NO302233B1 - Nye, terapeutisk virksomme benzopyranderivater - Google Patents

Nye, terapeutisk virksomme benzopyranderivater Download PDF

Info

Publication number: NO302233B1
Authority: NO; Norway
Prior art keywords: formula; methyl; benzopyran; oxo; dihydropyridin
Prior art date: 1991-08-29

Application number

NO923382A

Other languages

English (en)

Norwegian (no)

Other versions

NO923382L (no

NO923382D0 (no

Inventor

Alistair William Lochead

Michel Jacques Navet

Peter Edwin Hicks

Original Assignee

Syntex Inc

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.)

1991-08-29

Filing date

1992-08-28

Publication date

1998-02-09

1992-08-28 Application filed by Syntex Inc filed Critical Syntex Inc

1992-08-28 Publication of NO923382D0 publication Critical patent/NO923382D0/no

1993-03-01 Publication of NO923382L publication Critical patent/NO923382L/no

1998-02-09 Publication of NO302233B1 publication Critical patent/NO302233B1/no

Links

150000001562 benzopyrans Chemical class 0.000 title claims description 13
150000001875 compounds Chemical class 0.000 claims description 401
239000001257 hydrogen Substances 0.000 claims description 154
229910052739 hydrogen Inorganic materials 0.000 claims description 154
125000000217 alkyl group Chemical group 0.000 claims description 105
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 85
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 80
150000003839 salts Chemical class 0.000 claims description 66
150000002431 hydrogen Chemical class 0.000 claims description 61
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 44
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
125000003545 alkoxy group Chemical group 0.000 claims description 25
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
229910052794 bromium Inorganic materials 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
125000001246 bromo group Chemical group Br* 0.000 claims description 15
239000000825 pharmaceutical preparation Substances 0.000 claims description 13
231100000252 nontoxic Toxicity 0.000 claims description 9
230000003000 nontoxic effect Effects 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
FXRJKZVWFJSKGI-UHFFFAOYSA-N n-[[2,2-dimethyl-4-(2-oxopyridin-1-yl)-6-(trifluoromethyl)chromen-3-yl]methyl]-n-hydroxyacetamide Chemical compound C12=CC(C(F)(F)F)=CC=C2OC(C)(C)C(CN(O)C(=O)C)=C1N1C=CC=CC1=O FXRJKZVWFJSKGI-UHFFFAOYSA-N 0.000 claims description 8
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 8
BSCZLAXSQNDWLZ-UHFFFAOYSA-N N-hydroxy-N-[2,2,5-trimethyl-6-nitro-4-(2-oxopyridin-1-yl)chromen-3-yl]acetamide Chemical compound [N+](=O)([O-])C=1C=CC2=C(C(=C(C(O2)(C)C)N(C(C)=O)O)N2C(C=CC=C2)=O)C=1C BSCZLAXSQNDWLZ-UHFFFAOYSA-N 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
XITSSGJCHKTHNV-UHFFFAOYSA-N C(#N)C=1C=CC2=C(C(=C(C(O2)(C)C)N(C(C)=O)O)N2C(C=CC=C2)=O)C1C Chemical compound C(#N)C=1C=CC2=C(C(=C(C(O2)(C)C)N(C(C)=O)O)N2C(C=CC=C2)=O)C1C XITSSGJCHKTHNV-UHFFFAOYSA-N 0.000 claims description 6
239000000969 carrier Substances 0.000 claims description 6
CXPLYZVAVAOCLJ-UHFFFAOYSA-N N-[2,2,5-trimethyl-6-nitro-4-(2-oxopyridin-1-yl)chromen-3-yl]acetamide Chemical compound [N+](=O)([O-])C=1C=CC2=C(C(=C(C(O2)(C)C)NC(C)=O)N2C(C=CC=C2)=O)C=1C CXPLYZVAVAOCLJ-UHFFFAOYSA-N 0.000 claims description 5
