GB957797A - Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates therefor - Google Patents
Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates thereforInfo
- Publication number
- GB957797A GB957797A GB30102/59A GB3010259A GB957797A GB 957797 A GB957797 A GB 957797A GB 30102/59 A GB30102/59 A GB 30102/59A GB 3010259 A GB3010259 A GB 3010259A GB 957797 A GB957797 A GB 957797A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- alkoxy
- diamino
- electrophilic
- nitriles
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 title abstract 2
- 239000000543 intermediate Substances 0.000 title 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical class CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003230 pyrimidines Chemical class 0.000 abstract 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DENDAT1303727D DE1303727B (de) | 1959-09-03 | Alpha-Arylidensubstituierte Propioni-Irile | |
| GB30102/59A GB957797A (en) | 1959-09-03 | 1959-09-03 | Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates therefor |
| IT13817/60A IT1061608B (it) | 1959-09-03 | 1960-08-06 | Metodo per la preparazione di 2.4 diammino 5 arilmetilpirimidine e composti cosi ottenuti |
| ES0260242A ES260242A1 (es) | 1959-09-03 | 1960-08-08 | Un metodo para hacer 2,4-diamino-5-arilmetil-piridinas |
| DE19601795586 DE1795586C3 (de) | 1959-09-03 | 1960-08-12 | Verfahren zur Herstellung von 2,4-Diamino-5-benzyl-pyrimidinen |
| DE1445176A DE1445176C3 (de) | 1959-09-03 | 1960-08-12 | Verfahren zur Herstellung von 2,4-Diamino-5-benzyl-pyrimidinen |
| AT656060A AT230379B (de) | 1959-09-03 | 1960-08-29 | Verfahren zur Herstellung von 2,4-Diamino-5-arylmethylpyrimidinen |
| CH996260A CH418338A (de) | 1959-09-03 | 1960-09-02 | Verfahren zur Herstellung von 2,4-Diamino-5-arylmethylpyrimidinen |
| SE836660A SE219368C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1959-09-03 | 1960-09-02 | |
| FI1465/60A FI42960B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1959-09-03 | 1960-09-03 | |
| MY196661A MY6600061A (en) | 1959-09-03 | 1966-12-31 | Method for making 2, 4-diamino-5-arylmethyl pyrimidines and intermediates therefor |
| FI68670A FI49156C (fi) | 1959-09-03 | 1970-03-13 | Propionitriilijohdannaiset, jotka ovat välituotteita farmaseuttisesti arvokkaiden 2,4-diamino-5-bentsyylipyrimidiinien valmistuksessa, ja me netelmä niiden valmistamiseksi. |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30102/59A GB957797A (en) | 1959-09-03 | 1959-09-03 | Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates therefor |
| GB3956059 | 1959-11-20 | ||
| GB2410160 | 1960-07-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB957797A true GB957797A (en) | 1964-05-13 |
Family
ID=27258299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30102/59A Expired GB957797A (en) | 1959-09-03 | 1959-09-03 | Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates therefor |
Country Status (8)
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3461206A (en) * | 1964-11-12 | 1969-08-12 | Hoffmann La Roche | Compositions containing a sulfanilamide and a 2,4-diamino-5-(2',4',5'-trisubstitutedbenzyl)pyrimidine |
| DE2010166A1 (de) * | 1969-03-06 | 1970-09-17 | The Wellcome Foundation Ltd., London | Stabilisierte alpha-Benzylaerylnitrile, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE2065367A1 (de) * | 1969-03-06 | 1973-05-24 | Wellcome Found | Verfahren zur herstellung von 2,4diamino-5-benzylpyrimidinen |
| US3852276A (en) * | 1969-03-06 | 1974-12-03 | Burroughs Wellcome Co | 5-benzyl pyrimidines intermediate therefore, and method |
| US3855265A (en) * | 1969-03-06 | 1974-12-17 | Burroughs Wellcome Co | 5-benzyl pyrimidines intermediates therefore, and method |
| US3950378A (en) * | 1969-03-06 | 1976-04-13 | Burroughs Wellcome Co. | Preparation of β-anilino-α-benzylacrylonitriles |
