GB1383599A

GB1383599A – 9-3-amino-1-propenyl-9,10-dihydro-9,10-ethano-anthracenes and processes for their manufacture
– Google Patents

GB1383599A – 9-3-amino-1-propenyl-9,10-dihydro-9,10-ethano-anthracenes and processes for their manufacture
– Google Patents
9-3-amino-1-propenyl-9,10-dihydro-9,10-ethano-anthracenes and processes for their manufacture

Info

Publication number
GB1383599A

GB1383599A
GB762472A
GB762472A
GB1383599A
GB 1383599 A
GB1383599 A
GB 1383599A
GB 762472 A
GB762472 A
GB 762472A
GB 762472 A
GB762472 A
GB 762472A
GB 1383599 A
GB1383599 A
GB 1383599A
Authority
GB
United Kingdom
Prior art keywords
propen
ethano
group
alkyl
anthracene
Prior art date
1971-02-23
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
GB762472A
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.)

Novartis AG

Original Assignee
Ciba Geigy 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.)
1971-02-23
Filing date
1972-02-18
Publication date
1974-02-12

1971-02-23
Priority claimed from CH257771A
external-priority
patent/CH552558A/en

1972-01-17
Priority claimed from CH68872A
external-priority
patent/CH612805A5/xx

1972-02-18
Application filed by Ciba Geigy AG
filed
Critical
Ciba Geigy AG

1974-02-12
Publication of GB1383599A
publication
Critical
patent/GB1383599A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C211/00—Compounds containing amino groups bound to a carbon skeleton

C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms

C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring

C07C211/31—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by at least three rings

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C2603/00—Systems containing at least three condensed rings

C07C2603/02—Ortho- or ortho- and peri-condensed systems

C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings

C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings

C07C2603/24—Anthracenes; Hydrogenated anthracenes

Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE

Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

Y02P20/00—Technologies relating to chemical industry

Y02P20/50—Improvements relating to the production of bulk chemicals

Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

1383599 9(3 – Amino – propen – 1 – yl) – 9,10- ethano-anthracenes CIBA-GEIGY AG 18 Feb 1972 [23 Feb 1971 17 Jan 1972] 7624/72 Heading C2C Novel compounds of general Formula I in which R is a secondary or tertiary amino group, and the positions 1 to 8 of the ethanoanthracene ring may be substituted by up to four substituents, R A which may be the same or different and are selected from C 1-7 alkyl, C 1-7 alkoxy, C 2-7 alkenyloxy, C 1-7 alkyl thio, C 1-7 alkylsulphonyl, C 1-7 alkanoyl trifluoromethyl or halogen. R 10 is C 1-7 alkyl, C 2-7 alkenyl, halogen or hydrogen, R 0 , R1 0 and R11 0 are C 1-7 alkyl or hydrogen, Ae is a 1,2-ethylene radical which may be substituted in the 1- and/or 2- position by C 1-7 alkyl radicals are prepared by (1) reacting a 9-(3-Y-propen-1-yl)-9,10-ethanoanthracene in which Y is an esterified hydroxyl group with an amine (R-H), (2) reduction of (i) a 3-R-propyn-1-yl group using a Lindlar, Raney-Nickel or palladium catalyst or (ii) a group in which the nitrogen is bonded to one of its substituents by a double bond using a hydride or hydrogen plus a catalyst, (3) introduction of a 9,10-ethano radical into a 9-(3-R-propen- 1-yl)-anthracene by a Diels-Alder reaction or (4) conversion of a secondary amine into a tertiary amine. E and Z isomers of compounds of Formula I may be isolated. Novel starting materials are 9-(3-oxo-propen- 1-yl)-9,10-ethano-anthracenes which are prepared from 9-formyl anthracene by acetalization, the acetal obtained being reacted with an enthenyl ether to give a substituted or unsubstituted 3-(9-anthranyl) acrolein which is reacted with an unsubstituted or alkylated ethylene in an inert solvent to form 9-(3-oxo-propen-1-yl)-9,10-ethanoanthracene. This compound may be (a) reacted with a primary amine to form an imino compound which may be reduced as in method (2), (b) reduced using sodium borohydride to form the 3-hydroxy compound which may be esterified to form the 3-esterified hydroxy compound or (c) successively brominated and dehydrobrominated to form the (3-oxo-propyn-1-yl) compound which may be converted to the 3-R-propyn-1-yl group by reduction to an alcohol, conversion of the alcohol to a reactive ester which is reacted with a primary or secondary amine. Z – 9 – (3 – hydroxy – propen – 1 – yl) – 9,10- ethano-anthracene is converted to the trans isomer by reaction with perbenzoic acid to form the 1,2-epoxide, protection of the 3-hydroxyl group by forming a tetrahydropyranyl ether, reaction with diphenyl lithium and methyl iodide to form E-9-[3-(2-tetrahydropyranyloxy)- propen-1-yl]-9,10-ethano-anthracene and removal of the hydroxy protecting group by acid hydrolysis. Compounds of Formula I are anti-depressants and form with a suitable carrier a pharmaceutical preparation which may be administered orally or parenterally. Compounds of Formula I may also be used as additives to animal fodder.

GB762472A
1971-02-23
1972-02-18
9-3-amino-1-propenyl-9,10-dihydro-9,10-ethano-anthracenes and processes for their manufacture

Expired

GB1383599A
(en)

Applications Claiming Priority (3)

Application Number
Priority Date
Filing Date
Title

CH257771A

CH552558A
(en)

1971-02-23
1971-02-23
Substd 9-(3-aminoprop-1-enyl) -9,10-dihydro-9,10-ethanoanthracenes – – antidepressants

CH68872A

CH612805A5
(en)

1971-02-12
1972-01-17

CH66872

1972-01-17

Publications (1)

Publication Number
Publication Date

GB1383599A
true

GB1383599A
(en)

1974-02-12

Family
ID=27172295
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB762472A
Expired

GB1383599A
(en)

1971-02-23
1972-02-18
9-3-amino-1-propenyl-9,10-dihydro-9,10-ethano-anthracenes and processes for their manufacture

Country Status (19)

Country
Link

US
(1)

US3862131A
(en)

JP
(1)

JPS5813534B1
(en)

AR
(5)

AR203710A1
(en)

AT
(1)

AT317193B
(en)

BE
(1)

BE779664A
(en)

CA
(1)

CA987318A
(en)

CS
(4)

CS174198B2
(en)

DD
(1)

DD95388A5
(en)

DE
(1)

DE2207212A1
(en)

ES
(1)

ES400021A1
(en)

FR
(1)

FR2126354B1
(en)

GB
(1)

GB1383599A
(en)

HU
(1)

HU164398B
(en)

IE
(1)

IE36088B1
(en)

IL
(1)

IL38772A
(en)

NL
(1)

NL7202325A
(en)

NO
(1)

NO131594C
(en)

SE
(1)

SE381458B
(en)

SU
(5)

SU472498A3
(en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3965181A
(en)

*

1973-07-06
1976-06-22
Syntex (U.S.A.) Inc.
Tricyclic pharmacological agents, intermediates and methods of making

US4224344A
(en)

*

1974-12-13
1980-09-23
Sumitomo Chemical Company, Limited
Organic tricyclic compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3489799A
(en)

*

1967-09-26
1970-01-13
Ciba Geigy Corp
Ethano-anthracenes

1972

1972-02-15
IL
IL38772A
patent/IL38772A/en
unknown

1972-02-15
CA
CA134,715A
patent/CA987318A/en
not_active
Expired

1972-02-16
DE
DE19722207212
patent/DE2207212A1/en
not_active
Ceased

1972-02-16
IE
IE191/72A
patent/IE36088B1/en
unknown

1972-02-17
US
US227277A
patent/US3862131A/en
not_active
Expired – Lifetime

1972-02-18
GB
GB762472A
patent/GB1383599A/en
not_active
Expired

1972-02-18
SE
SE7201993A
patent/SE381458B/en
unknown

1972-02-21
ES
ES400021A
patent/ES400021A1/en
not_active
Expired

1972-02-22
SU
SU1752589A
patent/SU472498A3/en
active

1972-02-22
NL
NL7202325A
patent/NL7202325A/xx
not_active
Application Discontinuation

1972-02-22
AT
AT143072A
patent/AT317193B/en
not_active
IP Right Cessation

1972-02-22
CS
CS8641A
patent/CS174198B2/cs
unknown

1972-02-22
SU
SU1952298A
patent/SU510145A3/en
active

1972-02-22
CS
CS8640A
patent/CS174197B2/cs
unknown

1972-02-22
HU
HUCI1210A
patent/HU164398B/hu
unknown

1972-02-22
BE
BE779664A
patent/BE779664A/en
unknown

1972-02-22
CS
CS8642A
patent/CS174199B2/cs
unknown

1972-02-22
CS
CS8643A
patent/CS174200B2/cs
unknown

1972-02-22
DD
DD161039A
patent/DD95388A5/xx
unknown

1972-02-22
NO
NO538/72A
patent/NO131594C/no
unknown

1972-02-22
SU
SU1952304A
patent/SU482941A3/en
active

1972-02-23
JP
JP47018165A
patent/JPS5813534B1/ja
active
Pending

1972-02-23
AR
AR240667A
patent/AR203710A1/en
active

1972-02-23
FR
FR7206116A
patent/FR2126354B1/fr
not_active
Expired

1973

1973-01-01
AR
AR246763A
patent/AR204157A1/en
active

1973-01-01
AR
AR246765A
patent/AR203987A1/en
active

1973-02-23
AR
AR246766A
patent/AR201553A1/en
active

1973-02-23
AR
AR246764A
patent/AR201658A1/en
active

1973-07-27
SU
SU1952305A
patent/SU502602A3/en
active

1973-07-27
SU
SU1952306A
patent/SU498901A3/en
active

Also Published As

Publication number
Publication date

FR2126354A1
(en)

1972-10-06

AR203710A1
(en)

1975-10-15

BE779664A
(en)

1972-08-22

CA987318A
(en)

1976-04-13

IL38772A0
(en)

1972-04-27

CS174197B2
(en)

1977-03-31

IE36088B1
(en)

1976-08-18

CS174200B2
(en)

1977-03-31

HU164398B
(en)

1974-02-28

SU510145A3
(en)

1976-04-05

ES400021A1
(en)

1975-09-01

AR201553A1
(en)

1975-03-31

IE36088L
(en)

1972-08-23

CS174198B2
(en)

1977-03-31

SU482941A3
(en)

1975-08-30

IL38772A
(en)

1975-06-25

CS174199B2
(en)

1977-03-31

AT317193B
(en)

1974-08-12

SU502602A3
(en)

1976-02-05

FR2126354B1
(en)

1975-08-01

NO131594C
(en)

1975-06-25

NO131594B
(en)

1975-03-17

AR201658A1
(en)

1975-04-08

SU472498A3
(en)

1975-05-30

DD95388A5
(en)

1973-02-05

JPS5813534B1
(en)

1983-03-14

SU498901A3
(en)

1976-01-05

DE2207212A1
(en)

1972-09-07

SE381458B
(en)

1975-12-08

AR203987A1
(en)

1975-11-12

US3862131A
(en)

1975-01-21

AR204157A1
(en)

1975-11-28

NL7202325A
(en)

1972-08-25

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Legal Events

Date
Code
Title
Description

1975-06-25
PS
Patent sealed [section 19, patents act 1949]

1982-09-15
PCNP
Patent ceased through non-payment of renewal fee

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