CA1110249A - Indolopyrones having antiallergic activity - Google Patents

Indolopyrones having antiallergic activity

Info

Publication number: CA1110249A
Authority: CA; Canada
Prior art keywords: dihydro; indole; oxopyrano; carboxamide; ethyl
Prior art date: 1977-09-30
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

CA312,357A

Other languages

English (en)

French (fr)

Inventor

Richard E. Brown

Paul C. Unangst

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.)

1977-09-30

Filing date

1978-09-29

Publication date

1981-10-06

1978-09-29 Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC

1981-10-06 Application granted granted Critical

1981-10-06 Publication of CA1110249A publication Critical patent/CA1110249A/en

Status Expired legal-status Critical Current

Links

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230000003266 anti-allergic effect Effects 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 26
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000005518 carboxamido group Chemical group 0.000 claims abstract description 9
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239000001257 hydrogen Substances 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 7
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125000003118 aryl group Chemical group 0.000 claims abstract description 4
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238000000034 method Methods 0.000 claims description 21
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 14
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 10
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VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 claims description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
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NPTCUKMDGULPHV-UHFFFAOYSA-N 4-oxo-5-phenylpyrano[3,2-b]indole-2-carbonitrile Chemical compound C1=2C(=O)C=C(C#N)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 NPTCUKMDGULPHV-UHFFFAOYSA-N 0.000 claims 3
DRILWLNMLYTSJJ-UHFFFAOYSA-N 4-oxo-5-phenylpyrano[3,2-b]indole-2-carboxamide Chemical compound C12=CC=CC=C2C=2OC(C(=O)N)=CC(=O)C=2N1C1=CC=CC=C1 DRILWLNMLYTSJJ-UHFFFAOYSA-N 0.000 claims 3
NMRNQVTUXYHYJC-UHFFFAOYSA-N 5-ethyl-4-oxopyrano[3,2-b]indole-2-carboxamide Chemical compound O1C(C(N)=O)=CC(=O)C2=C1C1=CC=CC=C1N2CC NMRNQVTUXYHYJC-UHFFFAOYSA-N 0.000 claims 3
VFFKMULPAXIRGL-UHFFFAOYSA-N 5-methyl-4-oxopyrano[3,2-b]indole-2-carbonitrile Chemical compound O1C(C#N)=CC(=O)C2=C1C1=CC=CC=C1N2C VFFKMULPAXIRGL-UHFFFAOYSA-N 0.000 claims 3
NPXNAEKNDFKQAM-UHFFFAOYSA-N 5-methyl-2-(2h-tetrazol-5-yl)pyrano[3,2-b]indol-4-one Chemical compound C=1C(=O)C=2N(C)C3=CC=CC=C3C=2OC=1C=1N=NNN=1 NPXNAEKNDFKQAM-UHFFFAOYSA-N 0.000 claims 2
UVESJWIYABDXET-UHFFFAOYSA-N 5-methyl-4-oxopyrano[3,2-b]indole-2-carboxamide Chemical compound O1C(C(N)=O)=CC(=O)C2=C1C1=CC=CC=C1N2C UVESJWIYABDXET-UHFFFAOYSA-N 0.000 claims 2
GVQWDVAARZRQCS-UHFFFAOYSA-N 5-phenyl-2-(2h-tetrazol-5-yl)pyrano[3,2-b]indol-4-one Chemical compound C1=2C(=O)C=C(C=3NN=NN=3)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 GVQWDVAARZRQCS-UHFFFAOYSA-N 0.000 claims 2
JLYSISATEGWXFV-UHFFFAOYSA-N 5-ethyl-4-oxopyrano[3,2-b]indole-2-carbonitrile Chemical compound O1C(C#N)=CC(=O)C2=C1C1=CC=CC=C1N2CC JLYSISATEGWXFV-UHFFFAOYSA-N 0.000 claims 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA312,357A 1977-09-30 1978-09-29 Indolopyrones having antiallergic activity Expired CA1110249A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US83820077A	1977-09-30	1977-09-30
US838,200		1977-09-30

Publications (1)

Publication Number	Publication Date
CA1110249A true CA1110249A (en)	1981-10-06

Family

ID=25276532

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA312,357A Expired CA1110249A (en)	1977-09-30	1978-09-29	Indolopyrones having antiallergic activity

Country Status (8)

Country	Link
JP (1)	JPS5470300A (da)
AU (1)	AU522053B2 (da)
CA (1)	CA1110249A (da)
DE (1)	DE2837236A1 (da)
DK (1)	DK432778A (da)
FR (1)	FR2404640A1 (da)
GB (1)	GB2004885B (da)
IT (1)	IT1107244B (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4503236A (en) *	1982-04-19	1985-03-05	Warner-Lambert Company	Antiallergic 4Hfuro[3,2-b]indoles
US4596814A (en) *	1983-01-10	1986-06-24	Warner-Lambert Company	Tetrazolyl- and carboxamidotetrazolyl-substituted 4H-furo[3,2-b] indoles and anti-allergic use thereof
JP5498795B2 (ja) *	2007-11-12	2014-05-21	山本化成株式会社	有機トランジスタ
CN114702504B (zh) *	2022-01-29	2023-04-07	平顶山学院	三氟甲基取代吲哚并吡喃酮化合物及其制备方法和在抗肿瘤药物中的应用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4028383A (en) *	1975-09-08	1977-06-07	Warner-Lambert Company	Indolopyrones having antiallergic activity

1978
- 1978-08-25 DE DE19782837236 patent/DE2837236A1/de not_active Ceased
- 1978-09-12 FR FR7826102A patent/FR2404640A1/fr active Granted
- 1978-09-27 IT IT51273/78A patent/IT1107244B/it active
- 1978-09-28 AU AU40288/78A patent/AU522053B2/en not_active Expired
- 1978-09-28 GB GB7838490A patent/GB2004885B/en not_active Expired
- 1978-09-29 JP JP11939878A patent/JPS5470300A/ja active Pending
- 1978-09-29 DK DK432778A patent/DK432778A/da not_active Application Discontinuation
- 1978-09-29 CA CA312,357A patent/CA1110249A/en not_active Expired

Also Published As

Publication number	Publication date
JPS5470300A (en)	1979-06-05
AU522053B2 (en)	1982-05-13
DE2837236A1 (de)	1979-04-05
DK432778A (da)	1979-03-31
FR2404640B1 (da)	1981-07-24
FR2404640A1 (fr)	1979-04-27
IT7851273A0 (it)	1978-09-27
GB2004885B (en)	1982-03-24
GB2004885A (en)	1979-04-11
AU4028878A (en)	1980-04-03
IT1107244B (it)	1985-11-25

Legal Events

Date	Code	Title	Description
1998-10-06	MKEX	Expiry

Publication	Publication Date	Title
EP0269295B1 (en)	1991-06-26	Therapeutic agents
US4503066A (en)	1985-03-05	Spiro-linked pyrrolidine-2,5-diones active as enzyme aldose reductase inhibitors
US4639454A (en)	1987-01-27	Phenylquinazolinecarboxylic acids and derivatives as cancer chemotherapeutic agents
US5221681A (en)	1993-06-22	Substituted benzoxazepines and benzothiazepines
US4314943A (en)	1982-02-09	Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols
US3927023A (en)	1975-12-16	Imidazolyl benzofurans
CA1110249A (en)	1981-10-06	Indolopyrones having antiallergic activity
EP0055068B1 (en)	1984-10-17	Quinolone derivatives and their use as pharmaceuticals
US4190659A (en)	1980-02-26	Pharmaceutical preparation and use of 4-hydroxy-2-quinolinone-3-carboxylic acid esters
US4144337A (en)	1979-03-13	1,4-Substituted piperazinyl derivatives useful as psychostimulants
US3373168A (en)	1968-03-12	Certain benzazepinoxyridoindole compounds and their preparation
NO155056B (no)	1986-10-27	Sprengstoff.
US3984429A (en)	1976-10-05	Pharmaceutically active compounds
CA1051900A (en)	1979-04-03	1-hydroxymethyl-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine compounds
US4440768A (en)	1984-04-03	Hexahydropyrrolo[3,4-c]quinoline compounds and pharmaceutical compositions, and methods for their use
EP0138490B1 (en)	1988-04-27	4-alkyl methylenedioxy-2-1[H]-quinazolinones
US4260612A (en)	1981-04-07	Antiallergic nitrogen bridge-head compounds
US4757070A (en)	1988-07-12	3-oxadiazolyl-5-aminoalkyl-beta-carboline derivatives compositions and use
US4316904A (en)	1982-02-23	Indolopyrone tetrazoles and carboxamidotetrazoles having antiallergic activity
EP0184801B1 (en)	1990-09-26	Chromene derivative, process for preparing the same and antiallergic agent containing the same
US4136186A (en)	1979-01-23	Thieno[3,2-c]pyridine derivatives
US4221797A (en)	1980-09-09	Dihydroquinoline-one derivatives
US4598076A (en)	1986-07-01	2-pyrrolin-3-carbonitril-derivatives, pharmaceutical compositions containing them and their anti-inflammatory and ulcer protective activity
US3972883A (en)	1976-08-03	1,6-Dimethyl-8β-[2' or 3'-pyrroyloxyethyl or substituted pyrroyloxyethyl]-10α-methoxyergolene compounds
US4495352A (en)	1985-01-22	Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols