CH414583A - Verfahren zur Herstellung von zytostatisch wirkenden Heparinsalzen - Google Patents

Verfahren zur Herstellung von zytostatisch wirkenden Heparinsalzen

Info

Publication number: CH414583A
Authority: CH; Switzerland
Prior art keywords: heparin; compound; cytostatic; bis; cell metabolism
Prior art date: 1960-10-19

Application number

CH1174861A

Other languages

German (de)

English (en)

Inventor

Gyorgy Dr Med Csaba

Jeno Dr Korosi

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1960-10-19

Filing date

1961-10-11

Publication date

1966-06-15

1961-10-11 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1966-06-15 Publication of CH414583A publication Critical patent/CH414583A/de

Links

HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical class OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 title claims description 75
238000000034 method Methods 0.000 title claims description 23
239000000824 cytostatic agent Substances 0.000 title claims description 20
230000001085 cytostatic effect Effects 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title claims description 6
229920000669 heparin Polymers 0.000 claims description 63
229960002897 heparin Drugs 0.000 claims description 53
150000001875 compounds Chemical class 0.000 claims description 26
230000002401 inhibitory effect Effects 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 23
206010028980 Neoplasm Diseases 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 16
102000004190 Enzymes Human genes 0.000 claims description 12
108090000790 Enzymes Proteins 0.000 claims description 12
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 10
150000004044 tetrasaccharides Chemical group 0.000 claims description 10
230000019522 cellular metabolic process Effects 0.000 claims description 8
150000007514 bases Chemical class 0.000 claims description 7
230000004060 metabolic process Effects 0.000 claims description 6
235000001258 Cinchona calisaya Nutrition 0.000 claims description 5
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 5
229960000948 quinine Drugs 0.000 claims description 5
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 4
LYVCJABCMYQBPZ-UHFFFAOYSA-N NC=1C=C(C=CC1O)[AsH2]=O Chemical compound NC=1C=C(C=CC1O)[AsH2]=O LYVCJABCMYQBPZ-UHFFFAOYSA-N 0.000 claims description 3
230000023555 blood coagulation Effects 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 claims description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 claims 1
230000001476 alcoholic effect Effects 0.000 claims 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 1
239000011541 reaction mixture Substances 0.000 claims 1
239000000047 product Substances 0.000 description 23
239000000243 solution Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
MQXVYODZCMMZEM-ZYUZMQFOSA-N mannomustine Chemical compound ClCCNC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CNCCCl MQXVYODZCMMZEM-ZYUZMQFOSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
230000000694 effects Effects 0.000 description 13
229950008612 mannomustine Drugs 0.000 description 12
229910006069 SO3H Inorganic materials 0.000 description 10
239000000126 substance Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 8
208000037839 Solid Ehrlich Carcinoma Diseases 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
230000002378 acidificating effect Effects 0.000 description 7
230000002429 anti-coagulating effect Effects 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
210000004027 cell Anatomy 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
230000012010 growth Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000007858 starting material Substances 0.000 description 6
210000004881 tumor cell Anatomy 0.000 description 6
101710088194 Dehydrogenase Proteins 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
229940107700 pyruvic acid Drugs 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
230000004614 tumor growth Effects 0.000 description 4
IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 3
230000007423 decrease Effects 0.000 description 3
-1 hexoquinase Proteins 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
230000014508 negative regulation of coagulation Effects 0.000 description 3
BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 description 3
229960004257 sulfaguanidine Drugs 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
238000009423 ventilation Methods 0.000 description 3
YXYUHMRGKMUQAF-OXIHULNRSA-N Cl.Cl.C[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO Chemical compound Cl.Cl.C[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO YXYUHMRGKMUQAF-OXIHULNRSA-N 0.000 description 2
102000000634 Cytochrome c oxidase subunit IV Human genes 0.000 description 2
108050008072 Cytochrome c oxidase subunit IV Proteins 0.000 description 2
102000018832 Cytochromes Human genes 0.000 description 2
108010052832 Cytochromes Proteins 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
108090000854 Oxidoreductases Proteins 0.000 description 2
102000004316 Oxidoreductases Human genes 0.000 description 2
241000700159 Rattus Species 0.000 description 2
206010039491 Sarcoma Diseases 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
235000014655 lactic acid Nutrition 0.000 description 2
229920002521 macromolecule Polymers 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
238000012360 testing method Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000004580 weight loss Effects 0.000 description 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
HOSWABMJBUJVEQ-UHFFFAOYSA-N 4-dichloroarsanylaniline Chemical compound NC1=CC=C([As](Cl)Cl)C=C1 HOSWABMJBUJVEQ-UHFFFAOYSA-N 0.000 description 1
OSABEOFBNZMBDI-UHFFFAOYSA-N 4-n-(7-chloroquinolin-2-yl)-1-n,1-n-diethylpentane-1,4-diamine Chemical compound C1=CC(Cl)=CC2=NC(NC(C)CCCN(CC)CC)=CC=C21 OSABEOFBNZMBDI-UHFFFAOYSA-N 0.000 description 1
102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
108010029731 6-phosphogluconolactonase Proteins 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
206010003445 Ascites Diseases 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
102000016938 Catalase Human genes 0.000 description 1
108010053835 Catalase Proteins 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
108010050375 Glucose 1-Dehydrogenase Proteins 0.000 description 1
108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
229920001499 Heparinoid Polymers 0.000 description 1
OHJKXVLJWUPWQG-PNRHKHKDSA-N Heparinsodiumsalt Chemical compound O[C@@H]1[C@@H](NS(O)(=O)=O)[C@@H](O)O[C@H](COS(O)(=O)=O)[C@H]1O[C@H]1[C@H](OS(O)(=O)=O)[C@@H](O)[C@H](O)[C@H](C(O)=O)O1 OHJKXVLJWUPWQG-PNRHKHKDSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
206010025323 Lymphomas Diseases 0.000 description 1
GBKLAYXZNQSPBS-XYSQQLOGSA-N Mannomustine dihydrochloride Chemical compound Cl.Cl.ClCCNC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CNCCCl GBKLAYXZNQSPBS-XYSQQLOGSA-N 0.000 description 1
241000551546 Minerva Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
102000009569 Phosphoglucomutase Human genes 0.000 description 1
102000009097 Phosphorylases Human genes 0.000 description 1
108010073135 Phosphorylases Proteins 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
208000009916 Yoshida Sarcoma Diseases 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
150000005022 aminoacridines Chemical class 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
230000010100 anticoagulation Effects 0.000 description 1
239000003430 antimalarial agent Substances 0.000 description 1
229940033495 antimalarials Drugs 0.000 description 1
150000001495 arsenic compounds Chemical class 0.000 description 1
BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical group O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004891 communication Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000002900 effect on cell Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
229950006191 gluconic acid Drugs 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
102000006602 glyceraldehyde-3-phosphate dehydrogenase Human genes 0.000 description 1
108020004445 glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
239000002554 heparinoid Substances 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
239000003049 inorganic solvent Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
108091000115 phosphomannomutase Proteins 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1174861A 1960-10-19 1961-10-11 Verfahren zur Herstellung von zytostatisch wirkenden Heparinsalzen CH414583A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUEE000807		1960-10-19

Publications (1)

Publication Number	Publication Date
CH414583A true CH414583A (de)	1966-06-15

Family

ID=10995144

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1174861A CH414583A (de)	1960-10-19	1961-10-11	Verfahren zur Herstellung von zytostatisch wirkenden Heparinsalzen

Country Status (6)

