CA1094566A - Imidazoline derivatives - Google Patents

Imidazoline derivatives

Info

Publication number: CA1094566A
Authority: CA; Canada
Prior art keywords: radical; cyclobutyl; cyclopentyl; derivative; reacting
Prior art date: 1977-06-13
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

CA305,122A

Other languages

English (en)

French (fr)

Inventor

Icilio A.G. Cavero

Henry Najer

Braham Shroot

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.)

Synthelabo SA

Original Assignee

Synthelabo SA

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.)

1977-06-13

Filing date

1978-06-09

Publication date

1981-01-27

1978-06-09 Application filed by Synthelabo SA filed Critical Synthelabo SA

1981-01-27 Application granted granted Critical

1981-01-27 Publication of CA1094566A publication Critical patent/CA1094566A/en

Status Expired legal-status Critical Current

Links

150000002462 imidazolines Chemical class 0.000 title claims abstract description 9
229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 title abstract description 4
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims abstract description 7
VLLSCJFPVSQXDM-UHFFFAOYSA-N 2-phenoxyacetonitrile Chemical class N#CCOC1=CC=CC=C1 VLLSCJFPVSQXDM-UHFFFAOYSA-N 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
239000002253 acid Substances 0.000 claims abstract description 5
GHCCHMFFNHOXEU-UHFFFAOYSA-N 2-(chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride Chemical compound Cl.ClCC1=NCCN1 GHCCHMFFNHOXEU-UHFFFAOYSA-N 0.000 claims abstract description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 4
HVCCFMAPGCBCHZ-UHFFFAOYSA-N 2-aminoethylazanium;4-methylbenzenesulfonate Chemical compound NCCN.CC1=CC=C(S(O)(=O)=O)C=C1 HVCCFMAPGCBCHZ-UHFFFAOYSA-N 0.000 claims abstract description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 19
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
159000000000 sodium salts Chemical class 0.000 claims description 3
GRMJZZBFHKTYDJ-UHFFFAOYSA-N 2-(phenoxymethyl)-4,5-dihydro-1h-imidazole Chemical class N=1CCNC=1COC1=CC=CC=C1 GRMJZZBFHKTYDJ-UHFFFAOYSA-N 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000000126 substance Substances 0.000 claims 4
BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical group [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 claims 3
ZAEBLFKQMDEPDM-UHFFFAOYSA-N cyclobutyl radical Chemical group [CH]1CCC1 ZAEBLFKQMDEPDM-UHFFFAOYSA-N 0.000 claims 3
231100000252 nontoxic Toxicity 0.000 claims 3
230000003000 nontoxic effect Effects 0.000 claims 3
239000005526 vasoconstrictor agent Substances 0.000 abstract description 3
239000007923 nasal drop Substances 0.000 abstract 1
229940100662 nasal drops Drugs 0.000 abstract 1
239000007922 nasal spray Substances 0.000 abstract 1
CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
210000000709 aorta Anatomy 0.000 description 4
241000283973 Oryctolagus cuniculus Species 0.000 description 3
241000700159 Rattus Species 0.000 description 3
230000008602 contraction Effects 0.000 description 3
239000000155 melt Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229960005016 naphazoline Drugs 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
WVCPIDFKPPPYRA-UHFFFAOYSA-N 2-(2-cyclohexylphenoxy)-1-methyl-4,5-dihydroimidazole Chemical compound C1(CCCCC1)C1=C(OC=2N(CCN2)C)C=CC=C1 WVCPIDFKPPPYRA-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
239000013081 microcrystal Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
206010039083 rhinitis Diseases 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000003639 vasoconstrictive effect Effects 0.000 description 2
DCAIEYUJOVJWCG-UHFFFAOYSA-N 2-cyclobutylphenol Chemical compound OC1=CC=CC=C1C1CCC1 DCAIEYUJOVJWCG-UHFFFAOYSA-N 0.000 description 1
MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
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 1
206010028735 Nasal congestion Diseases 0.000 description 1
206010047139 Vasoconstriction Diseases 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA305,122A 1977-06-13 1978-06-09 Imidazoline derivatives Expired CA1094566A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7717990		1977-06-13
FR7717990A FR2394532A1 (fr)	1977-06-13	1977-06-13	Derives d'imidazoline et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
CA1094566A true CA1094566A (en)	1981-01-27

Family

ID=9192012

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA305,122A Expired CA1094566A (en)	1977-06-13	1978-06-09	Imidazoline derivatives

Country Status (17)

Country	Link
JP (1)	JPS545975A (da)
AU (1)	AU515492B2 (da)
BE (1)	BE867984A (da)
CA (1)	CA1094566A (da)
CH (1)	CH635081A5 (da)
DE (1)	DE2825388A1 (da)
DK (1)	DK258778A (da)
FR (1)	FR2394532A1 (da)
GB (1)	GB1572689A (da)
IE (1)	IE46988B1 (da)
IT (1)	IT1095286B (da)
LU (1)	LU79794A1 (da)
NL (1)	NL7806269A (da)
NO (1)	NO782027L (da)
NZ (1)	NZ187507A (da)
SE (1)	SE7806740L (da)
ZA (1)	ZA783327B (da)

1977
- 1977-06-13 FR FR7717990A patent/FR2394532A1/fr active Granted
1978
- 1978-05-23 GB GB21685/78A patent/GB1572689A/en not_active Expired
- 1978-06-09 DK DK258778A patent/DK258778A/da unknown
- 1978-06-09 IE IE1169/78A patent/IE46988B1/en unknown
- 1978-06-09 ZA ZA00783327A patent/ZA783327B/xx unknown
- 1978-06-09 DE DE19782825388 patent/DE2825388A1/de not_active Withdrawn
- 1978-06-09 NO NO782027A patent/NO782027L/no unknown
- 1978-06-09 NZ NZ187507A patent/NZ187507A/xx unknown
- 1978-06-09 BE BE188459A patent/BE867984A/xx unknown
- 1978-06-09 SE SE7806740A patent/SE7806740L/xx unknown
- 1978-06-09 NL NL7806269A patent/NL7806269A/xx not_active Application Discontinuation
- 1978-06-09 LU LU79794A patent/LU79794A1/xx unknown
- 1978-06-09 CA CA305,122A patent/CA1094566A/en not_active Expired
- 1978-06-09 JP JP7028878A patent/JPS545975A/ja active Pending
- 1978-06-09 AU AU36994/78A patent/AU515492B2/en not_active Expired
- 1978-06-09 CH CH632778A patent/CH635081A5/fr not_active IP Right Cessation
- 1978-06-09 IT IT24416/78A patent/IT1095286B/it active

Also Published As

Publication number	Publication date
LU79794A1 (fr)	1978-11-28
BE867984A (fr)	1978-12-11
ZA783327B (en)	1979-06-27
GB1572689A (en)	1980-07-30
NZ187507A (en)	1979-10-25
NO782027L (no)	1978-12-14
CH635081A5 (en)	1983-03-15
IE46988B1 (en)	1983-11-16
AU515492B2 (en)	1981-04-09
IT7824416A0 (it)	1978-06-09
IT1095286B (it)	1985-08-10
DK258778A (da)	1978-12-14
NL7806269A (nl)	1978-12-15
FR2394532A1 (fr)	1979-01-12
DE2825388A1 (de)	1979-01-04
SE7806740L (sv)	1978-12-14
FR2394532B1 (da)	1980-01-18
JPS545975A (en)	1979-01-17
IE781169L (en)	1978-12-13
AU3699478A (en)	1979-12-13

Legal Events

Date	Code	Title	Description
1998-01-27	MKEX	Expiry

Publication	Publication Date	Title
JPS6056143B2 (ja)	1985-12-09	アミジン誘導体ならびにその製造法
IE56836B1 (en)	1992-01-01	Novel pharmaceutically active 1,2,3,4,4a,5,10,10a-octahydrobenzo(g)quinoline derivatives
DE2027645A1 (de)	1971-12-09	Piperazinylalkyl chinazolon (4) den vate, Verfahren zu deren Herstellung und sie enthaltende Arzneimittel
WO1998011062A1 (de)	1998-03-19	Benzamidinderivate und ihre verwendung als arzneimittel mit ltb4-antagonistischer wirkung
US3850926A (en)	1974-11-26	2-(n-substituted-phenylamino)-imidazolines-(2)
PL115759B1 (en)	1981-04-30	Process for preparing novel substituted 2-phenyliminoimidazolidyns
PT89120B (pt)	1993-04-30	Processo para a preparacao de novos derivados flavonoides 2-piperazinil-2-oxo-etileno substituidos
CA1094566A (en)	1981-01-27	Imidazoline derivatives
NO771610L (no)	1977-11-08	Fremgangsm}te for fremstilling av kinazolin-derivater
US2235638A (en)	1941-03-18	Process of preparing derivatives of pyrimidine
JPS6140268A (ja)	1986-02-26	イミダゾリン、その付加塩及びその製造方法並びにイミダゾリン又はその付加塩を有効成分とする医薬
US3449357A (en)	1969-06-10	2-((2,6-substituted)phenoxymethyl)-2-imidazolines
Wenner	1965	1, 2, 3, 4-Tetrahydroisoquinoline derivatives with antihypertensive properties
US4261998A (en)	1981-04-14	Tetrahydro-isoquinoline derivatives
DE2651789A1 (de)	1977-06-02	Heterocyclische derivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
US3957785A (en)	1976-05-18	Bβ-Pyrimidino-aminomethyl-10α-ergoline and 10α-methoxyergoline derivatives
FI57589B (fi)	1980-05-30	Foerfarande foer framstaellning av blodtrycket saenkande 6-substituerade 3-karbetoksihydrazinopyridaziner
HU188074B (en)	1986-03-28	Process for the preparation of cimetidin
EP0007438A1 (de)	1980-02-06	Neue substituierte 2-Phenylamino-imidazoline-(2), deren Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zur Herstellung derselben
US3042674A (en)	1962-07-03	Xanthene and thiaxanthene cyclic amidines
DE3108753A1 (de)	1982-09-16	Neue substituierte alkyl-phenylsulfonylguanidine miteinem heterocyclischen rest
US3686178A (en)	1972-08-22	Preparation of 4-aryl-2(1h)-quinazolinones and thiones
US2934535A (en)	1960-04-26	Z-amino-x-trifluoromethylanilino-s
DE2122070A1 (de)	1972-06-08	1 Veratryl 4 methyl 5 athyl 7,8 dimethoxy 2,3 diazabicyclo eckige Klam mer auf 5,4,0 eckige Klammer zu undeca pentaen (1,3,6,8,10) und seine Verwendung
OA11955A (en)	2006-04-13	Polymorphs of crystalline (2-benzhydryl-1-azabicycloÄ2-2-2-Üoct-3-yl)-(5-isopropyl-2-methoxybenzyl)-amine citrate as NK-1 receptor antagonists.