IE49591B1 - Pyrimidine derivatives - Google Patents
Pyrimidine derivativesInfo
- Publication number
- IE49591B1 IE49591B1 IE864/80A IE86480A IE49591B1 IE 49591 B1 IE49591 B1 IE 49591B1 IE 864/80 A IE864/80 A IE 864/80A IE 86480 A IE86480 A IE 86480A IE 49591 B1 IE49591 B1 IE 49591B1
- Authority
- IE
- Ireland
- Prior art keywords
- pyrimidine
- isopropylamino
- general formula
- aralkyloxy
- alkoxy
- Prior art date
Links
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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Compounds of the general formula A4=H or OH A5=H or OH A6=H or OH A4=A5=A6=H excluded are prepared by reducing compounds of the general formula A'4=H, alkoxy or aralkyloxy A'5=H, alkoxy or aralkyloxy A'6=H, alkoxy or aralkyloxy A'4=A'5=A'6=H excluded with hydrogen in the presence of a hydrogenation catalyst, e.g. palladium. The compounds I are of therapeutical interest.
Description
The invention hydroxy derivatives formula I relates to a method for the preparation of of 2-isopropylamino-pyrimidine of the general
wherein each of A^, Ag and Ag independently represents a hydrogen atom or a hydroxy group with the proviso that at least one of A^, Ag and Ag does not represent a hydrogen atom. These compounds are claimed per se in our copending Application No. 477/8 3 and are of therapeutical interest.
The invention provides a method for the preparation of hydroxy derivatives of 2-isopropylamino-pyrimidine of the general formula I as above defined, the method comprising reducing aralkyloxy or alkoxy derivatives of 2-isopropylamino-pyrimidine of the general formula II ll
wherein each of A'4, A'g and A‘g independently represents a hydrogen atom or an aralkyloxy or alkoxy group with the proviso that at least one of A'4> A'5 and A'g does not represent a hydrogen atom with hydrogen in the presence of a hydrogenation catalyst, such as palladium.
The invention is illustrated by the following Examples.
EXAMPLE 1:
2-isopropylamino-5-hydroxy pyrimidine In a pressurized reactor of 2 litre capacity, preferably cleared by a nitrogen flow, were placed 0.8 g of
2-isopropylamino-5-benzyloxy-pyrimid1ne, 40 ml of methanol and 80 mg of palladium catalyst; hydrogenation was performed for 2 hours at normal pressure. After filtration off of the catalyst and evaporation off of the methanol, the product was taken up in diethyl ether and the solution was filtered to eliminate insoluble matter. The diethyl ether was evaporated off and the product was recrystallised first from water and then from ethyl acetate. After drying, there was obtained 0.4 g (yield S0%) of 2-isopropylamino-5-hydroxy-pyrimidine. Elemental analysis showed the expected empirical formula CgH^NjO. Melting point 161°C (Tottoli), U.V. Spectroscopy confirmed the structure.
EXAMPLE 2
2-isopropyl ami no-4-hydroxy pyrimi di ne The method described in Example 1 was applied to
2-isopropyiamino-4-ethoxy-pyrinridine instead of
2-isopropyl-amino-5-benzyloxy-pyrimidine. The yield was 83% of a white crystalline product melting at 140°C (Tottoli), elemental analysis of which confirmed a good correspondence with the formula CyH^N^O. U.V. Spectroscopy confirmed the structure.
EXAMPLE 3
2-isopropylami no-4,6-dihydroxy pyridine
The method described in Example 1 was applied to 2-isopropylanrino-4,6-dibenzyloxy-pyrimidine instead of 2-isopropylamino-5-benzyloxy-pyrimidine. The yield was 78% of a white crystalline product (hydrochloride) melting at 218-221°C (Tottoli), with decomposition, elemental analysis of which confirmed a good correspondence with the formula
HCI. U.V. Spectroscopy confirmed the structure.
Claims (4)
1. A method for the preparation of a hydroxy derivative of 2-isopropylamino-pyrimidine of the general formula I as herein defined, the method comprising reducing an aralkyloxy or alkoxy 5 derivative of 2-isopropylamino-pyrimidine of the general formula II as herein defined with hydrogen in the presence of a hydrogenation catalyst.
2. A method according to claim 1 in which the hydrogenation catalyst is palladium. 10
3. A method for the preparation of a hydroxy derivative of 2-isopropylamino-pyrimidine of the general formula I as herein defined, the method being substantially as described herein with reference to any one of the Examples.
