GB1267433A - Novel imidazoline derivatives, the preparation thereof, and compositions containing the same - Google Patents
Novel imidazoline derivatives, the preparation thereof, and compositions containing the sameInfo
- Publication number
- GB1267433A GB1267433A GB5580469A GB5580469A GB1267433A GB 1267433 A GB1267433 A GB 1267433A GB 5580469 A GB5580469 A GB 5580469A GB 5580469 A GB5580469 A GB 5580469A GB 1267433 A GB1267433 A GB 1267433A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- amino
- prepared
- acid addition
- reaction
- Prior art date
- 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
Links
- 150000002462 imidazolines Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- -1 2-benzothiazolyl group Chemical group 0.000 abstract 2
- LDUCTLWCKOLAPM-UHFFFAOYSA-N 2-methyl-1h-pyridin-2-amine Chemical class CC1(N)NC=CC=C1 LDUCTLWCKOLAPM-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- MTIMDGQILFWMJI-UHFFFAOYSA-N 2-methylsulfanyl-4,5-dihydro-1h-imidazole Chemical compound CSC1=NCCN1 MTIMDGQILFWMJI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000002541 isothioureas Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE754832D BE754832A (fr) | 1969-08-14 | Iminazolines | |
| GB5580469A GB1267433A (en) | 1969-08-14 | 1969-08-14 | Novel imidazoline derivatives, the preparation thereof, and compositions containing the same |
| ZA705540A ZA705540B (en) | 1969-11-14 | 1970-08-11 | "organic compounds" |
| DE19702040374 DE2040374A1 (de) | 1969-08-14 | 1970-08-13 | Imidazoline,ihre Saeureadditionssalze und Verfahren zu ihrer Herstellung |
| ES382731A ES382731A1 (es) | 1969-08-14 | 1970-08-13 | Un procedimiento para la preparacion de iminazolinas. |
| FR7029979A FR2068499B1 (enrdf_load_html_response) | 1969-08-14 | 1970-08-14 | |
| NL7012086A NL7012086A (enrdf_load_html_response) | 1969-08-14 | 1970-08-14 | |
| AT740670A AT296975B (de) | 1969-08-14 | 1970-08-14 | Verfahren zur Herstellung von neuen Imidazolinderivaten und ihren Salzen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5580469A GB1267433A (en) | 1969-08-14 | 1969-08-14 | Novel imidazoline derivatives, the preparation thereof, and compositions containing the same |
| GB4066669 | 1969-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1267433A true GB1267433A (en) | 1972-03-22 |
Family
ID=26264467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5580469A Expired GB1267433A (en) | 1969-08-14 | 1969-08-14 | Novel imidazoline derivatives, the preparation thereof, and compositions containing the same |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT296975B (enrdf_load_html_response) |
| BE (1) | BE754832A (enrdf_load_html_response) |
| DE (1) | DE2040374A1 (enrdf_load_html_response) |
| ES (1) | ES382731A1 (enrdf_load_html_response) |
| FR (1) | FR2068499B1 (enrdf_load_html_response) |
| GB (1) | GB1267433A (enrdf_load_html_response) |
| NL (1) | NL7012086A (enrdf_load_html_response) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008880A1 (en) * | 1978-08-31 | 1980-03-19 | Eli Lilly And Company | 1-(2,6-Dichlorobenzoyl)-3-(5-substituted-2-pyridinyl) ureas, their preparation, formulations and use as insecticides |
| EP0008881A1 (en) * | 1978-08-31 | 1980-03-19 | Eli Lilly And Company | 1-Benzoyl-3-pyridinyl ureas, their use as insecticides, their preparation and formulations containing them |
| US4203988A (en) | 1975-11-12 | 1980-05-20 | Merck & Co., Inc. | Pyridinyl ureas and pharmaceutical use |
| US4323570A (en) | 1978-11-15 | 1982-04-06 | Beiersdorf Aktiengesellschaft | Substituted aminopyrimidines |
| US4434167A (en) | 1979-11-07 | 1984-02-28 | Beiersdorf Aktiengesellschaft | Pyrimidyl thioureas useful for the treatment of hypertension and hyperlipidemia |
