HU189674B - Improved process for preparing hydroxyethyl-tetrazole-thiol - Google Patents
Improved process for preparing hydroxyethyl-tetrazole-thiol Download PDFInfo
- Publication number
- HU189674B HU189674B HU83978A HU97883A HU189674B HU 189674 B HU189674 B HU 189674B HU 83978 A HU83978 A HU 83978A HU 97883 A HU97883 A HU 97883A HU 189674 B HU189674 B HU 189674B
- Authority
- HU
- Hungary
- Prior art keywords
- thiol
- alkyl
- hydroxyethyl
- formula
- acid
- Prior art date
Links
- CTHXQMKBVXJFKU-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)ethanol Chemical compound OCCSC1=NN=NN1 CTHXQMKBVXJFKU-UHFFFAOYSA-N 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 N-(2-hydroxyethyl)dithiocarbamate ester Chemical class 0.000 claims abstract description 34
- YKYUEQRWYGVUKB-UHFFFAOYSA-N 1-(2-hydroxyethyl)-2h-tetrazole-5-thione Chemical compound OCCN1N=NN=C1S YKYUEQRWYGVUKB-UHFFFAOYSA-N 0.000 claims abstract description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 229910052783 alkali metal Inorganic materials 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 150000003573 thiols Chemical class 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- MMLBEXXDOLIGCR-UHFFFAOYSA-N 2-hydroxyethylcarbamodithioic acid Chemical compound OCCNC(S)=S MMLBEXXDOLIGCR-UHFFFAOYSA-N 0.000 claims description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 2
- 125000006241 alcohol protecting group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 239000002609 medium Substances 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 150000001540 azides Chemical class 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000010511 deprotection reaction Methods 0.000 description 8
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- GJUIUIJPXQCMFE-UHFFFAOYSA-N methyl n-(2-hydroxyethyl)carbamodithioate Chemical compound CSC(=S)NCCO GJUIUIJPXQCMFE-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 150000003536 tetrazoles Chemical group 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 239000012990 dithiocarbamate Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QXOAYOGFDRZZMC-UHFFFAOYSA-N 2-hydroxyethyl(methyl)carbamodithioic acid Chemical compound SC(=S)N(C)CCO QXOAYOGFDRZZMC-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
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 150000004659 dithiocarbamates Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical group CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- TZQXIGYVNXRGBN-UHFFFAOYSA-N 2-(oxan-2-yl)-1,4-dioxane Chemical compound O1CCCCC1C1OCCOC1 TZQXIGYVNXRGBN-UHFFFAOYSA-N 0.000 description 1
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 1
- POGYLLIVUZKDGJ-UHFFFAOYSA-N CCOC(C)OCCN(C)C(=S)S Chemical compound CCOC(C)OCCN(C)C(=S)S POGYLLIVUZKDGJ-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical group CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MWAJVXKKZYGMAW-UHFFFAOYSA-N methyl N-[2-[1-(2-methylpropoxy)ethoxy]ethyl]carbamodithioate Chemical compound CSC(NCCOC(C)OCC(C)C)=S MWAJVXKKZYGMAW-UHFFFAOYSA-N 0.000 description 1
- LXUBLWNPXHMMGB-UHFFFAOYSA-N methyl n-(2-trityloxyethyl)carbamodithioate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCNC(=S)SC)C1=CC=CC=C1 LXUBLWNPXHMMGB-UHFFFAOYSA-N 0.000 description 1
- MOJVTGWMINQSFS-UHFFFAOYSA-N methyl n-[2-(oxan-2-yloxy)ethyl]carbamodithioate Chemical compound CSC(=S)NCCOC1CCCCO1 MOJVTGWMINQSFS-UHFFFAOYSA-N 0.000 description 1
- VDHZKIAXEMGBGI-UHFFFAOYSA-N methyl n-[2-[(2-methylpropan-2-yl)oxy]ethyl]carbamodithioate Chemical compound CSC(=S)NCCOC(C)(C)C VDHZKIAXEMGBGI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57047846A JPS58164567A (ja) | 1982-03-24 | 1982-03-24 | 異項環チオ−ル化合物とその製法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU189674B true HU189674B (en) | 1986-07-28 |
Family
ID=12786726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU83978A HU189674B (en) | 1982-03-24 | 1983-03-23 | Improved process for preparing hydroxyethyl-tetrazole-thiol |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4508909A (en, 2012) |
| JP (1) | JPS58164567A (en, 2012) |
| KR (1) | KR880001997B1 (en, 2012) |
| CA (1) | CA1192205A (en, 2012) |
| CH (1) | CH658054A5 (en, 2012) |
| DE (1) | DE3310174C2 (en, 2012) |
| ES (1) | ES8404996A1 (en, 2012) |
| FR (2) | FR2523969B1 (en, 2012) |
| GB (1) | GB2117767B (en, 2012) |
| HU (1) | HU189674B (en, 2012) |
| IT (1) | IT1162844B (en, 2012) |
| NL (1) | NL189710C (en, 2012) |
| SE (1) | SE454174B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004168775A (ja) * | 2002-11-08 | 2004-06-17 | Orchid Chemicals & Pharmaceuticals Ltd | オキサセファロスポリンの改良合成法 |
| CN102875484A (zh) * | 2012-09-18 | 2013-01-16 | 江西金顿生物科技有限公司 | 一种1-羟乙基-5-巯基-1h-四氮唑的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3778508A (en) * | 1969-11-07 | 1973-12-11 | Monsanto Co | Feed compositions and methods |
| NL7414119A (nl) * | 1973-10-31 | 1975-05-02 | Fujisawa Pharmaceutical Co | Werkwijze ter bereiding van 1h-tetrazool-5-thiol- derivaten en 1-gesubstitueerde 1h-tetrazool- -5-thiolen. |
| JPS5830316B2 (ja) * | 1973-10-31 | 1983-06-28 | 藤沢薬品工業株式会社 | １− チカン −１ｈ− テトラゾ−ル −５− チオ−ルルイノセイゾウホウ |
| JPS5812275B2 (ja) * | 1974-12-09 | 1983-03-07 | 藤沢薬品工業株式会社 | １− チカン −１ｈ− テトラゾ−ル −５− チオ−ルルイノ セイゾウホウ |
| JPS5168588A (en) * | 1974-12-09 | 1976-06-14 | Meiji Seika Co | Sefuemujudotaino shinkiseizohoho |
| BE845338A (fr) * | 1975-09-02 | 1977-02-21 | Nouvelles cephalosporines, procede pour leur obtention et application pharmaceutique | |
| US5233692A (en) * | 1990-04-06 | 1993-08-03 | Micro Technology, Inc. | Enhanced interface permitting multiple-byte parallel transfers of control information and data on a small computer system interface (SCSI) communication bus and a mass storage system incorporating the enhanced interface |
-
1982
- 1982-03-24 JP JP57047846A patent/JPS58164567A/ja active Granted
-
1983
- 1983-03-15 US US06/475,410 patent/US4508909A/en not_active Expired - Lifetime
- 1983-03-16 SE SE8301440A patent/SE454174B/sv not_active IP Right Cessation
- 1983-03-21 DE DE3310174A patent/DE3310174C2/de not_active Expired - Lifetime
- 1983-03-23 ES ES520879A patent/ES8404996A1/es not_active Expired
- 1983-03-23 IT IT67324/83A patent/IT1162844B/it active
- 1983-03-23 HU HU83978A patent/HU189674B/hu unknown
- 1983-03-23 FR FR8304761A patent/FR2523969B1/fr not_active Expired
- 1983-03-23 NL NLAANVRAGE8301039,A patent/NL189710C/xx active Search and Examination
