SU689619A3 - Способ получени -изомера 2,6диоксиметилпиридин-бис- метилкарбамата - Google Patents
Способ получени -изомера 2,6диоксиметилпиридин-бис- метилкарбаматаInfo
- Publication number
- SU689619A3 SU689619A3 SU772446201A SU2446201A SU689619A3 SU 689619 A3 SU689619 A3 SU 689619A3 SU 772446201 A SU772446201 A SU 772446201A SU 2446201 A SU2446201 A SU 2446201A SU 689619 A3 SU689619 A3 SU 689619A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mixture
- paragraphs
- dioxymethylpyridine
- isomer
- hydrochloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- -1 halogen hydrocarbon Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- GSWAOPJLTADLTN-UHFFFAOYSA-N oxidanimine Chemical group [O-][NH3+] GSWAOPJLTADLTN-UHFFFAOYSA-N 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000013078 crystal Substances 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000012986 modification Methods 0.000 description 8
- 230000004048 modification Effects 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- OJYGBLRPYBAHRT-UHFFFAOYSA-N alphachloralose Chemical compound O1C(C(Cl)(Cl)Cl)OC2C(O)C(C(O)CO)OC21 OJYGBLRPYBAHRT-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OMSBSIXAZZRIRW-UHFFFAOYSA-N 2-methylpyridine;hydrochloride Chemical compound Cl.CC1=CC=CC=N1 OMSBSIXAZZRIRW-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- LNQCUTNLHUQZLR-VNPYQEQNSA-N Iridin Natural products O(C)c1c(O)c2C(=O)C(c3cc(OC)c(OC)c(O)c3)=COc2cc1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 LNQCUTNLHUQZLR-VNPYQEQNSA-N 0.000 description 1
- XARIFKSEVODEFM-UHFFFAOYSA-N [6-(acetyloxymethyl)pyridin-2-yl]methyl acetate Chemical compound C(C)(=O)OCC1=NC(=CC=C1)COC(C)=O XARIFKSEVODEFM-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- GEYMMMXKROUBAI-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl.Cl.Cl GEYMMMXKROUBAI-UHFFFAOYSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 108010047623 iridine Proteins 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum 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
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU76RI584A HU171664B (hu) | 1976-01-24 | 1976-01-24 | Sposob poluchenija 2,6-digidroksimetil-piridin-bis/n-metilkarbamata/ v gamma 2 kristallicheskoj forme dlja neposredstvennogo tabletirovanija |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU689619A3 true SU689619A3 (ru) | 1979-09-30 |
Family
ID=11000992
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772446201A SU689619A3 (ru) | 1976-01-24 | 1977-01-24 | Способ получени -изомера 2,6диоксиметилпиридин-бис- метилкарбамата |
| SU772559952A SU697051A3 (ru) | 1976-01-24 | 1977-12-29 | Способ получени 2,6-диоксиметилпиридин-бис-( -метилкарбамата) или кристаллической модификации |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772559952A SU697051A3 (ru) | 1976-01-24 | 1977-12-29 | Способ получени 2,6-диоксиметилпиридин-бис-( -метилкарбамата) или кристаллической модификации |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5291870A (enExample) |
| AT (1) | AT347968B (enExample) |
| CH (1) | CH638496A5 (enExample) |
| CS (1) | CS215094B2 (enExample) |
| DD (1) | DD129213A5 (enExample) |
| DE (1) | DE2702772A1 (enExample) |
| GB (1) | GB1548334A (enExample) |
| HU (1) | HU171664B (enExample) |
| PL (1) | PL106095B1 (enExample) |
| SU (2) | SU689619A3 (enExample) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT258954B (de) * | 1963-04-13 | 1967-12-27 | Michiro Inoue | Verfahren zur Herstellung neuer Bis(hydroxymethyl)pyridindicarbamat-Derivate |
| AT258953B (de) * | 1963-04-13 | 1967-12-27 | Michiro Inoue | Verfahren zur Herstellung neuer Bis(hydroxymethyl)pyridindicarbamat-Derivate |
| NL126013C (enExample) * | 1963-04-13 | 1900-01-01 | ||
| AT258955B (de) * | 1965-11-08 | 1967-12-27 | Michiro Inoue | Verfahren zur Herstellung neuer Bis(hydroxymethyl)pyridindicarbamat-Derivate |
| ES377775A1 (es) * | 1970-03-21 | 1973-06-01 | Prodes Sa | Procedimiento para la obtencion del ester bis-(n-meticarba-mico) del 2,6-piridindimetanol. |
| JPS497286A (enExample) * | 1972-05-24 | 1974-01-22 |
-
1976
- 1976-01-24 HU HU76RI584A patent/HU171664B/hu not_active IP Right Cessation
- 1976-12-31 CS CS889776A patent/CS215094B2/cs unknown
-
1977
- 1977-01-03 CH CH1177A patent/CH638496A5/de not_active IP Right Cessation
- 1977-01-17 AT AT22277A patent/AT347968B/de not_active IP Right Cessation
- 1977-01-21 GB GB257777A patent/GB1548334A/en not_active Expired
- 1977-01-21 DD DD19703377A patent/DD129213A5/xx unknown
- 1977-01-22 JP JP544277A patent/JPS5291870A/ja active Granted
- 1977-01-22 PL PL19550577A patent/PL106095B1/pl unknown
- 1977-01-24 DE DE19772702772 patent/DE2702772A1/de active Granted
- 1977-01-24 SU SU772446201A patent/SU689619A3/ru active
- 1977-12-29 SU SU772559952A patent/SU697051A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5291870A (en) | 1977-08-02 |
| HU171664B (hu) | 1978-02-28 |
| AT347968B (de) | 1979-01-25 |
| JPS6135984B2 (enExample) | 1986-08-15 |
| DD129213A5 (de) | 1978-01-04 |
| DE2702772C2 (enExample) | 1988-01-21 |
| DE2702772A1 (de) | 1977-07-28 |
| ATA22277A (de) | 1978-06-15 |
| GB1548334A (en) | 1979-07-11 |
| CH638496A5 (en) | 1983-09-30 |
| CS215094B2 (en) | 1982-07-30 |
| SU697051A3 (ru) | 1979-11-05 |
| PL106095B1 (pl) | 1979-11-30 |
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