SK282979B6 - Benzopyránové deriváty, spôsob ich prípravy a ich použitie - Google Patents

Benzopyránové deriváty, spôsob ich prípravy a ich použitie Download PDF

Info

Publication number: SK282979B6
Authority: SK; Slovakia
Prior art keywords: benzopyran; phenyl; oxo; group; tetrazolyl
Prior art date: 1996-03-21

Application number

SK1272-98A

Other languages

English (en)

Slovak (sk)

Other versions

SK127298A3 (en

Inventor

Germano Carganico

Casellas David Mauleon

Avellana Jaime Pascual

Perez Ma Luisa Garcia

Benet Albert Palomer

Original Assignee

Laboratorios Menarini S.A.

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.)

1996-03-21

Filing date

1997-03-20

Publication date

2003-01-09

1997-03-20 Application filed by Laboratorios Menarini S.A. filed Critical Laboratorios Menarini S.A.

1999-03-12 Publication of SK127298A3 publication Critical patent/SK127298A3/sk

2003-01-09 Publication of SK282979B6 publication Critical patent/SK282979B6/sk

Links

150000001562 benzopyrans Chemical class 0.000 title claims abstract description 21
230000009471 action Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 201
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 78
-1 5-tetrazolyl Chemical group 0.000 claims abstract description 73
239000001257 hydrogen Substances 0.000 claims abstract description 36
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 29
229910052760 oxygen Inorganic materials 0.000 claims abstract description 28
239000001301 oxygen Substances 0.000 claims abstract description 24
229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
125000004434 sulfur atom Chemical group 0.000 claims abstract description 10
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
239000003814 drug Substances 0.000 claims abstract description 3
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 154
239000000203 mixture Substances 0.000 claims description 110
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
125000003836 4-phenylbutoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 24
239000007858 starting material Substances 0.000 claims description 23
125000001424 substituent group Chemical group 0.000 claims description 21
239000000126 substance Substances 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
150000002431 hydrogen Chemical class 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 12
230000008569 process Effects 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 9
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 7
125000005228 aryl sulfonate group Chemical group 0.000 claims description 7
150000002617 leukotrienes Chemical class 0.000 claims description 7
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
YCRQAZRQPAEIIE-UHFFFAOYSA-N 4-oxo-8-[[4-(4-phenylbutoxy)phenyl]sulfonylamino]chromene-2-carboxylic acid Chemical compound C=12OC(C(=O)O)=CC(=O)C2=CC=CC=1NS(=O)(=O)C(C=C1)=CC=C1OCCCCC1=CC=CC=C1 YCRQAZRQPAEIIE-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
208000010668 atopic eczema Diseases 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
206010002198 Anaphylactic reaction Diseases 0.000 claims description 3
206010003225 Arteriospasm coronary Diseases 0.000 claims description 3
206010048962 Brain oedema Diseases 0.000 claims description 3
206010014824 Endotoxic shock Diseases 0.000 claims description 3
201000004681 Psoriasis Diseases 0.000 claims description 3
206010039085 Rhinitis allergic Diseases 0.000 claims description 3
206010040070 Septic Shock Diseases 0.000 claims description 3
230000000172 allergic effect Effects 0.000 claims description 3
201000010105 allergic rhinitis Diseases 0.000 claims description 3
230000036783 anaphylactic response Effects 0.000 claims description 3
208000003455 anaphylaxis Diseases 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
208000006752 brain edema Diseases 0.000 claims description 3
230000000747 cardiac effect Effects 0.000 claims description 3
230000002757 inflammatory effect Effects 0.000 claims description 3
208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 3
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims description 3
239000012453 solvate Substances 0.000 claims description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
206010006811 Bursitis Diseases 0.000 claims description 2
206010010744 Conjunctivitis allergic Diseases 0.000 claims description 2
208000000491 Tendinopathy Diseases 0.000 claims description 2
206010043255 Tendonitis Diseases 0.000 claims description 2
208000002205 allergic conjunctivitis Diseases 0.000 claims description 2
208000024998 atopic conjunctivitis Diseases 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
208000027866 inflammatory disease Diseases 0.000 claims description 2
239000003456 ion exchange resin Substances 0.000 claims description 2
229920003303 ion-exchange polymer Polymers 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
208000010125 myocardial infarction Diseases 0.000 claims description 2
208000031225 myocardial ischemia Diseases 0.000 claims description 2
201000008482 osteoarthritis Diseases 0.000 claims description 2
206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
201000004415 tendinitis Diseases 0.000 claims description 2
230000001404 mediated effect Effects 0.000 claims 3
125000003831 tetrazolyl group Chemical group 0.000 claims 2
FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 claims 1
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
238000010306 acid treatment Methods 0.000 claims 1
208000026935 allergic disease Diseases 0.000 claims 1
230000002526 effect on cardiovascular system Effects 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 9
125000004430 oxygen atom Chemical group O* 0.000 abstract description 3
208000024172 Cardiovascular disease Diseases 0.000 abstract description 2
230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 150
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 106
239000002904 solvent Substances 0.000 description 83
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 78
239000000243 solution Substances 0.000 description 73
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 71
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
238000003756 stirring Methods 0.000 description 55
239000007787 solid Substances 0.000 description 52
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
239000003208 petroleum Substances 0.000 description 34
238000010898 silica gel chromatography Methods 0.000 description 34
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
239000000741 silica gel Substances 0.000 description 28
229910002027 silica gel Inorganic materials 0.000 description 28
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
238000004587 chromatography analysis Methods 0.000 description 25
239000012043 crude product Substances 0.000 description 22
238000002425 crystallisation Methods 0.000 description 18
230000008025 crystallization Effects 0.000 description 18
239000012074 organic phase Substances 0.000 description 18
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 17
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 15
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
239000002585 base Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 11
238000001035 drying Methods 0.000 description 10
NLLYXOVHEQVWJF-UHFFFAOYSA-N 1-(3-amino-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(N)=C1O NLLYXOVHEQVWJF-UHFFFAOYSA-N 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 8
PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 8
238000001914 filtration Methods 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000725 suspension Substances 0.000 description 8
239000002253 acid Substances 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
238000010828 elution Methods 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
238000001311 chemical methods and process Methods 0.000 description 5
230000029087 digestion Effects 0.000 description 5
239000000284 extract Substances 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
239000003199 leukotriene receptor blocking agent Substances 0.000 description 5
WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
239000012528 membrane Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
230000009467 reduction Effects 0.000 description 5
239000003039 volatile agent Substances 0.000 description 5
DQYRWJNQKAKWMV-UHFFFAOYSA-N 2-(3-phenylpropyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid Chemical compound C1C2=CC(C(=O)O)=CC=C2OC1CCCC1=CC=CC=C1 DQYRWJNQKAKWMV-UHFFFAOYSA-N 0.000 description 4
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
206010061218 Inflammation Diseases 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
238000007098 aminolysis reaction Methods 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
230000027455 binding Effects 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
150000003857 carboxamides Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
IMJURHISCVEIKS-UHFFFAOYSA-N ethyl 2-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2OC(CO)CC2=C1 IMJURHISCVEIKS-UHFFFAOYSA-N 0.000 description 4
230000004054 inflammatory process Effects 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 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