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LMPQGZDAOUOFPE-UHFFFAOYSA-N n-[[2,2-dimethyl-6-nitro-4-(2-oxopyridin-1-yl)chromen-3-yl]methyl]formamide Chemical compound O=CNCC=1C(C)(C)OC2=CC=C([N+]([O-])=O)C=C2C=1N1C=CC=CC1=O LMPQGZDAOUOFPE-UHFFFAOYSA-N 0.000 claims description 5
WRUWFSISNDFGPN-UHFFFAOYSA-N CC1(C)OC(C=CC(C(C(F)(F)F)(F)F)=C2C)=C2C(N(C=CC=C2)C2=O)=C1N(C(C)=O)O Chemical compound CC1(C)OC(C=CC(C(C(F)(F)F)(F)F)=C2C)=C2C(N(C=CC=C2)C2=O)=C1N(C(C)=O)O WRUWFSISNDFGPN-UHFFFAOYSA-N 0.000 claims description 4
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125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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MMIAOQJHUALFSF-UHFFFAOYSA-N 1-[3-(methoxyamino)-2,2,5-trimethyl-6-nitrochromen-4-yl]pyridin-2-one Chemical compound [N+](=O)([O-])C=1C=CC2=C(C(=C(C(O2)(C)C)NOC)N2C(C=CC=C2)=O)C=1C MMIAOQJHUALFSF-UHFFFAOYSA-N 0.000 claims description 3
OYDMTNATKBXKTJ-UHFFFAOYSA-N 2,2,2-trifluoro-n-[2,2,5-trimethyl-4-(2-oxopyridin-1-yl)-6-(trifluoromethyl)chromen-3-yl]acetamide Chemical compound FC(F)(F)C(=O)NC=1C(C)(C)OC2=CC=C(C(F)(F)F)C(C)=C2C=1N1C=CC=CC1=O OYDMTNATKBXKTJ-UHFFFAOYSA-N 0.000 claims description 3
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229910052799 carbon Inorganic materials 0.000 claims description 3
IASZFMFGJXHDKR-UHFFFAOYSA-N n-[[2,2-dimethyl-6-nitro-4-(2-oxopyridin-1-yl)chromen-3-yl]methyl]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)NCC=1C(C)(C)OC2=CC=C([N+]([O-])=O)C=C2C=1N1C=CC=CC1=O IASZFMFGJXHDKR-UHFFFAOYSA-N 0.000 claims description 2
ALRMNUBOFIIHKG-UHFFFAOYSA-N N-[2,2,5-trimethyl-4-(2-oxopyridin-1-yl)-6-(trifluoromethyl)chromen-3-yl]acetamide Chemical compound FC(C=1C=CC2=C(C(=C(C(O2)(C)C)NC(C)=O)N2C(C=CC=C2)=O)C=1C)(F)F ALRMNUBOFIIHKG-UHFFFAOYSA-N 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
238000002360 preparation method Methods 0.000 description 190
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
238000000034 method Methods 0.000 description 48
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239000000203 mixture Substances 0.000 description 39
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
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230000002829 reductive effect Effects 0.000 description 24
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150000001412 amines Chemical class 0.000 description 13
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NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 12
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
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APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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DCQXTYAFFMSNNH-UHFFFAOYSA-M sodium;2-[bis(2-hydroxyethyl)amino]ethanol;acetate Chemical compound [Na+].CC([O-])=O.OCCN(CCO)CCO DCQXTYAFFMSNNH-UHFFFAOYSA-M 0.000 description 1
239000003506 spasmogen Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pulmonology (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Vascular Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO923382A 1991-08-29 1992-08-28 Nye, terapeutisk virksomme benzopyranderivater NO302233B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/751,491 US5250547A (en)	1991-08-29	1991-08-29	Benzopyran derivatives

