DE2117015A1 - 1,2-Biguanide - Google Patents
1,2-BiguanideInfo
- Publication number
- DE2117015A1 DE2117015A1 DE19712117015 DE2117015A DE2117015A1 DE 2117015 A1 DE2117015 A1 DE 2117015A1 DE 19712117015 DE19712117015 DE 19712117015 DE 2117015 A DE2117015 A DE 2117015A DE 2117015 A1 DE2117015 A1 DE 2117015A1
- Authority
- DE
- Germany
- Prior art keywords
- nitrate
- biguanide
- ethyl
- hydrochloride
- methyl
- 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.)
- Withdrawn
Links
- 229940123208 Biguanide Drugs 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229910002651 NO3 Inorganic materials 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 19
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 17
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 16
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- -1 1-Ethyl Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- AVWOEAVWVDLXMA-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;nitric acid Chemical compound O[N+]([O-])=O.NC(N)=NC(N)=N AVWOEAVWVDLXMA-UHFFFAOYSA-N 0.000 claims description 8
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 8
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 8
- 150000004283 biguanides Chemical class 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 3
- 229960004111 buformin Drugs 0.000 claims description 3
- 150000001718 carbodiimides Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- OMMCFRQMHYABIP-UHFFFAOYSA-N 1-(diaminomethylidene)-2-ethyl-3-propan-2-ylguanidine;hydroiodide Chemical compound I.CCN=C(NC(C)C)N=C(N)N OMMCFRQMHYABIP-UHFFFAOYSA-N 0.000 claims description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- UUBZPMKBMHXGNE-UHFFFAOYSA-N 1-(diaminomethylidene)-2-naphthalen-1-ylguanidine Chemical compound C1=CC=C2C(N=C(N)N=C(N)N)=CC=CC2=C1 UUBZPMKBMHXGNE-UHFFFAOYSA-N 0.000 claims 1
- UPJMYILFLDLYNH-UHFFFAOYSA-N 2-cyclopropyl-1-(diaminomethylidene)guanidine Chemical compound NC(=N)NC(=N)NC1CC1 UPJMYILFLDLYNH-UHFFFAOYSA-N 0.000 claims 1
- 229940127003 anti-diabetic drug Drugs 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 72
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
- 238000002844 melting Methods 0.000 description 46
- 230000008018 melting Effects 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229960004198 guanidine Drugs 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- 229960000789 guanidine hydrochloride Drugs 0.000 description 5
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 229910001961 silver nitrate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical class CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- DJAVXQJRIAKWOA-UHFFFAOYSA-N carbonic acid;1-(diaminomethylidene)-3-methylthiourea Chemical compound OC(O)=O.CNC(=S)NC(N)=N DJAVXQJRIAKWOA-UHFFFAOYSA-N 0.000 description 3
- JWIIKQOYFDABEW-UHFFFAOYSA-N carbonic acid;thiourea Chemical compound NC(N)=S.OC(O)=O JWIIKQOYFDABEW-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 3
- 229960003243 phenformin Drugs 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- VJROPLWGFCORRM-UHFFFAOYSA-N 2-methylbutan-1-amine Chemical compound CCC(C)CN VJROPLWGFCORRM-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 102000006835 Lamins Human genes 0.000 description 2
- 108010047294 Lamins Proteins 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 2
- LIMQQADUEULBSO-UHFFFAOYSA-N butyl isothiocyanate Chemical compound CCCCN=C=S LIMQQADUEULBSO-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 210000005053 lamin Anatomy 0.000 description 2
- 229910000474 mercury oxide Inorganic materials 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- BWBKOTRFVFLABK-UHFFFAOYSA-N 1,2-dibutyl-3-(diaminomethylidene)guanidine;hydrochloride Chemical compound Cl.CCCCNC(NC(N)=N)=NCCCC BWBKOTRFVFLABK-UHFFFAOYSA-N 0.000 description 1
- KREOCUNMMFZOOS-UHFFFAOYSA-N 1,3-di(propan-2-yl)thiourea Chemical compound CC(C)NC(S)=NC(C)C KREOCUNMMFZOOS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FNMJZTGQHUXSHY-UHFFFAOYSA-N 1-(diaminomethylidene)-3-ethyl-2-methylguanidine;nitric acid Chemical compound O[N+]([O-])=O.CCNC(=NC)N=C(N)N FNMJZTGQHUXSHY-UHFFFAOYSA-N 0.000 description 1
- SPLJCDGYZTYQQY-UHFFFAOYSA-N 1-(diaminomethylidene)-3-methylthiourea Chemical compound CNC(=S)NC(N)=N SPLJCDGYZTYQQY-UHFFFAOYSA-N 0.000 description 1
- JRRKOULJUFBLEZ-UHFFFAOYSA-N 1-carbamimidoyl-1-methylthiourea Chemical compound NC(=N)N(C)C(N)=S JRRKOULJUFBLEZ-UHFFFAOYSA-N 0.000 description 1
- PCAUSEZGTJUFRH-UHFFFAOYSA-N 1-cyano-3-ethyl-2-methylguanidine Chemical compound CCN=C(NC)NC#N PCAUSEZGTJUFRH-UHFFFAOYSA-N 0.000 description 1
- ULFNAOHBWGRYLW-UHFFFAOYSA-N 1-cyclononylazonane Chemical compound C1CCCCCCCC1N1CCCCCCCC1 ULFNAOHBWGRYLW-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- KREZRKULMRIOKR-UHFFFAOYSA-N 2-butyl-1-(diaminomethylidene)-3-ethylguanidine Chemical compound CCCCN=C(NCC)N=C(N)N KREZRKULMRIOKR-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VPRIGCVCJPKVFZ-UHFFFAOYSA-N 4-chloro-n-phenylaniline Chemical compound C1=CC(Cl)=CC=C1NC1=CC=CC=C1 VPRIGCVCJPKVFZ-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- IEDBTSYRKOBFMZ-UHFFFAOYSA-N CCCCNC([S+](C)CCCC)=N.Cl Chemical compound CCCCNC([S+](C)CCCC)=N.Cl IEDBTSYRKOBFMZ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910052946 acanthite Inorganic materials 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- FJMAIXOJSFLKEM-UHFFFAOYSA-N carbonic acid;1-(diaminomethylidene)-3-ethylthiourea Chemical compound OC(O)=O.CCNC(=S)NC(N)=N FJMAIXOJSFLKEM-UHFFFAOYSA-N 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XZLAHQGYFIXGJK-UHFFFAOYSA-N n-diaminophosphorylethanamine Chemical compound CCNP(N)(N)=O XZLAHQGYFIXGJK-UHFFFAOYSA-N 0.000 description 1
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- XUARKZBEFFVFRG-UHFFFAOYSA-N silver sulfide Chemical compound [S-2].[Ag+].[Ag+] XUARKZBEFFVFRG-UHFFFAOYSA-N 0.000 description 1
- 229940056910 silver sulfide Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- VOXVCYMHFQQEMC-UHFFFAOYSA-O triethylazanium;nitrate Chemical compound [O-][N+]([O-])=O.CC[NH+](CC)CC VOXVCYMHFQQEMC-UHFFFAOYSA-O 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C1/00—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design
- A61C1/02—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design characterised by the drive of the dental tools
- A61C1/05—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design characterised by the drive of the dental tools with turbine drive
- A61C1/057—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design characterised by the drive of the dental tools with turbine drive with means for preventing suction effect in turbine after deactivation of the drive air
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dentistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712117015 DE2117015A1 (de) | 1971-04-02 | 1971-04-02 | 1,2-Biguanide |
