CA1128511A - Derives de 1,3-benzoxazine-2,4-dione, leur preparation et leur application en tant que medicaments - Google Patents

Derives de 1,3-benzoxazine-2,4-dione, leur preparation et leur application en tant que medicaments

Info

Publication number: CA1128511A
Authority: CA; Canada
Prior art keywords: dione; benzoxazine; chloro; preparation; recovered
Prior art date: 1978-08-25
Legal status (The legal status 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 status listed.): Expired

Application number

CA334,287A

Other languages

English (en)

French (fr)

Inventor

Antonio Esteve-Subirana

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Provesan SA

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

1979-08-22

Publication date

1982-07-27

1979-08-22 Application filed by Provesan SA filed Critical Provesan SA

1982-07-27 Application granted granted Critical

1982-07-27 Publication of CA1128511A publication Critical patent/CA1128511A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 23
OAYRYNVEFFWSHK-UHFFFAOYSA-N carsalam Chemical class C1=CC=C2OC(=O)NC(=O)C2=C1 OAYRYNVEFFWSHK-UHFFFAOYSA-N 0.000 title claims abstract 5
229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
-1 alkyl radical Chemical class 0.000 claims abstract description 7
239000000460 chlorine Substances 0.000 claims abstract description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 9
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 5
239000002253 acid Substances 0.000 claims description 5
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 3
GMFBXDUNANTIIL-UHFFFAOYSA-N 5-chloro-2-hydroxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC(Cl)=CC=C1O GMFBXDUNANTIIL-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
150000003872 salicylic acid derivatives Chemical class 0.000 claims description 2
238000000034 method Methods 0.000 claims 23
238000001311 chemical methods and process Methods 0.000 claims 8
NKBASRXWGAGQDP-UHFFFAOYSA-N 5-chlorosalicylic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1O NKBASRXWGAGQDP-UHFFFAOYSA-N 0.000 claims 6
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 claims 3
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 3
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 claims 3
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 3
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 claims 3
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 claims 2
125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims 2
OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 claims 1
UIADMYLYGJYUSQ-UHFFFAOYSA-N 2-(isocyanatomethyl)furan Chemical compound O=C=NCC1=CC=CO1 UIADMYLYGJYUSQ-UHFFFAOYSA-N 0.000 claims 1
WACBJMRDDSHLDH-UHFFFAOYSA-N 2-bromooxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OBr WACBJMRDDSHLDH-UHFFFAOYSA-N 0.000 claims 1
MKSBQICYLQNQLP-UHFFFAOYSA-N 5-bromo-2-hydroxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC(Br)=CC=C1O MKSBQICYLQNQLP-UHFFFAOYSA-N 0.000 claims 1
YHNCXEIAPYBIBR-UHFFFAOYSA-N 5-chloro-2-hydroxy-n-propylbenzamide Chemical compound CCCNC(=O)C1=CC(Cl)=CC=C1O YHNCXEIAPYBIBR-UHFFFAOYSA-N 0.000 claims 1
BVZXRECCTPCIJU-UHFFFAOYSA-N 5-chloro-n-ethyl-2-hydroxybenzamide Chemical compound CCNC(=O)C1=CC(Cl)=CC=C1O BVZXRECCTPCIJU-UHFFFAOYSA-N 0.000 claims 1
150000001768 cations Chemical class 0.000 claims 1
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 6
239000001257 hydrogen Substances 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
150000002431 hydrogen Chemical class 0.000 abstract description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
239000000730 antalgic agent Substances 0.000 abstract 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
229910052794 bromium Inorganic materials 0.000 abstract 1
229940079593 drug Drugs 0.000 abstract 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
230000000202 analgesic effect Effects 0.000 description 8
239000000047 product Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
208000002193 Pain Diseases 0.000 description 5
239000000243 solution Substances 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
229960004373 acetylcholine Drugs 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000829 suppository Substances 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
229920003084 Avicel® PH-102 Polymers 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
241000257303 Hymenoptera Species 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
206010037660 Pyrexia Diseases 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
231100000460 acute oral toxicity Toxicity 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000002221 antipyretic Substances 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
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003937 drug carrier Substances 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
230000002757 inflammatory effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [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
239000013588 oral product Substances 0.000 description 1
229940023486 oral product Drugs 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
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)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Rheumatology (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)

CA334,287A 1978-08-25 1979-08-22 Derives de 1,3-benzoxazine-2,4-dione, leur preparation et leur application en tant que medicaments Expired CA1128511A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7824674		1978-08-25
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
CA1128511A true CA1128511A (fr)	1982-07-27

Family

ID=9212085

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA334,287A Expired CA1128511A (fr)	1978-08-25	1979-08-22	Derives de 1,3-benzoxazine-2,4-dione, leur preparation et leur application en tant que medicaments

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
JP4224566B2 (ja)	2000-12-18	2009-02-18	株式会社医薬分子設計研究所	炎症性サイトカイン産生遊離抑制剤
EA009701B1 (ru)	2002-06-06	2008-02-28	Инститьют Оф Медисинал Молекьюлар Дизайн. Инк.	Противоаллергические средства
CA2488363C (en)	2002-06-06	2011-01-04	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 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 BG BG044725A patent/BG30929A3/xx unknown
- 1979-08-22 GR GR52886A patent/GR69619B/el unknown
- 1979-08-22 RO RO7998518A patent/RO78156A/ro unknown
- 1979-08-22 HU HU79PO694A patent/HU182916B/hu not_active IP Right Cessation
- 1979-08-23 YU YU2073/79A patent/YU40849B/xx unknown
- 1979-08-23 AR AR277829A patent/AR222494A1/es active
- 1979-08-23 JP JP10764779A patent/JPS5533484A/ja active Pending
- 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 DE DE19792934166 patent/DE2934166A1/de not_active Ceased
- 1979-08-23 AT AT0568379A patent/AT373591B/de not_active IP Right Cessation
- 1979-08-23 BE BE0/196852A patent/BE878395A/fr not_active IP Right Cessation
- 1979-08-23 PT PT70107A patent/PT70107A/pt unknown
- 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
- 1979-08-24 SE SE7907067A patent/SE446865B/sv not_active IP Right Cessation
- 1979-08-27 EG EG520/79A patent/EG14355A/xx active

Also Published As

Publication number	Publication date
BE878395A (fr)	1980-02-25
YU207379A (en)	1983-02-28
FR2434158A1 (fr)	1980-03-21
FI68818B (fi)	1985-07-31
CS208131B2 (en)	1981-08-31
FR2434158B1 (cs)	1985-05-03
ES481856A1 (es)	1980-02-16
AR222494A1 (es)	1981-05-29
NL7906408A (nl)	1980-02-27
EG14355A (en)	1983-12-31
RO78156A (ro)	1982-02-01
YU40849B (en)	1986-06-30
AT373591B (de)	1984-02-10
BG30929A3 (bg)	1981-09-15
DD145534A5 (de)	1980-12-17
CH643548A5 (fr)	1984-06-15
FI68818C (fi)	1985-11-11
IL58096A0 (en)	1979-12-30
PT70107A (fr)	1979-09-01
GB2031410A (en)	1980-04-23
PL217893A1 (cs)	1980-04-21
SU797576A3 (ru)	1981-01-15
ATA568379A (de)	1983-06-15
PL116771B1 (en)	1981-06-30
HU182916B (en)	1984-03-28
IL58096A (en)	1982-12-31
GB2031410B (en)	1982-12-01
DE2934166A1 (de)	1980-02-28
GR69619B (cs)	1982-07-06
JPS5533484A (en)	1980-03-08
FI792632A7 (fi)	1980-02-26
SE7907067L (sv)	1980-02-26
SE446865B (sv)	1986-10-13

Legal Events

Date	Code	Title	Description
1999-07-27	MKEX	Expiry

Publication	Publication Date	Title
JP3231042B2 (ja)	2001-11-19	２−（２，６−ジ−ハロ−フェニルアミノ）フェニル酢酸の誘導体の硝酸エステルおよびその製造法
HU178015B (en)	1982-02-28	Process for preparing new 5-methyl-isoxazola-4-carboxylic acid-/4-trifluoromethyl/-anilide
PL175265B1 (pl)	1998-12-31	Nowa pochodna arylopropionowa sól trometaminowa kwasu (+)-S-2-(3-benzoilofenylo)propionowego, sposób jej wytwarzania i kompozycja farmaceutyczna
JPH10245337A (ja)	1998-09-14	薬学的組成物
HU189586B (en)	1986-07-28	Process for preparing crystalline salts of benzothiazine-dioxide
CN111635309B (zh)	2024-03-12	一种新型解热镇痛药物及其制备方法和用途
CN111635315B (zh)	2024-03-12	一种解热镇痛药物及其制备方法和用途
CS267551B1 (en)	1990-02-12	Pharmaceutical agents for asthma treatment and method of effective substance production
CA1128511A (fr)	1982-07-27	Derives de 1,3-benzoxazine-2,4-dione, leur preparation et leur application en tant que medicaments
HU203766B (en)	1991-09-30	Process for producing estramustine-esters and pharmaceutical compositions containing them as active components
EP0068998A1 (fr)	1983-01-05	Aryl-1 aminométhyl-2 cyclopropanes carboxylates (Z), leur préparation et leur application en tant que médicaments utiles dans le traitement d'algies diverses
EP0177356B1 (en)	1991-09-18	Method for treatment of antidiuresis
CH631157A5 (fr)	1982-07-30	Derives d'acide benzoique, leur procede de preparation et leur application therapeutique.
EP0080010B1 (en)	1985-08-07	Novel compounds with antiinflammatory and analgesic activity, process for the preparation thereof and pharmaceutical compositions therefrom
CA1128519A (fr)	1982-07-27	Derives de 6-methoxy-2-acetylnaphtalene oxime, leur preparation et leur application en tant que medicaments
EP0063084A1 (fr)	1982-10-20	Dérivés de phénéthanolamine, leur préparation et leur application en thérapeutique
WO1979000231A1 (fr)	1979-05-03	Nouveaux derives de la thiazoline et leur application comme medicaments
US8754129B2 (en)	2014-06-17	Crystalline vorinostat form VI
EP0022737B1 (fr)	1982-06-09	Imines dérivées de l'amino-5 benzodioxole-1,3 utiles comme médicaments et leur préparation
WO1995004058A1 (fr)	1995-02-09	Sel de codeine de l'acide 2-(3-benzoylphenyl)propionique, procede d'obtention et compositions pharmaceutiques le contenant
EP0010030B1 (fr)	1982-05-05	Nouveaux dérivés d'ortho chloro benzoyl-2 chloro-4 glycylanilide, leur préparation et leur application en tant que médicaments
JPH0327367A (ja)	1991-02-05	新規な２―アミノ―５―アリールオキシメチルオキサゾリンとその塩
HU189866B (en)	1986-08-28	Process for producing new acylamino-phenyl-esters of thiazolidine-carboxylic acid
US4333938A (en)	1982-06-08	Imino derivatives of 5-aminobenzodioxole-1,3 which are useful as medicaments
US4440786A (en)	1984-04-03	Compounds with antiinflammatory and analgesic activity, process for the preparation thereof and pharmaceutical compositio ns therefrom