SU1075975A3 - Способ получени замещенных ксилита или гексита - Google Patents

Способ получени замещенных ксилита или гексита Download PDF

Info

Publication number: SU1075975A3
Authority: SU; USSR - Soviet Union
Prior art keywords: substituted; dianhydro; reaction mixture; benzene; ether
Prior art date: 1979-08-17

Application number

SU802963500A

Other languages

English (en)

Russian (ru)

Inventor

Видра Илдико

Инштиториш Ласло

Original Assignee

Хиноин Дьедьсер Еш Ведьесети Термекек Дьяра Рт (Инопредприятие)

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.)

1979-08-17

Filing date

1980-08-15

Publication date

1984-02-23

1980-08-15 Application filed by Хиноин Дьедьсер Еш Ведьесети Термекек Дьяра Рт (Инопредприятие) filed Critical Хиноин Дьедьсер Еш Ведьесети Термекек Дьяра Рт (Инопредприятие)

1984-02-23 Application granted granted Critical

1984-02-23 Publication of SU1075975A3 publication Critical patent/SU1075975A3/ru

Links

HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 title claims abstract description 8
235000010447 xylitol Nutrition 0.000 title claims abstract description 8
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 title claims abstract description 8
CBCIHIVRDWLAME-UHFFFAOYSA-N hexanitrodiphenylamine Chemical class [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O CBCIHIVRDWLAME-UHFFFAOYSA-N 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims abstract description 13
239000000811 xylitol Substances 0.000 claims abstract description 10
229960002675 xylitol Drugs 0.000 claims abstract description 10
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims abstract description 7
239000000594 mannitol Substances 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
229930195725 Mannitol Natural products 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
235000010355 mannitol Nutrition 0.000 claims abstract description 3
239000001301 oxygen Substances 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 84
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 35
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
-1 phenylbutyryl Chemical group 0.000 claims description 10
238000000034 method Methods 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
239000002609 medium Substances 0.000 claims description 6
230000011987 methylation Effects 0.000 claims description 5
238000007069 methylation reaction Methods 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 4
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
229910001508 alkali metal halide Inorganic materials 0.000 claims description 3
150000008045 alkali metal halides Chemical class 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 3
FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
239000012312 sodium hydride Substances 0.000 claims description 2
229910000104 sodium hydride Inorganic materials 0.000 claims description 2
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims 1
229910001863 barium hydroxide Inorganic materials 0.000 claims 1
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
230000001085 cytostatic effect Effects 0.000 abstract description 4
239000000600 sorbitol Substances 0.000 abstract description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
125000002252 acyl group Chemical group 0.000 abstract 1
FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 abstract 1
150000002431 hydrogen Chemical class 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
239000011541 reaction mixture Substances 0.000 description 37
239000000243 solution Substances 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
238000003756 stirring Methods 0.000 description 19
239000000203 mixture Substances 0.000 description 16
239000002904 solvent Substances 0.000 description 15
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
238000010790 dilution Methods 0.000 description 9
239000012895 dilution Substances 0.000 description 9
239000006188 syrup Substances 0.000 description 9
235000020357 syrup Nutrition 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000012230 colorless oil Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
229960002920 sorbitol Drugs 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
UGJVZXBXVRMUSG-UHFFFAOYSA-K [B+3].[F-].[F-].[F-] Chemical compound [B+3].[F-].[F-].[F-] UGJVZXBXVRMUSG-UHFFFAOYSA-K 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
238000001816 cooling Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
125000000466 oxiranyl group Chemical group 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
WDFZWSZNOFELJY-OLQVQODUSA-N (1R,6S)-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound C1=CC=C[C@H]2O[C@H]21 WDFZWSZNOFELJY-OLQVQODUSA-N 0.000 description 1
AAFJXZWCNVJTMK-GUCUJZIJSA-N (1s,2r)-1-[(2s)-oxiran-2-yl]-2-[(2r)-oxiran-2-yl]ethane-1,2-diol Chemical compound C([C@@H]1[C@H](O)[C@H](O)[C@H]2OC2)O1 AAFJXZWCNVJTMK-GUCUJZIJSA-N 0.000 description 1
AAFJXZWCNVJTMK-JGWLITMVSA-N (1s,2s)-1-[(2s)-oxiran-2-yl]-2-[(2r)-oxiran-2-yl]ethane-1,2-diol Chemical compound C([C@H]1[C@@H](O)[C@H](O)[C@@H]2OC2)O1 AAFJXZWCNVJTMK-JGWLITMVSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
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 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
150000003944 halohydrins Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
230000010494 opalescence Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Saccharide Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Medicinal Preparation (AREA)
Epoxy Compounds (AREA)

SU802963500A 1979-08-17 1980-08-15 Способ получени замещенных ксилита или гексита SU1075975A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU79VI1266A HU179076B (en)	1979-08-17	1979-08-17	Process for producing terminal bifunctional xilite-methyl-ethers of citostatic activity

Publications (1)

Publication Number	Publication Date
SU1075975A3 true SU1075975A3 (ru)	1984-02-23

Family

ID=11002943

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU802963500A SU1075975A3 (ru)	1979-08-17	1980-08-15	Способ получени замещенных ксилита или гексита

Country Status (18)

Country	Link
JP (1)	JPS5630936A (cs)
AT (1)	AT370416B (cs)
BE (1)	BE884780A (cs)
CA (1)	CA1189525A (cs)
CH (1)	CH648837A5 (cs)
CS (1)	CS214839B2 (cs)
DD (1)	DD153872A5 (cs)
DE (1)	DE3030963A1 (cs)
DK (1)	DK354980A (cs)
FI (1)	FI802551A7 (cs)
FR (1)	FR2463762A1 (cs)
GB (1)	GB2058760B (cs)
HU (1)	HU179076B (cs)
NL (1)	NL8004631A (cs)
NO (1)	NO152412C (cs)
PL (1)	PL130388B1 (cs)
SE (1)	SE8005780L (cs)
SU (1)	SU1075975A3 (cs)

1979
- 1979-08-17 HU HU79VI1266A patent/HU179076B/hu unknown
1980
- 1980-08-13 FI FI802551A patent/FI802551A7/fi not_active Application Discontinuation
- 1980-08-14 BE BE0/201751A patent/BE884780A/fr not_active IP Right Cessation
- 1980-08-14 DD DD223328A patent/DD153872A5/de unknown
- 1980-08-14 AT AT0416180A patent/AT370416B/de not_active IP Right Cessation
- 1980-08-14 FR FR8017974A patent/FR2463762A1/fr active Granted
- 1980-08-15 CS CS805630A patent/CS214839B2/cs unknown
- 1980-08-15 CH CH6179/80A patent/CH648837A5/de not_active IP Right Cessation
- 1980-08-15 DK DK354980A patent/DK354980A/da not_active Application Discontinuation
- 1980-08-15 SE SE8005780A patent/SE8005780L/xx not_active Application Discontinuation
- 1980-08-15 CA CA000358377A patent/CA1189525A/en not_active Expired
- 1980-08-15 NO NO802451A patent/NO152412C/no unknown
- 1980-08-15 NL NL8004631A patent/NL8004631A/nl not_active Application Discontinuation
- 1980-08-15 GB GB8026633A patent/GB2058760B/en not_active Expired
- 1980-08-15 SU SU802963500A patent/SU1075975A3/ru active
- 1980-08-16 DE DE19803030963 patent/DE3030963A1/de not_active Withdrawn
- 1980-08-16 PL PL1980226283A patent/PL130388B1/pl unknown
- 1980-08-18 JP JP11332980A patent/JPS5630936A/ja active Pending

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Title
1. Institoris I. and al. InoesstMgation into the Correlation of Cytostatic Actiorty with the in irtro Diepoxide Formation on Some Tereninally Substituted Hexitols.- Neoplasma, 17, 1, 1970, p. 15-24. 2.Патент СССР по за вке ВНР 2764801/23-04, кл. С 07 D 303/02, 11.05.78. 3. Arznermittel Porschung, 17, 1967, 145-149. 4.Метсщы химии углеводов. Под ред. Н.К.Кочеткова, 1967, с. 29. S.BKuiep К.,Пирсон Д. Органически синтезы. Часть 1, 1973, с. 330-331, 334j, 347, 424. *

Also Published As

Publication number	Publication date
DE3030963A1 (de)	1981-03-19
SE8005780L (sv)	1981-02-18
GB2058760A (en)	1981-04-15
CH648837A5 (de)	1985-04-15
PL226283A1 (cs)	1981-05-22
JPS5630936A (en)	1981-03-28
ATA416180A (de)	1982-08-15
BE884780A (fr)	1980-12-01
AT370416B (de)	1983-03-25
HU179076B (en)	1982-08-28
NL8004631A (nl)	1981-02-19
NO802451L (no)	1981-02-18
DD153872A5 (de)	1982-02-10
FR2463762A1 (fr)	1981-02-27
FR2463762B1 (cs)	1984-10-26
PL130388B1 (en)	1984-08-31
CS214839B2 (en)	1982-06-25
CA1189525A (en)	1985-06-25
NO152412C (no)	1985-09-25
GB2058760B (en)	1983-07-06
FI802551A7 (fi)	1981-01-01
NO152412B (no)	1985-06-17
DK354980A (da)	1981-02-18

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