4. A hydrogen derivative of 15 2-isopropylamino-pyrimidine of general formula I whenever prepared by a method as claimed in any of claims 1 to 3.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7914987 | 1979-04-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE800864L IE800864L (en) | 1980-10-30 |
| IE49591B1 true IE49591B1 (en) | 1985-10-30 |
Family
ID=10504858
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE865/80A IE49709B1 (en) | 1979-04-30 | 1980-04-28 | Pyrimidine derivatives |
| IE864/80A IE49591B1 (en) | 1979-04-30 | 1980-04-28 | Pyrimidine derivatives |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE865/80A IE49709B1 (en) | 1979-04-30 | 1980-04-28 | Pyrimidine derivatives |
Country Status (26)
| Country | Link |
|---|---|
| JP (2) | JPS55145670A (en) |
| AR (2) | AR222870A1 (en) |
| AT (2) | AT380012B (en) |
| BE (2) | BE882593A (en) |
| CH (2) | CH645633A5 (en) |
| DK (2) | DK183780A (en) |
| EG (2) | EG14259A (en) |
| ES (2) | ES8103061A1 (en) |
| FI (2) | FI66358C (en) |
| FR (2) | FR2455588A1 (en) |
| GB (2) | GB2054556B (en) |
| HK (2) | HK55583A (en) |
| IE (2) | IE49709B1 (en) |
| IN (2) | IN154066B (en) |
| IT (2) | IT1141296B (en) |
| LU (2) | LU82333A1 (en) |
| MA (1) | MA18824A1 (en) |
| MX (2) | MX5878E (en) |
| MY (2) | MY8400204A (en) |
| NL (2) | NL8002271A (en) |
| NO (2) | NO154056C (en) |
| NZ (2) | NZ193421A (en) |
| OA (2) | OA06527A (en) |
| PT (2) | PT71154A (en) |
| SG (2) | SG22283G (en) |
| ZA (2) | ZA801960B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63145595U (en) * | 1987-03-13 | 1988-09-26 | ||
| JPS645795U (en) * | 1987-06-26 | 1989-01-13 | ||
| JPH01100695U (en) * | 1987-12-21 | 1989-07-06 | ||
| US5264435A (en) * | 1988-12-29 | 1993-11-23 | Mitsui Petrochemical Industries, Ltd. | Pyrimidines and their pharmaceutical acceptable salts, and their use as medicines |
| HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
-
1980
- 1980-04-02 BE BE0/200083A patent/BE882593A/en not_active IP Right Cessation
- 1980-04-02 ZA ZA00801960A patent/ZA801960B/en unknown
- 1980-04-02 BE BE0/200084A patent/BE882594A/en not_active IP Right Cessation
- 1980-04-02 ZA ZA00801958A patent/ZA801958B/en unknown
- 1980-04-03 LU LU82333A patent/LU82333A1/en unknown
- 1980-04-03 LU LU82332A patent/LU82332A1/en unknown
- 1980-04-03 FI FI801083A patent/FI66358C/en not_active IP Right Cessation
- 1980-04-03 FI FI801084A patent/FI66359C/en not_active IP Right Cessation
- 1980-04-07 IN IN253/DEL/80A patent/IN154066B/en unknown
- 1980-04-07 IN IN254/DEL/80A patent/IN154067B/en unknown
- 1980-04-08 CH CH268980A patent/CH645633A5/en not_active IP Right Cessation
- 1980-04-08 CH CH269080A patent/CH645361A5/en not_active IP Right Cessation
- 1980-04-11 NZ NZ193421A patent/NZ193421A/en unknown
- 1980-04-11 NZ NZ193422A patent/NZ193422A/en unknown
- 1980-04-15 GB GB8012349A patent/GB2054556B/en not_active Expired
- 1980-04-15 GB GB8012351A patent/GB2055801B/en not_active Expired
- 1980-04-18 NL NL8002271A patent/NL8002271A/en unknown
- 1980-04-18 NL NL8002272A patent/NL8002272A/en not_active Application Discontinuation
- 1980-04-22 IT IT21543/80A patent/IT1141296B/en active
- 1980-04-22 MA MA19019A patent/MA18824A1/en unknown
- 1980-04-22 IT IT21542/80A patent/IT1141487B/en active
- 1980-04-24 AT AT0221580A patent/AT380012B/en not_active IP Right Cessation
- 1980-04-24 AT AT0221680A patent/AT380013B/en not_active IP Right Cessation
- 1980-04-25 AR AR280811A patent/AR222870A1/en active
- 1980-04-25 AR AR280810A patent/AR222869A1/en active
- 1980-04-28 MX MX808786U patent/MX5878E/en unknown
- 1980-04-28 MX MX808783U patent/MX6514E/en unknown
- 1980-04-28 JP JP5557480A patent/JPS55145670A/en active Granted
- 1980-04-28 PT PT71154A patent/PT71154A/en unknown
- 1980-04-28 IE IE865/80A patent/IE49709B1/en unknown
- 1980-04-28 IE IE864/80A patent/IE49591B1/en unknown
- 1980-04-28 JP JP5557580A patent/JPS55145671A/en active Granted
- 1980-04-28 PT PT71155A patent/PT71155A/en unknown
- 1980-04-28 NO NO801235A patent/NO154056C/en unknown
- 1980-04-28 NO NO801234A patent/NO154055C/en unknown
- 1980-04-29 ES ES491000A patent/ES8103061A1/en not_active Expired
- 1980-04-29 ES ES490999A patent/ES490999A0/en active Granted
- 1980-04-29 EG EG258/80A patent/EG14259A/en active
- 1980-04-29 EG EG257/80A patent/EG14284A/en active
- 1980-04-29 DK DK183780A patent/DK183780A/en unknown
- 1980-04-29 DK DK183880A patent/DK183880A/en unknown
- 1980-04-30 FR FR8009732A patent/FR2455588A1/en active Granted
- 1980-04-30 OA OA57103A patent/OA06527A/en unknown
- 1980-04-30 FR FR8009733A patent/FR2455589A1/en active Granted
- 1980-04-30 OA OA57101A patent/OA06525A/en unknown
-
1983
- 1983-04-28 SG SG222/83A patent/SG22283G/en unknown
- 1983-04-28 SG SG225/83A patent/SG22583G/en unknown
- 1983-11-17 HK HK555/83A patent/HK55583A/en unknown
- 1983-11-17 HK HK556/83A patent/HK55683A/en unknown
-
1984
- 1984-12-30 MY MY204/84A patent/MY8400204A/en unknown
- 1984-12-30 MY MY203/84A patent/MY8400203A/en unknown
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