GB1399109A - Basically substituted alkyltheophyline derivatives - Google Patents
Basically substituted alkyltheophyline derivativesInfo
- Publication number
- GB1399109A GB1399109A GB4136472A GB4136472A GB1399109A GB 1399109 A GB1399109 A GB 1399109A GB 4136472 A GB4136472 A GB 4136472A GB 4136472 A GB4136472 A GB 4136472A GB 1399109 A GB1399109 A GB 1399109A
- Authority
- GB
- United Kingdom
- Prior art keywords
- theophylline
- group
- atom
- formula
- denotes
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1399109 Basically substituted alkylthiophyllines DEUTSCHE GOLDUND SILBERSCHEIDEANSTALT 6 Sept 1972 [6 Sept 1971 28 Oct 1971] 41364/72 Heading C2C Novel compounds of the Formula (I) in which R<SP>1</SP> denotes H or CH 3 , R<SP>2</SP> and R<SP>3</SP>, which may be the same or different, each represent H, CH 3 , OH or -CH 2 OH, R<SP>4</SP> is H or CH 3 , R<SP>5</SP> is C 1-6 alkyl, C 7-12 phenylalkyl or -NR<SP>6</SP>R<SP>7</SP>, in which R<SP>6</SP> and R<SP>7</SP>, which may be the same or different, each represents H or C 1-6 alkyl, or taken together with the N atom to which they are attached represent a 5, 6 or 7- membered ring which may optionally contain an oxygen atom, a further nitrogen atom or a sulphur atom and which may optionally be substituted by one or two C 1-4 alkyl groups, and Alk represents a linear propylene group, or R<SP>5</SP> is H, R<SP>1</SP> is H, R<SP>2</SP> is OH in the 4-position, R<SP>3</SP> is CH 3 or -CH 2 OH in the 3-position, R<SP>4</SP> is H or CH 3 in the 5-position and Alk denotes a propylene group which may optionally be substituted by one or more C 1-3 alkyl groups, with the proviso that if R<SP>5</SP> is a phenalkyl group, no more than two of R<SP>2</SP>, R<SP>3</SP> and R<SP>4</SP> can be H atoms; and the acid addition salts of these compounds, may be obtained by (a) reacting a compound corresponding to the general Formula (II) with a compound corresponding to Formula (III) in which Y denotes a ketone oxygen atom or a hydroxy group and one of X and Z represents a halogen atom and the other represents an amino group or where Z is an amino group, X and Y form an ethylene oxide ring together with a hydrogen atom on the carbon to which Y is attached and, if the compound produced has a keto group on the carbon atom adjacent to the benzene ring, this keto group is reduced into a hydroxy group; or (b) by condensing a compound of Formula (IV) with a compound of Formula (V) in which V and W are different from one another, and V represents -CHO or -CH 2 NH 2 (in which ease the linear carbon chain of -CH 2 CH 2 V can also be substituted by C 1-3 alkyl groups, whilst W denotes -C(R<SP>1</SP>) = O or -CH(R<SP>1</SP>)NH 2 , and Y denotes ketone oxygen or OH plus H, accompanied or followed by hydrogenation. In some cases, the phenolic hydroxy groups and amino groups are protected during reactions (a) and (b) and subsequently the protecting groups are removed. The compounds (I) can be converted into salts by known methods and those which contain asymmetric carbon atoms can be split up into optically active isomers by methods known per se, for example by means of an optically active acid. Alternatively optically active or diastereomeric starting materials can be used to yield the corresponding pure optically active form or diastereomeric configuration as end product. Starting materials are prepared as follows: 8 - diethylaminotheophylline is reacted with 1 - chloro - 3 - bromopropane forming 7- chloropropyl - 8 - diethylamino - theophylline which is then reacted with benzylamine to form 7 - (3 - benzylaminopropyl) - 8 - diethylaminotheophylline; 8 - morpholino - theophylline is similarly converted to 7-(3-benzylaminopropyl)- 8 - morpholino - theophylline and hydrogenated to remove the benzyl group ; similar compounds are obtained in which R 5 is benzyl, butyl, piperidino, 3-methylmorpholino; 7-(3-benzylaminobutyl) - theophylline is reacted with 4- chloroacetyl - 2 - methylphenol to form 7 - {3 - [2 - (3 - methyl - 4 - hydroxyphenyl)- 2 - oxoethyl - benzylamino] - butyl} - theophylline, HCl; 7-(3-benzylaminopropyl)-theophylline and 3 - acetoxymethyl - 4 - acetoxy- # - bromoacetophenone yield 7 - {3 - [2 - (3- hydroxymethyl - 4 - hydroxyphenyl) - 2 - oxoethyl benzylamino] - propyl} - theophylline, HCl; 3,5 - dimethyl - 4 - hydroxy - phenacyl chloride and 7 - (3 - benzylamino butyl)- theophylline yield 7 - {3 - [3,5 - dimethyl - 4- hydroxyphenyl) - 2 - oxoethylbenzylamino]- butyl}-theophylline, HCl. Pharmaceutical compositions having bronchial activity and therapeutically valuable circulatory effects comprise a compound of Formula I together with at least one pharmaceutical additive, excipient or diluent in forms suitable for administration enterally, parenterally, orally or perlingually.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT774571A AT311995B (en) | 1971-09-06 | 1971-09-06 | Process for the production of new basic substituted alkyl theophyllines |
AT931271A AT313916B (en) | 1971-10-28 | 1971-10-28 | Process for the preparation of new basic substituted theophyllines and their acid addition salts |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1399109A true GB1399109A (en) | 1975-06-25 |
Family
ID=25604090
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4136472A Expired GB1399109A (en) | 1971-09-06 | 1972-09-06 | Basically substituted alkyltheophyline derivatives |
Country Status (7)
Country | Link |
---|---|
BE (1) | BE788427A (en) |
CA (1) | CA988086A (en) |
CH (1) | CH580629A5 (en) |
DD (1) | DD102385A5 (en) |
ES (1) | ES406417A1 (en) |
FR (1) | FR2154457B1 (en) |
GB (1) | GB1399109A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0011399A1 (en) * | 1978-11-11 | 1980-05-28 | FISONS plc | N-substituted theophyllines, processes for their preparation and pharmaceutical compositions containing them |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT308139B (en) * | 1970-07-27 | 1973-06-25 | Degussa | Process for the preparation of new basic substituted alkyl theophyllines, their isomers and acid addition salts |
-
0
- BE BE788427D patent/BE788427A/en unknown
-
1972
- 1972-09-04 FR FR7231262A patent/FR2154457B1/fr not_active Expired
- 1972-09-04 DD DD165427A patent/DD102385A5/xx unknown
- 1972-09-05 ES ES406417A patent/ES406417A1/en not_active Expired
- 1972-09-06 CH CH1310672A patent/CH580629A5/xx not_active IP Right Cessation
- 1972-09-06 CA CA151,076A patent/CA988086A/en not_active Expired
- 1972-09-06 GB GB4136472A patent/GB1399109A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR2154457B1 (en) | 1975-06-20 |
CH580629A5 (en) | 1976-10-15 |
CA988086A (en) | 1976-04-27 |
BE788427A (en) | 1973-03-05 |
FR2154457A1 (en) | 1973-05-11 |
ES406417A1 (en) | 1975-07-01 |
DD102385A5 (en) | 1973-12-12 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |