CS203946B2 - Method of producing n1-glucofuranosid-6-yl-n 3-nitrosoureas - Google Patents

Method of producing n1-glucofuranosid-6-yl-n 3-nitrosoureas Download PDF

Info

Publication number: CS203946B2
Authority: CS; Czechoslovakia
Prior art keywords: methyl; und; ethyl; deoxy; chloroform
Prior art date: 1978-02-21

Application number

CS791135A

Other languages

Czech (cs)

English (en)

Inventor

Jaroslav Stanek

Original Assignee

Ciba Geigy Ag

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.)

1978-02-21

Filing date

1979-02-20

Publication date

1981-03-31

1979-02-20 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1981-03-31 Publication of CS203946B2 publication Critical patent/CS203946B2/cs

Links

238000000034 method Methods 0.000 title claims description 8
229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 title claims description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
-1 phenyl- Chemical group 0.000 claims description 8
239000007858 starting material Substances 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000001118 alkylidene group Chemical group 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 2
125000006527 (C1-C5) alkyl group Chemical class 0.000 claims 1
206010043417 Therapeutic response unexpected Diseases 0.000 abstract 1
125000002252 acyl group Chemical group 0.000 abstract 1
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 33
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000012153 distilled water Substances 0.000 description 5
208000032839 leukemia Diseases 0.000 description 5
239000000203 mixture Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000008298 dragée Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
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239000008194 pharmaceutical composition Substances 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
ILSUNMIGPQOJMA-IGORNWKESA-N 1-[(2R)-2-[(2S,3R,4R,5S)-5-ethoxy-3,4-dihydroxyoxolan-2-yl]-2-methoxyethyl]-3-methylurea Chemical compound CCO[C@H]1O[C@H]([C@@H](CNC(=O)NC)OC)[C@H](O)[C@H]1O ILSUNMIGPQOJMA-IGORNWKESA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
AVVWPBAENSWJCB-IVMDWMLBSA-N D-glucofuranose Chemical compound OC[C@@H](O)[C@H]1OC(O)[C@H](O)[C@H]1O AVVWPBAENSWJCB-IVMDWMLBSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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241000699670 Mus sp. Species 0.000 description 2
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239000002202 Polyethylene glycol Substances 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
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239000003054 catalyst Substances 0.000 description 2
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238000000576 coating method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
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229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
XCHPVAASELNLDD-QCODTGAPSA-N (2S,3R,4R,5R)-5-[(1R)-2-azido-1-methoxyethyl]-2-ethoxy-4-phenylmethoxyoxolan-3-ol Chemical compound O[C@H]1[C@@H](OCC)O[C@H]([C@@H](CN=[N+]=[N-])OC)[C@@H]1OCC1=CC=CC=C1 XCHPVAASELNLDD-QCODTGAPSA-N 0.000 description 1
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
DCTBMJDDUARXIG-IVMDWMLBSA-N (3r,4r,5r)-5-[(1r)-2-amino-1-hydroxyethyl]oxolane-2,3,4-triol Chemical compound NC[C@@H](O)[C@H]1OC(O)[C@H](O)[C@H]1O DCTBMJDDUARXIG-IVMDWMLBSA-N 0.000 description 1
125000006833 (C1-C5) alkylene group Chemical group 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
229920001817 Agar Polymers 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
241000416162 Astragalus gummifer Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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 1
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 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
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 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
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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235000021355 Stearic acid Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
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DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
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229910052794 bromium Inorganic materials 0.000 description 1
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YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 description 1
229940062672 calcium dihydrogen phosphate Drugs 0.000 description 1
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HTPHKKKMEABKJE-UHFFFAOYSA-N calcium;octadecanoic acid Chemical compound [Ca].CCCCCCCCCCCCCCCCCC(O)=O HTPHKKKMEABKJE-UHFFFAOYSA-N 0.000 description 1
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229910052708 sodium Inorganic materials 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
230000005760 tumorsuppression Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Molecular Biology (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Genetics & Genomics (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Hematology (AREA)
Oncology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS791135A 1978-02-21 1979-02-20 Method of producing n1-glucofuranosid-6-yl-n 3-nitrosoureas CS203946B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH184978		1978-02-21

Publications (1)

Publication Number	Publication Date
CS203946B2 true CS203946B2 (en)	1981-03-31

Family

ID=4220040

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CS791135A CS203946B2 (en)	1978-02-21	1979-02-20	Method of producing n1-glucofuranosid-6-yl-n 3-nitrosoureas
CS797793A CS203947B2 (en)	1978-02-21	1979-02-20	Method of producing n 1-glucofuranosid-6-yl-n 3-nitrosoureas

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CS797793A CS203947B2 (en)	1978-02-21	1979-02-20	Method of producing n 1-glucofuranosid-6-yl-n 3-nitrosoureas

Country Status (23)

Country	Link
EP (1)	EP0003788B1 (es)
JP (1)	JPS54122226A (es)
KR (1)	KR820000419B1 (es)
AR (1)	AR227004A1 (es)
AT (1)	AT362389B (es)
AU (1)	AU525495B2 (es)
CA (1)	CA1123825A (es)
CS (2)	CS203946B2 (es)
CY (1)	CY1264A (es)
DE (1)	DE2961524D1 (es)
DK (1)	DK73579A (es)
ES (1)	ES477889A1 (es)
FI (1)	FI65782C (es)
GR (1)	GR74066B (es)
HK (1)	HK96984A (es)
HU (1)	HU179949B (es)
IL (1)	IL56696A (es)
NO (1)	NO146398C (es)
NZ (1)	NZ189703A (es)
PL (2)	PL117894B1 (es)
PT (1)	PT69253A (es)
SU (2)	SU913944A3 (es)
ZA (1)	ZA79803B (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3157684A (en) *	1961-02-13	1964-11-17	Atomic Energy Authority Uk	Tritiated-2-methyl-naphthaquinol-(1, 4)-diphosphoric acids
JPS5681596A (en) *	1979-12-07	1981-07-03	Tokyo Tanabe Co Ltd	Glucopyranose-nitrosourea derivative, carcinostatic agent consisting of the same and preparation
US4387220A (en) *	1980-11-05	1983-06-07	The Nissin Sugar Manufacturing Co., Ltd.	Nitrosourea derivatives of sucrose
FR2614304A1 (fr) *	1987-04-22	1988-10-28	Sanofi Sa	Derives de nitrosourees, leur nouveau procede de preparation et leurs applications therapeutiques.
PL233967B1 (pl)	2016-03-24	2019-12-31	Naturlen Spólka Z Ograniczona Odpowiedzialnoscia	Sposób wytwarzania materiału opatrunkowego z zastosowaniem włókien lnianych oraz materiał opatrunkowy z zastosowaniem włókien lnianych

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5175072A (ja) *	1974-12-18	1976-06-29	Tokyo Tanabe Co	Ribofuranoozunonitorosokarubamirujudotaino seizoho
JPS52151125A (en) *	1976-05-18	1977-12-15	Tokyo Tanabe Co	Process for manufacturing chloroethylnitrosourea derivatives of alkylglucopyranose
FI65781C (fi) *	1977-06-15	1984-07-10	Ciba Geigy Ag	Analogifoerfarande foer framstaellning av terapeutiskt verkande n1-glukofuranosid-6-yl-n3-nitroso-urinaemnen

1979
- 1979-02-12 EP EP79100400A patent/EP0003788B1/de not_active Expired
- 1979-02-12 CY CY1264A patent/CY1264A/xx unknown
- 1979-02-12 DE DE7979100400T patent/DE2961524D1/de not_active Expired
- 1979-02-19 FI FI790556A patent/FI65782C/fi not_active IP Right Cessation
- 1979-02-19 IL IL56696A patent/IL56696A/xx unknown
- 1979-02-19 CA CA321,736A patent/CA1123825A/en not_active Expired
- 1979-02-19 GR GR58402A patent/GR74066B/el unknown
- 1979-02-20 CS CS791135A patent/CS203946B2/cs unknown
- 1979-02-20 KR KR7900515A patent/KR820000419B1/ko not_active Expired
- 1979-02-20 HU HU79CI1915A patent/HU179949B/hu unknown
- 1979-02-20 DK DK73579A patent/DK73579A/da not_active Application Discontinuation
- 1979-02-20 AU AU44393/79A patent/AU525495B2/en not_active Ceased
- 1979-02-20 NZ NZ189703A patent/NZ189703A/xx unknown
- 1979-02-20 PT PT69253A patent/PT69253A/pt unknown
- 1979-02-20 ZA ZA79803A patent/ZA79803B/xx unknown
- 1979-02-20 SU SU792734802A patent/SU913944A3/ru active
- 1979-02-20 AT AT128979A patent/AT362389B/de not_active IP Right Cessation
- 1979-02-20 CS CS797793A patent/CS203947B2/cs unknown
- 1979-02-20 ES ES477889A patent/ES477889A1/es not_active Expired
- 1979-02-20 NO NO790564A patent/NO146398C/no unknown
- 1979-02-21 AR AR275566A patent/AR227004A1/es active
- 1979-02-21 PL PL1979219884A patent/PL117894B1/pl unknown
- 1979-02-21 PL PL1979213595A patent/PL117325B1/pl unknown
- 1979-02-21 JP JP1852679A patent/JPS54122226A/ja active Pending
- 1979-12-11 SU SU792853127A patent/SU1028250A3/ru active
1984
- 1984-12-13 HK HK969/84A patent/HK96984A/xx unknown

Also Published As

Publication number	Publication date
CA1123825A (en)	1982-05-18
CS203947B2 (en)	1981-03-31
ATA128979A (de)	1980-10-15
FI65782B (fi)	1984-03-30
PT69253A (de)	1979-03-01
KR820000419B1 (ko)	1982-04-01
HU179949B (en)	1983-01-28
GR74066B (es)	1984-06-06
HK96984A (en)	1984-12-21
SU913944A3 (en)	1982-03-15
PL219884A1 (es)	1980-07-14
AR227004A1 (es)	1982-09-15
EP0003788B1 (de)	1981-12-09
FI65782C (fi)	1984-07-10
ZA79803B (en)	1980-10-29
DK73579A (da)	1979-08-22
NZ189703A (en)	1981-07-13
AT362389B (de)	1981-05-11
CY1264A (en)	1984-11-23
FI790556A7 (fi)	1979-08-22
SU1028250A3 (ru)	1983-07-07
PL117894B1 (en)	1981-08-31
AU4439379A (en)	1979-08-30
AU525495B2 (en)	1982-11-11
IL56696A0 (en)	1979-05-31
NO790564L (no)	1979-08-22
PL213595A2 (es)	1980-04-08
IL56696A (en)	1982-08-31
PL117325B1 (en)	1981-07-31
EP0003788A2 (de)	1979-09-05
NO146398C (no)	1982-09-22
DE2961524D1 (en)	1982-02-04
ES477889A1 (es)	1979-08-01
EP0003788A3 (en)	1979-10-31
JPS54122226A (en)	1979-09-21
NO146398B (no)	1982-06-14

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EP0593536A1 (de)	1994-04-27	DIBENZ b,e]AZEPINDERIVATE UND DIESE ENTHALTENDE ARZNEIMITTEL
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