GB599714A - Manufacture of biguanide derivatives - Google Patents
Manufacture of biguanide derivativesInfo
- Publication number
- GB599714A GB599714A GB2615845A GB2615845A GB599714A GB 599714 A GB599714 A GB 599714A GB 2615845 A GB2615845 A GB 2615845A GB 2615845 A GB2615845 A GB 2615845A GB 599714 A GB599714 A GB 599714A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- methyl
- bromo
- isopropyl
- iodo
- 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
- 150000004283 biguanides Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000004982 aromatic amines Chemical class 0.000 abstract 3
- QGBSISYHAICWAH-UHFFFAOYSA-N cyanoguanidine Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 3
- 150000003840 hydrochlorides Chemical class 0.000 abstract 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 abstract 2
- -1 methyl- Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 abstract 2
- TWCOVVFBNPAJQA-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-methyl-2-(N'-propan-2-ylcarbamimidoyl)guanidine Chemical compound CC(C)N=C(N)\N=C(/N)N(C)C1=CC=C(Cl)C=C1 TWCOVVFBNPAJQA-UHFFFAOYSA-N 0.000 abstract 1
- FVZODFVCIDBDGS-UHFFFAOYSA-N 3-bromo-4-chloroaniline Chemical compound NC1=CC=C(Cl)C(Br)=C1 FVZODFVCIDBDGS-UHFFFAOYSA-N 0.000 abstract 1
- LDSIOPGMLLPSSR-UHFFFAOYSA-N 3-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C(Cl)=C1 LDSIOPGMLLPSSR-UHFFFAOYSA-N 0.000 abstract 1
- AWJWTZAGRWNBFC-UHFFFAOYSA-N 4-chloro-3-iodoaniline Chemical compound NC1=CC=C(Cl)C(I)=C1 AWJWTZAGRWNBFC-UHFFFAOYSA-N 0.000 abstract 1
- FOHHWGVAOVDVLP-UHFFFAOYSA-N 4-chloro-3-nitroaniline Chemical compound NC1=CC=C(Cl)C([N+]([O-])=O)=C1 FOHHWGVAOVDVLP-UHFFFAOYSA-N 0.000 abstract 1
- MOZUAEZOXSBOQL-UHFFFAOYSA-N BrC1=CC=C(C=C1)NC(=N)NC(=N)NCC Chemical compound BrC1=CC=C(C=C1)NC(=N)NC(=N)NCC MOZUAEZOXSBOQL-UHFFFAOYSA-N 0.000 abstract 1
- ZETMMWSQPJGDAO-UHFFFAOYSA-N C1(=CC=C(C=C1)OCC)NC(=N)NC(=NC(C)C)NCCCC Chemical compound C1(=CC=C(C=C1)OCC)NC(=N)NC(=NC(C)C)NCCCC ZETMMWSQPJGDAO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003430 antimalarial agent Substances 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000001264 neutralization Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Biguanide derivatives of the general formula <FORM:0599714/IV/1> wherein A represents an aryl radical which may bear one or more neutral or basic substituents, R represents an alkyl or p cycloalkyl radical and R1 hydrogen or an alkyl or cycloalkyl radical, or R and R1 form, with the adjacent nitrogen atom, a heterocyclic ring, X represents hydrogen or an alkyl or cycloalkyl radical, but either R1 or X is always hydrogen, and R11 represents hydrogen or an alkyl radical, are manufactured by the interaction of a substituted dicyandiamide <FORM:0599714/IV/2> with an arylamine ANHR11, e.g. by heating the substituted dicyandiamide with a salt of the arylamine in the presence of a solvent, e.g. water or b -ethoxyethanol. The products are useful as chemotherapeutic agents or intermediates therefor, those in which A is an aryl radical substituted by at least one halogen atom in m- or p-position to the nitrogen atom and in which R, R1 and X together contain more than one and fewer than 8 carbon atoms being particularly suitable as antimalarial agents. In examples, the following compounds, in most cases in the form of their hydrochlorides, are prepared from the appropriate dicyandiamide derivatives and the hydrochlorides of the appropriate arylamines: (N1-phenyl-, N1-o-, -m- and -p-chloro-, -p-bromo-, -2 5 -, -2 : 3-, -2 : 5-, -2 : 6-, and -3 : 4- and 3 : 5-dichloro-, -p-methylthiol-, -p-31 : 51-dimethylphenoxy-, -p-odo-, -4-chloro-2-methyl-, -3-chloro-4-methyl-, -4-chloro-3-methyl-, -p-fluoro-, -p-nitro-, -m-and -p-cyano-, -3-chloro-4-bromo-, -3-chloro-4-iodo- and -3 : 4 : 5-trichloro-phenyl-, N1-6-bromo - 2 - naphthyl-, N1 - p - phenetyl-, N1-(diphenyl-4)- and N1-o-, -m- and -p-tolyl-N5-isopropylbiguanide; N1-p-tolyl- and N1-p-bromophenyl-N5-ethylbiguanide; N1-p-chlorophenyl-N1 - methyl - N5 - isopropylbiguanide; N1-o-, -m- and -p-chloro-, -p-nitro-, -p-cyano- and -p-iodo - phenyl - N5 - methyl - N5 - isopropylbiguanide; N1 - p - chlorophenyl - N5 : N5-cyclopentamethylenebiguanide; N1-m- and -p-chlorophenyl-N5 : N5-diethylbiguanide; N4 : N5-di-isopropyl-, N4-ethyl-N5-isopropyl-N4 - n - proyl - N5 - isopropyl-, N4 : N5-di-, methyl-, N4-methyl-N5-ethyl-, N4-methyl-N5-n-, butyl-, N4 - isopropyl - N5 - cyclohexyl-, and N5 - isobutyl - H1 - p - chlorophenylbiguanide; and N1 - p - phenetyl - N4 - isopropyl - N5 - n - butylbiguanide. Additional starting materials specified are, on the one hand, N3-n-propyl-N3-methyl-N3-n-propyl-, N3-ethyl-N3-n- and -isopropyl-, N3-methyl-N3-n-, -sec.- and -iso-butyl-, N3-sec.- and -tert.-butyl-, N3-n-amyl-, N2-methyl-N3-n- and -iso-propyl-, N2-methyl-N3-n-, -iso-, -sec.- and -tert.-butyl- and N2-ethyl-N3-n-propyl-, -butyl- and -amyl-dicyandiamide; and, on the other hand, m-bromo-, m-iodo-, 3 : 4-dibromo-, 3 : 4-diiodo-, 3-chloro-4-fluoro-, 3 : 5-dichloro-4-bromo-, 3 : 5-dichloro-4-iodo-, 3-iodo-4-chloro-, 3-bromo-4-chloro-, 4-chloro-3-nitro-and 3-chloro-4-nitroaniline. Specifications 599,713 and 599,722 are referred to.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CY7248A CY72A (en) | 1945-10-08 | 1948-09-02 | Manufacture of biguanide derivatives |
| MY5400009A MY5400009A (en) | 1945-10-08 | 1954-12-31 | Manufacture of biguanide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB599714A true GB599714A (en) | 1948-03-18 |
Family
ID=1739850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2615845A Expired GB599714A (en) | 1945-10-08 | 1945-10-08 | Manufacture of biguanide derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB599714A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3136816A (en) * | 1960-03-14 | 1964-06-09 | Sterling Drug Inc | 1-(lower alkylmercapto-chloro-phenyl) biguanides |
| US3272863A (en) * | 1964-03-27 | 1966-09-13 | Sterling Drug Inc | 1, 1'-(alkylene) bis |
| EP2742019A2 (en) * | 2011-08-08 | 2014-06-18 | Hanall Biopharma Co., Ltd. | N1-cyclic amine-n5-substituted phenyl biguanide derivatives, methods of preparing the same and pharmaceutical composition comprising the same |
| EP2941418A4 (en) * | 2013-02-07 | 2016-10-26 | N1-cyclic amine-n5-substituted biguanide derivatives, methods of preparing the same and pharmaceutical composition comprising the same | |
| CN110615886A (en) * | 2019-09-05 | 2019-12-27 | 哈尔滨工程大学 | Biguanide derivative antibacterial epoxy resin curing agent and preparation method thereof |
-
1945
- 1945-10-08 GB GB2615845A patent/GB599714A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3136816A (en) * | 1960-03-14 | 1964-06-09 | Sterling Drug Inc | 1-(lower alkylmercapto-chloro-phenyl) biguanides |
| US3272863A (en) * | 1964-03-27 | 1966-09-13 | Sterling Drug Inc | 1, 1'-(alkylene) bis |
| EP2742019A2 (en) * | 2011-08-08 | 2014-06-18 | Hanall Biopharma Co., Ltd. | N1-cyclic amine-n5-substituted phenyl biguanide derivatives, methods of preparing the same and pharmaceutical composition comprising the same |
| EP2742019A4 (en) * | 2011-08-08 | 2015-01-07 | Hanall Biopharma Co Ltd | N1-cyclic amine-n5-substituted phenyl biguanide derivatives, methods of preparing the same and pharmaceutical composition comprising the same |
| US9540325B2 (en) | 2011-08-08 | 2017-01-10 | ImmunoMet Therapeutics, Inc. | N1-cyclic amine-N5-substituted phenyl biguanide derivatives, methods of preparing the same and pharmaceutical composition comprising the same |
| EP2941418A4 (en) * | 2013-02-07 | 2016-10-26 | N1-cyclic amine-n5-substituted biguanide derivatives, methods of preparing the same and pharmaceutical composition comprising the same | |
| US9884821B2 (en) | 2013-02-07 | 2018-02-06 | Immunomet Therapeutics Inc. | N1-cyclic amine-N5-substituted biguanide derivatives, methods of preparing the same and pharmaceutical composition comprising the same |
| US10252996B2 (en) | 2013-02-07 | 2019-04-09 | Immunomet Therapeutics Inc. | N1-cyclic amine-N5-substituted biguanide derivatives, methods of preparing the same and pharmaceutical composition comprising the same |
| CN110615886A (en) * | 2019-09-05 | 2019-12-27 | 哈尔滨工程大学 | Biguanide derivative antibacterial epoxy resin curing agent and preparation method thereof |
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