HU186026B - Process for preparing 4-halo-dihydro-pyran-3-one derivatives - Google Patents
Process for preparing 4-halo-dihydro-pyran-3-one derivatives Download PDFInfo
- Publication number
- HU186026B HU186026B HU82156A HU15677A HU186026B HU 186026 B HU186026 B HU 186026B HU 82156 A HU82156 A HU 82156A HU 15677 A HU15677 A HU 15677A HU 186026 B HU186026 B HU 186026B
- Authority
- HU
- Hungary
- Prior art keywords
- pyran
- formula
- halo
- derivatives
- methyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- URUUZIAJVSGYRC-UHFFFAOYSA-N oxan-3-one Chemical class O=C1CCCOC1 URUUZIAJVSGYRC-UHFFFAOYSA-N 0.000 claims 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 239000007800 oxidant agent Substances 0.000 abstract description 5
- 239000011541 reaction mixture Substances 0.000 abstract description 5
- 239000007864 aqueous solution Substances 0.000 abstract description 3
- 239000000796 flavoring agent Substances 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 239000003205 fragrance Substances 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 239000002537 cosmetic Substances 0.000 abstract 1
- 235000019634 flavors Nutrition 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- -1 1-piperidinylmethyl Chemical group 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940043353 maltol Drugs 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- VEYIMQVTPXPUHA-UHFFFAOYSA-N 3-hydroxypyran-4-one Chemical compound OC1=COC=CC1=O VEYIMQVTPXPUHA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 2
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229940093503 ethyl maltol Drugs 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UABXUIWIFUZYQK-UHFFFAOYSA-N 1-(furan-2-yl)ethanol Chemical compound CC(O)C1=CC=CO1 UABXUIWIFUZYQK-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- GCJMTPVBVPMHMB-UHFFFAOYSA-N 2-acetyl-2h-pyran-5-one Chemical compound CC(=O)C1OCC(=O)C=C1 GCJMTPVBVPMHMB-UHFFFAOYSA-N 0.000 description 1
- PTJZMJOSIZKDIX-UHFFFAOYSA-N 2-acetyl-4-bromo-2h-pyran-5-one Chemical compound CC(=O)C1OCC(=O)C(Br)=C1 PTJZMJOSIZKDIX-UHFFFAOYSA-N 0.000 description 1
- MGVKFOXKPFXROH-UHFFFAOYSA-N 2-ethyl-3-hydroxy-6-methylpyran-4-one Chemical compound CCC=1OC(C)=CC(=O)C=1O MGVKFOXKPFXROH-UHFFFAOYSA-N 0.000 description 1
- BOABLGZTHBBHPW-UHFFFAOYSA-N 2-hydroxy-2h-pyran-5-one Chemical compound OC1OCC(=O)C=C1 BOABLGZTHBBHPW-UHFFFAOYSA-N 0.000 description 1
- CSEDVMRKXMDBAK-UHFFFAOYSA-N 2-methoxy-6-methyl-2h-pyran-5-one Chemical compound COC1OC(C)C(=O)C=C1 CSEDVMRKXMDBAK-UHFFFAOYSA-N 0.000 description 1
- YYRYKNXDWXDXSN-UHFFFAOYSA-N 2h-pyran-5-one Chemical compound O=C1COCC=C1 YYRYKNXDWXDXSN-UHFFFAOYSA-N 0.000 description 1
- DQYZMWTXNWIUNS-UHFFFAOYSA-N 4-bromo-2-hydroxy-2h-pyran-5-one Chemical compound OC1OCC(=O)C(Br)=C1 DQYZMWTXNWIUNS-UHFFFAOYSA-N 0.000 description 1
- DSEPAHSEUBGYDG-UHFFFAOYSA-N 4-bromo-2-hydroxy-6-methyl-2h-pyran-5-one Chemical compound CC1OC(O)C=C(Br)C1=O DSEPAHSEUBGYDG-UHFFFAOYSA-N 0.000 description 1
- SZEBFBITOQGJBK-UHFFFAOYSA-N 4-bromo-2-methoxy-6-methyl-2h-pyran-5-one Chemical compound COC1OC(C)C(=O)C(Br)=C1 SZEBFBITOQGJBK-UHFFFAOYSA-N 0.000 description 1
- TXCADDUIVINZSC-UHFFFAOYSA-N 4-bromo-6-ethyl-2-hydroxy-2h-pyran-5-one Chemical compound CCC1OC(O)C=C(Br)C1=O TXCADDUIVINZSC-UHFFFAOYSA-N 0.000 description 1
- IGMQAWRMDKAASU-UHFFFAOYSA-N 4-chloro-2-hydroxy-2h-pyran-5-one Chemical compound OC1OCC(=O)C(Cl)=C1 IGMQAWRMDKAASU-UHFFFAOYSA-N 0.000 description 1
- DHPZIGNTAGIVKP-UHFFFAOYSA-N 4-chloro-2-methoxy-6-methyl-2h-pyran-5-one Chemical compound COC1OC(C)C(=O)C(Cl)=C1 DHPZIGNTAGIVKP-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000723343 Cichorium Species 0.000 description 1
- 235000007542 Cichorium intybus Nutrition 0.000 description 1
