GB1062572A - Morphanthridine derivatives,uses therefor and processes of preparing the same - Google Patents
Morphanthridine derivatives,uses therefor and processes of preparing the sameInfo
- Publication number
- GB1062572A GB1062572A GB4255463A GB4255463A GB1062572A GB 1062572 A GB1062572 A GB 1062572A GB 4255463 A GB4255463 A GB 4255463A GB 4255463 A GB4255463 A GB 4255463A GB 1062572 A GB1062572 A GB 1062572A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- compounds
- alkyl
- group
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises: (I) compounds of Formulae 1 and 2 -<FORM:1062572/C2/1> <FORM:1062572/C2/2> and non-toxic, physiologically acceptable acid addition salts and quaternary ammonium salts thereof, where A and A1 are hydrogen, halogen, alkoxy, alkyl, alkylthio, or trifluoromethyl; B is hydroxy, or -OCOR6 where R6 is lower alkyl, R and R1 are hydrogen, alkyl, alkenyl, alkynyl, phenylalkyl, p-chlorobenzyl, diphenylmethyl, trityl, naphthylmethyl, or phenylalkenyl, and CN is a 3- or 4-piperidyl, 3-pyrrolidyl or 3- or 4-homopiperidyl group, and the preparation thereof (1) by reacting a compound of formula <FORM:1062572/C2/3> with a compound of formula <FORM:1062572/C2/4> to produce a compound of formula 2 in which B is a hydroxy group, and dehydrating this compound to give a compound of Formula 1, in which M is an alkali metal, and R and R1 represent alkyl, alkenyl, alkynyl, phenylalkyl, p-chlorobenzyl, diphenylmethyl, trityl, naphthylmethyl or phenylalkenyl; (2) by reacting a compound of Formula 5 <FORM:1062572/C2/5> with a compound of formula <FORM:1062572/C2/6> to produce a compound of Formula 6 <FORM:1062572/C2/7> and dehydrating this compound to produce a compound of Formula 1, where R and R1 are as defined under (1) above, and Z is lithium or X-Mgwhere X is chlorine, bromine or iodine; (II) compounds of Formula 6 and non-toxic, physiological acceptable acid addition salts and lower alkyl quaternary ammonium salts thereof, (III) compounds of Formula 3 <FORM:1062572/C2/8> and non-toxic physiologically acceptable acid addition salts and lower alkyl quaternary ammonium salts thereof, where R2 is hydrogen, alkyl, alkenyl, alkynyl, phenylalkyl, p-chlorobenzyl, or phenylalkenyl, and Am is either pyridinyl, piperidinyl, pyrrolidinyl, homopiperidinyl or quinuclidinyl, of which the piperidine, pyrrolidine and homopiperidine rings may be R-substituted on the nitrogen atom, or an -NR3R4 group where R3 and R4 are hydrogen alkyl, alkenyl, phenyl, phenylalkyl, diphenylmethyl, trityl, naphthylmethyl, cycloalkyl, or cycloalkyl-alkyl, or a group in which-NR3R4 represents a morpholino, pyrrolidino, piperidino, homopiperidino, piperazino, 1,2,3,4-tetrahydroquinolino, 1,2,3,4-tetrahydroisoquinolino, N-alkylpiperazino, N-(aryl-alkyl)-piperazino or N-(hydroxyalkyl)-piperazino, and Y is a chemical bond, or, when Am is a -NR3R4 group, an alkylene radical, and the preparation thereof (1) by reacting a compound of Formula 4 above with a compound of formula O=C(R2)-Y-Am, to produce a compound of Formula 7 <FORM:1062572/C2/9> and dehydrating this compound to produce a compound of Formula 3 wherein R2, Y and Am are as defined above except that the cyclic amino groups represented by Am have N-substituents and R3 and R4 are not hydrogen, and R is defined under (I)(1) above; (2) by reacting a compound of Formula 5 above with a compound of formula Z-CH(R2)-Y-Am to produce a compound of Formula 8 <FORM:1062572/C2/100> and dehydrating this compound to produce a compound of Formula 3, wherein Z is as defined under (I)(2) above, and R, R2, Y and Am are as defined in (III)(1) above; (IV) compounds of Formula 8, and the non-toxic physilogically acceptable acid addition salts and lower alkyl quaternary ammonium salts thereof; (V) compounds of Formula 7, and the lower alkyl esters thereof, and the non-toxic physiologically acceptable acid addition salts and lower alkyl quaternary ammonium salts thereof; and (VI) compounds of Formula 9 <FORM:1062572/C2/111> and non-toxic, acid-addition salts and lower alkyl quaternary ammonium salts thereof, wherein R is as defined under (I) above except that it is not a benzyl group, and R3 is an alkyl, alkenyl, cycloalkyl, cycloalkyl-alkyl, phenyl, phenylalkyl (except benzyl), diphenylmethyl, trityl or naphthylmethyl group, and R5 is an alkoxy, alkylthio, phenoxy or phenylthio group. These compounds of Formula 9 may be prepared by reacting the compounds of Formula 3 wherein Am is -NR3R4 and R4 is benzyl with a chloroformic or chlorothioformic acid ester. They may then be hydrolysed to produce the corresponding compounds in which R4 is hydrogen. The compounds of the invention containing free hydroxy groups can be converted to esters by conventional methods. The free hydroxy containing compounds or esters thereof having a cleavable or removable substituent on one or both of the nitrogens, e.g. a trityl group, can be subjected to conditions such as reductive or hydrolytic cleavage to remove such groups. Therapeutic compositions, which have anti-cholinergic, analgetic, antispasmodic, anti-depressant and tranquillizing activity, and which may be administered orally or parenterally, contain as active ingredients compounds of Formulae 1, 2, 6, 3, 8, 7 and 9 above. The compounds may also be used to purify penicillin, with which they form salts.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB4255463A GB1062572A (en) | 1963-10-29 | 1963-10-29 | Morphanthridine derivatives,uses therefor and processes of preparing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB4255463A GB1062572A (en) | 1963-10-29 | 1963-10-29 | Morphanthridine derivatives,uses therefor and processes of preparing the same |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1062572A true GB1062572A (en) | 1967-03-22 |
Family
ID=10424935
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4255463A Expired GB1062572A (en) | 1963-10-29 | 1963-10-29 | Morphanthridine derivatives,uses therefor and processes of preparing the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1062572A (en) |
-
1963
- 1963-10-29 GB GB4255463A patent/GB1062572A/en not_active Expired
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