IE37452B1 - 2,4-diamino-5-benzylpyrimidines and processes for their production - Google Patents
2,4-diamino-5-benzylpyrimidines and processes for their productionInfo
- Publication number
- IE37452B1 IE37452B1 IE1329/71A IE132971A IE37452B1 IE 37452 B1 IE37452 B1 IE 37452B1 IE 1329/71 A IE1329/71 A IE 1329/71A IE 132971 A IE132971 A IE 132971A IE 37452 B1 IE37452 B1 IE 37452B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- formula
- alkylthio
- diamino
- compounds
- Prior art date
Links
- XHPZVBGIPQQTQW-UHFFFAOYSA-N 5-benzylpyrimidine-2,4-diamine Chemical class NC1=NC(N)=NC=C1CC1=CC=CC=C1 XHPZVBGIPQQTQW-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000001302 tertiary amino group Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- 229960004050 aminobenzoic acid Drugs 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000000078 anti-malarial effect Effects 0.000 abstract 1
- 239000003430 antimalarial agent Substances 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 229940054534 ophthalmic solution Drugs 0.000 abstract 1
- 239000002997 ophthalmic solution Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- 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
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1375162 2,4-Diamino-5-benzylpyrimidines WELLCOME FOUNDATION Ltd (Burroughs Wellcome Co) 20 Oct 1971 [22 Oct 1970 16 April 1971 12 Oct 1971] 50350/70 9638/71 and 47491/71 Heading C2C [Also in Division A5] Novel compounds of general Formula (I) and their salts in which R 1 and R 3 are each alkyl groups having 2 to 4 C atoms and R 2 is an alkyl or alkoxy group having from 1 to 12 C atoms are prepared by (1) reacting guanidine with a novel compound of general Formula (II) in which (a) X and Y are an additional bond and Z is an alkoxy group or an alkylthio group or an NR<SP>4</SP>R<SP>5</SP> group which is an aliphatic or aromatic amino group in which R<SP>4</SP> and R<SP>5</SP> are not both hydrogen or a tertiary amino group in which NR 4 R 5 form a heterocyclic ring system or (b) X is a hydrogen atom and Y and Z are alkoxy groups or together form an alkylene-dioxy group; the reaction may be carried out in a C 1-4 alkanol solvent at an elevated temperature or by using a salt of guanidine in an aprotic solvent (2) aminating a novel compound of general Formula (III) where both Q<SP>1</SP> and Q<SP>2</SP> are halogen or one is halogen and the other is amino; (3) reacting a novel compound of Formula IV in which L is a hydrogen atom or an alkylthio or aralkylthio group having up to 12 C atoms with an alkylating agent R 2# where # is a reactive atom or group and in the case where L is an alkylthio or aralkylthio group removing this group by hydrogenolysis. Compounds of Formula III in which #1 is an amino group may be prepared by reaction of the appropriate formylated hydrocinnamic ester with guanidine followed by halogenation of the 4-hydroxyl group. Compounds of Formula IV are prepared by reaction of a Mannich base of Formula V where X is a tertiary amino group with either (a) 2,4-diaminopyrimidine under basic conditions or (b) 2,4-diamino-6-alkylthio pyrimidine or 2,4- diamino-6-aralkylthio-pyrimidine. Compounds of general Formula I exhibit antimalarial and/or antibacterial activity and with a pharmaceutically acceptable carrier form a composition which may be administered orally, parenterally, rectally, topically or in the form of an ophthalmic solution. Such compositions may also comprise a p-amino benzoic acid (such as a sulphonamide) as a competitor.
