NO150560B - 6,6`-oksybis-halogensubstituert-pyron-derivater og fremgangsmaae for fremstilling derav - Google Patents
6,6`-oksybis-halogensubstituert-pyron-derivater og fremgangsmaae for fremstilling derav Download PDFInfo
- Publication number
- NO150560B NO150560B NO821851A NO821851A NO150560B NO 150560 B NO150560 B NO 150560B NO 821851 A NO821851 A NO 821851A NO 821851 A NO821851 A NO 821851A NO 150560 B NO150560 B NO 150560B
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- Prior art keywords
- formula
- oxybis
- halogen
- substituted
- compound
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 7
- NQBKFULMFQMZBE-UHFFFAOYSA-N n-bz-3-benzanthronylpyrazolanthron Chemical class C12=CC=CC(C(=O)C=3C4=CC=CC=3)=C2C4=NN1C1=CC=C2C3=C1C1=CC=CC=C1C(=O)C3=CC=C2 NQBKFULMFQMZBE-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 16
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 7
- 229940043353 maltol Drugs 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- UABXUIWIFUZYQK-UHFFFAOYSA-N 1-(furan-2-yl)ethanol Chemical compound CC(O)C1=CC=CO1 UABXUIWIFUZYQK-UHFFFAOYSA-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
- 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 2
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 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
- 239000003623 enhancer Substances 0.000 description 2
- 229940093503 ethyl maltol Drugs 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YQIUCEVQCDXCBS-UHFFFAOYSA-N 4-bromo-2-[(4-bromo-6-methyl-5-oxo-2h-pyran-2-yl)oxy]-6-methyl-2h-pyran-5-one Chemical compound C1=C(Br)C(=O)C(C)OC1OC1C=C(Br)C(=O)C(C)O1 YQIUCEVQCDXCBS-UHFFFAOYSA-N 0.000 description 1
- -1 6-methyl-2-ethyl-3-hydroxy-4H-pyran- Chemical compound 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000723343 Cichorium Species 0.000 description 1
- 235000007542 Cichorium intybus Nutrition 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
- 235000019502 Orange oil Nutrition 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 150000001719 carbohydrate derivatives Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 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
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Picture Signal Circuits (AREA)
- Transforming Electric Information Into Light Information (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Processing Of Color Television Signals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Seasonings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Control Of El Displays (AREA)
Abstract
6,6'-oksybis-halogensubstituert-pyron-derivater . og fremgangsmåte for fremstilling derav.
Description
Foreliggende oppfinnelse gjelder nye 6,6 '-oksybis-halogensubstituert-pyron-derivater egnet for anvendelse som mellomprodukter ved fremstilling av gamma-pyroner, samt en fremgangsmåte for fremstilling derav.
Fremstilling av gamma-pyroner ved hydrolyse av mellomproduktene ifølge oppfinnelsen er beskrevet i patentsøknad 77.2193.
Maltol (2-metyl-3-hydroksy-4H-pyran-4-on) er en naturlig forekommende substans funnet i barken hos unge lerketrær, furu-nåler og sikori. Tidlig kommersiell produksjon foregikk ved destruktiv destillasjon av ved. Syntesen av maltol fra 3- hydroksy-2-(1-piperidylmetyl)-1,4-pyron ble omtalt av Spielman og Freifelder i J. Am. Chem. Soc, 69, 2908 (1947). Schenck og J. Am. Chem. Soc, 67, 2267 (1945) oppnådde maltol
ved alkalisk hydrolyse av streptomycinsalter. Chawla og McGonigal, J. Org. Chem., 39, 3281 (1974) og Lichtenthaler
og Heidel, Angew. Chem., 81, 998 (1969), omtalte syntese av maltol fra beskyttende karbohydrat-derivater. Shono og Matsumura, Tetrahedron Letters nr. 17, 1363 (1976), beskrev
en fem trinns syntese av maltol utgående fra metylfurfurylalkohol.
Isoleringen av 6-metyl-2-etyl-3-hydroksy-4H-pyran-
4- on som en av de karakteristiske søt-aromabestanddelene i raffinert, ferdig melasse bie omtalt av Hiroshi Ito i Agr.
Biol. Chem., 40 (5), 827-832 (1976). Denne forbindelse ble tidligere syntetisert ved hjelp av den fremgangsmåte som er beskrevet i US-patent 3.468.915.
