IL126558A - Benzofuran carboxamides and pharmaceutical compositions containing them - Google Patents

Benzofuran carboxamides and pharmaceutical compositions containing them

Info

Publication number: IL126558A
Authority: IL; Israel
Prior art keywords: methoxy; alkyl; acetyl; compound; aryl
Prior art date: 1996-05-20

Application number

IL12655897A

Other languages

English (en)

Other versions

IL126558A0 (en

Original Assignee

Darwin Discovery Ltd

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.)

1996-05-20

Filing date

1997-05-20

Publication date

2002-07-25

1996-05-20 Priority claimed from GBGB9610515.0A external-priority patent/GB9610515D0/en

1996-12-05 Priority claimed from PCT/GB1996/003012 external-priority patent/WO1997020833A1/en

1997-04-22 Priority claimed from GBGB9708070.9A external-priority patent/GB9708070D0/en

1997-05-20 Application filed by Darwin Discovery Ltd filed Critical Darwin Discovery Ltd

1999-08-17 Publication of IL126558A0 publication Critical patent/IL126558A0/xx

2002-07-25 Publication of IL126558A publication Critical patent/IL126558A/en

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
235000019441 ethanol Nutrition 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000003981 vehicle Substances 0.000 description 6
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
125000004429 atom Chemical group 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 5
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
241000124008 Mammalia Species 0.000 description 4
239000002158 endotoxin Substances 0.000 description 4
239000000499 gel Substances 0.000 description 4
230000001404 mediated effect Effects 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
230000009466 transformation Effects 0.000 description 4
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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
238000002965 ELISA Methods 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
102000004083 Lymphotoxin-alpha Human genes 0.000 description 3
108090000542 Lymphotoxin-alpha Proteins 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000003556 assay Methods 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
150000001907 coumarones Chemical class 0.000 description 3
229960004979 fampridine Drugs 0.000 description 3
238000011049 filling Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
125000004356 hydroxy functional group Chemical group O* 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
229920006008 lipopolysaccharide Polymers 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000006210 lotion Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000002950 monocyclic group Chemical group 0.000 description 3
239000002674 ointment Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
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
239000000600 sorbitol Substances 0.000 description 3
235000010356 sorbitol Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
239000003826 tablet Substances 0.000 description 3
239000012049 topical pharmaceutical composition Substances 0.000 description 3
238000000844 transformation Methods 0.000 description 3
230000006433 tumor necrosis factor production Effects 0.000 description 3
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
ADLUEUKLEVZUKP-UHFFFAOYSA-N (4-nitrophenyl) 2-ethyl-7-methoxy-1-benzofuran-4-carboxylate Chemical compound C1=CC(OC)=C2OC(CC)=CC2=C1C(=O)OC1=CC=C([N+]([O-])=O)C=C1 ADLUEUKLEVZUKP-UHFFFAOYSA-N 0.000 description 2
SQOGUSCBWCVSQC-UHFFFAOYSA-N 1-(4-bromo-7-methoxy-1-benzofuran-2-yl)ethanone Chemical compound COC1=CC=C(Br)C2=C1OC(C(C)=O)=C2 SQOGUSCBWCVSQC-UHFFFAOYSA-N 0.000 description 2
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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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
- 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
- A61P11/16—Central respiratory analeptics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C07D307/86—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)

IL12655897A 1996-05-20 1997-05-20 Benzofuran carboxamides and pharmaceutical compositions containing them IL126558A (en)

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)	US5925636A (th)
EP (1)	EP0901482B1 (th)
JP (1)	JP2000510848A (th)
CN (1)	CN1219171A (th)
AT (1)	ATE239004T1 (th)
BR (1)	BR9709113A (th)
CA (1)	CA2252537A1 (th)
CZ (1)	CZ371998A3 (th)
DE (1)	DE69721526T2 (th)
ES (1)	ES2193376T3 (th)
HU (1)	HUP0100042A3 (th)
IL (1)	IL126558A (th)
NO (1)	NO985375D0 (th)
NZ (1)	NZ332340A (th)
PL (1)	PL329912A1 (th)
RU (1)	RU2162467C2 (th)
SK (1)	SK282676B6 (th)
TR (1)	TR199802386T2 (th)
WO (1)	WO1997044337A1 (th)

