UA7589A1 - METHOD OF OBTAINING (1-ARYLCYCLOBUTYL) -ALKYLAMINES OR THEIR PHARMACOLOGICALLY IMPROVED SALTS - Google Patents

METHOD OF OBTAINING (1-ARYLCYCLOBUTYL) -ALKYLAMINES OR THEIR PHARMACOLOGICALLY IMPROVED SALTS

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Publication number
UA7589A1
UA7589A1 UA3834158A UA3834158A UA7589A1 UA 7589 A1 UA7589 A1 UA 7589A1 UA 3834158 A UA3834158 A UA 3834158A UA 3834158 A UA3834158 A UA 3834158A UA 7589 A1 UA7589 A1 UA 7589A1
Authority
UA
Ukraine
Prior art keywords
chloro
phenyl
arylcyclobutyl
alkylamines
nmgbr
Prior art date
Application number
UA3834158A
Other languages
Russian (ru)
Ukrainian (uk)
Inventor
Едвард Джеффрі Джеймс
Козлик Антонін
Чарльз Вілмшерст Ерік
Original Assignee
"Дзе Бутс Компані Плс"
"Дзе Бутс Компани ПЛС"
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Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26279045&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=UA7589(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by "Дзе Бутс Компані Плс", "Дзе Бутс Компани ПЛС" filed Critical "Дзе Бутс Компані Плс"
Publication of UA7589A1 publication Critical patent/UA7589A1/en

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    • 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
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/50—Halogenated unsaturated alcohols containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
    • C07C49/237—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/567—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16—Unsaturated compounds
    • C07C61/40—Unsaturated compounds containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D295/06—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 halogen atoms or nitro radicals
    • C07D295/073—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 halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Psychiatry (AREA)
  • Neurology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Изобретение касается замещенных аминов, в частности (1-арилциклобутил)-алкиламинов общей формулы: или 1; а) n=0; R1 – C1-С4-алкил; C3-циклоалкил или фенил; б) n=1; R1 - Н; R5 и R6 вместе с фенилом образуют 4-хлорфенил; 3-хлор-5-метилфенил; 3,4-дихлорфенил; 4-хлор-3-трифторметилфенил; 4-метоксифенил; 4-бромфенил; 3-хлор-4-метил-фенил; 2-нафтил; 4-фторфенил или 4-бифенилил; R7 – С1-С2-алкил, или их фармакологически приемлемых солей, обладающих антидепрессивной активностью, что может быть использовано в медицине. Цель - создание новых активных веществ указанного класса без побочных действий. Синтез ведут обработкой соответствующего карбонитрила реактивом Гриньяра: R1MgBr или R7MgBr, где R1 и R7 - см. выше, в среде эфира (толуола) при температуре до кипения. Полученный продукт, содержащий группу CR1-NMgBr или CHR1-CR7-NMgBr, с R1 и R7, указанными выше, подвергают восстановлению с помощью боргидрида натрия в среде этанола, метанола или диэтиленгликольдиметилового эфира. Выделение целевого продукта ведут в свободном виде или в виде фармакологически приемлемой соли. Новые вещества обладают антидепрессивной активностью при дозе ED50=30мг/кг без признаков тираминазного ингибирования, наблюдающегося с известным 1-фенил-2-аминоциклопропаном.The invention relates to substituted amines, in particular (1-arylcyclobutyl) -alkylamines of the general formula: or 1; a) n = 0; R1 is C1 -C4 alkyl; C3 cycloalkyl or phenyl; b) n = 1; R1 is H; R5 and R6 together with phenyl form 4-chlorophenyl; 3-chloro-5-methylphenyl; 3,4-dichlorophenyl; 4-chloro-3-trifluoromethylphenyl; 4-methoxyphenyl; 4-bromophenyl; 3-chloro-4-methylphenyl; 2-naphthyl; 4-fluorophenyl or 4-biphenylyl; R7 - C1-C2-alkyl, or their pharmacologically acceptable salts with antidepressant activity, which can be used in medicine. The goal is to create new active substances of the specified class without side effects. The synthesis is carried out by treating the corresponding carbonitrile with a Grignard reagent: R1MgBr or R7MgBr, where R1 and R7 - see above, in an ether (toluene) medium at a temperature to boiling. The resulting product containing the CR1-NMgBr or CHR1-CR7-NMgBr group with R1 and R7 as indicated above is subjected to reduction with sodium borohydride in ethanol, methanol or diethylene glycol dimethyl ether. Isolation of the target product is carried out in free form or in the form of a pharmacologically acceptable salt. The new substances have antidepressant activity at a dose of ED50 = 30mg / kg without signs of tyraminase inhibition observed with the known 1-phenyl-2-aminocyclopropane.

UA3834158A 1981-04-06 1982-04-05 METHOD OF OBTAINING (1-ARYLCYCLOBUTYL) -ALKYLAMINES OR THEIR PHARMACOLOGICALLY IMPROVED SALTS UA7589A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8110710 1981-04-06
GB8110709 1981-04-06

Publications (1)

Publication Number Publication Date
UA7589A1 true UA7589A1 (en) 1995-09-29

Family

ID=26279045

Family Applications (2)

Application Number Title Priority Date Filing Date
UA3834158A UA7589A1 (en) 1981-04-06 1982-04-05 METHOD OF OBTAINING (1-ARYLCYCLOBUTYL) -ALKYLAMINES OR THEIR PHARMACOLOGICALLY IMPROVED SALTS
UA3426748A UA7838A1 (en) 1981-04-06 1982-04-05 METHOD OF OBTAINING SUBSTITUTED 1- (1-PHENYLYCYCLOBUTYL) -ALKYLAMINES OR THEIR PHARMACOLOGICALLY IMPROVED SALTS

Family Applications After (1)

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UA3426748A UA7838A1 (en) 1981-04-06 1982-04-05 METHOD OF OBTAINING SUBSTITUTED 1- (1-PHENYLYCYCLOBUTYL) -ALKYLAMINES OR THEIR PHARMACOLOGICALLY IMPROVED SALTS

Country Status (40)

Country Link
KR (1) KR900000274B1 (en)
AT (1) AT382612B (en)
AU (1) AU545595B2 (en)
BG (2) BG40652A3 (en)
CA (1) CA1248955A (en)
CH (1) CH652117A5 (en)
CS (1) CS244672B2 (en)
CY (1) CY1408A (en)
DD (1) DD208348A5 (en)
DE (1) DE3212682A1 (en)
DK (1) DK161770C (en)
ES (5) ES511152A0 (en)
FI (1) FI77223C (en)
FR (1) FR2504920B1 (en)
GB (1) GB2098602B (en)
GE (1) GEP19970661B (en)
GR (1) GR76697B (en)
HK (1) HK13888A (en)
HU (1) HU186582B (en)
IE (1) IE52768B1 (en)
IL (1) IL65257A0 (en)
IN (1) IN155773B (en)
IT (1) IT1235758B (en)
JO (1) JO1184B1 (en)
KE (1) KE3753A (en)
LU (1) LU84070A1 (en)
MY (1) MY8800048A (en)
NL (1) NL192201C (en)
NO (1) NO156785C (en)
NZ (1) NZ200178A (en)
PH (1) PH22762A (en)
PL (2) PL139120B1 (en)
PT (1) PT74580B (en)
RO (2) RO89436A2 (en)
SE (1) SE452611B (en)
SG (1) SG67287G (en)
SU (2) SU1482522A3 (en)
UA (2) UA7589A1 (en)
YU (2) YU44336B (en)
ZW (1) ZW4982A1 (en)

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Also Published As

Publication number Publication date
NO821087L (en) 1982-10-07
KR900000274B1 (en) 1990-01-24
YU6385A (en) 1985-08-31
IT8248157A0 (en) 1982-04-02
NL192201B (en) 1996-11-01
LU84070A1 (en) 1983-06-07
PL139120B1 (en) 1986-12-31
RO89436A2 (en) 1986-06-30
ZW4982A1 (en) 1982-11-03
IT1235758B (en) 1992-09-28
YU44336B (en) 1990-06-30
BG40651A3 (en) 1986-01-15
UA7838A1 (en) 1995-12-26
ATA132582A (en) 1986-08-15
ES519032A0 (en) 1984-03-01
DK161770B (en) 1991-08-12
KR830010065A (en) 1983-12-26
JO1184B1 (en) 1983-11-30
DE3212682A1 (en) 1982-10-21
YU44253B (en) 1990-04-30
ES8406414A1 (en) 1984-08-01
GEP19970661B (en) 1997-01-04
ES519031A0 (en) 1984-08-16
IL65257A0 (en) 1983-12-30
ES8305678A1 (en) 1983-04-16
DK161770C (en) 1992-02-10
HU186582B (en) 1985-08-28
FI821197L (en) 1982-10-07
KE3753A (en) 1987-10-02
AT382612B (en) 1987-03-25
FI821197A0 (en) 1982-04-05
RO84802A (en) 1984-09-29
NL8201347A (en) 1982-11-01
ES511152A0 (en) 1983-04-16
IE52768B1 (en) 1988-02-17
GB2098602A (en) 1982-11-24
SU1461372A3 (en) 1989-02-23
DD208348A5 (en) 1984-05-02
GR76697B (en) 1984-08-28
BG40652A3 (en) 1986-01-15
IE820481L (en) 1982-10-06
YU75082A (en) 1985-08-31
SE8202166L (en) 1982-11-25
PT74580B (en) 1983-12-23
SU1482522A3 (en) 1989-05-23
PT74580A (en) 1982-04-01
CY1408A (en) 1988-04-22
SE452611B (en) 1987-12-07
DE3212682C2 (en) 1992-03-26
GB2098602B (en) 1984-08-22
FI77223C (en) 1989-02-10
FR2504920A1 (en) 1982-11-05
AU8221382A (en) 1982-10-14
NZ200178A (en) 1985-07-31
CA1248955A (en) 1989-01-17
HK13888A (en) 1988-02-26
ES8403097A1 (en) 1984-03-01
CH652117A5 (en) 1985-10-31
PL136242B1 (en) 1986-02-28
AU545595B2 (en) 1985-07-18
CS245782A2 (en) 1985-08-15
FR2504920B1 (en) 1985-06-28
IN155773B (en) 1985-03-09
PL235832A1 (en) 1983-09-12
PL240079A1 (en) 1983-09-12
MY8800048A (en) 1988-12-31
NL192201C (en) 1997-03-04
DK146482A (en) 1982-10-07
ES519029A0 (en) 1984-08-01
ES8406413A1 (en) 1984-08-01
ES519030A0 (en) 1984-08-01
CS244672B2 (en) 1986-08-14
ES8407002A1 (en) 1984-08-16
NO156785B (en) 1987-08-17
SG67287G (en) 1988-02-19
RO84802B (en) 1984-10-30
FI77223B (en) 1988-10-31
NO156785C (en) 1987-11-25
PH22762A (en) 1988-12-12

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