GB1034938A - 2-phenylamino-1,3-diazacyclopent-2-enes - Google Patents
2-phenylamino-1,3-diazacyclopent-2-enesInfo
- Publication number
- GB1034938A GB1034938A GB39420/64A GB3942064A GB1034938A GB 1034938 A GB1034938 A GB 1034938A GB 39420/64 A GB39420/64 A GB 39420/64A GB 3942064 A GB3942064 A GB 3942064A GB 1034938 A GB1034938 A GB 1034938A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- chloro
- methylphenyl
- dichlorophenyl
- reacting
- 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
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
- C07D233/28—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 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises compounds of the Formula I <FORM:1034938/C2/1> wherein Z represents a 3,5-dichlorophenyl, 3,4-dichlorophenyl, 2,6-dibromophenyl, 2-fluoro-4 - chlorophenyl, 2 - trifluoromethylphenyl, 2 - methyl - 4 - chlorophenyl, 2 - chloro - 4-methylphenyl, 2 - chloro - 4 - ethylphenyl, 2 - chloro - 6 - ethylphenyl, 2 - chloro - 4 - tert.-butylphenyl, 2,6 - dichloro - 4 - methylphenyl, 2,4 - dichloro - 6 - methylphenyl, 2,4 - dimethyl-6-chlorophenyl or 2,6-dimethyl-4-chlorophenyl group; non-toxic, acid-addition salts thereof; a process for their preparation comprising reacting an isothiouronium salt of the formula <FORM:1034938/C2/2> wherein R1 represents a C1- 6 alkyl group and X represents the anion of an acid, with ethylene diamine in the absence of a solvent; and processes for the preparation of compounds of the Formula I in which Z represents a 2,6-dichlorophenyl, 2 - chloro - 6 - methylphenyl or 2,4,6 - trimethylphenyl group, in addition to the groups specified above for Z, comprising (a) reacting an isothiouronium salt of the formula: <FORM:1034938/C2/3> wherein Z1 represents the groups specified above for Z and also a 2,6-dichlorophenyl, 2-chloro-6-methylphenyl or 2,4,6-trimethylphenyl group, with ethylene diamine in the presence of a solvent, or (b) reacting a thiourea derivative of the formula <FORM:1034938/C2/4> with ethylene diamine, or (c) pyrolysing a compound of the formula <FORM:1034938/C2/5> wherein Y represents an oxygen or sulphur atom, to effect ring closure. Isothiouronium salts of Formula III are prepared by reacting an appropriately substituted aniline with ammonium thiocyanate to produce a thiourea derivative of Formula IV, which is reacted with an alkyl compound, e.g. an alkyl halide or dialkyl sulphate, in a suitable solvent. Pharmaceutical compositions having hypotensive activity, for oral, parenteral or rectal administration, comprise a compound of the invention, or a compound of Formula I in which Z represents a 2,6-dichlorophenyl, 2-chloro - 6 - methylphenyl or 2,4,6 - trimethylphenyl group, together with a pharmaceutical carrier.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1963B0073766 DE1445505B2 (en) | 1963-10-04 | 1963-10-04 | 2-PHENYLAMINO-1,3-DIAZACYCLOPENTENE- (2) SUBSTITUTED IN THE PHENYL CORE |
| DEB0077921 | 1964-07-31 | ||
| DEB0077922 | 1964-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1034938A true GB1034938A (en) | 1966-07-06 |
Family
ID=27209240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39420/64A Expired GB1034938A (en) | 1963-10-04 | 1964-09-28 | 2-phenylamino-1,3-diazacyclopent-2-enes |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE653933A (en) |
| BR (1) | BR6463142D0 (en) |
| CH (3) | CH451172A (en) |
| DE (2) | DE1445505B2 (en) |
| DK (2) | DK108364C (en) |
| FI (2) | FI44913C (en) |
| FR (2) | FR3968M (en) |
| GB (1) | GB1034938A (en) |
| IL (1) | IL22186A (en) |
| NL (1) | NL123037C (en) |
| SE (2) | SE353721B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3462433A (en) * | 1965-10-01 | 1969-08-19 | Boehringer Sohn Ingelheim | Derivatives of 2-(2'-halo-anilino)1,3-diazacyclo-pentene-(2) |
