CS251066B2 - Method of new therapeutically applicable 1,2-5,6-dianhydrohexitols production - Google Patents

Method of new therapeutically applicable 1,2-5,6-dianhydrohexitols production Download PDF

Info

Publication number: CS251066B2
Authority: CS; Czechoslovakia
Prior art keywords: group; carbon atoms; dulcitol; unsaturated; free carboxy
Prior art date: 1980-11-04

Application number

CS818075A

Other languages

Czech (cs)

English (en)

Inventor

Ilona Elekes

Laszlo Institoris

Kalman Medzihradszky

Laszlo Oetvoes

Hedvig Medzihradszky

Gleria Katalin Di

Janos Sugar

Zsuzsanna Somfai-Relle

Sandor Eckhardt

Ivan Hidy

Sandor Kerpel-Fronius

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.)

1980-11-04

Filing date

1981-11-03

Publication date

1987-06-11

1981-11-03 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1985-08-16 Priority to CS855962A priority Critical patent/CS251099B2/cs

1987-06-11 Publication of CS251066B2 publication Critical patent/CS251066B2/cs

Links

238000000034 method Methods 0.000 title claims description 26
238000004519 manufacturing process Methods 0.000 title description 3
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 claims abstract description 31
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 17
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 11
239000000594 mannitol Substances 0.000 claims abstract description 11
229930195725 Mannitol Natural products 0.000 claims abstract description 10
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 10
235000010355 mannitol Nutrition 0.000 claims abstract description 10
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims abstract description 7
FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical group OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 claims abstract description 5
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 22
-1 β-benzyloxycarbonylpropionyl group Chemical group 0.000 claims description 22
239000003054 catalyst Substances 0.000 claims description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
229910052763 palladium Inorganic materials 0.000 claims description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 13
206010028980 Neoplasm Diseases 0.000 abstract description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 abstract description 2
230000002401 inhibitory effect Effects 0.000 abstract description 2
229920006395 saturated elastomer Polymers 0.000 abstract 6
125000005129 aryl carbonyl group Chemical group 0.000 abstract 2
FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 abstract 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
230000026030 halogenation Effects 0.000 abstract 1
238000005658 halogenation reaction Methods 0.000 abstract 1
125000004430 oxygen atom Chemical group O* 0.000 abstract 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 13
239000004480 active ingredient Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
239000000047 product Substances 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
238000002054 transplantation Methods 0.000 description 6
241000699670 Mus sp. Species 0.000 description 5
239000002775 capsule Substances 0.000 description 5
238000007912 intraperitoneal administration Methods 0.000 description 5
238000001990 intravenous administration Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
206010039491 Sarcoma Diseases 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
206010003445 Ascites Diseases 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
241000700157 Rattus norvegicus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
231100001274 therapeutic index Toxicity 0.000 description 3
KPICIOOAGPZSKI-UHFFFAOYSA-N 2-benzyl-4-nitropyridine Chemical compound [O-][N+](=O)C1=CC=NC(CC=2C=CC=CC=2)=C1 KPICIOOAGPZSKI-UHFFFAOYSA-N 0.000 description 2
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 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000003708 ampul Substances 0.000 description 2
238000004820 blood count Methods 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
210000000936 intestine Anatomy 0.000 description 2
208000032839 leukemia Diseases 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
238000012544 monitoring process Methods 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
230000001875 tumorinhibitory effect Effects 0.000 description 2
238000005303 weighing Methods 0.000 description 2
AAFJXZWCNVJTMK-GUCUJZIJSA-N (1s,2r)-1-[(2s)-oxiran-2-yl]-2-[(2r)-oxiran-2-yl]ethane-1,2-diol Chemical class C([C@@H]1[C@H](O)[C@H](O)[C@H]2OC2)O1 AAFJXZWCNVJTMK-GUCUJZIJSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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 description 1
239000004593 Epoxy Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
208000001382 Experimental Melanoma Diseases 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
206010022998 Irritability Diseases 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
206010039580 Scar Diseases 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
150000007942 carboxylates Chemical group 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000001085 cytostatic effect Effects 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
210000003714 granulocyte Anatomy 0.000 description 1
239000013003 healing agent Substances 0.000 description 1
230000002489 hematologic effect Effects 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000002372 labelling Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000008176 lyophilized powder Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
231100000682 maximum tolerated dose Toxicity 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
231100001160 nonlethal Toxicity 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
210000000689 upper leg Anatomy 0.000 description 1
238000012800 visualization Methods 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Hematology (AREA)
Oncology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Epoxy Compounds (AREA)
Compounds Of Unknown Constitution (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Peptides Or Proteins (AREA)
Separation By Low-Temperature Treatments (AREA)

