IL126558A - Benzofuran carboxamides and pharmaceutical compositions containing them - Google Patents
Benzofuran carboxamides and pharmaceutical compositions containing themInfo
- Publication number
- IL126558A IL126558A IL12655897A IL12655897A IL126558A IL 126558 A IL126558 A IL 126558A IL 12655897 A IL12655897 A IL 12655897A IL 12655897 A IL12655897 A IL 12655897A IL 126558 A IL126558 A IL 126558A
- Authority
- IL
- Israel
- Prior art keywords
- methoxy
- alkyl
- acetyl
- compound
- aryl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- QHKJIJXBJCOABP-UHFFFAOYSA-N 1-benzofuran-2-carboxamide Chemical class C1=CC=C2OC(C(=O)N)=CC2=C1 QHKJIJXBJCOABP-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- -1 CO2R10 Chemical group 0.000 claims abstract description 39
- 125000003118 aryl group Chemical group 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 26
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 6
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 6
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims abstract description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 6
- 125000004470 heterocyclooxy group Chemical group 0.000 claims abstract description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 4
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims abstract description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 7
- 239000000203 mixture Substances 0.000 claims description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 201000010099 disease Diseases 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 102000018594 Tumour necrosis factor Human genes 0.000 claims description 17
- 108050007852 Tumour necrosis factor Proteins 0.000 claims description 17
- 230000005764 inhibitory process Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 206010003246 arthritis Diseases 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 5
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 5
- 206010040070 Septic Shock Diseases 0.000 claims description 5
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 5
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 5
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 5
- 201000008937 atopic dermatitis Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 4
- 206010017533 Fungal infection Diseases 0.000 claims description 4
- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 206010006451 bronchitis Diseases 0.000 claims description 3
- 230000002490 cerebral effect Effects 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000018937 joint inflammation Diseases 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000002685 pulmonary effect Effects 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 206010014824 Endotoxic shock Diseases 0.000 claims description 2
- 206010018367 Glomerulonephritis chronic Diseases 0.000 claims description 2
- 208000010496 Heart Arrest Diseases 0.000 claims description 2
- 206010019617 Henoch-Schonlein purpura Diseases 0.000 claims description 2
- 208000031814 IgA Vasculitis Diseases 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 206010022562 Intermittent claudication Diseases 0.000 claims description 2
- 206010069698 Langerhans' cell histiocytosis Diseases 0.000 claims description 2
- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims description 2
- 208000031888 Mycoses Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 2
- 208000024780 Urticaria Diseases 0.000 claims description 2
- 201000004810 Vascular dementia Diseases 0.000 claims description 2
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims description 2
- 230000000202 analgesic effect Effects 0.000 claims description 2
- 230000000954 anitussive effect Effects 0.000 claims description 2
- 230000003070 anti-hyperalgesia Effects 0.000 claims description 2
- 229940124584 antitussives Drugs 0.000 claims description 2
- 230000002917 arthritic effect Effects 0.000 claims description 2
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 2
- 208000010668 atopic eczema Diseases 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 201000010064 diabetes insipidus Diseases 0.000 claims description 2
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000003401 eosinophilic granuloma Diseases 0.000 claims description 2
- 208000015446 immunoglobulin a vasculitis Diseases 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 2
- 230000007794 irritation Effects 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 206010027175 memory impairment Diseases 0.000 claims description 2
- 201000008383 nephritis Diseases 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 230000036303 septic shock Effects 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 201000005539 vernal conjunctivitis Diseases 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims 4
- 210000003979 eosinophil Anatomy 0.000 claims 2
- 201000003651 pulmonary sarcoidosis Diseases 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 206010063094 Cerebral malaria Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 206010020649 Hyperkeratosis Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000001126 Keratosis Diseases 0.000 claims 1
- 208000000112 Myalgia Diseases 0.000 claims 1
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 238000009825 accumulation Methods 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 208000019664 bone resorption disease Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 230000001272 neurogenic effect Effects 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 4
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 328
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 182
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 164
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
- 235000019439 ethyl acetate Nutrition 0.000 description 110
- 239000007787 solid Substances 0.000 description 89
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 64
- 238000000746 purification Methods 0.000 description 47
- 238000000034 method Methods 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000000377 silicon dioxide Substances 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- LSMORADTGBFWAQ-UHFFFAOYSA-N 2-acetyl-7-methoxy-1-benzofuran-4-carbonyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C2=C1OC(C(C)=O)=C2 LSMORADTGBFWAQ-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000003818 flash chromatography Methods 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- 235000002639 sodium chloride Nutrition 0.000 description 21
- IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000012298 atmosphere Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- 239000000725 suspension Substances 0.000 description 12
- 239000000284 extract Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 239000006071 cream Substances 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- RLTXWMWRKDTNCD-UHFFFAOYSA-N 2-ethyl-7-methoxy-1-benzofuran-4-carbonyl chloride Chemical compound C1=CC(OC)=C2OC(CC)=CC2=C1C(Cl)=O RLTXWMWRKDTNCD-UHFFFAOYSA-N 0.000 description 7
- 241000700605 Viruses Species 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 150000003857 carboxamides Chemical class 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 5
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 5
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- 239000000843 powder Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000001665 trituration Methods 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- ISIQAMHROGZHOV-UHFFFAOYSA-N 3,5-dichloropyridin-4-amine Chemical compound NC1=C(Cl)C=NC=C1Cl ISIQAMHROGZHOV-UHFFFAOYSA-N 0.000 description 3
- ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 3
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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- 238000002965 ELISA Methods 0.000 description 3
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- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
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- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
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Classifications
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
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- 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
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Communicable Diseases (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9610515.0A GB9610515D0 (en) | 1996-05-20 | 1996-05-20 | Novel compounds |
| PCT/GB1996/003012 WO1997020833A1 (en) | 1995-12-05 | 1996-12-05 | Benzofuran carboxamides and sulphonamides |
| GBGB9708070.9A GB9708070D0 (en) | 1997-04-22 | 1997-04-22 | Compounds |
| PCT/GB1997/001361 WO1997044337A1 (en) | 1996-05-20 | 1997-05-20 | Benzofuran carboxamides and their therapeutic use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL126558A0 IL126558A0 (en) | 1999-08-17 |
| IL126558A true IL126558A (en) | 2002-07-25 |
Family
ID=26309366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12655897A IL126558A (en) | 1996-05-20 | 1997-05-20 | Benzofuran carboxamides and pharmaceutical compositions containing them |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US5972936A (OSRAM) |
| EP (1) | EP0901482B1 (OSRAM) |
| JP (1) | JP2000510848A (OSRAM) |
| CN (1) | CN1219171A (OSRAM) |
| AT (1) | ATE239004T1 (OSRAM) |
| BR (1) | BR9709113A (OSRAM) |
| CA (1) | CA2252537A1 (OSRAM) |
| CZ (1) | CZ371998A3 (OSRAM) |
| DE (1) | DE69721526T2 (OSRAM) |
| ES (1) | ES2193376T3 (OSRAM) |
| HU (1) | HUP0100042A3 (OSRAM) |
| IL (1) | IL126558A (OSRAM) |
| NO (1) | NO985375L (OSRAM) |
| NZ (1) | NZ332340A (OSRAM) |
| PL (1) | PL329912A1 (OSRAM) |
| RU (1) | RU2162467C2 (OSRAM) |
| SK (1) | SK282676B6 (OSRAM) |
| TR (1) | TR199802386T2 (OSRAM) |
| WO (1) | WO1997044337A1 (OSRAM) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE215540T1 (de) * | 1995-12-05 | 2002-04-15 | Darwin Discovery Ltd | Benzofuran-carboxamide und -sulfonamide |
| EP0923568B9 (en) * | 1996-08-19 | 2003-08-13 | ALTANA Pharma AG | Novel benzofuran-4-carboxamides |
| ATE237612T1 (de) * | 1997-10-01 | 2003-05-15 | Kyowa Hakko Kogyo Kk | Benzofuranderivate |
| JP2002502851A (ja) * | 1998-02-09 | 2002-01-29 | ダーウィン・ディスカバリー・リミテッド | ベンゾフラン−４−カルボキサミドとその治療的使用 |
| WO1999058533A1 (en) * | 1998-05-08 | 1999-11-18 | Smithkline Beecham Plc | Phenylurea and phenylthio urea derivatives |
| TW555759B (en) * | 1998-06-08 | 2003-10-01 | Darwin Discovery Ltd | Heterocyclic compounds and their therapeutic use |
| US7217722B2 (en) | 2000-02-01 | 2007-05-15 | Kirin Beer Kabushiki Kaisha | Nitrogen-containing compounds having kinase inhibitory activity and drugs containing the same |
| GB0003257D0 (en) | 2000-02-11 | 2000-04-05 | Darwin Discovery Ltd | Heterocyclic compounds and their therapeutic use |
| AU2001277731A1 (en) * | 2000-08-09 | 2002-02-18 | Welfide Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| US6953774B2 (en) | 2000-08-11 | 2005-10-11 | Applied Research Systems Ars Holding N.V. | Methods of inducing ovulation |
| JP4532115B2 (ja) | 2001-12-14 | 2010-08-25 | メルク セローノ ソシエテ アノニム | 非ポリペプチドｃＡＭＰレベル調節剤を使用する排卵誘発方法 |
| ES2336905T3 (es) * | 2002-03-28 | 2010-04-19 | Mitsubishi Tanabe Pharma Corporation | Derivado de benzofurano. |
| AU2003225048A1 (en) * | 2002-04-19 | 2003-11-03 | Integrated Magnetoelectronics Corporation | Interfaces between semiconductor circuitry and transpinnor-based circuitry |
| ES2195785B1 (es) * | 2002-05-16 | 2005-03-16 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| DE10238257B4 (de) * | 2002-08-21 | 2007-04-19 | Johannes-Gutenberg-Universität Mainz | Sorbicillacton A und Sorbicillacton-A-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
| US20050215626A1 (en) * | 2003-09-25 | 2005-09-29 | Wyeth | Substituted benzofuran oximes |
| TW200524915A (en) * | 2003-09-26 | 2005-08-01 | Tanabe Seiyaku Co | Carbamoyl-type benzofuran derivatives |
| ES2251866B1 (es) * | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| ES2251867B1 (es) * | 2004-06-21 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| US20100130737A1 (en) * | 2005-02-18 | 2010-05-27 | Takeda Pharmaceutical Company Limited | Regulating Agent of GPR34 Receptor Function |
| US7678363B2 (en) | 2005-08-26 | 2010-03-16 | Braincells Inc | Methods of treating psychiatric conditions comprising administration of muscarinic agents in combination with SSRIs |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| WO2007047978A2 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| AU2006308889A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | GABA receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| US7842713B2 (en) * | 2006-04-20 | 2010-11-30 | Pfizer Inc | Fused phenyl amido heterocyclic compounds |
| CA2651813A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| JP5682051B2 (ja) | 2006-05-18 | 2015-03-11 | ファーマサイクリックス，インク． | 細胞内キナーゼ阻害剤 |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| CN100434426C (zh) * | 2006-10-10 | 2008-11-19 | 中国科学院昆明植物研究所 | 盐肤木内酯a,其制备方法和其在制药中的应用 |
| ZA200905371B (en) * | 2007-02-28 | 2010-10-27 | Leo Pharma As | Novel phosphodiesterase Inhibitors |
| RS53407B (sr) | 2007-02-28 | 2014-10-31 | Leo Pharma A/S | Novi inhibitori fosfodiesteraze |
| ES2320954B1 (es) * | 2007-03-02 | 2010-03-16 | Laboratorio Almirall S.A. | Nuevo procedimiento de preparacion de 3-metil-4-fenilisoxazolo (3,4-d)iridazin-7(6h)-ona. |
| KR100752613B1 (ko) * | 2007-05-02 | 2007-08-29 | 우석대학교 산학협력단 | 신규 벤조푸란 유도체를 포함하는 부정맥 예방용 식품 |
| TWI444379B (zh) | 2007-06-29 | 2014-07-11 | Sunesis Pharmaceuticals Inc | 有用於作為Ｒａｆ激酶抑制劑之化合物 |
| EA201100311A1 (ru) | 2008-09-11 | 2011-10-31 | Пфайзер Инк. | Амидные производные гетероарилов и их применение в качестве активаторов глюкокиназы |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| EP2604604A1 (en) * | 2009-03-11 | 2013-06-19 | Pfizer Inc | Benzofuranyl derivatives used as glucokinase inhibitors |
| CN102958937B (zh) * | 2010-06-24 | 2016-03-30 | 利奥制药有限公司 | 作为磷酸二酯酶抑制剂的苯并二氧杂环戊烯或苯并二氧杂环庚烯杂环化合物 |
| CN102010405B (zh) * | 2010-11-08 | 2012-07-25 | 湖南大学 | 4-(苯并呋喃-5-基)-2-苄亚氨基噻唑及其作为抗肿瘤药物的应用 |
| WO2013106547A1 (en) | 2012-01-10 | 2013-07-18 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| EP3597186B1 (en) | 2015-01-05 | 2021-12-08 | The U.S.A. as represented by the Secretary, Department of Health and Human Services | Myc g-quadruplex stabilizing small molecules and their use |
| JPWO2020246418A1 (OSRAM) * | 2019-06-04 | 2020-12-10 | ||
| GB202306662D0 (en) | 2023-05-05 | 2023-06-21 | Union Therapeutics As | Dosage regimen |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4666931A (en) * | 1984-12-29 | 1987-05-19 | Kaken Pharmaceutical Co., Ltd. | Benzofuran derivatives useful in treating diabetic complications |
| WO1992003427A1 (fr) * | 1990-08-17 | 1992-03-05 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose de cetone et remede pour l'osteoporose |
| ATE188379T1 (de) * | 1992-10-14 | 2000-01-15 | Merck & Co Inc | Fibrinogenrezeptor-antagonisten |
| GB9309324D0 (en) * | 1993-05-06 | 1993-06-16 | Bayer Ag | Venzofuranyl-and-thiophenyl-alkanecarboxyclic acids derivatives |
| ATE180780T1 (de) * | 1993-08-05 | 1999-06-15 | Hoechst Marion Roussel Inc | 2-(piperidin-4-yl, pyridin-4-yl und tetrahydropyridin-4-yl)-benzofuran-7-carbamat derivate, ihre herstellung und verwendung als acetylcholinesterase inhibitoren |
| EP0685475B1 (en) * | 1994-05-31 | 1999-01-13 | Bayer Ag | Amino-benzofuryl-and thienyl-derivatives |
| DE59508773D1 (de) * | 1994-07-22 | 2000-11-09 | Byk Gulden Lomberg Chem Fab | Dihydrobenzofurane |
| WO1996036596A1 (en) * | 1995-05-19 | 1996-11-21 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
| WO1996036595A1 (en) * | 1995-05-19 | 1996-11-21 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
| JPH10147585A (ja) * | 1996-11-19 | 1998-06-02 | Kyowa Hakko Kogyo Co Ltd | 含酸素複素環化合物 |
| AU5772196A (en) * | 1995-05-19 | 1996-11-29 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
| CN1163493C (zh) * | 1995-05-19 | 2004-08-25 | 协和发酵工业株式会社 | 含氧杂环化合物 |
| ATE215540T1 (de) * | 1995-12-05 | 2002-04-15 | Darwin Discovery Ltd | Benzofuran-carboxamide und -sulfonamide |
| EP0923568B9 (en) * | 1996-08-19 | 2003-08-13 | ALTANA Pharma AG | Novel benzofuran-4-carboxamides |
-
1997
- 1997-05-20 CZ CZ983719A patent/CZ371998A3/cs unknown
- 1997-05-20 TR TR1998/02386T patent/TR199802386T2/xx unknown
- 1997-05-20 EP EP97923193A patent/EP0901482B1/en not_active Expired - Lifetime
- 1997-05-20 US US08/859,510 patent/US5972936A/en not_active Expired - Fee Related
- 1997-05-20 CA CA002252537A patent/CA2252537A1/en not_active Abandoned
- 1997-05-20 NZ NZ332340A patent/NZ332340A/xx unknown
- 1997-05-20 CN CN97194736A patent/CN1219171A/zh active Pending
- 1997-05-20 AT AT97923193T patent/ATE239004T1/de not_active IP Right Cessation
- 1997-05-20 ES ES97923193T patent/ES2193376T3/es not_active Expired - Lifetime
- 1997-05-20 IL IL12655897A patent/IL126558A/en not_active IP Right Cessation
- 1997-05-20 PL PL97329912A patent/PL329912A1/xx unknown
- 1997-05-20 DE DE69721526T patent/DE69721526T2/de not_active Expired - Fee Related
- 1997-05-20 US US08/859,509 patent/US5925636A/en not_active Expired - Fee Related
- 1997-05-20 SK SK1604-98A patent/SK282676B6/sk unknown
- 1997-05-20 JP JP09541240A patent/JP2000510848A/ja not_active Ceased
- 1997-05-20 RU RU98123097/04A patent/RU2162467C2/ru not_active IP Right Cessation
- 1997-05-20 WO PCT/GB1997/001361 patent/WO1997044337A1/en not_active Ceased
- 1997-05-20 HU HU0100042A patent/HUP0100042A3/hu unknown
- 1997-05-20 BR BR9709113A patent/BR9709113A/pt active Search and Examination
-
1998
- 1998-11-19 NO NO985375A patent/NO985375L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SK160498A3 (en) | 1999-06-11 |
| SK282676B6 (sk) | 2002-11-06 |
| NO985375D0 (no) | 1998-11-19 |
| NO985375L (no) | 1998-11-19 |
| CA2252537A1 (en) | 1997-11-27 |
| EP0901482A1 (en) | 1999-03-17 |
| WO1997044337A1 (en) | 1997-11-27 |
| US5972936A (en) | 1999-10-26 |
| HUP0100042A3 (en) | 2003-01-28 |
| US5925636A (en) | 1999-07-20 |
| HUP0100042A2 (hu) | 2002-01-28 |
| EP0901482B1 (en) | 2003-05-02 |
| CN1219171A (zh) | 1999-06-09 |
| ATE239004T1 (de) | 2003-05-15 |
| RU2162467C2 (ru) | 2001-01-27 |
| DE69721526D1 (de) | 2003-06-05 |
| NZ332340A (en) | 2000-04-28 |
| BR9709113A (pt) | 1999-08-03 |
| ES2193376T3 (es) | 2003-11-01 |
| JP2000510848A (ja) | 2000-08-22 |
| PL329912A1 (en) | 1999-04-26 |
| IL126558A0 (en) | 1999-08-17 |
| TR199802386T2 (xx) | 1999-02-22 |
| DE69721526T2 (de) | 2004-04-08 |
| CZ371998A3 (cs) | 1999-03-17 |
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| Date | Code | Title | Description |
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| FF | Patent granted | ||
| KB | Patent renewed | ||
| RH1 | Patent not in force |