SU474145A3 - Способ получени производных имидазолина - Google Patents

Способ получени производных имидазолина

Info

Publication number: SU474145A3
Authority: SU; USSR - Soviet Union
Prior art keywords: furan; salt; methyl; alkyl; solution
Prior art date: 1971-01-27

Application number

SU1742351A

Other languages

English (en)

Russian (ru)

Inventor

Бинон Фернан

Аресшка Алекс

Original Assignee

Лабаз С.А. (Фирма)

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.)

1971-01-27

Filing date

1972-01-27

Publication date

1975-06-14

1972-01-27 Application filed by Лабаз С.А. (Фирма) filed Critical Лабаз С.А. (Фирма)

1975-06-14 Application granted granted Critical

1975-06-14 Publication of SU474145A3 publication Critical patent/SU474145A3/ru

Links

238000000034 method Methods 0.000 title claims description 6
150000002462 imidazolines Chemical class 0.000 title 1
229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 title 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
241001415513 Salpida Species 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 12
239000000243 solution Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
150000001875 compounds Chemical class 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
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 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000012458 free base Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-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 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
TVMUHOAONWHJBV-UHFFFAOYSA-M dehydroglycinate Chemical compound [O-]C(=O)C=N TVMUHOAONWHJBV-UHFFFAOYSA-M 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 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
239000005457 ice water Substances 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU1742351A 1971-01-27 1972-01-27 Способ получени производных имидазолина SU474145A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB332771		1971-01-27

Publications (1)

Publication Number	Publication Date
SU474145A3 true SU474145A3 (ru)	1975-06-14

Family

ID=9756227

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1742351A SU474145A3 (ru)	1971-01-27	1972-01-27	Способ получени производных имидазолина

Country Status (17)

Country	Link
US (1)	US3818035A (2)
JP (1)	JPS4938273B1 (2)
AT (1)	AT311336B (2)
BE (1)	BE777689A (2)
CA (1)	CA962273A (2)
CH (1)	CH535254A (2)
DE (1)	DE2203373C3 (2)
DK (1)	DK138496B (2)
FI (1)	FI55841C (2)
GB (1)	GB1333471A (2)
HU (1)	HU162823B (2)
NL (1)	NL150454B (2)
NO (1)	NO134115C (2)
SE (1)	SE378426B (2)
SU (1)	SU474145A3 (2)
YU (1)	YU34694B (2)
ZA (1)	ZA72286B (2)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3927023A (en) *	1974-05-24	1975-12-16	Warner Lambert Co	Imidazolyl benzofurans
DE3049542A1 (de) *	1980-12-31	1982-07-29	Basf Ag, 6700 Ludwigshafen	Azolylalkyl-2,3-dihydrobenzofurane, diese enthaltende fungizide und verfahren zu ihrer herstellung
ZA825413B (en) *	1981-08-26	1983-06-29	Pfizer	Thromboxane synthetase inhibitors, processes for their production, and pharmaceutical compositions comprising them
US4806663A (en) *	1987-04-06	1989-02-21	The University Of Tennessee Research Corporation	Certain 3-substituted 2-alkyl benzofuran derivatives
US4851554A (en) *	1987-04-06	1989-07-25	University Of Tennessee Research Corporation	Certain 3-substituted 2-alkyl benzofuran derivatives
US4831156A (en) *	1987-09-30	1989-05-16	The University Of Tennessee Research Corp.	3-substituted 2-alkyl indole derivatives
DE69814012T2 (de) *	1997-12-19	2004-04-01	Eli Lilly And Co., Indianapolis	Hypoglykàmische imidazoline derivate
US7777035B2 (en) *	2005-06-22	2010-08-17	Chemocentryx, Inc.	Azaindazole compounds and methods of use
AU2007209381A1 (en) *	2006-01-27	2007-08-02	F. Hoffmann-La Roche Ag	Use of substituted 2-imidazole of imidazoline derivatives
AU2007312390B2 (en) *	2006-10-19	2013-03-28	F. Hoffmann-La Roche Ag	Aminomethyl-4-imidazoles
JP5167265B2 (ja) *	2006-10-19	2013-03-21	エフ．ホフマン−ラロシュアーゲー	微量アミン関連受容体に親和性を有するアミノメチル−２−イミダゾール
CA2668454A1 (en) *	2006-11-02	2008-05-08	F. Hoffmann-La Roche Ag	Substituted 2-imidazoles
WO2008058867A2 (en) *	2006-11-16	2008-05-22	F. Hoffmann-La Roche Ag	Substituted 4-imidazoles
ES2364701T3 (es) *	2006-12-13	2011-09-12	F. Hoffmann-La Roche Ag	Nuevos 2-imidazoles como ligandos para receptores asociados a aminas trazas.
US20080146523A1 (en) *	2006-12-18	2008-06-19	Guido Galley	Imidazole derivatives
EP2114906B1 (en)	2007-02-02	2014-08-06	F. Hoffmann-La Roche AG	2-aminooxazolines as taar1 ligands for cns disorders
CA2676944C (en) *	2007-02-15	2016-01-19	F. Hoffmann-La Roche Ag	2-aminooxazolines as taar1 ligands
WO2009003868A2 (en)	2007-07-02	2009-01-08	F. Hoffmann-La Roche Ag	2 -imidazolines having a good affinity to the trace amine associated receptors (taars)
AU2008270444A1 (en) *	2007-07-03	2009-01-08	F. Hoffmann-La Roche Ag	4-imidazolines and their use as antidepressants
CA2694362A1 (en) *	2007-07-27	2009-02-05	F. Hoffmann-La Roche Ag	2-azetidinemethaneamines and 2-pyrrolidinemethaneamines as taar-ligands
CA2695071A1 (en) *	2007-08-02	2009-02-05	F. Hoffmann-La Roche Ag	The use of benzamide derivatives for the treatment of cns disorders
AU2008285795A1 (en) *	2007-08-03	2009-02-12	F. Hoffmann-La Roche Ag	Pyridinecarboxamide and benzamide derivatives as TAAR1 ligands
US8242153B2 (en) *	2008-07-24	2012-08-14	Hoffmann-La Roche Inc.	4,5-dihydro-oxazol-2YL derivatives
RU2513086C2 (ru) *	2008-07-24	2014-04-20	Ф.Хоффманн-Ля Рош Аг	Производные 4,5-дигидро-оксазол-2-ила
US20100311798A1 (en) *	2009-06-05	2010-12-09	Decoret Guillaume	2-aminooxazolines as taar1 ligands
US8354441B2 (en) *	2009-11-11	2013-01-15	Hoffmann-La Roche Inc.	Oxazoline derivatives
US9452980B2 (en)	2009-12-22	2016-09-27	Hoffmann-La Roche Inc.	Substituted benzamides
WO2017157873A1 (en)	2016-03-17	2017-09-21	F. Hoffmann-La Roche Ag	5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of taar

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1121054B (de) *	1960-11-23	1962-01-04	Merck Ag E	Verfahren zur Herstellung eines neuen Imidazolinderivates und dessen Saeureadditionssalzen

1971
- 1971-01-27 GB GB332771A patent/GB1333471A/en not_active Expired
1972
- 1972-01-05 BE BE777689A patent/BE777689A/xx not_active IP Right Cessation
- 1972-01-06 CH CH17272A patent/CH535254A/fr not_active IP Right Cessation
- 1972-01-10 US US00216795A patent/US3818035A/en not_active Expired - Lifetime
- 1972-01-17 ZA ZA720286A patent/ZA72286B/xx unknown
- 1972-01-25 DE DE2203373A patent/DE2203373C3/de not_active Expired
- 1972-01-26 YU YU181/72A patent/YU34694B/xx unknown
- 1972-01-26 NO NO192/72A patent/NO134115C/no unknown
- 1972-01-26 HU HULA791A patent/HU162823B/hu not_active IP Right Cessation
- 1972-01-26 DK DK34572AA patent/DK138496B/da unknown
- 1972-01-26 SE SE7200867A patent/SE378426B/xx unknown
- 1972-01-27 CA CA133,337A patent/CA962273A/en not_active Expired
- 1972-01-27 JP JP47010207A patent/JPS4938273B1/ja active Pending
- 1972-01-27 SU SU1742351A patent/SU474145A3/ru active
- 1972-01-27 NL NL727201121A patent/NL150454B/xx not_active IP Right Cessation
- 1972-01-27 AT AT64772A patent/AT311336B/de not_active IP Right Cessation
- 1972-01-27 FI FI219/72A patent/FI55841C/fi active

Also Published As

Publication number	Publication date
GB1333471A (en)	1973-10-10
DK138496B (da)	1978-09-18
DE2203373B2 (de)	1977-08-11
NO134115B (2)	1976-05-10
CA962273A (en)	1975-02-04
NO134115C (2)	1976-08-18
DE2203373C3 (de)	1978-04-13
FI55841B (fi)	1979-06-29
JPS4938273B1 (2)	1974-10-16
YU34694B (en)	1979-12-31
AT311336B (de)	1973-11-12
SE378426B (2)	1975-09-01
DE2203373A1 (de)	1972-08-17
BE777689A (fr)	1972-07-05
ZA72286B (en)	1972-09-27
CH535254A (fr)	1973-03-31
AU3817772A (en)	1973-07-26
YU18172A (en)	1979-07-10
FI55841C (fi)	1979-10-10
NL150454B (nl)	1976-08-16
NL7201121A (2)	1972-07-31
US3818035A (en)	1974-06-18
DK138496C (2)	1979-02-26
HU162823B (2)	1973-04-28

Publication	Publication Date	Title
SU474145A3 (ru)	1975-06-14	Способ получени производных имидазолина
SU578883A3 (ru)	1977-10-30	Способ получени пиразолоизохинолинов или их солей
DE1545985B1 (de)	1970-11-12	Alkanolaminderivate und Verfahren zu deren Herstellung
Altman et al.	1971	An aldehyde synthesis utilizing the thiazole ring system.
Lindwall et al.	1931	Preparation of certain brominated cinchophens
SU453836A3 (ru)	1974-12-15	Способ получения производных 3-бензилпиридина или их солей
Yale	1947	o-Acetobenzoic Acid, its Preparation and Lactonization. A Novel Application of the Doebner1 Synthesis
US4020104A (en)	1977-04-26	Process for isomerizing cis,cis- and cis,trans-isomers of di-(p-aminocyclohexyl)methane to the corresponding trans,trans-isomer
SU465788A3 (ru)	1975-03-30	"Способ получени производных спиро (дибензо (а- ) -циклогептадиили три) ен-5:2" (4"-аминометилдиоксалана 1"3")
US4058563A (en)	1977-11-15	Novel schiff bases
SU516341A3 (ru)	1976-05-30	Способ получени замещенных бензофенонов
US2943092A (en)	1960-06-28	Method of preparing 4-amino-3-isoxazolidinones
SU506296A3 (ru)	1976-03-05	Способ получени 2-формил-3-карбонамидохиноксалин-ди- -окисей
US2502324A (en)	1950-03-28	Derivatives of diethylstilbestrol
SU423299A3 (ru)	1974-04-05	Способ получения производных тетрлгидробензодиазепинонл
SU1313856A1 (ru)	1987-05-30	Способ получени производных цис- или транс-диаминодибензоилдибензо-18-краун-6
SU501670A3 (ru)	1976-01-30	Способ получени производных циклопентено-хинолона
Phillips	1953	Reactivity of 5-Bromoisocytosine with Some Amines
Zaugg	1945	3, 4-Dimethylaniline from Fenchone
CH392483A (fr)	1965-05-31	Procédé de préparation de nouveaux esters d'acides 4-halo-3-sulfamoyl-benzoïques
US4038309A (en)	1977-07-26	Production of 2-hydroxynaphthalene-3-carboxylic acid
HU200323B (en)	1990-05-28	Process for production of n-/sulphonil-methil/-formamids
SU482453A1 (ru)	1975-08-30	Способ получени 2-фенацилхиноксалонов-3
Barfoot et al.	1957	293. ω-Halogenomethyl-pyridines,-quinolines, and-iso quinolines. Part VI. Compounds related to 1: 2-di-2′-quinolylethylene
US3312738A (en)	1967-04-04	Dibenzocycloheptenes and processes for the preparation thereof