CS818075A 1980-11-04 1981-11-03 Method of new therapeutically applicable 1,2-5,6-dianhydrohexitols production CS251066B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS855962A CS251099B2 (cs)	1980-11-04	1985-08-16	Způsob výroby nových terapeuticky použitelných 1,2-5,6-dianhydrohexitolů

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU802649A HU182227B (en)	1980-11-04	1980-11-04	Process for preparing hexitols containing free carboxyl group

Publications (1)

Publication Number	Publication Date
CS251066B2 true CS251066B2 (en)	1987-06-11

Family

ID=10960444

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS818075A CS251066B2 (en)	1980-11-04	1981-11-03	Method of new therapeutically applicable 1,2-5,6-dianhydrohexitols production

Country Status (15)

Country	Link
US (1)	US4419522A (de)
EP (1)	EP0051467B1 (de)
JP (1)	JPH0699364B2 (de)
AT (1)	ATE21394T1 (de)
CA (1)	CA1192210A (de)
CS (1)	CS251066B2 (de)
DD (2)	DD202431A5 (de)
DE (1)	DE3175121D1 (de)
DK (1)	DK485881A (de)
FI (1)	FI66607C (de)
GR (1)	GR77292B (de)
HU (1)	HU182227B (de)
IL (1)	IL64088A0 (de)
SU (3)	SU1205769A3 (de)
YU (1)	YU259081A (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU195754B (en) *	1984-01-18	1988-07-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing 1,2-5,6-dianhydro-3,4-diacyl-dulcitol
JP3046095B2 (ja) *	1991-05-23	2000-05-29	株式会社日立製作所	並列抵抗付遮断器
US8496917B2 (en) *	2009-11-13	2013-07-30	Sytheon Ltd	Compositions and methods for improving skin appearance
AU2011292044A1 (en) *	2010-08-18	2013-04-04	Del Mar Pharmaceuticals	Compositions and methods to improve the therapeutic benefit of suboptimally administered chemical compounds including substituted hexitols such as dianhydrogalactitol and diacetyldianhydrogalactitol
DK3273951T3 (da)	2015-03-27	2020-11-02	Symbionyx Pharmaceuticals Inc	Sammensætninger og fremgangsmåder til behandling af psoriasis

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU172826B (hu) *	1974-12-24	1978-12-28	Mta Koezponti Kemiai Kutato In	Sposob poluchenija novykh acilnykh proizvodnykh 1,2-5,6-diangidro-geksitov s protivoopukholevoj aktivnost'ju

