CH662810A5 - Ein benzamid-derivat, seine herstellung und verwendung. - Google Patents

Ein benzamid-derivat, seine herstellung und verwendung. Download PDF

Info

Publication number: CH662810A5
Authority: CH; Switzerland
Prior art keywords: hydroxy; formula; compound; benzamide; ethyl
Prior art date: 1984-01-20

Application number

CH598584A

Other languages

German (de)

English (en)

Inventor

Pal Dr Vago

Jozsef Dr Reiter

Frigyes Dr Goergenyi

Tamas Dr Fodor

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1984-01-20

Filing date

1984-12-17

Publication date

1987-10-30

1984-12-17 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1987-10-30 Publication of CH662810A5 publication Critical patent/CH662810A5/de

Links

KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title claims description 40
238000004519 manufacturing process Methods 0.000 title description 4
238000000034 method Methods 0.000 claims description 36
150000001875 compounds Chemical class 0.000 claims description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 16
239000003054 catalyst Substances 0.000 claims description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
BWHOZHOGCMHOBV-UHFFFAOYSA-N benzylideneacetone Chemical compound CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 claims description 8
238000002955 isolation Methods 0.000 claims description 8
238000011065 in-situ storage Methods 0.000 claims description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
229910052697 platinum Inorganic materials 0.000 claims description 2
239000002904 solvent Substances 0.000 claims 2
239000003849 aromatic solvent Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
-1 2- [N-benzyl-N- (1-methyl-3-phenyl-propyl) -amino] -acetyl Chemical group 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 3
125000000468 ketone group Chemical group 0.000 description 3
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
239000002262 Schiff base Substances 0.000 description 2
150000004753 Schiff bases Chemical class 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000003245 coal Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 2
VXWSXLSUWGZOHD-UHFFFAOYSA-N 5-(2-bromoacetyl)-2-hydroxybenzamide Chemical compound NC(=O)C1=CC(C(=O)CBr)=CC=C1O VXWSXLSUWGZOHD-UHFFFAOYSA-N 0.000 description 1
LWAQTCWTCCNHJR-UHFFFAOYSA-N 5-acetyl-2-hydroxybenzamide Chemical compound CC(=O)C1=CC=C(O)C(C(N)=O)=C1 LWAQTCWTCCNHJR-UHFFFAOYSA-N 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
229940054066 benzamide antipsychotics Drugs 0.000 description 1
150000003936 benzamides Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
ZASBYHZJHQFLGN-UHFFFAOYSA-N n-benzyl-4-phenylbutan-2-amine Chemical compound C=1C=CC=CC=1CNC(C)CCC1=CC=CC=C1 ZASBYHZJHQFLGN-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH598584A 1984-01-20 1984-12-17 Ein benzamid-derivat, seine herstellung und verwendung. CH662810A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU23484A HU190867B (en)	1984-01-20	1984-01-20	Process for preparing 2-hydroxy-5-/1-hydroxy-2-/1-methyl-3-phenyl-propyl/-amino/ethyl/-benzamide and pharmaceutically acceptable salts thereof

Publications (1)

Publication Number	Publication Date
CH662810A5 true CH662810A5 (de)	1987-10-30

Family

ID=10948617

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH598584A CH662810A5 (de)	1984-01-20	1984-12-17	Ein benzamid-derivat, seine herstellung und verwendung.

Country Status (18)

Country	Link
JP (1)	JPS60231639A (xx)
AT (1)	AT390612B (xx)
CA (1)	CA1239938A (xx)
CH (1)	CH662810A5 (xx)
CS (1)	CS249536B2 (xx)
DD (1)	DD228245A5 (xx)
DE (1)	DE3501582A1 (xx)
DK (1)	DK26185A (xx)
ES (1)	ES8608481A1 (xx)
FI (1)	FI83635C (xx)
FR (1)	FR2558465B1 (xx)
GB (1)	GB2152931B (xx)
HU (1)	HU190867B (xx)
NL (1)	NL8500119A (xx)
NO (1)	NO165918C (xx)
PT (1)	PT79844B (xx)
SE (1)	SE8500236L (xx)
SU (1)	SU1521281A3 (xx)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1247370A (en) *	1968-12-31	1971-09-22	Allen & Hanburys Ltd	Glyoxals and production thereof
ZA794872B (en) *	1978-09-20	1980-11-26	Schering Corp	A phenylalkylaminoethylsalicylamide,its preparation and pharmaceutical compositions containing it

1984
- 1984-01-20 HU HU23484A patent/HU190867B/hu not_active IP Right Cessation
- 1984-12-17 CH CH598584A patent/CH662810A5/de not_active IP Right Cessation
1985
- 1985-01-18 SU SU853837675A patent/SU1521281A3/ru active
- 1985-01-18 JP JP597885A patent/JPS60231639A/ja active Pending
- 1985-01-18 AT AT11685A patent/AT390612B/de not_active IP Right Cessation
- 1985-01-18 GB GB08501246A patent/GB2152931B/en not_active Expired
- 1985-01-18 PT PT7984485A patent/PT79844B/pt unknown
- 1985-01-18 FR FR8500702A patent/FR2558465B1/fr not_active Expired
- 1985-01-18 DE DE19853501582 patent/DE3501582A1/de not_active Withdrawn
- 1985-01-18 DD DD27264985A patent/DD228245A5/de not_active IP Right Cessation
- 1985-01-18 CA CA000472445A patent/CA1239938A/en not_active Expired
- 1985-01-18 FI FI850229A patent/FI83635C/fi not_active IP Right Cessation
- 1985-01-18 DK DK26185A patent/DK26185A/da not_active Application Discontinuation
- 1985-01-18 CS CS37785A patent/CS249536B2/cs unknown
- 1985-01-18 NO NO850225A patent/NO165918C/no unknown
- 1985-01-18 NL NL8500119A patent/NL8500119A/nl not_active Application Discontinuation
- 1985-01-18 ES ES540121A patent/ES8608481A1/es not_active Expired
- 1985-06-06 SE SE8500236A patent/SE8500236L/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
FR2558465A1 (fr)	1985-07-26
NL8500119A (nl)	1985-08-16
FI83635B (fi)	1991-04-30
FR2558465B1 (fr)	1988-08-26
GB2152931B (en)	1987-03-18
NO165918C (no)	1991-05-02
NO165918B (no)	1991-01-21
FI850229A0 (fi)	1985-01-18
AT390612B (de)	1990-06-11
ES540121A0 (es)	1986-07-16
GB8501246D0 (en)	1985-02-20
GB2152931A (en)	1985-08-14
DD228245A5 (de)	1985-10-09
PT79844B (en)	1986-10-23
DK26185A (da)	1985-07-21
ATA11685A (de)	1989-11-15
PT79844A (en)	1985-02-01
SE8500236L (sv)	1985-07-21
JPS60231639A (ja)	1985-11-18
HUT36779A (en)	1985-10-28
SE8500236D0 (sv)	1985-01-18
CS249536B2 (en)	1987-03-12
NO850225L (no)	1985-07-22
FI850229L (fi)	1985-07-21
SU1521281A3 (ru)	1989-11-07
DK26185D0 (da)	1985-01-18
HU190867B (en)	1986-11-28
CA1239938A (en)	1988-08-02
ES8608481A1 (es)	1986-07-16
DE3501582A1 (de)	1985-08-01
FI83635C (fi)	1991-08-12

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DE69109514T2 (de)	1995-12-21	4-(4-Alkoxyphenyl)-2-Butylaminderivate und deren Herstellungsverfahren.
DE2100323C3 (de)	1979-02-22	Ureido-phenoxy-2-hydroxy-3-alkylaminopropane
CH637933A5 (de)	1983-08-31	Verfahren zur herstellung neuer derivate von perhydro-aza-heterocyclen.
DE2413102A1 (de)	1975-10-09	Verfahren zur herstellung von 1-(3,5dihydroxyphenyl)-1-hydroxy-2- eckige klammer auf 1-methyl-2-(4-hydroxyphenyl)-aethyl eckige klammer zu -amino-aethan
DD228249A5 (de)	1985-10-09	Verfahren zur herstellung von substituierten imidazolen
EP0000395A1 (de)	1979-01-24	2-Piperazinotetraline, ihre Herstellung und Verwendung als Arzneimittel
DE1294961B (de)	1969-08-21	Verfahren zur Herstellung von 22-Azacholestanderivaten und deren Saeureadditionssalzen
AT390612B (de)	1990-06-11	Verfahren zur herstellung eines benzamid-derivates und von dessen pharmazeutisch geeigneten saeureadditionssalzen
DE60032453T2 (de)	2007-10-04	Ein verfahren zur synthese von ritonavir
DE1695962A1 (de)	1971-05-19	(2-Aminocycloalkyl)hydrochinone und Derivate derselben sowie Verfahren zu ihrer Herstellung
DE2417464A1 (de)	1975-01-16	Neue amine und verfahren zu ihrer herstellung
AT256816B (de)	1967-09-11	Verfahren zur Herstellung von neuen substituierten 1-Phenyl-2-aminoalkanolen und deren Säureadditionssalzen
DE2532268A1 (de)	1976-02-05	Neue n tief beta -substituierte 8-beta-aminoaethylergolin-i-derivate und deren salze, ihr herstellungsverfahren sowie ihre verwendung
DE2126169C3 (de)	1981-03-19	Alkanolaminderivate und sie enthaltende pharmazeutische Zusammensetzungen
AT360992B (de)	1981-02-10	Verfahren zur herstellung neuer phenylazacyclo- alkane und von deren salzen und optisch aktiven verbindungen
AT347473B (de)	1978-12-27	Verfahren zur herstellung von neuen morpholinverbindungen und deren nicht-toxischen salzen
DE2312234A1 (de)	1974-09-19	Verfahren zur herstellung des n,n'bis-eckige klammer auf 2-(3,4-dihydroxyphenyl)-2-hydroxyaethyl eckige klammer zu -hexamethylendiamins und seiner saeureadditionssalze
EP0056082A1 (de)	1982-07-21	Verfahren zur Herstellung von 4-Amino-buttersäureamid-Hydrochlorid
EP0180890A2 (de)	1986-05-14	Verfahren zur diastereoselektiven Reduktion von 3-Amino-1-benzoxepin-5(2H)-onen
AT238180B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
DE2414772C3 (de)	1979-08-30	H33-Diphenylpropyl)-2-methyl-3phenylaziridin und Verfahren zu seiner Herstellung
DE1595903C (de)	1972-10-05	1-Substituierte 2,6-Dimethyl-4-phenylpiperazine
AT337155B (de)	1977-06-10	Verfahren zur herstellung von neuen n-cycloalkylbenzylaminen und deren physiologisch vertraglichen saureadditionssalzen
DE2612506A1 (de)	1976-10-14	4-hydroxy-alpha- eckige klammer auf (3,4-methylendioxyphenyl)-isopropylaminomethyl eckige klammer zu -3-(methylsulfonylmethyl)-benzylalkohol
AT226231B (de)	1963-03-11	Verfahren zur Herstellung der stereoisomeren Formen des neuen, razemischen 2-Phenyl-2-piperidyl-(2)-äthanols

Legal Events

Date	Code	Title	Description
1992-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased