JPS60155175A - 新規フタライド誘導体 - Google Patents

新規フタライド誘導体

Info

Publication number: JPS60155175A
Authority: JP; Japan
Prior art keywords: compound; formula; group; phthalide; ddd
Prior art date: 1983-12-26
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.): Granted

Application number

JP25198583A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0475235B2 (fr

Inventor

Yoshiyasu Fukuyama

愛保福山

Hiroyoshi Ou

王　普善

Nobuaki Kou

高　宣亮

Yoshio O

王　義雄

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.)

1983-12-26

Filing date

1983-12-26

Publication date

1985-08-15

1983-12-26 Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd

1983-12-26 Priority to JP25198583A priority Critical patent/JPS60155175A/ja

1985-08-15 Publication of JPS60155175A publication Critical patent/JPS60155175A/ja

1992-11-30 Publication of JPH0475235B2 publication Critical patent/JPH0475235B2/ja

Status Granted legal-status Critical Current

Links

125000005506 phthalide group Chemical class 0.000 title claims abstract description 9
125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 3
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
150000001875 compounds Chemical class 0.000 abstract description 44
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 12
239000012535 impurity Substances 0.000 abstract description 3
238000002360 preparation method Methods 0.000 abstract description 3
239000003416 antiarrhythmic agent Substances 0.000 abstract description 2
230000003177 cardiotonic effect Effects 0.000 abstract description 2
238000007796 conventional method Methods 0.000 abstract description 2
239000000706 filtrate Substances 0.000 abstract description 2
229910052799 carbon Inorganic materials 0.000 abstract 2
206010002383 Angina Pectoris Diseases 0.000 abstract 1
241000533367 Cnidium officinale Species 0.000 abstract 1
239000003218 coronary vasodilator agent Substances 0.000 abstract 1
238000001914 filtration Methods 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
239000000284 extract Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000001228 spectrum Methods 0.000 description 9
238000010586 diagram Methods 0.000 description 8
238000000605 extraction Methods 0.000 description 8
230000000704 physical effect Effects 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000008280 blood Substances 0.000 description 7
210000004369 blood Anatomy 0.000 description 7
239000000203 mixture Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
-1 methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, pentyloxy Chemical group 0.000 description 6
210000003205 muscle Anatomy 0.000 description 6
238000005917 acylation reaction Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
230000000638 stimulation Effects 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000000862 absorption spectrum Methods 0.000 description 4
230000001746 atrial effect Effects 0.000 description 4
150000007514 bases Chemical class 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000000034 method Methods 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000017531 blood circulation Effects 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 3
229920000669 heparin Polymers 0.000 description 3
229960001008 heparin sodium Drugs 0.000 description 3
239000005457 ice water Substances 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
210000003540 papillary muscle Anatomy 0.000 description 3
239000000052 vinegar Substances 0.000 description 3
235000021419 vinegar Nutrition 0.000 description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241001061260 Emmelichthys struhsakeri Species 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
210000004351 coronary vessel Anatomy 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012156 elution solvent Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
241000411851 herbal medicine Species 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
XLFDJKJEYMKLJX-YFHOEESVSA-N (Z)-3-butylidene-7-hydroxyphthalide Chemical compound C1=CC=C(O)C2=C1C(=C/CCC)/OC2=O XLFDJKJEYMKLJX-YFHOEESVSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
ZPIKVDODKLJKIN-UHFFFAOYSA-N 3-butyl-4,5-dihydro-3h-2-benzofuran-1-one Chemical compound C1CC=CC2=C1C(CCCC)OC2=O ZPIKVDODKLJKIN-UHFFFAOYSA-N 0.000 description 1
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 1
206010002091 Anaesthesia Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000282465 Canis Species 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241001397173 Kali <angiosperm> Species 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241000700159 Rattus Species 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
ZPIKVDODKLJKIN-NSHDSACASA-N Senkyunolide A Natural products C1CC=CC2=C1[C@H](CCCC)OC2=O ZPIKVDODKLJKIN-NSHDSACASA-N 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
NELWQUQCCZMRPB-UBPLGANQSA-N [(2r,3r,4r,5r)-4-acetyloxy-5-(4-amino-5-ethenyl-2-oxopyrimidin-1-yl)-2-methyloxolan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](C)O[C@H]1N1C(=O)N=C(N)C(C=C)=C1 NELWQUQCCZMRPB-UBPLGANQSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
238000001042 affinity chromatography Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
230000001640 apoptogenic effect Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000008321 arterial blood flow Effects 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
238000006480 benzoylation reaction Methods 0.000 description 1
230000037396 body weight Effects 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000496 cardiotonic agent Substances 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
229940125890 compound Ia Drugs 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
210000004709 eyebrow Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
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 1
230000001965 increasing effect Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
210000004731 jugular vein Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000008023 pharmaceutical filler Substances 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
210000005245 right atrium Anatomy 0.000 description 1
210000005241 right ventricle Anatomy 0.000 description 1
XLFDJKJEYMKLJX-UHFFFAOYSA-N senkyunolide-B Natural products C1=CC=C(O)C2=C1C(=CCCC)OC2=O XLFDJKJEYMKLJX-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000001013 sinoatrial node Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Furan Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP25198583A 1983-12-26 1983-12-26 新規フタライド誘導体 Granted JPS60155175A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP25198583A JPS60155175A (ja)	1983-12-26	1983-12-26	新規フタライド誘導体

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP25198583A JPS60155175A (ja)	1983-12-26	1983-12-26	新規フタライド誘導体

Publications (2)

Publication Number	Publication Date
JPS60155175A true JPS60155175A (ja)	1985-08-15
JPH0475235B2 JPH0475235B2 (fr)	1992-11-30

Family

ID=17230937

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP25198583A Granted JPS60155175A (ja)	1983-12-26	1983-12-26	新規フタライド誘導体

Country Status (1)

Country	Link
JP (1)	JPS60155175A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS617267A (ja) *	1984-06-20	1986-01-13	Otsuka Pharmaceut Co Ltd	新規フタライド誘導体

1983
- 1983-12-26 JP JP25198583A patent/JPS60155175A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS617267A (ja) *	1984-06-20	1986-01-13	Otsuka Pharmaceut Co Ltd	新規フタライド誘導体

Also Published As

Publication number	Publication date
JPH0475235B2 (fr)	1992-11-30

Publication	Publication Date	Title
Yamagishi et al.	1988	The cytotoxic principles of Hyptis capitata and the structures of the new triterpenes hyptatic acid-A and-B
Kupchan et al.	1977	Tumor inhibitors. 122. The maytansinoids. Isolation, structural elucidation, and chemical interrelation of novel ansa macrolides
JPH07504664A (ja)	1995-05-25	ハリコンドリン類およびその関連化合物
US4885280A (en)	1989-12-05	Novel 14-amino steroids
CN105732381A (zh)	2016-07-06	牛樟芝提取物及其制备方法和应用
Joshi et al.	1992	Saponins from Collinsonia canadensis
Horton et al.	1970	Synthesis and reactions of unsaturated sugars. XI. Evidence for a carbenoid intermediate in the Corey-Winter alkene synthesis
JPH0248533A (ja)	1990-02-19	ノブドウ根抽出物よりなる肝疾患治療剤
WO1999000349A1 (fr)	1999-01-07	Derives de cyclopentenone
JPS60155175A (ja)	1985-08-15	新規フタライド誘導体
Reich	1939	A method for the separation of sugars by the chromatographic adsorption of their coloured esters: Separation of glucose and fructose
PT91362B (pt)	1995-03-31	Processo para a preparacao de novos acidos 6-fluor-3,5-di-hidroxi-carboxilicos e seus derivados, e de composicoes farmaceuticas que os contem e de produtos intermediarios
JPS617267A (ja)	1986-01-13	新規フタライド誘導体
JPH041751B2 (fr)	1992-01-14
JPS62209070A (ja)	1987-09-14	ネオリグナン誘導体
CA1304359C (fr)	1992-06-30	Compositions antitumorales et antivirales d'origine marine
Richtmyer et al.	1962	Crystalline D-glycero-D-gulo-Octulose
JPS5831352B2 (ja)	1983-07-05	新規なインド−ル誘導体、その製造方法及び医薬としての使用
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Stanger et al.	1944	The Unsaponifiable Residue of Human Liver. I. Preparation and Primary Chromatographic Fractionation1
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JPS60155175A - 新規フタライド誘導体 - Google Patents

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Priority Applications (1)

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Publications (2)

Family

ID=17230937

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

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