UA65535C2 - Benzopyran derivatives and a method for the preparation thereof - Google Patents

Benzopyran derivatives and a method for the preparation thereof Download PDF

Info

Publication number: UA65535C2
Authority: UA; Ukraine
Prior art keywords: benzopyran; oxo; compound; formula; phenyl
Prior art date: 1996-03-21

Application number

UA98094930A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Menarini Lab

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

2004-04-15

1997-03-20 Application filed by Menarini Lab filed Critical Menarini Lab

2004-04-15 Publication of UA65535C2 publication Critical patent/UA65535C2/uk

Links

238000000034 method Methods 0.000 title claims description 146
150000001562 benzopyrans Chemical class 0.000 title abstract description 5
238000002360 preparation method Methods 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 280
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 75
-1 5-tetrazolyl Chemical group 0.000 claims abstract description 54
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
239000001257 hydrogen Substances 0.000 claims abstract description 36
229910052760 oxygen Inorganic materials 0.000 claims abstract description 29
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 28
239000001301 oxygen Substances 0.000 claims abstract description 27
229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
125000004434 sulfur atom Chemical group 0.000 claims abstract description 6
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 5
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 3
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
239000003814 drug Substances 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 65
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
238000006243 chemical reaction Methods 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 21
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
239000000460 chlorine Substances 0.000 claims description 17
229910052801 chlorine Inorganic materials 0.000 claims description 17
238000004519 manufacturing process Methods 0.000 claims description 16
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
150000002431 hydrogen Chemical group 0.000 claims description 15
239000011593 sulfur Substances 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
150000002617 leukotrienes Chemical class 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 9
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 9
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 8
230000015572 biosynthetic process Effects 0.000 claims description 8
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000005228 aryl sulfonate group Chemical group 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
YBEGJIJGDLRCLU-UHFFFAOYSA-N 4-oxo-8-[[2-(phenylmethoxymethyl)-2,3-dihydro-1-benzofuran-5-carbonyl]amino]chromene-2-carboxylic acid Chemical compound C=12OC(C(=O)O)=CC(=O)C2=CC=CC=1NC(=O)C(C=C1C2)=CC=C1OC2COCC1=CC=CC=C1 YBEGJIJGDLRCLU-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 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
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
208000010668 atopic eczema Diseases 0.000 claims description 3
229910052796 boron Inorganic materials 0.000 claims description 3
208000006752 brain edema Diseases 0.000 claims description 3
230000000747 cardiac effect Effects 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 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
125000006239 protecting group Chemical group 0.000 claims description 3
239000012453 solvate Substances 0.000 claims description 3
DIAKMWIJFVXOKU-UHFFFAOYSA-N 8-[[2-(benzylsulfanylmethyl)-2,3-dihydro-1-benzofuran-5-carbonyl]amino]-4-oxochromene-2-carboxylic acid Chemical compound C=12OC(C(=O)O)=CC(=O)C2=CC=CC=1NC(=O)C(C=C1C2)=CC=C1OC2CSCC1=CC=CC=C1 DIAKMWIJFVXOKU-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
230000000172 allergic effect Effects 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
150000001805 chlorine compounds Chemical class 0.000 claims description 2
208000027866 inflammatory disease Diseases 0.000 claims description 2
230000003993 interaction Effects 0.000 claims description 2
150000002500 ions Chemical class 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
WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 claims description 2
206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
201000004415 tendinitis Diseases 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
230000001404 mediated effect Effects 0.000 claims 3
101150078171 OSH3 gene Proteins 0.000 claims 1
240000004922 Vigna radiata Species 0.000 claims 1
235000010721 Vigna radiata var radiata Nutrition 0.000 claims 1
235000011469 Vigna radiata var sublobata Nutrition 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
229940124597 therapeutic agent Drugs 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 4
230000003266 anti-allergic effect Effects 0.000 abstract description 2
230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 142
238000005481 NMR spectroscopy Methods 0.000 description 130
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
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 80
239000002904 solvent Substances 0.000 description 78
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 65
239000000243 solution Substances 0.000 description 61
