GB1515540A - 4-amino-trans-decahydroquinoline derivatives - Google Patents

4-amino-trans-decahydroquinoline derivatives

Info

Publication number
GB1515540A
GB1515540A GB51507/75A GB5150775A GB1515540A GB 1515540 A GB1515540 A GB 1515540A GB 51507/75 A GB51507/75 A GB 51507/75A GB 5150775 A GB5150775 A GB 5150775A GB 1515540 A GB1515540 A GB 1515540A
Authority
GB
United Kingdom
Prior art keywords
group
carbonyl
alkyl
reacting
trans
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
Application number
GB51507/75A
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.)
Labaz SA
Original Assignee
Labaz 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.)
Filing date
Publication date
Application filed by Labaz SA filed Critical Labaz SA
Priority to GB51507/75A priority Critical patent/GB1515540A/en
Priority to IE2613/76A priority patent/IE44355B1/en
Priority to ZA00767112A priority patent/ZA767112B/en
Priority to NZ182758A priority patent/NZ182758A/en
Priority to AU20328/76A priority patent/AU509897B2/en
Priority to NL7613629A priority patent/NL7613629A/en
Priority to CA267,706A priority patent/CA1077040A/en
Priority to AR265813A priority patent/AR214988A1/en
Priority to CH1565976A priority patent/CH618970A5/en
Priority to MX765223A priority patent/MX5798E/en
Priority to FR7637621A priority patent/FR2335224A1/en
Priority to FI763603A priority patent/FI63023C/en
Priority to OA56017A priority patent/OA05515A/en
Priority to JP51151456A priority patent/JPS6022711B2/en
Priority to DD7600196381A priority patent/DD128709A5/en
Priority to BE173281A priority patent/BE849431A/en
Priority to NO764251A priority patent/NO145916C/en
Priority to DE2656678A priority patent/DE2656678C2/en
Priority to DK564876A priority patent/DK564876A/en
Priority to HU76LA900A priority patent/HU175391B/en
Priority to SE7614105A priority patent/SE434396B/en
Priority to SU762428755A priority patent/SU633476A3/en
Priority to PT65970A priority patent/PT65970B/en
Priority to IT30441/76A priority patent/IT1065969B/en
Priority to YU3071/76A priority patent/YU39980B/en
Priority to ES454285A priority patent/ES454285A1/en
Priority to AT932076A priority patent/AT357535B/en
Priority to PL1976194452A priority patent/PL101143B1/en
Priority to US05/884,705 priority patent/US4173636A/en
Publication of GB1515540A publication Critical patent/GB1515540A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4

Abstract

1515540 4 - Amino - trans - decahydroquinoline derivatives LABAZ 24 Nov 1976 [16 Dec 1975] 51507/75 Heading C2C Novel trans decahydroquinoline derivatives of the Formula I and pharmaceutically acceptable acid addition salts thereof, wherein R<SP>1</SP> is alkyl, alkoxy, dialkylamino, a saturated heterocyclic ring attached through a ring nitrogen atom, an unsaturated heterocyclic group or an optionally substituted phenyl, R<SP>2</SP> is alkyl, optionally substituted phenyl, naphthyl, unsaturated heterocyclic optionally substituted by alkyl, aralkyl, aralkenyl or alicyclic and R<SP>3</SP> is alkyl substituted furyl, aralkyl, aralkenyl or a group where A is C 1-4 -alkylene, Y is oxygen, sulphur, carbonyl > C = NOH, >C = NNH 2 or sulphoxide or a group X R<SP>4</SP> and R<SP>5</SP> each are hydrogen, halogen, methyl, methoxy or acetyl and n is zero or 1, with the proviso that when n is zero, Y is carbonyl, where alkyl groups unless otherwise specified have 1 to 4 carbon atoms, may be prepared, when R 1 is other than dialkylamino or saturated heterocyclic group attached by a ring nitrogen atom and when R<SP>3</SP> is a group II, Y is other than hydroxyiminomethylene or hydrazonomethylene by reacting a compound III with R<SP>1</SP>COCl or (R<SP>1</SP>CO) 2 O or when R<SP>1</SP> is dialkylamino or a saturated heterocyclic group attached by a ring nitrogen atom, and when R<SP>3</SP> is a group II, Y is other than hydroxyiminomethylone or hydrazonomethylene by reacting a compound VI with an amine R<SP>1</SP>H, optionally followed by acid addition salt formation and/or reacting a carbonyl at Y with hydroxylamine or hydrazine to form a hydroxylimino methylene or a carbonyl hydrazonomethylene. Intermediates of the Formula III are prepared by reacting 4-oxo-trans-decahydroquinoline with an amine R<SP>2</SP>NH 2 and reducing the imine so formed to produce a compound VIII which is reacted with R<SP>3</SP>-Hal, where Hal is chlorine, bromine or iodine. When R<SP>3</SP> is a group II and Y is carbonyl, the carbonyl group is protected with a group X and thereafter optionally hydrolysed. The isomers of the compound VIII are separated. Pharmaceutical compositions of the compounds I with the usual excipients show analgesic activity when administered orally, parenterally or rectally. The compounds I in which R<SP>1</SP> is alkoxy also show antihypertensive action.
GB51507/75A 1975-12-16 1975-12-16 4-amino-trans-decahydroquinoline derivatives Expired GB1515540A (en)

Priority Applications (29)

Application Number Priority Date Filing Date Title
GB51507/75A GB1515540A (en) 1975-12-16 1975-12-16 4-amino-trans-decahydroquinoline derivatives
IE2613/76A IE44355B1 (en) 1975-12-16 1976-11-26 4-amino-trans-decahydroquinoline derivatives
ZA00767112A ZA767112B (en) 1975-12-16 1976-11-29 Heterocyclic compounds and processes for preparing the same
NZ182758A NZ182758A (en) 1975-12-16 1976-11-29 1-substituled-4(n-acyl-n-substituted amino) -trans-decahyclroiso-quinolines (forms a or b)
AU20328/76A AU509897B2 (en) 1975-12-16 1976-12-07 4-amino-trans-decahydroquinoline derivatives
NL7613629A NL7613629A (en) 1975-12-16 1976-12-08 PROCESS FOR THE PREPARATION OF 4-AMINO-TRANS- DECAHYDROCHINOLINE DERIVATIVES.
CA267,706A CA1077040A (en) 1975-12-16 1976-12-13 Pharmaceutically active decahydroquinoline derivatives
AR265813A AR214988A1 (en) 1975-12-16 1976-12-13 A PROCEDURE FOR PREPARING 1-SUBSTITUTED-4-AMINO-SUBSTITUTED DERIVATIVES OF DECAHYDROQUINOLINE
CH1565976A CH618970A5 (en) 1975-12-16 1976-12-13 Process for the preparation of 4-amido-trans-decahydroquinoline derivatives
MX765223A MX5798E (en) 1975-12-16 1976-12-14 PROCEDURE FOR THE PREPARATION OF 4-AMINO-TRANS-DECAHYDROKINOLINE DERIVATIVES
FR7637621A FR2335224A1 (en) 1975-12-16 1976-12-14 NEW DECAHYDROQUINOLEINE DERIVATIVES, THEIR PREPARATION PROCESSES AND THE THERAPEUTIC COMPOSITIONS CONTAINING THEM
FI763603A FI63023C (en) 1975-12-16 1976-12-15 FOERFARANDE FOER FRAMSTAELLNING AV SMAERTLINDRANDE 4-AMINO-TRANS-DEKAHYDROKINOLINDERIVAT
OA56017A OA05515A (en) 1975-12-16 1976-12-15 Process for the preparation of new decahydroquinoline derivatives.
JP51151456A JPS6022711B2 (en) 1975-12-16 1976-12-15 Trans-decahydroquinoline derivatives, their production methods, and pharmaceuticals containing the same
DD7600196381A DD128709A5 (en) 1975-12-16 1976-12-15 PROCESS FOR PREPARING DEKAHYDROCHINOLINE DERIVATIVES
BE173281A BE849431A (en) 1975-12-16 1976-12-15 NEW DECAHYDROQUINOLEINE DERIVATIVES, THEIR PREPARATIONS AND THE THERAPEUTIC COMPOSITIONS CONTAINING THEM
NO764251A NO145916C (en) 1975-12-16 1976-12-15 ANALOGUE PROCEDURE FOR THE PREPARATION OF PHARMACOLOGICAL ACTIVE 4-AMINO-TRANS-DECA HYDROKINOLINE DERIVATIVES
DE2656678A DE2656678C2 (en) 1975-12-16 1976-12-15 4-Amino-trans-decahydroquinoline derivatives and processes for their preparation and pharmaceutical compositions containing them
DK564876A DK564876A (en) 1975-12-16 1976-12-15 HETEROCYCLIC COMPOUNDS AND MANUFACTURING METHOD
HU76LA900A HU175391B (en) 1975-12-16 1976-12-15 Process for producing 4-amino-trans-decahydroquinoline derivatives and pharmaceutical compositions containing them as active agents
SE7614105A SE434396B (en) 1975-12-16 1976-12-15 ANALOGY PROCEDURE FOR PREPARATION OF 4-AMINO-TRANSDEKAH HYDROKINOLINE DERIVATIVES
SU762428755A SU633476A3 (en) 1975-12-16 1976-12-15 Method of obtaining 4-amino-trans-deca-hydroquinoline derivatives or salts thereof
PT65970A PT65970B (en) 1975-12-16 1976-12-15 PROCESS FOR THE PREPARATION OF A PHARMACEUTICAL COMPOSITION
IT30441/76A IT1065969B (en) 1975-12-16 1976-12-15 HETEROCYCLIC COMPOUNDS AND PROCEDURES FOR PREPARING THE SAME
YU3071/76A YU39980B (en) 1975-12-16 1976-12-16 Process for obtaining 4-amino-trans-decahydroquinoline derivatives
ES454285A ES454285A1 (en) 1975-12-16 1976-12-16 4-amino-trans-decahydroquinoline derivatives
AT932076A AT357535B (en) 1975-12-16 1976-12-16 METHOD FOR PRODUCING NEW 4-AMINO-TRANSDECAHYDROCHINOLINE DERIVATIVES AND THEIR ACID ADDITION SALTS
PL1976194452A PL101143B1 (en) 1975-12-16 1976-12-16 METHOD OF MAKING 4-AMINO-TRANS-DEKAHYDROQUINOLINE DERIVATIVES
US05/884,705 US4173636A (en) 1975-12-16 1978-03-08 Decahydroquinolines, pharmaceutical compositions and methods of use

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB51507/75A GB1515540A (en) 1975-12-16 1975-12-16 4-amino-trans-decahydroquinoline derivatives

Publications (1)

Publication Number Publication Date
GB1515540A true GB1515540A (en) 1978-06-28

Family

ID=10460296

Family Applications (1)

Application Number Title Priority Date Filing Date
GB51507/75A Expired GB1515540A (en) 1975-12-16 1975-12-16 4-amino-trans-decahydroquinoline derivatives

Country Status (28)

Country Link
JP (1) JPS6022711B2 (en)
AR (1) AR214988A1 (en)
AT (1) AT357535B (en)
AU (1) AU509897B2 (en)
BE (1) BE849431A (en)
CA (1) CA1077040A (en)
CH (1) CH618970A5 (en)
DD (1) DD128709A5 (en)
DE (1) DE2656678C2 (en)
DK (1) DK564876A (en)
ES (1) ES454285A1 (en)
FI (1) FI63023C (en)
FR (1) FR2335224A1 (en)
GB (1) GB1515540A (en)
HU (1) HU175391B (en)
IE (1) IE44355B1 (en)
IT (1) IT1065969B (en)
MX (1) MX5798E (en)
NL (1) NL7613629A (en)
NO (1) NO145916C (en)
NZ (1) NZ182758A (en)
OA (1) OA05515A (en)
PL (1) PL101143B1 (en)
PT (1) PT65970B (en)
SE (1) SE434396B (en)
SU (1) SU633476A3 (en)
YU (1) YU39980B (en)
ZA (1) ZA767112B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005097806A1 (en) * 2004-03-26 2005-10-20 Eli Lilly And Company Compounds and methods for treating dyslipidemia

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2592879B1 (en) * 1986-01-13 1988-04-29 Roussel Uclaf NOVEL DECAHYDROQUINOLEIN DERIVATIVES, PROCESS FOR THEIR PREPARATION, PREPARATION INTERMEDIATES, THEIR APPLICATION AS MEDICAMENTS AND COMPOSITIONS CONTAINING THEM

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005097806A1 (en) * 2004-03-26 2005-10-20 Eli Lilly And Company Compounds and methods for treating dyslipidemia
US7470705B2 (en) 2004-03-26 2008-12-30 Eli Lilly And Company Compounds and methods for treating dyslipidemia

Also Published As

Publication number Publication date
FI63023B (en) 1982-12-31
ATA932076A (en) 1979-12-15
FI63023C (en) 1983-04-11
IT1065969B (en) 1985-03-04
ZA767112B (en) 1978-07-26
AT357535B (en) 1980-07-10
HU175391B (en) 1980-07-28
BE849431A (en) 1977-06-15
IE44355L (en) 1977-06-16
OA05515A (en) 1981-04-30
ES454285A1 (en) 1977-11-16
FR2335224B1 (en) 1980-03-14
FI763603A (en) 1977-06-17
CH618970A5 (en) 1980-08-29
SE434396B (en) 1984-07-23
SE7614105L (en) 1977-06-17
NO764251L (en) 1977-06-17
MX5798E (en) 1984-07-25
AU2032876A (en) 1978-06-15
JPS52102284A (en) 1977-08-27
JPS6022711B2 (en) 1985-06-03
YU307176A (en) 1982-08-31
NZ182758A (en) 1979-03-28
DK564876A (en) 1977-06-17
SU633476A3 (en) 1978-11-15
DD128709A5 (en) 1977-12-07
FR2335224A1 (en) 1977-07-15
AU509897B2 (en) 1980-05-29
DE2656678A1 (en) 1977-06-30
NO145916B (en) 1982-03-15
YU39980B (en) 1985-06-30
IE44355B1 (en) 1981-11-04
PT65970B (en) 1978-06-16
DE2656678C2 (en) 1986-12-04
NL7613629A (en) 1977-06-20
PT65970A (en) 1977-01-01
AR214988A1 (en) 1979-08-31
NO145916C (en) 1982-06-23
PL101143B1 (en) 1978-12-30
CA1077040A (en) 1980-05-06

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PCNP Patent ceased through non-payment of renewal fee