GB1442102A – 7h-indolizino-5,6,7-ij-isoquinoline derivatives
– Google Patents
GB1442102A – 7h-indolizino-5,6,7-ij-isoquinoline derivatives
– Google Patents
7h-indolizino-5,6,7-ij-isoquinoline derivatives
Info
Publication number
GB1442102A
GB1442102A
GB3290174A
GB3290174A
GB1442102A
GB 1442102 A
GB1442102 A
GB 1442102A
GB 3290174 A
GB3290174 A
GB 3290174A
GB 3290174 A
GB3290174 A
GB 3290174A
GB 1442102 A
GB1442102 A
GB 1442102A
Authority
GB
United Kingdom
Prior art keywords
radical
carbon atoms
formula
substituted
moiety contains
Prior art date
1973-07-27
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
Application number
GB3290174A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Priority date (The priority date 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 date listed.)
1973-07-27
Filing date
1974-07-25
Publication date
1976-07-07
1973-07-27
Priority claimed from FR7327649A
external-priority
patent/FR2244515A1/en
1973-11-22
Priority claimed from FR7341616A
external-priority
patent/FR2252087A2/en
1974-05-30
Priority claimed from FR7418808A
external-priority
patent/FR2272668A2/en
1974-07-25
Application filed by Rhone Poulenc SA
filed
Critical
Rhone Poulenc SA
1976-07-07
Publication of GB1442102A
publication
Critical
patent/GB1442102A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 – C07D463/00
C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 – C07D463/00 in which the condensed system contains three hetero rings
C07D471/16—Peri-condensed systems
Abstract
1442102 7H – Indolizino[5,6,7-ij]isoquinoline derivatives RHONE-POULENC SA 25 July 1974 [27 July 1973 22 Nov 1973 30 May 1974] 32901/74 Heading C2C The invention comprises 7H – indolizino- [5,6,7-ij]isoquinoline derivatives of Formula (I) wherein R represents a hydrogen or halogen atom, or an alkoxy radical containing 1 to 4 carbon atoms, and R 1 represents a hydrogen atom, an alkyl radical containing 1 to 4 carbon atoms substituted by (i) a carboxy radical, (ii) an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 7 carbon atoms, or (iii) a carbamoyl radical, or R 1 represents a phenylalkyl radical in which the alkyl moiety contains 1 to 4 carbon atoms and is substituted by (i) a carboxy radical, (ii) an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 4 carbon atoms, or (iii) a carbamoyl radical, or R 1 represents an alkanoyl radical containing 1 to 4 carbon atoms or a benzoyl radical, and salts of those compounds wherein R 1 contains a carboxy radical. Compounds of Formula (I) in which R 1 represents a hydrogen atom, an alkyl radical containing 1 to 4 carbon atoms substituted by (i) a carboxy radical, (ii) an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 7 carbon atoms, or (iii) a carbamoyl radical, or R 1 represents a phenylalkyl radical in which the alkyl moiety contains 1 to 4 carbon atoms and is substituted by (i) a carboxy radical, (ii) an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 4 carbon atoms, or (iii) a carbamoyl radical, may be prepared by reacting a compound of the general formula or an acid addition salt thereof, with a 7H- indolizino[5,6,7 – ij]isoquinolin – 7 – one of the general formula Compounds of Formula (I) in which R 1 represents an alkanoyl radical containing 1 to 4 carbon atoms or a benxoyl radical may be prepared by reacting an acid of formula R 2 -COOH (where R 2 is H, an alkyl radical containing 1 to 3 carbon atoms or phenyl) or a reactive derivative thereof with a compound of formula Compounds of Formula (I) in which R 1 represents an alkyl radical containing 1 to 4 carbon atoms substituted by (i) a carboxy radical, (ii) an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 7 carbon atoms, or (iii) a carbamoyl radical, or R 1 represents a phenylalkyl radical in which the alkyl moiety contains 1 to 4 carbon atoms and is substituted by (i) a carboxy radical, (ii) an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 4 carbon atoms, or (iii) a carbamoyl radical, may be prepared by reacting a compound of the general formula (wherein R 3 represents an alkyl radical containing 1 to 4 carbon atoms substituted by (i) a carboxy radical, (ii) an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 7 carbon atoms, or (iii) a carbamoyl radical, or R 3 represents a phenylalkyl radical in which the alkyl moiety contains 1 to 4 carbon atoms and is substituted by (i) a carboxy radical, (ii) an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 4 carbon atoms, or (iii) a carbamoyl radical, and X represents a halogen atom with a quaternary ammonium salt of an oxime of the general Formula V). Compounds of Formula (I) in which R 1 represents an alkyl radical containing 1 to 4 carbon atoms substituted by an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 7 carbon atoms, or R 1 represents a phenylalkyl radical in which the alkyl moiety contains 1 to 4 carbon atoms and is substituted by an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 4 carbon atoms, may be prepared by converting by a method known per se the carboxy radical of a compound of formula (wherein R 4 represents an alkyl radical containing 1 to 4 carbon atoms substituted by a carboxy radical, or a phenylalkyl radical in which the alkyl moiety contains 1 to 4 carbon atoms and is substituted by a carboxy radical) to an alkoxycarbonyl radical containing 1 to 7 carbon atoms in the alkoxy moiety when R 4 is an alkyl radical substituted by a carboxy radical, or to an alkoxycarbonyl radical containing 1 to 4 carbon atoms in the alkoxy moiety when R 4 is a phenylalkyl radical in which the alkyl moiety is substituted by a carboxy radical. Compounds of Formula (I) in which R 1 represents an alkyl radical containing 1 to 4 carbon atoms substituted by a carbamoyl radical, or R 1 represents a phenylalkyl radical in which the alkyl moiety contains 1 to 4 carbon atoms and is substituted by a carbamoyl radical, may be prepared by converting by a method known per se the carboxy radical of the compound of Formula VII to a carbamoyl radical. Compounds of Formula (I) in which R 1 represents an alkyl radical containing 1 to 4 carbon atoms substituted by a carboxy radical, or a phenylalkyl radical in which the alkyl moiety contains 1 to 4 carbon atoms and is substituted by a carboxy radical, may be prepared by the saponification of a compound of the general formula wherein R 6 represents an alkyl radical containing 1 to 4 carbon atoms substituted by an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 7 carbon atoms, or a phenylalkyl radical in which the alkyl moiety contains 1 to 4 carbon atoms and is substituted by an alkoxycarbonyl radical in which the alkoxy moiety contains 1 to 4 carbon atoms, to convert the alkoxycarbonyl radical to a carboxy radical. The compounds of Formula III may be prepared by alkaline hydrolysis of an imine of Formula XI The imines of Formula XI may be prepared by cyclization of an isoquinoline derivative of Formula XII which may itself be prepared from compounds of Formula XIII by stirring in an organic solvent, in the presence of an alkali metal hydride. The compounds of Formula XIII may be prepared by reacting an alkali metal cyanide and toluene-p-sulphonyl chloride with an isoquinoline derivative of Formula XIV which may be prepared by reacting a tetrahydrofuran derivative of formula where R 7 is methyl or ethyl, With an 8-aminoisoquinoline derivative of formula The compounds of Formula I are used in pharmaceutical compositions.
GB3290174A
1973-07-27
1974-07-25
7h-indolizino-5,6,7-ij-isoquinoline derivatives
Expired
GB1442102A
(en)
Applications Claiming Priority (3)
Application Number
Priority Date
Filing Date
Title
FR7327649A
FR2244515A1
(en)
1973-07-27
1973-07-27
7H-Indolizino (5,6,7-i,j)-isoquinolines – as antibilharzial, anthelmintic and antimicrobial agents
FR7341616A
FR2252087A2
(en)
1973-11-22
1973-11-22
7H-Indolizino (5,6,7-i,j)-isoquinolines – as antibilharzial, anthelmintic and antimicrobial agents
FR7418808A
FR2272668A2
(en)
1974-05-30
1974-05-30
7H-Indolizino (5,6,7-i,j)-isoquinolines – as antibilharzial, anthelmintic and antimicrobial agents
Publications (1)
Publication Number
Publication Date
GB1442102A
true
GB1442102A
(en)
1976-07-07
Family
ID=27250154
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB3290174A
Expired
GB1442102A
(en)
1973-07-27
1974-07-25
7h-indolizino-5,6,7-ij-isoquinoline derivatives
Country Status (15)
Country
Link
US
(1)
US3946019A
(en)
JP
(1)
JPS5041899A
(en)
AR
(1)
AR204011A1
(en)
AT
(1)
AT335457B
(en)
CH
(1)
CH590282A5
(en)
DE
(1)
DE2436233A1
(en)
EG
(1)
EG11219A
(en)
GB
(1)
GB1442102A
(en)
HU
(1)
HU172290B
(en)
IE
(1)
IE39813B1
(en)
IL
(1)
IL45347A
(en)
NL
(1)
NL7409814A
(en)
OA
(1)
OA04812A
(en)
PH
(1)
PH10500A
(en)
ZM
(1)
ZM12174A1
(en)
Families Citing this family (2)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
FR2317880A1
(en)
*
1975-07-15
1977-02-11
Rhone Poulenc Ind
AGRICULTURAL COMPOSITIONS BASED ON 7H-INDOLIZINO (7,6,5-DE) ISOQUINOLEINE
US5227383A
(en)
*
1991-06-14
1993-07-13
The University Of Mississippi
Compounds and compositions useful as antifungal and antimycobacterial agents
Family Cites Families (2)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US3793328A
(en)
*
1969-11-03
1974-02-19
Upjohn Co
8benzoyl 1,2,3,4 tetrahydroquinoline
US3784550A
(en)
*
1971-08-13
1974-01-08
Squibb & Sons Inc
N-(2,3-dihydroquinobenzoxa(or thia)zepin-3-ylidene)-o-(substituted benzoyl)hydroxylamines
1974
1974-01-01
AR
AR254909A
patent/AR204011A1/en
active
1974-07-05
OA
OA55241A
patent/OA04812A/en
unknown
1974-07-19
NL
NL7409814A
patent/NL7409814A/en
not_active
Application Discontinuation
1974-07-25
HU
HU74RO00000789A
patent/HU172290B/en
unknown
1974-07-25
IE
IE1578/74A
patent/IE39813B1/en
unknown
1974-07-25
JP
JP49084700A
patent/JPS5041899A/ja
active
Pending
1974-07-25
IL
IL45347A
patent/IL45347A/en
unknown
1974-07-25
ZM
ZM121/74A
patent/ZM12174A1/en
unknown
1974-07-25
PH
PH16091A
patent/PH10500A/en
unknown
1974-07-25
US
US05/491,642
patent/US3946019A/en
not_active
Expired – Lifetime
1974-07-25
GB
GB3290174A
patent/GB1442102A/en
not_active
Expired
1974-07-26
DE
DE2436233A
patent/DE2436233A1/en
not_active
Withdrawn
1974-07-26
AT
AT616874A
patent/AT335457B/en
not_active
IP Right Cessation
1974-07-26
CH
CH1035174A
patent/CH590282A5/xx
not_active
IP Right Cessation
1974-07-27
EG
EG301/74A
patent/EG11219A/en
active
Also Published As
Publication number
Publication date
ATA616874A
(en)
1976-07-15
EG11219A
(en)
1977-01-31
NL7409814A
(en)
1975-01-29
AT335457B
(en)
1977-03-10
IE39813B1
(en)
1979-01-03
IL45347A0
(en)
1974-10-22
OA04812A
(en)
1980-10-31
US3946019A
(en)
1976-03-23
AR204011A1
(en)
1975-11-12
PH10500A
(en)
1977-05-17
AU7166374A
(en)
1976-01-29
IE39813L
(en)
1975-01-27
ZM12174A1
(en)
1975-03-21
CH590282A5
(en)
1977-07-29
JPS5041899A
(en)
1975-04-16
HU172290B
(en)
1978-07-28
IL45347A
(en)
1977-01-31
DE2436233A1
(en)
1975-02-13
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Legal Events
Date
Code
Title
Description
1976-11-17
PS
Patent sealed [section 19, patents act 1949]
1981-03-04
PCNP
Patent ceased through non-payment of renewal fee
