CH643548A5 - Derives de 1,3-benzoxazine-2,4-dione, leur preparation et medicaments les contenant. - Google Patents

Derives de 1,3-benzoxazine-2,4-dione, leur preparation et medicaments les contenant. Download PDF

Info

Publication number: CH643548A5
Authority: CH; Switzerland
Prior art keywords: benzoxazine; dione; formula; chloro; derivatives
Prior art date: 1978-08-25

Application number

CH773579A

Other languages

English (en)

French (fr)

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

1979-08-24

Publication date

1984-06-15

1979-08-24 Application filed by Provesan Sa filed Critical Provesan Sa

1984-06-15 Publication of CH643548A5 publication Critical patent/CH643548A5/fr

Links

238000002360 preparation method Methods 0.000 title claims description 7
239000003814 drug Substances 0.000 title claims description 5
OAYRYNVEFFWSHK-UHFFFAOYSA-N carsalam Chemical class C1=CC=C2OC(=O)NC(=O)C2=C1 OAYRYNVEFFWSHK-UHFFFAOYSA-N 0.000 title claims description 4
239000000460 chlorine Substances 0.000 claims description 16
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 claims description 6
-1 alkyl radical Chemical class 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
HKZCOWRJCWNNFP-UHFFFAOYSA-N 6-chloro-3-(furan-2-ylmethyl)-1,3-benzoxazine-2,4-dione Chemical compound O=C1C2=CC(Cl)=CC=C2OC(=O)N1CC1=CC=CO1 HKZCOWRJCWNNFP-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical class NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 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
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 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
FNXRPOPDYIZQHW-UHFFFAOYSA-N 6-chloro-3-(2-phenoxyphenyl)-1,3-benzoxazine-2,4-dione Chemical compound O=C1C2=CC(Cl)=CC=C2OC(=O)N1C1=CC=CC=C1OC1=CC=CC=C1 FNXRPOPDYIZQHW-UHFFFAOYSA-N 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
238000000034 method Methods 0.000 claims 1
230000000202 analgesic effect Effects 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 5
230000003110 anti-inflammatory effect 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
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
208000002193 Pain Diseases 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
JNZZLCUTRFPQPJ-UHFFFAOYSA-N 6-bromo-3-methyl-1,3-benzoxazine-2,4-dione Chemical compound C1=C(Br)C=C2C(=O)N(C)C(=O)OC2=C1 JNZZLCUTRFPQPJ-UHFFFAOYSA-N 0.000 description 2
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
231100000111 LD50 Toxicity 0.000 description 2
241001465754 Metazoa 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
235000019359 magnesium stearate Nutrition 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000829 suppository Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
IEJOONSLOGAXNO-UHFFFAOYSA-N 5-bromo-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(Br)=CC=C1O IEJOONSLOGAXNO-UHFFFAOYSA-N 0.000 description 1
GOMXAFKCHRQJPQ-UHFFFAOYSA-N 6-chloro-3-(2-thiophen-2-yloxyphenyl)-1,3-benzoxazine-2,4-dione Chemical compound ClC=1C=CC2=C(C(N(C(O2)=O)C2=C(C=CC=C2)OC=2SC=CC=2)=O)C=1 GOMXAFKCHRQJPQ-UHFFFAOYSA-N 0.000 description 1
RUSRJCQXSADYBI-UHFFFAOYSA-N 6-chloro-3-ethyl-1,3-benzoxazine-2,4-dione Chemical compound C1=C(Cl)C=C2C(=O)N(CC)C(=O)OC2=C1 RUSRJCQXSADYBI-UHFFFAOYSA-N 0.000 description 1
OAJNFZRAWNMFEC-UHFFFAOYSA-N 6-chloro-3-propyl-1,3-benzoxazine-2,4-dione Chemical compound C1=C(Cl)C=C2C(=O)N(CCC)C(=O)OC2=C1 OAJNFZRAWNMFEC-UHFFFAOYSA-N 0.000 description 1
208000005171 Dysmenorrhea Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010019233 Headaches 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
241001539019 Monolene Species 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
229920003110 Primojel Polymers 0.000 description 1
206010037660 Pyrexia Diseases 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
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 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
150000007513 acids Chemical class 0.000 description 1
231100000460 acute oral toxicity Toxicity 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000007059 acute toxicity Effects 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
230000001754 anti-pyretic effect Effects 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
229940125716 antipyretic agent Drugs 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
229940113118 carrageenan Drugs 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
230000004927 fusion Effects 0.000 description 1
229950005514 glycyclamide Drugs 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
208000015181 infectious disease 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
229940057952 methanol Drugs 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
201000003068 rheumatic fever Diseases 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
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
208000004371 toothache Diseases 0.000 description 1
238000005303 weighing Methods 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 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)

CH773579A 1978-08-25 1979-08-24 Derives de 1,3-benzoxazine-2,4-dione, leur preparation et medicaments les contenant. CH643548A5 (fr)

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
CH643548A5 true CH643548A5 (fr)	1984-06-15

Family

ID=9212085

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH773579A CH643548A5 (fr)	1978-08-25	1979-08-24	Derives de 1,3-benzoxazine-2,4-dione, leur preparation et medicaments les contenant.

Country Status (25)

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

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2002049632A1 (en)	2000-12-18	2002-06-27	Institute Of Medicinal Molecular Design. Inc.	Inhibitors against the production and release of inflammatory cytokines
US7626042B2 (en)	2002-06-06	2009-12-01	Institute Of Medicinal Molecular Design, Inc.	O-substituted hydroxyaryl derivatives
AU2003242103A1 (en)	2002-06-06	2003-12-22	Institute Of Medicinal Molecular Design, Inc	Antiallergic agents
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 CA CA334,287A patent/CA1128511A/fr not_active Expired
- 1979-08-22 BG BG044725A patent/BG30929A3/xx unknown
- 1979-08-22 PL PL1979217893A patent/PL116771B1/pl unknown
- 1979-08-22 GB GB7929266A patent/GB2031410B/en not_active Expired
- 1979-08-22 RO RO7998518A patent/RO78156A/ro unknown
- 1979-08-22 GR GR52886A patent/GR69619B/el unknown
- 1979-08-22 HU HU79PO694A patent/HU182916B/hu not_active IP Right Cessation
- 1979-08-23 JP JP10764779A patent/JPS5533484A/ja active Pending
- 1979-08-23 AT AT0568379A patent/AT373591B/de not_active IP Right Cessation
- 1979-08-23 AR AR277829A patent/AR222494A1/es active
- 1979-08-23 PT PT70107A patent/PT70107A/pt unknown
- 1979-08-23 FI FI792632A patent/FI68818C/fi not_active IP Right Cessation
- 1979-08-23 DE DE19792934166 patent/DE2934166A1/de not_active Ceased
- 1979-08-23 BE BE0/196852A patent/BE878395A/fr not_active IP Right Cessation
- 1979-08-23 YU YU2073/79A patent/YU40849B/xx unknown
- 1979-08-23 IL IL58096A patent/IL58096A/xx not_active IP Right Cessation
- 1979-08-23 SU SU792804596A patent/SU797576A3/ru active
- 1979-08-24 SE SE7907067A patent/SE446865B/sv not_active IP Right Cessation
- 1979-08-24 CH CH773579A patent/CH643548A5/fr not_active IP Right Cessation
- 1979-08-24 NL NL7906408A patent/NL7906408A/nl not_active Application Discontinuation
- 1979-08-24 CS CS795769A patent/CS208131B2/cs unknown
- 1979-08-27 EG EG520/79A patent/EG14355A/xx active

