DE2900656C2 - 2-(3'-Brom-4'-hydroxybenzoyl)- und 2-(3',5'-Dibrom-4'-hydroxybenzoyl)-chromone, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel - Google Patents

2-(3'-Brom-4'-hydroxybenzoyl)- und 2-(3',5'-Dibrom-4'-hydroxybenzoyl)-chromone, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel

Info

Publication number: DE2900656C2
Authority: DE; Germany
Prior art keywords: hydroxybenzoyl; udf54; udf53; chromone; dibromo
Prior art date: 1978-01-17
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

DE2900656A

Other languages

German (de)

English (en)

Other versions

DE2900656A1 (de

Inventor

Henri Clermont-Ferrand Chibret

Original Assignee

THEA (Thérapeutique et Applications) S.A., Joze, Marinques

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.)

1978-01-17

Filing date

1979-01-10

Publication date

1987-03-26

1978-01-17 Priority claimed from FR7801154A external-priority patent/FR2414506A1/fr

1979-01-10 Application filed by THEA (Thérapeutique et Applications) S.A., Joze, Marinques filed Critical THEA (Thérapeutique et Applications) S.A., Joze, Marinques

1979-07-19 Publication of DE2900656A1 publication Critical patent/DE2900656A1/de

1987-03-26 Application granted granted Critical

1987-03-26 Publication of DE2900656C2 publication Critical patent/DE2900656C2/de

Status Expired legal-status Critical Current

Links

ZORAVFNONZHSOD-UHFFFAOYSA-N 2-(3,5-dibromo-4-hydroxybenzoyl)chromen-4-one Chemical class C1=C(Br)C(O)=C(Br)C=C1C(=O)C1=CC(=O)C2=CC=CC=C2O1 ZORAVFNONZHSOD-UHFFFAOYSA-N 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 8
238000000034 method Methods 0.000 title claims description 6
239000003814 drug Substances 0.000 title description 5
OMSHDEIMZNVNNO-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC(=O)C2=CC=CC=C2O1 OMSHDEIMZNVNNO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
150000004777 chromones Chemical class 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
239000000463 material Substances 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
241000287828 Gallus gallus Species 0.000 description 17
235000013330 chicken meat Nutrition 0.000 description 17
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 11
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 11
229940116269 uric acid Drugs 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 8
230000002354 daily effect Effects 0.000 description 7
235000005911 diet Nutrition 0.000 description 7
230000037213 diet Effects 0.000 description 7
-1 2-(3'-bromo-4'-hydroxybenzoyl)-chromone Chemical compound 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
229960002529 benzbromarone Drugs 0.000 description 6
WHQCHUCQKNIQEC-UHFFFAOYSA-N benzbromarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 WHQCHUCQKNIQEC-UHFFFAOYSA-N 0.000 description 6
239000007903 gelatin capsule Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
241000700159 Rattus Species 0.000 description 5
239000008280 blood Substances 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
230000002255 enzymatic effect Effects 0.000 description 5
235000013372 meat Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
201000005569 Gout Diseases 0.000 description 4
201000001431 Hyperuricemia Diseases 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
108090000854 Oxidoreductases Proteins 0.000 description 4
102000004316 Oxidoreductases Human genes 0.000 description 4
108010093894 Xanthine oxidase Proteins 0.000 description 4
102100033220 Xanthine oxidase Human genes 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
229940075420 xanthine Drugs 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
229960002708 antigout preparations Drugs 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
210000004185 liver Anatomy 0.000 description 3
238000012360 testing method Methods 0.000 description 3
FAEHWELEABAGRQ-UHFFFAOYSA-N 4-oxochromene-2-carbonyl chloride Chemical compound C1=CC=C2OC(C(=O)Cl)=CC(=O)C2=C1 FAEHWELEABAGRQ-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
239000000872 buffer Substances 0.000 description 2
FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000011835 investigation Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
235000019796 monopotassium phosphate Nutrition 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000036325 urinary excretion Effects 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
241000271566 Aves Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
108010092464 Urate Oxidase Proteins 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000010171 animal model Methods 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
239000012496 blank sample Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000012754 cardiac puncture Methods 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000013213 extrapolation Methods 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000013467 fragmentation Methods 0.000 description 1
238000006062 fragmentation reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000010453 quartz Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000012546 transfer Methods 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Physical Education & Sports Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Pain & Pain Management (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Rheumatology (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)
Pyrane Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DE2900656A 1978-01-17 1979-01-10 2-(3'-Brom-4'-hydroxybenzoyl)- und 2-(3',5'-Dibrom-4'-hydroxybenzoyl)-chromone, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel Expired DE2900656C2 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7801154A FR2414506A1 (fr)	1978-01-17	1978-01-17	Nouvelle chromone a activite medicamenteuse
FR7836421A FR2445326A2 (fr)	1978-01-17	1978-12-27	Nouvelle chromone a activite medicamenteuse

Publications (2)

Publication Number	Publication Date
DE2900656A1 DE2900656A1 (de)	1979-07-19
DE2900656C2 true DE2900656C2 (de)	1987-03-26

Family

ID=26220400

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE2900656A Expired DE2900656C2 (de)	1978-01-17	1979-01-10	2-(3'-Brom-4'-hydroxybenzoyl)- und 2-(3',5'-Dibrom-4'-hydroxybenzoyl)-chromone, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel

Country Status (4)

Country	Link
JP (1)	JPS54112871A (es)
DE (1)	DE2900656C2 (es)
FR (1)	FR2445326A2 (es)
IT (1)	IT1166579B (es)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10256174A1 (de) *	2002-12-02	2004-06-09	Merck Patent Gmbh	2-Benzoylchromonderivate

1978
- 1978-12-27 FR FR7836421A patent/FR2445326A2/fr active Granted
1979
- 1979-01-10 DE DE2900656A patent/DE2900656C2/de not_active Expired
- 1979-01-16 IT IT19312/79A patent/IT1166579B/it active
- 1979-01-17 JP JP441179A patent/JPS54112871A/ja active Granted

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NICHTS-ERMITTELT

Also Published As

Publication number	Publication date
IT7919312A0 (it)	1979-01-16
FR2445326A2 (fr)	1980-07-25
JPS6160837B2 (es)	1986-12-23
DE2900656A1 (de)	1979-07-19
JPS54112871A (en)	1979-09-04
FR2445326B2 (es)	1981-02-27
IT1166579B (it)	1987-05-05

Legal Events

Date	Code	Title
1985-07-11	8110	Request for examination paragraph 44
1987-03-26	D2	Grant after examination
1987-09-24	8364	No opposition during term of opposition
1990-01-11	8339	Ceased/non-payment of the annual fee

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