1980
- 1980-11-04 HU HU802649A patent/HU182227B/hu not_active IP Right Cessation
1981
- 1981-10-21 IL IL64088A patent/IL64088A0/xx not_active IP Right Cessation
- 1981-10-26 US US06/315,182 patent/US4419522A/en not_active Expired - Fee Related
- 1981-10-30 AT AT81305161T patent/ATE21394T1/de not_active IP Right Cessation
- 1981-10-30 DE DE8181305161T patent/DE3175121D1/de not_active Expired
- 1981-10-30 EP EP81305161A patent/EP0051467B1/de not_active Expired
- 1981-11-02 FI FI813430A patent/FI66607C/fi not_active IP Right Cessation
- 1981-11-02 YU YU02590/81A patent/YU259081A/xx unknown
- 1981-11-02 GR GR66405A patent/GR77292B/el unknown
- 1981-11-02 JP JP56174703A patent/JPH0699364B2/ja not_active Expired - Lifetime
- 1981-11-03 DD DD81234590A patent/DD202431A5/de not_active IP Right Cessation
- 1981-11-03 DK DK485881A patent/DK485881A/da not_active Application Discontinuation
- 1981-11-03 CS CS818075A patent/CS251066B2/cs unknown
- 1981-11-03 SU SU813350453A patent/SU1205769A3/ru active
- 1981-11-03 CA CA000389270A patent/CA1192210A/en not_active Expired
1982
- 1982-05-18 SU SU823437177A patent/SU1194863A1/ru active
- 1982-05-18 SU SU823437277A patent/SU1225487A3/ru active
1983
- 1983-11-03 DD DD83247073A patent/DD207374A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
IL64088A0 (en)	1982-01-31
FI66607C (fi)	1984-11-12
DK485881A (da)	1982-05-05
EP0051467A1 (de)	1982-05-12
DE3175121D1 (en)	1986-09-18
HU182227B (en)	1983-12-28
CA1192210A (en)	1985-08-20
JPS57106642A (en)	1982-07-02
SU1225487A3 (ru)	1986-04-15
FI813430L (fi)	1981-05-05
ATE21394T1 (de)	1986-08-15
US4419522A (en)	1983-12-06
EP0051467B1 (de)	1986-08-13
SU1194863A1 (ru)	1985-11-30
SU1205769A3 (ru)	1986-01-15
JPH0699364B2 (ja)	1994-12-07
YU259081A (en)	1983-12-31
DD202431A5 (de)	1983-09-14
FI66607B (fi)	1984-07-31
DD207374A5 (de)	1984-02-29
GR77292B (de)	1984-09-11

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JPS6259715B2 (de)	1987-12-12
EP0008746A1 (de)	1980-03-19	Alpha-(N-arylsulfonyl)-4-argininsäureamide, Verfahren zu ihrer Herstellung und diese Substanzen enthaltende pharmazeutische Zusammensetzungen
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CS251066B2 (en)	1987-06-11	Method of new therapeutically applicable 1,2-5,6-dianhydrohexitols production
ES2225214T3 (es)	2005-03-16	Nuevos compuestos de xantona, su preparacion y uso como medicamento.
WO1998000422A1 (en)	1998-01-08	Oxirane carboxylic acid derivative and its manufacturing method
CA2151635A1 (en)	1995-12-15	Antitumoral Compounds
FR2505834A1 (fr)	1982-11-19	Derives de la thiazolidine
JPS627200B2 (de)	1987-02-16
CZ282997B6 (cs)	1997-12-17	N-//4,5-dihydroxy- a 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracenyl/karbonyl/aminokyseliny, způsob výroby a farmaceutický prostředek s jejich obsahem
JPH01113391A (ja)	1989-05-02	マイトマイシン誘導体
EP0215687B1 (de)	1990-05-23	Biologisch aktive Substanz, Girolline genannt, extrahiert aus dem Schwamm Pseudaxinyssa cantharella, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
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NO144632B (no)	1981-06-29	Analogifremgangsmaate ved fremstilling av nye terapeutisk aktive dianhydroheksitid-acyl-derivater
US20020198382A1 (en)	2002-12-26	Oxiran carboxylic acids for the treatment of diabetes
US2753340A (en)	1956-07-03	Maleate salts of protoveratrine a and protoveratrine b
US3904681A (en)	1975-09-09	Propionic acid
CS251099B2 (cs)	1987-06-11	Způsob výroby nových terapeuticky použitelných 1,2-5,6-dianhydrohexitolů
US4117133A (en)	1978-09-26	Vasodilating cuanzine hydrazides
KR810000494B1 (ko)	1981-05-20	빈카 알카로이드의 옥사졸리딘 디온 유도체의 제조방법
CH638814A5 (fr)	1983-10-14	4-desacetoxy-4alpha-hydroxyindole-dihydroindols et leur preparation.
JPH03503900A (ja)	1991-08-29	複素環式スルホニルニトロメタン、その製造法および医薬製剤
JP2860385B2 (ja)	1999-02-24	ビスべンジルイソキノリン誘導体
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