JPH0473436B2 - - Google Patents

Info

Publication number: JPH0473436B2
Authority: JP; Japan
Prior art keywords: compound; acid; reaction; hydroxy; group
Prior art date: 1985-08-09
Legal status (The legal status 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 status listed.): Expired

Application number

JP17631085A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6236391A (ja

Inventor

Noryoshi Horie

Shozo Yamamoto

Shigekatsu Kono

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Otsuka Pharmaceutical Co Ltd

Original Assignee

Otsuka Pharmaceutical Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-08-09

Filing date

1985-08-09

Publication date

1992-11-20

1985-08-09 Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd

1985-08-09 Priority to JP17631085A priority Critical patent/JPS6236391A/ja

1987-02-17 Publication of JPS6236391A publication Critical patent/JPS6236391A/ja

1992-11-20 Publication of JPH0473436B2 publication Critical patent/JPH0473436B2/ja

Status Granted legal-status Critical Current

Links

150000002212 flavone derivatives Chemical class 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000001875 compounds Chemical class 0.000 description 79
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
-1 t-butoxy group Chemical group 0.000 description 31
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
235000019441 ethanol Nutrition 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
238000010586 diagram Methods 0.000 description 17
238000003786 synthesis reaction Methods 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
239000013078 crystal Substances 0.000 description 16
239000000203 mixture Substances 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
230000015572 biosynthetic process Effects 0.000 description 15
208000006673 asthma Diseases 0.000 description 14
239000000243 solution Substances 0.000 description 14
238000002211 ultraviolet spectrum Methods 0.000 description 14
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
238000000034 method Methods 0.000 description 12
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239000011541 reaction mixture Substances 0.000 description 11
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238000002329 infrared spectrum Methods 0.000 description 10
229920000137 polyphosphoric acid Polymers 0.000 description 10
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239000008107 starch Substances 0.000 description 10
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 9
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
238000003756 stirring Methods 0.000 description 9
238000005160 1H NMR spectroscopy Methods 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
VIGBIBDAVDHOTP-UHFFFAOYSA-M sodium;ethanol;acetate Chemical compound [Na+].CCO.CC([O-])=O VIGBIBDAVDHOTP-UHFFFAOYSA-M 0.000 description 8
239000000126 substance Substances 0.000 description 8
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 7
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 7
239000003054 catalyst Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
230000002401 inhibitory effect Effects 0.000 description 7
239000008101 lactose Substances 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
239000000825 pharmaceutical preparation Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000007921 spray Substances 0.000 description 6
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
239000000427 antigen Substances 0.000 description 5
102000036639 antigens Human genes 0.000 description 5
108091007433 antigens Proteins 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
150000007514 bases Chemical class 0.000 description 5
230000000694 effects Effects 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000008103 glucose Substances 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 5
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
206010030111 Oedema mucosal Diseases 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
IQZLUWLMQNGTIW-UHFFFAOYSA-N acetoveratrone Chemical compound COC1=CC=C(C(C)=O)C=C1OC IQZLUWLMQNGTIW-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
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 4
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
239000003814 drug Substances 0.000 description 4
238000006266 etherification reaction Methods 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000012046 mixed solvent Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
238000011282 treatment Methods 0.000 description 4
239000008096 xylene Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
241000700199 Cavia porcellus Species 0.000 description 3
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
206010020751 Hypersensitivity Diseases 0.000 description 3
206010061218 Inflammation Diseases 0.000 description 3
239000000867 Lipoxygenase Inhibitor Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
WHFSJKCACRWVPW-UHFFFAOYSA-N [4-(5-hexoxy-6,7-dimethoxy-4-oxochromen-2-yl)-2-hydroxyphenyl] dihydrogen phosphate Chemical compound C=1C(=O)C=2C(OCCCCCC)=C(OC)C(OC)=CC=2OC=1C1=CC=C(OP(O)(O)=O)C(O)=C1 WHFSJKCACRWVPW-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 3
230000007815 allergy Effects 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
239000000924 antiasthmatic agent Substances 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000008859 change Effects 0.000 description 3
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
235000019404 dichlorodifluoromethane Nutrition 0.000 description 3
201000010099 disease Diseases 0.000 description 3
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238000007327 hydrogenolysis reaction Methods 0.000 description 3
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NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
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UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
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CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
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JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
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DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 2
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XZRIVAKQBKTLEQ-UHFFFAOYSA-N 6,7-dimethoxy-2-phenylchromen-4-one Chemical compound C=1C(=O)C=2C=C(OC)C(OC)=CC=2OC=1C1=CC=CC=C1 XZRIVAKQBKTLEQ-UHFFFAOYSA-N 0.000 description 2
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239000002841 Lewis acid Substances 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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239000002202 Polyethylene glycol Substances 0.000 description 2
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150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
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VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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210000004369 blood Anatomy 0.000 description 2
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125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
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FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
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239000008187 granular material Substances 0.000 description 2
238000011597 hartley guinea pig Methods 0.000 description 2
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
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125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
150000002617 leukotrienes Chemical class 0.000 description 2
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229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
238000000954 titration curve Methods 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
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
239000003656 tris buffered saline Substances 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP17631085A 1985-08-09 1985-08-09 新規フラボン誘導体 Granted JPS6236391A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP17631085A JPS6236391A (ja)	1985-08-09	1985-08-09	新規フラボン誘導体

