CA1146949A - 2-(2-chloro-4-cyclopropyl-phenylimino)-imidazolidine; ses sels d'addition acide; compositions pharmaceutiques qui en renferment et procedes pour les preparer - Google Patents

2-(2-chloro-4-cyclopropyl-phenylimino)-imidazolidine; ses sels d'addition acide; compositions pharmaceutiques qui en renferment et procedes pour les preparer

Info

Publication number: CA1146949A
Authority: CA; Canada
Prior art keywords: formula; compound; acid addition; addition salt; acid
Prior art date: 1980-09-15
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

CA000360243A

Other languages

English (en)

Inventor

Helmut Stahle

Herbert Koppe

Werner Kummer

Wolfgang Hoefke

Ludwig Pichler

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 GmbH

Original Assignee

Boehringer Ingelheim 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.)

1980-09-15

Filing date

1980-09-15

Publication date

1983-05-24

1980-09-15 Application filed by Boehringer Ingelheim GmbH filed Critical Boehringer Ingelheim GmbH

1980-09-15 Priority to CA000360243A priority Critical patent/CA1146949A/fr

1983-05-24 Application granted granted Critical

1983-05-24 Publication of CA1146949A publication Critical patent/CA1146949A/fr

Status Expired legal-status Critical Current

Links

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238000007069 methylation reaction Methods 0.000 description 1
YXPOTYIIRALLPH-UHFFFAOYSA-N n'-(7-chloroquinolin-4-yl)propane-1,3-diamine Chemical compound ClC1=CC=C2C(NCCCN)=CC=NC2=C1 YXPOTYIIRALLPH-UHFFFAOYSA-N 0.000 description 1
RRLNUWRVTRDWIX-UHFFFAOYSA-N n-(4-cyclopropylphenyl)acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1CC1 RRLNUWRVTRDWIX-UHFFFAOYSA-N 0.000 description 1
JCOPITWIWLFFPC-UHFFFAOYSA-N n-phenyl-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1CCN=C1NC1=CC=CC=C1 JCOPITWIWLFFPC-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
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230000035484 reaction time Effects 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000360243A 1980-09-15 1980-09-15 2-(2-chloro-4-cyclopropyl-phenylimino)-imidazolidine; ses sels d'addition acide; compositions pharmaceutiques qui en renferment et procedes pour les preparer Expired CA1146949A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000360243A CA1146949A (fr)	1980-09-15	1980-09-15	2-(2-chloro-4-cyclopropyl-phenylimino)-imidazolidine; ses sels d'addition acide; compositions pharmaceutiques qui en renferment et procedes pour les preparer

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000360243A CA1146949A (fr)	1980-09-15	1980-09-15	2-(2-chloro-4-cyclopropyl-phenylimino)-imidazolidine; ses sels d'addition acide; compositions pharmaceutiques qui en renferment et procedes pour les preparer

Publications (1)

Publication Number	Publication Date
CA1146949A true CA1146949A (fr)	1983-05-24

Family

ID=4117882

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000360243A Expired CA1146949A (fr)	1980-09-15	1980-09-15	2-(2-chloro-4-cyclopropyl-phenylimino)-imidazolidine; ses sels d'addition acide; compositions pharmaceutiques qui en renferment et procedes pour les preparer

Country Status (1)

Country	Link
CA (1)	CA1146949A (fr)

1980
- 1980-09-15 CA CA000360243A patent/CA1146949A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-05-24	MKEX	Expiry

Publication	Publication Date	Title
US4250186A (en)	1981-02-10	Method of slowing heart rate
CA1085861A (fr)	1980-09-16	Obtention de 2-phenyamino-imidazolines-(2) a substitution, de leurs sels d'addition et de produits pharmaceutiques qui en derivent
CA1056836A (fr)	1979-06-19	Les 2-phenyliminoimidazolidines substituees en 2,6, leurs sels d'addition, produits pharmaceutiques qui en contiennent et procede pour leur production
CA1088550A (fr)	1980-10-28	2-bromo-6-fluoro-n-2-imidazolidinylidene-benzamine
US4213995A (en)	1980-07-22	2-Phenylimino-imidazolidines and salts thereof
US3937717A (en)	1976-02-10	2-phenylamino-imidazolines-(2)
US4277487A (en)	1981-07-07	Substituted 2-phenylamino-2-imidazolines as bradycardiacs
IE50570B1 (en)	1986-05-14	2-phenylamino-imidazolines-(2),compositions and processes for the preparation thereof
US4036972A (en)	1977-07-19	2-(N-thienylmethyl-phenylamino)-imidazolines-(2) and salts thereof
US4341788A (en)	1982-07-27	2-(2-Chloro-4-cyclopropyl-phenyl-imino)-imidazolidine, and acid addition salts thereof as bradycardiacs
US4210659A (en)	1980-07-01	Substituted 7-phenyl-2,3-dihydro-imidazo[1,2-α]imidazoles and salts thereof
US4263300A (en)	1981-04-21	Substituted 2-phenylamino-1,3-tetrahydro-2-pyrimidines and salts thereof
NZ194833A (en)	1984-07-06	2-(2-chloro-4-cyclopropylphenylimino)-imidazolidine and pharmaceutical compositions
IE50485B1 (en)	1986-04-30	Novel substituted 2-phenylamino-imidazolines-(2),the acid addition salts thereof,pharmaceuticals containing same and processes for the preparation thereof
US4215133A (en)	1980-07-29	2-[N-(2'-Chloro-4'-methyl-thienyl-3')-N-(cyclopropyl-methyl)-amino]-2-imidazoline and salts thereof
US4239764A (en)	1980-12-16	Substituted 2-phenylamino-2-imidazolines and salts thereof
Avendano et al.	1985	2, 4, 4‐trisubstituted 5‐amino‐4h‐imidazoles. A new synthetic approach and reactivity
KR860000669B1 (ko)	1986-05-29	2-(2-클로로-4-사이클로프로필페닐이미노)-이미다졸리딘의 제조방법
EP0202461A1 (fr)	1986-11-26	Dérivés de la (N-alkinyl-N-phénylamino)-2 imidazolidine, leurs sels d'addition d'acides, médicaments les contenant et leur procédé de préparation
US4409235A (en)	1983-10-11	Substituted 7-(2,6-dibromo-4-methyl-phenyl)-2,3-dihydro-imidazo[1,2-a]imidazoles, compositions and use
PL131883B1 (en)	1985-01-31	Process for preparing 2-/2-chloro-4-cyclopropylphenylimino/-imidazolidine
JPS5993074A (ja)	1984-05-29	ピリミドン誘導体