PTPNOHHWWIGMJD-UHFFFAOYSA-N 1-(2-hydroxy-3-iodophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(I)=C1O PTPNOHHWWIGMJD-UHFFFAOYSA-N 0.000 description 3
229940002520 2'-hydroxyacetophenone Drugs 0.000 description 3
JKKNUDQVTLXFOO-UHFFFAOYSA-N 2-(3-phenylpropyl)-3,4-dihydro-2h-chromene-6-carboxylic acid Chemical compound C1CC2=CC(C(=O)O)=CC=C2OC1CCCC1=CC=CC=C1 JKKNUDQVTLXFOO-UHFFFAOYSA-N 0.000 description 3
QAQWDJNVECEEGE-UHFFFAOYSA-N 2-(phenylmethoxymethyl)-3,4-dihydro-2h-chromene-6-carboxylic acid Chemical compound C1CC2=CC(C(=O)O)=CC=C2OC1COCC1=CC=CC=C1 QAQWDJNVECEEGE-UHFFFAOYSA-N 0.000 description 3
LDZLXQFDGRCELX-UHFFFAOYSA-N 4-phenylbutan-1-ol Chemical compound OCCCCC1=CC=CC=C1 LDZLXQFDGRCELX-UHFFFAOYSA-N 0.000 description 3
CLNIBJASCGZXHH-UHFFFAOYSA-N 70978-54-0 Chemical compound CC(=O)C1=CC(Br)=CC([N+]([O-])=O)=C1O CLNIBJASCGZXHH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
241000700199 Cavia porcellus Species 0.000 description 3
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JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
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ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
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238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 2
238000007239 Wittig reaction Methods 0.000 description 2
LHZYSSXZCPJSEL-UHFFFAOYSA-N [4-(4-phenylbutoxy)phenyl]methanol Chemical compound C1=CC(CO)=CC=C1OCCCCC1=CC=CC=C1 LHZYSSXZCPJSEL-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
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YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
210000000748 cardiovascular system Anatomy 0.000 description 2
230000003399 chemotactic effect Effects 0.000 description 2
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
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FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
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238000004821 distillation Methods 0.000 description 2
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MRLGNPBALHNAID-UHFFFAOYSA-N ethyl 2-(3-phenylpropyl)-2,3-dihydro-1-benzofuran-5-carboxylate Chemical compound C1C2=CC(C(=O)OCC)=CC=C2OC1CCCC1=CC=CC=C1 MRLGNPBALHNAID-UHFFFAOYSA-N 0.000 description 2
ZEBWSHGXUUDMAL-UHFFFAOYSA-N ethyl 2-(benzylsulfanylmethyl)-3h-1-benzofuran-2-carboxylate Chemical compound C1C2=CC=CC=C2OC1(C(=O)OCC)CSCC1=CC=CC=C1 ZEBWSHGXUUDMAL-UHFFFAOYSA-N 0.000 description 2
CRIAGSOTOGFTAN-UHFFFAOYSA-N ethyl 2-(phenylmethoxymethyl)-3h-1-benzofuran-2-carboxylate Chemical compound C1C2=CC=CC=C2OC1(C(=O)OCC)COCC1=CC=CC=C1 CRIAGSOTOGFTAN-UHFFFAOYSA-N 0.000 description 2
PSOZUQKKUGXCEN-UHFFFAOYSA-N ethyl 3,4-dihydro-2h-chromene-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OCC)CCC2=C1 PSOZUQKKUGXCEN-UHFFFAOYSA-N 0.000 description 2
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RWYRGJTXJBZSTH-UHFFFAOYSA-N ethyl 4-oxo-8-[[4-(4-phenylbutoxy)phenyl]methoxy]chromene-2-carboxylate Chemical compound C=12OC(C(=O)OCC)=CC(=O)C2=CC=CC=1OCC(C=C1)=CC=C1OCCCCC1=CC=CC=C1 RWYRGJTXJBZSTH-UHFFFAOYSA-N 0.000 description 2
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YYOJELXHNYZRCZ-UHFFFAOYSA-N ethyl 6-bromo-8-nitro-4-oxochromene-2-carboxylate Chemical compound BrC1=CC([N+]([O-])=O)=C2OC(C(=O)OCC)=CC(=O)C2=C1 YYOJELXHNYZRCZ-UHFFFAOYSA-N 0.000 description 2
DXHQVNGGHNWZEF-UHFFFAOYSA-N ethyl 7-chloro-2-(3-phenylpropyl)-2,3-dihydro-1-benzofuran-5-carboxylate Chemical compound O1C=2C(Cl)=CC(C(=O)OCC)=CC=2CC1CCCC1=CC=CC=C1 DXHQVNGGHNWZEF-UHFFFAOYSA-N 0.000 description 2
LBYAHPDCNXILBM-UHFFFAOYSA-N ethyl 7-chloro-2-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-carboxylate Chemical compound ClC1=CC(C(=O)OCC)=CC2=C1OC(CO)C2 LBYAHPDCNXILBM-UHFFFAOYSA-N 0.000 description 2
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125000004494 ethyl ester group Chemical group 0.000 description 2
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
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150000001299 aldehydes Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
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230000002052 anaphylactic effect Effects 0.000 description 1
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238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
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UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
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XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
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HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
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GECOLABOBGRIGY-UHFFFAOYSA-N ethyl 8-nitro-4-oxochromene-2-carboxylate Chemical compound C1=CC([N+]([O-])=O)=C2OC(C(=O)OCC)=CC(=O)C2=C1 GECOLABOBGRIGY-UHFFFAOYSA-N 0.000 description 1
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239000007789 gas Substances 0.000 description 1
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210000005003 heart tissue Anatomy 0.000 description 1
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238000006460 hydrolysis reaction Methods 0.000 description 1
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239000005457 ice water Substances 0.000 description 1
238000011534 incubation Methods 0.000 description 1
IENZCGNHSIMFJE-UHFFFAOYSA-N indole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC=CC2=C1 IENZCGNHSIMFJE-UHFFFAOYSA-N 0.000 description 1
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230000004968 inflammatory condition Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
OTZRAYGBFWZKMX-JUDRUQEKSA-N leukotriene E4 Chemical compound CCCCCC=CCC=C\C=C\C=C\[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O OTZRAYGBFWZKMX-JUDRUQEKSA-N 0.000 description 1
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NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
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239000002184 metal Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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ZSBIMTDWIGWJPW-UHFFFAOYSA-N methyl 3-chloro-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(Cl)=C1 ZSBIMTDWIGWJPW-UHFFFAOYSA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical class C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 description 1
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
IZXGZAJMDLJLMF-UHFFFAOYSA-N methylaminomethanol Chemical compound CNCO IZXGZAJMDLJLMF-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical class PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 description 1
230000003843 mucus production Effects 0.000 description 1
UUGGPISNCZNLTB-UHFFFAOYSA-N n-(2-cyano-4-oxochromen-8-yl)-2-(3-phenylpropyl)-2,3-dihydro-1-benzofuran-5-carboxamide Chemical compound C=1C=CC(C(C=C(O2)C#N)=O)=C2C=1NC(=O)C(C=C1C2)=CC=C1OC2CCCC1=CC=CC=C1 UUGGPISNCZNLTB-UHFFFAOYSA-N 0.000 description 1
UMZLDZKBMKEBFM-UHFFFAOYSA-N n-(2-cyano-4-oxochromen-8-yl)-2-(phenylmethoxymethyl)-2,3-dihydro-1-benzofuran-5-carboxamide Chemical compound C=1C=CC(C(C=C(O2)C#N)=O)=C2C=1NC(=O)C(C=C1C2)=CC=C1OC2COCC1=CC=CC=C1 UMZLDZKBMKEBFM-UHFFFAOYSA-N 0.000 description 1
PIIHPBHYDCOPKZ-UHFFFAOYSA-N n-fluoro-n-methylmethanamine Chemical compound CN(C)F PIIHPBHYDCOPKZ-UHFFFAOYSA-N 0.000 description 1
AIDQCFHFXWPAFG-UHFFFAOYSA-N n-formylformamide Chemical compound O=CNC=O AIDQCFHFXWPAFG-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002734 organomagnesium group Chemical group 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000013391 scatchard analysis Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
125000001391 thioamide group Chemical group 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
230000001732 thrombotic effect Effects 0.000 description 1
150000003595 thromboxanes Chemical class 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
230000008728 vascular permeability Effects 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 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 in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Organic Chemistry (AREA)
Veterinary Medicine (AREA)
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Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
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Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
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Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pulmonology (AREA)
Immunology (AREA)
Rheumatology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Dermatology (AREA)
Vascular Medicine (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Urology & Nephrology (AREA)
Otolaryngology (AREA)
Ophthalmology & Optometry (AREA)
Orthopedic Medicine & Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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SK1272-98A 1996-03-21 1997-03-20 Benzopyránové deriváty, spôsob ich prípravy a ich použitie SK282979B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES009600682A ES2127106B1 (es)	1996-03-21	1996-03-21	Derivados benzopiranicos con accion antagonista de los leucotrienos, procedimiento para su preparacion y utilizacion de los mismos.
PCT/EP1997/001418 WO1997034885A1 (en)	1996-03-21	1997-03-20	Benzopyran derivatives having leukotriene-antagonistic action

Publications (2)

Publication Number	Publication Date
SK127298A3 SK127298A3 (en)	1999-03-12
SK282979B6 true SK282979B6 (sk)	2003-01-09

Family

ID=8294261

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1272-98A SK282979B6 (sk)	1996-03-21	1997-03-20	Benzopyránové deriváty, spôsob ich prípravy a ich použitie

Country Status (30)

Country	Link
US (1)	US5990142A (pl)
EP (1)	EP0888327B1 (pl)
JP (1)	JP3914575B2 (pl)
KR (1)	KR100378892B1 (pl)
CN (1)	CN1182129C (pl)
AT (1)	ATE219073T1 (pl)
AU (1)	AU707282B2 (pl)
BG (1)	BG63433B1 (pl)
BR (1)	BR9708215A (pl)
CA (1)	CA2249402C (pl)
CU (1)	CU22777A3 (pl)
CZ (1)	CZ296260B6 (pl)
DE (1)	DE69713300T2 (pl)
DK (1)	DK0888327T3 (pl)
EA (1)	EA001680B1 (pl)
EE (1)	EE03526B1 (pl)
ES (2)	ES2127106B1 (pl)
GE (1)	GEP20012416B (pl)
HU (1)	HUP9901326A3 (pl)
IL (1)	IL126296A (pl)
NO (1)	NO319612B1 (pl)
NZ (1)	NZ331953A (pl)
PL (1)	PL189562B1 (pl)
PT (1)	PT888327E (pl)
RS (1)	RS49588B (pl)
SI (1)	SI0888327T1 (pl)
SK (1)	SK282979B6 (pl)
TR (1)	TR199801857T2 (pl)
UA (1)	UA65535C2 (pl)
WO (1)	WO1997034885A1 (pl)

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JP4745577B2 (ja)	1999-11-24	2011-08-10	ザリサーチファウンデイションオブステイトユニバーシティーオブニューヨーク	アミノアシル化活性を有した触媒ＲＮＡｓ
AU2003213136A1 (en) *	2002-02-15	2003-09-09	The Research Foundation Of State University Of New York At Buffalo	RIBOZYMES WITH BROAD tRNA AMINOACYLATION ACTIVITY
US7851486B2 (en)	2002-10-17	2010-12-14	Decode Genetics Ehf.	Susceptibility gene for myocardial infarction, stroke, and PAOD; methods of treatment
WO2004035741A2 (en) *	2002-10-17	2004-04-29	Decode Genetics Ehf.	Susceptibility gene for myocardial infarction; methods of treatment
ITTO20030140U1 (it) *	2003-09-16	2005-03-17	Interfila Srl	Matita cosmetica
CA2580584C (en)	2003-09-19	2015-07-28	Galileo Pharmaceuticals, Inc.	Use of alpha-tocotrienol for treatment of mitochondrial diseases
CN100475781C (zh) *	2004-02-13	2009-04-08	沃尼尔·朗伯有限责任公司	雄激素受体调节剂
CA2554696C (en)	2004-02-13	2009-06-30	Warner-Lambert Company Llc	Androgen receptor modulators
EP1737813A1 (en)	2004-04-13	2007-01-03	Warner-Lambert Company LLC	Androgen modulators
CA2570047C (en)	2004-07-08	2010-09-28	Warner-Lambert Company Llc	4-cycloalkoxy benzonitriles as androgen modulators
US20080064745A1 (en) *	2004-08-18	2008-03-13	Warner-Lambert Company Llc	Androgen Modulators
TW200724139A (en) *	2005-05-05	2007-07-01	Warner Lambert Co	Androgen modulators
US20090170886A1 (en) *	2005-08-08	2009-07-02	Pfizer Inc	Androgen modulators
WO2007066627A1 (ja) *	2005-12-06	2007-06-14	The University Of Tokyo	多目的アシル化触媒とその用途
ITMI20061606A1 (it) *	2006-08-09	2008-02-10	Dipharma Spa	Procedimento per la preparazione di composti nitrilici
CN102304052A (zh) *	2011-07-28	2012-01-04	浙江大学	一种制备5-溴-2-羟基-3-硝基苯乙酮的方法
CN103980257B (zh) *	2014-05-28	2016-04-27	苏州开元民生科技股份有限公司	8-硝基-2-四氮唑基-4-羰基苯并吡喃的合成方法
CN104402711A (zh) *	2014-11-12	2015-03-11	平湖优康药物研发有限公司	一种抗哮喘药物普伦斯特中间体的合成工艺
CN113651788B (zh) *	2021-09-16	2023-11-21	东华理工大学	一种3-胺烷基色酮化合物及其制备方法

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US4977162A (en) *	1989-07-13	1990-12-11	Rorer Pharmaceutical Corporation	Quinolinyl-chromone derivatives and use for treatment of hypersensitive ailments
JPH0395144A (ja) *	1989-08-04	1991-04-19	Ono Pharmaceut Co Ltd	アミノフェノール誘導体の製造方法

