IL43431A - N-(5-alkyl-2-amidophenyl)-n',n"-bis-(alkoxycarbonyl)-guanidines,their production and pharmaceutical compositions containing them - Google Patents
N-(5-alkyl-2-amidophenyl)-n',n"-bis-(alkoxycarbonyl)-guanidines,their production and pharmaceutical compositions containing themInfo
- Publication number
- IL43431A IL43431A IL43431A IL4343173A IL43431A IL 43431 A IL43431 A IL 43431A IL 43431 A IL43431 A IL 43431A IL 4343173 A IL4343173 A IL 4343173A IL 43431 A IL43431 A IL 43431A
- Authority
- IL
- Israel
- Prior art keywords
- compound according
- hereinbefore described
- diluent
- radical
- admixture
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 19
- 238000000034 method Methods 0.000 claims 11
- 239000003085 diluting agent Substances 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- -1 alkyl radical Chemical class 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 206010061217 Infestation Diseases 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- ULOIAOPTGWSNHU-UHFFFAOYSA-N 2-butyl radical Chemical group C[CH]CC ULOIAOPTGWSNHU-UHFFFAOYSA-N 0.000 claims 1
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical class NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 241001465677 Ancylostomatoidea Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000001117 sulphuric acid Substances 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
-
- 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
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
Claims (27)
1. Compounds which are phenylguanidine derivatives following general formula in which X is an n-butyl radical; R^" is an alkyl radical with 1 to 4 carbon atoms; 2 R is an alkyl radical with 1 to 4 carbon atoms, a cyclohexyl radical, a phenyl radical or a (C-^-C^) alkylamino or a (C^-C^) alkoxy- (C^-C^) alkylamino. radical.
2. Compounds according to Claim 1 in which R1 is a methyl, ethyl, isopropyl or sec-butyl radical.
3. The compound according to Claim 1 that is hereinbefore described in Example 1.
4. The compound according to Claim 1 that is hereinbefore described in Example 2.
5. The compound according to Claim 1 that is hereinbefore described in Example 4.
6. The compound according to Claim 1 that is hereinbefore described in Example 5.
7. The compound according to Claim 1 that is hereinbefore described in Example 7.
8. The compound according to Claim 1 that is hereinbefore described in Example 8.
9. Compounds according to Claim 1 that are hereinbefore specifically mentioned other than those according to Claims
10. A process for the production of a compound according any of claims 1 to 9-·, in which a 2-a.minoaniline derivative of the general formula: - is reacted with an isothiourea of the general formula :- [in which general formulae X, R and R are as defined in any of Claims 1 to 4 and R is an alkyl radical with 1 to 4 carbon atoms] .
11. A process according to Claim 10 in which the reaction is carried out in a polar organic solvent as diluent.
12. A process according to Claim 10 or 11 in which the reaction is carried out in the presence of hydrochloric acid, sulphuric acid, nitric acid, formic acid, acetic acid, or p_-toluenesulphonic acid:
13. A process according to Claim 10, H or 12 in which the reaction is carried out at 60 to 100°C.
14. A process for the production of a compound according to any of Claims 1 to 9 substantially as hereinbefore described in Example 1.
15. Compounds according to Claim 1 whenever produced by a process according to any of Claims 10 to 14.
16. A pharmaceutical composition containing as an active ingredient a compound according to any of Claims 1 to 9 and 15 in admixture with a solid or liquified gaseous diluent or in admixture ..with a liquid diluent other than a solvent of 43431/2 i
17. A pharmaceutical composition containing as an active ingredient a compound according to any of Claims 1 to 9 and 15 in the form of a sterile or isotonic aqueous solution.
18. A composition according to Claim 16 or 17 containing from 0.5 to 90 weight percent of active ingredient.
19. A pharmaceutical composition according to Claim 16, 17 or 18 substantially as hereinbefore described.
20. A medicament in dosage unit form comprising a compound according to any of Claims 1 to 9 and 15 either alone or in admixture with> a diluent.
21. A medicament in the form of tablets, pills, dragees, capsules, ampoules or suppositories comprising a compound according to any of Claims 1 to 9 and 15, either alone or in admixture with a diluent.
22. A medicament according to Claim .20 or 21 substantially as hereinbefore described.
23. A method of combatting helmintic infestation in non-human animals comprising administering to the animals an active compound according to any of Claims 1 to 9 and 15, either alone or in admixture with a diluent or in the form of a medicament according to Claim 20, 21 or 22.
24. A method according to Claim 23 in which the active compound is administered in an amount of 1 to 100 mg/kg body weight per day.