| CS6964*A CS161937B2 (cs) | 1971-04-02 | 1972-03-15 | |
| CS1724A CS161935B2 (cs) | 1971-04-02 | 1972-03-15 | |
| CS6963*A CS161936B2 (cs) | 1971-04-02 | 1972-03-15 | |
| DK134572AA DK129651B (da) | 1971-04-02 | 1972-03-22 | Analogifremgangsmåde til fremstilling af biguanider eller syreadditionssalte deraf. |
| ES401124A ES401124A1 (es) | 1971-04-02 | 1972-03-23 | Procedimiento para la preparacion de biguanidas sustitui- das. |
| GB1416272A GB1386130A (en) | 1971-04-02 | 1972-03-27 | 1,2-biguanides |
| CH454672A CH579534A5 (cs) | 1971-04-02 | 1972-03-27 | |
| AR241248A AR194360A1 (es) | 1971-04-02 | 1972-03-29 | Procedimiento para la preparacion de biguanidas 1,2-sustituidas |
| NO1084/72A NO135418C (cs) | 1971-04-02 | 1972-03-29 | |
| SE7204127A SE377332B (cs) | 1971-04-02 | 1972-03-29 | |
| ZA722183A ZA722183B (en) | 1971-04-02 | 1972-03-30 | 1,2-biguanides |
| AU40661/72A AU468307B2 (en) | 1971-04-02 | 1972-03-30 | 1, 2-biguanides |
| AT279272A AT313301B (de) | 1971-04-02 | 1972-03-30 | Verfahren zur Herstellung von neuen substituierten Biguaniden |
| AT00786/73A AT321318B (de) | 1971-04-02 | 1972-03-30 | Vzh von neuen substituierten biguaniden |
| AT00784/73A AT317239B (de) | 1971-04-02 | 1972-03-30 | Verfahren zur herstellung von neuen substituierten biguaniden |
| DD161938A DD95228A5 (cs) | 1971-04-02 | 1972-03-30 | |
| AT00785/73A AT317240B (de) | 1971-04-02 | 1972-03-30 | Verfahren zur herstellung von neuen substituierten biguaniden |
| HUSC383A HU162902B (cs) | 1971-04-02 | 1972-03-30 | |
| SU1907667A SU472501A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени замещенных бигуанида |
| SU1767915A SU535903A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени замещенных бигуанидов |
| SU1907668A SU493959A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени 1,2-бигуанидов |
| SU1907665A SU465784A3 (ru) | 1971-04-02 | 1972-03-31 | Способ получени замещенных бигуанида |
| BE781590A BE781590A (fr) | 1971-04-02 | 1972-03-31 | 1,2-biguanides, leur preparation et leur utilisation |
| CA138,838A CA988084A (en) | 1971-04-02 | 1972-04-04 | Substituted biguanides |
| NL7204493A NL7204493A (cs) | 1971-04-02 | 1972-04-04 | |
| FR7211727A FR2132396B1 (cs) | 1971-04-02 | 1972-04-04 | |
| AR245080A AR192485A1 (es) | 1971-04-02 | 1972-11-13 | Procedimiento para la preparacion de biguanidas 1,2-substituidas |
| AR245079A AR194285A1 (es) | 1971-04-02 | 1972-11-13 | Procedimiento para la preparacion de de biguanidas 1,2-sustituidas |
| US05/486,758 US3960949A (en) | 1971-04-02 | 1974-07-09 | 1,2-Biguanides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712117015 DE2117015A1 (de) | 1971-04-02 | 1971-04-02 | 1,2-Biguanide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2117015A1 true DE2117015A1 (de) | 1972-10-26 |
Family
ID=5804148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712117015 Withdrawn DE2117015A1 (de) | 1971-04-02 | 1971-04-02 | 1,2-Biguanide |
Country Status (19)
| Country | Link |
|---|---|
| AR (3) | AR194360A1 (cs) |
| AT (4) | AT321318B (cs) |
| AU (1) | AU468307B2 (cs) |
| BE (1) | BE781590A (cs) |
| CA (1) | CA988084A (cs) |
| CH (1) | CH579534A5 (cs) |
| CS (3) | CS161936B2 (cs) |
| DD (1) | DD95228A5 (cs) |
| DE (1) | DE2117015A1 (cs) |
| DK (1) | DK129651B (cs) |
| ES (1) | ES401124A1 (cs) |
| FR (1) | FR2132396B1 (cs) |
| GB (1) | GB1386130A (cs) |
| HU (1) | HU162902B (cs) |
| NL (1) | NL7204493A (cs) |
| NO (1) | NO135418C (cs) |
| SE (1) | SE377332B (cs) |
| SU (4) | SU535903A3 (cs) |
| ZA (1) | ZA722183B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008007314A1 (de) | 2008-02-02 | 2009-08-06 | Merck Patent Gmbh | Verfahren zur Herstellung von 3,6-Dihydro-1,3,5-triazinderivaten |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR940304A (fr) * | 1946-01-07 | 1948-12-09 | Ici Ltd | Procédé de fabrication de dérivés de biguanides |
-
1971
- 1971-04-02 DE DE19712117015 patent/DE2117015A1/de not_active Withdrawn
-
1972
- 1972-03-15 CS CS6963*A patent/CS161936B2/cs unknown
- 1972-03-15 CS CS6964*A patent/CS161937B2/cs unknown
- 1972-03-15 CS CS1724A patent/CS161935B2/cs unknown
- 1972-03-22 DK DK134572AA patent/DK129651B/da unknown
- 1972-03-23 ES ES401124A patent/ES401124A1/es not_active Expired
- 1972-03-27 GB GB1416272A patent/GB1386130A/en not_active Expired
- 1972-03-27 CH CH454672A patent/CH579534A5/xx not_active IP Right Cessation
- 1972-03-29 SE SE7204127A patent/SE377332B/xx unknown
- 1972-03-29 AR AR241248A patent/AR194360A1/es active
- 1972-03-29 NO NO1084/72A patent/NO135418C/no unknown
- 1972-03-30 AU AU40661/72A patent/AU468307B2/en not_active Expired
- 1972-03-30 AT AT00786/73A patent/AT321318B/de not_active IP Right Cessation
- 1972-03-30 AT AT279272A patent/AT313301B/de not_active IP Right Cessation
- 1972-03-30 HU HUSC383A patent/HU162902B/hu unknown
- 1972-03-30 AT AT00784/73A patent/AT317239B/de not_active IP Right Cessation
- 1972-03-30 DD DD161938A patent/DD95228A5/xx unknown
- 1972-03-30 ZA ZA722183A patent/ZA722183B/xx unknown
- 1972-03-30 AT AT00785/73A patent/AT317240B/de not_active IP Right Cessation
- 1972-03-31 SU SU1767915A patent/SU535903A3/ru active
- 1972-03-31 BE BE781590A patent/BE781590A/xx unknown
- 1972-03-31 SU SU1907667A patent/SU472501A3/ru active
- 1972-03-31 SU SU1907665A patent/SU465784A3/ru active
- 1972-03-31 SU SU1907668A patent/SU493959A3/ru active
- 1972-04-04 FR FR7211727A patent/FR2132396B1/fr not_active Expired
- 1972-04-04 NL NL7204493A patent/NL7204493A/xx not_active Application Discontinuation
- 1972-04-04 CA CA138,838A patent/CA988084A/en not_active Expired
- 1972-11-13 AR AR245080A patent/AR192485A1/es active
- 1972-11-13 AR AR245079A patent/AR194285A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| SE377332B (cs) | 1975-06-30 |
| NO135418C (cs) | 1977-04-05 |
| BE781590A (fr) | 1972-10-02 |
| SU535903A3 (ru) | 1976-11-15 |
| AR194285A1 (es) | 1973-06-29 |
| AT317239B (de) | 1974-08-26 |
| AT321318B (de) | 1975-03-25 |
| DD95228A5 (cs) | 1973-01-20 |
| CH579534A5 (cs) | 1976-09-15 |
| SU493959A3 (ru) | 1975-11-28 |
| DK129651C (cs) | 1975-04-07 |
| CS161935B2 (cs) | 1975-06-10 |
| SU465784A3 (ru) | 1975-03-30 |
| CA988084A (en) | 1976-04-27 |
| NL7204493A (cs) | 1972-10-04 |
| AT313301B (de) | 1974-02-11 |
| ES401124A1 (es) | 1975-02-16 |
| DK129651B (da) | 1974-11-04 |
| AR194360A1 (es) | 1973-07-13 |
| FR2132396A1 (cs) | 1972-11-17 |
| SU472501A3 (ru) | 1975-05-30 |
| AT317240B (de) | 1974-08-26 |
| CS161937B2 (cs) | 1975-06-10 |
| GB1386130A (en) | 1975-03-05 |
| NO135418B (cs) | 1976-12-27 |
| AR192485A1 (es) | 1973-02-21 |
| AU468307B2 (en) | 1973-10-04 |
| CS161936B2 (cs) | 1975-06-10 |
| HU162902B (cs) | 1973-04-28 |
| ZA722183B (en) | 1972-12-27 |
| FR2132396B1 (cs) | 1975-10-10 |
| AU4066172A (en) | 1973-10-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8139 | Disposal/non-payment of the annual fee |