CH623042A5 - Process for the preparation of novel quinoxaline-1,4-dioxide derivatives - Google Patents

Process for the preparation of novel quinoxaline-1,4-dioxide derivatives Download PDF

Info

Publication number: CH623042A5
Authority: CH; Switzerland
Prior art keywords: formula; quinoxaline; group; formyl; dioxide
Prior art date: 1974-11-21

Application number

CH1484575A

Other languages

German (de)

English (en)

Inventor

Pal Dr Benko

Ildiko Simonek

Laszlo Dr Pallos

Jeno Dr Kovacs

Karoly Dr Magyar

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.)

1974-11-21

Filing date

1975-11-17

Publication date

1981-05-15

1975-11-17 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1981-05-15 Publication of CH623042A5 publication Critical patent/CH623042A5/de

Links

238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 4
CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 title claims description 3
-1 methanol 2-formyl-quinoxaline-1,4-dioxide hydrazones Chemical class 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 4
230000000844 anti-bacterial effect Effects 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
230000004584 weight gain Effects 0.000 claims description 3
235000019786 weight gain Nutrition 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 1
WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
244000144972 livestock Species 0.000 claims 1
125000005936 piperidyl group Chemical group 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
239000000047 product Substances 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
239000007900 aqueous suspension Substances 0.000 description 6
JZJFIUXMPBVEFS-UHFFFAOYSA-N 1-oxido-4-oxoquinoxalin-4-ium-2-carbaldehyde Chemical compound C1=CC=C2N([O-])C(C=O)=C[N+](=O)C2=C1 JZJFIUXMPBVEFS-UHFFFAOYSA-N 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
FLHXVKZDKJAVMB-UHFFFAOYSA-N 2-naphthalen-1-ylacetohydrazide Chemical compound C1=CC=C2C(CC(=O)NN)=CC=CC2=C1 FLHXVKZDKJAVMB-UHFFFAOYSA-N 0.000 description 1
FPTCVTJCJMVIDV-UHFFFAOYSA-N 2-phenylacetohydrazide Chemical compound NNC(=O)CC1=CC=CC=C1 FPTCVTJCJMVIDV-UHFFFAOYSA-N 0.000 description 1
UEIZUEWXLJOVLD-UHFFFAOYSA-N 3-(1-methylpyrrolidin-3-yl)pyridine Chemical compound C1N(C)CCC1C1=CC=CN=C1 UEIZUEWXLJOVLD-UHFFFAOYSA-N 0.000 description 1
NQEWXLVDAVTOHM-UHFFFAOYSA-N 3-nitrobenzohydrazide Chemical compound NNC(=O)C1=CC=CC([N+]([O-])=O)=C1 NQEWXLVDAVTOHM-UHFFFAOYSA-N 0.000 description 1
LSSUJBFVEXWEEC-UHFFFAOYSA-N 3-phenylpropanehydrazide Chemical compound NNC(=O)CCC1=CC=CC=C1 LSSUJBFVEXWEEC-UHFFFAOYSA-N 0.000 description 1
WPBZMCGPFHZRHJ-UHFFFAOYSA-N 4-aminobenzohydrazide Chemical compound NNC(=O)C1=CC=C(N)C=C1 WPBZMCGPFHZRHJ-UHFFFAOYSA-N 0.000 description 1
PKBGHORNUFQAAW-UHFFFAOYSA-N 4-chlorobenzohydrazide Chemical compound NNC(=O)C1=CC=C(Cl)C=C1 PKBGHORNUFQAAW-UHFFFAOYSA-N 0.000 description 1
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
ZMZGIVVRBMFZSG-UHFFFAOYSA-N 4-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=C(O)C=C1 ZMZGIVVRBMFZSG-UHFFFAOYSA-N 0.000 description 1
REKQLYUAUXYJSZ-UHFFFAOYSA-N 4-methoxybenzohydrazide Chemical compound COC1=CC=C(C(=O)NN)C=C1 REKQLYUAUXYJSZ-UHFFFAOYSA-N 0.000 description 1
HRYYAHKXNSUDFH-UHFFFAOYSA-N 5-nitrofuran-2-carbohydrazide Chemical compound NNC(=O)C1=CC=C([N+]([O-])=O)O1 HRYYAHKXNSUDFH-UHFFFAOYSA-N 0.000 description 1
RGHDGRGJOSPDHW-UHFFFAOYSA-N 8-benzyl-1-(4-chlorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=CC(Cl)=CC=C1N1C2(CCN(CC=3C=CC=CC=3)CC2)C(=O)NC1 RGHDGRGJOSPDHW-UHFFFAOYSA-N 0.000 description 1
OVGGLBAWFMIPPY-WUXMJOGZSA-N Carbadox Chemical compound C1=CC=CC2=[N+]([O-])C(/C=N/NC(=O)OC)=C[N+]([O-])=C21 OVGGLBAWFMIPPY-WUXMJOGZSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000282887 Suidae Species 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000031018 biological processes and functions Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229960000427 carbadox Drugs 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
YTQHSQQSLTYMSL-UHFFFAOYSA-N dodecanohydrazide Chemical compound CCCCCCCCCCCC(=O)NN YTQHSQQSLTYMSL-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229940091173 hydantoin Drugs 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
BPMVRAQIQQEBLN-OBPBNMOMSA-N methyl n-[(e)-(1-hydroxy-4-oxidoquinoxalin-4-ium-2-ylidene)methyl]iminocarbamate Chemical compound C1=CC=C2N(O)C(=C/N=NC(=O)OC)/C=[N+]([O-])C2=C1 BPMVRAQIQQEBLN-OBPBNMOMSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 1
229960000564 nitrofurantoin Drugs 0.000 description 1
BYTFESSQUGDMQQ-UHFFFAOYSA-N octadecanehydrazide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NN BYTFESSQUGDMQQ-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
ARKTVCBOWGYYFS-UHFFFAOYSA-N piperidine-4-carbohydrazide Chemical compound NNC(=O)C1CCNCC1 ARKTVCBOWGYYFS-UHFFFAOYSA-N 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000003696 stearoyl group Chemical group O=C([*])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([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 description 1
229960003053 thiamphenicol Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1484575A 1974-11-21 1975-11-17 Process for the preparation of novel quinoxaline-1,4-dioxide derivatives CH623042A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUEE2278A HU169299B (da)	1974-11-21	1974-11-21

Publications (1)

Publication Number	Publication Date
CH623042A5 true CH623042A5 (en)	1981-05-15

Family

ID=10995579

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1484575A CH623042A5 (en)	1974-11-21	1975-11-17	Process for the preparation of novel quinoxaline-1,4-dioxide derivatives

Country Status (19)

Country	Link
JP (1)	JPS6049634B2 (da)
AT (1)	AT344702B (da)
BE (1)	BE835763A (da)
CH (1)	CH623042A5 (da)
CS (1)	CS232703B2 (da)
DD (1)	DD123604A5 (da)
DE (1)	DE2552289C2 (da)
DK (1)	DK138389B (da)
FI (1)	FI61887C (da)
FR (1)	FR2291756A1 (da)
GB (1)	GB1479239A (da)
HU (1)	HU169299B (da)
IL (1)	IL48463A (da)
IN (1)	IN140110B (da)
NL (1)	NL7513446A (da)
PL (1)	PL96412B1 (da)
SE (2)	SE423095B (da)
SU (1)	SU612628A3 (da)
YU (1)	YU39953B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1058490B (it) *	1976-03-18	1982-04-10	Ind Chimica Prodotti Francis S	Procedimento di fabbricazione di alchil 3 2 chinossalinilmetilen carbazato 1.4 diossido
HU184772B (en) *	1980-05-23	1984-10-29	Egyt Gyogyszervegyeszeti Gyar	Process for preparing quinoxaline-1,4-dioxide derivatives
HU184825B (en) *	1980-09-12	1984-10-29	Egyt Gyogyszervegyeszeti Gyar	Process for preparing new 2-hydroxy-methyl-quinoxaline-1,4-dioxide derivatives
JPS6276527A (ja) *	1985-09-30	1987-04-08	Toshiba Corp	ワイヤボンデイングキヤピラリ
EP0370065A1 (en) *	1987-07-31	1990-05-30	The Upjohn Company	Anthelmintic acylhydrazones, method of use and compositions
US5049561A (en) *	1987-07-31	1991-09-17	The Upjohn Company	Anthelmintic acylhydrazones, method of use and compositions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1469485A (fr) *	1964-09-16	1967-02-17	Pfizer & Co C	Procédé pour la préparation d'une nouvelle série de bases de schiff
US3371090A (en) *	1964-09-16	1968-02-27	Pfizer & Co C	Novel antibacterial agents

