AU1874683A – Propylamine derivatives
– Google Patents
AU1874683A – Propylamine derivatives
– Google Patents
Propylamine derivatives
Info
Publication number
AU1874683A
AU1874683A
AU18746/83A
AU1874683A
AU1874683A
AU 1874683 A
AU1874683 A
AU 1874683A
AU 18746/83 A
AU18746/83 A
AU 18746/83A
AU 1874683 A
AU1874683 A
AU 1874683A
AU 1874683 A
AU1874683 A
AU 1874683A
Authority
AU
Australia
Prior art keywords
compound
formula
lower alkyl
group
salt
Prior art date
1982-09-07
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.)
Granted
Application number
AU18746/83A
Other versions
AU566564B2
(en
Inventor
Jeffrey W.H. Watthey
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.)
1982-09-07
Filing date
1983-09-06
Publication date
1984-03-15
1983-09-06
Application filed by Ciba Geigy AG
filed
Critical
Ciba Geigy AG
1984-03-15
Publication of AU1874683A
publication
Critical
patent/AU1874683A/en
1987-10-22
Application granted
granted
Critical
1987-10-22
Publication of AU566564B2
publication
Critical
patent/AU566564B2/en
2003-09-06
Anticipated expiration
legal-status
Critical
Status
Ceased
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
C07D295/08—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 singly bound oxygen or sulfur atoms
C07D295/084—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
C07D295/092—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
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
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
A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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
A61P25/00—Drugs for disorders of the nervous system
A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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
A61P25/24—Antidepressants
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
A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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
A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer’s disease or other forms of dementia
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
C07C227/04—Formation of amino groups in compounds containing carboxyl groups
C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
Abstract
For the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE 1. A compound of the general formula I see diagramm : EP0102929,P33,F1 Wherein each of R1 and R2 independently of the other represents hydrogen or lower alkyl ; or R1 and R2 together with the adjacent nitrogen atom represent piperidino or pyrrolidino or a five- or six-membered saturated heterocyclic ring containing NH, N-lower alkyl, O or S ; R3 represents hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl ; Ar represents phenyl or phenyl substituted by one to three substituents selected from the group consisting of lower alkyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, lower alkylmercapto, lower alkylsulfinyl, lower alkylsulfonyl, halogen and trifluoromethyl, or by on lower alkylenedioxy ; and X represents O, S or N-lower alkyl ; and n represents an integer 1, 2 or 3 ; or an N-oxide thereof ; an acid addition salt thereof ; of an N-lower alkyl or N-benzyl quaternary salt thereof ; with the exception of the compound of formula I wherein R1 and R2 represent ethyl, R3 represents hydrogen, Ar represents phenyl, X represents O, and n is 3, or a salt thereof ; with the groups qualified by the term «lower» containing at most 7 carbon atoms. For the Contracting State : AT 1. A process for the preparation of a novel propylamine derivative of the general formula I see diagramm : EP0102929,P37,F1 Wherein each of R1 and R2 independently of the other represents hydrogen or lower alkyl ; or R1 and R2 together with the adjacent nitrogen atom represent piperidono or pyrrodino or a five- or six-membered saturated heterocyclic ring containing NH, N-lower alkyl, O or S ; R3 represents hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl ; Ar represents phenyl or phenyl substituted by one to three substituents selected from the group consisting of lower alkyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, lower alkylmercapto, lower alkylsulfinyl, lower alkylsulfonyl, halogen and trifluoromethyl, or by on lower alkylenedioxy ; and X represents O, S or N-lower alkyl ; and n represents an integer 1, 2 or 3 ; or of an N-oxide thereof ; an acid addition salt thereof ; of an N-lower alkyl or N-benzyl quaternary salt thereof ; with the exception of the compound of formula I wherein R1 and R2 represent ethyl, R3 represents hydrogen, Ar represents phenyl, X represents O, and n is 3, or a salt thereof ; with the groups qualified by the term «lower» containing at most 7 carbon atoms ; which process comprises a) condensing a compound of the formula II see diagramm : EP0102929,P37,F2 or an acid addition salt thereof, with a compound of the formula III AR-Y(III) wherein R1 , R2 , R3 , n and Ar are as defined above, one of the symbols W and Y represents a group XH or XH in a metal salt from, in which X is as defined above, and the other one represents the group XH in a reactive esterified form thereof or as an N,N’-disubstituted isourea or isothiourea derivative ; or b) alkylating an amine of the formula IV see diagramm : EP0102929,P37,F3 or an acid addition salt thereof, with a compound of the formula V see diagramm : EP0102929,P38,F4 in which Z is a hydrogen atom together with a reactive esterified hydroxyl group of the oxo group and Ar, X, R3 and n are as defined above, and if Z is the oxo group, said alkylation is carried out under reductive conditions ; or c) reducing a compound structurally analogous to a compound of formula I as defined above, wherein an oxo group is present on at least one carbon atom adjacent to the amino nitrogen ; or d) saturating with hydrogen a multiple bond or multiple bonds in a compound structurally analogous to the compound of formula I as defined above and wherein one or two double bonds are present in the aliphatic moiety of the molecule inclusive of the amino group ; or e) removing the radial R0 from a compound of the formula VI see diagramm : EP0102929,P38,F5 wherein R2 , R3 , X, n and Ar are as defined above and R0 is an amino proctective group, to obtain a compound of formula in which R1 is hyrogen ; or f) reducing a compound of the formula VII see diagramm : EP0102929,P38,F5 wherein T represents cyano or azidomethyl ; and R3 , X, n and Ar are as defined above to obtain a compound of formula I wherein R1 and R2 are hydrogen ; or g) condensing a compound of the formula VIIA see diagramm : EP0102929,P39,F6 with a compound of the formula VIIB see diagramm : EP0102929,P39,F6 wherein one of the groups Q and M represents a removable group, and the other represents a metal or halometal radical, and Ar, X, R1 to R3 and n are as defined above, if necesseray while temporarily protecting any interfering reactive group in all these processes, and isolating the resultant compound of formula ; and/or, if required, converting a resultant compound of formula I into another compound of formula I, and/or, if require, converting a resultant free compound into a salt or a resultant salt into the free compound or into another salt, and/or, if required, resolving a mixture of isomers or racemates obtained into the single isomers or racemates, and/or, if required, resolving a racemate obtained into the optical antipodes.
AU18746/83A
1982-09-07
1983-09-06
Propylamine derivatives
Ceased
AU566564B2
(en)
Applications Claiming Priority (2)
Application Number
Priority Date
Filing Date
Title
US41500082A
1982-09-07
1982-09-07
US415000
1982-09-07
Publications (2)
Publication Number
Publication Date
AU1874683A
true
AU1874683A
(en)
1984-03-15
AU566564B2
AU566564B2
(en)
1987-10-22
Family
ID=23643932
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
AU18746/83A
Ceased
AU566564B2
(en)
1982-09-07
1983-09-06
Propylamine derivatives
Country Status (18)
Country
Link
EP
(1)
EP0102929B1
(en)
JP
(1)
JPS5973546A
(en)
AT
(1)
ATE28069T1
(en)
AU
(1)
AU566564B2
(en)
CA
(1)
CA1242728A
(en)
DD
(1)
DD213208A5
(en)
DE
(1)
DE3372283D1
(en)
DK
(1)
DK405183A
(en)
ES
(4)
ES525400A0
(en)
FI
(1)
FI83632C
(en)
GR
(1)
GR78936B
(en)
HU
(1)
HU194157B
(en)
IE
(1)
IE55906B1
(en)
IL
(1)
IL69632A
(en)
NO
(1)
NO157975C
(en)
NZ
(1)
NZ205509A
(en)
PT
(1)
PT77291B
(en)
ZA
(1)
ZA836597B
(en)
Families Citing this family (1)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
JP2005500371A
(en)
*
2001-08-08
2005-01-06
ニューロサーチ、アクティーゼルスカブ
Substituted amine derivatives and methods of using them as monoamine neurotransmitter reuptake inhibitors
Family Cites Families (3)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
GB1237352A
(en)
*
1969-01-03
1971-06-30
Ct Europ De Rech S Mauvernay
Substituted propylamines
GB1343527A
(en)
*
1971-07-30
1974-01-10
Cerm Cent Europ Rech Mauvernay
Amino-propanol derivatives
FR2460919A1
(en)
*
1979-07-11
1981-01-30
Prod Synthese Ste Indle
AMINO-ETHERS OXIDES, PROCESS FOR PREPARING THEM AND THEIR THERAPEUTIC APPLICATION
1983
1983-09-01
AT
AT83810398T
patent/ATE28069T1/en
not_active
IP Right Cessation
1983-09-01
EP
EP83810398A
patent/EP0102929B1/en
not_active
Expired
1983-09-01
DE
DE8383810398T
patent/DE3372283D1/en
not_active
Expired
1983-09-02
IL
IL69632A
patent/IL69632A/en
unknown
1983-09-02
CA
CA000435963A
patent/CA1242728A/en
not_active
Expired
1983-09-05
FI
FI833150A
patent/FI83632C/en
not_active
IP Right Cessation
1983-09-05
DD
DD83254530A
patent/DD213208A5/en
not_active
IP Right Cessation
1983-09-06
GR
GR72391A
patent/GR78936B/el
unknown
1983-09-06
PT
PT77291A
patent/PT77291B/en
not_active
IP Right Cessation
1983-09-06
ES
ES525400A
patent/ES525400A0/en
active
Granted
1983-09-06
NZ
NZ205509A
patent/NZ205509A/en
unknown
1983-09-06
DK
DK405183A
patent/DK405183A/en
not_active
Application Discontinuation
1983-09-06
HU
HU833100A
patent/HU194157B/en
unknown
1983-09-06
NO
NO833178A
patent/NO157975C/en
unknown
1983-09-06
ZA
ZA836597A
patent/ZA836597B/en
unknown
1983-09-06
JP
JP58162720A
patent/JPS5973546A/en
active
Pending
1983-09-06
IE
IE2093/83A
patent/IE55906B1/en
not_active
IP Right Cessation
1983-09-06
AU
AU18746/83A
patent/AU566564B2/en
not_active
Ceased
1985
1985-03-14
ES
ES541260A
patent/ES8802010A1/en
not_active
Expired
1985-03-14
ES
ES541258A
patent/ES8606244A1/en
not_active
Expired
1985-03-14
ES
ES541259A
patent/ES8702335A1/en
not_active
Expired
Also Published As
Publication number
Publication date
FI833150A
(en)
1984-03-08
ES541258A0
(en)
1986-04-01
ATE28069T1
(en)
1987-07-15
IL69632A0
(en)
1983-12-30
CA1242728A
(en)
1988-10-04
ES8606244A1
(en)
1986-04-01
NZ205509A
(en)
1987-07-31
NO833178L
(en)
1984-03-08
ES8802010A1
(en)
1988-03-16
IE832093L
(en)
1984-03-07
ES541260A0
(en)
1988-03-16
DD213208A5
(en)
1984-09-05
AU566564B2
(en)
1987-10-22
ES541259A0
(en)
1986-12-16
ES8702335A1
(en)
1986-12-16
HU194157B
(en)
1988-01-28
DK405183D0
(en)
1983-09-06
FI83632C
(en)
1991-08-12
IE55906B1
(en)
1991-02-14
IL69632A
(en)
1987-08-31
EP0102929A3
(en)
1984-09-12
ZA836597B
(en)
1984-04-25
ES8506582A1
(en)
1985-08-01
DK405183A
(en)
1984-03-08
ES525400A0
(en)
1985-08-01
PT77291B
(en)
1986-07-14
FI833150A0
(en)
1983-09-05
NO157975C
(en)
1988-06-28
FI83632B
(en)
1991-04-30
DE3372283D1
(en)
1987-08-06
NO157975B
(en)
1988-03-14
GR78936B
(en)
1984-10-02
JPS5973546A
(en)
1984-04-25
EP0102929B1
(en)
1987-07-01
PT77291A
(en)
1983-10-01
EP0102929A2
(en)
1984-03-14
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