[GB1375162A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB963871*[A GB1375162A (en) | 1970-10-22 | 1970-10-22 | |
| GB963871 | 1971-04-16 | ||
| GB4749171 | 1971-10-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37452L IE37452L (en) | 1972-04-22 |
| IE37452B1 true IE37452B1 (en) | 1977-08-03 |
Family
ID=27255400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1329/71A IE37452B1 (en) | 1970-10-22 | 1971-10-21 | 2,4-diamino-5-benzylpyrimidines and processes for their production |
Country Status (20)
| Country | Link |
|---|---|
| JP (2) | JPS5536662B1 (en) |
| AR (3) | AR192588A1 (en) |
| AT (1) | AT319948B (en) |
| BE (1) | BE774281A (en) |
| BG (4) | BG20364A3 (en) |
| CA (1) | CA967158A (en) |
| CH (3) | CH568301A5 (en) |
| DD (1) | DD100877A5 (en) |
| DK (1) | DK132174C (en) |
| ES (1) | ES396219A1 (en) |
| FI (1) | FI56175C (en) |
| FR (1) | FR2111769B1 (en) |
| GB (1) | GB1375162A (en) |
| IE (1) | IE37452B1 (en) |
| IL (2) | IL37984A (en) |
| LU (1) | LU64129A1 (en) |
| MC (1) | MC894A1 (en) |
| NL (1) | NL175178C (en) |
| SE (2) | SE384505B (en) |
| ZM (1) | ZM14971A1 (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792096A (en) * | 1971-12-01 | 1973-05-30 | Hoffmann La Roche | NEW BENZYLPYRIMIDINES |
| FR2397407A2 (en) * | 1977-07-11 | 1979-02-09 | Dick Pierre | 2,4-DIAMINO PYRIMIDINE DERIVATIVES AND THEIR SOLUTION IN ASSOCIATION WITH SULFAMIDS |
| PT69656A (en) * | 1978-05-24 | 1979-06-01 | Wellcome Found | Benzylpyrimidine compositions |
| JPS61156909A (en) * | 1984-12-27 | 1986-07-16 | Matsushita Electric Ind Co Ltd | Current mirror circuit |
| JPS62145907A (en) * | 1985-12-20 | 1987-06-30 | Hitachi Ltd | Transistor circuit |
| TWI414525B (en) | 2004-03-26 | 2013-11-11 | Dainippon Sumitomo Pharma Co | 9-substituted-8-oxoadenine compound |
| EP2041135A4 (en) | 2006-07-05 | 2010-12-01 | Astrazeneca Ab | 8-oxoadenine derivatives acting as modulators of tlr7 |
| TW200831105A (en) | 2006-12-14 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| SI2132209T1 (en) | 2007-03-19 | 2014-05-30 | Astrazeneca Ab | 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7 ) modulators |
| WO2008114006A1 (en) | 2007-03-19 | 2008-09-25 | Astrazeneca Ab | 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7) modulators |
| JPWO2008114819A1 (en) | 2007-03-20 | 2010-07-08 | 大日本住友製薬株式会社 | New adenine compounds |
| PE20091236A1 (en) * | 2007-11-22 | 2009-09-16 | Astrazeneca Ab | PYRIMIDINE DERIVATIVES AS IMMUNOMODULATORS OF TLR7 |
| UY31531A1 (en) | 2007-12-17 | 2009-08-03 | SALTS DERIVED FROM 8-OXOADENINE PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND THEIR USE IN THERAPY AS TOLL TYPE RECEIVER MODULATORS (TLR) | |
| GB0908772D0 (en) | 2009-05-21 | 2009-07-01 | Astrazeneca Ab | New salts 756 |
| MX2011012337A (en) | 2009-05-21 | 2011-12-08 | Dainippon Sumitomo Pharma Co | Novel pyrimidine derivatives and their use in the treatment of cancer and further diseases. |
| ES2575688T3 (en) | 2010-12-16 | 2016-06-30 | Sumitomo Dainippon Pharma Co., Ltd. | Imidazo [4,5-c] quinolin-1-yl derivative useful in therapy |
| EP2651943B1 (en) | 2010-12-17 | 2017-03-22 | Sumitomo Dainippon Pharma Co., Ltd. | Purine derivatives |
| EP2850067B1 (en) | 2012-05-18 | 2017-08-16 | Sumitomo Dainippon Pharma Co., Ltd. | Carboxylic acid compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE710100A (en) * | 1967-02-02 | 1968-07-30 | ||
| JPS511716A (en) * | 1974-06-25 | 1976-01-08 | Toray Industries | HORIESUTERUMARUCHIFUIRAMENTONO SEIHO |
-
1970
- 1970-10-22 GB GB963871*[A patent/GB1375162A/en not_active Expired
-
1971
- 1971-10-21 ZM ZM149/71A patent/ZM14971A1/en unknown
- 1971-10-21 BG BG021451A patent/BG20364A3/en unknown
- 1971-10-21 FI FI2975/71A patent/FI56175C/en active
- 1971-10-21 AT AT909371A patent/AT319948B/en not_active IP Right Cessation
- 1971-10-21 MC MC951A patent/MC894A1/en unknown
- 1971-10-21 NL NLAANVRAGE7114494,A patent/NL175178C/en not_active IP Right Cessation
- 1971-10-21 SE SE7113328A patent/SE384505B/en unknown
- 1971-10-21 AR AR238596A patent/AR192588A1/en active
- 1971-10-21 BE BE774281A patent/BE774281A/en not_active IP Right Cessation
- 1971-10-21 DD DD167435A patent/DD100877A5/xx unknown
- 1971-10-21 CH CH1532171A patent/CH568301A5/xx not_active IP Right Cessation
- 1971-10-21 IE IE1329/71A patent/IE37452B1/en unknown
- 1971-10-21 CH CH1027775A patent/CH582681A5/xx not_active IP Right Cessation
- 1971-10-21 BG BG018828A patent/BG20797A3/en unknown
- 1971-10-21 IL IL37984A patent/IL37984A/en unknown
- 1971-10-21 DK DK513771A patent/DK132174C/en not_active IP Right Cessation
- 1971-10-21 BG BG021452A patent/BG20365A3/en not_active Expired
- 1971-10-21 ES ES396219A patent/ES396219A1/en not_active Expired
- 1971-10-21 IL IL45422A patent/IL45422A/en unknown
- 1971-10-21 JP JP8365271A patent/JPS5536662B1/ja active Pending
- 1971-10-21 CH CH1027675A patent/CH568302A5/xx not_active IP Right Cessation
- 1971-10-21 FR FR7137870A patent/FR2111769B1/fr not_active Expired
- 1971-10-21 CA CA125,807A patent/CA967158A/en not_active Expired
- 1971-10-21 LU LU64129A patent/LU64129A1/xx unknown
-
1972
- 1972-06-27 AR AR242772A patent/AR192802A1/en active
- 1972-06-27 AR AR242773A patent/AR192803A1/en active
- 1972-10-21 BG BG021466A patent/BG21406A3/en unknown
-
1974
- 1974-05-20 SE SE7406661A patent/SE409705B/en not_active IP Right Cessation
-
1977
- 1977-12-22 JP JP15499477A patent/JPS53135991A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH568302A5 (en) | 1975-10-31 |
| BG20365A3 (en) | 1975-11-05 |
| AR192588A1 (en) | 1973-02-28 |
| IE37452L (en) | 1972-04-22 |
| AR192803A1 (en) | 1973-03-14 |
| NL175178B (en) | 1984-05-01 |
| FR2111769A1 (en) | 1972-06-09 |
| GB1375162A (en) | 1974-11-27 |
| FI56175B (en) | 1979-08-31 |
| CA967158A (en) | 1975-05-06 |
| IL45422A (en) | 1976-03-31 |
| CH582681A5 (en) | 1976-12-15 |
| DK132174C (en) | 1976-03-29 |
| SE384505B (en) | 1976-05-10 |
| BG20797A3 (en) | 1975-12-20 |
| ES396219A1 (en) | 1975-09-16 |
| BG21406A3 (en) | 1976-05-20 |
| FI56175C (en) | 1979-12-10 |
| AR192802A1 (en) | 1973-03-14 |
| IL37984A (en) | 1976-03-31 |
| DK132174B (en) | 1975-11-03 |
| SE409705B (en) | 1979-09-03 |
| NL7114494A (en) | 1972-04-25 |
| MC894A1 (en) | 1972-06-22 |
| BG20364A3 (en) | 1975-11-05 |
| NL175178C (en) | 1984-10-01 |
| DD100877A5 (en) | 1973-10-12 |
| ZM14971A1 (en) | 1972-07-21 |
| JPS5536662B1 (en) | 1980-09-22 |
| IL37984A0 (en) | 1971-12-29 |
| CH568301A5 (en) | 1975-10-31 |
| LU64129A1 (en) | 1972-06-28 |
| AT319948B (en) | 1975-01-10 |
| BE774281A (en) | 1972-04-21 |
| JPS53135991A (en) | 1978-11-28 |
| FR2111769B1 (en) | 1974-10-18 |
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