1974
- 1974-11-21 HU HUEE2278A patent/HU169299B/hu not_active IP Right Cessation
1975
- 1975-11-11 IL IL48463A patent/IL48463A/xx unknown
- 1975-11-14 IN IN2177/CAL/75A patent/IN140110B/en unknown
- 1975-11-14 SE SE7512857A patent/SE423095B/xx unknown
- 1975-11-17 CH CH1484575A patent/CH623042A5/de not_active IP Right Cessation
- 1975-11-17 FI FI753225A patent/FI61887C/fi not_active IP Right Cessation
- 1975-11-17 AT AT872275A patent/AT344702B/de not_active IP Right Cessation
- 1975-11-18 GB GB47418/75A patent/GB1479239A/en not_active Expired
- 1975-11-18 DK DK518275AA patent/DK138389B/da unknown
- 1975-11-18 FR FR7535184A patent/FR2291756A1/fr active Granted
- 1975-11-18 NL NL7513446A patent/NL7513446A/xx not_active Application Discontinuation
- 1975-11-19 SU SU752189810A patent/SU612628A3/ru active
- 1975-11-19 CS CS757830A patent/CS232703B2/cs unknown
- 1975-11-20 YU YU2942/75A patent/YU39953B/xx unknown
- 1975-11-20 DD DD189588A patent/DD123604A5/xx unknown
- 1975-11-20 PL PL1975184870A patent/PL96412B1/pl unknown
- 1975-11-20 BE BE162030A patent/BE835763A/xx not_active IP Right Cessation
- 1975-11-21 DE DE2552289A patent/DE2552289C2/de not_active Expired
- 1975-11-21 JP JP50139369A patent/JPS6049634B2/ja not_active Expired
1979
- 1979-01-16 SE SE7900389A patent/SE423387B/sv unknown

Also Published As

Publication number	Publication date
DE2552289C2 (de)	1986-05-07
JPS6049634B2 (ja)	1985-11-02
CS232703B2 (en)	1985-02-14
GB1479239A (en)	1977-07-06
FI61887C (fi)	1982-10-11
DD123604A5 (da)	1977-01-05
PL96412B1 (pl)	1977-12-31
IL48463A (en)	1978-10-31
DE2552289A1 (de)	1976-05-26
FI753225A (da)	1976-05-22
SE423387B (sv)	1982-05-03
AT344702B (de)	1977-12-15
NL7513446A (nl)	1976-05-25
SE423095B (sv)	1982-04-13
ATA872275A (de)	1977-12-15
DK518275A (da)	1976-05-22
FR2291756A1 (fr)	1976-06-18
IL48463A0 (en)	1976-01-30
HU169299B (da)	1976-11-28
YU294275A (en)	1982-06-30
SE7900389L (sv)	1979-01-16
DK138389C (da)	1979-02-05
FR2291756B1 (da)	1978-11-10
JPS5175082A (en)	1976-06-29
DK138389B (da)	1978-08-28
IN140110B (da)	1976-09-18
YU39953B (en)	1985-06-30
BE835763A (fr)	1976-03-16
FI61887B (fi)	1982-06-30
SE7512857L (sv)	1976-05-24
SU612628A3 (ru)	1978-06-25

