CS244908B2 - Preparation method of 2,4-diamino-5-/3,4,5-trimethoxybenzyl/-pyramidine - Google Patents

Preparation method of 2,4-diamino-5-/3,4,5-trimethoxybenzyl/-pyramidine Download PDF

Info

Publication number: CS244908B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; guanidine; compound; reaction; reacting
Prior art date: 1981-06-26

Application number

CS824717A

Other languages

Czech (cs)

English (en)

Other versions

CS471782A2 (en

Inventor

Ivan Beck

Imre Biro

Andras Dietz

Elemer Jakfalvi

Laszlo Ladanyi

Istvan Simonyi

Zoltan Takacs

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1981-06-26

Filing date

1982-06-24

Publication date

1986-08-14

1982-06-24 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1985-09-17 Publication of CS471782A2 publication Critical patent/CS471782A2/cs

1986-08-14 Publication of CS244908B2 publication Critical patent/CS244908B2/cs

Links

238000002360 preparation method Methods 0.000 title claims abstract description 7
125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 title description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 30
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 15
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 15
238000000034 method Methods 0.000 claims abstract description 14
150000001875 compounds Chemical class 0.000 claims abstract description 11
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims abstract description 11
-1 ethylene glycol monoalkylether Chemical class 0.000 claims abstract description 8
238000002955 isolation Methods 0.000 claims abstract description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
229910052783 alkali metal Inorganic materials 0.000 claims abstract 3
RMKSZKNEPFLURM-UHFFFAOYSA-N 2-(methoxymethyl)-3-(3,4,5-trimethoxyphenyl)prop-2-enenitrile Chemical compound COCC(C#N)=CC1=CC(OC)=C(OC)C(OC)=C1 RMKSZKNEPFLURM-UHFFFAOYSA-N 0.000 claims abstract 2
OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
229960001082 trimethoprim Drugs 0.000 claims description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
239000011541 reaction mixture Substances 0.000 claims 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
239000002253 acid Substances 0.000 claims 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
150000003839 salts Chemical class 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 1
OOWFYDWAMOKVSF-UHFFFAOYSA-N 3-methoxypropanenitrile Chemical compound COCCC#N OOWFYDWAMOKVSF-UHFFFAOYSA-N 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
239000002585 base Substances 0.000 claims 1
238000009835 boiling Methods 0.000 claims 1
238000001816 cooling Methods 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
238000007363 ring formation reaction Methods 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
239000000725 suspension Substances 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract 1
230000000973 chemotherapeutic effect Effects 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
229940079593 drug Drugs 0.000 abstract 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 4
239000007859 condensation product Substances 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
150000008360 acrylonitriles Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CS824717A 1981-06-26 1982-06-24 Preparation method of 2,4-diamino-5-/3,4,5-trimethoxybenzyl/-pyramidine CS244908B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU811869A HU187370B (en)	1981-06-26	1981-06-26	Improved process for producing 2,4-diamino-5-bracket-3-comma above, 4-comma above,5-comma above-trimethoxy-benzyl-bracket closed-pyrimidine

Publications (2)

Publication Number	Publication Date
CS471782A2 CS471782A2 (en)	1985-09-17
CS244908B2 true CS244908B2 (en)	1986-08-14

Family

ID=10956594

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS824717A CS244908B2 (en)	1981-06-26	1982-06-24	Preparation method of 2,4-diamino-5-/3,4,5-trimethoxybenzyl/-pyramidine

Country Status (21)

Country	Link
JP (1)	JPS5838266A (de)
AT (1)	AT387961B (de)
AU (1)	AU547823B2 (de)
BE (1)	BE893611A (de)
CA (1)	CA1174679A (de)
CH (1)	CH648834A5 (de)
CS (1)	CS244908B2 (de)
DD (1)	DD202703A5 (de)
DK (1)	DK155434C (de)
ES (1)	ES513482A0 (de)
FI (1)	FI76790C (de)
FR (1)	FR2508450B1 (de)
GB (1)	GB2104508B (de)
GR (1)	GR76159B (de)
HU (1)	HU187370B (de)
IE (1)	IE53466B1 (de)
IL (1)	IL66132A (de)
IT (1)	IT1190889B (de)
SE (1)	SE451133B (de)
SU (1)	SU1145929A3 (de)
YU (1)	YU42774B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2602507B1 (fr) *	1986-08-08	1989-06-09	Sanofi Pharma	Procede de preparation de diamino-2,4 benzyl-5 pyrimidines

