DE2447053A1 - Verfahren zur herstellung eines schwefelhaltigen pyridinderivats - Google Patents
Verfahren zur herstellung eines schwefelhaltigen pyridinderivatsInfo
- Publication number
- DE2447053A1 DE2447053A1 DE19742447053 DE2447053A DE2447053A1 DE 2447053 A1 DE2447053 A1 DE 2447053A1 DE 19742447053 DE19742447053 DE 19742447053 DE 2447053 A DE2447053 A DE 2447053A DE 2447053 A1 DE2447053 A1 DE 2447053A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- hydroxy
- pyridine
- methyl
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 6
- 239000002253 acid Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 3
- VGWRNXUFWFDSCH-UHFFFAOYSA-N 4-(ethylaminomethyl)-2-methyl-5-(methylsulfanylmethyl)pyridin-3-ol Chemical compound CCNCC1=C(CSC)C=NC(C)=C1O VGWRNXUFWFDSCH-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- -1 methanol or ethanol Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RADLENWZROEWLP-UHFFFAOYSA-N 3-hydroxy-2-methyl-5-(methylsulfanylmethyl)pyridine-4-carbaldehyde Chemical compound CC1=NC=C(C(=C1O)C=O)CSC RADLENWZROEWLP-UHFFFAOYSA-N 0.000 description 2
- HVEICIWLYSSSDN-UHFFFAOYSA-N 4-(aminomethyl)-2-methyl-5-(methylsulfanylmethyl)pyridin-3-ol Chemical compound CC1=NC=C(C(=C1O)CN)CSC HVEICIWLYSSSDN-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-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
- TYNOKGPWHONZDV-UHFFFAOYSA-N 4-(ethylaminomethyl)-2-methyl-5-(methylsulfanylmethyl)pyridin-3-ol;dihydrochloride Chemical compound Cl.Cl.CCNCC1=C(CSC)C=NC(C)=C1O TYNOKGPWHONZDV-UHFFFAOYSA-N 0.000 description 1
- ABHXVRQHPLALCY-UHFFFAOYSA-N 4-(ethyliminomethyl)-2-methyl-5-(methylsulfanylmethyl)pyridin-3-ol Chemical compound CC1=NC=C(C(=C1O)C=NCC)CSC ABHXVRQHPLALCY-UHFFFAOYSA-N 0.000 description 1
- SWQYYNSMCASIOA-UHFFFAOYSA-N 6-(aminomethyl)-4-ethylidene-2-methyl-5-(methylsulfanylmethyl)-3H-pyridin-3-ol Chemical compound CC1=NC(=C(C(C1O)=CC)CSC)CN SWQYYNSMCASIOA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004870 electrical engineering Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D213/60—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 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
- C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (16)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19742447053 DE2447053A1 (de) | 1974-10-02 | 1974-10-02 | Verfahren zur herstellung eines schwefelhaltigen pyridinderivats |
JP49132109A JPS5141364A (enrdf_load_stackoverflow) | 1974-10-02 | 1974-11-18 | |
NL7511253A NL7511253A (nl) | 1974-10-02 | 1975-09-24 | Werkwijze voor het bereiden van een zwavelbe- vattend pyridinederivaat. |
BE7000717A BE833984A (nl) | 1974-10-02 | 1975-09-29 | Werkwijze voor het beriden van een zwavelbevattend pyridinederivaat |
GB3973975A GB1461068A (en) | 1974-10-02 | 1975-09-29 | Preparation of a sulphur-containing pyridine derivative |
AT746775A AT350568B (de) | 1974-10-02 | 1975-09-30 | Verfahren zur herstellung von 2-methyl-3- hydroxy-4-aethylaminomethyl-5-methyl- mercaptomethyl-pyridin und dessen saeure- additionssalzen |
FR7529902A FR2286818A1 (fr) | 1974-10-02 | 1975-09-30 | Procede de preparation d'un derive soufre de pyridine |
CA236,795A CA1068710A (en) | 1974-10-02 | 1975-10-01 | Preparation of 2-methyl-3-hydroxy-4-ethylaminomethyl-5-methylmercaptomethyl-pyridine and its acid addition salts |
CH1274375A CH602650A5 (enrdf_load_stackoverflow) | 1974-10-02 | 1975-10-01 | |
YU02470/75A YU247075A (en) | 1974-10-02 | 1975-10-01 | Process for obtaining 2-methyl-3-hydroxy-4-ethylaminomethyl-5-methylmercapto-methyl-pyridine |
LU73493A LU73493A1 (enrdf_load_stackoverflow) | 1974-10-02 | 1975-10-01 | |
CS756634A CS188253B2 (en) | 1974-10-02 | 1975-10-01 | Process for preparing 2-methyl-3-hydroxy-4-ethylaminomethyl-5-methylmercaptomethyl-pyridine |
DK442975A DK442975A (da) | 1974-10-02 | 1975-10-01 | Fremgangsmade til fremstilling af et svovlholdigt pyridinderivat |
IE2148/75A IE41740B1 (en) | 1974-10-02 | 1975-10-01 | Preperation of a sulphur-containing pyridine derivative |
SE7511011A SE7511011L (sv) | 1974-10-02 | 1975-10-01 | Forfarande for framstellning av ett svavelhaltigt pyridinderivat |
ES441425A ES441425A1 (es) | 1974-10-02 | 1975-10-02 | Procedimiento para la obtencion de 2-metil-3-hidroxi-4-eti- laminometil-5 - metilmercaptometil-piridina. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19742447053 DE2447053A1 (de) | 1974-10-02 | 1974-10-02 | Verfahren zur herstellung eines schwefelhaltigen pyridinderivats |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2447053A1 true DE2447053A1 (de) | 1976-04-08 |
Family
ID=5927359
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19742447053 Ceased DE2447053A1 (de) | 1974-10-02 | 1974-10-02 | Verfahren zur herstellung eines schwefelhaltigen pyridinderivats |
Country Status (16)
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5843271B2 (ja) * | 1977-05-02 | 1983-09-26 | 凸版印刷株式会社 | 化粧材の製造方法 |
JPS56127484A (en) * | 1980-03-12 | 1981-10-06 | Toppan Printing Co Ltd | Manufacture of facing material having remarkable cubic effect |
JP2668591B2 (ja) * | 1990-03-30 | 1997-10-27 | 日本デコール株式会社 | 化粧シートの製造方法 |
JP4046253B2 (ja) | 1998-05-20 | 2008-02-13 | 大日本印刷株式会社 | 同調エンボス化粧シート及びその製造方法 |
JP4268261B2 (ja) | 1999-05-12 | 2009-05-27 | 大日本印刷株式会社 | 化粧材およびその製造方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH61A (de) * | 1889-01-08 | Grusonwerk Ag | Spann-Vorrichtung für Kanonen | |
US2540946A (en) * | 1947-12-18 | 1951-02-06 | Merck & Co Inc | Pyridoxal-histamine and processes for preparing the same |
-
1974
- 1974-10-02 DE DE19742447053 patent/DE2447053A1/de not_active Ceased
- 1974-11-18 JP JP49132109A patent/JPS5141364A/ja active Pending
-
1975
- 1975-09-24 NL NL7511253A patent/NL7511253A/xx not_active Application Discontinuation
- 1975-09-29 BE BE7000717A patent/BE833984A/xx not_active IP Right Cessation
- 1975-09-29 GB GB3973975A patent/GB1461068A/en not_active Expired
- 1975-09-30 FR FR7529902A patent/FR2286818A1/fr active Granted
- 1975-09-30 AT AT746775A patent/AT350568B/de not_active IP Right Cessation
- 1975-10-01 YU YU02470/75A patent/YU247075A/xx unknown
- 1975-10-01 CA CA236,795A patent/CA1068710A/en not_active Expired
- 1975-10-01 CS CS756634A patent/CS188253B2/cs unknown
- 1975-10-01 IE IE2148/75A patent/IE41740B1/en unknown
- 1975-10-01 DK DK442975A patent/DK442975A/da unknown
- 1975-10-01 LU LU73493A patent/LU73493A1/xx unknown
- 1975-10-01 SE SE7511011A patent/SE7511011L/xx unknown
- 1975-10-01 CH CH1274375A patent/CH602650A5/xx not_active IP Right Cessation
- 1975-10-02 ES ES441425A patent/ES441425A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DK442975A (da) | 1976-04-03 |
IE41740B1 (en) | 1980-03-12 |
AT350568B (de) | 1979-06-11 |
ES441425A1 (es) | 1977-07-01 |
IE41740L (en) | 1976-04-02 |
LU73493A1 (enrdf_load_stackoverflow) | 1977-05-24 |
JPS5141364A (enrdf_load_stackoverflow) | 1976-04-07 |
CA1068710A (en) | 1979-12-25 |
CH602650A5 (enrdf_load_stackoverflow) | 1978-07-31 |
SE7511011L (sv) | 1976-04-05 |
GB1461068A (en) | 1977-01-13 |
YU247075A (en) | 1982-05-31 |
BE833984A (nl) | 1976-03-29 |
NL7511253A (nl) | 1976-04-06 |
FR2286818A1 (fr) | 1976-04-30 |
ATA746775A (de) | 1978-11-15 |
FR2286818B1 (enrdf_load_stackoverflow) | 1979-01-05 |
CS188253B2 (en) | 1979-02-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE2030402C3 (enrdf_load_stackoverflow) | ||
DE2629228C2 (de) | Jodierte Isophthalamsäure-Derivate Verfahren zu deren Herstellung sowie deren Verwendung | |
DE3103372A1 (de) | Neue indanyl-derivate, ihre herstellung und verwendung | |
DE946801C (de) | Verfahren zur Herstellung von Pregnan-11 ª -ol-3, 20-dion und Allopregnan-11 ª-ol-3, 20-dion | |
DE2447053A1 (de) | Verfahren zur herstellung eines schwefelhaltigen pyridinderivats | |
CH615431A5 (enrdf_load_stackoverflow) | ||
DE3020695A1 (de) | Neue hydroxyamino-eburnan-derivate und ein verfahren zu ihrer herstellung | |
DE2539867C2 (de) | 14,15-Dihydro-3β ,16α -eburnameninderivate | |
DD202575A5 (de) | Verfahren zur herstellung neuer bicyclischer verbindungen | |
DE2404946C3 (de) | Verfahren zur Herstellung von 7alpha-Acylthio-Steroidspirolactonen | |
CH619952A5 (enrdf_load_stackoverflow) | ||
CH635342A5 (de) | Verfahren zur herstellung von neuen octahydro-indolo(2,3-a)-chinolizinen. | |
DE69020240T2 (de) | Verfahren zur Herstellung von Beta-lactamase-Inhibitoren. | |
DE3639583C2 (enrdf_load_stackoverflow) | ||
DE3401913A1 (de) | Verfahren zur herstellung von 8-hydroxyoctansaeure und deren salze sowie deren verwendung | |
DE1695554C3 (de) | Verfahren zur Herstellung kondensierter Piperazinonderivate | |
DE19501377B4 (de) | Verfahren zur Herstellung von trans-1,4,5,8-Tetranitro-1,4,5,8-tetraazadecalin (TNAD) | |
DE2735052A1 (de) | Eckige klammer auf n-(2-diphenylmethoxyaethyl)-n-(1-methyl-2-phenoxyaethyl)- n-methyl eckige klammer zu amin, seine herstellung und verwendung in arzneimitteln | |
EP0074488B1 (de) | 2-Azido-3-benzyloxy-propionsäure-benzylester, Verfahren zu dessen Herstellung und dessen Verwendung | |
DE60004054T2 (de) | Neue verfahren zur herstellung von 17beta-hydroxy-17alpha-methyl-2-oxa-5alpha-androstane-3-on | |
DE2824291A1 (de) | Neue benzylalkoholderivate und verfahren zu ihrer herstellung | |
DE1249851B (de) | Morel Ariesheim (Schweiz) j Verfahren zur Herstellung neuer Phenoxyessigsäure amide | |
DE928286C (de) | Verfahren zur Herstellung eines neuen, analgetisch wirksamen 1-Phenyl-pyrazolderivates | |
DE1543602C3 (de) | Substituierte Disulfonamide sowie deren Salze mit nichttoxischen Basen und Verfahren zu ihrer Herstellung | |
DE2341062A1 (de) | Neues cyclohexanpentol-derivat und verfahren zu dessen herstellung |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
8110 | Request for examination paragraph 44 | ||
8131 | Rejection |