SU1020003A3 - Способ получени производных пиримидона - Google Patents

Способ получени производных пиримидона Download PDF

Info

Publication number: SU1020003A3
Authority: SU; USSR - Soviet Union
Prior art keywords: pyrimidone; mixture; methyl; mannich; residue
Prior art date: 1978-11-13

Application number

SU813261990A

Other languages

English (en)

Russian (ru)

Inventor

Генри Браун Томас

Джон Айф Роберт

Original Assignee

Смит Клайн Энд Френч Лабораториз Лтд (Фирма)

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.)

1978-11-13

Filing date

1981-03-24

Publication date

1983-05-23

1981-03-24 Application filed by Смит Клайн Энд Френч Лабораториз Лтд (Фирма) filed Critical Смит Клайн Энд Френч Лабораториз Лтд (Фирма)

1983-05-23 Application granted granted Critical

1983-05-23 Publication of SU1020003A3 publication Critical patent/SU1020003A3/ru

Links

150000008318 pyrimidones Chemical class 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title claims 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 9
239000003153 chemical reaction reagent Substances 0.000 claims description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
HYHSFFFCLDOXCJ-UHFFFAOYSA-N dimethyl(methylidene)azanium Chemical class C[N+](C)=C HYHSFFFCLDOXCJ-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
-1 {3-pyridylmethyl) -pyrimidone Chemical compound 0.000 description 9
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
239000007787 solid Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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
239000008346 aqueous phase Substances 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
230000028327 secretion Effects 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
KWBSLRQDOHBJPQ-UHFFFAOYSA-N n-[5-[(6-methylpyridin-3-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound C1=NC(C)=CC=C1CC1=CN=C(N[N+]([O-])=O)NC1=O KWBSLRQDOHBJPQ-UHFFFAOYSA-N 0.000 description 2
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
150000008081 1H-pyrimidin-4-ones Chemical class 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
ZTBZXZSFKHHOQA-UHFFFAOYSA-N 5-[(6-methylpyridin-3-yl)methyl]-1h-pyrimidin-6-one Chemical compound C1=NC(C)=CC=C1CC1=CN=CNC1=O ZTBZXZSFKHHOQA-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
238000006683 Mannich reaction Methods 0.000 description 1
235000010678 Paulownia tomentosa Nutrition 0.000 description 1
240000002834 Paulownia tomentosa Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
238000005902 aminomethylation reaction Methods 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
ZJTROANVDZIEGB-UHFFFAOYSA-M dimethyl(methylidene)azanium;chloride Chemical compound [Cl-].C[N+](C)=C ZJTROANVDZIEGB-UHFFFAOYSA-M 0.000 description 1
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical class N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000013049 sediment Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1

Landscapes

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

SU813261990A 1978-11-13 1981-03-24 Способ получени производных пиримидона SU1020003A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7844259		1978-11-13

Publications (1)

Publication Number	Publication Date
SU1020003A3 true SU1020003A3 (ru)	1983-05-23

Family

ID=10501003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU813261990A SU1020003A3 (ru)	1978-11-13	1981-03-24	Способ получени производных пиримидона

Country Status (2)

Country	Link
PL (1)	PL124279B1 (pl)
SU (1)	SU1020003A3 (pl)

1979
- 1979-02-12 PL PL22319079A patent/PL124279B1/pl unknown
1981
- 1981-03-24 SU SU813261990A patent/SU1020003A3/ru active

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
1. Вейганд-Хильгетаг. Методы эксперимента в органической химии. М., Хими , 1968, с. 756. . *

Also Published As

Publication number	Publication date
PL124279B1 (en)	1983-01-31

Publication	Publication Date	Title
EP0502169B1 (en)	1996-01-03	Piperazine derivatives
FI62668B (fi)	1982-10-29	Foerfarande foer framstaellning av h1- och h2-histaminantagonistiska 2-amino-4-pyrimidonderivat
EP3447051A1 (en)	2019-02-27	Method for preparing tyrosine kinase inhibitor and derivative thereof
NL8203410A (nl)	1983-04-05	Alkanoylaniliden.
EP0068834B1 (en)	1986-09-03	Pyrimidinone derivatives and pharmaceutical compositions containing them
SU906376A3 (ru)	1982-02-15	Способ получени производных 2-нитроаминопиримидона-4
Heyde et al.	2000	A Simple Route to N, N‐Dialkyl Derivatives of 2‐Amino‐5‐thiophenecarboxylates
NO762661L (pl)	1977-02-01
SU1436873A3 (ru)	1988-11-07	Способ получени производных 1,2,4-триазолокарбамата или их кислотно-аддитивных солей
AU644295B2 (en)	1993-12-02	2-aminopyrimidine-4-carboxamide derivatives, their preparation and their use in therapeutics
SU1020003A3 (ru)	1983-05-23	Способ получени производных пиримидона
KR840001953B1 (ko)	1984-10-26	벤조구아나민 유도체의 제조법
SU1033003A3 (ru)	1983-07-30	Способ получени производных 4-пиримидона или их фармацевтически приемлемых кислотно-аддитивных солей
US4514408A (en)	1985-04-30	N-substituted nicotinamide 1-oxide as histamine H2 receptor blockers
US3072648A (en)	1963-01-08	X-phenyl-s
CN110294768A (zh)	2019-10-01	一种通过2,6-二乙基-4-甲基苯丙二酸酯合成唑啉草酯的方法
US2459367A (en)	1949-01-18	1,4-di (heterocyclic substituted) piperazines
NO781618L (no)	1978-11-10	Fremgangsmaate ved fremstilling av nye chromenderivater
SU607547A3 (ru)	1978-05-15	Способ получени производных гидразина
PL91000B1 (en)	1977-02-28	Process for the manufacture of indole derivatives [gb1407658a]
HU192951B (en)	1987-08-28	Process for producing pyrimidine derivatives of anti-ulcer activity
CA1177485A (en)	1984-11-06	3'-substituted-5'-(2-amino-4-pyridyl)-1',2',4'- triazoles
US4469871A (en)	1984-09-04	Process for preparing 2-(lower-alkoxy)-1-(pyridinyl) ethenyl lower-alkyl ketones
US5198441A (en)	1993-03-30	Derivatives of 1,2-dihydro 2-oxo quinoxalines, their preparation and their use in therapy
SU659089A3 (ru)	1979-04-25	Способ получени производных 2-окси-3-аминопропана или их -окисей или солей