CA1108151A - 3-(1h-tetrazol-5-yl) chromones - Google Patents

3-(1h-tetrazol-5-yl) chromones

Info

Publication number: CA1108151A
Authority: CA; Canada
Prior art keywords: tetrazol; methoxy; chromones; compounds; compound
Prior art date: 1978-10-03
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

CA312,620A

Other languages

English (en)

Inventor

Max Von Strandtmann

Sylvester Klutchko

Marvin P. Cohen

John Shavel, Jr.

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.)

Warner Lambert Co LLC

Original Assignee

Warner Lambert Co LLC

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.)

1978-10-03

Filing date

1978-10-03

Publication date

1981-09-01

1978-10-03 Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC

1978-10-03 Priority to CA312,620A priority Critical patent/CA1108151A/fr

1981-09-01 Application granted granted Critical

1981-09-01 Publication of CA1108151A publication Critical patent/CA1108151A/fr

Status Expired legal-status Critical Current

Links

HJOBCUUZGWRLTO-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)chromen-4-one Chemical class C=1OC2=CC=CC=C2C(=O)C=1C=1N=NNN=1 HJOBCUUZGWRLTO-UHFFFAOYSA-N 0.000 title claims abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 20
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
KBGGLVWRGYLXRF-UHFFFAOYSA-N 8-methoxy-3-(2h-tetrazol-5-yl)chromen-4-one Chemical compound COC1=CC=CC(C2=O)=C1OC=C2C1=NN=NN1 KBGGLVWRGYLXRF-UHFFFAOYSA-N 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 4
RWYNFTSXZRBELM-UHFFFAOYSA-N 8-methoxy-4-oxochromene-3-carbonitrile Chemical compound O1C=C(C#N)C(=O)C2=C1C(OC)=CC=C2 RWYNFTSXZRBELM-UHFFFAOYSA-N 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims 1
206010027654 Allergic conditions Diseases 0.000 abstract description 4
208000006673 asthma Diseases 0.000 abstract description 4
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 abstract description 3
230000003266 anti-allergic effect Effects 0.000 abstract description 3
125000000217 alkyl group Chemical group 0.000 abstract description 2
125000003118 aryl group Chemical group 0.000 abstract description 2
229910052736 halogen Inorganic materials 0.000 abstract description 2
150000002367 halogens Chemical class 0.000 abstract description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 9
-1 3-substituted chromones Chemical class 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
239000003701 inert diluent Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000003380 propellant Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ZZLXVXGOFGHKHP-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)chromen-4-one Chemical class O1C2=CC=CC=C2C(=O)C=C1C=1N=NNN=1 ZZLXVXGOFGHKHP-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000004777 chromones Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000006199 nebulizer Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000008247 solid mixture Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
SFWNPLLGXKJESA-UHFFFAOYSA-N 4-oxochromene-3-carbonitrile Chemical class C1=CC=C2C(=O)C(C#N)=COC2=C1 SFWNPLLGXKJESA-UHFFFAOYSA-N 0.000 description 1
SHYUITMLENOEDS-UHFFFAOYSA-N 6-methoxy-3-(2h-tetrazol-5-yl)chromen-4-one Chemical compound O=C1C2=CC(OC)=CC=C2OC=C1C1=NN=NN1 SHYUITMLENOEDS-UHFFFAOYSA-N 0.000 description 1
CKEDZWWMONCZLW-UHFFFAOYSA-N 8-methoxy-4-oxochromene-3-carbaldehyde Chemical compound O1C=C(C=O)C(=O)C2=C1C(OC)=CC=C2 CKEDZWWMONCZLW-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
108010010803 Gelatin Proteins 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
241000700159 Rattus Species 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000008016 pharmaceutical coating Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA312,620A 1978-10-03 1978-10-03 3-(1h-tetrazol-5-yl) chromones Expired CA1108151A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA312,620A CA1108151A (fr)	1978-10-03	1978-10-03	3-(1h-tetrazol-5-yl) chromones

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA312,620A CA1108151A (fr)	1978-10-03	1978-10-03	3-(1h-tetrazol-5-yl) chromones

Publications (1)

Publication Number	Publication Date
CA1108151A true CA1108151A (fr)	1981-09-01

Family

ID=4112521

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA312,620A Expired CA1108151A (fr)	1978-10-03	1978-10-03	3-(1h-tetrazol-5-yl) chromones

Country Status (1)

Country	Link
CA (1)	CA1108151A (fr)

1978
- 1978-10-03 CA CA312,620A patent/CA1108151A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-09-01	MKEX	Expiry

Publication	Publication Date	Title
CA1088073A (fr)	1980-10-21	Agents therapeutiques a base d'hydantoine
CA1139761A (fr)	1983-01-18	Derives de tetrazolylalcoxycarbostyryle, et methode de fabrication
US4146631A (en)	1979-03-27	Benzamide derivatives
US3987185A (en)	1976-10-19	Method of treatment using 1-oxo-1h-2-benzopyran-3-carboxylic acid derivatives
US3887574A (en)	1975-06-03	Carboxamido tetrazolo chromones
JP2988944B2 (ja)	1999-12-13	アリールアルコキシクマリン、その製造方法及びこれを含有する治療剤
US4670457A (en)	1987-06-02	2H-benzofuran-3-one-derivatives and process for their preparation
JPS6084221A (ja)	1985-05-13	抗喘息薬としてのベンゾチオフエン誘導体
CA2194886A1 (fr)	1996-02-01	Nouveau compose chimique, sa preparation et son utilisation en tant que medicament
US4116971A (en)	1978-09-26	3-(1h-tetrazol-5-yl)chromones
CA1108151A (fr)	1981-09-01	3-(1h-tetrazol-5-yl) chromones
EP0190298B1 (fr)	1989-10-18	Acides 4-(isoxazolyl)-thiazole-2-oxamiques et leurs derives
CA1165321A (fr)	1984-04-10	Derives de la tetrazolylcoumarine, methode de preparation et compositions qui en renferment
SU858570A3 (ru)	1981-08-23	Способ получени производных 3-/тетразол-5-ил/-1-азаксантона или их солей
US4248879A (en)	1981-02-03	Benzopyranotriazoles
US4035368A (en)	1977-07-12	Substituted 3-(1H-tetrazol-5-yl)-quinoline compounds
JPS6222993B2 (fr)	1987-05-20
CA1286665C (fr)	1991-07-23	Derives pyrido [1,2a] pyrimidine
EP0184801B1 (fr)	1990-09-26	Dérivés du chromène, procédé pour leur préparation et compositions antiallergiques les contenant
CY1293A (en)	1985-10-18	Oxygen containing heterocyclics
US2502264A (en)	1950-03-28	Quinoline derivatives having antimalarial properties
EP0002562B1 (fr)	1981-05-20	Dérivés de la triazolo-quinoléine, procédés pour leur préparation et leur utilisation pharmaceutique
US4127669A (en)	1978-11-28	[(4-Oxo-4H-1-benzopyran-3-yl)oxy] acetic acids and derivatives
EP0104018A2 (fr)	1984-03-28	Dérivés de benzopyrane, thiabenzopyrane et quinoline et compositions pharmaceutiques les contenant
JPH0114911B2 (fr)	1989-03-14