GB1335261A - Isoquinoline derivatives - Google Patents

Isoquinoline derivatives

Info

Publication number
GB1335261A
GB1335261A GB45471A GB45471A GB1335261A GB 1335261 A GB1335261 A GB 1335261A GB 45471 A GB45471 A GB 45471A GB 45471 A GB45471 A GB 45471A GB 1335261 A GB1335261 A GB 1335261A
Authority
GB
United Kingdom
Prior art keywords
compound
formula
alkoxy
alkyl
reducing
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
GB45471A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1335261A publication Critical patent/GB1335261A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/18—Aralkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1335261 Isoquinolines HOFFMANN-LA ROCHE & CO AG 5 Jan 1971 [6 Jan 1970] 454/71 Heading C2C Compounds of the general formula (R = OH, C 1-4 alkoxy; R 1 = H, OH, C 1-4 alkoxy or R + R 1 = OCH 2 O; R 2 = H, C 1-4 alkyl; R 3 = C 1-4 alkyl, Ph(C 1-4 alkyl); R 4 = halogen, NO 2 NH 2 , C 1-4 alkylamino, di-(C 1-4 alkyl)amino; n = 1,2) and their acid addition salts are prepared by (a) cyclizing a compound of the formula (X = OH, acyloxy, halogen), (b) alkylating or aralkylating a compound of the formula (R 40 = halogen, NO 2 , dialkylamino), (c) reducing a compound of the formula (R 0 = C 1-4 alkoxy; R 10 = H, C 1-4 alkoxy or R 0 + R 10 = OCH 2 O; R 30 = C 1-4 alkyl, Ph(C 2-4 alkyl); R 41 = halogen, dialkylamino) under acidic conditions or reducing a compound of the formula (d) reducing a compound of the formula (R 11 = OH, C 1-4 alkoxy or R + R 11 = OCH 2 O; Y = anion), (e) reducing a compound of the formula (f) when R and/or R 1 = OH, subjecting a corresponding compound in which R and/or R 1 = alkoxy to acidic ether-cleavage, (g) when R 4 = NH 2 (R 3 not PhCH 2 ), reducing a corresponding compound in which R 4 = NO 2 , (h) when R 4 = alkylamino or dialkylamino, monoalkylating a corresponding compound in which R 4 = NH 2 or alkylamino, (i) when R and/or R 1 = OH (R 3 not PhCH 2 , R 4 not NO 2 ), hydrolytically debenzylating a corresponding compound but in which R and/or R 1 = PhCH 2 O, (j) when the product is optically active, resolving the racemate or using an optically active starting material or (k) when the product contains at least two asymmetric carbon atoms, separating an individual racemate from the diastereomer mixture, optionally followed in each case by salt formation. The starting materials are prepared by the following routes The above compounds are antidepressants, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.
GB45471A 1970-01-06 1971-01-05 Isoquinoline derivatives Expired GB1335261A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH10370A CH527194A (en) 1970-01-06 1970-01-06 Process for the preparation of isoquinoline derivatives

Publications (1)

Publication Number Publication Date
GB1335261A true GB1335261A (en) 1973-10-24

Family

ID=4179328

Family Applications (1)

Application Number Title Priority Date Filing Date
GB45471A Expired GB1335261A (en) 1970-01-06 1971-01-05 Isoquinoline derivatives

Country Status (19)

Country Link
JP (1) JPS5515476B1 (en)
AT (1) AT303041B (en)
BE (1) BE761219A (en)
CA (1) CA999866A (en)
CH (2) CH527194A (en)
DE (1) DE2062001C2 (en)
DK (1) DK125021B (en)
ES (1) ES387016A1 (en)
FI (1) FI49503C (en)
FR (1) FR2081412B1 (en)
GB (1) GB1335261A (en)
IE (1) IE34859B1 (en)
IL (1) IL35916A (en)
NL (1) NL171444C (en)
NO (1) NO135315C (en)
PH (1) PH9682A (en)
SE (3) SE368401B (en)
YU (1) YU33660B (en)
ZA (1) ZA708590B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2271566A (en) * 1992-10-14 1994-04-20 Merck & Co Inc HIV integrase inhibitors
WO2006138714A2 (en) * 2005-06-17 2006-12-28 Janssen Pharmaceutica N.V. Naphthyridine compounds