| US4125620A (en) | 1974-10-01 | 1978-11-14 | Boehringer Ingelheim Gmbh | 2-[(2',6'-Disubstituted-phenyl)-imino]-imidazolidines and salts thereof |
| US4244957A (en) | 1977-11-07 | 1981-01-13 | Hoffman-La Roche Inc. | 2-Imino-imidazolidine derivatives |
| US4366160A (en) | 1980-09-10 | 1982-12-28 | Hoffmann-La Roche Inc. | Imidazole derivatives |
| EP0116768A1 (en) * | 1982-12-23 | 1984-08-29 | Smithkline Beckman Corporation | 2-(4-Tert.-butyl-2,6-dichlorophenylimino)imidazolidine |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754832A (en) * | 1969-08-14 | 1971-02-15 | Beecham Group Ltd | IMINAZOLINES |
| DE2806811A1 (en) * | 1978-02-17 | 1979-08-23 | Boehringer Sohn Ingelheim | NEW SUBSTITUTED 2-PHENYLIMINO-IMIDAZOLIDINE, THEIR ACID-ADDITIONAL SALTS, THESE MEDICINAL PRODUCTS AND METHOD FOR MANUFACTURING THE SAME |
| DE2854659A1 (en) * | 1978-12-18 | 1980-07-10 | Boehringer Sohn Ingelheim | NEW 3,4-DISUBSTITUTED 2-PHENYLIMINO IMIDAZOLIDINES, THEIR ACID ADDITION SALTS, THE MEDICINAL PRODUCTS CONTAINING THEM AND METHOD FOR THE PRODUCTION THEREOF |
-
0
- NL NL123037D patent/NL123037C/xx active
-
1963
- 1963-10-04 DE DE1963B0073766 patent/DE1445505B2/en active Granted
-
1964
- 1964-07-31 DE DE19641445538 patent/DE1445538A1/en active Pending
- 1964-09-14 CH CH1189367A patent/CH451172A/en unknown
- 1964-09-14 CH CH1193264A patent/CH437316A/en unknown
- 1964-09-14 CH CH1193164A patent/CH451169A/en unknown
- 1964-09-16 SE SE1071068A patent/SE353721B/xx unknown
- 1964-09-16 SE SE1110764A patent/SE313310B/xx unknown
- 1964-09-23 FI FI201764A patent/FI44913C/en active
- 1964-09-28 GB GB39420/64A patent/GB1034938A/en not_active Expired
- 1964-10-01 FR FR990056A patent/FR3968M/fr not_active Expired
- 1964-10-01 FR FR990057A patent/FR1448765A/en not_active Expired
- 1964-10-02 BE BE653933D patent/BE653933A/xx unknown
- 1964-10-02 DK DK486964A patent/DK108364C/en active
- 1964-10-02 BR BR16314264A patent/BR6463142D0/en unknown
- 1964-10-04 IL IL2218664A patent/IL22186A/en unknown
-
1965
- 1965-09-20 DK DK482765A patent/DK117000B/en unknown
-
1971
- 1971-09-17 FI FI260071A patent/FI49614C/en active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3462433A (en) * | 1965-10-01 | 1969-08-19 | Boehringer Sohn Ingelheim | Derivatives of 2-(2'-halo-anilino)1,3-diazacyclo-pentene-(2) |
| US4125620A (en) | 1974-10-01 | 1978-11-14 | Boehringer Ingelheim Gmbh | 2-[(2',6'-Disubstituted-phenyl)-imino]-imidazolidines and salts thereof |
| US4244957A (en) | 1977-11-07 | 1981-01-13 | Hoffman-La Roche Inc. | 2-Imino-imidazolidine derivatives |
| US4355033A (en) | 1977-11-07 | 1982-10-19 | Hoffman-La Roche Inc. | 2-Imino-imidazolidine derivatives |
| US4366160A (en) | 1980-09-10 | 1982-12-28 | Hoffmann-La Roche Inc. | Imidazole derivatives |
| EP0116768A1 (en) * | 1982-12-23 | 1984-08-29 | Smithkline Beckman Corporation | 2-(4-Tert.-butyl-2,6-dichlorophenylimino)imidazolidine |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1445505B2 (en) | 1976-12-16 |
| SE313310B (en) | 1969-08-11 |
| FI49614B (en) | 1975-04-30 |
| NL123037C (en) | |
| DK117000B (en) | 1970-03-09 |
| FR3968M (en) | 1966-02-28 |
| CH451172A (en) | 1968-05-15 |
| DE1445505A1 (en) | 1969-10-02 |
| BR6463142D0 (en) | 1973-07-19 |
| CH451169A (en) | 1968-05-15 |
| CH437316A (en) | 1967-06-15 |
| IL22186A (en) | 1968-06-20 |
| FI44913B (en) | 1971-11-01 |
| DK108364C (en) | 1967-11-27 |
| SE353721B (en) | 1973-02-12 |
| FR1448765A (en) | 1966-03-18 |
| BE653933A (en) | 1965-04-02 |
| FI49614C (en) | 1975-08-11 |
| FI44913C (en) | 1972-02-10 |
| DE1445538A1 (en) | 1969-02-20 |
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