DE1793745A1 - Arylsubstituierte biguanide - Google Patents
Arylsubstituierte biguanideInfo
- Publication number
- DE1793745A1 DE1793745A1 DE19671793745 DE1793745A DE1793745A1 DE 1793745 A1 DE1793745 A1 DE 1793745A1 DE 19671793745 DE19671793745 DE 19671793745 DE 1793745 A DE1793745 A DE 1793745A DE 1793745 A1 DE1793745 A1 DE 1793745A1
- Authority
- DE
- Germany
- Prior art keywords
- acid addition
- biguanide
- addition salt
- chloro
- melting point
- 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.)
- Pending
Links
- 239000002253 acid Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- 229940123208 Biguanide Drugs 0.000 claims description 20
- -1 chloro-3-trifluoromethylphenyl biguanide Chemical compound 0.000 claims description 12
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 150000002825 nitriles Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000005187 foaming Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 150000001448 anilines Chemical class 0.000 description 4
- 150000004283 biguanides Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZFBKYGFPUCUYIF-UHFFFAOYSA-N 4-amino-2-chlorobenzonitrile Chemical compound NC1=CC=C(C#N)C(Cl)=C1 ZFBKYGFPUCUYIF-UHFFFAOYSA-N 0.000 description 2
- OREVCMGFYSUYPX-UHFFFAOYSA-N 4-amino-3-chlorobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1Cl OREVCMGFYSUYPX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDIITVHGZPTZOC-UHFFFAOYSA-N Cl.ClC=1C=C(C=CC1C#N)NC(=N)NC(=N)N Chemical compound Cl.ClC=1C=C(C=CC1C#N)NC(=N)NC(=N)N XDIITVHGZPTZOC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- WHNAMGUAXHGCHH-UHFFFAOYSA-N 1-nitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC(C(F)(F)F)=C1 WHNAMGUAXHGCHH-UHFFFAOYSA-N 0.000 description 1
- HTKSNWZVVNHTJJ-UHFFFAOYSA-N 2-(2-bromo-4-cyanophenyl)-1-(diaminomethylidene)guanidine hydrochloride Chemical compound Cl.BrC1=C(C=CC(=C1)C#N)NC(=N)NC(=N)N HTKSNWZVVNHTJJ-UHFFFAOYSA-N 0.000 description 1
- KDHYVTSTJSOINL-UHFFFAOYSA-N 2-(2-chloro-4-cyanophenyl)-1-(diaminomethylidene)guanidine hydrochloride Chemical compound Cl.ClC1=C(C=CC(=C1)C#N)NC(=N)NC(=N)N KDHYVTSTJSOINL-UHFFFAOYSA-N 0.000 description 1
- LDSIOPGMLLPSSR-UHFFFAOYSA-N 3-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C(Cl)=C1 LDSIOPGMLLPSSR-UHFFFAOYSA-N 0.000 description 1
- FDUGOYTWYJZNNP-UHFFFAOYSA-N 4-amino-2-fluorobenzonitrile Chemical compound NC1=CC=C(C#N)C(F)=C1 FDUGOYTWYJZNNP-UHFFFAOYSA-N 0.000 description 1
- RGHJWZADAWEIFE-UHFFFAOYSA-N 4-amino-2-methylbenzonitrile Chemical compound CC1=CC(N)=CC=C1C#N RGHJWZADAWEIFE-UHFFFAOYSA-N 0.000 description 1
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
- UTKUVRNVYFTEHF-UHFFFAOYSA-N 4-nitro-3-(trifluoromethyl)aniline Chemical compound NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 UTKUVRNVYFTEHF-UHFFFAOYSA-N 0.000 description 1
- VVDIMAMYKUTSCL-UHFFFAOYSA-N 5-amino-2-chlorobenzonitrile Chemical compound NC1=CC=C(Cl)C(C#N)=C1 VVDIMAMYKUTSCL-UHFFFAOYSA-N 0.000 description 1
- ASPDJZINBYYZRU-UHFFFAOYSA-N 5-amino-2-chlorobenzotrifluoride Chemical compound NC1=CC=C(Cl)C(C(F)(F)F)=C1 ASPDJZINBYYZRU-UHFFFAOYSA-N 0.000 description 1
- 101100286286 Dictyostelium discoideum ipi gene Proteins 0.000 description 1
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical class NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ARGDYOIRHYLIMT-UHFFFAOYSA-N n,n-dichloro-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N(Cl)Cl)C=C1 ARGDYOIRHYLIMT-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Structures Of Non-Positive Displacement Pumps (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3047966 | 1966-07-07 | ||
| GB19028/67A GB1194835A (en) | 1966-07-07 | 1966-07-07 | Novel 1-Amidino-3-Phenyl-Urea Derivatives, the preparation thereof and Compositions containing the same |
| GB5654666 | 1966-12-16 | ||
| GB539167 | 1967-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1793745A1 true DE1793745A1 (de) | 1973-05-30 |
Family
ID=27447446
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671793745 Pending DE1793745A1 (de) | 1966-07-07 | 1967-07-04 | Arylsubstituierte biguanide |
| DE19671668843 Pending DE1668843A1 (de) | 1966-07-07 | 1967-07-04 | Biologisch aktive substituierte Amidine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671668843 Pending DE1668843A1 (de) | 1966-07-07 | 1967-07-04 | Biologisch aktive substituierte Amidine |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US3539616A (enExample) |
| BE (1) | BE700895A (enExample) |
| CA (1) | CA947316A (enExample) |
| CH (5) | CH501598A (enExample) |
| DE (2) | DE1793745A1 (enExample) |
| DK (1) | DK125705B (enExample) |
| FR (2) | FR1548340A (enExample) |
| GB (1) | GB1194835A (enExample) |
| IL (1) | IL28189A (enExample) |
| LU (1) | LU54053A1 (enExample) |
| MC (1) | MC666A1 (enExample) |
| NL (1) | NL6709484A (enExample) |
| NO (1) | NO126225B (enExample) |
| OA (1) | OA02467A (enExample) |
| SE (1) | SE330010B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3761597A (en) * | 1967-06-30 | 1973-09-25 | L Walls | 1-amidino-3-(substituted-phenyl) urea antimalarial composition and method of use |
| IL37047A0 (en) * | 1970-06-30 | 1971-08-25 | Wellcome Found | Substituted amidines,their preparation and pharmaceutical compositions containing them |
| US4326074A (en) * | 1972-09-22 | 1982-04-20 | William H. Rorer, Inc. | Amidinoureas |
| US4488993A (en) * | 1972-09-22 | 1984-12-18 | William H. Rorer, Inc. | Amidinoureas |
| US4220658A (en) * | 1972-09-22 | 1980-09-02 | William H. Rorer, Inc. | Treatment of hypertension with amidinoureas |
| US4025652A (en) * | 1975-03-31 | 1977-05-24 | William H. Rorer, Inc. | Amidinoureas |
| FR2223361B1 (enExample) * | 1973-03-27 | 1977-04-29 | Philagro Sa | |
| JPS5646157B2 (enExample) * | 1973-06-05 | 1981-10-31 | ||
| US4060635A (en) * | 1975-03-31 | 1977-11-29 | William H. Rorer, Inc. | Amidinoureas for treating diarrhea |
| ZA743750B (en) * | 1973-07-16 | 1975-06-25 | Rorer Inc William H | Amindinoureas |
| US4150154A (en) * | 1975-03-03 | 1979-04-17 | William H. Rorer, Inc. | Amidinoureas |
| US4283555A (en) * | 1973-07-16 | 1981-08-11 | William H. Rorer, Inc. | Amidinoureas |
| US4216229A (en) * | 1973-07-16 | 1980-08-05 | William H. Rorer, Inc. | Method for treating gastrointestinal hyperacidity or ulceration with amidinoureas |
| FR2237625B1 (enExample) * | 1973-07-16 | 1978-07-28 | Rorer Inc William H | |
| US4216230A (en) * | 1973-07-16 | 1980-08-05 | William H. Rorer, Inc. | Method for alleviating hypertension with amidinoureas |
| US4204000A (en) * | 1975-03-31 | 1980-05-20 | William H. Rorer, Inc. | Anti-ulcer amidinoureas |
| US4203920A (en) * | 1975-03-31 | 1980-05-20 | William H. Rorer, Inc. | Amidinoureas |
| US4242337A (en) * | 1976-03-30 | 1980-12-30 | William H. Rorer, Inc. | Method for treatment of diarrheal disease conditions or symptons in mammals |
| US4242339A (en) * | 1976-03-30 | 1980-12-30 | William H. Rorer, Inc. | Method for treatment of gastrointestinal spasmodic disease conditions or symptoms in mammals |
| US4058557A (en) * | 1976-03-30 | 1977-11-15 | William H. Rorer, Inc. | Amidinoureas |
| US4353842A (en) * | 1978-09-14 | 1982-10-12 | William H. Rorer, Inc. | Amidinoureas |
| US4440949A (en) * | 1979-01-08 | 1984-04-03 | William H. Rorer, Inc. | Amidinoureas |
| US4340609A (en) * | 1980-01-02 | 1982-07-20 | William H. Rorer, Inc. | Amidinourea derivative veterinary compositions for suppression of parasitemia |
| NL8120313A (nl) * | 1981-08-24 | 1983-07-01 | Rorer Int Overseas | Heterocyclische amidino-gesubstitueerde ureums en de farmaceutische toepassingen daarvan. |
| JPS62501839A (ja) * | 1985-02-15 | 1987-07-23 | ロウラ− インタ−ナシヨナル（オ−バ−シ−ズ） インコ−ポレ−テツド | アミジノ尿素の製造法および医薬用組成物 |
| DE4412079A1 (de) * | 1993-08-18 | 1995-02-23 | Bayer Ag | N-Cyanoaryl-Stickstoffheterocyclen |
| US5681794A (en) * | 1993-08-18 | 1997-10-28 | Bayer Aktiengesellschaft | N-cyanoaryl-nitrogen heterocycles |
| EP0648749B1 (de) * | 1993-08-18 | 1997-12-10 | Bayer Ag | N-Cyanoaryl-Stickstoffheterocyclen |
| DE4335438A1 (de) * | 1993-10-18 | 1995-04-20 | Bayer Ag | 4-Cyanophenyliminoheterocyclen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3119867A (en) * | 1962-01-26 | 1964-01-28 | Clairol Inc | Amino, nitro-phenyl-biguanides and amino, nitro-phenyl; guanyl-ureas |
-
1966
- 1966-07-07 GB GB19028/67A patent/GB1194835A/en not_active Expired
-
1967
- 1967-06-22 CA CA993,746A patent/CA947316A/en not_active Expired
- 1967-06-23 IL IL28189A patent/IL28189A/en unknown
- 1967-06-29 SE SE09660/67*A patent/SE330010B/xx unknown
- 1967-06-30 US US650225A patent/US3539616A/en not_active Expired - Lifetime
- 1967-07-04 NO NO00168928A patent/NO126225B/no unknown
- 1967-07-04 OA OA52998A patent/OA02467A/xx unknown
- 1967-07-04 BE BE700895D patent/BE700895A/xx unknown
- 1967-07-04 DE DE19671793745 patent/DE1793745A1/de active Pending
- 1967-07-04 DE DE19671668843 patent/DE1668843A1/de active Pending
- 1967-07-05 FR FR1548340D patent/FR1548340A/fr not_active Expired
- 1967-07-06 MC MC705A patent/MC666A1/fr unknown
- 1967-07-06 DK DK349067AA patent/DK125705B/da unknown
- 1967-07-07 CH CH324870A patent/CH501598A/de not_active IP Right Cessation
- 1967-07-07 CH CH325170A patent/CH554318A/xx not_active IP Right Cessation
- 1967-07-07 NL NL6709484A patent/NL6709484A/xx unknown
- 1967-07-07 CH CH966767A patent/CH501597A/de not_active IP Right Cessation
- 1967-07-07 CH CH1705770A patent/CH501599A/de not_active IP Right Cessation
- 1967-07-07 CH CH325070A patent/CH500952A/de not_active IP Right Cessation
- 1967-07-07 LU LU54053D patent/LU54053A1/xx unknown
- 1967-10-03 FR FR123107A patent/FR7055M/fr not_active Expired
-
1970
- 1970-06-30 US US00051325A patent/US3784582A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR7055M (enExample) | 1969-06-23 |
| MC666A1 (fr) | 1968-04-01 |
| DE1668843A1 (de) | 1972-02-24 |
| CH501597A (de) | 1971-01-15 |
| CH500952A (de) | 1970-12-31 |
| US3784582A (en) | 1974-01-08 |
| CA947316A (en) | 1974-05-14 |
| NL6709484A (enExample) | 1968-01-08 |
| BE700895A (enExample) | 1968-01-04 |
| NO126225B (enExample) | 1973-01-08 |
| US3539616A (en) | 1970-11-10 |
| DK125705B (da) | 1973-03-26 |
| OA02467A (fr) | 1970-05-05 |
| LU54053A1 (enExample) | 1968-03-12 |
| IL28189A (en) | 1971-04-28 |
| SE330010B (enExample) | 1970-11-02 |
| GB1194835A (en) | 1970-06-10 |
| CH501598A (de) | 1971-01-15 |
| CH501599A (de) | 1971-01-15 |
| CH554318A (de) | 1974-09-30 |
| FR1548340A (enExample) | 1968-12-06 |
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