CA1049006A - Derives de d-xylofuranose et une methode pour leur preparation - Google Patents

Derives de d-xylofuranose et une methode pour leur preparation

Info

Publication number: CA1049006A
Authority: CA; Canada
Prior art keywords: formula; compound; benzyl; xylofuranose; iii
Prior art date: 1973-12-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA74216575A

Other languages

English (en)

Other versions

CA216575S (en

Inventor

Arpad Gerecs

Margit Barta

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chinoin Private Co Ltd

Original Assignee

Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-12-22

Filing date

1974-12-20

Publication date

1979-02-20

1974-12-20 Application filed by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

1979-02-20 Application granted granted Critical

1979-02-20 Publication of CA1049006A publication Critical patent/CA1049006A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 27
150000000897 D-xylofuranose derivatives Chemical class 0.000 title claims abstract description 20
238000002360 preparation method Methods 0.000 title claims abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 58
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 51
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical class ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
235000019445 benzyl alcohol Nutrition 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
239000011734 sodium Substances 0.000 claims description 14
229910052708 sodium Inorganic materials 0.000 claims description 14
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
-1 polymethylene group Polymers 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
239000003377 acid catalyst Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
HMFHBZSHGGEWLO-IOVATXLUSA-N D-xylofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H]1O HMFHBZSHGGEWLO-IOVATXLUSA-N 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
150000008220 D-xylofuranosides Chemical class 0.000 claims description 2
LFQULJPVXNYWAG-UHFFFAOYSA-N sodium;phenylmethanolate Chemical compound [Na]OCC1=CC=CC=C1 LFQULJPVXNYWAG-UHFFFAOYSA-N 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
230000001476 alcoholic effect Effects 0.000 claims 1
230000032050 esterification Effects 0.000 claims 1
238000005886 esterification reaction Methods 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
238000001953 recrystallisation Methods 0.000 claims 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 claims 1
125000001931 aliphatic group Chemical group 0.000 abstract description 3
208000037273 Pathologic Processes Diseases 0.000 abstract description 2
230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
230000009054 pathological process Effects 0.000 abstract description 2
208000037997 venous disease Diseases 0.000 abstract description 2
229950005499 carbon tetrachloride Drugs 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
229960004217 benzyl alcohol Drugs 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
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
230000015572 biosynthetic process Effects 0.000 description 3
229940093499 ethyl acetate Drugs 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000004856 capillary permeability Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000002242 furanose derivatives Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA74216575A 1973-12-22 1974-12-20 Derives de d-xylofuranose et une methode pour leur preparation Expired CA1049006A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUCI1427A HU169665B (fr)	1973-12-22	1973-12-22

Publications (1)

Publication Number	Publication Date
CA1049006A true CA1049006A (fr)	1979-02-20

Family

ID=10994497

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA74216575A Expired CA1049006A (fr)	1973-12-22	1974-12-20	Derives de d-xylofuranose et une methode pour leur preparation

Country Status (12)

Country	Link
JP (1)	JPS50100033A (fr)
AT (1)	AT343685B (fr)
CA (1)	CA1049006A (fr)
CH (1)	CH614719A5 (fr)
DE (1)	DE2460938A1 (fr)
DK (1)	DK651174A (fr)
FR (1)	FR2255312B1 (fr)
GB (1)	GB1472320A (fr)
HU (1)	HU169665B (fr)
IN (1)	IN141281B (fr)
PL (1)	PL95461B1 (fr)
SE (1)	SE7415952L (fr)

1973
- 1973-12-22 HU HUCI1427A patent/HU169665B/hu unknown
1974
- 1974-12-09 AT AT979874A patent/AT343685B/de not_active IP Right Cessation
- 1974-12-13 DK DK651174A patent/DK651174A/da not_active Application Discontinuation
- 1974-12-18 SE SE7415952A patent/SE7415952L/xx unknown
- 1974-12-18 IN IN2797/CAL/1974A patent/IN141281B/en unknown
- 1974-12-20 CA CA74216575A patent/CA1049006A/fr not_active Expired
- 1974-12-20 FR FR7442259A patent/FR2255312B1/fr not_active Expired
- 1974-12-20 JP JP49145822A patent/JPS50100033A/ja active Pending
- 1974-12-20 CH CH1713274A patent/CH614719A5/xx not_active IP Right Cessation
- 1974-12-21 DE DE19742460938 patent/DE2460938A1/de active Pending
- 1974-12-21 PL PL1974176729A patent/PL95461B1/pl unknown
- 1974-12-23 GB GB5560174A patent/GB1472320A/en not_active Expired

Also Published As

Publication number	Publication date
SE7415952L (fr)	1975-06-23
PL95461B1 (pl)	1977-10-31
FR2255312A1 (fr)	1975-07-18
AT343685B (de)	1978-06-12
IN141281B (fr)	1977-02-12
HU169665B (fr)	1977-02-28
CH614719A5 (en)	1979-12-14
FR2255312B1 (fr)	1979-02-23
JPS50100033A (fr)	1975-08-08
GB1472320A (en)	1977-05-04
DE2460938A1 (de)	1975-07-03
DK651174A (fr)	1975-09-01
ATA979874A (de)	1977-10-15

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CA1049006A (fr)	1979-02-20	Derives de d-xylofuranose et une methode pour leur preparation
SU925249A3 (ru)	1982-04-30	Способ получени 0-метилированных производных оксиапорфинов или их солей
US4743704A (en)	1988-05-10	Esters of salsalate with guaiacol, for treating phlogistic bronchopneumopathies
Stanacev et al.	1960	SYNTHESIS OF DIPALMITOYL-l-α-GLYCEROPHOSPHORIC ACID DERIVATIVES, AS POSSIBLE INTERMEDIATES FOR SYNTHESIS OF GLYCERYLPHOSPHATIDES
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US4024275A (en)	1977-05-17	Method of reducing elevated blood pressure with dihydroxy-hexahydrodibenzo(b,d)pyrans
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