LU81891A1 - Derives d'amino-3 dioxo-2,4(1h,3h)quinazolines,leur procede de preparation et composition therapeutique les contenant - Google Patents

Derives d'amino-3 dioxo-2,4(1h,3h)quinazolines,leur procede de preparation et composition therapeutique les contenant Download PDF

Info

Publication number: LU81891A1
Authority: LU; Luxembourg
Prior art keywords: dioxo; quinazoline; chloro; sulfonamido; dimethylamino
Prior art date: 1978-11-27

Application number

LU81891A

Other languages

English (en)

French (fr)

Inventor

R Baronnet

R Callendret

Original Assignee

Berri Balzac

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.)

1978-11-27

Filing date

1979-11-15

Publication date

1980-01-25

1979-11-15 Application filed by Berri Balzac filed Critical Berri Balzac

1980-01-25 Publication of LU81891A1 publication Critical patent/LU81891A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 32
239000000203 mixture Substances 0.000 title claims description 16
238000000034 method Methods 0.000 title claims description 14
230000001225 therapeutic effect Effects 0.000 title claims description 7
150000003246 quinazolines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 22
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 19
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 13
230000001882 diuretic effect Effects 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
229910021529 ammonia Inorganic materials 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
HCRKCZRJWPKOAR-SNVBAGLBSA-N (4s)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide Chemical compound CCN[C@@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2 HCRKCZRJWPKOAR-SNVBAGLBSA-N 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
238000007911 parenteral administration Methods 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000000047 product Substances 0.000 description 16
239000000243 solution Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 11
238000001816 cooling Methods 0.000 description 9
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 8
208000004880 Polyuria Diseases 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
230000035619 diuresis Effects 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 5
229960003883 furosemide Drugs 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
229940124530 sulfonamide Drugs 0.000 description 4
150000003456 sulfonamides Chemical class 0.000 description 4
210000002700 urine Anatomy 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
238000010926 purge Methods 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
230000000054 salidiuretic effect Effects 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
GRWMSCBKWMQPON-UHFFFAOYSA-N 2-aminobenzohydrazide Chemical class NNC(=O)C1=CC=CC=C1N GRWMSCBKWMQPON-UHFFFAOYSA-N 0.000 description 2
DDXYEAZJCJNNCV-UHFFFAOYSA-N 3-(dimethylamino)-1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)N(N(C)C)C(=O)NC2=C1 DDXYEAZJCJNNCV-UHFFFAOYSA-N 0.000 description 2
NMGODFWGUBLTTA-UHFFFAOYSA-N 3-amino-1h-quinazoline-2,4-dione Chemical class C1=CC=C2C(=O)N(N)C(=O)NC2=C1 NMGODFWGUBLTTA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000002934 diuretic Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 description 1
HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 1
MEVGKQYFICKFKY-UHFFFAOYSA-N 7-chloro-3-(dimethylamino)-1h-quinazoline-2,4-dione Chemical compound ClC1=CC=C2C(=O)N(N(C)C)C(=O)NC2=C1 MEVGKQYFICKFKY-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
241000551547 Dione <red algae> Species 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
101000713585 Homo sapiens Tubulin beta-4A chain Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
244000062793 Sorghum vulgare Species 0.000 description 1
102100036788 Tubulin beta-4A chain Human genes 0.000 description 1
GCXUHGZBBGZTII-UHFFFAOYSA-N a828071 Chemical compound ClC(Cl)=O.ClC(Cl)=O GCXUHGZBBGZTII-UHFFFAOYSA-N 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
230000004075 alteration Effects 0.000 description 1
239000003708 ampul Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical compound C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
229960002003 hydrochlorothiazide Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
NZURLGBNVJOLKZ-UHFFFAOYSA-N n-morpholin-4-ylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NN1CCOCC1 NZURLGBNVJOLKZ-UHFFFAOYSA-N 0.000 description 1
ITNXJLXLFAFOHO-UHFFFAOYSA-N n-piperidin-1-ylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NN1CCCCC1 ITNXJLXLFAFOHO-UHFFFAOYSA-N 0.000 description 1
210000000885 nephron Anatomy 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
-1 sulfonamido- Chemical class 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
230000036325 urinary excretion Effects 0.000 description 1
238000005303 weighing Methods 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Hematology (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