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB743221A (en) *	1953-05-26	1956-01-11	Wellcome Found	Improvements in or relating to the manufacture of acrylonitriles
DE1303727B (de) *	1959-09-03	1976-02-05	Ausscheidung aus: 14 45 176 The Wellcome Foundation Ltd., London	Alpha-Arylidensubstituierte Propioni-Irile
NL122146C (de) *	1960-09-02
US4033962A (en) *	1975-06-26	1977-07-05	Hoffman-La Roche Inc.	2,4-Diamino-pyrimidine derivatives and processes
DE2635765C3 (de) *	1976-08-09	1979-02-08	Ludwig Heumann & Co Gmbh, 8500 Nuernberg	Verfahren zur Herstellung von 2,4-EMamino-5-(3',4'r5'-trimethoxybenzyl)-pyrimidin
US4115650A (en) *	1976-11-17	1978-09-19	Hoffmann-La Roche Inc.	Process for preparing 2,4-diamino-5-(substituted benzyl)-pyrimidines
DE2730467A1 (de) *	1977-07-06	1979-01-18	Basf Ag	Benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel

1981
- 1981-06-26 HU HU811869A patent/HU187370B/hu not_active IP Right Cessation
1982
- 1982-06-23 SE SE8203914A patent/SE451133B/sv not_active IP Right Cessation
- 1982-06-23 BE BE1/10544A patent/BE893611A/fr not_active IP Right Cessation
- 1982-06-24 IT IT22035/82A patent/IT1190889B/it active
- 1982-06-24 SU SU823456294A patent/SU1145929A3/ru active
- 1982-06-24 GR GR68560A patent/GR76159B/el unknown
- 1982-06-24 IL IL66132A patent/IL66132A/xx unknown
- 1982-06-24 AT AT0244982A patent/AT387961B/de not_active IP Right Cessation
- 1982-06-24 GB GB08218310A patent/GB2104508B/en not_active Expired
- 1982-06-24 FI FI822268A patent/FI76790C/fi not_active IP Right Cessation
- 1982-06-24 CS CS824717A patent/CS244908B2/cs unknown
- 1982-06-25 DD DD82241097A patent/DD202703A5/de not_active IP Right Cessation
- 1982-06-25 YU YU1385/82A patent/YU42774B/xx unknown
- 1982-06-25 AU AU85346/82A patent/AU547823B2/en not_active Ceased
- 1982-06-25 DK DK288082A patent/DK155434C/da not_active IP Right Cessation
- 1982-06-25 CA CA000406060A patent/CA1174679A/en not_active Expired
- 1982-06-25 ES ES513482A patent/ES513482A0/es active Granted
- 1982-06-25 CH CH3908/82A patent/CH648834A5/de not_active IP Right Cessation
- 1982-06-25 FR FR8211151A patent/FR2508450B1/fr not_active Expired
- 1982-06-25 JP JP57109647A patent/JPS5838266A/ja active Pending
- 1982-06-25 IE IE1520/82A patent/IE53466B1/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT8222035A0 (it)	1982-06-24
IL66132A (en)	1985-04-30
AU547823B2 (en)	1985-11-07
ES8304949A1 (es)	1983-04-01
DK155434B (da)	1989-04-10
BE893611A (fr)	1982-12-23
FI76790B (fi)	1988-08-31
IE821520L (en)	1982-12-26
SE8203914D0 (sv)	1982-06-23
GR76159B (de)	1984-08-03
CH648834A5 (de)	1985-04-15
IL66132A0 (en)	1982-09-30
FI76790C (fi)	1988-12-12
SU1145929A3 (ru)	1985-03-15
IT1190889B (it)	1988-02-24
GB2104508A (en)	1983-03-09
GB2104508B (en)	1985-01-16
AT387961B (de)	1989-04-10
DK288082A (da)	1982-12-27
FI822268A0 (fi)	1982-06-24
HU187370B (en)	1985-12-28
AU8534682A (en)	1983-01-06
YU42774B (en)	1988-12-31
CS471782A2 (en)	1985-09-17
DD202703A5 (de)	1983-09-28
SE451133B (sv)	1987-09-07
ATA244982A (de)	1988-09-15
FI822268L (fi)	1982-12-27
FR2508450B1 (fr)	1986-01-03
YU138582A (en)	1984-10-31
CA1174679A (en)	1984-09-18
ES513482A0 (es)	1983-04-01
IE53466B1 (en)	1988-11-23
FR2508450A1 (fr)	1982-12-31
JPS5838266A (ja)	1983-03-05
SE8203914L (sv)	1982-12-27
DK155434C (da)	1989-09-18

Publication	Publication Date	Title
US4965362A (en)	1990-10-23	Joint preparation of 3-dialkylaminopropionitriles, bis-(2-cyanoethyl) ether and, if desired, ethylene-cyanohydrin
CS244908B2 (en)	1986-08-14	Preparation method of 2,4-diamino-5-/3,4,5-trimethoxybenzyl/-pyramidine
US3855265A (en)	1974-12-17	5-benzyl pyrimidines intermediates therefore, and method
US4125721A (en)	1978-11-14	Process for the production of 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)-pyrimidine
US2820050A (en)	1958-01-14	Substituted propionitriles and preparation of the same
US4620006A (en)	1986-10-28	Acid salts of 1-(cyanoalkyl)-4-guanylpiperazines
US4492792A (en)	1985-01-08	Process for preparing 4-amino-5-dialkoxy-methylpyrimidine derivatives
US5095133A (en)	1992-03-10	Process for the preparation of aminomethylene compounds
JP3031279B2 (ja)	2000-04-10	２−アルコキシ−６−（トリフルオロメチル）ピリミジン−４−オルの製造方法
US4789743A (en)	1988-12-06	Process for the preparation of 2,4-diamino-5-benzylpyrimidines
CS244907B2 (en)	1986-08-14	Preparation method of 2,4-diamino-5-/3,4,5-trimethoxybenzyl/-pyriminine
EP0103126A1 (de)	1984-03-21	Verfahren zur Herstellung von 4-Amino-5-dialkoxy-methylpyrimidinderivaten
US2839533A (en)	1958-06-17	Method for the preparation of piperazines
US1998102A (en)	1935-04-16	Secondaky-amyl allyl barbituric
KR930001338B1 (ko)	1993-02-26	아미노알킬로 치환된 모노올레핀화합물의 제조방법
JPS626706B2 (de)	1987-02-13
US5268498A (en)	1993-12-07	Synthesis-of α-aminonitriles with recycle of aqueous phase
CS274423B2 (en)	1991-04-11	Method of 8-(4-(4-(2-pyrimidinyl)-1-piperazinyl) butyl)-8-aza-spiro (4,5)-decane-7,9-dione preparation
US3153672A (en)	1964-10-20	Alkanone thioethers
JPS58128356A (ja)	1983-07-30	２−アルコキシメチレン−３，３−ジアルコキシブロパンニトリル類
JPH0344360A (ja)	1991-02-26	置換１，３―ジアミノプロパン
JPH04338353A (ja)	1992-11-25	α−アルキルアクロレインの製造方法
JPH05339267A (ja)	1993-12-21	新規なピリジン誘導体、その製造方法及びその中間体
CZ9400242A3 (cs)	2001-11-14	N-substituované deriváty N-methyl-3-(p-trifluoromethylfenoxy)-3-fenylpropylaminu a způsob jejich přípravy
JPH0432824B2 (de)	1992-06-01