- 102100034741 Cyclin-dependent kinase 20 Human genes 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000218652 Larix Species 0.000 description 1
- 235000005590 Larix decidua Nutrition 0.000 description 1
- 101500014379 Lymnaea stagnalis Ovulation hormone Proteins 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- DKSMCEUSSQTGBK-UHFFFAOYSA-N bromous acid Chemical compound OBr=O DKSMCEUSSQTGBK-UHFFFAOYSA-N 0.000 description 1
- 150000001719 carbohydrate derivatives Chemical class 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002243 precursor Substances 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
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical class CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Furan Compounds (AREA)
- Picture Signal Circuits (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Transforming Electric Information Into Light Information (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Processing Of Color Television Signals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Seasonings (AREA)
- Control Of El Displays (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71090176A | 1976-08-02 | 1976-08-02 | |
| US05/721,885 US4082717A (en) | 1976-08-02 | 1976-09-09 | Preparation of gamma-pyrones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU186026B true HU186026B (en) | 1985-05-28 |
Family
ID=27108548
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU82155A HU185686B (en) | 1976-08-02 | 1977-07-21 | Process for preparing gamma-pyrone derivatives |
| HU82157A HU185687B (en) | 1976-08-02 | 1977-07-21 | Process for producing gamma-pyrone derivatives |
| HU82156A HU186026B (en) | 1976-08-02 | 1977-07-21 | Process for preparing 4-halo-dihydro-pyran-3-one derivatives |
| HU77PI584A HU180040B (en) | 1976-08-02 | 1977-07-21 | Process for producing 3-hydroxy-gamma-pyrone derivatives |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU82155A HU185686B (en) | 1976-08-02 | 1977-07-21 | Process for preparing gamma-pyrone derivatives |
| HU82157A HU185687B (en) | 1976-08-02 | 1977-07-21 | Process for producing gamma-pyrone derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU77PI584A HU180040B (en) | 1976-08-02 | 1977-07-21 | Process for producing 3-hydroxy-gamma-pyrone derivatives |
Country Status (36)
| Country | Link |
|---|---|
| JP (7) | JPS5318578A (nl) |
| AR (1) | AR216080A1 (nl) |
| AT (3) | AT362790B (nl) |
| BE (1) | BE855965A (nl) |
| BG (4) | BG29136A3 (nl) |
| BR (1) | BR7703970A (nl) |
| CA (3) | CA1095921A (nl) |
| CH (4) | CH625798A5 (nl) |
| CS (3) | CS203921B2 (nl) |
| DD (1) | DD132494A5 (nl) |
| DE (3) | DE2760220C2 (nl) |
| DK (4) | DK153483C (nl) |
| EG (1) | EG13080A (nl) |
| ES (5) | ES459994A1 (nl) |
| FI (6) | FI72722C (nl) |
| FR (1) | FR2372821A1 (nl) |
| GB (5) | GB1538374A (nl) |
| GR (1) | GR68938B (nl) |
| HK (5) | HK30681A (nl) |
| HU (4) | HU185686B (nl) |
| IE (5) | IE45642B1 (nl) |
| IT (1) | IT1106258B (nl) |
| LU (1) | LU77600A1 (nl) |
| MX (1) | MX4597E (nl) |
| MY (3) | MY8100262A (nl) |
| NL (5) | NL170955C (nl) |
| NO (7) | NO150561C (nl) |
| NZ (1) | NZ184342A (nl) |
| PH (5) | PH13557A (nl) |
| PL (4) | PL115497B1 (nl) |
| PT (1) | PT66694B (nl) |
| RO (4) | RO74367A (nl) |
| SE (6) | SE433079B (nl) |
| SU (2) | SU955859A3 (nl) |
| TR (1) | TR19652A (nl) |
| YU (4) | YU40166B (nl) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1095921A (en) * | 1976-08-02 | 1981-02-17 | Thomas M. Brennan | Preparation of gamma-pyrones |
| FR2402654A1 (fr) * | 1977-09-12 | 1979-04-06 | Shinetsu Chemical Co | Nouveaux derives de x tetrahydropyrannone(5) |
| JPS5444675A (en) * | 1977-09-12 | 1979-04-09 | Shin Etsu Chem Co Ltd | Production of 3-hydroxy-4-pyrone analog |
| JPS5741226U (nl) * | 1980-08-20 | 1982-03-05 | ||
| JPS59135008U (ja) * | 1983-02-28 | 1984-09-10 | 松下電工株式会社 | 分電盤装置 |
| JPS6050245A (ja) * | 1983-08-29 | 1985-03-19 | Nissan Motor Co Ltd | 内燃機関の燃料噴射装置 |
| JPH0226945Y2 (nl) * | 1985-09-11 | 1990-07-20 | ||
| JP2586607B2 (ja) * | 1987-10-30 | 1997-03-05 | 日産化学工業株式会社 | 光学活性アルコールの製造法 |
| AU2008232262B2 (en) * | 2007-03-28 | 2013-02-14 | Apotex Inc. | Fluorinated derivatives of deferiprone |
| UA102254C2 (ru) | 2008-04-25 | 2013-06-25 | Апотекс Технолоджис Инк. | Жидкий состав для деферипрона с приятным вкусом |
| JP5611339B2 (ja) | 2009-07-03 | 2014-10-22 | アポテックス テクノロジーズ インク．Ａｐｏｔｅｘ Ｔｅｃｈｎｏｌｏｇｉｅｓ Ｉｎｃ． | ３−ヒドロキシピリジン‐４−オンのフッ素化誘導体 |
| WO2017168309A1 (en) * | 2016-03-29 | 2017-10-05 | Dr. Reddy’S Laboratories Limited | Process for preparation of eribulin and intermediates thereof |
| CN108609456B (zh) * | 2016-12-13 | 2021-03-12 | 奥的斯电梯公司 | 可打开扩展面板及具有其的电梯吊顶，轿厢和系统 |
| CN111606879A (zh) * | 2020-05-25 | 2020-09-01 | 安徽金禾实业股份有限公司 | 一锅法制备2-羟甲基-3-烷氧基-4h-吡喃-4-酮的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3491122A (en) * | 1966-09-14 | 1970-01-20 | Monsanto Co | Synthesis of 4-pyrones |
| US3547912A (en) * | 1968-07-29 | 1970-12-15 | American Home Prod | Derivatives of 2h-pyran-3(6h)-ones and preparation thereof |
| JPS5145565B1 (nl) * | 1968-10-12 | 1976-12-04 | ||
| US3621063A (en) * | 1968-12-24 | 1971-11-16 | Monsanto Co | Unsaturated acyclic ketones |
| US3832357A (en) * | 1971-05-26 | 1974-08-27 | Daicel Ltd | Process for preparation of 3-hydroxy-2-alkyl-4-pyrone |
| JPS5212166A (en) * | 1975-07-17 | 1977-01-29 | Tatsuya Shono | Process for preparation of 4-pyron derivatives |
| IE42789B1 (en) * | 1975-08-28 | 1980-10-22 | Pfizer | Preparation of gamma-pyrones |
| CA1095921A (en) * | 1976-08-02 | 1981-02-17 | Thomas M. Brennan | Preparation of gamma-pyrones |
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1977
- 1977-06-06 CA CA279,922A patent/CA1095921A/en not_active Expired
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- 1977-07-21 PL PL1977199798A patent/PL115586B1/pl unknown
- 1977-07-21 GB GB4243/78A patent/GB1538375A/en not_active Expired
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1978
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- 1978-05-25 JP JP53062820A patent/JPS5814433B2/ja not_active Expired
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- 1978-06-13 ES ES470746A patent/ES470746A1/es not_active Expired
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- 1978-07-05 SU SU782631651A patent/SU1015826A3/ru active
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1979
- 1979-02-01 PH PH22150A patent/PH13874A/en unknown
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1980
- 1980-03-06 AT AT0124480A patent/AT363470B/de not_active IP Right Cessation
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1981
- 1981-02-20 CH CH116081A patent/CH626357A5/fr not_active IP Right Cessation
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- 1981-12-09 NL NLAANVRAGE8105540,A patent/NL182805C/nl not_active IP Right Cessation
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1982
- 1982-01-29 SE SE8200520A patent/SE444564B/sv not_active IP Right Cessation
- 1982-01-29 SE SE8200518A patent/SE445041B/sv not_active IP Right Cessation
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- 1982-06-03 NO NO821849A patent/NO150559C/no unknown
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1983
- 1983-05-16 FI FI831700A patent/FI72119C/fi not_active IP Right Cessation
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1986
- 1986-07-09 DK DK326086A patent/DK153401C/da not_active IP Right Cessation
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