GB1128079A – Process for the manufacture of new cyclohexane derivatives
– Google Patents
GB1128079A – Process for the manufacture of new cyclohexane derivatives
– Google Patents
Process for the manufacture of new cyclohexane derivatives
Info
Publication number
GB1128079A
GB1128079A
GB42872/66A
GB4287266A
GB1128079A
GB 1128079 A
GB1128079 A
GB 1128079A
GB 42872/66 A
GB42872/66 A
GB 42872/66A
GB 4287266 A
GB4287266 A
GB 4287266A
GB 1128079 A
GB1128079 A
GB 1128079A
Authority
GB
United Kingdom
Prior art keywords
cyano
phenyl
produced
radical
addition salts
Prior art date
1965-09-29
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
GB42872/66A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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.)
1965-09-29
Filing date
1966-09-26
Publication date
1968-09-25
1966-09-26
Application filed by Ciba AG
filed
Critical
Ciba AG
1968-09-25
Publication of GB1128079A
publication
Critical
patent/GB1128079A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Abstract
1,128,079. Cyclohexane derivatives. CIBA Ltd. 26 Sept., 1966 [29 Sept., 1965; 19 Aug., 1966], No. 42872/66. Heading C2C. Novel cyclohexane derivatives of the formula wherein X is an alkylene radical optionally interrupted by an oxygen atom, Ph is a phenyl radical which may be substituted by C 1-7 alkyl, hydroxyl, C 1-7 alkoxy ortrifluoromethyl radicals or by halogen atoms, and R is a cyano or carbalkoxy radical, and acid addition salts thereof are prepared (1) by condensing heterocyclic bases XN-H with the appropriate cyclohexanones R.PhC 6 H 8 O and reducing the cyclohexene derivatives RPhC 6 H 7 NX produced, (2) by reacting the bases XN-H with cyclohexane derivatives of the formula B.Ph.C 6 H 9 Z, where Z is a halogen atom or an arylsulphonyloxy radical, or (3) when R is carbalkoxy, by interconverting the corresponding cyano compound, e.g. by alcoholysis in the presence of sulphuric acid and ammonium chloride or by hydrolysing the cyano group to the carbamoyl group and hydrolysing the 1 -heterocyclyl – 4 – phenyl – 4 – carbamoyl-cyclohexanes produced to the corresponding 1 – heterocyclyl – 4 – phenyl – 4 – carboxycyclohexanes and esterifying these, e.g. with diazoalkanes, and, if desired, converting the free bases produced to the corresponding acid addition salts with inorganic or organic acids. The products of these processes may be cis- or (rans-forms or mixtures thereof, in which case the individual isomers may be isolated by conventional procedures, e.g. chromatography or fractional crystallization. 1 – Cyano – 1 – phenyl – 4 – (p – toluene – sulphonyloxy) – cyclohexane used as a starting material is prepared by reducing 4-cyano-4-phenylcyclohexanone with hydrogen or sodium borohydride and treating the 4-cyano-4-phenylcyclohexanol produced with p-toluenesulphonyl chloride. Therapeutic compositions useful as antitussives or analgesics contain compounds of the above formula or physiologically tolerable acid addition salts thereof, as active ingredient. The composition may be in a form suitable for enteral, parenteral or topical application.
GB42872/66A
1965-09-29
1966-09-26
Process for the manufacture of new cyclohexane derivatives
Expired
GB1128079A
(en)
Applications Claiming Priority (2)
Application Number
Priority Date
Filing Date
Title
CH1343965A
CH471124A
(en)
1965-09-29
1965-09-29
Process for the preparation of new cyclohexane derivatives
CH1203066
1966-08-19
Publications (1)
Publication Number
Publication Date
GB1128079A
true
GB1128079A
(en)
1968-09-25
Family
ID=25709432
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB42872/66A
Expired
GB1128079A
(en)
1965-09-29
1966-09-26
Process for the manufacture of new cyclohexane derivatives
Country Status (9)
Country
Link
US
(1)
US3530126A
(en)
AT
(3)
AT266152B
(en)
BE
(1)
BE687513A
(en)
BR
(1)
BR6683291D0
(en)
CH
(1)
CH471124A
(en)
DE
(1)
DE1670386A1
(en)
ES
(1)
ES331643A1
(en)
FR
(3)
FR1502852A
(en)
GB
(1)
GB1128079A
(en)
Families Citing this family (7)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
DE1793383C3
(en)
*
1968-09-10
1979-03-01
Knoll Ag, 6700 Ludwigshafen
4-Cyano-4-phenyl-aminocyclohexanes and their water-soluble salts, processes for their preparation and pharmaceuticals containing them
US4009278A
(en)
*
1969-03-19
1977-02-22
Sumitomo Chemical Company, Limited
Antimicrobial composition and method containing N-(3,5-dihalophenyl)-imide compounds
GB1242169A
(en)
*
1969-04-09
1971-08-11
Ucb Sa
Piperidine derivatives
DE3382646D1
(en)
*
1982-08-26
1993-01-28
Merck Patent Gmbh
CYCLOHEXAN DERIVATIVES AND THEIR USE AS A COMPONENT LIQUID CRYSTAL DIELECTRIC.
DE3231707A1
(en)
*
1982-08-26
1984-03-01
Merck Patent Gmbh, 6100 Darmstadt
Cyclohexane derivatives
US4595759A
(en)
*
1983-08-19
1986-06-17
Pennwalt Corporation
Cyclohexane carboxylic acids and derivatives thereof as antidysrhythmic agents
US4760146A
(en)
*
1986-02-18
1988-07-26
Pennwalt Corporation
Cyclohexene carboxylic esters and amides as antidysrhythmic agents
Family Cites Families (1)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US2858316A
(en)
*
1956-11-16
1958-10-28
Union Chimique Belge Sa
New piperidine derivatives
1965
1965-09-29
CH
CH1343965A
patent/CH471124A/en
not_active
IP Right Cessation
1966
1966-09-07
US
US577621A
patent/US3530126A/en
not_active
Expired – Lifetime
1966-09-20
DE
DE19661670386
patent/DE1670386A1/en
active
Pending
1966-09-26
GB
GB42872/66A
patent/GB1128079A/en
not_active
Expired
1966-09-27
ES
ES0331643A
patent/ES331643A1/en
not_active
Expired
1966-09-27
FR
FR77844A
patent/FR1502852A/en
not_active
Expired
1966-09-28
BE
BE687513D
patent/BE687513A/xx
unknown
1966-09-28
AT
AT527167A
patent/AT266152B/en
active
1966-09-28
AT
AT527267A
patent/AT266153B/en
active
1966-09-28
AT
AT909766A
patent/AT262303B/en
active
1966-09-29
BR
BR183291/66A
patent/BR6683291D0/en
unknown
1966-12-23
FR
FR88619A
patent/FR5842M/fr
not_active
Expired
1966-12-23
FR
FR88618A
patent/FR5841M/fr
not_active
Expired
Also Published As
Publication number
Publication date
FR5841M
(en)
1968-03-04
ES331643A1
(en)
1967-12-01
BE687513A
(en)
1967-03-28
FR1502852A
(en)
1967-11-24
DE1670386A1
(en)
1970-11-05
AT266153B
(en)
1968-11-11
CH471124A
(en)
1969-04-15
BR6683291D0
(en)
1973-12-26
FR5842M
(en)
1968-03-04
US3530126A
(en)
1970-09-22
AT262303B
(en)
1968-06-10
AT266152B
(en)
1968-11-11
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