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP17631085A JPS6236391A (ja)	1985-08-09	1985-08-09	新規フラボン誘導体

Publications (2)

Publication Number	Publication Date
JPS6236391A JPS6236391A (ja)	1987-02-17
JPH0473436B2 true JPH0473436B2 (de)	1992-11-20

Family

ID=16011349

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP17631085A Granted JPS6236391A (ja)	1985-08-09	1985-08-09	新規フラボン誘導体

Country Status (1)

Country	Link
JP (1)	JPS6236391A (de)

1985
- 1985-08-09 JP JP17631085A patent/JPS6236391A/ja active Granted

Also Published As

Publication number	Publication date
JPS6236391A (ja)	1987-02-17

Publication	Publication Date	Title
SU820659A3 (ru)	1981-04-07	Способ получени производных 4-амино- 5-АлКилСульфОНилОАНизАМидОВ, иХ СОлЕй,ОКиСЕй, лЕВО- и пРАВОВРАщАющиХизОМЕРОВ /иХ ВАРиАНТы/
US4209623A (en)	1980-06-24	Pyrimidine-5-N-(1H-tetrazol-5-yl)-carboxamides
JP2793195B2 (ja)	1998-09-03	ベンゾチアゾール誘導体
WO1994029277A1 (en)	1994-12-22	AMILINO- OR PYRIDYLAMINO- CYCLOBUTENE- 1,2-DIONE DERIVATIVES AS cGMP PHOSPHODIESTERASE INHIBITORS
JP3122792B2 (ja)	2001-01-09	新規な活性化合物
HU220066B (hu)	2001-10-28	Imidazo[1,2-a]piridinek alkoxi-alkil-karbamátjai, alkalmazásuk, eljárás előállításukra és ezeket tartalmazó gyógyszerkészítmények
US5464849A (en)	1995-11-07	N-hydroxyurea derivatives as antiallergy and antiinflammatory agents
JPH0662562B2 (ja)	1994-08-17	ピロール酢酸アミド
EP0228959B1 (de)	1992-03-18	Aminostyryl-Verbindungen und diese als wirksame Bestandteile enthaltende leukotrienantagonistische Zusammensetzung und Verfahren um durch ihre Anwendung SRS entgegenzuwirken
JPH0568476B2 (de)	1993-09-29
JPS60193991A (ja)	1985-10-02	イミダゾキナゾリニルオキシアルキルアミド誘導体
JPS6183179A (ja)	1986-04-26	新規フラボン誘導体
JPH0473436B2 (de)	1992-11-20
KR900003649B1 (ko)	1990-05-28	(1H-테트라졸-5-일)테트라졸로[1,5-a]-퀴놀린의 제조방법
JPS6256874B2 (de)	1987-11-27
SU923369A3 (ru)	1982-04-23	Способ получени производных 5-/2-окси-3-тиопропокси/-хромон-2-уксусной кислоты или их солей со щелочными или щелочноземельными металлами
JPH0450310B2 (de)	1992-08-13
Holland et al.	1976	Cinnoline-3-propionic acids, a new series of orally active antiallergic substances
JPH0662608B2 (ja)	1994-08-17	カルボスチリル誘導体
SU1512482A3 (ru)	1989-09-30	Способ получени производных пиримидоизохинолина или их фармацевтически приемлемых солей
NL8003385A (nl)	1980-12-16	(3-alkylamino-2-hydroxypropoxy)-furan-2-carbonzuur- aniliden en werkwijzen voor het bereiden en toepassen van deze verbindingen.
US5292751A (en)	1994-03-08	5,7-dihydroxy-2-methyl-8-(4-(3-hydroxy-1-(1-propyl))piperidinyl)-4H-1-benzopyran-4-one, its preparation and its use
JP3553158B2 (ja)	2004-08-11	ピリダジノインドール誘導体
US6291482B1 (en)	2001-09-18	N-hydroxyurea derivative and pharmaceutical composition containing the same
JP3222428B2 (ja)	2001-10-29	Ｎ−ヒドロキシ尿素誘導体及びそれを含む医薬