25. A method according to Claim 23 or 24 in which the active compound is administered perorally.
26. A method according to Claim 23, 24 or 25 in which the helmintic infestation is of hookworms, Tri~c hostrongylides , Strongylides , Rhabditides , eelworms or whipworms. i
27. A method according to any of Claims 23 to 26 substantially as hereinbefore described or as illustrated
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2250911A DE2250911A1 (en) | 1972-10-18 | 1972-10-18 | PHENYLGUANIDINE DERIVATIVES, A METHOD FOR THEIR PRODUCTION AND THEIR USE AS A MEDICINAL PRODUCT |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43431A0 IL43431A0 (en) | 1974-01-14 |
| IL43431A true IL43431A (en) | 1976-04-30 |
Family
ID=5859304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43431A IL43431A (en) | 1972-10-18 | 1973-10-16 | N-(5-alkyl-2-amidophenyl)-n',n"-bis-(alkoxycarbonyl)-guanidines,their production and pharmaceutical compositions containing them |
Country Status (23)
| Country | Link |
|---|---|
| JP (2) | JPS4971123A (en) |
| AR (1) | AR199121A1 (en) |
| AT (1) | AT338818B (en) |
| AU (1) | AU475701B2 (en) |
| BE (1) | BE806201A (en) |
| CA (1) | CA992554A (en) |
| CH (1) | CH586195A5 (en) |
| CS (1) | CS168049B2 (en) |
| DE (1) | DE2250911A1 (en) |
| EG (1) | EG11195A (en) |
| ES (1) | ES419721A1 (en) |
| FR (1) | FR2203631B1 (en) |
| GB (1) | GB1414244A (en) |
| HU (1) | HU166358B (en) |
| IE (1) | IE38387B1 (en) |
| IL (1) | IL43431A (en) |
| KE (1) | KE2628A (en) |
| LU (1) | LU68627A1 (en) |
| NL (1) | NL7314183A (en) |
| PH (1) | PH10760A (en) |
| SE (1) | SE386436B (en) |
| SU (1) | SU489315A3 (en) |
| ZA (1) | ZA738075B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2651467A1 (en) * | 1976-11-11 | 1978-05-18 | Bayer Ag | SUBSTITUTED O-PHENYLENE DIAMINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
| US6593466B1 (en) | 1999-07-07 | 2003-07-15 | Isis Pharmaceuticals, Inc. | Guanidinium functionalized nucleotides and precursors thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2108835A1 (en) * | 1970-10-09 | 1972-05-26 | Rhone Poulenc Sa | Fungicidal guanidines from o phenylenediamine |
| DE2109454A1 (en) * | 1971-02-27 | 1972-09-14 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Fungicidal n-(2-acylaminophenyl)-n,n-bis(alkoxycarbonyl)-guanidines - from 2-acrylaminoanilines and s-alkyl n,n-bis(alkoxycarbonyl) isothiazole |
-
1972
- 1972-10-18 DE DE2250911A patent/DE2250911A1/en active Pending
-
1973
- 1973-10-12 SU SU1963844A patent/SU489315A3/en active
- 1973-10-15 NL NL7314183A patent/NL7314183A/xx not_active Application Discontinuation
- 1973-10-16 IL IL43431A patent/IL43431A/en unknown
- 1973-10-16 JP JP48115397A patent/JPS4971123A/ja active Pending
- 1973-10-16 CS CS7129A patent/CS168049B2/cs unknown
- 1973-10-16 JP JP48115396A patent/JPS4986341A/ja active Pending
- 1973-10-16 AT AT878973A patent/AT338818B/en not_active IP Right Cessation
- 1973-10-16 LU LU68627A patent/LU68627A1/xx unknown
- 1973-10-16 EG EG403A patent/EG11195A/en active
- 1973-10-16 AR AR250542A patent/AR199121A1/en active
- 1973-10-16 CH CH1465073A patent/CH586195A5/xx not_active IP Right Cessation
- 1973-10-17 ZA ZA738075*A patent/ZA738075B/en unknown
- 1973-10-17 PH PH15116A patent/PH10760A/en unknown
- 1973-10-17 CA CA183,615A patent/CA992554A/en not_active Expired
- 1973-10-17 GB GB4838673A patent/GB1414244A/en not_active Expired
- 1973-10-17 ES ES419721A patent/ES419721A1/en not_active Expired
- 1973-10-17 AU AU61505/73A patent/AU475701B2/en not_active Expired
- 1973-10-17 IE IE1854/73A patent/IE38387B1/en unknown
- 1973-10-17 BE BE136796A patent/BE806201A/en unknown
- 1973-10-17 SE SE7314109A patent/SE386436B/en unknown
- 1973-10-18 FR FR7337211A patent/FR2203631B1/fr not_active Expired
- 1973-10-18 HU HUBA2987A patent/HU166358B/hu unknown
-
1976
- 1976-05-18 KE KE2628*UA patent/KE2628A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR199121A1 (en) | 1974-08-08 |
| AU475701B2 (en) | 1976-09-02 |
| FR2203631B1 (en) | 1977-09-09 |
| CA992554A (en) | 1976-07-06 |
| IE38387L (en) | 1974-04-18 |
| PH10760A (en) | 1977-09-02 |
| AT338818B (en) | 1977-09-12 |
| SU489315A3 (en) | 1975-10-25 |
| CS168049B2 (en) | 1976-05-28 |
| HU166358B (en) | 1975-03-28 |
| IE38387B1 (en) | 1978-03-01 |
| JPS4971123A (en) | 1974-07-10 |
| KE2628A (en) | 1976-05-28 |
| AU6150573A (en) | 1975-04-17 |
| LU68627A1 (en) | 1973-12-27 |
| GB1414244A (en) | 1975-11-19 |
| ES419721A1 (en) | 1976-03-01 |
| EG11195A (en) | 1977-11-30 |
| JPS4986341A (en) | 1974-08-19 |
| NL7314183A (en) | 1974-04-22 |
| ZA738075B (en) | 1974-08-28 |
| CH586195A5 (en) | 1977-03-31 |
| SE386436B (en) | 1976-08-09 |
| DE2250911A1 (en) | 1974-04-25 |
| ATA878973A (en) | 1977-01-15 |
| FR2203631A1 (en) | 1974-05-17 |
| IL43431A0 (en) | 1974-01-14 |
| BE806201A (en) | 1974-04-17 |
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