GB810304A - Improvements in or relating to amines - Google Patents
Improvements in or relating to aminesInfo
- Publication number
- GB810304A GB810304A GB2517855A GB2517855A GB810304A GB 810304 A GB810304 A GB 810304A GB 2517855 A GB2517855 A GB 2517855A GB 2517855 A GB2517855 A GB 2517855A GB 810304 A GB810304 A GB 810304A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- compounds
- formula
- oxo
- amino
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0810304/IV (b)/1> wherein R1 and R2 are the same or different and are each a hydrogen atom or a lower alkyl, hydroxyalkyl (including polyhydroxyalkyl) or alkoxyalkyl group, R3 is hydrogen, methyl or a substituted or unsubstituted alkoxy group of not more than 4 carbon atoms, A1 is a saturated or ethylenically unsaturated hydrocarbon chain of 5-9 carbon atoms which is either unbranched or is substituted by one or more lower alkyl groups and R1 is a cyclic acylamido group of the formula <FORM:0810304/IV (b)/2> wherein X is the divalent radical necessary to complete a saturated or unsaturated heterocyclic ring which optionally contains further hetero atoms or substituents, including fused rings, but excluding a second carbonyl group adjacent to the nitrogen atom, and acid addition salts of these compounds and formaldehyde bisulphite derivatives of the compounds which are primarily amines. The compounds are made by treating a compound of the formula <FORM:0810304/IV (b)/3> with a compound MR11, wherein Y is a tertiary amino group or a group convertible to a primary, secondary or tertiary amino group, A11 is the same as A1 or is a corresponding less-saturated hydrocarbon chain, Z is the residue of a reactive ester, such as a halogen atom, M is hydrogen or an alkali metal atom and R11 represents R1 or a group which can be converted thereto, and, if necessary treating the product to convert any of Y, A11 and R11 into R1R2N-, A1 or R1, respectively; alternatively a compound of the formula <FORM:0810304/IV (b)/4> is reacted with a compound of the formula Z-A11-R11 and the product is treated to convert Y, A11 and R11 into R1R2N-, A1 or R1, respectively. Suitably the group Y may be (a) an acylamido, carbonamido, nitro, nitroso, alkoxycarboxylamido, anil or arylazo group, convertible into a primary amino group; (b) an anil, alkoxycarbonylamido, acylamido or acylalkylamido group, convertible into a secondary amino group, or (c) a quaternary ammonium or acylalkylamido group, convertible into a tertiary amino group. Also compounds of the general formula I containing a primary or secondary amino group are converted into products containing more highly substituted amino groups, for example by treatment with an alkylating agent or an alkylene oxide. The compounds are used pharmaceutically in the treatment of bilharziasis. In examples: (1) 5-p-nitrophenoxypentyl iodide (prepared by treating the bromide with sodium iodide) is reacted with the sodium salt of 2-pyridone, the resulting N-(5-p-nitrophenoxypentyl) pyrid-2-one is reduced with sodium sulphide to the p-amino derivative and subsequently with hydrogen in the presence of platinum to give N-(5-p-amino-phenoxypentyl)-piperid-2-one; (2) 1-p-amino-phenoxy-5-phthalimido-pentane is reduced with tin and hydrochloric acid to N-(5-p-amino-phenoxypentyl) phthalimidine, the o-methoxy derivative is similarly prepared, and (3) 1-p-acetamidophenoxy - 5 - bromopentane (prepared from p-acetamidophenol and 1:5-dibromopentane) is heated with the sodium salt of 3-oxo-2:3-dihydro-benzisothiazole and the resulting 1 - p - acetamidophenoxy - 5 - (3 - oxo-2:3 - dihydrobenzisothiazol - 2 - yl)-pentane is hydrolysed to 1-p-aminophenoxy-5-(3-oxo-2:3-dihydrobenzisothiazol-2-yl)-pentane which is purified via its methanesulphonate. Specifications 808,952, and 809,023 are referred to.ALSO:Therapeutic compositions for the treatment of bilharziasis comprise compounds of the formula <FORM:0810304/VI/1> wherein R1 and R2 represent a hydrogen atom or a lower alkyl, hydroxyalkyl (including polyhydroxyalkyl) or alkoxyalkyl group, A1 represents a saturated or ethylenically unsaturated hydrogen chain of 5-9 carbon atoms optionally substituted by one or more lower alkyl groups, R1 represents a cyclic acylamido group of the formula <FORM:0810304/VI/2> wherein X is the divalent radical necessary to complete an N-heterocyclic oxo-substituted ring which may contain further hetero atoms or bear substitutents, including fused rings, but excluding a second carbonyl group adjacent to the nitrogen and R3 is hydrogen, methyl or a substituted or unsubstituted alkoxy group, and acid addition salts of these compounds and formaldehyde-bisulphite derivatives of those compounds which are primary amines, in association with a pharmaceutical carrier. Suitably the group R1 may be a 2-oxopiperidinophthalimido or 3 - oxo - 2 : 3 - dihydrobenzisothiazolyl-(2) group, specified compounds being N - (5 - p - aminophenoxypentyl) - piperid - 2 - one, N - (5 - p - aminophenoxypentyl) - phthalimidine and its o-methoxy derivative and 1-p-aminophenoxy - 5 - (3 - oxo - 2 : 3 - dihydrobenzisothiazol - 2 - yl) - pentane. The active compounds may be admixed with liquid or solid diluents to provide elixirs, tablets, powders or capsules for oral administration or may be dissolved in a liquid diluent such as water for parenteral injection. Specified solid diluents include starch, lactose, talc, stearic acid and magnesium stearate. Specifications 808,952 and 809,023 are referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2517855A GB810304A (en) | 1955-09-01 | 1955-09-01 | Improvements in or relating to amines |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2517855A GB810304A (en) | 1955-09-01 | 1955-09-01 | Improvements in or relating to amines |
Publications (1)
Publication Number | Publication Date |
---|---|
GB810304A true GB810304A (en) | 1959-03-11 |
Family
ID=10223502
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2517855A Expired GB810304A (en) | 1955-09-01 | 1955-09-01 | Improvements in or relating to amines |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB810304A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3431270A (en) * | 1964-05-06 | 1969-03-04 | Upjohn Co | Certain aminoxyethyl derivatives of 2(1h)-pyridones |
US3995042A (en) * | 1973-09-07 | 1976-11-30 | E. R. Squibb & Sons, Inc. | Pyridine containing compounds |
-
1955
- 1955-09-01 GB GB2517855A patent/GB810304A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3431270A (en) * | 1964-05-06 | 1969-03-04 | Upjohn Co | Certain aminoxyethyl derivatives of 2(1h)-pyridones |
US3995042A (en) * | 1973-09-07 | 1976-11-30 | E. R. Squibb & Sons, Inc. | Pyridine containing compounds |
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