Synteser av gamma-pyroner som f.eks. pyromekonsyre,
maltol, etylmaltol og andre 2-substituerte 3-hydroksy-gamma-pyroner er beskrevet i US-patenter 3.130.204, 3.133.089,
3.140.239, 3.159.652, 3.365.469, 3.376.317, 3.440.183,
3.446.629 og 3.468.915.
Maltol og etylmaltol øker smak og aroma for for-
skjellige næringsmidler. I tillegg brukes disse forbindelser som ingredienser i parfymer og essenser. De 2-alkenylpyromekon-syrer som er beskrevet i US-patent 3.64 4.6 35 og de 2-arylmetyl-pyromekonsyrer som er beskrevet i US-patent 3.365.469 hindrer vekst av bakterier og sopper og er anvendbare som smaks- og aromaøkende midler i næringsmidler og drikker og aromaøkende midler i parfymer.
Patentsøknad 77..2193 beskriver en fremgangsmåte for fremstilling av et gamma-pyron med formelen
som omfatter oppvarmning i sur, vandig løsning, fortrinnsvis ved en temperatur i området 70 til 160°C, inntil hydrolysen er i hovedsak fullstendig, av bl.a. et 6,6'-oksybis[4-halogen-2H-pyran-3(6H)-on] med formel (V):
hvor R bl.a. er hydrogen eller alkyl med 1 til 4 karbonatomer, R''<*> bl.a. er hydrogen og X er klor eller brom.
Den syre som kreves for hydrolysen kan tilsettes til reaksjonsblandingen, f.eks. ved å oppløse mellomproduktet med formel (V) i en vandig, uorganisk eller organisk syre før oppvarmningen; eller alternativt kan syren genereres in situ under fremstillingen av mellomproduktene som beskrevet senere.
Noen av forbindelsene med formel (V) er nye, og ifølge oppfinnelsen tilveiebringes forbindelser med formel
(V):
hvor R er hydrogen.eller alkyl med 1 til 4 karbonatomer, og X er klor eller brom.
Ifølge oppfinnelsen fremstilles det nye mellomprodukt med formel (V) ved å dehydratisere en forbindelse med formelen:
hvor R og X er som ovenfor angitt, ved 40°C.
Dehydratiseringen utføres fortrinnsvis ved oppvarmning av forbindelsen med formel II" ved en temperatur på 40°C i 16 timer.
Som beskrevet i patentsøknad 77.219 3 kan utgangs-forbindelsen med formel (II") fremstilles ved omsetning av en furfurylalkohol i vandig løsning sammen med et eventuelt ko-løsningsmiddel ved -10 til 10°C med to ekvivalenter av et halogenholdig oksydasjonsmiddel. Det foretrukne halogen-holdige oksydasjonsmiddel er klor eller bromklorid. Efter omrøring ved romtemperatur i 30 minutter reguleres reaksjons-blandingens pH-verdi til 2 med en sterk base, og reaksjonsblandingen ekstraheres med et løsningsmiddel så som etylacetat. Fjernelse av løsningsmidlet gir 4-halogen-6-hydroksy-2H-pyran-3(6H)-on-forbindelsen med formel (II") som kan dehydratiseres ved oppvarmning under vakuum for å gi 6,6'-oksybis-[4-halogen-2H-pyran-3(6H)-on]-forbindelsen.
Følgende eksempler illustrerer fremstillingen av de nye mellomproduktene ved fremgangsmåten ifølge oppfinnelsen.
I spektraldataene angitt i eksempel l(a) er kjemiske NMR-skift-data angitt ved hjelp av konvensjonell litteratur-symbolisme, og alle skift er uttrykt som 6-enheter fra tetrametylsilan:
d = dublett
q = kvartett
m = multiplett
Eksempel 1
a) Fremstilling av 4- brom- 6- hydroksy- 2- metyl- 2H- pyran-3( 6H)- on ( utgangsmateriale)
Til en løsning av 25 g 1-(2-furyl)-1-etanol i 125 ml tetrahydrofuran og 125 ml vann ved 0 til 5°C ble tilsatt dråpevis 2,2 ekvivalenter brom. Under tilsetningen ble temperaturen holdt ved 5 til 10°C. Efter bromtilsetningen ble løsningen om-rørt ved romtemperatur i 30 minutter og pH justert til 2,1 med 2N NaOH-løsning. Reaksjonsblandingen ble ekstrahert med etylacetat (3 x 100 ml). Etylacetatekstraktene ble kombinert, tørket over MgSO^, filtrert og inndampet til tørrhet. Residuet ble kromatografert på silikagel og eluert med klorofqrm-etylacetat (95:5). Produktet var en oransje olje som ble om-kromatografert på silikagel og eluert med klorofprm-etylacetat (95:5) .
NMR (CDC13, 6) 7,3 (1H, d); 5,6 (1H, d); 4,7-5,0 (1H, q); 1,1-1,5 (3H, m).
b) Fremstilling av sluttprodukt
4-brom-6-hydroksy-2-metyl-2H-pyran-3(6H)-on ble
oppvarmet under vakuum i 16 timer ved 40°C. Det resulterende oljeaktige faste stoff ble krystallisert fra isopropylalkohol for å gi 6,6'-oksybis[4-brom-2-metyl-2H-pyran-3(6H)-on],
sm.p. 125°C.
Eksempel 2
Fremgangsmåten fra eksempel 1 ble gjentatt ved å gå ut fra en forbindelse med formelen: hvor R er metyl eller etyl, for å gi en forbindelse med formelen:
Claims (3)
1. 6,6'-oksybis[4-halogen-2H-pyran-3(6H)-on]-forbindelse for anvendelse som mellomprodukt ved fremstilling av gamma-pyroner med formelen 0
(mT'0H
hvor R er hydrogen eller alkyl med 1 til 4 karbonatomer, karakterisert ved formelen:
X X
hvor R er som ovenfor angitt, og X er klor eller brom.
2. Fremgangsmåte for fremstilling av 6,6'-oksybis[4-halogen-2H-pyran-3(6H)-on]-forbindelse med formelen:
X X
hvor R er hydrogen eller alkyl med 1 til 4 karbonatomer, og X er klor eller brom, karakterisert ved at en forbindelse med formelen:
X /C^C (ir,)
HO 0 R
hvor R og X er som angitt ovenfor, dehydratiseres ved 40°C.
3. Fremgangsmåte ifølge krav 2,
karakterisert ved at dehydratiseringen utføres ved oppvarmning av forbindelsen med formel (II") ved en temperatur på 40°C i 16 timer under vakuum.
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 (3)
| Publication Number | Publication Date |
|---|---|
| NO821851L NO821851L (no) | 1978-02-03 |
| NO150560B true NO150560B (no) | 1984-07-30 |
| NO150560C NO150560C (no) | 1984-11-07 |
Family
ID=27108548
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO772193A NO150561C (no) | 1976-08-02 | 1977-06-22 | Fremgangsmaate for fremstilling av gamma-pyroner |
| NO821849A NO150559C (no) | 1976-08-02 | 1982-06-03 | 4-halogen-dihydropyran-forbindelser og fremgangsmaate for fremstilling derav |
| NO821851A NO150560C (no) | 1976-08-02 | 1982-06-03 | 6,6`-oksybis-halogensubstituert-pyron-derivater og fremgangsmaae for fremstilling derav |
| NO821850A NO821850L (no) | 1976-08-02 | 1982-06-03 | Fremgangsmaate for fremstilling av 4-halogen-dihydropyran-derivater |
| NO821847A NO150042C (no) | 1976-08-02 | 1982-06-03 | Fremgangsmaate for fremstilling av gamma-pyroner |
| NO821848A NO150043C (no) | 1976-08-02 | 1982-06-03 | Fremgangsmaate for fremstilling av gamma-pyroner |
| NO834236A NO151365C (no) | 1976-08-02 | 1983-11-18 | Fremgangsmaate for fremstilling av 4-halogen-dihydropyran-derivater. |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO772193A NO150561C (no) | 1976-08-02 | 1977-06-22 | Fremgangsmaate for fremstilling av gamma-pyroner |
| NO821849A NO150559C (no) | 1976-08-02 | 1982-06-03 | 4-halogen-dihydropyran-forbindelser og fremgangsmaate for fremstilling derav |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO821850A NO821850L (no) | 1976-08-02 | 1982-06-03 | Fremgangsmaate for fremstilling av 4-halogen-dihydropyran-derivater |
| NO821847A NO150042C (no) | 1976-08-02 | 1982-06-03 | Fremgangsmaate for fremstilling av gamma-pyroner |
| NO821848A NO150043C (no) | 1976-08-02 | 1982-06-03 | Fremgangsmaate for fremstilling av gamma-pyroner |
| NO834236A NO151365C (no) | 1976-08-02 | 1983-11-18 | Fremgangsmaate for fremstilling av 4-halogen-dihydropyran-derivater. |
Country Status (36)
| Country | Link |
|---|---|
| JP (7) | JPS5318578A (no) |
| AR (1) | AR216080A1 (no) |
| AT (3) | AT362790B (no) |
| BE (1) | BE855965A (no) |
| BG (4) | BG28988A4 (no) |
| BR (1) | BR7703970A (no) |
| CA (3) | CA1095921A (no) |
| CH (4) | CH625798A5 (no) |
| CS (3) | CS203921B2 (no) |
| DD (1) | DD132494A5 (no) |
| DE (3) | DE2728499C2 (no) |
| DK (4) | DK153483C (no) |
| EG (1) | EG13080A (no) |
| ES (5) | ES459994A1 (no) |
| FI (6) | FI72722C (no) |
| FR (1) | FR2372821A1 (no) |
| GB (5) | GB1538375A (no) |
| GR (1) | GR68938B (no) |
| HK (5) | HK30381A (no) |
| HU (4) | HU186026B (no) |
| IE (5) | IE45641B1 (no) |
| IT (1) | IT1106258B (no) |
| LU (1) | LU77600A1 (no) |
| MX (1) | MX4597E (no) |
| MY (3) | MY8100287A (no) |
| NL (5) | NL170955C (no) |
| NO (7) | NO150561C (no) |
| NZ (1) | NZ184342A (no) |
| PH (5) | PH13557A (no) |
| PL (4) | PL215008A1 (no) |
| PT (1) | PT66694B (no) |
| RO (4) | RO78951A2 (no) |
| SE (6) | SE433079B (no) |
| SU (2) | SU955859A3 (no) |
| TR (1) | TR19652A (no) |
| YU (4) | YU40166B (no) |
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 (no) * | 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 (no) * | 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 |
| NZ600874A (en) | 2007-03-28 | 2013-01-25 | Apotex Technologies Inc | Fluorinated derivatives of deferiprone |
| AP2010005454A0 (en) | 2008-04-25 | 2010-12-31 | Apotex Technologies Inc | Liquid formulation for deferiprone with palatable taste. |
| CN102712591B (zh) | 2009-07-03 | 2014-06-25 | 阿普泰克斯科技公司 | 3-羟基吡啶-4-酮的氟化衍生物 |
| 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 (no) * | 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
- 1977-06-08 NZ NZ184342A patent/NZ184342A/xx unknown
- 1977-06-09 GR GR53666A patent/GR68938B/el unknown
- 1977-06-13 YU YU1469/77A patent/YU40166B/xx unknown
- 1977-06-15 MX MX775807U patent/MX4597E/es unknown
- 1977-06-16 JP JP7157277A patent/JPS5318578A/ja active Granted
- 1977-06-16 SE SE7707035A patent/SE433079B/xx not_active IP Right Cessation
- 1977-06-17 PH PH19887A patent/PH13557A/en unknown
- 1977-06-20 BR BR7703970A patent/BR7703970A/pt unknown
- 1977-06-21 FI FI771934A patent/FI72722C/fi not_active IP Right Cessation
- 1977-06-21 NL NLAANVRAGE7706811,A patent/NL170955C/xx not_active IP Right Cessation
- 1977-06-21 BE BE1008209A patent/BE855965A/xx not_active IP Right Cessation
- 1977-06-22 DE DE2728499A patent/DE2728499C2/de not_active Expired
- 1977-06-22 AT AT0440477A patent/AT362790B/de not_active IP Right Cessation
- 1977-06-22 NO NO772193A patent/NO150561C/no unknown
- 1977-06-22 EG EG371/77A patent/EG13080A/xx active
- 1977-06-22 TR TR19652A patent/TR19652A/xx unknown
- 1977-06-22 ES ES459994A patent/ES459994A1/es not_active Expired
- 1977-06-22 DE DE2760220A patent/DE2760220C2/de not_active Expired
- 1977-06-22 DE DE2760221A patent/DE2760221C2/de not_active Expired
- 1977-06-22 PT PT66694A patent/PT66694B/pt unknown
- 1977-06-22 DK DK276177A patent/DK153483C/da active
