DE2704744C2 - Fettsäureamide von α-Methyl-m-(trifluormethyl)-phenäthylamin, Verfahren zu ihrer Herstellung und Arzneimittel - Google Patents

Fettsäureamide von α-Methyl-m-(trifluormethyl)-phenäthylamin, Verfahren zu ihrer Herstellung und Arzneimittel

Info

Publication number: DE2704744C2
Authority: DE; Germany
Prior art keywords: cholesterol; norfenfluramine; amides; fatty acid; liver
Prior art date: 1976-02-04
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

DE2704744A

Other languages

German (de)

English (en)

Other versions

DE2704744A1 (de

Inventor

Albert Duncan Mechanicsville Va. Cale jun.

Carl Dalton Richmond Va. Lunsford

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.)

AH Robins Co Inc

Original Assignee

AH Robins Co Inc

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.)

1976-02-04

Filing date

1977-02-04

Publication date

1986-07-03

1976-12-16 Priority claimed from US05/751,294 external-priority patent/US4115587A/en

1977-02-04 Application filed by AH Robins Co Inc filed Critical AH Robins Co Inc

1977-08-11 Publication of DE2704744A1 publication Critical patent/DE2704744A1/de

1986-07-03 Application granted granted Critical

1986-07-03 Publication of DE2704744C2 publication Critical patent/DE2704744C2/de

Status Expired legal-status Critical Current

Links

MLBHFBKZUPLWBD-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]-2-propanamine Chemical compound CC(N)CC1=CC=CC(C(F)(F)F)=C1 MLBHFBKZUPLWBD-UHFFFAOYSA-N 0.000 title claims description 36
235000014113 dietary fatty acids Nutrition 0.000 title claims description 29
239000000194 fatty acid Substances 0.000 title claims description 29
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150000004665 fatty acids Chemical class 0.000 title claims description 26
238000000034 method Methods 0.000 title description 16
239000003814 drug Substances 0.000 title description 15
238000002360 preparation method Methods 0.000 title description 8
230000008569 process Effects 0.000 title description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 71
235000012000 cholesterol Nutrition 0.000 description 35
150000001408 amides Chemical class 0.000 description 34
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
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SFIHQZFZMWZOJV-HZJYTTRNSA-N linoleamide Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(N)=O SFIHQZFZMWZOJV-HZJYTTRNSA-N 0.000 description 10
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LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
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FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
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PIDLOFBRTWNFAR-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]propan-2-amine;hydrochloride Chemical compound Cl.CC(N)CC1=CC=CC(C(F)(F)F)=C1 PIDLOFBRTWNFAR-UHFFFAOYSA-N 0.000 description 3
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 3
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BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 2
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HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
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102000004169 proteins and genes Human genes 0.000 description 1
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CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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239000002600 sunflower oil Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
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DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
229940042585 tocopherol acetate Drugs 0.000 description 1
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230000001988 toxicity Effects 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
235000019168 vitamin K Nutrition 0.000 description 1
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239000011652 vitamin K3 Substances 0.000 description 1
229940011671 vitamin b6 Drugs 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Hematology (AREA)
Diabetes (AREA)
Obesity (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Child & Adolescent Psychology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DE2704744A 1976-02-04 1977-02-04 Fettsäureamide von α-Methyl-m-(trifluormethyl)-phenäthylamin, Verfahren zu ihrer Herstellung und Arzneimittel Expired DE2704744C2 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US65519576A	1976-02-04	1976-02-04
US05/751,294 US4115587A (en)	1976-02-04	1976-12-16	Fatty acid amides of norfenfluramine and compositions and methods thereof

Publications (2)

Publication Number	Publication Date
DE2704744A1 DE2704744A1 (de)	1977-08-11
DE2704744C2 true DE2704744C2 (de)	1986-07-03

Family

ID=27096923

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE2704744A Expired DE2704744C2 (de)	1976-02-04	1977-02-04	Fettsäureamide von α-Methyl-m-(trifluormethyl)-phenäthylamin, Verfahren zu ihrer Herstellung und Arzneimittel

Country Status (6)

Country	Link
JP (1)	JPS5297920A (fr)
AU (1)	AU510935B2 (fr)
CA (1)	CA1080254A (fr)
DE (1)	DE2704744C2 (fr)
FR (1)	FR2340089A1 (fr)
GB (1)	GB1550543A (fr)

1977
- 1977-01-21 GB GB2535/77A patent/GB1550543A/en not_active Expired
- 1977-01-26 CA CA270,500A patent/CA1080254A/fr not_active Expired
- 1977-02-03 FR FR7703055A patent/FR2340089A1/fr active Granted
- 1977-02-04 DE DE2704744A patent/DE2704744C2/de not_active Expired
- 1977-02-04 JP JP1152777A patent/JPS5297920A/ja active Granted
- 1977-02-04 AU AU21951/77A patent/AU510935B2/en not_active Expired

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NICHTS-ERMITTELT

Also Published As

Publication number	Publication date
AU510935B2 (en)	1980-07-24
GB1550543A (en)	1979-08-15
CA1080254A (fr)	1980-06-24
JPS6129941B2 (fr)	1986-07-10
FR2340089B1 (fr)	1980-04-18
FR2340089A1 (fr)	1977-09-02
DE2704744A1 (de)	1977-08-11
AU2195177A (en)	1978-08-10
JPS5297920A (en)	1977-08-17

Publication	Publication Date	Title
DE3204596C2 (fr)	1991-07-04
DE2432799C2 (de)	1986-01-02	7-substituierte 5-Methyl-isoflavone, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Metabolica
DE69431965T2 (de)	2003-04-30	Wirkstoff gegen fettsucht
DE3037770C2 (de)	1994-11-10	N-Niedrigalkyl-3-phenoxy-1-azetidincarboxamide und diese Verbindungen enthaltende Zubereitungen
DE2160148C2 (de)	1984-07-19	Arzneimittel und bestimmte Sulfoxide als solche
AT391313B (de)	1990-09-25	Verfahren zur herstellung von neuen substituierten n-aryl-harnstoffen
CH637623A5 (de)	1983-08-15	Verfahren zur herstellung von aralkylanilinen.
EP0004680A2 (fr)	1979-10-17	Derivé de l'acide nonatétraénoique et compositions pharmaceutiques
DE2625012C3 (de)	1980-04-10	Arzneimittel zur Kontrolle von Leberkrankheiten
DE1815808A1 (de)	1970-02-26	Benzolderivate
DE2157272C3 (de)	1979-03-01	Verwendung von bis-(p-Chlorphenoxy)acetylharnstoff
DE1493083C (fr)	1973-03-22
DE69023045T2 (de)	1996-04-11	Carboxamidderivate.
DE2704744C2 (de)	1986-07-03	Fettsäureamide von &alpha;-Methyl-m-(trifluormethyl)-phenäthylamin, Verfahren zu ihrer Herstellung und Arzneimittel
CH631446A5 (de)	1982-08-13	Verfahren zur herstellung von neuen n-(benzoylmercaptoacyl)-histidinen und n-(mercaptoacyl)-histidinen.
DE1493083B1 (de)	1972-08-17	Linolsaeureamide und Verfahren zu ihrer Herstellung
DE1957769C3 (de)	1980-08-28	4,6-Diamino-l,2-dihydro-2,2-dimethyl-133-triazin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate
DE2038836C3 (de)	1979-12-06	Arzneimittel
DE3025656C2 (fr)	1989-06-22
DE1493618A1 (de)	1969-07-10	Cumarinderivate und ein Verfahren zu ihrer Herstellung
DE2527628B2 (de)	1977-08-11	N-vinyloxyaethyl-alpha-methyl-beta- phenaethylamine und appetitzuegler auf deren basis
DE2515142B2 (de)	1976-11-11	Oral verabfolgbare mittel zur senkung des lipid- und cholesterin- spiegels
DE1618959C3 (de)	1978-12-14	Fettsäureamide und Verfahren zu ihrer Herstellung
DE2406812A1 (de)	1974-08-22	2-(3,5-di-tert-butylphenyl)-(thio- oder sulfonyl-)- alkancarbonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
DE2609574B2 (de)	1977-10-27	1-(4-fluor-3-trifluormethylthio- phenyl)-piperazin, dessen salze, verfahren zu dessen herstellung und arzneimittel

Legal Events

Date	Code	Title	Description
1984-01-12	8128	New person/name/address of the agent	Representative=s name: KOHLER, M., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 80
1984-02-02	8110	Request for examination paragraph 44
1986-02-13	8128	New person/name/address of the agent	Representative=s name: GLAESER, J., DIPL.-ING., 2000 HAMBURG HILTL, E., D
1986-07-03	D2	Grant after examination
1987-01-08	8364	No opposition during term of opposition
1989-02-16	8339	Ceased/non-payment of the annual fee

DE2704744C2 - Fettsäureamide von &alpha;-Methyl-m-(trifluormethyl)-phenäthylamin, Verfahren zu ihrer Herstellung und Arzneimittel - Google Patents