DD202431A5 - Verfahren zur herstellung von neuen freie carboxygruppen enthaltenden hexiten - Google Patents

Verfahren zur herstellung von neuen freie carboxygruppen enthaltenden hexiten Download PDF

Info

Publication number: DD202431A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; saturated; unsaturated; group; free carboxy
Prior art date: 1980-11-04

Application number

DD81234590A

Other languages

German (de)

English (en)

Inventor

Ilona Elekes

Laszlo Institoris

Kalman Medzihradszky

Laszlo Oetvoes

Hedvig Medzihradszky

Gleria Katalin Di

Janos Sugar

Zsuzsanna Somfai-Relle

Sandor Eckhardt

Ivan Hindy

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

1983-09-14

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

1983-09-14 Publication of DD202431A5 publication Critical patent/DD202431A5/de

Links

125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title claims abstract description 24
238000002360 preparation method Methods 0.000 title claims description 16
238000000034 method Methods 0.000 title claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 30
229920006395 saturated elastomer Polymers 0.000 claims abstract description 30
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 18
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 13
150000003839 salts Chemical class 0.000 claims abstract description 13
229930195725 Mannitol Natural products 0.000 claims abstract description 11
235000010355 mannitol Nutrition 0.000 claims abstract description 11
239000000594 mannitol Substances 0.000 claims abstract description 11
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 claims abstract description 8
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 8
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims abstract description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 6
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 6
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 28
239000003054 catalyst Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 6
229910052763 palladium Inorganic materials 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
238000009938 salting Methods 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 4
230000002401 inhibitory effect Effects 0.000 abstract description 3
125000005129 aryl carbonyl group Chemical group 0.000 abstract 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
125000004435 hydrogen atom Chemical group [H]* 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
-1 carboxybutyryl Chemical group 0.000 description 50
239000000203 mixture Substances 0.000 description 31
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
239000000243 solution Substances 0.000 description 9
230000001225 therapeutic effect Effects 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
229940079593 drug Drugs 0.000 description 7
239000003814 drug Substances 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
238000007912 intraperitoneal administration Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
206010039491 Sarcoma Diseases 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241000700157 Rattus norvegicus Species 0.000 description 4
229960004217 benzyl alcohol Drugs 0.000 description 4
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
229940014800 succinic anhydride Drugs 0.000 description 4
238000002054 transplantation Methods 0.000 description 4
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 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
239000004593 Epoxy Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000011161 development Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000001588 bifunctional effect Effects 0.000 description 2
238000004820 blood count Methods 0.000 description 2
210000000988 bone and bone Anatomy 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000155 melt Substances 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
239000012071 phase Substances 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000011343 solid material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
210000001519 tissue Anatomy 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
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
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
201000000274 Carcinosarcoma 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
241000282326 Felis catus Species 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
241001465754 Metazoa Species 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
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
150000001412 amines Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 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
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000001085 cytostatic effect Effects 0.000 description 1
125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
ULWBKOMBLVWAHO-UHFFFAOYSA-N ethanol;2-phenylethanol Chemical compound CCO.OCCC1=CC=CC=C1 ULWBKOMBLVWAHO-UHFFFAOYSA-N 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
YUPQOCKHBKYZMN-UHFFFAOYSA-N ethylaminomethanetriol Chemical compound CCNC(O)(O)O YUPQOCKHBKYZMN-UHFFFAOYSA-N 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
125000001165 hydrophobic group Chemical group 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000002656 inhibitory effect on ulcer Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000002372 labelling Methods 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 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
150000002924 oxiranes Chemical group 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000001875 tumorinhibitory effect Effects 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
210000000689 upper leg Anatomy 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)

DD81234590A 1980-11-04 1981-11-03 Verfahren zur herstellung von neuen freie carboxygruppen enthaltenden hexiten DD202431A5 (de)

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
DD202431A5 true DD202431A5 (de)	1983-09-14

Family

ID=10960444

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD81234590A DD202431A5 (de)	1980-11-04	1981-11-03	Verfahren zur herstellung von neuen freie carboxygruppen enthaltenden hexiten
DD83247073A DD207374A5 (de)	1980-11-04	1983-11-03	Verfahren zur herstellung neuer freie carboxygruppen enthaltender hexite

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD83247073A DD207374A5 (de)	1980-11-04	1983-11-03	Verfahren zur herstellung neuer freie carboxygruppen enthaltender hexite

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
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/en 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 (en)	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
CS251066B2 (en)	1987-06-11
EP0051467B1 (en)	1986-08-13
SU1194863A1 (ru)	1985-11-30
SU1205769A3 (ru)	1986-01-15
JPH0699364B2 (ja)	1994-12-07
YU259081A (en)	1983-12-31
FI66607B (fi)	1984-07-31
DD207374A5 (de)	1984-02-29
GR77292B (cs)	1984-09-11

Legal Events

Date	Code	Title	Description
1995-08-31	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE3116066C2 (de)	1993-10-21	Hydronaphthalinderivate, deren Epoxide und diese Verbindungen enthaltende Arzneimittel
DE3026172C2 (cs)	1991-05-08
DE2726619C2 (cs)	1989-08-10
DE1912352C3 (de)	1975-11-27	Pyridin-N-oxyd-Derivale und Verfahren zu ihrer Herstellung
DE2228012B2 (de)	1979-05-23	-Aminophenylacetamido] -penicülansäure und Verfahren zu seiner Herstellung
DE2426304C2 (cs)	1988-03-17
DE2356655C3 (de)	1981-12-17	Substituierte Phenoxy-α-methylpropionsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE69521525T2 (de)	2002-04-25	Lignane, verfahren zu ihrer herstellung, ihre pharmazeutische compositionen und anwendungen
DE2425983B2 (de)	1978-01-19	Sulfonsaeuresalze von acylcholinen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzung
CH630378A5 (de)	1982-06-15	Verfahren zur herstellung neuer kondensierter pyrimidin-derivate.
DE1793841B1 (de)	1980-01-03	trans-4-Aminomethylcyclohexan-1-carbonsaeure und Verfahren zur Herstellung
DD202431A5 (de)	1983-09-14	Verfahren zur herstellung von neuen freie carboxygruppen enthaltenden hexiten
EP0400499B1 (de)	1994-04-06	Neue Acylaminosäurederivate enthaltende Arzneimittel und Diätetika
DE2632118C3 (de)	1979-12-13	Apovincaminolester und Verfahren zu deren Herstellung und Arzneimittel
DE1958514C3 (de)	1973-10-25	Apovincaminsaureamid
DE3013502C2 (de)	1985-02-07	[2''-(Trifluormethyl)-phenthiazin-10''-yl-(n-prop-3'''ylpiperazin-4''''-yläth-2'''''-yl)]-ester, Verfahren zur Herstellung derselben und diese enthaltende Arzneimittel
DE2005959A1 (de)	1970-08-06	7-Nitro-8-hydroxychinolinester, ihre Verwendung und Verfahren zur Herstellung derselben
DE2616351A1 (de)	1976-11-11	Halogenderivate
DE3025804C2 (de)	1985-09-05	1-S-Alkyl-2-0-acyl-3-phosphocholin-1-mercapto-2,3-propandiole, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
EP0007347B1 (de)	1981-12-30	Lipidsenkende Alkylenglykolderivate und Verfahren zu ihrer Herstellung
DE1294968B (de)	1969-05-14	Phloroglucinverbindungen und Verfahren zu ihrer Herstellung
DE2917890C2 (cs)	1987-10-29
CH620208A5 (en)	1980-11-14	Process for the preparation of anticarcinogenic dianhydrohexitide-acyl derivatives
DE1795740C2 (de)	1975-06-12	7-Chlor-7-deoxy-lincomycinderivate und pharmazeutischen Zusammensetzungen aus diesen Verbindungen und üblichen Trägerstoffen
DE2125113C3 (de)	1974-11-07	Bis-(4-chlorphenoxy)-essigsäure-(Nmethyl-pyrrolidyl-2)-methylester und dessen Säureanlagerungssalze, Verfahren zu seiner Herstellung sowie diesen enthaltende Arzneimittel