Country	Link
BE (1)	BE609334A (fr)
BR (1)	BR6133547D0 (fr)
CH (1)	CH414583A (fr)
DK (1)	DK115214B (fr)
GB (1)	GB923052A (fr)
SE (1)	SE304504B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61502192A (ja) *	1984-05-21	1986-10-02	ボ−ダ−，ニコラス・エス	経口活性ヘパリン多重体

1961
- 1961-10-11 CH CH1174861A patent/CH414583A/de unknown
- 1961-10-13 GB GB3687461A patent/GB923052A/en not_active Expired
- 1961-10-18 DK DK414161A patent/DK115214B/da unknown
- 1961-10-19 BR BR13354761A patent/BR6133547D0/pt unknown
- 1961-10-19 BE BE609334A patent/BE609334A/fr unknown
- 1961-10-19 SE SE1036661A patent/SE304504B/xx unknown

Also Published As

Publication number	Publication date
SE304504B (fr)	1968-09-30
BE609334A (fr)	1962-02-15
DK115214B (da)	1969-09-15
BR6133547D0 (pt)	1973-05-31
GB923052A (en)	1963-04-10

Publication	Publication Date	Title
DE2833898C2 (fr)	1988-06-23
DE3102621C2 (fr)	1992-08-06
DE2948869A1 (de)	1980-07-03	Die mit cyclodextrin gebildeten einschlusskomplexe des allycins sowie verfahren zur herstellung dieser komplexe und diese enthaltende arzneimittelpraeparate
DE2731570B2 (de)	1979-07-26	Verfahren zur Gewinnung eines Polysaccharide mit therapeutischer Wirkung
DE1802162A1 (de)	1969-04-30	Neue N-Pyridylmethyliden-homocystein-thiolacton-Verbindung und Verfahren zu ihrer Herstellung
DE1129148B (de)	1962-05-10	Verfahren zur Herstellung von Heparin-Derivaten zytostatisch wirkender Stoffe
AT234278B (de)	1964-06-25	Verfahren zur Herstellung von neuen Heparinderivaten
DE2632115C2 (fr)	1988-11-10
DE2514533A1 (de)	1976-09-16	Polysaccharidkomplexe und verfahren zu deren herstellung
DE2422797A1 (de)	1974-12-12	Wasserloesliches pharmazeutisches mittel und verfahren zu seiner herstellung
DE2803681C2 (fr)	1989-03-16
DE3210638C2 (de)	1985-07-04	Chlorhexidin-di-2-pyrrolidon-5-carboxylat und pharmazeutische Zusammensetzungen
DE2347220C3 (de)	1978-06-08	L-Cystin-bis-[2,2-bis-(2-chloräthyl)-hydrazid] -dihydrobromid, Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel
US3244594A (en)	1966-04-05	1, 6-bis-(beta-chloro-ethyl-amino)-1, 6-deoxy-d-mannitol heparinate
DE3025656C2 (fr)	1989-06-22
DE2043817C3 (de)	1981-09-03	1,4-Dihydro-3-carboxy-cyclopentano-(h)-chinolon-(4)-derivate, Verfahren zu deren Herstellung sowie deren Verwendung zur Bekämpfung antibakterieller Erkrankungen
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DE865903C (de)	1953-02-05	Verfahren zur Herstellung schwefelhaltiger organischer Verbindungen
EP0051852B1 (fr)	1985-07-24	Pyrimido(4,5-b)(1,4)thiazines et procédé pour leur préparation
DE1239685B (de)	1967-05-03	Verfahren zur Herstellung von Neomycinpamoat
DE413381C (de)	1925-05-09	Verfahren zur Herstellung von in Wasser leicht loeslichen, bei Abwesenheit von Feuchtigkeit dauernd haltbaren Derivaten der Arsenobenzol- und Stibinobenzolreihe, sowie der ent-sprechenden gemischten Arsen-Antimon- und Arsen-Wismutverbindungen
DE2040143A1 (de)	1971-02-25	Neues unloesliches Kanamycinsalz