DD145534A5 - Verfahren zur herstellung von 1,3-benzoxazin-2,4-dion-derivaten - Google Patents

Verfahren zur herstellung von 1,3-benzoxazin-2,4-dion-derivaten Download PDF

Info

Publication number: DD145534A5
Authority: DD; German Democratic Republic
Prior art keywords: dione; benzoxazine; chloro; general formula; group
Prior art date: 1978-08-25

Application number

DD79215096A

Other languages

German (de)

English (en)

Inventor

Antonio Esteve-Subirana

Original Assignee

Provesan Sa

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.)

1978-08-25

Filing date

1979-08-21

Publication date

1980-12-17

1979-08-21 Application filed by Provesan Sa filed Critical Provesan Sa

1980-12-17 Publication of DD145534A5 publication Critical patent/DD145534A5/de

Links

238000002360 preparation method Methods 0.000 title claims description 8
238000000034 method Methods 0.000 title claims description 6
OAYRYNVEFFWSHK-UHFFFAOYSA-N carsalam Chemical class C1=CC=C2OC(=O)NC(=O)C2=C1 OAYRYNVEFFWSHK-UHFFFAOYSA-N 0.000 title claims description 3
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 12
-1 alkyl radical Chemical class 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
150000003872 salicylic acid derivatives Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 1
150000003254 radicals Chemical class 0.000 claims 1
239000000460 chlorine Substances 0.000 description 16
230000000202 analgesic effect Effects 0.000 description 8
239000000243 solution Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
208000002193 Pain Diseases 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000000829 suppository Substances 0.000 description 3
229910002016 Aerosil® 200 Inorganic materials 0.000 description 2
229920003084 Avicel® PH-102 Polymers 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229940080018 acetylcholine injection Drugs 0.000 description 2
230000001754 anti-pyretic effect Effects 0.000 description 2
239000002221 antipyretic Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000008177 pharmaceutical agent Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 1
GMFBXDUNANTIIL-UHFFFAOYSA-N 5-chloro-2-hydroxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC(Cl)=CC=C1O GMFBXDUNANTIIL-UHFFFAOYSA-N 0.000 description 1
GBNWQQUVAPTWKO-UHFFFAOYSA-N 6-chloro-3-methyl-1,3-benzoxazine-2,4-dione Chemical compound C1=C(Cl)C=C2C(=O)N(C)C(=O)OC2=C1 GBNWQQUVAPTWKO-UHFFFAOYSA-N 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
229910014570 C—OH Inorganic materials 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
206010058667 Oral toxicity Diseases 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical class NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
ZEHGKSPCAMLJDC-UHFFFAOYSA-M acetylcholine bromide Chemical compound [Br-].CC(=O)OCC[N+](C)(C)C ZEHGKSPCAMLJDC-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940125716 antipyretic agent Drugs 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012458 free base Substances 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229940090044 injection Drugs 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
230000002175 menstrual effect Effects 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
XBECFEJUQZXMFE-UHFFFAOYSA-N n-(4-aminobutyl)acetamide;hydrochloride Chemical compound Cl.CC(=O)NCCCCN XBECFEJUQZXMFE-UHFFFAOYSA-N 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
239000002547 new drug Substances 0.000 description 1
231100000418 oral toxicity Toxicity 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000523 sample Substances 0.000 description 1
230000001932 seasonal effect Effects 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
208000004371 toothache Diseases 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth 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)
Pain & Pain Management (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Rheumatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD79215096A 1978-08-25 1979-08-21 Verfahren zur herstellung von 1,3-benzoxazin-2,4-dion-derivaten DD145534A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7824674A FR2434158A1 (fr)	1978-08-25	1978-08-25	Nouveaux derives de 1,3-benzoxazine-2,4-dione, leur preparation et leur application en tant que medicaments

Publications (1)

Publication Number	Publication Date
DD145534A5 true DD145534A5 (de)	1980-12-17

Family

ID=9212085

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79215096A DD145534A5 (de)	1978-08-25	1979-08-21	Verfahren zur herstellung von 1,3-benzoxazin-2,4-dion-derivaten

Country Status (25)

