JPH0427982B2 - - Google Patents

Info

Publication number: JPH0427982B2
Authority: JP; Japan
Prior art keywords: group; methyl; dihydro; pyrimidone; ethoxycarbonyl
Prior art date: 1983-08-10
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

JP14599683A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6038368A (ja

Inventor

Hidetsura Cho

Yoshiko Oonaka

Fumio Sato

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.)

Suntory Ltd

Original Assignee

Suntory 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.)

1983-08-10

Filing date

1983-08-10

Publication date

1992-05-13

1983-08-10 Application filed by Suntory Ltd filed Critical Suntory Ltd

1983-08-10 Priority to JP14599683A priority Critical patent/JPS6038368A/ja

1985-02-27 Publication of JPS6038368A publication Critical patent/JPS6038368A/ja

1992-05-13 Publication of JPH0427982B2 publication Critical patent/JPH0427982B2/ja

Status Granted legal-status Critical Current

Links

-1 trifluoromethyl phenyl group Chemical group 0.000 claims description 100
IHXNIOYEXQWUNI-UHFFFAOYSA-N 4,5-dihydro-1h-pyrimidin-6-one Chemical class O=C1CCN=CN1 IHXNIOYEXQWUNI-UHFFFAOYSA-N 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
238000010438 heat treatment Methods 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
125000005037 alkyl phenyl group Chemical group 0.000 claims 1
125000004799 bromophenyl group Chemical group 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000000068 chlorophenyl group Chemical group 0.000 claims 1
125000004802 cyanophenyl group Chemical group 0.000 claims 1
125000004188 dichlorophenyl group Chemical group 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000001207 fluorophenyl group Chemical group 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000006501 nitrophenyl group Chemical group 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
125000003545 alkoxy group Chemical group 0.000 description 26
239000000203 mixture Substances 0.000 description 25
238000010992 reflux Methods 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 19
238000002329 infrared spectrum Methods 0.000 description 19
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 16
238000011282 treatment Methods 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
239000013078 crystal Substances 0.000 description 13
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
238000010898 silica gel chromatography Methods 0.000 description 10
238000000034 method Methods 0.000 description 7
238000001228 spectrum Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000012230 colorless oil Substances 0.000 description 6
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
239000012156 elution solvent Substances 0.000 description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
239000012046 mixed solvent Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
239000003480 eluent Substances 0.000 description 4
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
206010002383 Angina Pectoris Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 description 2
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
229940127291 Calcium channel antagonist Drugs 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
230000006793 arrhythmia Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
239000003218 coronary vasodilator agent Substances 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
UCTUXUGXIFRVGX-UHFFFAOYSA-N 2,3,4-trimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1OC UCTUXUGXIFRVGX-UHFFFAOYSA-N 0.000 description 1
LLMLNAVBOAMOEE-UHFFFAOYSA-N 2,3-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1Cl LLMLNAVBOAMOEE-UHFFFAOYSA-N 0.000 description 1
MCIDYUGTJBLEST-UHFFFAOYSA-N 2,3-dinitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1[N+]([O-])=O MCIDYUGTJBLEST-UHFFFAOYSA-N 0.000 description 1
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
NTWBHJYRDKBGBR-UHFFFAOYSA-N 2-ethylbenzaldehyde Chemical compound CCC1=CC=CC=C1C=O NTWBHJYRDKBGBR-UHFFFAOYSA-N 0.000 description 1
ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
QVTPWONEVZJCCS-UHFFFAOYSA-N 2-formylbenzonitrile Chemical compound O=CC1=CC=CC=C1C#N QVTPWONEVZJCCS-UHFFFAOYSA-N 0.000 description 1
CTUPBAXICGISQP-UHFFFAOYSA-N 2-methylthiobenzaldehyde Chemical compound CC1=CC=CC=C1C=S CTUPBAXICGISQP-UHFFFAOYSA-N 0.000 description 1
CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
WKHILFGJMAXBNZ-UHFFFAOYSA-N 3-chloro-2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C=O WKHILFGJMAXBNZ-UHFFFAOYSA-N 0.000 description 1
JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 description 1
206010003225 Arteriospasm coronary Diseases 0.000 description 1
208000003890 Coronary Vasospasm Diseases 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000000480 calcium channel blocker Substances 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
201000011634 coronary artery vasospasm Diseases 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
SVKFJFJTWYOZCB-UHFFFAOYSA-N diethyl 2-[(2-methoxyphenyl)methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CC1=CC=CC=C1OC SVKFJFJTWYOZCB-UHFFFAOYSA-N 0.000 description 1
MQONNZMFYJTYMF-UHFFFAOYSA-N diethyl 2-[(4-methylsulfanylphenyl)methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CC1=CC=C(SC)C=C1 MQONNZMFYJTYMF-UHFFFAOYSA-N 0.000 description 1
VUWPIBNKJSEYIN-UHFFFAOYSA-N diethyl 2-benzylidenepropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CC1=CC=CC=C1 VUWPIBNKJSEYIN-UHFFFAOYSA-N 0.000 description 1
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
229960004166 diltiazem Drugs 0.000 description 1
LKLMASCOTOBEMT-UHFFFAOYSA-N dimethyl 2-[(2-nitrophenyl)methylidene]propanedioate Chemical compound COC(=O)C(C(=O)OC)=CC1=CC=CC=C1[N+]([O-])=O LKLMASCOTOBEMT-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
MSSAFCYKWMNVMZ-UHFFFAOYSA-N ethyl 3-(3-bromophenyl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=CC(Br)=C1 MSSAFCYKWMNVMZ-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000011597 hartley guinea pig Methods 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
239000002547 new drug Substances 0.000 description 1
229960001783 nicardipine Drugs 0.000 description 1
229960001597 nifedipine Drugs 0.000 description 1
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000004810 partition chromatography Methods 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
229960001722 verapamil Drugs 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP14599683A 1983-08-10 1983-08-10 ５，６−ジヒドロ−４−ピリミドン誘導体およびその製造法 Granted JPS6038368A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP14599683A JPS6038368A (ja)	1983-08-10	1983-08-10	５，６−ジヒドロ−４−ピリミドン誘導体およびその製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP14599683A JPS6038368A (ja)	1983-08-10	1983-08-10	５，６−ジヒドロ−４−ピリミドン誘導体およびその製造法

Publications (2)

Publication Number	Publication Date
JPS6038368A JPS6038368A (ja)	1985-02-27
JPH0427982B2 true JPH0427982B2 (fr)	1992-05-13

Family

ID=15397743

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP14599683A Granted JPS6038368A (ja)	1983-08-10	1983-08-10	５，６−ジヒドロ−４−ピリミドン誘導体およびその製造法

Country Status (1)

Country	Link
JP (1)	JPS6038368A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6064967A (ja) *	1983-09-20	1985-04-13	Suntory Ltd	ジヒドロピリミジン誘導体およびその製造法
US5506219A (en) *	1988-08-29	1996-04-09	E. R. Squibb & Sons, Inc.	Pyridine anchors for HMG-CoA reductase inhibitors

1983
- 1983-08-10 JP JP14599683A patent/JPS6038368A/ja active Granted

Also Published As

Publication number	Publication date
JPS6038368A (ja)	1985-02-27

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