DD297160A5 - Bestimmte benzopyran- und benzothiopyranderivate - Google Patents

Bestimmte benzopyran- und benzothiopyranderivate Download PDF

Info

Publication number: DD297160A5
Authority: DD; German Democratic Republic
Prior art keywords: carbocyclic; lower alkyl; hydrogen; formula; compound according
Prior art date: 1989-08-11

Application number

DD90343289A

Other languages

German (de)

English (en)

Inventor

James L Stanton

Yoshitaka Satch

Alan J Hutchison

Original Assignee

��`��@��k��

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.)

1989-08-11

Filing date

1990-08-07

Publication date

1992-01-02

1990-08-07 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1992-01-02 Publication of DD297160A5 publication Critical patent/DD297160A5/de

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KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 title abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 143
238000000034 method Methods 0.000 claims abstract description 46
230000008569 process Effects 0.000 claims abstract description 24
238000002360 preparation method Methods 0.000 claims abstract description 16
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
239000000867 Lipoxygenase Inhibitor Substances 0.000 claims abstract description 6
230000002757 inflammatory effect Effects 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 88
239000000203 mixture Substances 0.000 claims description 88
239000001257 hydrogen Substances 0.000 claims description 81
229910052739 hydrogen Inorganic materials 0.000 claims description 81
125000002837 carbocyclic group Chemical group 0.000 claims description 51
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
150000003839 salts Chemical class 0.000 claims description 49
-1 lower alkylnylamino Chemical group 0.000 claims description 39
125000003545 alkoxy group Chemical group 0.000 claims description 36
150000002431 hydrogen Chemical group 0.000 claims description 30
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 26
229910052760 oxygen Inorganic materials 0.000 claims description 22
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
238000009833 condensation Methods 0.000 claims description 20
230000005494 condensation Effects 0.000 claims description 20
125000000623 heterocyclic group Chemical group 0.000 claims description 20
239000001301 oxygen Substances 0.000 claims description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 15
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
125000006239 protecting group Chemical group 0.000 claims description 13
239000011593 sulfur Substances 0.000 claims description 13
125000003282 alkyl amino group Chemical group 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
125000001589 carboacyl group Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
208000027866 inflammatory disease Diseases 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 4
208000026935 allergic disease Diseases 0.000 claims description 4
239000012948 isocyanate Substances 0.000 claims description 4
150000002513 isocyanates Chemical class 0.000 claims description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000006319 alkynyl amino group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
150000002540 isothiocyanates Chemical class 0.000 claims description 3
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
229940124125 5 Lipoxygenase inhibitor Drugs 0.000 claims 2
125000006323 alkenyl amino group Chemical group 0.000 claims 2
125000001769 aryl amino group Chemical group 0.000 claims 2
125000001475 halogen functional group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
206010027654 Allergic conditions Diseases 0.000 abstract description 5
150000001562 benzopyrans Chemical class 0.000 abstract description 5
ONJRTQUWKRDCTA-UHFFFAOYSA-N 2h-thiochromene Chemical class C1=CC=C2C=CCSC2=C1 ONJRTQUWKRDCTA-UHFFFAOYSA-N 0.000 abstract description 4
238000004519 manufacturing process Methods 0.000 abstract description 3
230000002265 prevention Effects 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 94
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 93
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 92
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
235000019439 ethyl acetate Nutrition 0.000 description 33
239000007858 starting material Substances 0.000 description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
238000002844 melting Methods 0.000 description 25
230000008018 melting Effects 0.000 description 25
239000007787 solid Substances 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
229910000027 potassium carbonate Inorganic materials 0.000 description 18
230000015572 biosynthetic process Effects 0.000 description 17
125000004432 carbon atom Chemical group C* 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000012044 organic layer Substances 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
239000010410 layer Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
239000000284 extract Substances 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
230000005764 inhibitory process Effects 0.000 description 10
241000124008 Mammalia Species 0.000 description 9
239000002904 solvent Substances 0.000 description 9
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
238000003818 flash chromatography Methods 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
238000000746 purification Methods 0.000 description 8
QJPGNXTVPKAIOB-UHFFFAOYSA-N 2-hydroxy-5-phenoxybenzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1OC1=CC=CC=C1 QJPGNXTVPKAIOB-UHFFFAOYSA-N 0.000 description 7
102000003820 Lipoxygenases Human genes 0.000 description 7
108090000128 Lipoxygenases Proteins 0.000 description 7
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 7
150000001299 aldehydes Chemical class 0.000 description 7
150000002443 hydroxylamines Chemical class 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
238000010898 silica gel chromatography Methods 0.000 description 7
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 6
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
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 6
239000002585 base Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
201000010099 disease Diseases 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
210000000265 leukocyte Anatomy 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
