CH618164A5 - Process for the preparation of novel 1-(2',4',6'-trihydroxphenyl)-1,2-propanedione compounds substituted in the 3-position - Google Patents

Process for the preparation of novel 1-(2',4',6'-trihydroxphenyl)-1,2-propanedione compounds substituted in the 3-position Download PDF

Info

Publication number: CH618164A5
Authority: CH; Switzerland
Prior art keywords: compound; formula; compounds; och; hours
Prior art date: 1974-06-14

Application number

CH771375A

Other languages

German (de)

English (en)

Inventor

Rolf Dr Med Madaus

Guenter Dr Rer Nat Halbach

Vet Wilfried Dr Med Trost

Original Assignee

Madaus & Co Dr

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.)

1974-06-14

Filing date

1975-06-13

Publication date

1980-07-15

1975-06-13 Application filed by Madaus & Co Dr filed Critical Madaus & Co Dr

1980-07-15 Publication of CH618164A5 publication Critical patent/CH618164A5/de

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 4
150000001875 compounds Chemical group 0.000 claims abstract description 44
SEBFKMXJBCUCAI-HKTJVKLFSA-N silibinin Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC=C(C=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-HKTJVKLFSA-N 0.000 claims abstract description 27
SEBFKMXJBCUCAI-UHFFFAOYSA-N NSC 227190 Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC=C(C=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-UHFFFAOYSA-N 0.000 claims abstract description 19
BMLIIPOXVWESJG-UHFFFAOYSA-N silychristin A Natural products C1=C(O)C(OC)=CC(C2C(C3=C(C(=CC(=C3)C3C(C(=O)C4=C(O)C=C(O)C=C4O3)O)O)O2)CO)=C1 BMLIIPOXVWESJG-UHFFFAOYSA-N 0.000 claims abstract description 17
FDQAOULAVFHKBX-UHFFFAOYSA-N Isosilybin A Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC(=CC=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 FDQAOULAVFHKBX-UHFFFAOYSA-N 0.000 claims abstract description 10
VLGROHBNWZUINI-UHFFFAOYSA-N Silybin Natural products COc1cc(ccc1O)C2OC3C=C(C=CC3OC2CO)C4Oc5cc(O)cc(O)c5C(=O)C4O VLGROHBNWZUINI-UHFFFAOYSA-N 0.000 claims abstract description 10
229940043175 silybin Drugs 0.000 claims abstract description 10
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150000003839 salts Chemical class 0.000 claims abstract description 8
238000002844 melting Methods 0.000 claims abstract description 6
230000008018 melting Effects 0.000 claims abstract description 6
238000010438 heat treatment Methods 0.000 claims abstract description 5
239000002244 precipitate Substances 0.000 claims abstract description 5
239000000155 melt Substances 0.000 claims abstract description 4
150000007514 bases Chemical class 0.000 claims abstract description 3
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239000012299 nitrogen atmosphere Substances 0.000 claims description 2
239000002253 acid Substances 0.000 claims 2
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CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
208000019423 liver disease Diseases 0.000 abstract description 3
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CYGIJEJDYJOUAN-UHFFFAOYSA-N Isosilychristin Natural products C1=C(O)C(OC)=CC(C2C3C=C(C4C(C3=O)(O)OCC42)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 CYGIJEJDYJOUAN-UHFFFAOYSA-N 0.000 abstract 2
RIAZZJBPJQWPIS-UHFFFAOYSA-N Silychristin Natural products COc1cc(ccc1O)C2OC3C(C=C(C=C3O)C4Oc5cc(O)cc(O)c5C(=O)C4O)C2CO RIAZZJBPJQWPIS-UHFFFAOYSA-N 0.000 abstract 2
BMLIIPOXVWESJG-LMBCONBSSA-N silychristin Chemical compound C1=C(O)C(OC)=CC([C@H]2[C@@H](C3=C(C(=CC(=C3)[C@@H]3[C@H](C(=O)C4=C(O)C=C(O)C=C4O3)O)O)O2)CO)=C1 BMLIIPOXVWESJG-LMBCONBSSA-N 0.000 abstract 2
238000001035 drying Methods 0.000 abstract 1
238000001914 filtration Methods 0.000 abstract 1
230000002443 hepatoprotective effect Effects 0.000 abstract 1
230000003389 potentiating effect Effects 0.000 abstract 1
230000003019 stabilising effect Effects 0.000 abstract 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 24
KPKZJLCSROULON-QKGLWVMZSA-N Phalloidin Chemical compound N1C(=O)[C@@H]([C@@H](O)C)NC(=O)[C@H](C)NC(=O)[C@H](C[C@@](C)(O)CO)NC(=O)[C@H](C2)NC(=O)[C@H](C)NC(=O)[C@@H]3C[C@H](O)CN3C(=O)[C@@H]1CSC1=C2C2=CC=CC=C2N1 KPKZJLCSROULON-QKGLWVMZSA-N 0.000 description 24
