DE1233401B - Verfahren zur Herstellung von 2-(5'-Nitro-2'-furfurylmercapto)-pyridin-1-oxyd oder 2-(2'-Furfurylmercapto)-pyridin-1-oxyd - Google Patents
Verfahren zur Herstellung von 2-(5'-Nitro-2'-furfurylmercapto)-pyridin-1-oxyd oder 2-(2'-Furfurylmercapto)-pyridin-1-oxydInfo
- Publication number
- DE1233401B DE1233401B DEP27140A DEP0027140A DE1233401B DE 1233401 B DE1233401 B DE 1233401B DE P27140 A DEP27140 A DE P27140A DE P0027140 A DEP0027140 A DE P0027140A DE 1233401 B DE1233401 B DE 1233401B
- Authority
- DE
- Germany
- Prior art keywords
- pyridine
- oxide
- furfurylmercapto
- mixture
- nitro
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 5
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- CPZOCLCUJQJRBN-UHFFFAOYSA-N 2-(bromomethyl)-5-nitrofuran Chemical compound [O-][N+](=O)C1=CC=C(CBr)O1 CPZOCLCUJQJRBN-UHFFFAOYSA-N 0.000 claims description 3
- DSOVMPOIRQWUJM-UHFFFAOYSA-N 2-(chloromethyl)-5-nitrofuran Chemical compound [O-][N+](=O)C1=CC=C(CCl)O1 DSOVMPOIRQWUJM-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- 241000222122 Candida albicans Species 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- 229940095731 candida albicans Drugs 0.000 description 3
- -1 fluoride Chemical class 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000555688 Malassezia furfur Species 0.000 description 2
- 241000186359 Mycobacterium Species 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
- 241000599030 Pythium debaryanum Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000223229 Trichophyton rubrum Species 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WMHFOCBFSAHWIH-UHFFFAOYSA-N 1-oxidopyridin-1-ium;hydrobromide Chemical compound Br.[O-][N+]1=CC=CC=C1 WMHFOCBFSAHWIH-UHFFFAOYSA-N 0.000 description 1
- DZJLJUXZISUCGU-UHFFFAOYSA-N 1-oxidopyridin-1-ium;hydrochloride Chemical compound Cl.[O-][N+]1=CC=CC=C1 DZJLJUXZISUCGU-UHFFFAOYSA-N 0.000 description 1
- GANBJDIOIDQSGI-UHFFFAOYSA-N 2-(chloromethyl)furan Chemical compound ClCC1=CC=CO1 GANBJDIOIDQSGI-UHFFFAOYSA-N 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- 241000351920 Aspergillus nidulans Species 0.000 description 1
- 241001465318 Aspergillus terreus Species 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000121260 Bipolaris victoriae Species 0.000 description 1
- 241000335423 Blastomyces Species 0.000 description 1
- 241000228405 Blastomyces dermatitidis Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000722910 Burkholderia mallei Species 0.000 description 1
- 241000030451 Byssochlamys fulva Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000222290 Cladosporium Species 0.000 description 1
- 241001149956 Cladosporium herbarum Species 0.000 description 1
- 241001133184 Colletotrichum agaves Species 0.000 description 1
- 241001306234 Colletotrichum circinans Species 0.000 description 1
- 241000186227 Corynebacterium diphtheriae Species 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001465310 Eremothecium coryli Species 0.000 description 1
- 241000588694 Erwinia amylovora Species 0.000 description 1
- 241000186810 Erysipelothrix rhusiopathiae Species 0.000 description 1
- 241001423728 Fusarium neocosmosporiellum Species 0.000 description 1
- 241000453701 Galactomyces candidum Species 0.000 description 1
- 235000017388 Geotrichum candidum Nutrition 0.000 description 1
- 241000228404 Histoplasma capsulatum Species 0.000 description 1
- 241000441510 Hormodendrum Species 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
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000588915 Klebsiella aerogenes Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- 241000582733 Mycogone perniciosa Species 0.000 description 1
- 241001443590 Naganishia albida Species 0.000 description 1
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000221871 Ophiostoma Species 0.000 description 1
- 241000221671 Ophiostoma ulmi Species 0.000 description 1
- 241001236817 Paecilomyces <Clavicipitaceae> Species 0.000 description 1
- 241000606856 Pasteurella multocida Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000228153 Penicillium citrinum Species 0.000 description 1
- 241000985530 Penicillium glabrum Species 0.000 description 1
- 241000985513 Penicillium oxalicum Species 0.000 description 1
- 241000228168 Penicillium sp. Species 0.000 description 1
- 241000906118 Penicillium steckii Species 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 241001531356 Phialophora verrucosa Species 0.000 description 1
- 241000975369 Phoma betae Species 0.000 description 1
- 241001115351 Physalospora Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 241000235546 Rhizopus stolonifer Species 0.000 description 1
- 241000235004 Saccharomycopsis fibuligera Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000607132 Salmonella enterica subsp. enterica serovar Gallinarum Species 0.000 description 1
- 241000607683 Salmonella enterica subsp. enterica serovar Pullorum Species 0.000 description 1
- 241001149963 Sporothrix schenckii Species 0.000 description 1
- 241000692746 Stenocarpella maydis Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 241001136494 Talaromyces funiculosus Species 0.000 description 1
- 241001480050 Trichophyton violaceum Species 0.000 description 1
- 241001123669 Verticillium albo-atrum Species 0.000 description 1
- 241000607626 Vibrio cholerae Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 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
- 150000001649 bromium compounds Chemical group 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29564A US3027379A (en) | 1960-05-17 | 1960-05-17 | Anti-pathogenic compounds |
| US92174A US3056798A (en) | 1960-05-17 | 1961-02-28 | Process for the preparation of 2-(2'-furfurylmercapto)pyridine-1-oxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1233401B true DE1233401B (de) | 1967-02-02 |
Family
ID=26705084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP27140A Pending DE1233401B (de) | 1960-05-17 | 1961-05-13 | Verfahren zur Herstellung von 2-(5'-Nitro-2'-furfurylmercapto)-pyridin-1-oxyd oder 2-(2'-Furfurylmercapto)-pyridin-1-oxyd |
Country Status (9)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3240791A (en) * | 1963-01-16 | 1966-03-15 | Olin Mathieson | Preparation of 2, 3-dihydropyran from tetrahydrofurfuryl alcohol |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2742476A (en) * | 1953-10-26 | 1956-04-17 | Olin Mathieson | Derivatives of 2-mercaptopyridine 1-oxide |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2686786A (en) * | 1953-01-09 | 1954-08-17 | Olin Mathieson | Nu-hydroxy-2-pyridinethiones and method of preparing same |
| US2742393A (en) * | 1953-05-19 | 1956-04-17 | Olin Mathieson | Derivatives of 2-mercaptopyridine-1-oxide |
| US2922792A (en) * | 1958-01-06 | 1960-01-26 | Olin Mathieson | Certain ester derivatives of 2-mercaptopyridine, n-oxide |
| US2922793A (en) * | 1958-01-06 | 1960-01-26 | Olin Mathieson | 2-allylic thio pyridine n-oxides |
-
0
- NL NL264841D patent/NL264841A/xx unknown
-
1960
- 1960-05-17 US US29564A patent/US3027379A/en not_active Expired - Lifetime
-
1961
- 1961-02-28 US US92174A patent/US3056798A/en not_active Expired - Lifetime
- 1961-03-01 GB GB7444/61A patent/GB903355A/en not_active Expired
- 1961-05-13 DE DEP27140A patent/DE1233401B/de active Pending
- 1961-05-13 ES ES0267391A patent/ES267391A1/es not_active Expired
- 1961-05-16 BR BR129203/61A patent/BR6129203D0/pt unknown
- 1961-05-16 BE BE603875A patent/BE603875A/fr unknown
- 1961-05-17 FR FR862150A patent/FR1142M/fr active Active
- 1961-05-17 CH CH578561A patent/CH410948A/de unknown
- 1961-05-17 CH CH1651565A patent/CH414635A/de unknown
- 1961-05-24 GB GB18704/61A patent/GB920139A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2742476A (en) * | 1953-10-26 | 1956-04-17 | Olin Mathieson | Derivatives of 2-mercaptopyridine 1-oxide |
Also Published As
| Publication number | Publication date |
|---|---|
| US3027379A (en) | 1962-03-27 |
| CH410948A (de) | 1966-04-15 |
| BR6129203D0 (pt) | 1973-06-07 |
| CH414635A (de) | 1966-06-15 |
| ES267391A1 (es) | 1961-11-16 |
| NL264841A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| GB920139A (en) | 1963-03-06 |
| BE603875A (fr) | 1961-11-16 |
| US3056798A (en) | 1962-10-02 |
| FR1142M (fr) | 1962-02-26 |
| GB903355A (en) | 1962-08-15 |
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