206010020751 Hypersensitivity Diseases 0.000 description 5
206010061218 Inflammation Diseases 0.000 description 5
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
230000007815 allergy Effects 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
208000006673 asthma Diseases 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
239000008280 blood Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000001914 filtration Methods 0.000 description 5
230000004054 inflammatory process Effects 0.000 description 5
239000008101 lactose Substances 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
239000000725 suspension Substances 0.000 description 5
CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 4
KGIJOOYOSFUGPC-CABOLEKPSA-N 5-HETE Natural products CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](O)CCCC(O)=O KGIJOOYOSFUGPC-CABOLEKPSA-N 0.000 description 4
KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 4
JSPGOHYLKVWWKI-UHFFFAOYSA-N 6-hydroxy-2h-chromene-3-carbaldehyde Chemical compound O1CC(C=O)=CC2=CC(O)=CC=C21 JSPGOHYLKVWWKI-UHFFFAOYSA-N 0.000 description 4
241000282472 Canis lupus familiaris Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
201000004624 Dermatitis Diseases 0.000 description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
229940114079 arachidonic acid Drugs 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
208000010668 atopic eczema Diseases 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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230000000694 effects Effects 0.000 description 4
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NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical class C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 4
150000002617 leukotrienes Chemical class 0.000 description 4
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150000002923 oximes Chemical class 0.000 description 4
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HIYAVKIYRIFSCZ-CYEMHPAKSA-N 5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid Chemical compound O=C([C@@H](C)[C@H]1O[C@@]2([C@@H](C[C@H]1C)C)O[C@@H]([C@@H](CC2)C)CC=1OC2=CC=C(C(=C2N=1)C(O)=O)NC)C1=CC=CN1 HIYAVKIYRIFSCZ-CYEMHPAKSA-N 0.000 description 3
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NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 description 3
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229910052799 carbon Inorganic materials 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
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239000000969 carrier Substances 0.000 description 3
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125000004093 cyano group Chemical group *C#N 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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239000000543 intermediate Substances 0.000 description 3
230000000302 ischemic effect Effects 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
SYRZIXRJGTVJEF-UHFFFAOYSA-N n-[(6-phenoxy-2h-chromen-3-yl)methyl]hydroxylamine Chemical compound C=1C=C2OCC(CNO)=CC2=CC=1OC1=CC=CC=C1 SYRZIXRJGTVJEF-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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150000003254 radicals Chemical class 0.000 description 3
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SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 3
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KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E)-hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 description 2
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MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 2
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
CWKFWBJJNNPGAM-IPZCTEOASA-N Ozagrel hydrochloride Chemical compound Cl.C1=CC(/C=C/C(=O)O)=CC=C1CN1C=NC=C1 CWKFWBJJNNPGAM-IPZCTEOASA-N 0.000 description 2
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230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
229950002877 pirmagrel Drugs 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
230000010118 platelet activation Effects 0.000 description 1
210000003281 pleural cavity Anatomy 0.000 description 1
208000008423 pleurisy Diseases 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000008213 purified water Substances 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
229960001404 quinidine Drugs 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
238000011552 rat model Methods 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
239000000523 sample Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940121356 serotonin receptor antagonist Drugs 0.000 description 1
230000035939 shock Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
229960005453 strychnine Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229950001172 sulotroban Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
VRWJIPGNRHFNQT-UHFFFAOYSA-N tert-butyl 6-phenylmethoxy-2h-chromene-3-carboxylate Chemical compound C=1C=C2OCC(C(=O)OC(C)(C)C)=CC2=CC=1OCC1=CC=CC=C1 VRWJIPGNRHFNQT-UHFFFAOYSA-N 0.000 description 1
125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DRDVJQOGFWAVLH-UHFFFAOYSA-N tert-butyl n-hydroxycarbamate Chemical compound CC(C)(C)OC(=O)NO DRDVJQOGFWAVLH-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
239000002396 thromboxane receptor blocking agent Substances 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
MBDOYVRWFFCFHM-UHFFFAOYSA-N trans-2-hexenal Natural products CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
230000002792 vascular Effects 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
230000008728 vascular permeability Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229960004764 zafirlukast Drugs 0.000 description 1

Classifications

- 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
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pulmonology (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pyrane Compounds (AREA)

DD90343289A 1989-08-11 1990-08-07 Bestimmte benzopyran- und benzothiopyranderivate DD297160A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US39251089A	1989-08-11	1989-08-11

Publications (1)

Publication Number	Publication Date
DD297160A5 true DD297160A5 (de)	1992-01-02

Family

ID=23550888

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90343289A DD297160A5 (de)	1989-08-11	1990-08-07	Bestimmte benzopyran- und benzothiopyranderivate

Country Status (15)

Country	Link
EP (1)	EP0412939A3 (pt)
JP (1)	JPH0383979A (pt)
KR (1)	KR910004590A (pt)
AU (1)	AU631913B2 (pt)
CA (1)	CA2023016A1 (pt)
DD (1)	DD297160A5 (pt)
FI (1)	FI903928A7 (pt)
HU (1)	HU206874B (pt)
IE (1)	IE902908A1 (pt)
IL (1)	IL95285A0 (pt)
MX (1)	MX21917A (pt)
NO (1)	NO903533L (pt)
NZ (1)	NZ234840A (pt)
PT (1)	PT94912A (pt)
ZA (1)	ZA906328B (pt)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0541807B1 (en) *	1990-07-27	1997-12-17	Chugai Seiyaku Kabushiki Kaisha	Novel benzopyran derivative
FR2673629B1 (fr) *	1991-03-08	1993-05-07	Adir	Nouveaux derives du benzopyrane leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
DE4123613C1 (pt) *	1991-07-17	1993-02-04	Gruenenthal Gmbh, 5100 Aachen, De
DE4128690A1 (de) *	1991-08-29	1993-03-04	Boehringer Mannheim Gmbh	Bicyclische sulfone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
NZ251174A (en) *	1992-04-07	1996-01-26	Merrell Dow Pharma	Hydraziniumcarbonyl derivatives of benzopyrans; medicaments
FR2691149B1 (fr) *	1992-05-18	1994-07-08	Adir	Nouveaux composes thiochromaniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent.
US5612377A (en) *	1994-08-04	1997-03-18	Minnesota Mining And Manufacturing Company	Method of inhibiting leukotriene biosynthesis
DE19647000A1 (de) *	1996-11-14	1998-05-20	Hoechst Ag	3-Amido-chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
US6077850A (en) *	1997-04-21	2000-06-20	G.D. Searle & Co.	Substituted benzopyran analogs for the treatment of inflammation
US6034256A (en) *	1997-04-21	2000-03-07	G.D. Searle & Co.	Substituted benzopyran derivatives for the treatment of inflammation
JPH11106381A (ja) *	1997-09-30	1999-04-20	Ss Pharmaceut Co Ltd	クロメン誘導体及びその塩並びにこれを含有する医薬
DE69830929T2 (de) *	1997-11-11	2006-04-20	Nikken Chemicals Co., Ltd.	N-hydroxyurea-derivat und dieses enthaltende pharmazeutische zusammensetzung
FR2787789B1 (fr) *	1998-12-29	2002-06-14	Lipha	Benzopyranes et benzoxepines utilisables dans le traitement de dyslipidemies, de l'atherosclerose et du diabete, compositions pharmaceutiques les contenant et procedes de preparations
JP5817614B2 (ja) *	2012-03-26	2015-11-18	日本ゼオン株式会社	２，５−ジヒドロキシベンズアルデヒド化合物の製造方法
EP2853530A1 (en) *	2013-09-25	2015-04-01	Université de Rennes 1	New PI3K/AKT/mTOR inhibitors and pharmaceutical uses thereof
ES2534336B1 (es) *	2013-10-18	2016-01-28	Artax Biopharma Inc.	Derivados de cromeno como inhibidores de la interacción TCR-Nck

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0218373B1 (en) *	1985-09-11	1990-03-07	Beecham Group Plc	Chroman derivatives and analogues having antihypertensive activity
FR2593504B1 (fr) *	1986-01-30	1988-12-09	Ile De France	Nouveaux derives de dihydrobenzofuranne - et de chromane - carboxamides, leurs procedes de preparation et leur utilisation comme neuroleptiques
GB8830427D0 (en) *	1988-12-30	1989-03-01	Fujisawa Pharmaceutical Co	New hydroxylamine derivatives,a process for the preparation thereof and pharmaceutical composition comprising the same
GB8911280D0 (en) *	1989-05-17	1989-07-05	Beecham Group Plc	Novel compounds

1990
- 1990-08-02 EP EP19900810587 patent/EP0412939A3/en not_active Withdrawn
- 1990-08-03 PT PT94912A patent/PT94912A/pt not_active Application Discontinuation
- 1990-08-05 IL IL95285A patent/IL95285A0/xx unknown
- 1990-08-07 DD DD90343289A patent/DD297160A5/de not_active IP Right Cessation
- 1990-08-08 FI FI903928A patent/FI903928A7/fi not_active IP Right Cessation
- 1990-08-09 NZ NZ234840A patent/NZ234840A/en unknown
- 1990-08-09 MX MX2191790A patent/MX21917A/es unknown
- 1990-08-09 CA CA002023016A patent/CA2023016A1/en not_active Abandoned
- 1990-08-10 NO NO90903533A patent/NO903533L/no unknown
- 1990-08-10 ZA ZA906328A patent/ZA906328B/xx unknown
- 1990-08-10 JP JP2210586A patent/JPH0383979A/ja active Pending
- 1990-08-10 KR KR1019900012269A patent/KR910004590A/ko not_active Withdrawn
- 1990-08-10 HU HU904978A patent/HU206874B/hu not_active IP Right Cessation
- 1990-08-10 AU AU60895/90A patent/AU631913B2/en not_active Ceased
- 1990-08-10 IE IE290890A patent/IE902908A1/en unknown

Also Published As

Publication number	Publication date
NO903533L (no)	1991-02-12
EP0412939A2 (en)	1991-02-13
HU904978D0 (en)	1991-01-28
MX21917A (es)	1994-02-28
EP0412939A3 (en)	1991-09-04
IL95285A0 (en)	1991-06-30
FI903928A7 (fi)	1991-02-12
JPH0383979A (ja)	1991-04-09
FI903928A0 (fi)	1990-08-08
NZ234840A (en)	1992-09-25
PT94912A (pt)	1991-04-18
ZA906328B (en)	1991-04-24
AU6089590A (en)	1991-02-14
HUT54671A (en)	1991-03-28
IE902908A1 (en)	1991-02-27
CA2023016A1 (en)	1991-02-12
NO903533D0 (no)	1990-08-10
KR910004590A (ko)	1991-03-29
AU631913B2 (en)	1992-12-10
HU206874B (en)	1993-01-28

Legal Events

Date	Code	Title	Description
1998-08-27	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69532195T2 (de)	2004-09-02	Benzamidverbindung und ihre medizinische verwendung
US4876346A (en)	1989-10-24	Quinoline compounds
DE60205564T2 (de)	2006-06-01	N-Adamantylalkyl Benzamide Derivativen als p2x7-rezeptor antagonisten
US6130232A (en)	2000-10-10	Substituted piperidine derivatives as muscarinic M3 receptor antagonists
US5231101A (en)	1993-07-27	Benzo[5,6]cyclohepta[1,2-B]pyridine derivatives and antiallergic agents comprising same
DE69224697T2 (de)	1998-07-16	Verbindungen, nützlich als leukotriene Antagonisten
DE69725978T2 (de)	2004-09-02	Chalcon-derivate und medikamente die diese enthalten
DE69118388T2 (de)	1996-11-14	Substituierte bizyklische arylderivate mit selektiver leukotrien b4 antagonistischer wirkung
CA1200241A (en)	1986-02-04	Pharmaceutically active 1,2,3,4,4a,5,10,10a-octahydro- benzo¬g\|quinoline derivatives
US4661596A (en)	1987-04-28	Quinolinyl (or pyridinyl) methoxy substituted naphthalene compounds as antiallergic agents
GB2210368A (en)	1989-06-07	2-aryl substituted heterocyclic compounds as antiallergic and anti-inflammatory agents
US4772703A (en)	1988-09-20	2-(phenoxymethyl)-quinazolines as antiallergic and antiinflammatory agents
DE3632329A1 (de)	1988-03-31	Substituierte phenylsulfonamide
SK281282B6 (sk)	2001-02-12	7-(2-aminoetyl)benzotiazolóny, spôsob ich výroby, farmaceutická kompozícia s ich obsahom a medziprodukt spôsobu výroby
DE69719358T2 (de)	2003-12-24	Substituierte dihydrobenzofurane als pde-hemmstoffe
DE69224115T2 (de)	1998-08-20	Heteroaryl substituierte Hydroxylaminderivate als Lipoxygenase-Inhibitoren
DE69204252T2 (de)	1996-04-18	Chinoline Derivate, nützlich als Angiotensin-II-Antagonisten.
IE902908A1 (en)	1991-02-27	Certain benzopyran and benzothiopyran derivatives
US5747513A (en)	1998-05-05	Derivatives of 2-amino-1,2,3,4-tetrahydronaphthalene active on the cardiovascular system
CH645892A5 (de)	1984-10-31	Carbostyrilderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende, antihistaminisch wirkende mittel.
US4904786A (en)	1990-02-27	Quinoline compounds as antiallergic and antiinflammatory agents
DE3830060A1 (de)	1990-03-15	2-phenylbenzimidazole - verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel
US5095022A (en)	1992-03-10	Piperidine derivatives and pharmaceutical compositions comprising the same
DE69405624T2 (de)	1998-01-15	Pharmazeutische Verbindungen
EP0250361B1 (de)	1993-12-08	Disubstituierte Piperazine