DE2512510A1 - Neue organische verbindungen und verfahren zu deren herstellung - Google Patents
Neue organische verbindungen und verfahren zu deren herstellungInfo
- Publication number
- DE2512510A1 DE2512510A1 DE19752512510 DE2512510A DE2512510A1 DE 2512510 A1 DE2512510 A1 DE 2512510A1 DE 19752512510 DE19752512510 DE 19752512510 DE 2512510 A DE2512510 A DE 2512510A DE 2512510 A1 DE2512510 A1 DE 2512510A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- carbon atoms
- hydrogen
- group
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 50
- -1 methylenedioxy group Chemical group 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 13
- 238000009835 boiling Methods 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000012458 free base Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- ZDGKJHSUFPMOKZ-UHFFFAOYSA-N (7-phenyl-2,3-dihydro-1h-1,4-diazepin-5-yl)hydrazine Chemical compound NNC1=NCCNC(C=2C=CC=CC=2)=C1 ZDGKJHSUFPMOKZ-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- ONOBXDPYDHTSBQ-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-diazepine Chemical compound C1CC=CCNN1 ONOBXDPYDHTSBQ-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- AWRAIODVADKTLB-UHFFFAOYSA-N n-methyl-7-phenyl-2,3-dihydro-1h-1,4-diazepin-5-amine Chemical compound CNC1=NCCNC(C=2C=CC=CC=2)=C1 AWRAIODVADKTLB-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical class NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 210000003608 fece Anatomy 0.000 description 3
- 239000010871 livestock manure Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- IDJNHFOGECCZCZ-UHFFFAOYSA-M 2-tert-butyl-5-phenyl-1,2-oxazol-2-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.O1[N+](C(C)(C)C)=CC=C1C1=CC=CC=C1 IDJNHFOGECCZCZ-UHFFFAOYSA-M 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- RZCRWEUYBLWZSE-UHFFFAOYSA-N 7-phenyl-5-pyrrolidin-1-yl-2,3-dihydro-1h-1,4-diazepine Chemical compound C1CCCN1C1=NCCNC(C=2C=CC=CC=2)=C1 RZCRWEUYBLWZSE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 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
- 125000004893 1,1-dimethylethylamino group Chemical group CC(C)(C)N* 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- XOZKXMNUBNAFRI-UHFFFAOYSA-M 2-tert-butyl-5-(4-methoxyphenyl)-1,2-oxazol-2-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC(OC)=CC=C1C1=CC=[N+](C(C)(C)C)O1 XOZKXMNUBNAFRI-UHFFFAOYSA-M 0.000 description 1
- XDVQKVNILNZRFH-UHFFFAOYSA-N 5-ethoxy-7-phenyl-2,3-dihydro-1h-1,4-diazepine Chemical compound CCOC1=NCCNC(C=2C=CC=CC=2)=C1 XDVQKVNILNZRFH-UHFFFAOYSA-N 0.000 description 1
- QTBKTEDAGWNUEX-UHFFFAOYSA-N 7-phenyl-1,2,3,4-tetrahydro-1,4-diazepin-5-one Chemical compound O=C1NCCNC(C=2C=CC=CC=2)=C1 QTBKTEDAGWNUEX-UHFFFAOYSA-N 0.000 description 1
- XPWZYNDAEUMIAW-UHFFFAOYSA-N 7-phenyl-2,3-dihydro-1h-1,4-diazepin-5-amine Chemical compound NC1=NCCNC(C=2C=CC=CC=2)=C1 XPWZYNDAEUMIAW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- KWFXHDNHNMXZAB-UHFFFAOYSA-N N-butyl-7-phenyl-2,3-dihydro-1H-1,4-diazepin-5-amine perchloric acid Chemical compound OCl(=O)(=O)=O.CCCCNC1=NCCNC(C=2C=CC=CC=2)=C1 KWFXHDNHNMXZAB-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000002036 chloroform fraction Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 239000002032 methanolic fraction Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- FJLHLDBEZKTSOK-UHFFFAOYSA-N n-ethyl-n-methylformamide Chemical compound CCN(C)C=O FJLHLDBEZKTSOK-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- GWYCOTJQPGWSMJ-UHFFFAOYSA-N n-tert-butyl-7-phenyl-2,3-dihydro-1h-1,4-diazepin-5-amine Chemical compound CC(C)(C)NC1=NCCNC(C=2C=CC=CC=2)=C1 GWYCOTJQPGWSMJ-UHFFFAOYSA-N 0.000 description 1
