GB973882A - Benzyl-guanidines,their preparation and pharmaceutical compositions containing them - Google Patents
Benzyl-guanidines,their preparation and pharmaceutical compositions containing themInfo
- Publication number
- GB973882A GB973882A GB43702/59A GB4370259A GB973882A GB 973882 A GB973882 A GB 973882A GB 43702/59 A GB43702/59 A GB 43702/59A GB 4370259 A GB4370259 A GB 4370259A GB 973882 A GB973882 A GB 973882A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzyl
- hydrogen atom
- group
- salt
- atom
- 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
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- -1 S-substituted isothiourea Chemical class 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- PFQSWGVSKHFMSO-UHFFFAOYSA-N methyl n'-benzylcarbamimidothioate;hydroiodide Chemical class I.CSC(=N)NCC1=CC=CC=C1 PFQSWGVSKHFMSO-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- HRUWBAUPQXBXBY-UHFFFAOYSA-N 1-benzyl-1-methylguanidine Chemical compound NC(=N)N(C)CC1=CC=CC=C1 HRUWBAUPQXBXBY-UHFFFAOYSA-N 0.000 abstract 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract 1
- 206010020772 Hypertension Diseases 0.000 abstract 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 230000002889 sympathetic effect Effects 0.000 abstract 1
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of general formula <FORM:0973882/C1/1> wherein Z1 is a hydrogen atom or a substituent halogen atom or alkyl or nitro group in the 2 or 3 position, Z2 is a hydrogen atom or a substituent halogen atom or alkyl group in the 4, 5 or 6 position, and R1, R2, R3 and R4 are the same or different and each is a hydrogen atom or a substituent alkyl group, provided that when Z1 is a hydrogen atom at least two of Z2, R1, R2, R3 and R4 are not hydrogen but are substituents as defined; acid addition salts thereof; and their preparation by (1) reacting a guanidine R5N=C(NR6R7)(NR8R9) or a salt thereo with a compound R10X where R5, R6, R7, R8, R9 and R10 are each as appropriate, and not as respective, a benzyl, R1, R2, R3 and R4 group and a hydrogen atom, and X is a reactive proton accepting atom or group, and (2) reacting ammonia or an ammonia derivative or a salt thereof with an S-substituted isothiourea or a salt thereof, or with a cyanamide. N-Benzyl-S-methylisothiourea hydriodides are prepared by treating with methyl iodide corresponding benzyl-thioureas obtained from ammonia derivatives and isothiocyanates. N-Benzyl-N1-methylguanidine is prepared from methylamine and N-benzyl-S-methylisothiourea hydriodide. Pharmaceutical compositions comprise Compounds I or their acid addition salts together with acceptable carriers. Forms mentioned are powders, granules, capsules, cachets, tablets (oral administration), solutions and suspensions (oral and parenteral), suppositories and pessaries. The compounds depress sympathetic function and may be used to treat hypertension.
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB43702/59A GB973882A (en) | 1959-12-23 | 1959-12-23 | Benzyl-guanidines,their preparation and pharmaceutical compositions containing them |
| US77032A US3168562A (en) | 1959-12-23 | 1960-12-20 | Substituted benzylguanidines |
| CA813,371A CA940537A (en) | 1959-12-23 | 1960-12-20 | Benzyl guanidines, and a process of production |
| LU39574A LU39574A1 (en) | 1959-12-23 | 1960-12-22 | Chemical compounds, processes and pharmaceutical preparations |
| CS7672A CS149570B2 (en) | 1959-12-23 | 1960-12-22 | |
| DK507460AA DK106141C (en) | 1959-12-23 | 1960-12-22 | Process for the preparation of benzylguanidines or acid addition salts thereof. |
| CH1428160A CH410905A (en) | 1959-12-23 | 1960-12-22 | Process for the preparation of benzylguanidines |
| CH214466A CH486430A (en) | 1959-12-23 | 1960-12-22 | Process for the preparation of benzylguanidines |
| DEW29144A DE1288591B (en) | 1959-12-23 | 1960-12-22 | Process for the preparation of benzylguanidines |
| NL259381A NL128795C (en) | 1959-12-23 | 1960-12-23 | Process for the preparation of benzylguanidine derivatives and their acid addition salts |
| FR855866A FR1019M (en) | 1959-12-23 | 1961-03-16 | Hypotensive drug based on benzylguanidines. |
| MY1966101A MY6600101A (en) | 1959-12-23 | 1966-12-31 | Benzyl-guanidines, their preparation and pharmaceutical compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB43702/59A GB973882A (en) | 1959-12-23 | 1959-12-23 | Benzyl-guanidines,their preparation and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB973882A true GB973882A (en) | 1964-10-28 |
Family
ID=10429933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43702/59A Expired GB973882A (en) | 1959-12-23 | 1959-12-23 | Benzyl-guanidines,their preparation and pharmaceutical compositions containing them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB973882A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3352878A (en) * | 1965-03-18 | 1967-11-14 | Bristol Myers Co | Certain pyridylmethyl guanidine derivatives |
| FR2053005A1 (en) * | 1969-06-23 | 1971-04-16 | Wellcome Found | Substituted guanidines in cardiac treatment |
| DE1518230B1 (en) * | 1964-08-05 | 1972-10-26 | Wellcome Found | Process for the preparation of N-benzyl-N ', N "-dimethylguanidine |
| NL7806526A (en) * | 1977-06-17 | 1978-12-19 | Gea As | PROCESS FOR PREPARING SUBSTITUTED GUANIDINS. |
| DE3312516A1 (en) * | 1983-04-07 | 1984-10-11 | Brigitte Dr. 7400 Tübingen Pfeiffer | Nuclear-substituted phenylalkyleneguanidine derivatives, process for their preparation and pharmaceuticals containing them |
| EP1962892A2 (en) * | 2005-11-22 | 2008-09-03 | University of South Florida | Inhibition of cell proliferation |
| JP2017513948A (en) * | 2014-04-17 | 2017-06-01 | イミューノメット セラピューティクス インコーポレイテッド | Guanidine compounds and uses thereof |
-
1959
- 1959-12-23 GB GB43702/59A patent/GB973882A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1518230B1 (en) * | 1964-08-05 | 1972-10-26 | Wellcome Found | Process for the preparation of N-benzyl-N ', N "-dimethylguanidine |
| US3352878A (en) * | 1965-03-18 | 1967-11-14 | Bristol Myers Co | Certain pyridylmethyl guanidine derivatives |
| FR2053005A1 (en) * | 1969-06-23 | 1971-04-16 | Wellcome Found | Substituted guanidines in cardiac treatment |
| NL7806526A (en) * | 1977-06-17 | 1978-12-19 | Gea As | PROCESS FOR PREPARING SUBSTITUTED GUANIDINS. |
| DE3312516A1 (en) * | 1983-04-07 | 1984-10-11 | Brigitte Dr. 7400 Tübingen Pfeiffer | Nuclear-substituted phenylalkyleneguanidine derivatives, process for their preparation and pharmaceuticals containing them |
| EP1962892A2 (en) * | 2005-11-22 | 2008-09-03 | University of South Florida | Inhibition of cell proliferation |
| EP1962892A4 (en) * | 2005-11-22 | 2011-10-12 | Univ South Florida | Inhibition of cell proliferation |
| US8642278B2 (en) | 2005-11-22 | 2014-02-04 | University Of South Florida | Inhibition of cell proliferation |
| US9656953B2 (en) | 2005-11-22 | 2017-05-23 | University Of South Florida | Inhibition of cell proliferation |
| JP2017513948A (en) * | 2014-04-17 | 2017-06-01 | イミューノメット セラピューティクス インコーポレイテッド | Guanidine compounds and uses thereof |
| US11465989B2 (en) | 2014-04-17 | 2022-10-11 | ImmunoMet Therapeutics, Inc. | Guanidine compounds and use thereof |
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