Country	Link
JP (1)	JPS5533484A (cs)
AR (1)	AR222494A1 (cs)
AT (1)	AT373591B (cs)
BE (1)	BE878395A (cs)
BG (1)	BG30929A3 (cs)
CA (1)	CA1128511A (cs)
CH (1)	CH643548A5 (cs)
CS (1)	CS208131B2 (cs)
DD (1)	DD145534A5 (cs)
DE (1)	DE2934166A1 (cs)
EG (1)	EG14355A (cs)
ES (1)	ES481856A1 (cs)
FI (1)	FI68818C (cs)
FR (1)	FR2434158A1 (cs)
GB (1)	GB2031410B (cs)
GR (1)	GR69619B (cs)
HU (1)	HU182916B (cs)
IL (1)	IL58096A (cs)
NL (1)	NL7906408A (cs)
PL (1)	PL116771B1 (cs)
PT (1)	PT70107A (cs)
RO (1)	RO78156A (cs)
SE (1)	SE446865B (cs)
SU (1)	SU797576A3 (cs)
YU (1)	YU40849B (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101849953B (zh)	2000-12-18	2012-04-25	株式会社医药分子设计研究所	炎症性细胞因子产生游离抑制剂
CN1658872B (zh)	2002-06-06	2010-09-22	株式会社医药分子设计研究所	抗过敏药
AU2003242118B2 (en) *	2002-06-06	2008-09-11	Institute Of Medicinal Molecular Design, Inc	O-substituted hydroxyaryl derivatives
CN108658887B (zh) *	2018-06-20	2022-04-05	中南大学	苯并[d][1,3]噁嗪-2,4(1H)-二酮衍生物及其合成方法和用途

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2476559A (en) *	1946-10-01	1949-07-19	Gen Aniline & Film Corp	Oxazine diones
DE1153375B (de) *	1960-05-25	1963-08-29	Thomae Gmbh Dr K	Verfahren zur Herstellung von Benzoxazin-(1, 3)-dionen-(2, 4)
GB1069367A (en) *	1964-10-01	1967-05-17	Aspro Nicholas Ltd	Improvements in or relating to the production of 1:3-benzoxazine-2:4-dione
CH459211A (de) *	1965-01-25	1968-07-15	Robapharm Ag	Verfahren zur Herstellung von neuen basischen Derivaten des Dihydro-1,3-benzoxazin-2,4-dions

1978
- 1978-08-25 FR FR7824674A patent/FR2434158A1/fr active Granted
1979
- 1979-06-06 ES ES481856A patent/ES481856A1/es not_active Expired
- 1979-08-21 DD DD79215096A patent/DD145534A5/de not_active IP Right Cessation
- 1979-08-22 RO RO7998518A patent/RO78156A/ro unknown
- 1979-08-22 HU HU79PO694A patent/HU182916B/hu not_active IP Right Cessation
- 1979-08-22 BG BG044725A patent/BG30929A3/xx unknown
- 1979-08-22 GB GB7929266A patent/GB2031410B/en not_active Expired
- 1979-08-22 CA CA334,287A patent/CA1128511A/fr not_active Expired
- 1979-08-22 PL PL1979217893A patent/PL116771B1/pl unknown
- 1979-08-22 GR GR52886A patent/GR69619B/el unknown
- 1979-08-23 PT PT70107A patent/PT70107A/pt unknown
- 1979-08-23 AT AT0568379A patent/AT373591B/de not_active IP Right Cessation
- 1979-08-23 JP JP10764779A patent/JPS5533484A/ja active Pending
- 1979-08-23 YU YU2073/79A patent/YU40849B/xx unknown
- 1979-08-23 BE BE0/196852A patent/BE878395A/fr not_active IP Right Cessation
- 1979-08-23 FI FI792632A patent/FI68818C/fi not_active IP Right Cessation
- 1979-08-23 IL IL58096A patent/IL58096A/xx not_active IP Right Cessation
- 1979-08-23 SU SU792804596A patent/SU797576A3/ru active
- 1979-08-23 AR AR277829A patent/AR222494A1/es active
- 1979-08-23 DE DE19792934166 patent/DE2934166A1/de not_active Ceased
- 1979-08-24 SE SE7907067A patent/SE446865B/sv not_active IP Right Cessation
- 1979-08-24 CS CS795769A patent/CS208131B2/cs unknown
- 1979-08-24 NL NL7906408A patent/NL7906408A/nl not_active Application Discontinuation
- 1979-08-24 CH CH773579A patent/CH643548A5/fr not_active IP Right Cessation
- 1979-08-27 EG EG520/79A patent/EG14355A/xx active