- QAROCPJEUJODHA-UHFFFAOYSA-N n-tert-butyl-7-phenyl-2,3-dihydro-1h-1,4-diazepin-5-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CC(C)(C)NC1=NCCNC(C=2C=CC=CC=2)=C1 QAROCPJEUJODHA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 0.000 description 1
- QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical compound C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US456017A US3929884A (en) | 1974-03-29 | 1974-03-29 | Intermediates in the synthesis of 5-alkylamino-7-phenyl or substituted phenyl-2,3-dihydro-1H-1,4-diazepines |
| US52834474A | 1974-11-29 | 1974-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2512510A1 true DE2512510A1 (de) | 1975-10-02 |
Family
ID=27038065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752512510 Withdrawn DE2512510A1 (de) | 1974-03-29 | 1975-03-21 | Neue organische verbindungen und verfahren zu deren herstellung |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5136482A (en, 2012) |
| AU (1) | AU500509B2 (en, 2012) |
| CA (1) | CA1064488A (en, 2012) |
| CH (1) | CH613696A5 (en, 2012) |
| DE (1) | DE2512510A1 (en, 2012) |
| DK (1) | DK137127B (en, 2012) |
| ES (1) | ES453665A1 (en, 2012) |
| FI (1) | FI750827A7 (en, 2012) |
| FR (1) | FR2265397B1 (en, 2012) |
| GB (1) | GB1494433A (en, 2012) |
| IE (1) | IE40951B1 (en, 2012) |
| IL (1) | IL46958A (en, 2012) |
| NL (1) | NL7503532A (en, 2012) |
| NO (1) | NO750978L (en, 2012) |
| SE (1) | SE7503278L (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0608655D0 (en) * | 2006-05-03 | 2006-06-14 | Merck Sharp & Dohme | Therapeutic Treatment |
-
1975
- 1975-03-19 CH CH349975A patent/CH613696A5/xx not_active IP Right Cessation
- 1975-03-20 DK DK117975AA patent/DK137127B/da unknown
- 1975-03-20 FI FI750827A patent/FI750827A7/fi not_active Application Discontinuation
- 1975-03-21 SE SE7503278A patent/SE7503278L/xx unknown
- 1975-03-21 DE DE19752512510 patent/DE2512510A1/de not_active Withdrawn
- 1975-03-21 NO NO750978A patent/NO750978L/no unknown
- 1975-03-25 NL NL7503532A patent/NL7503532A/xx not_active Application Discontinuation
- 1975-03-26 FR FR7509428A patent/FR2265397B1/fr not_active Expired
- 1975-03-27 CA CA223,292A patent/CA1064488A/en not_active Expired
- 1975-03-27 GB GB12866/75A patent/GB1494433A/en not_active Expired
- 1975-03-27 JP JP50036157A patent/JPS5136482A/ja active Pending
- 1975-03-27 IE IE699/75A patent/IE40951B1/xx unknown
- 1975-03-27 AU AU79601/75A patent/AU500509B2/en not_active Expired
- 1975-03-28 IL IL46958A patent/IL46958A/xx unknown
-
1976
- 1976-11-25 ES ES453665A patent/ES453665A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH613696A5 (en) | 1979-10-15 |
| FR2265397B1 (en, 2012) | 1978-08-04 |
| DK137127C (en, 2012) | 1978-06-26 |
| DK117975A (en, 2012) | 1975-09-30 |
| JPS5136482A (en) | 1976-03-27 |
| IE40951B1 (en) | 1979-09-12 |
| NL7503532A (nl) | 1975-10-01 |
| FI750827A7 (en, 2012) | 1975-09-21 |
| IL46958A (en) | 1978-07-31 |
| CA1064488A (en) | 1979-10-16 |
| FR2265397A1 (en, 2012) | 1975-10-24 |
| IL46958A0 (en) | 1975-05-22 |
| AU500509B2 (en) | 1979-05-24 |
| NO750978L (en, 2012) | 1975-09-30 |
| DK137127B (da) | 1978-01-23 |
| GB1494433A (en) | 1977-12-07 |
| SE7503278L (en, 2012) | 1975-09-30 |
| AU7960175A (en) | 1976-09-30 |
| IE40951L (en) | 1975-09-29 |
| ES453665A1 (es) | 1977-11-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH653682A5 (de) | 2-(4-(4-(4,4-dialkyl-2,6-piperidindion-1-yl)butyl)-1-piperazinyl)pyridine. | |
| DE1620035A1 (de) | 3-Amino-5-X-6-halogenpyrazinonitrile und Verfahren zu deren Herstellung | |
| DE2429745C3 (de) | Verfahren zur Herstellung von Triacetonamin | |
| DE2352632B2 (de) | Berbinderivate, Verfahren zu deren Herstellung und Arzneimittel | |
| DE2512510A1 (de) | Neue organische verbindungen und verfahren zu deren herstellung | |
| DE69920003T2 (de) | Verfahren zur herstellung von 1,3-disubstituierten-4-oxocyclischen harnstoffen | |
| DE1076691B (de) | Verfahren zur Herstellung von Phenthiazinderivaten | |
| EP0152598B1 (de) | Cyanomethyl-(2-cyano-ethyl)-(3-hydroxy-propyl)-amin, seine Verwendung zur Herstellung von 1-(3-Hydroxy-propyl)-1,4-diazepan und 1,4 Bis-[3-(3,4,5-trimethoxy-benzoyloxy)-propyl]-diazepan | |
| CH635834A5 (de) | Dibenzo(d,g)(1,3,6)dioxazocin-derivate, verfahren zu ihrer herstellung und die diese verbindungen enthaltenden arzneimittelpraeparate. | |
| DE1923821A1 (de) | 1,2,4,5-Tetrahydro-[3H]-benzo-1,4-diazepin-2,5-dion-Derivate,Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Arzneipraeparaten | |
| DE1620197A1 (de) | Verfahren zum Herstellen 5-substituierter 2-Oxazolidinone | |
| DE2809798A1 (de) | Verfahren zur herstellung von 5-substituierten tetrazolen | |
| DE2036181A1 (de) | Benzamidine und Verfahren zu ihrer Her stellung | |
| DE2427503C3 (de) | Halogenfusarsäureamide, Verfahren zur Herstellung derselben und Mittel mit einem Gehalt derselben | |
| AT238155B (de) | Verfahren zur Herstellung von neuen Dihalogen-amino-benzylaminen und deren Säureadditionssalzen mit anorganischen oder organischen Säuren | |
| AT235279B (de) | Verfahren zur Herstellung neuer 5-Nitrofurfuryliden-hydrazine | |
| CH493535A (de) | Verfahren zur Herstellung von Pyrazinoylguanidinen und Pyrazinamidoguanidinen | |
| DE1126880B (de) | Verfahren zur Herstellung von Piperazinderivaten | |
| AT260916B (de) | Verfahren zur Herstellung von neuen α-(Aminoalkoxyphenyl)-α'-nitrostilbenen und deren Säureadditionssalzen bzw. quaternären Ammoniumverbindungen | |
| AT311371B (de) | Verfahren zur Herstellung von neuen Pyridazon-6-iminen | |
| AT224639B (de) | Verfahren zur Herstellung von neuen Piperazinderivaten | |
| AT236389B (de) | Verfahren zur Herstellung von neuen N-substituierten heterocyclischen Verbindungen | |
| AT236394B (de) | Verfahren zur Herstellung von neuen N-substituierten heterocyclischen Verbindungen | |
| AT276384B (de) | Verfahren zur Herstellung von neuen, basisch substituierten 2-(Acylamino)-3-carbomoyl-4,5,6,7-tetrahydro-benzo[b] thiophen-Deivaten und ihren Salzen | |
| AT359492B (de) | Verfahren zur herstellung neuer indazolderivate und ihrer salze |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |