SK284903B6 - Spôsob výroby 1-(6-metylpyridín-3-yl)-2-[(4- (metylsulfonyl)fenyl]etanónu a medziprodukty - Google Patents
Spôsob výroby 1-(6-metylpyridín-3-yl)-2-[(4- (metylsulfonyl)fenyl]etanónu a medziprodukty Download PDFInfo
- Publication number
- SK284903B6 SK284903B6 SK972-2001A SK9722001A SK284903B6 SK 284903 B6 SK284903 B6 SK 284903B6 SK 9722001 A SK9722001 A SK 9722001A SK 284903 B6 SK284903 B6 SK 284903B6
- Authority
- SK
- Slovakia
- Prior art keywords
- methyl
- methylpyridin
- formula
- carbaldehyde
- acetonitrile
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 title claims abstract description 11
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 23
- 239000000543 intermediate Substances 0.000 title 1
- -1 6-methylpyridin-3-yl Chemical group 0.000 claims description 37
- IMWMEIWYPWVABQ-UHFFFAOYSA-N 6-methylpyridine-3-carbaldehyde Chemical compound CC1=CC=C(C=O)C=N1 IMWMEIWYPWVABQ-UHFFFAOYSA-N 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 claims description 18
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 13
- 150000001340 alkali metals Chemical class 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000005265 dialkylamine group Chemical group 0.000 claims description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 6
- FPYHDPGONAVLDJ-UHFFFAOYSA-N hydroxy-(6-methylpyridin-3-yl)methanesulfonic acid Chemical class CC1=CC=C(C(O)S(O)(=O)=O)C=N1 FPYHDPGONAVLDJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 2
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 claims description 2
- 229910001950 potassium oxide Inorganic materials 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- UKVQBONVSSLJBB-UHFFFAOYSA-N 2-pyridin-2-ylacetonitrile Chemical compound N#CCC1=CC=CC=N1 UKVQBONVSSLJBB-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229940111134 coxibs Drugs 0.000 abstract description 2
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- LXPRVXKHIXWBJZ-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfonylbenzene Chemical group CS(=O)(=O)C1=CC=C(CCl)C=C1 LXPRVXKHIXWBJZ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000008262 pumice Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- MAQAGRJURDEYDQ-UHFFFAOYSA-N 6-methylpyridine Chemical compound CC1=C=CC=C[N]1 MAQAGRJURDEYDQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 238000007059 Strecker synthesis reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 239000004293 potassium hydrogen sulphite Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99100590 | 1999-01-14 | ||
| US14599699P | 1999-07-29 | 1999-07-29 | |
| PCT/EP2000/000240 WO2000042014A2 (de) | 1999-01-14 | 2000-01-13 | 1-(6-methylpyridin-3-yl)-2-((4-(methylsulfonyl)phenyl)ethanon und verfahren zu seiner herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK9722001A3 SK9722001A3 (en) | 2001-12-03 |
| SK284903B6 true SK284903B6 (sk) | 2006-02-02 |
Family
ID=34089809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK972-2001A SK284903B6 (sk) | 1999-01-14 | 2000-01-13 | Spôsob výroby 1-(6-metylpyridín-3-yl)-2-[(4- (metylsulfonyl)fenyl]etanónu a medziprodukty |
Country Status (15)
| Country | Link |
|---|---|
| EP (2) | EP1394149B1 (cs) |
| JP (1) | JP4765167B2 (cs) |
| CN (2) | CN1170820C (cs) |
| AT (2) | ATE287396T1 (cs) |
| AU (1) | AU2290800A (cs) |
| CA (2) | CA2359958C (cs) |
| CZ (1) | CZ302270B6 (cs) |
| DE (2) | DE50009312D1 (cs) |
| DK (2) | DK1394149T3 (cs) |
| ES (2) | ES2235138T3 (cs) |
| HU (1) | HUP0105124A3 (cs) |
| IL (1) | IL143981A0 (cs) |
| PT (2) | PT1159270E (cs) |
| SK (1) | SK284903B6 (cs) |
| WO (1) | WO2000042014A2 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104725300A (zh) * | 2015-02-28 | 2015-06-24 | 宁波九胜创新医药科技有限公司 | 一种1-(6-甲基吡啶-3-基)-2-(4-甲磺酰基苯基)乙酮的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3313683A (en) * | 1963-04-22 | 1967-04-11 | Lilly Co Eli | Nematocidal and fungicidal methods |
| FR2074674A1 (en) * | 1970-01-16 | 1971-10-08 | Simafex | Sulphonamide/aldehyde-bisulphite complexes - antibacterials with very high solubility in water |
| US4155909A (en) * | 1977-06-13 | 1979-05-22 | Philip Morris Incorporated | 2-Alkyl nicotinoids and processes for their production |
| US5596008A (en) * | 1995-02-10 | 1997-01-21 | G. D. Searle & Co. | 3,4-Diaryl substituted pyridines for the treatment of inflammation |
| AU723179B2 (en) * | 1996-07-18 | 2000-08-17 | Merck Canada Inc. | Substituted pyridines as selective cyclooxygenase-2 inhibitors |
| TW492959B (en) * | 1997-04-18 | 2002-07-01 | Merck & Co Inc | Process for making 2-aryl-3-aryl-5-halo pyridines useful as cox-2 inhibitors |
| AR015938A1 (es) * | 1997-09-25 | 2001-05-30 | Merck Sharp & Dohme | Procedimiento para preparar diaril piridinas utiles como inhibidores cox-2 y compuesto intermediario |
| SI1071745T1 (en) * | 1998-04-24 | 2004-10-31 | Merck & Co., Inc. | Process for synthesizing cox-2 inhibitors |
-
2000
- 2000-01-13 DE DE50009312T patent/DE50009312D1/de not_active Expired - Lifetime
- 2000-01-13 SK SK972-2001A patent/SK284903B6/sk not_active IP Right Cessation
- 2000-01-13 WO PCT/EP2000/000240 patent/WO2000042014A2/de active Application Filing
- 2000-01-13 CN CNB008027218A patent/CN1170820C/zh not_active Expired - Fee Related
- 2000-01-13 DK DK03024787T patent/DK1394149T3/da active
- 2000-01-13 AU AU22908/00A patent/AU2290800A/en not_active Abandoned
- 2000-01-13 CZ CZ20012457A patent/CZ302270B6/cs not_active IP Right Cessation
- 2000-01-13 AT AT03024787T patent/ATE287396T1/de active
- 2000-01-13 DE DE50004327T patent/DE50004327D1/de not_active Expired - Lifetime
- 2000-01-13 HU HU0105124A patent/HUP0105124A3/hu unknown
- 2000-01-13 JP JP2000593582A patent/JP4765167B2/ja not_active Expired - Fee Related
- 2000-01-13 ES ES03024787T patent/ES2235138T3/es not_active Expired - Lifetime
- 2000-01-13 EP EP03024787A patent/EP1394149B1/de not_active Expired - Lifetime
- 2000-01-13 PT PT00901555T patent/PT1159270E/pt unknown
- 2000-01-13 CA CA002359958A patent/CA2359958C/en not_active Expired - Fee Related
- 2000-01-13 CN CNB200410069946XA patent/CN1281589C/zh not_active Expired - Fee Related
- 2000-01-13 CA CA002485739A patent/CA2485739C/en not_active Expired - Fee Related
- 2000-01-13 ES ES00901555T patent/ES2209807T3/es not_active Expired - Lifetime
- 2000-01-13 DK DK00901555T patent/DK1159270T3/da active