1996
- 1996-03-21 ES ES009600682A patent/ES2127106B1/es not_active Expired - Lifetime
1997
- 1997-03-20 SI SI9730340T patent/SI0888327T1/xx unknown
- 1997-03-20 DE DE69713300T patent/DE69713300T2/de not_active Expired - Fee Related
- 1997-03-20 BR BR9708215-5A patent/BR9708215A/pt not_active Application Discontinuation
- 1997-03-20 TR TR1998/01857T patent/TR199801857T2/xx unknown
- 1997-03-20 JP JP53315997A patent/JP3914575B2/ja not_active Expired - Fee Related
- 1997-03-20 PL PL97329027A patent/PL189562B1/pl not_active IP Right Cessation
- 1997-03-20 GE GEAP19974493A patent/GEP20012416B/en unknown
- 1997-03-20 EE EE9800318A patent/EE03526B1/xx not_active IP Right Cessation
- 1997-03-20 CZ CZ0299598A patent/CZ296260B6/cs not_active IP Right Cessation
- 1997-03-20 NZ NZ331953A patent/NZ331953A/xx not_active IP Right Cessation
- 1997-03-20 PT PT97914280T patent/PT888327E/pt unknown
- 1997-03-20 HU HU9901326A patent/HUP9901326A3/hu unknown
- 1997-03-20 EP EP97914280A patent/EP0888327B1/en not_active Expired - Lifetime
- 1997-03-20 ES ES97914280T patent/ES2176719T3/es not_active Expired - Lifetime
- 1997-03-20 AT AT97914280T patent/ATE219073T1/de not_active IP Right Cessation
- 1997-03-20 WO PCT/EP1997/001418 patent/WO1997034885A1/en not_active Ceased
- 1997-03-20 SK SK1272-98A patent/SK282979B6/sk not_active IP Right Cessation
- 1997-03-20 DK DK97914280T patent/DK0888327T3/da active
- 1997-03-20 KR KR10-1998-0707399A patent/KR100378892B1/ko not_active Expired - Fee Related
- 1997-03-20 EA EA199800738A patent/EA001680B1/ru unknown
- 1997-03-20 CN CNB971931933A patent/CN1182129C/zh not_active Expired - Fee Related
- 1997-03-20 UA UA98094930A patent/UA65535C2/uk unknown
- 1997-03-20 IL IL12629697A patent/IL126296A/en not_active IP Right Cessation
- 1997-03-20 AU AU21587/97A patent/AU707282B2/en not_active Ceased
- 1997-03-20 US US09/142,922 patent/US5990142A/en not_active Expired - Fee Related
- 1997-03-20 CA CA002249402A patent/CA2249402C/en not_active Expired - Fee Related
1998
- 1998-09-17 NO NO19984330A patent/NO319612B1/no not_active IP Right Cessation
- 1998-09-17 BG BG102775A patent/BG63433B1/bg unknown
- 1998-09-18 CU CU1998130A patent/CU22777A3/es not_active IP Right Cessation
- 1998-09-18 RS YUP-407/98A patent/RS49588B/sr unknown

Also Published As

Publication number	Publication date
ATE219073T1 (de)	2002-06-15
ES2127106B1 (es)	1999-11-16
PT888327E (pt)	2002-11-29
DE69713300T2 (de)	2002-09-26
PL189562B1 (pl)	2005-08-31
NO984330D0 (no)	1998-09-17
DK0888327T3 (da)	2002-09-16
SI0888327T1 (en)	2002-10-31
US5990142A (en)	1999-11-23
IL126296A0 (en)	1999-05-09
IL126296A (en)	2002-08-14
NO319612B1 (no)	2005-08-29
NZ331953A (en)	1999-03-29
EA001680B1 (ru)	2001-06-25
NO984330L (no)	1998-10-09
AU707282B2 (en)	1999-07-08
BG63433B1 (bg)	2002-01-31
WO1997034885A1 (en)	1997-09-25
CZ296260B6 (cs)	2006-02-15
HK1018701A1 (en)	1999-12-30
ES2176719T3 (es)	2002-12-01
CA2249402A1 (en)	1997-09-25
DE69713300D1 (de)	2002-07-18
YU40798A (en)	1999-11-22
UA65535C2 (en)	2004-04-15
JP2000506878A (ja)	2000-06-06
TR199801857T2 (xx)	1998-12-21
BG102775A (en)	1999-08-31
SK127298A3 (en)	1999-03-12
KR100378892B1 (ko)	2005-11-14
JP3914575B2 (ja)	2007-05-16
EP0888327A1 (en)	1999-01-07
EP0888327B1 (en)	2002-06-12
KR20000064682A (ko)	2000-11-06
CN1182129C (zh)	2004-12-29
EA199800738A1 (ru)	1999-06-24
EE03526B1 (et)	2001-10-15
AU2158797A (en)	1997-10-10
CZ299598A3 (cs)	1999-03-17
CA2249402C (en)	2006-10-24
ES2127106A1 (es)	1999-04-01
CU22777A3 (es)	2002-07-24
GEP20012416B (en)	2001-04-25
HUP9901326A2 (hu)	1999-08-30
RS49588B (sr)	2007-06-04
HUP9901326A3 (en)	2000-12-28
CN1214048A (zh)	1999-04-14
PL329027A1 (en)	1999-03-01
BR9708215A (pt)	2000-01-04
EE9800318A (et)	1999-04-15

Legal Events

Date	Code	Title	Description
2010-12-07	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20100320

Publication	Publication Date	Title
EP0888327B1 (en)	2002-06-12	Benzopyran derivatives having leukotriene-antagonistic action
DE3834204C2 (pl)	1992-04-23
US5103014A (en)	1992-04-07	Certain 3,3'-[[[(2-phenyl-4-thiazolyl)methoxy]phenyl]methylene]dithiobis-propanoic acid derivatives
EP0233763B1 (en)	1991-01-30	2-substituted quinoline dioic acids
Stokker et al.	1986	3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 3. 7-(3, 5-Disubstituted-[1, 1'-biphenyl]-2-yl)-3, 5-dihydroxy-6-heptenoic acids and their lactone derivatives
EP0540604A1 (en)	1993-05-12	Substituted bicyclic bis-aryl compounds exhibiting selective leukotriene b 4? antagonist activity, their preparation and use in pharmaceutical compositions
GB2210368A (en)	1989-06-07	2-aryl substituted heterocyclic compounds as antiallergic and anti-inflammatory agents
JPH04338386A (ja)	1992-11-25	ベンゾジオキソール、ベンゾジオキサンおよびベンゾジオキセピン誘導体
EP0223368A1 (en)	1987-05-27	Substituted naphthalene derivatives
US4665203A (en)	1987-05-12	Substituted dihydrobenzopyrans useful as leukotriene D4 inhibitors
NZ205559A (en)	1987-08-31	Leukotriene antagonists, pharmaceutical compositions, and intermediates
US4548948A (en)	1985-10-22	Anti-inflammatory and analgesic benzothiophene and benzafuran derivatives, compositions, and method of use therefor
EP0254329B1 (en)	1990-09-26	Substituted dihydrobenzopyranones
JPH0383979A (ja)	1991-04-09	新規ベンゾピランおよびベンゾチオピラン誘導体
AU761327B2 (en)	2003-06-05	Fused benzene heterocycle derivatives and utilization thereof
DE69521132T2 (de)	2001-09-27	Naphthalenamide als leukotrien antagonisten
US4778903A (en)	1988-10-18	Substituted dihydrobenzopyrans
FI101300B (fi)	1998-05-29	Menetelmä farmakologisesti aktiivisten 1,2,3,4-tetrahydrokinoliini-6-e tikkahappojohdannaisten valmistamiseksi ja välituotteena käytettävät k inoliinijohdannaiset
US5155130A (en)	1992-10-13	Certain benzopyran and benzothiopyran derivatives
US4952705A (en)	1990-08-28	Substituted dihydrobenzopyrans
US4888356A (en)	1989-12-19	Use of substituted dihydrobenzopyrans for allergy and inflammation
EP0924202B1 (en)	2002-05-29	Imidazole derivative and medicine comprising the same as active ingredient
JPH0250113B2 (pl)	1990-11-01
Ayoub	2010	Synthetic Study of Ethyl (2E)-4-bromo-3-ethoxybut-2-enoate: Synthesis of New 1, 4-Benzoxazines and Pyrrole-2-ones