| US3991050A (en) * | 1969-03-06 | 1976-11-09 | Burroughs Wellcome Co. | Preparation of β-Amino-α-benzylacrylonitriles |
| US3998814A (en) | 1969-03-06 | 1976-12-21 | Burroughs Wellcome Co. | Process for preparing β-amino-α-benzylacrylonitriles |
| US4052553A (en) * | 1969-03-06 | 1977-10-04 | Burroughs Wellcome Co. | 5-benzyl pyrimidines intermediates therefore, and method |
| US4116958A (en) * | 1971-10-12 | 1978-09-26 | Burroughs Wellcome Co. | Organic synthetic methods benzylpyrimidine derivatives |
| US4137411A (en) * | 1977-02-04 | 1979-01-30 | Hoffmann-La Roche Inc. | Preparation of 2,4-diamino-5-(4-amino-3,5-substituted-benzyl)-pyrimidines |
| US4180578A (en) | 1977-05-09 | 1979-12-25 | Ludwig Heumann, & Co. GmbH | 2,4-Diamino-5-(4'-methylthio)benzylpyrimidenes, compounds, compositions and method of use |
| US4251454A (en) | 1974-12-24 | 1981-02-17 | Hoffmann-La Roche Inc. | Benzylpyrimidines |
| EP0051879A3 (en) * | 1980-11-11 | 1982-08-04 | The Wellcome Foundation Limited | Substituted pyrimidines, their synthesis and compositions containing them, their use in medicine and intermediates for making them |
| EP0096214A1 (en) * | 1982-05-01 | 1983-12-21 | The Wellcome Foundation Limited | Antibacterial pyrimidine compounds |
| US4587341A (en) * | 1982-05-07 | 1986-05-06 | Burroughs Wellcome Co. | 2,4-diamino-5-(1,2,3,4-tetrahydro-(substituted or unsubstituted)-6-quinolylmethyl)pyrimidines, useful as antimicrobials |
| AT384023B (de) * | 1980-11-11 | 1987-09-25 | Wellcome Found | Verfahren zur herstellung von neuen 2,4-diamino-5-(subst.)pyrimidinen und deren salzen, n-oxiden und n-acylderivaten |
| US5597828A (en) * | 1988-12-07 | 1997-01-28 | Glaxo Wellcome Inc. | Certain 2,4-diamino-5-(2,3-dihalophenyl)-6-substituted pyrimidines which are pharmacologically active CNS compounds |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR6915082D0 (pt) | 1969-05-16 | 1973-03-08 | Wellcome Found | Processo de preparacao de benzil-pirimidinas |
| DE2051871A1 (en) * | 1969-05-16 | 1971-11-18 | The Wellcome Foundation Ltd., London | Beta-amino-alpha-aryloxymethylacrylonitrile - and 2,4-diamino-5-benzylpyrimidine derivs. useful as antibacterial agents |
| BE792096A (fr) * | 1971-12-01 | 1973-05-30 | Hoffmann La Roche | Nouvelles benzylpyrimidines |
| EP0046856A3 (de) * | 1980-08-29 | 1982-07-28 | Hüls Troisdorf Aktiengesellschaft | Verfahren zur Herstellung von 4-Amino-2-mercaptopyrimidinen |
| HU187370B (en) * | 1981-06-26 | 1985-12-28 | Egyt Gyogyszervegyeszeti Gyar | Improved process for producing 2,4-diamino-5-bracket-3-comma above, 4-comma above,5-comma above-trimethoxy-benzyl-bracket closed-pyrimidine |
| HU186413B (en) * | 1981-06-26 | 1985-07-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 2,4-diamino-5-bracket-3-comma above,4-comma above,5-comma above-trimethoxy-benzyl-bracket closed-pyrimidine |
| DE3603577A1 (de) * | 1986-02-06 | 1987-08-13 | Joachim K Prof Dr Seydel | Neue substituierte 2,4-diamino-5-benzylpyrimidine, deren herstellung und deren verwendung als arzneimittel mit antibakterieller wirksamkeit |
-
0
- DE DENDAT1303727D patent/DE1303727B/de not_active Withdrawn
-
1959
- 1959-09-03 GB GB30102/59A patent/GB957797A/en not_active Expired
-
1960
- 1960-08-06 IT IT13817/60A patent/IT1061608B/it active
- 1960-08-12 DE DE1445176A patent/DE1445176C3/de not_active Expired
- 1960-08-29 AT AT656060A patent/AT230379B/de active
- 1960-09-02 SE SE836660A patent/SE219368C1/sv unknown
- 1960-09-02 CH CH996260A patent/CH418338A/de unknown
- 1960-09-03 FI FI1465/60A patent/FI42960B/fi active
-
1966
- 1966-12-31 MY MY196661A patent/MY6600061A/xx unknown
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3461206A (en) * | 1964-11-12 | 1969-08-12 | Hoffmann La Roche | Compositions containing a sulfanilamide and a 2,4-diamino-5-(2',4',5'-trisubstitutedbenzyl)pyrimidine |
| DE2010166A1 (de) * | 1969-03-06 | 1970-09-17 | The Wellcome Foundation Ltd., London | Stabilisierte alpha-Benzylaerylnitrile, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US3697512A (en) * | 1969-03-06 | 1972-10-10 | Burroughs Wellcome Co | 5-benzyl pyrimidines intermediates |
| DE2065367A1 (de) * | 1969-03-06 | 1973-05-24 | Wellcome Found | Verfahren zur herstellung von 2,4diamino-5-benzylpyrimidinen |
| US3852276A (en) * | 1969-03-06 | 1974-12-03 | Burroughs Wellcome Co | 5-benzyl pyrimidines intermediate therefore, and method |
| US3855265A (en) * | 1969-03-06 | 1974-12-17 | Burroughs Wellcome Co | 5-benzyl pyrimidines intermediates therefore, and method |
| US3950378A (en) * | 1969-03-06 | 1976-04-13 | Burroughs Wellcome Co. | Preparation of β-anilino-α-benzylacrylonitriles |
| US3991050A (en) * | 1969-03-06 | 1976-11-09 | Burroughs Wellcome Co. | Preparation of β-Amino-α-benzylacrylonitriles |
| US3998814A (en) | 1969-03-06 | 1976-12-21 | Burroughs Wellcome Co. | Process for preparing β-amino-α-benzylacrylonitriles |
| US4052553A (en) * | 1969-03-06 | 1977-10-04 | Burroughs Wellcome Co. | 5-benzyl pyrimidines intermediates therefore, and method |
| US4116958A (en) * | 1971-10-12 | 1978-09-26 | Burroughs Wellcome Co. | Organic synthetic methods benzylpyrimidine derivatives |
| US4251454A (en) | 1974-12-24 | 1981-02-17 | Hoffmann-La Roche Inc. | Benzylpyrimidines |
| US4137411A (en) * | 1977-02-04 | 1979-01-30 | Hoffmann-La Roche Inc. | Preparation of 2,4-diamino-5-(4-amino-3,5-substituted-benzyl)-pyrimidines |
| US4180578A (en) | 1977-05-09 | 1979-12-25 | Ludwig Heumann, & Co. GmbH | 2,4-Diamino-5-(4'-methylthio)benzylpyrimidenes, compounds, compositions and method of use |
| EP0051879A3 (en) * | 1980-11-11 | 1982-08-04 | The Wellcome Foundation Limited | Substituted pyrimidines, their synthesis and compositions containing them, their use in medicine and intermediates for making them |
| US4438267A (en) | 1980-11-11 | 1984-03-20 | Daluge Susan M | Monoheteroring compounds and their use |
| AT384023B (de) * | 1980-11-11 | 1987-09-25 | Wellcome Found | Verfahren zur herstellung von neuen 2,4-diamino-5-(subst.)pyrimidinen und deren salzen, n-oxiden und n-acylderivaten |
| US4761475A (en) * | 1980-11-11 | 1988-08-02 | Daluge Susan M | 2,4-diaminopyrimidines substituted with heterobicyclomethyl radicals at the 5 position useful as antibacterials |
| EP0096214A1 (en) * | 1982-05-01 | 1983-12-21 | The Wellcome Foundation Limited | Antibacterial pyrimidine compounds |
| AU569468B2 (en) * | 1982-05-01 | 1988-02-04 | Wellcome Foundation Limited, The | 2,4 - diamino -s- (substituted) pyrimidines |
| US4587341A (en) * | 1982-05-07 | 1986-05-06 | Burroughs Wellcome Co. | 2,4-diamino-5-(1,2,3,4-tetrahydro-(substituted or unsubstituted)-6-quinolylmethyl)pyrimidines, useful as antimicrobials |
| US5597828A (en) * | 1988-12-07 | 1997-01-28 | Glaxo Wellcome Inc. | Certain 2,4-diamino-5-(2,3-dihalophenyl)-6-substituted pyrimidines which are pharmacologically active CNS compounds |
| US5712276A (en) * | 1988-12-07 | 1998-01-27 | Glaxo Wellcome Inc. | 2-(n-alkylpiperazino or morpholino)-4-amino-5-aryl-pyrimidines |
Also Published As
| Publication number | Publication date |
|---|---|
| SE219368C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-03-12 |
| CH418338A (de) | 1966-08-15 |
| DE1445176C3 (de) | 1974-04-25 |
| DE1303727B (de) | 1976-02-05 |
| DE1445176A1 (de) | 1968-10-17 |
| DE1445176B2 (de) | 1973-09-06 |
| MY6600061A (en) | 1966-12-31 |
| FI42960B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-09-02 |
| AT230379B (de) | 1963-12-10 |
| IT1061608B (it) | 1983-04-30 |
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