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4595688A (en) * 1983-06-23 1986-06-17 Mcneilab, Inc. Hexahydropyrrolo[2,1-a]isoquinoline derivatives and antidepressant use thereof
ZA844402B (en) * 1983-06-23 1986-01-29 Mcneil Pharmaceutical Hexahydropyrrolo(2,1-a)isoquinoline derivatives
US4719216A (en) * 1983-06-23 1988-01-12 Mcneilab, Inc. Hexahydropyrrolo(2,1-A)isoquinoline derivatives as antidepressants
RU2309953C2 (en) 1999-11-03 2007-11-10 Эймр Текнолоджи, Инк. Aryl- and heteroaryl-substituted tetrahydroisoquinolines, pharmaceutical composition and method for treatment based on thereof
CN100436420C (en) * 1999-11-03 2008-11-26 Amr科技公司 4-phenyl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin
US7163949B1 (en) * 1999-11-03 2007-01-16 Amr Technology, Inc. 4-phenyl substituted tetrahydroisoquinolines and use thereof
EP1113007A1 (en) 1999-12-24 2001-07-04 Pfizer Inc. Tetrahydroisoquinoline compounds as estrogen agonists/antagonists
CA2415532C (en) 2000-07-11 2010-05-11 Albany Molecular Research, Inc. Novel 4-phenyl substituted tetrahydroisoquinolines therapeutic use thereof
KR101412339B1 (en) 2004-07-15 2014-06-25 알바니 몰레큘라 리써치, 인크. Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
CN101495184A (en) 2005-07-15 2009-07-29 Amr科技公司 Aryl-and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
AR071997A1 (en) 2008-06-04 2010-07-28 Bristol Myers Squibb Co CRYSTAL FORM OF 6 - ((4S) -2-METHYL-4- (2-NAFTIL) -1,2,3,4-TETRAHYDROISOQUINOLIN-7-IL) PIRIDAZIN-3-AMINA
US9156812B2 (en) 2008-06-04 2015-10-13 Bristol-Myers Squibb Company Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine
CA2760837C (en) 2009-05-12 2018-04-03 Albany Molecular Research, Inc. 7-([1,2,4]triazolo[1,5-.alpha.]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline and use thereof
US8815894B2 (en) 2009-05-12 2014-08-26 Bristol-Myers Squibb Company Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline and use thereof
US9034899B2 (en) 2009-05-12 2015-05-19 Albany Molecular Research, Inc. Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1670694B2 (en) * 1966-05-05 1976-07-22 Hoechst Ag, 6000 Frankfurt METHOD FOR MANUFACTURING TETRAHYDROISOCHINOLINES

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2271566A (en) * 1992-10-14 1994-04-20 Merck & Co Inc HIV integrase inhibitors
WO2006138714A2 (en) * 2005-06-17 2006-12-28 Janssen Pharmaceutica N.V. Naphthyridine compounds
WO2006138714A3 (en) * 2005-06-17 2007-03-15 Janssen Pharmaceutica Nv Naphthyridine compounds
US7417054B2 (en) 2005-06-17 2008-08-26 Janssen Pharmaceutica N.V. Naphthyridine compounds

Also Published As

Publication number Publication date
NL7018956A (en) 1971-07-08
SE386672B (en) 1976-08-16
PH9682A (en) 1976-02-10
DE2062001A1 (en) 1971-07-15
IL35916A0 (en) 1971-02-25
BE761219A (en) 1971-07-05
NO135315B (en) 1976-12-13
NL171444C (en) 1983-04-05
SE368401B (en) 1974-07-01
DE2062001C2 (en) 1986-10-16
ZA708590B (en) 1971-09-29
FR2081412B1 (en) 1974-04-12
ES387016A1 (en) 1976-05-01
IL35916A (en) 1973-11-28
DK125021B (en) 1972-12-18
IE34859L (en) 1971-07-06
FI49503C (en) 1975-07-10
IE34859B1 (en) 1975-09-03
FI49503B (en) 1975-04-01
FR2081412A1 (en) 1971-12-03
CA999866A (en) 1976-11-16
CH538477A (en) 1973-06-30
SE399879B (en) 1978-03-06
YU1971A (en) 1977-06-30
NO135315C (en) 1977-03-23
NL171444B (en) 1982-11-01
CH527194A (en) 1972-08-31
JPS5515476B1 (en) 1980-04-23
AT303041B (en) 1972-11-10
YU33660B (en) 1977-12-31

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee