CA1050543A - Acylamino-2 benzylamines - Google Patents

Acylamino-2 benzylamines

Info

Publication number: CA1050543A
Authority: CA; Canada
Prior art keywords: effected; methyl; formula; morpholino; group
Prior art date: 1973-06-07
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.): Expired

Application number

CA201,832A

Other languages

English (en)

Other versions

CA201832S (en

Inventor

Gerd Kruger

Johannes Keck

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.)

Boehringer Ingelheim Pharma GmbH and Co KG

Original Assignee

Dr Karl Thomae GmbH

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.)

1973-06-07

Filing date

1974-06-06

Publication date

1979-03-13

1974-06-06 Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH

1979-03-13 Application granted granted Critical

1979-03-13 Publication of CA1050543A publication Critical patent/CA1050543A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 23
238000002360 preparation method Methods 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 14
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
230000029936 alkylation Effects 0.000 claims description 6
238000005804 alkylation reaction Methods 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
-1 isopropylamino Chemical group 0.000 claims description 6
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 5
235000019253 formic acid Nutrition 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
KIQKWAUQWIPLSX-UHFFFAOYSA-N N-[3-chloro-2-[[methyl-(2-morpholin-2-yl-2-oxoethyl)amino]methyl]phenyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=C(CN(CC(=O)C2CNCCO2)C)C(=CC=C1)Cl KIQKWAUQWIPLSX-UHFFFAOYSA-N 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
229910052740 iodine Chemical group 0.000 claims description 2
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 claims description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
230000011987 methylation Effects 0.000 claims 4
238000007069 methylation reaction Methods 0.000 claims 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
150000007529 inorganic bases Chemical class 0.000 claims 1
230000001035 methylating effect Effects 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
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 1
230000029058 respiratory gaseous exchange Effects 0.000 abstract description 2
238000007126 N-alkylation reaction Methods 0.000 abstract 1
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 1
230000000144 pharmacologic effect Effects 0.000 abstract 1
230000004936 stimulating effect Effects 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
LGACUMPRRMLUFZ-UHFFFAOYSA-N 1,4-dihydroquinazoline Chemical class C1=CC=C2CN=CNC2=C1 LGACUMPRRMLUFZ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
RDPOPKLGKWSBBA-UHFFFAOYSA-N N-[3-chloro-2-[[(2-morpholin-2-yl-2-oxoethyl)-propan-2-ylamino]methyl]phenyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=C(CN(CC(=O)C2CNCCO2)C(C)C)C(=CC=C1)Cl RDPOPKLGKWSBBA-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002332 glycine derivatives Chemical class 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

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
- C07D295/16—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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Enzymes And Modification Thereof (AREA)

CA201,832A 1973-06-07 1974-06-06 Acylamino-2 benzylamines Expired CA1050543A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2328972A DE2328972A1 (de)	1973-06-07	1973-06-07	Neues verfahren zur herstellung von 2-acylamino-benzylaminen

Publications (1)

Publication Number	Publication Date
CA1050543A true CA1050543A (fr)	1979-03-13

Family

ID=5883287

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA201,832A Expired CA1050543A (fr)	1973-06-07	1974-06-06	Acylamino-2 benzylamines

Country Status (14)

Country	Link
JP (1)	JPS5735706B2 (fr)
AT (1)	AT333294B (fr)
BG (1)	BG21853A3 (fr)
CA (1)	CA1050543A (fr)
CH (1)	CH599127A5 (fr)
DE (1)	DE2328972A1 (fr)
DK (1)	DK300774A (fr)
ES (1)	ES426120A1 (fr)
FI (1)	FI144074A7 (fr)
HU (1)	HU167682B (fr)
NL (1)	NL7407063A (fr)
PL (1)	PL89956B1 (fr)
SE (1)	SE409857B (fr)
YU (2)	YU36369B (fr)

1973
- 1973-06-07 DE DE2328972A patent/DE2328972A1/de active Pending
1974
- 1974-04-29 AT AT350974A patent/AT333294B/de not_active IP Right Cessation
- 1974-05-09 ES ES426120A patent/ES426120A1/es not_active Expired
- 1974-05-10 FI FI1440/74A patent/FI144074A7/fi unknown
- 1974-05-22 YU YU01424/74A patent/YU36369B/xx unknown
- 1974-05-27 NL NL7407063A patent/NL7407063A/xx not_active Application Discontinuation
- 1974-05-28 BG BG026806A patent/BG21853A3/xx unknown
- 1974-06-04 DK DK300774A patent/DK300774A/da not_active Application Discontinuation
- 1974-06-05 HU HUTO963A patent/HU167682B/hu unknown
- 1974-06-06 CA CA201,832A patent/CA1050543A/fr not_active Expired
- 1974-06-06 SE SE7407487A patent/SE409857B/xx unknown
- 1974-06-06 PL PL1974171701A patent/PL89956B1/pl unknown
- 1974-06-06 JP JP6451674A patent/JPS5735706B2/ja not_active Expired
- 1974-06-07 CH CH785174A patent/CH599127A5/xx not_active IP Right Cessation
1981
- 1981-03-10 YU YU00613/81A patent/YU61381A/xx unknown

Also Published As

Publication number	Publication date
YU142474A (en)	1981-11-13
JPS5032141A (fr)	1975-03-28
JPS5735706B2 (fr)	1982-07-30
DK300774A (fr)	1975-02-03
PL89956B1 (fr)	1976-12-31
YU61381A (en)	1983-09-30
YU36369B (en)	1983-06-30
SE7407487L (fr)	1974-12-09
ATA350974A (de)	1976-03-15
AT333294B (de)	1976-11-10
NL7407063A (fr)	1974-12-10
HU167682B (fr)	1975-11-28
SE409857B (sv)	1979-09-10
CH599127A5 (fr)	1978-05-12
DE2328972A1 (de)	1975-01-02
BG21853A3 (bg)	1976-09-20
ES426120A1 (es)	1976-07-01
FI144074A7 (fr)	1974-12-08

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DE69516847T2 (de)	2000-10-26	Chlorpyrimidine als zwischenprodukte
CA1109871A (fr)	1981-09-29	Derives de la purine
US4767859A (en)	1988-08-30	Process for the preparation of pteridine derivatives
CA1263652A (fr)	1989-12-05	Derives de substitution de benzylphtalazinone
CA1120471A (fr)	1982-03-23	Obtention de 2-adamantylhydrazines et de substances pharmaceutiques qui en contiennent
DE2849537A1 (de)	1980-05-22	Substituierte 5-(2-imidazolin-2-yl)- aminopyrimidine und verfahren zu deren herstellung
NZ201553A (en)	1985-08-16	Substituted aminopyridazines and pharmaceutical compositions
PL108034B1 (pl)	1980-03-31	Sposob wytwarzania nowych pochodnych tiazolo/3,4-bmethod of producing new derivatives of thiazolo/3,4-b/isoquinoline /izochinoliny
SU680644A3 (ru)	1979-08-15	Способ получени 2-бром-6-фтор -2-имидазолидинилиденбензамина или его солей
CA1050543A (fr)	1979-03-13	Acylamino-2 benzylamines
DE3027106C2 (fr)	1988-11-10
US4507478A (en)	1985-03-26	2-Mercaptopyrimidohexahydroquinolines and related compounds
CH631448A5 (de)	1982-08-13	Verfahren zur herstellung neuer piperazinderivate.
US2415786A (en)	1947-02-11	Unsymmetrically substituted piperazines
IL44122A (en)	1977-05-31	2-(1-piperazinyl)-thiazole derivatives their preparation and pharmaceutical compositions containing them
CH643821A5 (de)	1984-06-29	Substituierte phenylacetylguanidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate.
CA1119170A (fr)	1982-03-02	Obtention de 2-adamantylhydrazines et de substances pharmaceutiques qui en contiennent
EP0041757A1 (fr)	1981-12-16	Dérivés d'éthylène-diamine, leur préparation, compositions pharmaceutiques les contenant et produits intermédiaires pour leur préparation
US3135756A (en)	1964-06-02	Table ii
US2528940A (en)	1950-11-07	Pyrrolidylethyl indole compounds
US4221798A (en)	1980-09-09	Hypotensive 2-heterocycloamino-imidazolines
US3029239A (en)	1962-04-10	Basic substituted 1-and 7-alkylxanthines or salts thereof
JPS6141915B2 (fr)	1986-09-18
JPH0625191B2 (ja)	1994-04-06	１−［２−（フエニルメチル）フエニルピペラジン化合物、その製造方法および医薬組成物
CA1050023A (fr)	1979-03-06	Synthese de benzylamines