Also Published As

Publication number	Publication date
CS208131B2 (en)	1981-08-31
GR69619B (cs)	1982-07-06
GB2031410A (en)	1980-04-23
RO78156A (ro)	1982-02-01
FI68818C (fi)	1985-11-11
FI792632A7 (fi)	1980-02-26
BE878395A (fr)	1980-02-25
FR2434158A1 (fr)	1980-03-21
NL7906408A (nl)	1980-02-27
EG14355A (en)	1983-12-31
JPS5533484A (en)	1980-03-08
IL58096A0 (en)	1979-12-30
CH643548A5 (fr)	1984-06-15
SE446865B (sv)	1986-10-13
PL116771B1 (en)	1981-06-30
FR2434158B1 (cs)	1985-05-03
PT70107A (fr)	1979-09-01
SU797576A3 (ru)	1981-01-15
DE2934166A1 (de)	1980-02-28
HU182916B (en)	1984-03-28
SE7907067L (sv)	1980-02-26
IL58096A (en)	1982-12-31
PL217893A1 (cs)	1980-04-21
ATA568379A (de)	1983-06-15
ES481856A1 (es)	1980-02-16
CA1128511A (fr)	1982-07-27
YU207379A (en)	1983-02-28
FI68818B (fi)	1985-07-31
YU40849B (en)	1986-06-30
AT373591B (de)	1984-02-10
GB2031410B (en)	1982-12-01
BG30929A3 (bg)	1981-09-15
AR222494A1 (es)	1981-05-29

Legal Events

Date	Code	Title	Description
1999-03-18	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
CH635823A5 (de)	1983-04-29	Verfahren zur herstellung von neuen 1-amidin-3-substituierten-phenylharnstoffen.
DE2237592C2 (de)	1985-08-14	6-(o-Chlorphenyl)-8-chlor-4H-imidazo-[1,2-a] [1,4]-benzodiazepine und Verfahren zu ihrer Herstellung
DE2720545C3 (de)	1980-09-11	Derivate des 2,4-Diamino-6,7-dimethoxychinazolins, ihre Herstellung und pharmazeutische Mittel
EP0761650A1 (de)	1997-03-12	Thermostabile und lagerfähige Kristallmodifikation von N-Methyl-N-((1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidin-1-yl)-ethyl)-2,2-diphenyl-acetamid und Verfahren zu dessen Herstellung
DD145534A5 (de)	1980-12-17	Verfahren zur herstellung von 1,3-benzoxazin-2,4-dion-derivaten
DE2815088A1 (de)	1978-10-19	5-piperazinylsubstituierte derivate von pyrido- eckige klammer auf 2.3-b eckige klammer zu -benzothiazepin(1.5), ihre herstellung und pharmazeutische mittel
DE2818351A1 (de)	1978-11-09	Benzoesaeurederivate, verfahren zu ihrer herstellung und ihre therapeutische verwendung
DE2307536C3 (de)	1980-03-06	2-Methylamino-4-(4-methylpiperazino)-5-methylthio-6-chlorpyrünidin, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel
DE2442124A1 (de)	1975-03-06	Butyramid-derivate, verfahren zu deren herstellung und diese substanzen enthaltende arzneimittel
DE3113087C2 (de)	1984-06-14	1,4-Disubstituierte Piperazine, deren Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2727629C2 (de)	1986-09-25	1-p-Chlorbenzoyl-5-methoxy-2-methyl- 3-indolyl-essigsäure-2'-phenyl-2'-carbonsäureäthylester, Verfahren zu seiner Herstellung und pharmazeutische Mittel
DE2609397A1 (de)	1976-09-23	8-aminotheophyllinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen
DE2323744C3 (de)	1978-11-23	4,4'-Bismethylen-(3-methoxy-2-naphthoesäure-triamcinolon-acetonidester) und Verfahren zu dessen Herstellung
DD145266A5 (de)	1980-12-03	Verfahren zur herstellung von 6-methoxy-2-acetylnaphthalinoxim-derivaten
DE2351657A1 (de)	1974-04-25	3,4,5-trimethoxy-acetophenonoximcarbamate, verfahren zu ihrer herstellung und ihre verwendung in einer arzneimittelzubereitung
DE2835043A1 (de)	1979-12-06	Bromhexin-derivate mit gegenueber bromhexin geringerer schleimloesender und hustenlindernder wirkung und geringerer toxizitaet
DE2251872C3 (de)	1978-05-03	Salze des N- [(5-Carboxy-methoxy-2-phenyl-ybenzopyron-7-yl)-oxyacetyl] -tetrahydropapaverins, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2520483A1 (de)	1975-11-27	Phenoxy-isobuttersaeurederivate und diese verbindungen enthaltende arzneimittel
DD202028A5 (de)	1983-08-24	Verfahren zur herstellung von 17,18-dehydroapovincamino-3',4',5'-trimethoxybenzoat
DE2428201A1 (de)	1975-01-09	Anthranilsaeurederivate, verfahren zu deren herstellung und diese derivate enthaltende arzneimittel
DE2166662B2 (de)	1978-07-13	Dibenzothiazepinderivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
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