- 2000-01-13 EP EP00901555A patent/EP1159270B1/de not_active Expired - Lifetime
- 2000-01-13 IL IL14398100A patent/IL143981A0/xx active IP Right Grant
- 2000-01-13 PT PT03024787T patent/PT1394149E/pt unknown
- 2000-01-13 AT AT00901555T patent/ATE253559T1/de active
Also Published As
| Publication number | Publication date |
|---|---|
| CN1583723A (zh) | 2005-02-23 |
| ATE287396T1 (de) | 2005-02-15 |
| JP4765167B2 (ja) | 2011-09-07 |
| CN1170820C (zh) | 2004-10-13 |
| CN1281589C (zh) | 2006-10-25 |
| ATE253559T1 (de) | 2003-11-15 |
| JP2003518002A (ja) | 2003-06-03 |
| CA2359958C (en) | 2006-04-04 |
| HUP0105124A3 (en) | 2002-05-28 |
| EP1159270B1 (de) | 2003-11-05 |
| PT1159270E (pt) | 2004-03-31 |
| DK1159270T3 (da) | 2004-02-23 |
| WO2000042014A2 (de) | 2000-07-20 |
| CA2485739C (en) | 2009-09-22 |
| DE50004327D1 (de) | 2003-12-11 |
| DE50009312D1 (de) | 2005-02-24 |
| EP1159270A2 (de) | 2001-12-05 |
| HUP0105124A2 (hu) | 2002-04-29 |
| CA2485739A1 (en) | 2000-07-20 |
| PT1394149E (pt) | 2005-05-31 |
| CZ20012457A3 (cs) | 2002-01-16 |
| ES2235138T3 (es) | 2005-07-01 |
| DK1394149T3 (da) | 2005-04-04 |
| IL143981A0 (en) | 2002-04-21 |
| WO2000042014A3 (de) | 2000-12-07 |
| SK9722001A3 (en) | 2001-12-03 |
| EP1394149B1 (de) | 2005-01-19 |
| CA2359958A1 (en) | 2000-07-20 |
| EP1394149A1 (de) | 2004-03-03 |
| CN1359374A (zh) | 2002-07-17 |
| AU2290800A (en) | 2000-08-01 |
| CZ302270B6 (cs) | 2011-01-19 |
| ES2209807T3 (es) | 2004-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK284903B6 (sk) | Spôsob výroby 1-(6-metylpyridín-3-yl)-2-[(4- (metylsulfonyl)fenyl]etanónu a medziprodukty | |
| US7141673B1 (en) | 1-(6-methylpyridine-3-yl)-2-[4-(methylsulphonyl) phenyl] ethanone and method for its preparation | |
| CN110903238A (zh) | 一种伐度司他的制备方法 | |
| US12291495B2 (en) | Process for the production of substituted 2-[2-(phenyl)ethylamino] alkaneamide derivatives | |
| Ramana Reddy et al. | Thioglycolates in the synthesis of bis (styryl)-sulfones | |
| EP0279643B1 (en) | Cyanoguanidine derivatives, the preparation thereof and their use for the synthesis of cimetidine | |
| JP3031279B2 (ja) | ２−アルコキシ−６−（トリフルオロメチル）ピリミジン−４−オルの製造方法 | |
| CN112159358A (zh) | 一种噁拉戈利中间体的制备方法 | |
| JPH0680048B2 (ja) | オトロ酸の製法 | |
| JP2003212861A (ja) | ピリミジニルアルコール誘導体の製造方法及びその合成中間体 | |
| TWI282789B (en) | Process for the preparation of 1-(6-methylpyridin-3-yl)-2-[(4-(methylsulphonyl)phenyl]ethanone | |
| HU213533B (en) | Process for producing 3-(hydroxymethyl)-1-propargylimidazolidine-2,4-dione | |
| US4487721A (en) | Process for producing 2-amino-2-arylacetonitriles | |
| JP4018816B2 (ja) | シクロヘプテノン誘導体及びその製造方法並びにそれを利用してシクロヘプトイミダゾール誘導体を製造する方法 | |
| JPH0316339B2 (cs) | ||
| JP4061901B2 (ja) | ３−カルボキシインダゾール誘導体及びその製法 | |
| JP4058960B2 (ja) | インダゾール誘導体及びその製法 | |
| JPH03127780A (ja) | アニリノピリミジン誘導体 | |
| JPH0152384B2 (cs) | ||
| JPS58413B2 (ja) | （ｎ−メチルピリル−２）アセトチオアミド誘導体 | |
| CS273077B1 (en) | Method of 2-phenyl-4-chloro-5-methoxy-3 (2h)-pyridazinone preparation | |
| FR2741068A1 (fr) | Procede de preparation de 7,8-dihydroisoquinolein-5(6h)-one |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20120113 |