LU81891A 1978-11-27 1979-11-15 Derives d'amino-3 dioxo-2,4(1h,3h)quinazolines,leur procede de preparation et composition therapeutique les contenant LU81891A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7833438		1978-11-27
FR7833438A FR2442231A1 (fr)	1978-11-27	1978-11-27	Derives d'amino-3 dioxo-2,4 (1h,3h) quinazolines, leur procede de preparation et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
LU81891A1 true LU81891A1 (fr)	1980-01-25

Family

ID=9215392

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU81891A LU81891A1 (fr)	1978-11-27	1979-11-15	Derives d'amino-3 dioxo-2,4(1h,3h)quinazolines,leur procede de preparation et composition therapeutique les contenant

Country Status (15)

Country	Link
EP (1)	EP0012051A1 (da)
JP (1)	JPS55108859A (da)
AU (1)	AU5299479A (da)
BE (1)	BE880246A (da)
DK (1)	DK492979A (da)
ES (1)	ES485973A1 (da)
FR (1)	FR2442231A1 (da)
GB (1)	GB2042509A (da)
GR (1)	GR74084B (da)
IL (1)	IL58725A0 (da)
IT (1)	IT7969276A0 (da)
LU (1)	LU81891A1 (da)
NO (1)	NO793809L (da)
PT (1)	PT70488A (da)
ZA (1)	ZA796236B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3068648D1 (de) *	1980-03-10	1984-08-30	Berri Balzac	Derivatives of 3-amino-(1h,3h)-2,4-quinazolin-diones
CA2193932C (en) *	1995-12-26	2001-08-21	Shinji Nishii	Process for producing isatoic anhydrides

1978
- 1978-11-27 FR FR7833438A patent/FR2442231A1/fr active Granted
1979
- 1979-11-08 GR GR60454A patent/GR74084B/el unknown
- 1979-11-09 EP EP79400838A patent/EP0012051A1/fr not_active Withdrawn
- 1979-11-14 IL IL58725A patent/IL58725A0/xx unknown
- 1979-11-15 GB GB7939565A patent/GB2042509A/en not_active Withdrawn
- 1979-11-15 ES ES485973A patent/ES485973A1/es not_active Expired
- 1979-11-15 LU LU81891A patent/LU81891A1/fr unknown
- 1979-11-19 ZA ZA00796236A patent/ZA796236B/xx unknown
- 1979-11-20 AU AU52994/79A patent/AU5299479A/en not_active Abandoned
- 1979-11-20 DK DK492979A patent/DK492979A/da unknown
- 1979-11-22 JP JP15077379A patent/JPS55108859A/ja active Pending
- 1979-11-23 PT PT70488A patent/PT70488A/pt unknown
- 1979-11-23 NO NO793809A patent/NO793809L/no unknown
- 1979-11-26 IT IT7969276A patent/IT7969276A0/it unknown
- 1979-11-26 BE BE0/198274A patent/BE880246A/fr unknown

Also Published As

Publication number	Publication date
JPS55108859A (en)	1980-08-21
EP0012051A1 (fr)	1980-06-11
BE880246A (fr)	1980-05-27
DK492979A (da)	1980-05-28
AU5299479A (en)	1980-05-29
GB2042509A (en)	1980-09-24
FR2442231A1 (fr)	1980-06-20
NO793809L (no)	1980-05-28
FR2442231B1 (da)	1981-07-10
ES485973A1 (es)	1980-05-16
IL58725A0 (en)	1980-02-29
IT7969276A0 (it)	1979-11-26
ZA796236B (en)	1980-11-26
PT70488A (fr)	1979-12-01
GR74084B (da)	1984-06-06

Publication	Publication Date	Title
EP0465323A1 (fr)	1992-01-08	Dérivés de pyrimidine antagonistes des récepteurs à l'angiotensine II, leurs procédés de préparation et compositions pharmaceutiques les contenant
FR2554719A1 (fr)	1985-05-17	Medicaments a base de nouveaux derives de la vinyl-6 furo-(3,4-c)-pyridine
EP0217700A1 (fr)	1987-04-08	Derives de benzimidazole, leur preparation et leur application en therapeutique
EP0015038A1 (fr)	1980-09-03	Composition pharmaceutique comprenant un dérivé de diphénylhydantoine, dérivés mis en oeuvre et leur préparation
EP0092458A2 (fr)	1983-10-26	Dérives d'imidazo(1,2-a)pyridine, leur préparation et leur application en thérapeutique
EP0073161B1 (fr)	1986-10-22	Nouveaux dérivés de la pyrazine actifs sur le système nerveux central
CH639369A5 (fr)	1983-11-15	Benzamides heterocycliques substitues et leurs procedes de preparation.
EP0162776B1 (fr)	1989-04-19	Dérivés hétérocycliques, leurs procédés de préparation,médicaments les contenant, utiles notamment comme inhibiteurs de l'aldose réductase
MC1478A1 (fr)	1983-06-17	Nouveaux derives de l'imidazoquinazoline
CH628898A5 (fr)	1982-03-31	Procede de preparation d'aza-8 purinones-6.
CH407088A (fr)	1966-02-15	Procédé de préparation de dérivés des acides 4-halo-3-sulfamoyl-benzoïques
EP0000452B1 (fr)	1981-05-06	Dérivés d'oxadiazole-1,2,4, leur préparation et leur application en thérapeutique.
EP0079810A1 (fr)	1983-05-25	Nouveaux dérivés de la phényl-4 quinazoline actifs sur le système nerveux central
MC1017A1 (fr)	1975-02-28	Procédé de préparation de dérivés de l'indole
EP0094283B1 (fr)	1985-11-21	Forme médicamenteuse de théophylline à action prolongée
EP0008259A1 (fr)	1980-02-20	Nouveaux dérivés de la pipéridylbenzimidazolinone, leurs procédés de préparation et les compositions pharmaceutiques les renfermant
EP0183577B1 (fr)	1990-02-07	Dérivés du thiadiazole actifs sur le système nerveux central, procédé d'obtension et compositions pharmaceutiques les contenant
EP0176444B1 (fr)	1989-02-22	Nouveau procédé de préparation de dérivés du 4 H-1,2-4-triazole, nouveaux triazoles ainsi obtenus, leur applicication comme médicaments et les compositions pharmaceutiques les renfermant
FR2525221A1 (fr)	1983-10-21	Derives du furanne et sels d'addition de ces derives, leurs procedes de preparation et leurs applications en therapeutique
CA1209142A (fr)	1986-08-05	Procede d'obtention de nouvelles cyanoguanidines et des compositions pharmaceutiques en renfermant
EP0012051A1 (fr)	1980-06-11	Dérivés d'amino-3 dioxo-2,4 (1H,3H) quinazolines, leur procédé de préparation et composition thérapeutique les contenant
EP0035619B1 (fr)	1984-07-25	Dérivés d'amino-3 (1H,3H) quinazolinedione-2,4
CA1068270A (fr)	1979-12-18	Diamino-2,4-bromo-5 chloro-6 pyrimidines utilisables comme medicaments et procede pour leur preparation
CH658786A5 (fr)	1986-12-15	Medicaments qui contiennent d'alpha-(n-pyrrolyl)-acides ou de leurs sels ou esters.
CH620678A5 (en)	1980-12-15	Process for the preparation of a derivative of piperidine