Also Published As

Publication number	Publication date
SE7907067L (sv)	1980-02-26
DD145534A5 (de)	1980-12-17
YU40849B (en)	1986-06-30
SE446865B (sv)	1986-10-13
PL116771B1 (en)	1981-06-30
NL7906408A (nl)	1980-02-27
GR69619B (de)	1982-07-06
CA1128511A (fr)	1982-07-27
FI792632A7 (fi)	1980-02-26
SU797576A3 (ru)	1981-01-15
JPS5533484A (en)	1980-03-08
FI68818C (fi)	1985-11-11
AT373591B (de)	1984-02-10
PL217893A1 (de)	1980-04-21
DE2934166A1 (de)	1980-02-28
GB2031410B (en)	1982-12-01
ES481856A1 (es)	1980-02-16
RO78156A (ro)	1982-02-01
BG30929A3 (bg)	1981-09-15
FR2434158A1 (fr)	1980-03-21
FR2434158B1 (de)	1985-05-03
YU207379A (en)	1983-02-28
EG14355A (en)	1983-12-31
BE878395A (fr)	1980-02-25
IL58096A (en)	1982-12-31
CS208131B2 (en)	1981-08-31
PT70107A (fr)	1979-09-01
ATA568379A (de)	1983-06-15
HU182916B (en)	1984-03-28
FI68818B (fi)	1985-07-31
AR222494A1 (es)	1981-05-29
IL58096A0 (en)	1979-12-30
GB2031410A (en)	1980-04-23

Legal Events

Date	Code	Title	Description
1995-04-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CA1167047A (fr)	1984-05-08	Benzodioxanne l,4 methoxy-2 propanolamines, leur preparation et leur application en tant que medicaments
EP0000299B1 (de)	1980-11-12	Neue substituierte 2-Benzoyl-4-chloro-glycinanilidederivate, Verfahren zu ihrer Herstellung und deren Verwendung als Heilmittel.
EP0068998B1 (de)	1985-08-28	(Z)-1-Aryl-2-aminomethyl-cyclopropan-carboxylate, ihre Herstellung und ihre Verwendung als Arzneimittel für die Behandlung von verschiedenen Schmerzen
FR2595695A1 (fr)	1987-09-18	Derives de n-(((hydroxy-2 phenyl) (phenyl) methylene) amino-2) ethyl) acetamide, leur preparation et leur application en therapeutique
EP0007824A1 (de)	1980-02-06	Benzofuranderivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel.
EP0077720B1 (de)	1984-07-25	Derivate von Biphenyl-Alkyl-Carboxylaten, deren Herstellungsverfahren und deren Verwendung als Arzneimittel
CH631157A5 (fr)	1982-07-30	Derives d'acide benzoique, leur procede de preparation et leur application therapeutique.
EP0015214A1 (de)	1980-09-03	Substituierte 2-(Benzoyl)-glycinanilid-Derivate, ihre Herstellung und ihre Verwendung in anxiolytischen Arzneimitteln
CA1091233A (fr)	1980-12-09	Procede de preparation de nouveaux indoles substitues
EP0143016B1 (de)	1987-07-29	Derivate von 4-(3-Alkynyloxy-2-hydroxy-propyl)-piperazin-1-yl-N-phenylacetamid, ihre Herstellung und ihre therapeutische Verwendung
EP0087337B1 (de)	1986-04-16	2-Piperazinyl-4-phenyl-quinazolin-Derivate mit antidepressiven Eigenschaften, Verfahren zu deren Herstellung und diese enthaltende Arzneimitteln
CA1128511A (fr)	1982-07-27	Derives de 1,3-benzoxazine-2,4-dione, leur preparation et leur application en tant que medicaments
EP0063084A1 (de)	1982-10-20	Phenethanolamin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0022017B1 (de)	1982-05-05	Derivate von 2-Benzoyl-4-nitro-aniliden, deren Herstellung und deren Verwendung als Heilmittel
CH641773A5 (fr)	1984-03-15	Derives de 6-methoxy-2-acetylnaphtalene oxime, procede de leur preparation et medicament comportant de ces derives.
EP0176444B1 (de)	1989-02-22	Verfahren zur Herstellung von 4H-1,2,4-Triazol-Derivaten, so erhaltene neue Triazole, ihre Verwendung als Arzneimittel und sie enthaltende pharmazeutische Zusammensetzungen
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CH623046A5 (de)	1981-05-15
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