FI65991C - Foerfarande foer framstaellning av terapeutiskt vaerdefull 5((3,4,5-trimetoxifenyl)metyl)-2,4-pyrimidindiamin - Google Patents

Foerfarande foer framstaellning av terapeutiskt vaerdefull 5((3,4,5-trimetoxifenyl)metyl)-2,4-pyrimidindiamin Download PDF

Info

Publication number: FI65991C
Authority: FI; Finland
Prior art keywords: formula; ch3o; methyl; pyrimidinediamine; guanidine
Prior art date: 1981-05-28

Application number

FI811638A

Other languages

English (en)

Finnish (fi)

Other versions

FI65991B (fi

FI811638A0 (fi

Inventor

Lasse Antero Koskenniska

Kalle Johannes Manninen

Original Assignee

Farmos Oy

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.)

1981-05-28

Filing date

1981-05-28

Publication date

1984-08-10

1981-05-28 Application filed by Farmos Oy filed Critical Farmos Oy

1981-05-28 Priority to FI811638A priority Critical patent/FI65991C/fi

1981-05-28 Publication of FI811638A0 publication Critical patent/FI811638A0/fi

1982-05-27 Priority to EP82302762A priority patent/EP0067593A1/fr

1984-04-30 Publication of FI65991B publication Critical patent/FI65991B/fi

1984-08-10 Application granted granted Critical

1984-08-10 Publication of FI65991C publication Critical patent/FI65991C/fi

Links

238000000034 method Methods 0.000 title claims description 21
230000001225 therapeutic effect Effects 0.000 title 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 title 1
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 22
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 description 13
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 11
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 11
OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
239000007859 condensation product Substances 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
239000002798 polar solvent Substances 0.000 claims description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
229940093475 2-ethoxyethanol Drugs 0.000 claims description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 claims description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
229960001760 dimethyl sulfoxide Drugs 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
210000005036 nerve Anatomy 0.000 claims 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 description 12
229960004198 guanidine Drugs 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
229960001082 trimethoprim Drugs 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
-1 trimethoprim Chemical compound 0.000 description 4
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000002357 guanidines Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
UCTUXUGXIFRVGX-UHFFFAOYSA-N 2,3,4-trimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1OC UCTUXUGXIFRVGX-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical group NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
IKBDDJBJHSLINR-UHFFFAOYSA-N 3-[2-(2-cyanoethylamino)anilino]propanenitrile Chemical compound N#CCCNC1=CC=CC=C1NCCC#N IKBDDJBJHSLINR-UHFFFAOYSA-N 0.000 description 1
KRGHODFKRQTYQA-UHFFFAOYSA-N 3-[3-(2-cyanoethylamino)anilino]propanenitrile Chemical compound N#CCCNC1=CC=CC(NCCC#N)=C1 KRGHODFKRQTYQA-UHFFFAOYSA-N 0.000 description 1
QXQYJEMSNUMUPO-UHFFFAOYSA-N 3-[4-(2-cyanoethyl)piperazin-1-yl]propanenitrile Chemical compound N#CCCN1CCN(CCC#N)CC1 QXQYJEMSNUMUPO-UHFFFAOYSA-N 0.000 description 1
238000006418 Brown reaction Methods 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
229960000789 guanidine hydrochloride Drugs 0.000 description 1
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
229940018564 m-phenylenediamine Drugs 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
150000004987 o-phenylenediamines Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

FI811638A 1981-05-28 1981-05-28 Foerfarande foer framstaellning av terapeutiskt vaerdefull 5((3,4,5-trimetoxifenyl)metyl)-2,4-pyrimidindiamin FI65991C (fi)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
FI811638A FI65991C (fi)	1981-05-28	1981-05-28	Foerfarande foer framstaellning av terapeutiskt vaerdefull 5((3,4,5-trimetoxifenyl)metyl)-2,4-pyrimidindiamin
EP82302762A EP0067593A1 (fr)	1981-05-28	1982-05-27	Procédé de préparation de triméthoprim et intermédiaires utilisés dans ce but

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FI811638A FI65991C (fi)	1981-05-28	1981-05-28	Foerfarande foer framstaellning av terapeutiskt vaerdefull 5((3,4,5-trimetoxifenyl)metyl)-2,4-pyrimidindiamin
FI811638		1981-05-28

Publications (3)

Publication Number	Publication Date
FI811638A0 FI811638A0 (fi)	1981-05-28
FI65991B FI65991B (fi)	1984-04-30
FI65991C true FI65991C (fi)	1984-08-10

Family

ID=8514434

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI811638A FI65991C (fi)	1981-05-28	1981-05-28	Foerfarande foer framstaellning av terapeutiskt vaerdefull 5((3,4,5-trimetoxifenyl)metyl)-2,4-pyrimidindiamin

Country Status (2)

Country	Link
EP (1)	EP0067593A1 (fr)
FI (1)	FI65991C (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6593487B1 (en)	2001-12-19	2003-07-15	Air Products And Chemicals, Inc.	N-cyanoethylated ortho and meta toluenediamine compounds
US6441238B1 (en)	2001-12-19	2002-08-27	Air Products And Chemicals, Inc.	N-(aminopropyl)-toluenediamines and their use as epoxy curing agents

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1261455A (en) *	1969-03-06	1972-01-26	Burroughs Wellcome Co	Improvements in or relating to substituted acrylonitriles
DE2612891A1 (de) *	1976-03-26	1977-10-20	Smithkline Dauelsberg	Verfahren zur herstellung von 2,4-diamino-5-benzyl-pyrimidinen
JPS5465747A (en) *	1977-11-04	1979-05-26	Motoo Takayanagi	High molecular composite body

1981
- 1981-05-28 FI FI811638A patent/FI65991C/fi not_active IP Right Cessation
1982
- 1982-05-27 EP EP82302762A patent/EP0067593A1/fr not_active Ceased

Also Published As

Publication number	Publication date
EP0067593A1 (fr)	1982-12-22
FI65991B (fi)	1984-04-30
FI811638A0 (fi)	1981-05-28

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: FARMOS-YHTYMAE OY

Publication	Publication Date	Title
US4323570A (en)	1982-04-06	Substituted aminopyrimidines
KR920000761B1 (ko)	1992-01-21	치환된 2-피리미디닐-1-피페라진 유도체의 제조방법
Naik et al.	2007	Studies on synthesis of pyrimidine derivatives and their pharmacological evaluation
US4559345A (en)	1985-12-17	Pyrimidine and s-triazine derivatives with antilipidemic activity
CA1070691A (fr)	1980-01-29	Derives de la guanidine
Fishbein et al.	1954	The preparation and reactions of 2-Alkyl-1-(or 3)-nitro-2-thiopseudourea. Part I. Reaction with Amines1
FI109119B (fi)	2002-05-31	N-(2-amino-4,6-diklooripyrimidin-5-yyli)formamidi, menetelmä sen valmistamiseksi sekä menetelmän välituote
FI62071C (fi)	1982-11-10	Foerfarande foer framstaellning av antitumoeraktiva 1-asyloximetyl-5-fluoruracilderivat
SE409031B (sv)	1979-07-23	Forfarande for framstellning av vissa angivna n-substituerade-beta-amino-alfa-bensylakrylnitrilderivat av hog renhet
Nishigaki et al.	1969	Synthetic antibacterials. I. Nitrofurylvinyl-s-triazine derivatives
FI65991B (fi)	1984-04-30	Foerfarande foer framstaellning av terapeutiskt vaerdefull 5-((3,4,5-trimetoxifenyl)metyl)-2,4-pyrimidindiamin
US4150154A (en)	1979-04-17	Amidinoureas
US4226867A (en)	1980-10-07	3,3-Substituted spiro-1,2,4-benzothiadiazines
US4288595A (en)	1981-09-08	7-(Substituted)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamines
US3184460A (en)	1965-05-18	1-(alkoxyphenylalkyl)-2-imidazolinones, -2-imidazolidinones and -2-pyrimidinones
Haruki et al.	1968	Some reactions of N-haloamidines
CA1037953A (fr)	1978-09-05	Diamino-2,4 benzylpirimidines-5
IL43280A (en)	1977-06-30	Preparation of(substituted phenylamidino)urea derivatives pharmaceutical compositions containing them and some new such derivatives
JPS6254111B2 (fr)	1987-11-13
Russell et al.	1952	The formation of 1, 3, 5-triazines by the reaction of α-cyanocarbonyl compounds with guanidine
JPH02115167A (ja)	1990-04-27	オキシグアニジンの製造方法
US3873530A (en)	1975-03-25	Novel immonium salts
US4180578A (en)	1979-12-25	2,4-Diamino-5-(4'-methylthio)benzylpyrimidenes, compounds, compositions and method of use
US5185341A (en)	1993-02-09	Substituted 5-(phenoxyalkanoylamino)-uracil compounds, methods for making same and pharmaceutical compositions based on same
HU188074B (en)	1986-03-28	Process for the preparation of cimetidin