- 1977-06-22 LU LU77600A patent/LU77600A1/xx unknown
- 1977-06-22 CH CH765877A patent/CH625798A5/fr not_active IP Right Cessation
- 1977-06-23 FR FR7719250A patent/FR2372821A1/fr active Granted
- 1977-06-23 IT IT49950/77A patent/IT1106258B/it active
- 1977-06-23 AR AR268164A patent/AR216080A1/es active
- 1977-06-23 DD DD7700199657A patent/DD132494A5/xx not_active IP Right Cessation
- 1977-07-14 BG BG7742606A patent/BG28988A4/xx unknown
- 1977-07-14 BG BG042608A patent/BG29136A3/xx unknown
- 1977-07-14 BG BG036892A patent/BG28849A3/xx unknown
- 1977-07-14 BG BG7942607A patent/BG28989A4/xx unknown
- 1977-07-14 CS CS774705A patent/CS203921B2/cs unknown
- 1977-07-20 RO RO7799825A patent/RO78951A2/ro unknown
- 1977-07-20 RO RO7799826A patent/RO78952A/ro unknown
- 1977-07-20 RO RO7799830A patent/RO78953A/ro unknown
- 1977-07-20 RO RO7791106A patent/RO74367A/ro unknown
- 1977-07-21 SU SU772508256A patent/SU955859A3/ru active
- 1977-07-21 HU HU82156A patent/HU186026B/hu unknown
- 1977-07-21 HU HU82155A patent/HU185686B/hu unknown
- 1977-07-21 PL PL21500877A patent/PL215008A1/xx unknown
- 1977-07-21 GB GB4243/78A patent/GB1538375A/en not_active Expired
- 1977-07-21 GB GB4241/78A patent/GB1538373A/en not_active Expired
- 1977-07-21 PL PL1977215006A patent/PL115497B1/pl unknown
- 1977-07-21 HU HU77PI584A patent/HU180040B/hu unknown
- 1977-07-21 PL PL1977215007A patent/PL115496B1/pl unknown
- 1977-07-21 PL PL1977199798A patent/PL115586B1/pl unknown
- 1977-07-21 GB GB30759/77A patent/GB1538371A/en not_active Expired
- 1977-07-21 HU HU82157A patent/HU185687B/hu unknown
- 1977-07-21 GB GB4242/78A patent/GB1538374A/en not_active Expired
- 1977-07-21 GB GB4240/78A patent/GB1538372A/en not_active Expired
- 1977-07-29 IE IE1587/77A patent/IE45641B1/en not_active IP Right Cessation
- 1977-07-29 IE IE587/79A patent/IE45645B1/en not_active IP Right Cessation
- 1977-07-29 IE IE585/79A patent/IE45643B1/en not_active IP Right Cessation
- 1977-07-29 IE IE586/79A patent/IE45644B1/en not_active IP Right Cessation
- 1977-07-29 IE IE584/79A patent/IE45642B1/en not_active IP Right Cessation
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1978
- 1978-02-03 PH PH20745A patent/PH15185A/en unknown
- 1978-02-03 PH PH20746A patent/PH13926A/en unknown
- 1978-05-25 JP JP6281878A patent/JPS5436267A/ja active Granted
- 1978-05-25 JP JP6281978A patent/JPS5436268A/ja active Pending
- 1978-05-25 JP JP6282178A patent/JPS5436270A/ja active Granted
- 1978-05-25 JP JP53062820A patent/JPS5814433B2/ja not_active Expired
- 1978-05-25 JP JP6282278A patent/JPS5436271A/ja active Granted
- 1978-05-25 JP JP6281778A patent/JPS5436266A/ja active Pending
- 1978-06-07 CS CS783706A patent/CS203923B2/cs unknown
- 1978-06-07 CS CS783705A patent/CS203922B2/cs unknown
- 1978-06-13 ES ES470745A patent/ES470745A1/es not_active Expired
- 1978-06-13 ES ES470744A patent/ES470744A1/es not_active Expired
- 1978-06-13 ES ES470746A patent/ES470746A1/es not_active Expired
- 1978-06-13 ES ES470743A patent/ES470743A1/es not_active Expired
- 1978-07-05 SU SU782631651A patent/SU1015826A3/ru active
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1979
- 1979-02-01 PH PH22150A patent/PH13874A/en unknown
- 1979-02-01 PH PH22149A patent/PH14625A/en unknown
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1980
- 1980-03-06 AT AT0124480A patent/AT363470B/de not_active IP Right Cessation
- 1980-03-06 AT AT0124380A patent/AT364356B/de not_active IP Right Cessation
- 1980-10-24 CA CA000363274A patent/CA1117541A/en not_active Expired
- 1980-10-24 CA CA363,273A patent/CA1110254A/en not_active Expired
- 1980-10-30 CH CH808580A patent/CH625235A5/fr not_active IP Right Cessation
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1981
- 1981-02-20 CH CH116081A patent/CH626357A5/fr not_active IP Right Cessation
- 1981-02-20 CH CH116181A patent/CH626358A5/fr not_active IP Right Cessation
- 1981-07-02 HK HK303/81A patent/HK30381A/xx unknown
- 1981-07-02 HK HK305/81A patent/HK30581A/xx unknown
- 1981-07-02 HK HK304/81A patent/HK30481A/xx unknown
- 1981-07-02 HK HK306/81A patent/HK30681A/xx unknown
- 1981-07-02 HK HK307/81A patent/HK30781A/xx unknown
- 1981-12-09 NL NLAANVRAGE8105540,A patent/NL182805C/xx not_active IP Right Cessation
- 1981-12-09 NL NLAANVRAGE8105538,A patent/NL182477C/xx not_active IP Right Cessation
- 1981-12-09 NL NLAANVRAGE8105537,A patent/NL182476C/xx not_active IP Right Cessation
- 1981-12-09 NL NLAANVRAGE8105539,A patent/NL182478C/xx not_active IP Right Cessation
- 1981-12-30 MY MY287/81A patent/MY8100287A/xx unknown
- 1981-12-30 MY MY267/81A patent/MY8100267A/xx unknown
- 1981-12-30 MY MY262/81A patent/MY8100262A/xx unknown
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1982
- 1982-01-29 SE SE8200520A patent/SE444564B/sv not_active IP Right Cessation
- 1982-01-29 SE SE8200519A patent/SE445042B/sv not_active IP Right Cessation
- 1982-01-29 SE SE8200521A patent/SE452616B/sv not_active IP Right Cessation
- 1982-01-29 SE SE8200522A patent/SE444565B/sv not_active IP Right Cessation
- 1982-01-29 SE SE8200518A patent/SE445041B/sv not_active IP Right Cessation
- 1982-06-03 NO NO821849A patent/NO150559C/no unknown
- 1982-06-03 NO NO821851A patent/NO150560C/no unknown
- 1982-06-03 NO NO821850A patent/NO821850L/no unknown
- 1982-06-03 NO NO821847A patent/NO150042C/no unknown
- 1982-06-03 NO NO821848A patent/NO150043C/no unknown
- 1982-12-07 YU YU02703/82A patent/YU270382A/xx unknown
- 1982-12-13 YU YU2747/82A patent/YU42613B/xx unknown
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1983
- 1983-05-16 FI FI831702A patent/FI72720C/fi not_active IP Right Cessation
- 1983-05-16 FI FI831703A patent/FI73424C/fi not_active IP Right Cessation
- 1983-05-16 FI FI831704A patent/FI72721C/fi not_active IP Right Cessation
- 1983-05-16 FI FI831701A patent/FI72723C/fi not_active IP Right Cessation
- 1983-05-16 FI FI831700A patent/FI72119C/fi not_active IP Right Cessation
- 1983-08-08 YU YU1663/83A patent/YU43190B/xx unknown
- 1983-11-18 NO NO834236A patent/NO151365C/no unknown
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1986
- 1986-07-09 DK DK325986A patent/DK153484C/da active
- 1986-07-09 DK DK326086A patent/DK153401C/da not_active IP Right Cessation
- 1986-07-09 DK DK326186A patent/DK154079C/da active
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