HU176216B - Process for producing terminally bifuntional xylite derivatives of citostatic activity - Google Patents

Process for producing terminally bifuntional xylite derivatives of citostatic activity Download PDF

Info

Publication number: HU176216B
Authority: HU; Hungary
Prior art keywords: preparation; formula; phenyl; dianhydroxyl; benzoyl
Prior art date: 1978-05-11

Application number

HU78CI1826A

Other languages

English (en)

Hungarian (hu)

Inventor

Laszlone Vidra

Laszlo Institoris

Sandor Eckhardt

Karoly Lapis

Andras Jeney

Laszlo Kopper

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1978-05-11

Filing date

1978-05-11

Publication date

1981-01-28

1978-05-11 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1978-05-11 Priority to HU78CI1826A priority Critical patent/HU176216B/hu

1979-04-30 Priority to DE19792917538 priority patent/DE2917538A1/de

1979-04-30 Priority to IL57182A priority patent/IL57182A/xx

1979-05-02 Priority to IN447/CAL/79A priority patent/IN150040B/en

1979-05-06 Priority to EG264/79A priority patent/EG15150A/xx

1979-05-07 Priority to GR59037A priority patent/GR68495B/el

1979-05-09 Priority to FI791484A priority patent/FI67845C/fi

1979-05-09 Priority to YU01080/79A priority patent/YU108079A/xx

1979-05-09 Priority to SE7904080A priority patent/SE7904080L/xx

1979-05-09 Priority to FR7911733A priority patent/FR2425445A1/fr

1979-05-09 Priority to NL7903634A priority patent/NL7903634A/xx

1979-05-10 Priority to CS793205A priority patent/CS211399B2/cs

1979-05-10 Priority to CH438979A priority patent/CH641437A5/de

1979-05-10 Priority to BE0/195089A priority patent/BE876166A/xx

1979-05-10 Priority to CA000327317A priority patent/CA1145349A/en

1979-05-10 Priority to GB7916274A priority patent/GB2024204B/en

1979-05-10 Priority to JP5758879A priority patent/JPS5522662A/ja

1979-05-10 Priority to AT347779A priority patent/AT361945B/de

1979-05-10 Priority to IT67984/79A priority patent/IT1118485B/it

1979-05-10 Priority to AR276464A priority patent/AR222332A1/es

1979-05-10 Priority to DK195279A priority patent/DK195279A/da

1979-05-10 Priority to PL1979215489A priority patent/PL121560B1/pl

1979-05-10 Priority to NO791564A priority patent/NO153928C/no

1979-05-11 Priority to DD79212780A priority patent/DD143765A5/de

1979-05-11 Priority to ES480869A priority patent/ES480869A1/es

1979-05-11 Priority to SU792764801A priority patent/SU984410A3/ru

1981-01-28 Publication of HU176216B publication Critical patent/HU176216B/hu

Links

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 6
238000000034 method Methods 0.000 title claims description 22
230000000694 effects Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
230000001085 cytostatic effect Effects 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
150000002431 hydrogen Chemical class 0.000 claims abstract 3
239000001301 oxygen Substances 0.000 claims abstract 2
229910052760 oxygen Inorganic materials 0.000 claims abstract 2
-1 benzoyl phenyl group Chemical group 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
238000005917 acylation reaction Methods 0.000 claims description 6
230000010933 acylation Effects 0.000 claims description 5
239000000824 cytostatic agent Substances 0.000 claims description 5
238000009472 formulation Methods 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
239000002516 radical scavenger Substances 0.000 claims description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
VQDQISMDUHBUFF-UHFFFAOYSA-N 4-phenylbutanoyl chloride Chemical compound ClC(=O)CCCC1=CC=CC=C1 VQDQISMDUHBUFF-UHFFFAOYSA-N 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
239000012346 acetyl chloride Substances 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
239000003085 diluting agent Substances 0.000 claims description 2
239000000945 filler Substances 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
150000003973 alkyl amines Chemical class 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
239000000811 xylitol Substances 0.000 abstract description 4
229960002675 xylitol Drugs 0.000 abstract description 4
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 abstract description 3
125000001589 carboacyl group Chemical group 0.000 abstract description 3
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 abstract description 3
235000010447 xylitol Nutrition 0.000 abstract description 3
125000003435 aroyl group Chemical group 0.000 abstract 1
125000005905 mesyloxy group Chemical group 0.000 abstract 1
238000010561 standard procedure Methods 0.000 abstract 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
241001465754 Metazoa Species 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
239000004480 active ingredient Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
206010028980 Neoplasm Diseases 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
238000002054 transplantation Methods 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 5
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000843 powder Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
230000004083 survival effect Effects 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
235000002639 sodium chloride Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
FZQZRBQKXXGAMZ-UHFFFAOYSA-N 2-benzyl-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1CC1=CC=CC=C1 FZQZRBQKXXGAMZ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
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
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
239000013543 active substance Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000003708 ampul Substances 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000001802 infusion Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
150000005846 sugar alcohols Chemical group 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010003445 Ascites Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
KIHFFINCXFGABP-UHFFFAOYSA-N Cl.[I] Chemical compound Cl.[I] KIHFFINCXFGABP-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
239000004097 EU approved flavor enhancer Substances 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
125000004036 acetal group Chemical group 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical group 0.000 description 1
229960004977 anhydrous lactose Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
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 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000002000 scavenging effect Effects 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
231100000041 toxicology testing Toxicity 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
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
- 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
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/64—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/42—Polyhydroxylic acyclic alcohols
- 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
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals

Landscapes

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

HU78CI1826A 1978-05-11 1978-05-11 Process for producing terminally bifuntional xylite derivatives of citostatic activity HU176216B (en)

Priority Applications (26)

Application Number	Priority Date	Filing Date	Title
HU78CI1826A HU176216B (en)	1978-05-11	1978-05-11	Process for producing terminally bifuntional xylite derivatives of citostatic activity
DE19792917538 DE2917538A1 (de)	1978-05-11	1979-04-30	Terminal-bifunktionelle xylit-derivate
IL57182A IL57182A (en)	1978-05-11	1979-04-30	Xylite derivatives,their preparation and cytostatic pharmaceutical compositions containing them
IN447/CAL/79A IN150040B (de)	1978-05-11	1979-05-02
EG264/79A EG15150A (en)	1978-05-11	1979-05-06	Process for preparing of xylite derivatives as cell growing stimulants
GR59037A GR68495B (de)	1978-05-11	1979-05-07
FI791484A FI67845C (fi)	1978-05-11	1979-05-09	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara xylitolderivat
YU01080/79A YU108079A (en)	1978-05-11	1979-05-09	Process for producing terminal bifunctional xylitol derivatives
SE7904080A SE7904080L (sv)	1978-05-11	1979-05-09	Terminal-bifunktionella xylitderivat
FR7911733A FR2425445A1 (fr)	1978-05-11	1979-05-09	Derives de xylite bifonctionnels terminaux utiles comme medicaments
NL7903634A NL7903634A (nl)	1978-05-11	1979-05-09	Eindstandig-bifunctionale xyliet-derivaten.
CS793205A CS211399B2 (en)	1978-05-11	1979-05-10	Method of making the the new xylite derivatives
CH438979A CH641437A5 (de)	1978-05-11	1979-05-10	Cytostatisch-wirkende xylit-derivate.
BE0/195089A BE876166A (fr)	1978-05-11	1979-05-10	Derives de xylite bifonctionnels terminaux utiles comme medicaments
CA000327317A CA1145349A (en)	1978-05-11	1979-05-10	Terminal bifunktional xylite-derivatives
GB7916274A GB2024204B (en)	1978-05-11	1979-05-10	Cylitol derivatives their preparation and pharmaceutical compositions containing them
JP5758879A JPS5522662A (en)	1978-05-11	1979-05-10	Enddgroup bifunctional xylite derivative
AT347779A AT361945B (de)	1978-05-11	1979-05-10	Verfahren zur herstellung von neuen xylit- -derivaten
IT67984/79A IT1118485B (it)	1978-05-11	1979-05-10	Derivati della xillite bifunzionali terminali
AR276464A AR222332A1 (es)	1978-05-11	1979-05-10	Procedimiento para la produccion de derivados de la xilita
DK195279A DK195279A (da)	1978-05-11	1979-05-10	Fremgangsmaade til fremstilling af xylitolderivater
PL1979215489A PL121560B1 (en)	1978-05-11	1979-05-10	Process for preparing novel derivatives of xylitol
NO791564A NO153928C (no)	1978-05-11	1979-05-10	Analogifremgangsmaate ved fremstilling av xylit-derivater.
DD79212780A DD143765A5 (de)	1978-05-11	1979-05-11	Verfahren zur herstellung von neuen xylit-derivaten
ES480869A ES480869A1 (es)	1978-05-11	1979-05-11	Procedimiento de preparar derivados de xilita.
SU792764801A SU984410A3 (ru)	1978-05-11	1979-05-11	Способ получени производных 1,2-4,5-диангидроксилита

