PH25958A - Benzofurans and benzothiophenes having antiallergic activity pharmaceutical compositions containing the same and method of use thereof - Google Patents

Benzofurans and benzothiophenes having antiallergic activity pharmaceutical compositions containing the same and method of use thereof Download PDF

Info

Publication number: PH25958A
Authority: PH; Philippines
Prior art keywords: compound; thiophene; benzo; tetrazol; carboxamide
Prior art date: 1987-07-14

Application number

PH37219A

Other languages

English (en)

Inventor

David Thomas Connor

Roderick Joseph Sorenson

David Orel Thueson

Michael David Mullican

Original Assignee

Warner Lambert Co

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.)

1987-07-14

Filing date

1988-07-13

Publication date

1992-01-13

1988-07-13 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

1992-01-13 Publication of PH25958A publication Critical patent/PH25958A/en

Links

230000003266 anti-allergic effect Effects 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 32
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title abstract description 15
150000001907 coumarones Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 67
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 42
239000000203 mixture Substances 0.000 claims description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 21
238000010992 reflux Methods 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
239000007787 solid Substances 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
239000002552 dosage form Substances 0.000 claims description 7
-1 nitro, amino Chemical group 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
241000282414 Homo sapiens Species 0.000 claims description 6
206010020751 Hypersensitivity Diseases 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
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230000007815 allergy Effects 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
230000004054 inflammatory process Effects 0.000 claims description 5
201000004681 Psoriasis Diseases 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
208000026935 allergic disease Diseases 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
QZHGFALVBFEAES-UHFFFAOYSA-N 5-methoxy-6-phenylmethoxy-3-propan-2-yloxy-1-benzothiophene-2-carboxylic acid Chemical compound COC1=CC=2C(OC(C)C)=C(C(O)=O)SC=2C=C1OCC1=CC=CC=C1 QZHGFALVBFEAES-UHFFFAOYSA-N 0.000 claims description 2
230000003110 anti-inflammatory effect Effects 0.000 claims description 2
230000002682 anti-psoriatic effect Effects 0.000 claims description 2
150000003857 carboxamides Chemical class 0.000 claims 3
XRUQMNVURXXUSZ-UHFFFAOYSA-N 5-methoxy-6-phenylmethoxy-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)-1-benzothiophene-2-carboxamide Chemical compound COC1=CC=2C(OC(C)C)=C(C(=O)NC=3NN=NN=3)SC=2C=C1OCC1=CC=CC=C1 XRUQMNVURXXUSZ-UHFFFAOYSA-N 0.000 claims 1
RTIXKCRFFJGDFG-UHFFFAOYSA-N chrysin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 RTIXKCRFFJGDFG-UHFFFAOYSA-N 0.000 claims 1
AVBDPKLHYNAMQS-UHFFFAOYSA-N di(imidazol-1-yl)methanone 1H-imidazole Chemical compound C(=O)(N1C=NC=C1)N1C=NC=C1.N1C=NC=C1 AVBDPKLHYNAMQS-UHFFFAOYSA-N 0.000 claims 1
150000002460 imidazoles Chemical class 0.000 claims 1
DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 10
206010001052 Acute respiratory distress syndrome Diseases 0.000 abstract description 8
201000000028 adult respiratory distress syndrome Diseases 0.000 abstract description 7
208000013616 Respiratory Distress Syndrome Diseases 0.000 abstract description 6
KWJGNLIHELNBDN-UHFFFAOYSA-N tetrazole-2-carboxamide Chemical class NC(=O)N1N=CN=N1 KWJGNLIHELNBDN-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000000047 product Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000001953 recrystallisation Methods 0.000 description 13
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
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230000005764 inhibitory process Effects 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
239000000725 suspension Substances 0.000 description 7
239000006188 syrup Substances 0.000 description 7
235000020357 syrup Nutrition 0.000 description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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229910052786 argon Inorganic materials 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
239000002002 slurry Substances 0.000 description 5
208000024891 symptom Diseases 0.000 description 5
DTMXTCKEPQWRPO-UHFFFAOYSA-N 3-chloro-6-methoxy-1-benzothiophene-2-carbonyl chloride Chemical compound COC1=CC=C2C(Cl)=C(C(Cl)=O)SC2=C1 DTMXTCKEPQWRPO-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000003556 assay Methods 0.000 description 4
150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
210000003630 histaminocyte Anatomy 0.000 description 4
210000000440 neutrophil Anatomy 0.000 description 4
239000011734 sodium Substances 0.000 description 4
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
208000024172 Cardiovascular disease Diseases 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
102220498920 Transcriptional protein SWT1_C21A_mutation Human genes 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
208000003455 anaphylaxis Diseases 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
201000010099 disease Diseases 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
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239000005457 ice water Substances 0.000 description 3
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238000002360 preparation method Methods 0.000 description 3
230000008569 process Effects 0.000 description 3
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239000011780 sodium chloride Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 2
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RJXUGUBKNZNIJV-UHFFFAOYSA-N 5,6-dimethoxy-3-phenoxy-1-benzothiophene-2-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2SC(C(O)=O)=C1OC1=CC=CC=C1 RJXUGUBKNZNIJV-UHFFFAOYSA-N 0.000 description 2
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LELKSZPZTRAHOA-UHFFFAOYSA-N 1h-imidazole;5-methoxy-6-phenylmethoxy-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)-1-benzothiophene-2-carboxamide Chemical compound C1=CNC=N1.COC1=CC=2C(OC(C)C)=C(C(=O)NC=3NN=NN=3)SC=2C=C1OCC1=CC=CC=C1 LELKSZPZTRAHOA-UHFFFAOYSA-N 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Epidemiology (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Pulmonology (AREA)
Immunology (AREA)
Vascular Medicine (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)
Saccharide Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

