ES419721A1 - Phenylguanidine derivatives their production and their medicinal use - Google Patents
Phenylguanidine derivatives their production and their medicinal useInfo
- Publication number
- ES419721A1 ES419721A1 ES419721A ES419721A ES419721A1 ES 419721 A1 ES419721 A1 ES 419721A1 ES 419721 A ES419721 A ES 419721A ES 419721 A ES419721 A ES 419721A ES 419721 A1 ES419721 A1 ES 419721A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- alkyl
- halogen
- molecular weight
- alkoxy
- 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
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical class NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 17
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 229910052736 halogen Inorganic materials 0.000 abstract 10
- 125000003545 alkoxy group Chemical group 0.000 abstract 9
- 125000005843 halogen group Chemical group 0.000 abstract 8
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002541 isothioureas Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- -1 phenoxy, phenoxy halogen Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
Abstract
Procedure for the production of phenylguanidine derivatives of the formula ** (See formula) ** where X is an alkyl radical with 1 to 6 carbon atoms, R1 is an alkyl radical with 1 to 4 carbon atoms, R2 is hydrogen or alkyl with 1 to 18 carbon atoms (optionally substituted by halogen, cyano, alkoxy with 1 to 4 carbon atoms, 2 to 5 carbon alkoxycarbonyl, phenoxy, phenoxy halogen, alkylphenoxy, alkoxyphenoxy), with the limitation that X, R1 and R2 must not simultaneously represent methyl; in addition, cycloalkyl with 5 to 8 carbon atoms, aralkyl (optionally substituted by halogen, alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms), aryl (optionally substituted by halogen, alkyl with 1 to 4 atoms) carbon or alkoxy with 1 to 4 carbon atoms), in addition, 1-furyl, with R2 also representing -NR'' R''', in which last formula R''is hydrogen or alkyl with 1 to 4 atoms of carbon, R'''is hydrogen or alkyl with 1 to 18 carbon atoms, the alkyl radical possibly being substituted by halogen, cyano, alkoxy with up to 4 carbon atoms, alkoxycarbonyl with up to 5 carbon atoms; in addition, cycloalkyl with 5 to 8 carbon atoms, aralkyl (which may optionally be substituted in the aryl part by halogen, low molecular weight alkyl and/or low molecular weight alkoxy), phenyl (optionally substituted by halogen, low alkyl molecular weight and/or low molecular weight alkoxy), acyl with 18 carbon atoms (possibly substituted by halogen, low molecular weight alkoxy), clay (possibly substituted by halogen, low molecular weight alkyl, low molecular weight alkoxy), alkylsulfonyl with up to 18 carbon atoms, arylsulfonyl (optionally substituted by halogen, amino, low molecular weight alkyl, low molecular weight alkoxy) and dialkylamino with up to 4 carbon atoms; in addition, R'' and R'''can together with the connecting nitrogen atom also represent a heterocyclic ring with 4 to 7 carbon atoms, the ring still possibly containing oxygen or sulfur as further heteroatoms; characterized in that 2-aminoaniline derivatives of the formula in which X and R2 have the meanings indicated above, are reacted with isothiourea derivatives of the formula ** (See formula) ** in which R1 has the meaning defined above and R represents alkyl with 1 to 4 carbon atoms, in the presence of a diluent and optionally in the presence of an organic or inorganic acid, at temperatures from 50 to 120ºC, preferably from 60 to 100ºC. (Machine-translation by Google Translate, not legally binding)
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 (1)
| Publication Number | Publication Date |
|---|---|
| ES419721A1 true ES419721A1 (en) | 1976-03-01 |
Family
ID=5859304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES419721A Expired ES419721A1 (en) | 1972-10-18 | 1973-10-17 | Phenylguanidine derivatives their production and their medicinal use |
Country Status (23)
| Country | Link |
|---|---|
| JP (2) | JPS4986341A (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 LU LU68627A patent/LU68627A1/xx unknown
- 1973-10-16 EG EG403A patent/EG11195A/en active
- 1973-10-16 JP JP48115396A patent/JPS4986341A/ja active Pending
- 1973-10-16 JP JP48115397A patent/JPS4971123A/ja active Pending
- 1973-10-16 AT AT878973A patent/AT338818B/en not_active IP Right Cessation
- 1973-10-16 CS CS7129A patent/CS168049B2/cs unknown
- 1973-10-16 CH CH1465073A patent/CH586195A5/xx not_active IP Right Cessation
- 1973-10-16 AR AR250542A patent/AR199121A1/en active
- 1973-10-17 PH PH15116A patent/PH10760A/en unknown
- 1973-10-17 IE IE1854/73A patent/IE38387B1/en unknown
- 1973-10-17 AU AU61505/73A patent/AU475701B2/en not_active Expired
- 1973-10-17 ES ES419721A patent/ES419721A1/en not_active Expired
- 1973-10-17 BE BE136796A patent/BE806201A/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 SE SE7314109A patent/SE386436B/en unknown
- 1973-10-17 ZA ZA738075*A patent/ZA738075B/en unknown
- 1973-10-18 HU HUBA2987A patent/HU166358B/hu unknown
- 1973-10-18 FR FR7337211A patent/FR2203631B1/fr not_active Expired
-
1976
- 1976-05-18 KE KE2628*UA patent/KE2628A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4971123A (en) | 1974-07-10 |
| IL43431A0 (en) | 1974-01-14 |
| FR2203631A1 (en) | 1974-05-17 |
| JPS4986341A (en) | 1974-08-19 |
| IE38387B1 (en) | 1978-03-01 |
| KE2628A (en) | 1976-05-28 |
| ATA878973A (en) | 1977-01-15 |
| SE386436B (en) | 1976-08-09 |
| IL43431A (en) | 1976-04-30 |
| GB1414244A (en) | 1975-11-19 |
| SU489315A3 (en) | 1975-10-25 |
| IE38387L (en) | 1974-04-18 |
| AR199121A1 (en) | 1974-08-08 |
| DE2250911A1 (en) | 1974-04-25 |
| LU68627A1 (en) | 1973-12-27 |
| AU475701B2 (en) | 1976-09-02 |
| NL7314183A (en) | 1974-04-22 |
| CA992554A (en) | 1976-07-06 |
| AT338818B (en) | 1977-09-12 |
| CS168049B2 (en) | 1976-05-28 |
| HU166358B (en) | 1975-03-28 |
| ZA738075B (en) | 1974-08-28 |
| BE806201A (en) | 1974-04-17 |
| EG11195A (en) | 1977-11-30 |
| AU6150573A (en) | 1975-04-17 |
| PH10760A (en) | 1977-09-02 |
| CH586195A5 (en) | 1977-03-31 |
| FR2203631B1 (en) | 1977-09-09 |
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