SU843749A3 - Method of preparing 4a,9b-trans-hexahydro-gamma-carboline - Google Patents

Method of preparing 4a,9b-trans-hexahydro-gamma-carboline Download PDF

Info

Publication number
SU843749A3
SU843749A3 SU792753359A SU2753359A SU843749A3 SU 843749 A3 SU843749 A3 SU 843749A3 SU 792753359 A SU792753359 A SU 792753359A SU 2753359 A SU2753359 A SU 2753359A SU 843749 A3 SU843749 A3 SU 843749A3
Authority
SU
USSR - Soviet Union
Prior art keywords
hexahydro
trans
9b
salts
carboline
Prior art date
Application number
SU792753359A
Other languages
Russian (ru)
Inventor
МакКован Велч Виллард (младший)
Original Assignee
Пфайзер Инк (Фирма)
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
Priority to US79939277A priority Critical
Application filed by Пфайзер Инк (Фирма) filed Critical Пфайзер Инк (Фирма)
Application granted granted Critical
Publication of SU843749A3 publication Critical patent/SU843749A3/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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 two hetero rings
    • C07D471/04Ortho-condensed systems

Abstract

5-Phenyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles, which are substituted in position 2, and their salts of formula I, the symbols of which are explained in Claim 1, are described. These compounds and their salts are therapeutically active and can be used as medicaments for controlling schizophrenic symptoms. The pharmaceutical compositions are also described. The new compounds and their salts can be obtained by processes which are especially distinguished from others by the formation of the substituent in position 2; the latter is obtained by processes which each contain a reduction stage, from compounds which already have the pyridoindole system. <IMAGE>

Description

Example 1. d1-trans-5-phenyl-2, 3,4,4a, 9c-hexahydro-1H-pyrido- (4,3-b) -indole.

A suspension of 4.17 hydrochloride d) -trans-2-benzyl-5-phenyl-2,3,4,4a, 5,9v, -hexahydro-1H-pyrido- (4,3-b) -indole in 150 ml of absolute ethanol is hydrogenated at a pressure of 3.5 kgf / s and a temperature of 60-70 ° C using 1.0 g of 10% palladium on coal as a catalyst for more than 2 hours. The catalyst is then filtered and sufficient filtrate is added to the resulting filtrate the amount of ethyl ether to precipitate the hydrochloride of the desired product. Yield 2.76 g (87%), m.p. 235-237C.

The hydrochloric acid salt is converted into the free base of the puA by the separation between ether and dilute sodium hydroxide solution. The ether layer is dried over sodium sulfate and evaporated. The yield of the target product is 97%, so pl. 74-7bs.

Example 2. Trans-d1-8-fluoro-5-p-fluorophenyl-2, 3,4,4a, 5,9v-hexahydro-1H-pyrido- (4,3-b) -indole.

780 g of 5% palladium on coal containing 50% water, 1556.5 g {3.77 mol) trans-d1 -2-benzyl-8-fluoro-5-p-ft, are loaded into a clean enamelled high-pressure vessel, Orphenyl-2, 3,4,5,9 in-hexahydro-1H-pyrido- (4,3-in) -indol hydrochloride, 1167 ml of water and 86.1 l of methanol. The reactor is flushed with nitrogen and then with hydrogen, after which it is filled with hydrogen at a pressure of -3.5 kgf / cm and hydrogenated at 25-41 s until the absorption of hydrogen ceases, for about 2 hours. The vessel is opened, flushed nitrogen and the reaction mixture is filtered to remove the catalyst. After washing the filtrate with methanol, the latter is evaporated under reduced pressure. 28 liters of methylene heyurist and 87 liters of water containing 852 g of sodium hydroxide are added to the residue. The resulting mixture was stirred for 10 minutes (pH 12) and the layers were separated. The aqueous layer is extracted with a second portion.

methylene chloride (28 ml), the organic layers are mixed and washed with 26.5 l of water. The organic extracts are dried over anhydrous magnesium sulphate and concentrated on, adding hexane (95 L) to displace methylene chloride. The resulting suspension is cooled to 8 ° C, filtered, washed with hexane and dried. The yield of 1446 g (67%), so pl. 115-118 C.

Calculated,%: C, 71.31; H, 5.63; N 9.79; F 13.27.

n 16

No

Found,%: C 71.25; H 5.50;

N 9.76; F 13.28, Mass spectrum (m / e): 286 (100, m), 257 (50), 256 (72), 243 (61), 242 (57) 148 (32), 135 (36), 57 (79).

Claims (1)

1. Beygand Hilgetag. Experimental methods in organic chemistry. M., 1968, p.87.
SU792753359A 1977-05-23 1979-04-24 Method of preparing 4a,9b-trans-hexahydro-gamma-carboline SU843749A3 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US79939277A true 1977-05-23 1977-05-23

Publications (1)

Publication Number Publication Date
SU843749A3 true SU843749A3 (en) 1981-06-30

Family

ID=25175793

Family Applications (4)

Application Number Title Priority Date Filing Date
SU782615898A SU873883A3 (en) 1977-05-23 1978-05-18 Method of preparing hexahydro-gamma-carbolins or their salts
SU792753359A SU843749A3 (en) 1977-05-23 1979-04-24 Method of preparing 4a,9b-trans-hexahydro-gamma-carboline
SU792759902A SU818484A3 (en) 1977-05-23 1979-04-26 Method of preparing 4a,9b-trans-hexahydro-gamma-carbolin
SU792763595A SU841589A3 (en) 1977-05-23 1979-05-18 Method lf preparing hexahydro-gamma-carbolines or their salts

Family Applications Before (1)

Application Number Title Priority Date Filing Date
SU782615898A SU873883A3 (en) 1977-05-23 1978-05-18 Method of preparing hexahydro-gamma-carbolins or their salts

Family Applications After (2)

Application Number Title Priority Date Filing Date
SU792759902A SU818484A3 (en) 1977-05-23 1979-04-26 Method of preparing 4a,9b-trans-hexahydro-gamma-carbolin
SU792763595A SU841589A3 (en) 1977-05-23 1979-05-18 Method lf preparing hexahydro-gamma-carbolines or their salts

Country Status (31)

Country Link
JP (1) JPS5711912B2 (en)
AR (2) AR217688A1 (en)
AT (1) AT368995B (en)
AU (1) AU499618B1 (en)
BE (1) BE867249A (en)
CA (1) CA1094071A (en)
CH (1) CH634321A5 (en)
CS (1) CS207612B2 (en)
DD (4) DD138321A5 (en)
DE (1) DE2822465C2 (en)
DK (1) DK226678A (en)
EG (1) EG13590A (en)
FI (1) FI63402C (en)
FR (1) FR2392023B1 (en)
GB (1) GB1586655A (en)
GR (1) GR69985B (en)
HU (3) HU187782B (en)
IE (1) IE46975B1 (en)
IL (1) IL54755A (en)
IT (1) IT1096307B (en)
LU (1) LU79684A1 (en)
NL (1) NL7804210A (en)
NO (2) NO150204C (en)
NZ (1) NZ187333A (en)
PH (1) PH13756A (en)
PL (5) PL116944B1 (en)
PT (1) PT68058B (en)
SE (2) SE441448B (en)
SU (4) SU873883A3 (en)
YU (4) YU91478A (en)
ZA (1) ZA7802918B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4224329A (en) * 1979-01-23 1980-09-23 Pfizer Inc. 2-Substituted-trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles
US4451655A (en) * 1982-05-17 1984-05-29 Pfizer Inc. Process for preparing carboline derivatives and compounds used in their preparation
RU2106864C1 (en) * 1995-10-23 1998-03-20 Николай Серафимович Зефиров New approach to treatment of alzheimer's disease
US6974825B1 (en) 1996-12-20 2005-12-13 Astrazeneca Canada Inc. Compounds with analgesic effect
SE9604786D0 (en) 1996-12-20 1996-12-20 Astra Pharma Inc New compounds
SE9904675D0 (en) 1999-12-20 1999-12-20 Astra Pharma Inc Novel compounds
SE0101770D0 (en) 2001-05-18 2001-05-18 Astrazeneca Ab Novel compounds
SE0101769D0 (en) 2001-05-18 2001-05-18 Astrazeneca Ab Novel compounds
SE0101773D0 (en) 2001-05-18 2001-05-18 Astrazeneca Ab Novel compounds
SE0101771D0 (en) 2001-05-18 2001-05-18 Astrazeneca Ab Novel compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR205452A1 (en) * 1973-12-06 1976-05-07 Endo Lab Method for preparing novel trans-2, 3, 4, 4a, 5, 9b-hexahydro-5-phenyl-1H-pyrido (4,3-b) indoles
JPS50126699A (en) * 1974-03-20 1975-10-04
US4001263A (en) * 1974-04-01 1977-01-04 Pfizer Inc. 5-Aryl-1,2,3,4-tetrahydro-γ-carbolines

Also Published As

Publication number Publication date
AU499618B1 (en) 1979-04-26
PL114547B1 (en) 1981-02-28
DE2822465C2 (en) 1986-08-28
AT368995B (en) 1982-11-25
DE2822465A1 (en) 1978-11-30
YU40796B (en) 1986-06-30
PT68058A (en) 1978-06-01
PL114541B1 (en) 1981-02-28
CS207612B2 (en) 1981-08-31
SE441448B (en) 1985-10-07
YU221882A (en) 1983-01-21
PL206903A1 (en) 1979-10-22
DD145536A5 (en) 1980-12-17
HU187782B (en) 1986-02-28
IL54755A (en) 1981-02-27
SE448459B (en) 1987-02-23
NO831790L (en) 1978-11-24
HU188802B (en) 1986-05-28
YU91478A (en) 1983-01-21
IL54755D0 (en) 1978-07-31
IT1096307B (en) 1985-08-26
FI63402B (en) 1983-02-28
LU79684A1 (en) 1979-12-06
DD138321A5 (en) 1979-10-24
NO151862C (en) 1985-06-19
PT68058B (en) 1979-10-24
IE46975B1 (en) 1983-11-16
DD145537A5 (en) 1980-12-17
PH13756A (en) 1980-09-17
NO150204B (en) 1984-05-28
SU873883A3 (en) 1981-10-15
ATA369678A (en) 1982-04-15
SU841589A3 (en) 1981-06-23
YU221682A (en) 1983-01-21
YU221782A (en) 1983-01-21
NO781770L (en) 1978-11-24
IT7823673D0 (en) 1978-05-22
CH634321A5 (en) 1983-01-31
FI781612A (en) 1978-11-24
CA1094071A1 (en)
AR217688A1 (en) 1980-04-15
DD146186A5 (en) 1981-01-28
PL117107B1 (en) 1981-07-31
GB1586655A (en) 1981-03-25
SE7803625A (en) 1978-11-24
SE8305917L (en) 1983-10-27
BE867249A (en) 1978-11-20
EG13590A (en) 1982-03-31
GR69985B (en) 1982-07-22
IE781013L (en) 1978-11-23
FR2392023B1 (en) 1980-11-07
NO150204C (en) 1984-09-05
NL7804210A (en) 1978-11-27
ZA7802918B (en) 1979-06-27
AR221721A1 (en) 1981-03-13
JPS5711912B2 (en) 1982-03-08
SE8305917D0 (en) 1983-10-27
FR2392023A1 (en) 1978-12-22
NZ187333A (en) 1984-05-31
JPS53144600A (en) 1978-12-15
HU185009B (en) 1984-11-28
NO151862B (en) 1985-03-11
DK226678A (en) 1978-11-24
SU818484A3 (en) 1981-03-30
BE867249A1 (en)
PL116944B1 (en) 1981-07-31
CA1094071A (en) 1981-01-20
FI63402C (en) 1983-06-10

Similar Documents

Publication Publication Date Title
US4207324A (en) 1,2-Di-Substituted-4-haloimidazole-5-acetic acid derivatives and their use
SU1277895A3 (en) Method of producing cis-,endo-2-azabicyclo-(3,3,0)-octane-3-carboxylic acid or esters,or acid-additive salts thereof
SU1287755A3 (en) Method of producing n-methyl-11-aza-10-deoxo-10-dihydroerythromycin a
US5391770A (en) Process for preparing ascorbic acid
US4535157A (en) Process for making 6-desoxy-6-methylenenaloxone and 6-desoxy-6-methylenenaltrexone
CZ391091A3 (en) Crystalline paroxetin hydrochloride hemihydrate, process for producing thereof and pharmaceutical preparations in which it is comprised
SU553936A3 (en) Method for producing β-aminopenicillin esters
CA1178584A (en) 3,4-dihydro-5h-2,3-benzodiazepine derivatives and a process for the preparation thereof
EA011407B1 (en) Hydrates and polymorphs of 4-[[(7r)-8cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-4-6-oxo-2-piperidinyl]amino]-3-methoxy-n-(1-methyl-4-piperidinyl) benzamide, methods for the production thereof, and use thereof as medicaments
CH647222A5 (en) 9-deoxy-9a-methylene-isostere of pgi-2 and processes for their preparation.
US4146643A (en) Increasing vigilance or treating cerebral insufficiency with substituted vincamines
SU510999A3 (en) Method for producing (methoxymethyl-furylmethyl) 6,7-benzomorphanes of morphinanes
US2489232A (en) Synthesis of biotin
US2841584A (en) Hexahydropyridazine, derivatives thereof, and process
US4544764A (en) Interphenylene carbacyclin compound
US2831027A (en) Isocamphane compounds and processes for preparing the same
US2734904A (en) Xcxnhxc-nh
DK118403C (en) The alpha-amino penicillin derivatives and salts thereof for use as intermediates in the preparation of alpha-aminopenicillins.
DE2458164C2 (en)
SU1333239A3 (en) Method of producing hydrochlorides substituted with 2-[4-oxy-4-(n-fluorinephenyl)butyl]-4a,9b-trance-2.3,4.4a,5.9b-hexahydro-1h-pyrido(4.3-b)indoles
US4491668A (en) Process for preparing L-ascorbic acid
PT91640B (en) Process for the preparation of adamantane-1 derivatives
SU481155A3 (en) Production method - (furyl-methyl) morphinans
CA2726599C (en) Process for treprostinil salt preparation
Alcaraz et al. Asymmetric syntheses of 1-amino-2-phenyl (alkyl) cyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized monochiral olefines