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 59
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 55
239000000741 silica gel Substances 0.000 description 55
229910002027 silica gel Inorganic materials 0.000 description 55
239000000047 product Substances 0.000 description 52
238000004587 chromatography analysis Methods 0.000 description 44
239000007787 solid Substances 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
239000003208 petroleum Substances 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
239000012074 organic phase Substances 0.000 description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000012043 crude product Substances 0.000 description 18
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 18
238000001953 recrystallisation Methods 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000007858 starting material Substances 0.000 description 15
238000009835 boiling Methods 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
229910052740 iodine Inorganic materials 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
238000003756 stirring Methods 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical class [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 9
238000003818 flash chromatography Methods 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
238000010898 silica gel chromatography Methods 0.000 description 8
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000012047 saturated solution Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
239000000725 suspension Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
230000009471 action Effects 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
230000003042 antagnostic effect Effects 0.000 description 5
239000008346 aqueous phase 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
IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
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 description 4
229940002520 2'-hydroxyacetophenone Drugs 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
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
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
230000027455 binding Effects 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 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
239000000706 filtrate Substances 0.000 description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
230000004054 inflammatory process Effects 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000012071 phase Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
239000011780 sodium chloride Substances 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
238000012360 testing method Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
238000002560 therapeutic procedure Methods 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
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
ZNOREXRHKZXVPC-UHFFFAOYSA-N (4-fluorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(F)C=C1 ZNOREXRHKZXVPC-UHFFFAOYSA-N 0.000 description 3
NLLYXOVHEQVWJF-UHFFFAOYSA-N 1-(3-amino-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(N)=C1O NLLYXOVHEQVWJF-UHFFFAOYSA-N 0.000 description 3
YTXKWBRGENHZKP-UHFFFAOYSA-N 2-(benzylsulfanylmethyl)-3h-1-benzofuran-2-carboxylic acid Chemical compound C1C2=CC=CC=C2OC1(C(=O)O)CSCC1=CC=CC=C1 YTXKWBRGENHZKP-UHFFFAOYSA-N 0.000 description 3
FYKSEGREJYMERR-UHFFFAOYSA-N 2-[(4-fluorophenyl)methoxymethyl]-3h-1-benzofuran-2-carboxylic acid Chemical class C1C2=CC=CC=C2OC1(C(=O)O)COCC1=CC=C(F)C=C1 FYKSEGREJYMERR-UHFFFAOYSA-N 0.000 description 3
KDLVSGWUKFJFTL-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-2-ylmethanol Chemical compound C1=CC=C2OC(CO)CCC2=C1 KDLVSGWUKFJFTL-UHFFFAOYSA-N 0.000 description 3
JCIDEANDDNSHQC-UHFFFAOYSA-N 4H-chromene Chemical compound C1=CC=C2CC=COC2=C1 JCIDEANDDNSHQC-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
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
238000007098 aminolysis reaction Methods 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
210000004072 lung Anatomy 0.000 description 3
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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
- A61P11/02—Nasal agents, e.g. decongestants
- 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
- A61P11/06—Antiasthmatics
- 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
- 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
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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
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- A61P27/02—Ophthalmic agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
- 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
- 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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Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
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Urology & Nephrology (AREA)
Otolaryngology (AREA)
Ophthalmology & Optometry (AREA)
Orthopedic Medicine & Surgery (AREA)
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UA98094930A 1996-03-21 1997-03-20 Benzopyran derivatives and a method for the preparation thereof UA65535C2 (en)

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 (fr)	1996-03-21	1997-03-20	Derives de benzopyrane a action antagoniste vis-a-vis des leucotrienes

Publications (1)

Publication Number	Publication Date
UA65535C2 true UA65535C2 (en)	2004-04-15

Family

ID=8294261

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA98094930A UA65535C2 (en)	1996-03-21	1997-03-20	Benzopyran derivatives and a method for the preparation thereof

Country Status (30)

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

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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 (fr) *	2002-10-17	2004-04-29	Decode Genetics Ehf.	Gene de susceptibilite pour l'infarctus du myocarde, et procedes de traitement
ITTO20030140U1 (it) *	2003-09-16	2005-03-17	Interfila Srl	Matita cosmetica
CA2580584C (fr)	2003-09-19	2015-07-28	Galileo Pharmaceuticals, Inc.	Utilisation d'alpha-tocotrienol pour le traitement de maladies mitochondriales
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 (fr)	2004-02-13	2009-06-30	Warner-Lambert Company Llc	Modulateurs du recepteur d'androgene
EP1737813A1 (fr)	2004-04-13	2007-01-03	Warner-Lambert Company LLC	Modulateurs d'androgenes
CA2570047C (fr)	2004-07-08	2010-09-28	Warner-Lambert Company Llc	4-cycloalkoxybenzonitriles utilises comme modulateurs d'androgenes
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 (fr) *	2005-12-06	2007-06-14	The University Of Tokyo	Catalyseur d'acylation polyvalent et utilisation de celui-ci
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/fr 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/fr 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/fr 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 (fr)	1997-09-25
CZ296260B6 (cs)	2006-02-15
HK1018701A1 (en)	1999-12-30
ES2176719T3 (es)	2002-12-01
CA2249402A1 (fr)	1997-09-25
DE69713300D1 (de)	2002-07-18
YU40798A (en)	1999-11-22
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 (fr)	1999-01-07
SK282979B6 (sk)	2003-01-09
EP0888327B1 (fr)	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 (fr)	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

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Waugh et al.	1985	Synthesis and characterization of selected heteroarotinoids. Pharmacological activity as assessed in vitamin A deficient hamster tracheal organ cultures. Single-crystal X-ray diffraction analysis of 4, 4-dimethylthiochroman-6-yl methyl ketone 1, 1-dioxide and ethyl (E)-p-[2-(4, 4-dimethylthiochroman-6-yl) propenyl] benzoate
DE69713300T2 (de)	2002-09-26	Benzopyran derivate mit leukotrien-antagonistischer wirkung
DE69217998T2 (de)	1997-06-12	Benzopyrane und ähnliche LTB4-Antagonisten
JP2007538103A (ja)	2007-12-27	トランスサイレチン安定化
KR20100132073A (ko)	2010-12-16	Ｐａｉ―１ 저해제
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Kobzar et al.	2023	Carboxylated chalcones and related flavonoids as inhibitors of xanthine oxidase
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JP5311371B2 (ja)	2013-10-09	メチル化カテキンの効率的製造方法
PL105799B1 (pl)	1979-10-31	Sposob wytwarzania nowych pochodnych/alfa-aminoacetylo/benzenu
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RU2058979C1 (ru)	1996-04-27	Производные алкенкарбоновой кислоты, или смеси их изомеров, или их индивидуальные изомеры, или соли, обладающие свойствами антагонистов лейкотриена, способы их получения, промежуточные для их получения, и фармацевтическая композиция на их основе
WO2009036428A2 (fr)	2009-03-19	Benzènes 1,3,4-trisubstitués
JPS63264440A (ja)	1988-11-01	２，４，５−トリフルオロ−３−ヒドロキシ安息香酸及びその製造法
WO2025043316A1 (fr)	2025-03-06	Procédé d'obtention de composés anti-inflammatoires, lesdits composés, composition pharmaceutique et utilisation desdits composés et de la composition pharmaceutique
JPS5829774B2 (ja)	1983-06-24	アルフア − チカンプロピオンサンオヨビソノエンノセイゾウホウホウ
DE4006640A1 (de)	1991-09-05	Phenylthioalkylcarbonsaeure-derivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel