FI66607C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1,2-5,6-dianhydro-hexitoler - Google Patents

Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1,2-5,6-dianhydro-hexitoler Download PDF

Info

Publication number: FI66607C
Authority: FI; Finland
Prior art keywords: group; dianhydro; alkylcarbonyl; mannitol; free carboxy
Prior art date: 1980-11-04

Application number

FI813430A

Other languages

English (en)

Finnish (fi)

Other versions

FI66607B (fi

FI813430L (fi

Inventor

Ilona Elekes

Laszlo Institoris

Kalman Medzihradszky

Laszlo Oetvoes

Hedvig Medzihradszky-Schweiger

Katalin Di Gleria

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

1981-11-02

Publication date

1984-11-12

1981-05-05 Publication of FI813430L publication Critical patent/FI813430L/fi

1981-11-02 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1984-07-31 Publication of FI66607B publication Critical patent/FI66607B/fi

1984-11-12 Application granted granted Critical

1984-11-12 Publication of FI66607C publication Critical patent/FI66607C/fi

Links

230000001225 therapeutic effect Effects 0.000 title description 7
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 27
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 20
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 16
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 12
239000000594 mannitol Substances 0.000 claims abstract description 12
229930195725 Mannitol Natural products 0.000 claims abstract description 11
235000010355 mannitol Nutrition 0.000 claims abstract description 11
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims abstract description 9
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 9
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000003054 catalyst Substances 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 2
125000003700 epoxy group Chemical group 0.000 claims 1
206010028980 Neoplasm Diseases 0.000 abstract description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
238000005984 hydrogenation reaction Methods 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 abstract description 2
125000004432 carbon atom Chemical group C* 0.000 abstract 7
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
125000004453 alkoxycarbonyl group Chemical group 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
230000002401 inhibitory effect Effects 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 39
239000000203 mixture Substances 0.000 description 32
-1 carboxypropionyl group Chemical group 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
238000007912 intraperitoneal administration Methods 0.000 description 11
239000000047 product Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
238000001914 filtration Methods 0.000 description 8
238000010828 elution Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
206010039491 Sarcoma Diseases 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000004480 active ingredient Substances 0.000 description 5
231100001274 therapeutic index Toxicity 0.000 description 5
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
230000000259 anti-tumor effect 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
238000002513 implantation Methods 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
229940014800 succinic anhydride Drugs 0.000 description 4
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000004593 Epoxy Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
238000001514 detection method Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
239000000126 substance Substances 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
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
208000001382 Experimental Melanoma Diseases 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700157 Rattus norvegicus Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
CDZHZLQKNAKKEC-UHFFFAOYSA-N [bis(hydroxymethylamino)methylamino]methanol Chemical compound OCNC(NCO)NCO CDZHZLQKNAKKEC-UHFFFAOYSA-N 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
150000001342 alkaline earth metals Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
230000001588 bifunctional effect Effects 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
208000032839 leukemia Diseases 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
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
238000005303 weighing Methods 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
101100218590 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) BDF2 gene Proteins 0.000 description 1
241001122767 Theaceae Species 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000004820 blood count Methods 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000007942 carboxylates Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
210000003714 granulocyte Anatomy 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
230000002489 hematologic effect Effects 0.000 description 1
230000011132 hemopoiesis Effects 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
231100000682 maximum tolerated dose Toxicity 0.000 description 1
231100001160 nonlethal Toxicity 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000010355 oscillation Effects 0.000 description 1
150000002924 oxiranes Chemical group 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007858 starting material Substances 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
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
210000000689 upper leg Anatomy 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
230000004580 weight loss Effects 0.000 description 1
239000003357 wound healing promoting agent Substances 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

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

FI813430A 1980-11-04 1981-11-02 Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1,2-5,6-dianhydro-hexitoler FI66607C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU264980		1980-11-04
HU802649A HU182227B (en)	1980-11-04	1980-11-04	Process for preparing hexitols containing free carboxyl group

Publications (3)

Publication Number	Publication Date
FI813430L FI813430L (fi)	1981-05-05
FI66607B FI66607B (fi)	1984-07-31
FI66607C true FI66607C (fi)	1984-11-12

Family

ID=10960444

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI813430A FI66607C (fi)	1980-11-04	1981-11-02	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1,2-5,6-dianhydro-hexitoler

Country Status (15)

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

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
CN107441493A (zh) *	2010-08-18	2017-12-08	德玛医药	制备用于改善未达最佳给药药物治疗的有效性和/或减少其副作用的药物的方法
EP3273951B1 (en)	2015-03-27	2020-07-29	Symbionyx Pharmaceuticals Inc.	Compositions and methods for treating 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/en not_active Expired
- 1981-11-02 JP JP56174703A patent/JPH0699364B2/ja not_active Expired - Lifetime
- 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
- 1981-11-03 CS CS818075A patent/CS251066B2/cs unknown
- 1981-11-03 DK DK485881A patent/DK485881A/da not_active Application Discontinuation
- 1981-11-03 CA CA000389270A patent/CA1192210A/en not_active Expired
- 1981-11-03 DD DD81234590A patent/DD202431A5/de not_active IP Right Cessation
- 1981-11-03 SU SU813350453A patent/SU1205769A3/ru active
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
SU1225487A3 (ru)	1986-04-15
IL64088A0 (en)	1982-01-31
ATE21394T1 (de)	1986-08-15
SU1205769A3 (ru)	1986-01-15
EP0051467A1 (en)	1982-05-12
FI66607B (fi)	1984-07-31
DK485881A (da)	1982-05-05
JPS57106642A (en)	1982-07-02
FI813430L (fi)	1981-05-05
CA1192210A (en)	1985-08-20
DD207374A5 (de)	1984-02-29
GR77292B (cs)	1984-09-11
CS251066B2 (en)	1987-06-11
JPH0699364B2 (ja)	1994-12-07
SU1194863A1 (ru)	1985-11-30
YU259081A (en)	1983-12-31
US4419522A (en)	1983-12-06
HU182227B (en)	1983-12-28
DE3175121D1 (en)	1986-09-18
DD202431A5 (de)	1983-09-14
EP0051467B1 (en)	1986-08-13

Legal Events

Date	Code	Title	Description
1995-06-09	MM	Patent lapsed
2004-08-31	MM	Patent lapsed	Owner name: CHINOIN GYOGUSZER ES VEGYESZETI TERMEKEK

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