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
241000699670 Mus sp. Species 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
239000001267 polyvinylpyrrolidone Substances 0.000 description 14
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 14
229920000036 polyvinylpyrrolidone Polymers 0.000 description 14
241001465754 Metazoa Species 0.000 description 12
108010009711 Phalloidine Proteins 0.000 description 12
229960004245 silymarin Drugs 0.000 description 9
235000017700 silymarin Nutrition 0.000 description 9
239000000243 solution Substances 0.000 description 8
230000004083 survival effect Effects 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
101710098398 Probable alanine aminotransferase, mitochondrial Proteins 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000000694 effects Effects 0.000 description 6
238000012360 testing method Methods 0.000 description 6
206010067125 Liver injury Diseases 0.000 description 5
231100000234 hepatic damage Toxicity 0.000 description 5
230000008818 liver damage Effects 0.000 description 5
231100000572 poisoning Toxicity 0.000 description 5
230000000607 poisoning effect Effects 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
210000004185 liver Anatomy 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003651 drinking water Substances 0.000 description 3
235000020188 drinking water Nutrition 0.000 description 3
229940088598 enzyme Drugs 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
239000011550 stock solution Substances 0.000 description 3
238000002211 ultraviolet spectrum Methods 0.000 description 3
-1 3-hydroxyphenylchromanone compound Chemical class 0.000 description 2
102100025490 Slit homolog 1 protein Human genes 0.000 description 2
101710123186 Slit homolog 1 protein Proteins 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
230000001629 suppression Effects 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
UPLLQJUZZIYKHI-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;2-oxobutanedioic acid Chemical compound OC(=O)CC(=O)C(O)=O.OC(=O)[C@@H](N)CCC(O)=O UPLLQJUZZIYKHI-DFWYDOINSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
102000003929 Transaminases Human genes 0.000 description 1
108090000340 Transaminases Proteins 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
229940124599 anti-inflammatory drug Drugs 0.000 description 1
230000002921 anti-spasmodic effect Effects 0.000 description 1
229940124575 antispasmodic agent Drugs 0.000 description 1
UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
239000002775 capsule Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001989 choleretic effect Effects 0.000 description 1
230000002498 deadly effect Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
229940124568 digestive agent Drugs 0.000 description 1
230000001079 digestive effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000002360 explosive Substances 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
150000002337 glycosamines Chemical class 0.000 description 1
150000002391 heterocyclic compounds Chemical class 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
238000010253 intravenous injection Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
229960001553 phloroglucinol Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
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229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
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238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Gastroenterology & Hepatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Furan Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)

CH771375A 1974-06-14 1975-06-13 Process for the preparation of novel 1-(2',4',6'-trihydroxphenyl)-1,2-propanedione compounds substituted in the 3-position CH618164A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2428680A DE2428680C2 (de)	1974-06-14	1974-06-14	1-(2',4',6'-Trihydroxyphenyl)-propandion-(1,2)-Verbindungen, Verfahren zu deren Herstellung und Arzneimittel, die diese Verbindungen enthalten