PH37219A 1987-07-14 1988-07-13 Benzofurans and benzothiophenes having antiallergic activity pharmaceutical compositions containing the same and method of use thereof PH25958A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7355487A	1987-07-14	1987-07-14
US19169988A	1988-05-17	1988-05-17

Publications (1)

Publication Number	Publication Date
PH25958A true PH25958A (en)	1992-01-13

Family

ID=26754606

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH37219A PH25958A (en)	1987-07-14	1988-07-13	Benzofurans and benzothiophenes having antiallergic activity pharmaceutical compositions containing the same and method of use thereof

Country Status (16)

Country	Link
EP (1)	EP0299457B1 (de)
JP (1)	JP2672980B2 (de)
KR (1)	KR970011580B1 (de)
CN (1)	CN1031084A (de)
AT (1)	ATE111908T1 (de)
AU (1)	AU605070B2 (de)
CA (1)	CA1330562C (de)
DE (1)	DE3851584T2 (de)
DK (1)	DK175933B1 (de)
ES (1)	ES2063747T3 (de)
FI (1)	FI91256C (de)
IE (1)	IE64995B1 (de)
NO (1)	NO170886C (de)
NZ (1)	NZ225378A (de)
PH (1)	PH25958A (de)
PT (1)	PT87975B (de)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2689129B1 (fr) *	1992-03-27	1995-05-12	Atochem Elf Sa	Nouveaux dérivés de l'acide 3-mercapto-2-thénoique et leurs procédés de préparation.
US5426191A (en) *	1993-12-03	1995-06-20	Warner-Lambert Company	Process for the synthesis of 3-chlorobenzo[b]thiophene-2-carbonyl chlorides
FR2719476B1 (fr) *	1994-05-05	1997-05-23	Oreal	Utilisation d'un antagoniste de substance P dans une composition cosmétique et composition obtenue.
FR2719474B1 (fr)	1994-05-05	1996-05-31	Oreal	Utilisation d'un antagoniste de substance P dans une composition cosmétique et composition obtenue.
US6203803B1 (en)	1994-12-14	2001-03-20	Societe L'oreal S.A.	Use of a substance P antagonist in a cosmetic composition, and the composition thus obtained
FR2728166A1 (fr)	1994-12-19	1996-06-21	Oreal	Composition topique contenant un antagoniste de substance p
FR2728793A1 (fr) *	1994-12-28	1996-07-05	Oreal	Utilisation d'un antagoniste d'histamine, d'un antagoniste d'interleukine 1 et/ou d'un antagoniste de tnf-alpha dans une composition cosmetique, pharmaceutique ou dermatologique et composition obtenue
DE19620508A1 (de) *	1996-05-22	1997-11-27	Hoechst Ag	Schwefelenthaltende heterocyclische Bradykinin-Antagonisten, Verfahren zu ihrer Herstellung und ihre Verwendung
BRPI0410913A (pt) *	2003-06-05	2006-06-27	Warner Lambert Co	benzotiofenos substituìdos com cicloalquil e heterocicloalquil como agentes terapêuticos
CA2527779A1 (en) *	2003-06-05	2004-12-16	Warner-Lambert Company Llc	3-substituted indoles and derivatives thereof as therapeutic agents
JP2006526614A (ja) *	2003-06-05	2006-11-24	ワーナー−ランバートカンパニーリミティドライアビリティーカンパニー	治療用剤としての３−アリールスルファニル及び３−ヘテロアリールスルファニル置換ベンゾ［ｂ］チオフェン
MXPA05013210A (es) *	2003-06-05	2006-03-09	Warner Lambert Co	Benzo[b]tiofenos cicloalquilsulfanil-sustituidos como agentes terapeuticos.
US20040259926A1 (en) *	2003-06-05	2004-12-23	Bruendl Michelle M.	3-Aryloxy and 3-heteroaryloxy substituted benzo[b]thiophenes as therapeutic agents
BRPI0414171A (pt) *	2003-09-04	2006-10-31	Warner Lambert Co	benzo[b]tiofenos halossubstituìdos com atividade inibidora de pi3k como agentes terapêuticos
FR2862645B1 (fr) *	2003-11-20	2007-06-22	Merck Sante Sas	Composes antidiabetiques contenant des derives benzofuranes, benzothiophenes
US7674822B2 (en)	2004-11-24	2010-03-09	Wyeth	PTP1b inhibitors