| EP0121082A1 (de) * | 1983-03-04 | 1984-10-10 | Bayer Ag | Guanidin-Derivate |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH570401A5 (enrdf_load_html_response) * | 1972-05-09 | 1975-12-15 | Wander Ag Dr A | |
| GB1444558A (en) * | 1973-02-17 | 1976-08-04 | Beecham Group Ltd | Pyridylthioureas |
| GB1408362A (en) * | 1973-05-25 | 1975-10-01 | Lepetit Spa | 2-pyrrol-1-yl amino 4,5-dihydro-1-h-imidazole derivatives |
| FR2358890A1 (fr) * | 1976-05-24 | 1978-02-17 | Science Union & Cie | Nouvelles aryl trifluoroethylamines, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
| CH632268A5 (de) | 1977-01-14 | 1982-09-30 | Sandoz Ag | Verfahren zur herstellung von neuen heterocyclylaminoderivaten. |
| DE2816627A1 (de) * | 1978-04-17 | 1979-10-25 | Beiersdorf Ag | 2-(n-amino-isoindolinyl)-imidazolin und verfahren zu seiner herstellung |
| DE2905501A1 (de) * | 1979-02-14 | 1980-08-28 | Beiersdorf Ag | Neue kondensierte, stickstoffhaltige heterocyclische verbindungen und verfahren zu deren herstellung |
| DE2849537C2 (de) * | 1978-11-15 | 1983-03-17 | Beiersdorf Ag, 2000 Hamburg | Substituierte 5-(2-Imidazolin-2-yl)-aminopyrimidine, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| MA18829A1 (fr) * | 1979-05-18 | 1980-12-31 | Ciba Geigy Ag | Derives de la pyrimidine,procedes pour leur preparation,compositions pharmaceutiques contenant ces composes et leur utilisation therapeutique |
| FR2462436A1 (fr) * | 1979-07-31 | 1981-02-13 | Abbott Lab | Nouvelles 2-(5-pyrazolylamino)-2-imidazolines, utiles notamment comme agents anti-inflammatoires, et compositions pharmaceutiques les contenant |
| WO1998023612A1 (en) * | 1996-11-25 | 1998-06-04 | The Procter & Gamble Company | 2-imidazolinylaminobenzothiazole compounds useful as alpha-2 adrenoceptor agonists |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1211341A (fr) * | 1955-12-19 | 1960-03-15 | A Wander Dr | Procédé pour la préparation de 2-amino-imidazolines |
| NL123037C (enrdf_load_html_response) * | 1963-10-04 |
-
0
- BE BE754832D patent/BE754832A/xx unknown
-
1969
- 1969-08-14 GB GB5580469A patent/GB1267433A/en not_active Expired
-
1970
- 1970-08-13 DE DE19702040374 patent/DE2040374A1/de active Pending
- 1970-08-13 ES ES382731A patent/ES382731A1/es not_active Expired
- 1970-08-14 FR FR7029979A patent/FR2068499B1/fr not_active Expired
- 1970-08-14 NL NL7012086A patent/NL7012086A/xx unknown
- 1970-08-14 AT AT740670A patent/AT296975B/de active
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4203988A (en) | 1975-11-12 | 1980-05-20 | Merck & Co., Inc. | Pyridinyl ureas and pharmaceutical use |
| EP0008880A1 (en) * | 1978-08-31 | 1980-03-19 | Eli Lilly And Company | 1-(2,6-Dichlorobenzoyl)-3-(5-substituted-2-pyridinyl) ureas, their preparation, formulations and use as insecticides |
| EP0008881A1 (en) * | 1978-08-31 | 1980-03-19 | Eli Lilly And Company | 1-Benzoyl-3-pyridinyl ureas, their use as insecticides, their preparation and formulations containing them |
| US4323570A (en) | 1978-11-15 | 1982-04-06 | Beiersdorf Aktiengesellschaft | Substituted aminopyrimidines |
| US4434167A (en) | 1979-11-07 | 1984-02-28 | Beiersdorf Aktiengesellschaft | Pyrimidyl thioureas useful for the treatment of hypertension and hyperlipidemia |
| EP0121082A1 (de) * | 1983-03-04 | 1984-10-10 | Bayer Ag | Guanidin-Derivate |
| US4602938A (en) * | 1983-03-04 | 1986-07-29 | Bayer Aktiengesellschaft | N'-(substituted-pyrimidin-2-yl)-N"-substituted-N",N"'-bis-(substituted-benzenesulphonyl)-guanidines as herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7012086A (enrdf_load_html_response) | 1971-02-16 |
| ES382731A1 (es) | 1973-04-16 |
| AT296975B (de) | 1972-03-10 |
| FR2068499A1 (enrdf_load_html_response) | 1971-08-27 |
| FR2068499B1 (enrdf_load_html_response) | 1974-08-30 |
| DE2040374A1 (de) | 1971-02-25 |
| BE754832A (fr) | 1971-02-15 |
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