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KR100752613B1 (ko) *	2007-05-02	2007-08-29	우석대학교 산학협력단	신규 벤조푸란 유도체를 포함하는 부정맥 예방용 식품
CL2008001933A1 (es)	2007-06-29	2009-09-25	Millennium Pharm Inc	Compuestos derivados de pirimidina, inhibidores de la raf quinasa; compuestos intermediarios; procedimiento de preparacion; composicion farmaceutica; y su uso para tratar trastornos proliferativos, cardiacos, neurodegenerativos, inflamatorios, oseos, inmunologicos enfermedad viral, entre otros.
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1997
- 1997-05-20 HU HU0100042A patent/HUP0100042A3/hu unknown
- 1997-05-20 AT AT97923193T patent/ATE239004T1/de not_active IP Right Cessation
- 1997-05-20 BR BR9709113A patent/BR9709113A/pt active Search and Examination
- 1997-05-20 RU RU98123097/04A patent/RU2162467C2/ru not_active IP Right Cessation
- 1997-05-20 PL PL97329912A patent/PL329912A1/xx unknown
- 1997-05-20 CN CN97194736A patent/CN1219171A/zh active Pending
- 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 WO PCT/GB1997/001361 patent/WO1997044337A1/en not_active Ceased
- 1997-05-20 US US08/859,510 patent/US5972936A/en not_active Expired - Fee Related
- 1997-05-20 DE DE69721526T patent/DE69721526T2/de not_active Expired - Fee Related
- 1997-05-20 CZ CZ983719A patent/CZ371998A3/cs unknown
- 1997-05-20 TR TR1998/02386T patent/TR199802386T2/xx unknown
- 1997-05-20 ES ES97923193T patent/ES2193376T3/es not_active Expired - Lifetime
- 1997-05-20 CA CA002252537A patent/CA2252537A1/en not_active Abandoned
- 1997-05-20 EP EP97923193A patent/EP0901482B1/en not_active Expired - Lifetime
- 1997-05-20 NZ NZ332340A patent/NZ332340A/xx unknown
- 1997-05-20 JP JP09541240A patent/JP2000510848A/ja not_active Ceased
- 1997-05-20 IL IL12655897A patent/IL126558A/en not_active IP Right Cessation
1998
- 1998-11-19 NO NO985375A patent/NO985375D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE69721526T2 (de)	2004-04-08
TR199802386T2 (xx)	1999-02-22
CA2252537A1 (en)	1997-11-27
NZ332340A (en)	2000-04-28
ES2193376T3 (es)	2003-11-01
SK282676B6 (sk)	2002-11-06
US5925636A (en)	1999-07-20
JP2000510848A (ja)	2000-08-22
CZ371998A3 (cs)	1999-03-17
NO985375L (no)	1998-11-19
US5972936A (en)	1999-10-26
HUP0100042A3 (en)	2003-01-28
HUP0100042A2 (hu)	2002-01-28
RU2162467C2 (ru)	2001-01-27
IL126558A0 (en)	1999-08-17
DE69721526D1 (de)	2003-06-05
ATE239004T1 (de)	2003-05-15
SK160498A3 (en)	1999-06-11
NO985375D0 (no)	1998-11-19
EP0901482A1 (en)	1999-03-17
PL329912A1 (en)	1999-04-26
CN1219171A (zh)	1999-06-09
BR9709113A (pt)	1999-08-03
WO1997044337A1 (en)	1997-11-27
EP0901482B1 (en)	2003-05-02

Legal Events

Date	Code	Title
2003-01-12	FF	Patent granted
2003-03-12	KB	Patent renewed
2004-02-08	RH1	Patent not in force

Publication	Publication Date	Title
EP0901482B1 (en)	2003-05-02	Benzofuran carboxamides and their therapeutic use
US5804588A (en)	1998-09-08	Quinoline carboxanides and their therapeutic use
US6069151A (en)	2000-05-30	Quinolines and their therapeutic use
CA2238376C (en)	2006-08-15	Benzofuran carboxamides and sulphonamides
AU726590B2 (en)	2000-11-09	Bicyclic aryl carboxamides and their therapeutic use
AU711587B2 (en)	1999-10-14	Quinolines and their therapeutic use
CA2662274A1 (en)	2008-03-06	Chemical compounds
US6403791B1 (en)	2002-06-11	Heterocyclic compounds and their therapeutic use
ES2204171T3 (es)	2004-04-16	Derivados de furopiridina y su utilizacion terapeutica.
WO2019085978A1 (zh)	2019-05-09	杂芳基酰胺类化合物、其制备方法、药用组合物及其应用
US6066657A (en)	2000-05-23	Benzofuran-4-carboxamides and their therapeutic use
US20010031777A1 (en)	2001-10-18	Heterocyclic compounds and their therapeutic use
AU765350B2 (en)	2003-09-18	Benzofuran carboxamides and their therapeutic use
SE531698C2 (sv)	2009-07-07	Nya bronkdilaterande a,b-omättade amider
KR20000011120A (ko)	2000-02-25	벤조퓨란카르복사미드 및 이들의 치료학적 용도
MXPA98004466A (es)	1999-02-01	Carboxamidas y sulfonamidas de benzofurano
MXPA00007632A (es)	2002-02-26	Benzofuran-4-carboxamidas y su uso terapeutico