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4140785A (en) *	1978-05-08	1979-02-20	E. I. Du Pont De Nemours And Company	N-(benzothienopyrazol)amide antirhinoviral agents
US4432986A (en) *	1979-06-18	1984-02-21	Riker Laboratories, Inc.	Tetrazoles bonded to certain polycyclic aromatic systems and anti-allergic use thereof
EP0146243A1 (de) *	1983-10-31	1985-06-26	Merck Frosst Canada Inc.	Lipoxygenase-Inhibitoren
GB8401288D0 (en) *	1984-01-18	1984-02-22	Pfizer Ltd	Therapeutic agents
GB8426474D0 (en) *	1984-10-19	1984-11-28	Ici America Inc	Heterocyclic amides
ZA858748B (en) *	1984-12-10	1987-06-24	Warner Lambert Co	Novel benzothiophenes and benzofurans having antiallergy activity
US4675332A (en) *	1984-12-10	1987-06-23	Warner-Lambert Company	Acidic tetrazolyl substituted indole compounds and their use as antiallergy agents
IE58555B1 (en) *	1984-12-10	1993-10-06	Warner Almbert Company	Novel benzothiophenes and benzofurans having antiallergy activity
US4748183A (en) *	1986-06-13	1988-05-31	Warner-Lambert Company	N-1H-tetrazol-5-yl-2-thiophene carboxamides, N-1H-tetrazol-5-yl-2-pyrrole carboxamides, N-1H-tetrazol-5-yl-2-furan carboxamides, and anti-allergic and anti-inflammatory use thereof
EP0253650A3 (de) *	1986-07-18	1989-09-13	Eli Lilly And Company	Benzothiophen-Derivate

1988
- 1988-06-21 IE IE187988A patent/IE64995B1/en not_active IP Right Cessation
- 1988-06-30 AU AU18577/88A patent/AU605070B2/en not_active Ceased
- 1988-06-30 CA CA000570900A patent/CA1330562C/en not_active Expired - Fee Related
- 1988-07-11 FI FI883300A patent/FI91256C/fi not_active IP Right Cessation
- 1988-07-12 NZ NZ225378A patent/NZ225378A/en unknown
- 1988-07-12 NO NO883100A patent/NO170886C/no unknown
- 1988-07-12 DK DK198803884A patent/DK175933B1/da not_active IP Right Cessation
- 1988-07-13 PH PH37219A patent/PH25958A/en unknown
- 1988-07-13 DE DE3851584T patent/DE3851584T2/de not_active Expired - Fee Related
- 1988-07-13 JP JP63172808A patent/JP2672980B2/ja not_active Expired - Fee Related
- 1988-07-13 ES ES88111224T patent/ES2063747T3/es not_active Expired - Lifetime
- 1988-07-13 AT AT88111224T patent/ATE111908T1/de not_active IP Right Cessation
- 1988-07-13 EP EP88111224A patent/EP0299457B1/de not_active Expired - Lifetime
- 1988-07-13 PT PT87975A patent/PT87975B/pt not_active IP Right Cessation
- 1988-07-14 KR KR1019880008717A patent/KR970011580B1/ko not_active Expired - Fee Related
- 1988-07-14 CN CN88104422A patent/CN1031084A/zh active Pending

Also Published As

Publication number	Publication date
FI91256C (fi)	1994-06-10
EP0299457B1 (de)	1994-09-21
CN1031084A (zh)	1989-02-15
JP2672980B2 (ja)	1997-11-05
EP0299457A2 (de)	1989-01-18
FI91256B (fi)	1994-02-28
DK388488A (da)	1989-01-15
NO170886B (no)	1992-09-14
DE3851584T2 (de)	1995-01-26
DE3851584D1 (de)	1994-10-27
AU1857788A (en)	1989-01-19
ATE111908T1 (de)	1994-10-15
ES2063747T3 (es)	1995-01-16
FI883300A0 (fi)	1988-07-11
NO883100L (no)	1989-01-16
EP0299457A3 (en)	1989-07-19
IE881879L (en)	1989-01-14
DK175933B1 (da)	2005-07-18
PT87975B (pt)	1995-03-01
NO170886C (no)	1992-12-23
FI883300L (fi)	1989-01-15
KR970011580B1 (ko)	1997-07-12
NZ225378A (en)	1992-03-26
JPH01110682A (ja)	1989-04-27
AU605070B2 (en)	1991-01-03
CA1330562C (en)	1994-07-05
NO883100D0 (no)	1988-07-12
IE64995B1 (en)	1995-09-20
DK388488D0 (da)	1988-07-12
PT87975A (pt)	1989-06-30
KR890002129A (ko)	1989-04-08

Publication	Publication Date	Title
US4703053A (en)	1987-10-27	Benzothiophenes and benzofurans and antiallergic use thereof
EP0299457B1 (de)	1994-09-21	Gegen Allergie wirkende Benzothiophene und neue und andere ausgewählte Benzothiophene, beide mit Wirkung zur Behandlung von akuten Atmungsangstanzeichen
Connor et al.	1992	Novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles as potential antiallergy agents
BG60347B2 (bg)	1994-09-30	Метод за получаване на 3-заместени 2-оксиндол-1-карбоксамиди
US5684002A (en)	1997-11-04	Dihydorbenzofuran and related compounds useful as anti-inflammatory agents
JP2002514638A (ja)	2002-05-21	インスリン抵抗性および高血糖症の治療に有用な１１−アリール−ベンゾ［ｂ］ナフト［２，３−ｄ］フラン類および１１−アリール−ベンゾ［ｂ］ナフト［２，３−ｄ］チオフェン類
EP0187487B1 (de)	1990-08-29	Gegen Allergie wirkende Benzothiophene und Benzofurane
US4910317A (en)	1990-03-20	Benzofurans and benzothiophenes having antiallergic activity and method of use thereof
KR20010102543A (ko)	2001-11-15	항바이러스제로서의4-옥소-4,7-디히드로-티에노[2,3-ｂ]피리딘-5-카르복스아미드
WO1994006789A1 (en)	1994-03-31	Serotonin receptor agents
US4931459A (en)	1990-06-05	Method for treating acute respirator distress syndrome
US5116854A (en)	1992-05-26	Anti-inflammatory 1-heteroaryl-3-acyl-2-oxindoles
US4663344A (en)	1987-05-05	Anti-inflammatory and analgesic 3-hydroxybenzo[b]thiophene derivatives, compositions, and method of use therefor
JPH10298180A (ja)	1998-11-10	ドーパミン受容体拮抗作用を有する化合物
FI80270B (fi)	1990-01-31	Foerfarande foer framstaellning av analgetiska och anti-inflammatoriska 1,3-diacyl-2-oxoindol-foereningar och mellanprodukter.
DK175445B1 (da)	2004-10-25	Anvendelse af benzothiophener ved fremstilling af lægemidler til behandling af akut respiratorisk distress syndrom
NO178496B (no)	1996-01-02	Kinolin-2-yl-metoksybenzylhydroksyurea
IE902836A1 (en)	1991-03-27	Substituted dibenzofurans and methods of using same
AU616336B2 (en)	1991-10-24	Anti-inflammatory 1-heteroaryl-3-acyl-2-oxindoles
JPS61171479A (ja)	1986-08-02	新規なベンゾチオフェン
JPH08208645A (ja)	1996-08-13	キノリン誘導体
JPS62273977A (ja)	1987-11-28	フリルチアゾ−ル化合物
JPH10182546A (ja)	1998-07-07	アズレン誘導体およびその製造方法並びにそれを含有する薬剤