Publications (1)

Publication Number	Publication Date
CH618164A5 true CH618164A5 (en)	1980-07-15

Family

ID=5918092

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH771375A CH618164A5 (en)	1974-06-14	1975-06-13	Process for the preparation of novel 1-(2',4',6'-trihydroxphenyl)-1,2-propanedione compounds substituted in the 3-position

Country Status (15)

Country	Link
US (1)	US4168318A (it)
JP (1)	JPS5111755A (it)
AT (1)	AT348521B (it)
BE (1)	BE830154A (it)
CA (1)	CA1049021A (it)
CH (1)	CH618164A5 (it)
DE (1)	DE2428680C2 (it)
ES (1)	ES438537A1 (it)
FI (1)	FI63755C (it)
FR (1)	FR2274297A1 (it)
GB (1)	GB1504758A (it)
IT (1)	IT1054625B (it)
NL (1)	NL7506998A (it)
SE (1)	SE418400B (it)
ZA (1)	ZA753829B (it)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2840467A1 (de) *	1978-09-16	1980-03-20	Madaus & Co Dr	3,4-dihydroxizimtaldehydderivat, dessen herstellung und arzneimittel
DE69921464D1 (de) *	1998-04-29	2004-12-02	Choongwae Pharmaceutical Co	Dihydroxyphenylderivate zum schutze der leber und zur behandlung von lebererkrankungen
US6693126B2 (en)	2000-10-27	2004-02-17	Choongwae Pharm. Co., Ltd.	Dihydroxyphenyl derivatives for hepatoprotection and treatment of liver diseases

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB966866A (en) *	1960-12-13	1964-08-19	Angeli Inst Spa	2-benzodioxan-methyl hydrazines and their hydrazones
US3117978A (en) *	1961-01-25	1964-01-14	Lakeside Lab Inc	1, 4-benzodioxane-2-carboxamides
DE1518042C3 (de) *	1965-11-11	1975-04-10	Merck Patent Gmbh, 6100 Darmstadt	1,4-Benzodioxanderivate und Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel
DE1923082C3 (de) *	1969-05-06	1985-08-22	Dr. Madaus & Co, 5000 Koeln	Verfahren zur Gewinnung von Polyhydroxyphenylchromanonen (Silymarin I-IV) und Arzneimittel enthaltend das Polyhydroxyphenylchromanon (Silymarin I-IV = Silymarin I-IV-Gruppe)Gemisch
GB1307390A (en) *	1970-09-24	1973-02-21	Ward Blenkinsop & Co Ltd	Benzodioxanes

1974
- 1974-06-14 DE DE2428680A patent/DE2428680C2/de not_active Expired
1975
- 1975-05-22 GB GB22205/75A patent/GB1504758A/en not_active Expired
- 1975-05-27 IT IT23749/75A patent/IT1054625B/it active
- 1975-05-29 FI FI751575A patent/FI63755C/fi not_active IP Right Cessation
- 1975-06-10 FR FR7518116A patent/FR2274297A1/fr active Granted
- 1975-06-12 BE BE157261A patent/BE830154A/xx not_active IP Right Cessation
- 1975-06-12 NL NL7506998A patent/NL7506998A/xx unknown
- 1975-06-12 SE SE7506729A patent/SE418400B/xx not_active IP Right Cessation
- 1975-06-13 ES ES438537A patent/ES438537A1/es not_active Expired
- 1975-06-13 CH CH771375A patent/CH618164A5/de not_active IP Right Cessation
- 1975-06-13 JP JP50071826A patent/JPS5111755A/ja active Granted
- 1975-06-13 CA CA75229250A patent/CA1049021A/en not_active Expired
- 1975-06-16 AT AT458875A patent/AT348521B/de not_active IP Right Cessation
- 1975-06-16 ZA ZA00753829A patent/ZA753829B/xx unknown
1977
- 1977-05-02 US US05/793,113 patent/US4168318A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ZA753829B (en)	1976-06-30
BE830154A (fr)	1975-12-12
US4168318A (en)	1979-09-18
DE2428680C2 (de)	1983-02-17
GB1504758A (en)	1978-03-22
JPS5538948B2 (it)	1980-10-07
FI751575A (it)	1975-12-15
IT1054625B (it)	1981-11-30
ES438537A1 (es)	1977-01-16
SE7506729L (sv)	1975-12-15
ATA458875A (de)	1978-07-15
JPS5111755A (en)	1976-01-30
AT348521B (de)	1979-02-26
DE2428680A1 (de)	1976-01-02
FR2274297B1 (it)	1983-02-18
NL7506998A (nl)	1975-12-16
FR2274297A1 (fr)	1976-01-09
CA1049021A (en)	1979-02-20
FI63755C (fi)	1983-08-10
FI63755B (fi)	1983-04-29
SE418400B (sv)	1981-05-25

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DE2635853A1 (de)	1977-02-24	Pyrrolidin-2-on-derivate, verfahren zu ihrer herstellung und sie enthaltendes arzneimittel
DE3883387T2 (de)	1993-12-09	Bis(methylendioxy)biphenyl-Verbindungen.
CH656875A5 (de)	1986-07-31	Amide von carbonsaeuren und ihre derivate.
DE2616616A1 (de)	1976-10-28	1-(triarylalklyl)-4-phenylpiperidinderivate, verfahren zu ihrer herstellung und pharmazeutische zubereitungen, die diese verbindungen enthalten
DE1908548A1 (de)	1970-11-05	Chinolinderivate
DE3320394A1 (de)	1983-12-08	Optisch aktive n-arylierte oxazolidinon-(2)-derivate, deren verwendung als spezifische und reversible inhibitoren von monoaminooxydase des b-typs sowie verfahren zu deren herstellung
DE2928594C2 (de)	1982-09-02	3-Hydroxy-4-(hydroxymethyl)-benzoesäure, deren Salze, Hydrate und Hydratsalze, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE2446100C3 (de)	1982-01-14	Phenoxyalkancarbonsäureamide von Thiazolidincarbonsäuren, Verfahren zu ihrer Herstellung und Arzneimittel
CH621780A5 (it)	1981-02-27
CH618164A5 (en)	1980-07-15	Process for the preparation of novel 1-(2',4',6'-trihydroxphenyl)-1,2-propanedione compounds substituted in the 3-position
DE2413125C2 (de)	1983-06-30	Indolylacetylaminosäurederivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneipräparate
DE2038628C3 (de)	1979-08-16	N,N'-Di(carboxyalkyI)-p-phenylendiamine, deren Salze und Diäthylester, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2557220A1 (de)	1977-06-23	N-substituierte spirolactame
DE69706012T2 (de)	2002-05-29	N-Acylpiperazinderivat, antibakterielle und gegen Geschwüre wirksame Medikamente
DE2911377C3 (de)	1982-03-18	3-Hydroxy-4-hydroxymethyl-phenylglycin (Forphenicinol), dessen Hydrate und Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2004301A1 (de)	1970-09-03	Phenylserinderivate
DE2407016A1 (de)	1974-09-05	2-alkoxybenzoylaminosaeuren, verfahren zur herstellung derselben und antipyretisches mittel mit einem gehalt derselben
DD253616A5 (de)	1988-01-27	Verfahren zur herstellung von neuen pleunromutilinderivaten
DE2423725A1 (de)	1975-11-27	5-phenyl-4-oxo-delta hoch 2,alphathiazolidinessigsaeureester
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DE1618042C (it)	1973-02-08
DE2113489B2 (de)	1979-08-30	2-Nitro-benzofuranderivate, ein Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
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1991-06-14	PFA	Name/firm changed	Owner name: DR. MADAUS GMBH & CO.
1991-06-14	PUE	Assignment	Owner name: MADAUS AG
1994-02-28	PL	Patent ceased
2024-10-31	PL	Patent ceased