Publication	Publication Date	Title
DE2458965B2 (de)	1979-02-22	3-Amino-indazol-N-carbonsäure-Derivate, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel
DE1795699C3 (da)	1975-12-18
DE2162011C3 (de)	1981-12-17	2-Phenyl-3-(4-methyl-piperazinocarbonyloxy)-1-isoindolinon-derivate, ihre Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
DE2829580C2 (de)	1985-10-24	2-Formylchinoxalin-1,4-dioxid-cyanoacetylhydrazon, Verfahren zu seiner Herstellung und Zusammensetzungen mit dieser Verbindung
DE2239815C2 (de)	1983-02-10	2-Alkylamino-dihydropyridine, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel
CH623042A5 (en)	1981-05-15	Process for the preparation of novel quinoxaline-1,4-dioxide derivatives
DE2446100C3 (de)	1982-01-14	Phenoxyalkancarbonsäureamide von Thiazolidincarbonsäuren, Verfahren zu ihrer Herstellung und Arzneimittel
DD247448A5 (de)	1987-07-08	Verfahren zur herstellung neuer chinolinderivate
DE1670163C3 (de)	1973-11-29	Cephaloglycindenvat und Verfahren zu seiner Herstellung
DE2322561A1 (de)	1973-11-15	Trisubstituierte imidazole
DE2354931C2 (de)	1983-12-08	trans-2-Phenylbicyclooctan-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
CH648025A5 (de)	1985-02-28	Chinoxalin-1,4-dioxyd-derivate.
DE2111710B2 (de)	1979-01-25	1 ^-Dioxido-S-methyl-chinoxalin-2-carbonsäure-2-hydroxyethylester und denselben enthaltendes Tierfutter oder denselben enthaltender Tiertrank
DE2147103C3 (de)	1975-07-17	Imidazo eckige Klammer auf 4,5-b eckige Klammer zu pyridine
DE1695231B1 (de)	1972-05-04	3-Carbalkoxy-4-hydroxy-chinolinderivate
DE1445438C (da)	1973-08-30
DE1795487C3 (de)	1974-09-05	5-Nitrofuran-Derivate. Ausscheidung aus: 1445556
AT205977B (de)	1959-10-26	Verfahren zur Herstellung von neuen, heterocyclischen Hydrazinderivaten
AT233310B (de)	1964-05-11	Coccidiostatische Zubereitungen
DE1296650B (de)	1969-06-04	N, N-disubstituierte Thienyl-(2)- bzw. Thienyl-(3)-propionsaeure- und -acrylsaeureamidine sowie Verfahren zu ihrer Herstellung
DE2747121A1 (de)	1978-04-27	6-(m-aminophenyl-2,3,5,6-tetrahydroimidazo eckige klammer auf 2,1-b eckige klammer zu thiazolderivate, verfahren zu ihrer herstellung und ihre verwendung
DE2536387A1 (de)	1977-02-24	Pyrido(3,2-e)-as-triazinderivate, solche enthaltende arzneimittel sowie verfahren zur herstellung derselben
AT266116B (de)	1968-11-11	Verfahren zur Herstellung von neuen aliphatischen α-(3-Indolyl)-carbonsäuren und ihren Salzen
AT364836B (de)	1981-11-25	Verfahren zur herstellung von neuen o-substituierten derivaten des (+)-cyanidan-3-ols und deren salzen
AT360990B (de)	1981-02-10	Verfahren zur herstellung des neuen 1-methyl-4- (3-carboxy-10,11-dihydro-5h-dibenzo-(a,d)- -cyclohepten-5-yliden)-piperidin (10,11-dihydro -3-carboxy-cyproheptadin), seines n-oxids und seiner salze

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