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU78CI1826A HU176216B (en)	1978-05-11	1978-05-11	Process for producing terminally bifuntional xylite derivatives of citostatic activity

Publications (1)

Publication Number	Publication Date
HU176216B true HU176216B (en)	1981-01-28

Family

ID=10994695

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU78CI1826A HU176216B (en)	1978-05-11	1978-05-11	Process for producing terminally bifuntional xylite derivatives of citostatic activity

Country Status (26)

Country	Link
JP (1)	JPS5522662A (de)
AR (1)	AR222332A1 (de)
AT (1)	AT361945B (de)
BE (1)	BE876166A (de)
CA (1)	CA1145349A (de)
CH (1)	CH641437A5 (de)
CS (1)	CS211399B2 (de)
DD (1)	DD143765A5 (de)
DE (1)	DE2917538A1 (de)
DK (1)	DK195279A (de)
EG (1)	EG15150A (de)
ES (1)	ES480869A1 (de)
FI (1)	FI67845C (de)
FR (1)	FR2425445A1 (de)
GB (1)	GB2024204B (de)
GR (1)	GR68495B (de)
HU (1)	HU176216B (de)
IL (1)	IL57182A (de)
IN (1)	IN150040B (de)
IT (1)	IT1118485B (de)
NL (1)	NL7903634A (de)
NO (1)	NO153928C (de)
PL (1)	PL121560B1 (de)
SE (1)	SE7904080L (de)
SU (1)	SU984410A3 (de)
YU (1)	YU108079A (de)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH381666A (de) *	1958-04-24	1964-09-15	Nat Res Dev	Verfahren zur Herstellung von Derivaten von polyhydrischen Alkoholen
DE1668241A1 (de) *	1968-03-06	1971-02-11	Herbrand Kg Dr	Therapeutisch wirksame 1,5-di-substituierte Derivate von Xylit,Adonit und Arabit

1978
- 1978-05-11 HU HU78CI1826A patent/HU176216B/hu unknown
1979
- 1979-04-30 DE DE19792917538 patent/DE2917538A1/de not_active Withdrawn
- 1979-04-30 IL IL57182A patent/IL57182A/xx unknown
- 1979-05-02 IN IN447/CAL/79A patent/IN150040B/en unknown
- 1979-05-06 EG EG264/79A patent/EG15150A/xx active
- 1979-05-07 GR GR59037A patent/GR68495B/el unknown
- 1979-05-09 FI FI791484A patent/FI67845C/fi not_active IP Right Cessation
- 1979-05-09 NL NL7903634A patent/NL7903634A/xx not_active Application Discontinuation
- 1979-05-09 SE SE7904080A patent/SE7904080L/xx not_active Application Discontinuation
- 1979-05-09 YU YU01080/79A patent/YU108079A/xx unknown
- 1979-05-09 FR FR7911733A patent/FR2425445A1/fr active Granted
- 1979-05-10 CS CS793205A patent/CS211399B2/cs unknown
- 1979-05-10 AR AR276464A patent/AR222332A1/es active
- 1979-05-10 IT IT67984/79A patent/IT1118485B/it active
- 1979-05-10 AT AT347779A patent/AT361945B/de not_active IP Right Cessation
- 1979-05-10 BE BE0/195089A patent/BE876166A/xx not_active IP Right Cessation
- 1979-05-10 CA CA000327317A patent/CA1145349A/en not_active Expired
- 1979-05-10 PL PL1979215489A patent/PL121560B1/pl unknown
- 1979-05-10 DK DK195279A patent/DK195279A/da not_active Application Discontinuation
- 1979-05-10 CH CH438979A patent/CH641437A5/de not_active IP Right Cessation
- 1979-05-10 JP JP5758879A patent/JPS5522662A/ja active Pending
- 1979-05-10 GB GB7916274A patent/GB2024204B/en not_active Expired
- 1979-05-10 NO NO791564A patent/NO153928C/no unknown
- 1979-05-11 ES ES480869A patent/ES480869A1/es not_active Expired
- 1979-05-11 DD DD79212780A patent/DD143765A5/de unknown
- 1979-05-11 SU SU792764801A patent/SU984410A3/ru active

Also Published As

Publication number	Publication date
NO153928C (no)	1986-06-18
GB2024204B (en)	1982-10-27
BE876166A (fr)	1979-09-03
FI791484A7 (fi)	1979-11-12
IL57182A0 (en)	1979-07-25
PL215489A1 (de)	1980-02-11
NO153928B (no)	1986-03-10
ATA347779A (de)	1980-09-15
IN150040B (de)	1982-07-03
IL57182A (en)	1983-07-31
CS211399B2 (en)	1982-02-26
FR2425445B1 (de)	1984-06-08
EG15150A (en)	1985-12-31
ES480869A1 (es)	1980-06-16
YU108079A (en)	1982-10-31
PL121560B1 (en)	1982-05-31
AT361945B (de)	1981-04-10
DD143765A5 (de)	1980-09-10
NL7903634A (nl)	1979-11-13
DK195279A (da)	1979-11-12
IT7967984A0 (it)	1979-05-10
JPS5522662A (en)	1980-02-18
FI67845B (fi)	1985-02-28
NO791564L (no)	1979-11-13
CA1145349A (en)	1983-04-26
AR222332A1 (es)	1981-05-15
SU984410A3 (ru)	1982-12-23
FR2425445A1 (fr)	1979-12-07
FI67845C (fi)	1985-06-10
GR68495B (de)	1982-01-07
CH641437A5 (de)	1984-02-29
DE2917538A1 (de)	1979-11-15
IT1118485B (it)	1986-03-03
SE7904080L (sv)	1979-11-12
GB2024204A (en)	1980-01-09

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US4423044A (en)	1983-12-27	3,4-Dihydro-5H-2,3-benzodiazepine derivatives and pharmaceutical use thereof
IL110820A (en)	1995-11-27	History of imidazoline - 5 - on and 5, 6 - dihydropyrimidine - 4 - on preparation
FR2554719A1 (fr)	1985-05-17	Medicaments a base de nouveaux derives de la vinyl-6 furo-(3,4-c)-pyridine
HU202550B (en)	1991-03-28	Process for producing 2-substituted adenosyl derivatives and pharmaceutical compositions comprising such compounds
JPS6023102B2 (ja)	1985-06-05	新規エピニンエステル、その製法及び医薬組成物
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NL193541C (nl)	2000-01-04	8 Alfa-acylaminoergolinen, werkwijzen voor de bereiding daarvan en preparaten die ze bevatten.
JPH0261476B2 (de)	1990-12-20
SU1240363A3 (ru)	1986-06-23	Способ получени ( @ )-5-(2-бромвинил)уридина
BE1003698A3 (fr)	1992-05-26	Derives sulfonyles de la thieno-triazolo-diazepine, un procede pour leur preparation et des compositions therapeutiques en contenant.
HU176216B (en)	1981-01-28	Process for producing terminally bifuntional xylite derivatives of citostatic activity
CH628014A5 (en)	1982-02-15	Gamma-aryl-gamma-oxoisovaleric acids having antiphlogistic and antalgic properties
IT8347666A1 (it)	1984-08-03	"Derivati del benzotiofene, loro preparazione e loro impiego come medicamenti".
JPH03501389A (ja)	1991-03-28	新規チエニルオキシ‐アルキルアミン誘導体、その製法及びこの化合物を含有する医薬
EP0240986B1 (de)	1991-01-23	D-Nor-7-ergolinderivate, Verfahren zu ihrer Herstellung, pharmazeutische Zubereitung und Verwendung
HU187650B (en)	1986-02-28	Process for preparing of new 12-substituated carbamide derivatives of ergolins
HU184767B (en)	1984-10-29	Process for the production of prostacycline-analogues and of pharmaceutical preparations containing them as active substance
IL28867A (en)	1972-04-27	1-adamantyl and 1-adamantylmethyl carbonates of testosterone and derivatives thereof
CA1070616A (en)	1980-01-29	Anti-tumor composition
CS221844B2 (en)	1983-04-29	Method of making the 5-substituted dialuric acids
US3855229A (en)	1974-12-17	Benzopyran-5-ols
US3635962A (en)	1972-01-18	4 - bis-morpholino- and 2
US4661297A (en)	1987-04-28	Basic ethers of 7-oxo-7H-benzo(c) fluorene and a process for their production
HU187733B (en)	1986-02-28	Process for preparing apovincaminic acid derivatives
JP2860385B2 (ja)	1999-02-24	ビスべンジルイソキノリン誘導体