- 1983-03-23 KR KR1019830001159A patent/KR880001997B1/ko not_active Expired
- 1983-03-24 CA CA000424337A patent/CA1192205A/en not_active Expired
- 1983-03-24 CH CH1633/83A patent/CH658054A5/de not_active IP Right Cessation
- 1983-03-24 GB GB08308127A patent/GB2117767B/en not_active Expired
- 1983-09-02 FR FR8314107A patent/FR2530240B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1192205A (en) | 1985-08-20 |
| FR2530240A1 (fr) | 1984-01-20 |
| GB8308127D0 (en) | 1983-05-05 |
| NL8301039A (nl) | 1983-10-17 |
| DE3310174A1 (de) | 1983-09-29 |
| KR880001997B1 (ko) | 1988-10-11 |
| JPS58164567A (ja) | 1983-09-29 |
| JPH0347269B2 (en, 2012) | 1991-07-18 |
| IT1162844B (it) | 1987-04-01 |
| FR2523969A1 (fr) | 1983-09-30 |
| SE8301440D0 (sv) | 1983-03-16 |
| SE454174B (sv) | 1988-04-11 |
| NL189710B (nl) | 1993-02-01 |
| ES520879A0 (es) | 1984-05-16 |
| GB2117767B (en) | 1985-07-24 |
| FR2530240B1 (fr) | 1986-04-18 |
| SE8301440L (sv) | 1983-09-25 |
| FR2523969B1 (fr) | 1986-02-28 |
| GB2117767A (en) | 1983-10-19 |
| IT8367324A0 (it) | 1983-03-23 |
| US4508909A (en) | 1985-04-02 |
| NL189710C (nl) | 1993-07-01 |
| KR840004088A (ko) | 1984-10-06 |
| DE3310174C2 (de) | 1997-02-06 |
| CH658054A5 (de) | 1986-10-15 |
| ES8404996A1 (es) | 1984-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101321522B (zh) | 环氧丁醇中间体的制备方法 | |
| US6284915B2 (en) | Process for preparing 2-amino malonic acid derivatives and 2-amino-1,3-propanediol derivatives, and intermediates for preparing the same | |
| JP2009517413A5 (en, 2012) | ||
| JPWO2006006496A1 (ja) | アズレン誘導体の製造方法及びその合成中間体 | |
| HU222017B1 (hu) | Eljárás benzopiránszármazékok előállítására | |
| HU189674B (en) | Improved process for preparing hydroxyethyl-tetrazole-thiol | |
| PT1904469E (pt) | Novos derivados de pirocatequina | |
| HU223476B1 (hu) | Új intermedierek tiolok előállításához | |
| MXPA02010022A (es) | Proceso para la preparacion de derivados de tiazolidindiona e intermediarios. | |
| JPH0321021B2 (en, 2012) | ||
| JPH0527638B2 (en, 2012) | ||
| KR100317832B1 (ko) | 4-할로-5-(히드록시메틸)이미다졸화합물의합성방법및신규이미다졸화합물 | |
| JP3573357B2 (ja) | ３−アミノ−２−ヒドロキシ−酪酸エステル誘導体を出発原料とする光学活性３−アミノ−２−ブタノール誘導体の製造法及びその中間体 | |
| WO2022094711A1 (en) | Process for preparation of advanced intermediate for eribulin synthesys | |
| KR810001650B1 (ko) | α-보호 옥시이미노-β-옥소-γ-할로게노부티르산 유도체의 제조방법 | |
| SU254519A1 (ru) | Способ получения производных триметилгидрохинона | |
| HU206499B (en) | Process for producing amino-pyrimidine derivatives | |
| WO2003080604A1 (en) | Dihydroisoxazolyl substituted tetrahydrofuran coompounds as intermediates in the preparation of 2-(purin-9-yl) - tetrahydrofuran derivatives | |
| HU184513B (en) | Process for preparing prostaglandin-f down 2 alpha-derivatives | |
| HU186368B (en) | Process for prdicing bracket-3-alpha-4-beta-5-alpha-6a alpha-bracket closed-hexahydro-5-hydroxy-4-hydroymethyl-2h-cyclopenta-square bracket-b-square bracket closed-furan-2-one derivatives | |
| HU216269B (hu) | Eljárás és köztitermékek lényegében izomertiszta E-2-[2-(aril-oxi-metil)-fenil]-krotonsav-metil-észterek előállítására |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |