CA1078408A - 3-phenyl-sec-butylamine derivatives - Google Patents

3-phenyl-sec-butylamine derivatives

Info

Publication number: CA1078408A
Authority: CA; Canada
Prior art keywords: formula; lower alkyl; compound; alkyl group; pharmaceutically acceptable
Prior art date: 1975-02-21
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

CA245,616A

Other languages

English (en)

French (fr)

Inventor

Gosta L. Florvall

Svante B. Ross

Sven O. Ogren

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.)

Astra Lakemedel AB

Original Assignee

Astra Lakemedel AB

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.)

1975-02-21

Filing date

1976-02-12

Publication date

1980-05-27

1976-02-12 Application filed by Astra Lakemedel AB filed Critical Astra Lakemedel AB

1980-05-27 Application granted granted Critical

1980-05-27 Publication of CA1078408A publication Critical patent/CA1078408A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 47
125000000217 alkyl group Chemical group 0.000 claims abstract description 26
238000000034 method Methods 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 14
125000005843 halogen group Chemical group 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 16
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 12
239000003054 catalyst Substances 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
150000002576 ketones Chemical class 0.000 claims description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
-1 4-(3-aminobutyl)-3-chloro-N,N-dimethylaniline Chemical compound 0.000 claims description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
UZYFIMVXOSSVAZ-UHFFFAOYSA-N n-[4-[2-chloro-4-(dimethylamino)phenyl]but-3-en-2-ylidene]hydroxylamine Chemical compound CN(C)C1=CC=C(C=CC(C)=NO)C(Cl)=C1 UZYFIMVXOSSVAZ-UHFFFAOYSA-N 0.000 claims description 4
JTLBTBUQCKYSGG-UHFFFAOYSA-N n-[4-[4-(dimethylamino)-2-methylphenyl]but-3-en-2-ylidene]hydroxylamine Chemical compound CN(C)C1=CC=C(C=CC(C)=NO)C(C)=C1 JTLBTBUQCKYSGG-UHFFFAOYSA-N 0.000 claims description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 3
GOEJXBJDNCPMQQ-UHFFFAOYSA-N 4-[5-(dimethylamino)-2-methylphenyl]butan-2-one Chemical compound CN(C1=CC(=C(C=C1)C)CCC(C)=O)C GOEJXBJDNCPMQQ-UHFFFAOYSA-N 0.000 claims description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
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125000001475 halogen functional group Chemical group 0.000 claims 2
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239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
201000003631 narcolepsy Diseases 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
238000003918 potentiometric titration Methods 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
229940072690 valium Drugs 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Emergency Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (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)

CA245,616A 1975-02-21 1976-02-12 3-phenyl-sec-butylamine derivatives Expired CA1078408A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE7501956A SE396748B (sv)	1975-02-21	1975-02-21	Forfarande for framstellning av 3-fenyl-sek -butylaminderivat

Publications (1)

Publication Number	Publication Date
CA1078408A true CA1078408A (en)	1980-05-27

Family

ID=20323758

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA245,616A Expired CA1078408A (en)	1975-02-21	1976-02-12	3-phenyl-sec-butylamine derivatives

Country Status (12)

Country	Link
AT (1)	AT340384B (de)
AU (1)	AU499650B2 (de)
BE (1)	BE838739A (de)
CA (1)	CA1078408A (de)
CH (1)	CH609673A5 (de)
DE (1)	DE2606393A1 (de)
FR (1)	FR2301236A2 (de)
GB (1)	GB1536195A (de)
IE (1)	IE43129B1 (de)
LU (1)	LU74386A1 (de)
NL (1)	NL7601605A (de)
SE (1)	SE396748B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU701981B2 (en)	1995-12-21	1999-02-11	Sumitomo Chemical Company, Limited	Triazole derivatives and uses thereof

1975
- 1975-02-21 SE SE7501956A patent/SE396748B/xx unknown
1976
- 1976-02-06 AT AT82076A patent/AT340384B/de not_active IP Right Cessation
- 1976-02-12 CA CA245,616A patent/CA1078408A/en not_active Expired
- 1976-02-13 CH CH180076A patent/CH609673A5/xx not_active IP Right Cessation
- 1976-02-17 NL NL7601605A patent/NL7601605A/xx not_active Application Discontinuation
- 1976-02-18 DE DE19762606393 patent/DE2606393A1/de not_active Withdrawn
- 1976-02-19 AU AU11247/76A patent/AU499650B2/en not_active Expired
- 1976-02-20 LU LU74386A patent/LU74386A1/xx unknown
- 1976-02-20 IE IE341/76A patent/IE43129B1/en unknown
- 1976-02-20 FR FR7604707A patent/FR2301236A2/fr active Granted
- 1976-02-20 BE BE164457A patent/BE838739A/xx unknown
- 1976-02-20 GB GB6837/76A patent/GB1536195A/en not_active Expired

Also Published As

Publication number	Publication date
CH609673A5 (en)	1979-03-15
FR2301236A2 (fr)	1976-09-17
LU74386A1 (de)	1977-01-06
AT340384B (de)	1977-12-12
IE43129B1 (en)	1980-12-31
NL7601605A (nl)	1976-08-24
IE43129L (en)	1976-08-21
AU1124776A (en)	1977-08-25
FR2301236B2 (de)	1980-07-04
SE7501956L (sv)	1976-08-23
BE838739A (fr)	1976-08-20
AU499650B2 (en)	1979-04-26
ATA82076A (de)	1977-04-15
SE396748B (sv)	1977-10-03
DE2606393A1 (de)	1976-09-09
GB1536195A (en)	1978-12-20

Legal Events

Date	Code	Title	Description
1997-05-27	MKEX	Expiry

Publication	Publication Date	Title
EP0110372B1 (de)	1986-09-10	1-Phenylisochinolinderivate und Verfahren zu ihrer Herstellung, diese Verbindung enthaltende pharmazeutische Präparate und deren Anwendung
HUP0004334A2 (en)	2001-03-28	Substituted 1,2,3,4-tetrahydronaphthalene derivatives, process for producing them and pharmaceutical compositions containing them
US3574211A (en)	1971-04-06	1-(amino-monohalo-phenyl)-2-amino-alkanols and salts
JP3026948B2 (ja)	2000-03-27	アリールアクリルアミド誘導体
JPS5911571B2 (ja)	1984-03-16	オキソアルキル置換フェノ−ル類
SU1156593A3 (ru)	1985-05-15	Способ получени производных бензамида или их кислотно-аддитивных солей,или оптических изомеров
JPH0687798A (ja)	1994-03-29	新規なフェニルプロピニルアミン誘導体の製造法
US4140713A (en)	1979-02-20	Phenylethanolamine therapeutic agents
EP0226516B1 (de)	1992-07-29	Amidderivate und antiallergische Mittel, die sie enthalten
US6075018A (en)	2000-06-13	1-[2-(substituted vinyl)]-3,4-dihydro-4-dihydro-5H-2,3-benzodiazepine derivatives
US3821221A (en)	1974-06-28	1,2,3,6-tetrahydropyrimidine-2-one compounds and processes for makingthem
US3996381A (en)	1976-12-07	Amphetamine derivatives
US4000280A (en)	1976-12-28	Pharmaceutical compositions containing an amphetamine derivative for the alleviation of anxiety or treatment of depression
US3978064A (en)	1976-08-31	3-Aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters and intermediates leading thereto
FR2540870A1 (fr)	1984-08-17	Nouveaux derives de betaines n-iminopyridinium, leur preparation et leur application en tant que medicaments
US3972935A (en)	1976-08-03	Antiarrhythmic agents
US4000192A (en)	1976-12-28	Pharmacologically active compounds
US3213138A (en)	1965-10-19	N, n-disubstituted-n'-phenylalkyl hydrazines
IE43129B1 (en)	1980-12-31	3-phenyl-sec-butylamine derivatives
EP0142102B1 (de)	1987-09-23	Tertiäre Amine
EP0699680B1 (de)	2000-03-08	Oxazolochinolinonderivate, ihre Herstellung und ihre Verwendung als Arzneimittel
US5071849A (en)	1991-12-10	Dihydropyrimidothiazine derivatives
US4355045A (en)	1982-10-19	Anti-inflammatory 1-phenylethanolamine derivatives pharmaceutical compositions thereof and processes for their manufacture
EP0102213A1 (de)	1984-03-07	Ethanolaminderivate, sie enthaltende pharmazeutische Mittel sowie Verfahren zu ihrer Herstellung
US3959476A (en)	1976-05-25	Antihypertensive substituted triazoles