GB883282A - New guanidine compounds - Google Patents
New guanidine compoundsInfo
- Publication number
- GB883282A GB883282A GB19907/59A GB1990759A GB883282A GB 883282 A GB883282 A GB 883282A GB 19907/59 A GB19907/59 A GB 19907/59A GB 1990759 A GB1990759 A GB 1990759A GB 883282 A GB883282 A GB 883282A
- Authority
- GB
- United Kingdom
- Prior art keywords
- octahydro
- ethyl
- carbon atoms
- prepared
- azoninyl
- 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
- 150000002357 guanidines Chemical class 0.000 title 1
- -1 3 - (octahydro - 1 - azocinyl) - propyl- Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- FECTVPHSLDTRBX-UHFFFAOYSA-N 2-[2-(azonan-1-yl)ethyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.N1(CCCCCCCC1)CCNC(=N)N FECTVPHSLDTRBX-UHFFFAOYSA-N 0.000 abstract 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- RMKNXMDTASPYBG-UHFFFAOYSA-N N1(CCCCCCCC1)CCN Chemical compound N1(CCCCCCCC1)CCN RMKNXMDTASPYBG-UHFFFAOYSA-N 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 239000012752 auxiliary agent Substances 0.000 abstract 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 abstract 1
- NRHDCQLCSOWVTF-UHFFFAOYSA-N azonane Chemical compound C1CCCCNCCC1 NRHDCQLCSOWVTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 229960002715 nicotine Drugs 0.000 abstract 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises alkyleneiminoalkylguanidines in which the alkyleneimino ring contains from 4 to 10 carbon atoms and the alkyl radical contains from 1 to 7 carbon atoms, acyl derivatives thereof and also their physiologically tolerable acid addition and quaternary ammonium salts. The guanidino group is preferably unsubstituted, but may bear lower hydrocarbon radicals on the nitrogen atoms. Acyl derivates may be formed with organic acids (many listed), including acetic, trifluoroacetic, hydroxyacetic acrylic, aminobenzoic, nicotine and 2-furoic acid. The compounds are prepared by reacting an alkyleneimino alkylamine with an S-alkyl isothiourea or a salt thereof, preferably in the presence of a solvent. Examples detail the preparation of 2-(octahydro-1-azoninyl)-ethyl-guanidine sulphate and 3 - (octahydro - 1 - azocinyl) - propyl-, 2 - (hexahydro - 1 - azepinyl) - ethyl-, 2-(piperidino) ethyl- and 2-(decamethyleneimino) ethyl guanidine sulphate. 2-(Octahydro-1-azoninyl)-ethylamine is prepared by lithium aluminium hydride reduction of octahydro - 1 - azoninyl - acetonitrile itself formed from chloracetonitrile and octahydro-azonine. 3 - (Octahydro - 1 - azocinyl) - propylamino is prepared from octahydro-azocine via octa-hydro-1-azocinyl-propionitrile. The other starting materials are likewise prepared. Specification 883,283 is referred to.ALSO:Hypotensive compositions comprise alkyleneiminoalkylguanidines (in which the alkyleneimino ring contains from 4 to 10 carbon atoms and the alkyl radical contains from 1 to 7 carbon atoms), their N-acyl derivatives, and/or their physiologically tolerable acid addition or quaternary ammonium salts, together with a suitable carrier for enteral, particularly oral, or parenteral administration. The compositions may be in the form of tablets, dragees, capsules, solutions, suspensions or emulsions and may incorporate auxiliary agents or other therapeutic compounds.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74102058A | 1958-06-10 | 1958-06-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB883282A true GB883282A (en) | 1961-11-29 |
Family
ID=24979033
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19907/59A Expired GB883282A (en) | 1958-06-10 | 1959-06-10 | New guanidine compounds |
| GB37788/59A Expired GB883283A (en) | 1958-06-10 | 1959-06-10 | A new guanidine compound |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37788/59A Expired GB883283A (en) | 1958-06-10 | 1959-06-10 | A new guanidine compound |
Country Status (5)
| Country | Link |
|---|---|
| CY (1) | CY255A (en) |
| FR (2) | FR221M (en) |
| GB (2) | GB883282A (en) |
| MY (1) | MY6300008A (en) |
| OA (1) | OA01798A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2531089B1 (en) * | 1982-07-27 | 1986-03-21 | Pharmascience Lab | NOVEL OESTRANIC DERIVATIVES FOR TOPICAL PHARMACOLOGICAL APPLICATIONS AND THEIR PREPARATION METHOD |
-
1959
- 1959-06-10 GB GB19907/59A patent/GB883282A/en not_active Expired
- 1959-06-10 GB GB37788/59A patent/GB883283A/en not_active Expired
-
1960
- 1960-08-19 FR FR836203A patent/FR221M/en not_active Expired
-
1961
- 1961-08-24 FR FR836565A patent/FR307M/en not_active Expired
-
1962
- 1962-12-03 CY CY25562A patent/CY255A/en unknown
-
1963
- 1963-12-31 MY MY19638A patent/MY6300008A/en unknown
-
1965
- 1965-08-20 OA OA52154A patent/OA01798A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY6300008A (en) | 1963-12-31 |
| CY255A (en) | 1962-12-03 |
| FR221M (en) | 1961-02-27 |
| GB883283A (en) | 1961-11-29 |
| OA01798A (en) | 1970-01-14 |
| FR307M (en) | 1961-03-20 |
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