Publications (3)

Publication Number	Publication Date
NO923382D0 NO923382D0 (no)	1992-08-28
NO923382L NO923382L (no)	1993-03-01
NO302233B1 true NO302233B1 (no)	1998-02-09

Family

ID=25022219

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO923382A NO302233B1 (no)	1991-08-29	1992-08-28	Nye, terapeutisk virksomme benzopyranderivater

Country Status (15)

Country	Link
US (2)	US5250547A (fi)
EP (1)	EP0529654A1 (fi)
JP (1)	JPH05213940A (fi)
KR (1)	KR100235165B1 (fi)
AU (1)	AU653245B2 (fi)
CA (1)	CA2077098A1 (fi)
FI (1)	FI923872A (fi)
HU (1)	HUT65384A (fi)
IL (1)	IL102980A (fi)
IT (1)	IT1256948B (fi)
MX (1)	MX9205003A (fi)
NO (1)	NO302233B1 (fi)
NZ (1)	NZ244123A (fi)
TW (1)	TW203611B (fi)
ZA (1)	ZA926549B (fi)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0549729B1 (en) *	1990-09-07	1997-12-17	Schering Corporation	Antiviral compounds and antihypertensive compounds
CA2148220A1 (en) *	1992-11-06	1994-05-26	Kiyoshi Tamura	Method for producing composition for solid medicine
GB9226302D0 (en) *	1992-12-17	1993-02-10	Smithkline Beecham Plc	Pharmaceuticals
US5482942A (en) *	1994-06-28	1996-01-09	American Home Products Corporation	(3,4-dioxocyclobuten-1-yl)chromene, indene, and dihydronaphthalenone derivatives as smooth muscle relaxants
TW533073B (en) *	1997-03-03	2003-05-21	Chugai Pharmaceutical Co Ltd	Therapeutic agents for peripheral vascular disease
US6077850A (en)	1997-04-21	2000-06-20	G.D. Searle & Co.	Substituted benzopyran analogs for the treatment of inflammation
US6034256A (en) *	1997-04-21	2000-03-07	G.D. Searle & Co.	Substituted benzopyran derivatives for the treatment of inflammation
EP1034793B1 (en) *	1998-08-17	2005-10-26	Senju Pharmaceutical Co., Ltd.	Preventives/remedies for glaucoma
US20040198800A1 (en) *	2002-12-19	2004-10-07	Geoffrey Allan	Lipoxygenase inhibitors as hypolipidemic and anti-hypertensive agents
US7470798B2 (en)	2003-09-19	2008-12-30	Edison Pharmaceuticals, Inc.	7,8-bicycloalkyl-chroman derivatives
KR100602191B1 (ko) *	2004-03-10	2006-07-19	한국화학연구원	5-라이폭시게네이즈 저해활성을 가지는2,2'-이중치환-3,4-디하이드로-7,8-이중치환-6-알킬아미노벤조피란 유도체
MX2007007103A (es) *	2004-12-13	2008-03-10	Lilly Co Eli	Derivados espiro como inhibidores de lipoxigenasa.
WO2006093548A1 (en)	2005-02-25	2006-09-08	Galileo Pharmaceuticals, Inc.	Spiro-heterocyclic chromans, thiochromans and dihydroquinolines
JP2006306791A (ja) *	2005-04-28	2006-11-09	Kanebo Cosmetics Inc	養毛剤
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1991
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1992
- 1992-08-28 ZA ZA926549A patent/ZA926549B/xx unknown
- 1992-08-28 IT ITTO920719A patent/IT1256948B/it active IP Right Grant
- 1992-08-28 IL IL102980A patent/IL102980A/en not_active IP Right Cessation
- 1992-08-28 NZ NZ244123A patent/NZ244123A/en unknown
- 1992-08-28 EP EP92114748A patent/EP0529654A1/en not_active Withdrawn
- 1992-08-28 JP JP4272259A patent/JPH05213940A/ja active Pending
- 1992-08-28 KR KR1019920015534A patent/KR100235165B1/ko not_active IP Right Cessation
- 1992-08-28 CA CA002077098A patent/CA2077098A1/en not_active Abandoned
- 1992-08-28 HU HU9202777A patent/HUT65384A/hu unknown
- 1992-08-28 FI FI923872A patent/FI923872A/fi unknown
- 1992-08-28 TW TW081106811A patent/TW203611B/zh active
- 1992-08-28 AU AU21333/92A patent/AU653245B2/en not_active Ceased
- 1992-08-28 NO NO923382A patent/NO302233B1/no not_active IP Right Cessation
- 1992-08-31 MX MX9205003A patent/MX9205003A/es not_active IP Right Cessation
1993
- 1993-07-22 US US08/096,583 patent/US5447943A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
KR930004290A (ko)	1993-03-22
US5447943A (en)	1995-09-05
NZ244123A (en)	1995-06-27
JPH05213940A (ja)	1993-08-24
NO923382L (no)	1993-03-01
HU9202777D0 (en)	1992-12-28
ZA926549B (en)	1994-02-28
FI923872A (fi)	1993-03-01
IT1256948B (it)	1995-12-27
EP0529654A1 (en)	1993-03-03
ITTO920719A0 (it)	1992-08-28
NO923382D0 (no)	1992-08-28
FI923872A0 (fi)	1992-08-28
KR100235165B1 (ko)	1999-12-15
CA2077098A1 (en)	1993-03-01
AU2133392A (en)	1993-03-11
AU653245B2 (en)	1994-09-22
HUT65384A (en)	1994-05-02
ITTO920719A1 (it)	1994-02-28
US5250547A (en)	1993-10-05
IL102980A (en)	1998-04-05
MX9205003A (es)	1993-04-30
TW203611B (fi)	1993-04-11

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