1 (en) * | 1994-03-18 | 1995-09-28 | Bayer Corporation | Low dosage ketoprofen |
| JPH08151344A (ja) * | 1994-09-26 | 1996-06-11 | Nagase & Co Ltd | ２−（３−ベンゾイルフェニル）プロピオン酸の光学分割方法 |
| ES2109859B1 (es) * | 1994-11-23 | 1998-08-16 | Menarini Lab | Nuevos derivados arilpropionicos con accion analgesica y procedimiento para su obtencion. |
| US5792886A (en) * | 1997-01-08 | 1998-08-11 | Albemarle Corporation | Production of racemic 2-(6-methoxy-2-naphthyl) propionic acid of precursors thereof |
| US6080888A (en) * | 1997-01-08 | 2000-06-27 | Albemarle Corporation | Preparation of olefinic compounds and carboxylic derivatives thereof |
| US6096920A (en) * | 1997-01-08 | 2000-08-01 | Albemarle Corporation | Preparation of carboxylic compounds and their derivatives |
| US6268526B1 (en) | 1998-12-16 | 2001-07-31 | Albemarle Corporation | Palladium catalyzed carbonylation process utilizing aromatic substituted alcohols and/or aromatic substituted alkyl halides |
| IT1308633B1 (it) | 1999-03-02 | 2002-01-09 | Nicox Sa | Nitrossiderivati. |
| US20080021085A1 (en) * | 2000-04-13 | 2008-01-24 | Mayo Foundation For Medical Education And Research | Method of reducing abeta42 and treating diseases |
| CA2406383A1 (en) * | 2000-04-13 | 2001-10-25 | Mayo Foundation For Medical Education And Research | A.beta.42 lowering agents |
| IT1318673B1 (it) * | 2000-08-08 | 2003-08-27 | Nicox Sa | Farmaci per le disfunzioni sessuali. |
| IT1318674B1 (it) * | 2000-08-08 | 2003-08-27 | Nicox Sa | Faramaci per l'incontinenza. |
| US20030027867A1 (en) * | 2001-06-29 | 2003-02-06 | Myriad Genetics, Incorporated | Use of R-NSAID compounds for anti-HIV treatment |
| MXPA05003050A (es) * | 2002-09-20 | 2005-05-27 | Nicox Sa | Procedimiento de fabricacion para compuestos donadores de oxido de nitrogeno tales como diclofenaco donador de oxido de nitrogeno. |
| US7090859B2 (en) * | 2002-12-13 | 2006-08-15 | Ronald Thomas Haas | Ketoprofen compositions and methods of making them |
| EP1603548A4 (en) * | 2003-02-05 | 2007-10-10 | Myriad Genetics Inc | COMPOSITION AND METHOD FOR TREATING NEURODEGENERATIVE DISORDERS |
| US20050042284A1 (en) * | 2003-07-11 | 2005-02-24 | Myriad Genetics, Incorporated | Pharmaceutical methods, dosing regimes and dosage forms for the treatment of Alzheimer's disease |
| US20050171207A1 (en) * | 2003-09-26 | 2005-08-04 | Myriad Genetics, Incorporated | Method and composition for combination treatment of neurodegenerative disorders |
| US20060047171A1 (en) * | 2003-12-22 | 2006-03-02 | Harold Meckler | Catalytic hydrogenation of nitriles to produce capsaicinoid derivatives and amine compounds, and methods for purifying and obtaining the polymorphs thereof |
| WO2006001877A2 (en) * | 2004-04-13 | 2006-01-05 | Myriad Genetics, Inc. | Combination treatment for neurodegenerative disorders comprising r-flurbiprofen |
| CN1946906A (zh) * | 2004-04-29 | 2007-04-11 | 吉斯通护岸系统股份有限公司 | 用于墙、护墙和类似物的饰面 |
| WO2006020852A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
| CA2618985A1 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
| WO2006020850A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
| US20070015832A1 (en) * | 2005-07-14 | 2007-01-18 | Myriad Genetics, Incorporated | Methods of treating overactive bladder and urinary incontinence |
| CA2615063A1 (en) * | 2005-07-22 | 2007-02-01 | Myriad Genetics, Inc. | High drug load formulations and dosage forms |
| EP2046119A2 (en) * | 2006-07-07 | 2009-04-15 | Myriad Genetics, Inc. | Treatment of psychiatric disorders |
| LT5696B (lt) | 2009-01-22 | 2010-11-25 | Sanofi-Synthelabo (India) Ltd, Gidc | Aktyvių ingredientų, turinčių nesteroidinį priešuždegiminį vaistą ir kolchikozido darinį, naujas derinys |
| ES2432222B1 (es) | 2012-04-30 | 2014-06-10 | Farmalider S.A. | Composición farmacéutica inyectable de dexketoprofeno y tramadol |
| WO2014007780A1 (en) | 2012-07-06 | 2014-01-09 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Orally-disintegrating formulations of dexketoprofen |
| WO2014007779A1 (en) | 2012-07-06 | 2014-01-09 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Orally-disintegrating formulations of dexketoprofen |
| EP2730271B1 (en) | 2012-11-11 | 2018-01-24 | Symrise AG | Aqeuous compositions |
| ES2701758T3 (es) | 2013-02-27 | 2019-02-25 | Symrise Ag | Extracto de jengibre para la protección de citoblastos |
| EP2862852B1 (en) | 2013-10-18 | 2018-07-04 | Symrise AG | Urea derivatives for the protection of stem cells |
| ES2901706T3 (es) | 2013-12-16 | 2022-03-23 | Zoetis Services Llc | Composiciones de ketoprofeno de acción prolongada |
| EP2921157B1 (en) | 2014-03-18 | 2017-08-16 | Symrise AG | Coated titanium dioxide to reduce whitening effect on skin |
| ES2819207T3 (es) | 2014-04-29 | 2021-04-15 | Symrise Ag | Mezclas activas |
| EP3045161A1 (en) | 2015-01-18 | 2016-07-20 | Symrise AG | Active compositions comprising 1,2-hexanediol and 1,2-octanediol |
-
1967
- 1967-01-27 FR FR92828A patent/FR1546478A/fr not_active Expired
- 1967-12-15 FR FR132526A patent/FR94930E/fr not_active Expired
-
1968
- 1968-01-18 OA OA53169A patent/OA03403A/xx unknown
- 1968-01-19 NL NL686800880A patent/NL146485B/xx not_active IP Right Cessation
- 1968-01-24 NO NO0304/68A patent/NO125672B/no unknown
- 1968-01-25 FI FI680194A patent/FI45953C/fi active
- 1968-01-25 US US700375A patent/US3641127A/en not_active Expired - Lifetime
- 1968-01-25 IE IE107/68A patent/IE31886B1/xx unknown
- 1968-01-26 DE DE1668648A patent/DE1668648C3/de not_active Expired
- 1968-01-26 GB GB4326/68A patent/GB1164585A/en not_active Expired
- 1968-01-26 IL IL29377A patent/IL29377A/xx unknown
- 1968-01-26 CH CH121968A patent/CH484863A/fr not_active IP Right Cessation
- 1968-01-26 AT AT432569A patent/AT281798B/de not_active IP Right Cessation
- 1968-01-26 YU YU0188/68A patent/YU32373B/xx unknown
- 1968-01-26 AT AT04324/69A patent/AT280248B/de active
- 1968-01-26 LU LU55356D patent/LU55356A1/xx unknown
- 1968-01-26 AT AT79468A patent/AT280245B/de not_active IP Right Cessation
- 1968-01-26 BE BE709964D patent/BE709964A/xx not_active IP Right Cessation
- 1968-01-26 DK DK31668AA patent/DK119153B/da not_active IP Right Cessation
- 1968-01-26 SE SE01090/68A patent/SE346989B/xx unknown
- 1968-01-27 ES ES349842A patent/ES349842A1/es not_active Expired
- 1968-05-03 ES ES353485A patent/ES353485A1/es not_active Expired
- 1968-05-03 ES ES353484A patent/ES353484A1/es not_active Expired
-
1969
- 1969-01-06 SU SU1295338A patent/SU544364A3/ru active
-
1970
- 1970-03-24 DK DK151970AA patent/DK125550B/da not_active IP Right Cessation
-
1971
- 1971-10-07 NO NO03695/71*[A patent/NO126177B/no unknown
-
1973
- 1973-01-05 CY CY66873A patent/CY668A/xx unknown
- 1973-03-27 YU YU820/73A patent/YU34657B/xx unknown
- 1973-07-27 YU YU819/73A patent/YU34656B/xx unknown
- 1973-12-30 MY MY1343/73A patent/MY7300143A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU55356A1 (da) | 1968-08-30 |
| YU81973A (en) | 1979-07-10 |
| FI45953C (fi) | 1972-11-10 |
| NO125672B (da) | 1972-10-16 |
| FR94930E (fr) | 1970-01-23 |
| FI45953B (da) | 1972-07-31 |
| AT281798B (de) | 1970-06-10 |
| NL6800880A (da) | 1968-07-29 |
| AT280245B (de) | 1970-04-10 |
| NL146485B (nl) | 1975-07-15 |
| YU18868A (en) | 1974-04-30 |
| MY7300143A (en) | 1973-12-31 |
| BE709964A (da) | 1968-07-26 |
| US3641127A (en) | 1972-02-08 |
| YU34657B (en) | 1979-12-31 |
| IE31886L (en) | 1968-07-27 |
| DK119153B (da) | 1970-11-23 |
| ES353484A1 (es) | 1970-01-16 |
| IE31886B1 (en) | 1973-02-07 |
| DE1668648B2 (de) | 1973-07-19 |
| IL29377A (en) | 1971-04-28 |
| ES353485A1 (es) | 1969-10-16 |
| FR1546478A (fr) | 1968-11-22 |
| YU32373B (en) | 1974-10-31 |
| DK125550B (da) | 1973-03-05 |
| CY668A (en) | 1973-01-05 |
| DE1668648A1 (de) | 1971-09-02 |
| ES349842A1 (es) | 1969-04-16 |
| YU34656B (en) | 1979-12-31 |
| CH484863A (fr) | 1970-01-31 |
| GB1164585A (en) | 1969-09-17 |
| SU544364A3 (ru) | 1977-01-25 |
| DE1668648C3 (de) | 1974-02-21 |
| SE346989B (da) | 1972-07-24 |
| AT280248B (de) | 1970-04-10 |
| YU82073A (en) | 1979-07-10 |
| OA03403A (fr) | 1970-12-15 |
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