NO762782L - - Google Patents
Info
- Publication number
- NO762782L NO762782L NO762782A NO762782A NO762782L NO 762782 L NO762782 L NO 762782L NO 762782 A NO762782 A NO 762782A NO 762782 A NO762782 A NO 762782A NO 762782 L NO762782 L NO 762782L
- Authority
- NO
- Norway
- Prior art keywords
- parts
- nitroimidazole
- azidoethyl
- compound
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 42
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 26
- ZOHNJAQYCPKISP-UHFFFAOYSA-N 1-(2-azidoethyl)-2-methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCN=[N+]=[N-] ZOHNJAQYCPKISP-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- UDSKWVHYNOSUOT-UHFFFAOYSA-N 1-(2-chloroethyl)-5-nitroimidazole Chemical compound [O-][N+](=O)C1=CN=CN1CCCl UDSKWVHYNOSUOT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- PECXYRBEPGUJNS-UHFFFAOYSA-N 1-(2-azidoethyl)-2-methylimidazole Chemical compound CC1=NC=CN1CCN=[N+]=[N-] PECXYRBEPGUJNS-UHFFFAOYSA-N 0.000 claims description 3
- VDDGUWJZSGURBB-UHFFFAOYSA-N 1-(2-azidoethyl)-5-nitroimidazole Chemical compound [O-][N+](=O)C1=CN=CN1CCN=[N+]=[N-] VDDGUWJZSGURBB-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- SAKPTPNVBRFNIN-UHFFFAOYSA-N 1-(2-azidoethyl)-2-(4-fluorophenyl)-5-nitroimidazole Chemical compound [N-]=[N+]=NCCN1C([N+](=O)[O-])=CN=C1C1=CC=C(F)C=C1 SAKPTPNVBRFNIN-UHFFFAOYSA-N 0.000 claims description 2
- IXGKMCFVFDBVKQ-UHFFFAOYSA-N 1-(2-azidoethyl)-2-methyl-4-nitroimidazole Chemical compound CC1=NC([N+]([O-])=O)=CN1CCN=[N+]=[N-] IXGKMCFVFDBVKQ-UHFFFAOYSA-N 0.000 claims description 2
- PIYNTNXOGGKWDR-UHFFFAOYSA-N 1-(2-chloroethyl)-2-methylimidazole Chemical compound CC1=NC=CN1CCCl PIYNTNXOGGKWDR-UHFFFAOYSA-N 0.000 claims description 2
- WZZCXODOWVBLOF-UHFFFAOYSA-N 2-(2-methyl-4-nitroimidazol-1-yl)ethyl methanesulfonate Chemical compound CC1=NC([N+]([O-])=O)=CN1CCOS(C)(=O)=O WZZCXODOWVBLOF-UHFFFAOYSA-N 0.000 claims description 2
- MBLJZGSJLSUHRO-UHFFFAOYSA-N 2-(2-methyl-5-nitroimidazol-1-yl)ethyl methanesulfonate Chemical compound CC1=NC=C([N+]([O-])=O)N1CCOS(C)(=O)=O MBLJZGSJLSUHRO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000002609 medium Substances 0.000 description 24
- 238000012360 testing method Methods 0.000 description 24
- 239000012153 distilled water Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000523 sample Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 10
- 238000011534 incubation Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 102000015427 Angiotensins Human genes 0.000 description 7
- 108010064733 Angiotensins Proteins 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229920001817 Agar Polymers 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241001502500 Trichomonadida Species 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000005292 vacuum distillation Methods 0.000 description 6
- -1 1-methyl-1,2-ethanediyl Chemical group 0.000 description 5
- 241000605739 Desulfovibrio desulfuricans Species 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- LPWURFKBBUADGL-UHFFFAOYSA-N 2-(5-nitro-2-phenylimidazol-1-yl)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCN1C([N+]([O-])=O)=CN=C1C1=CC=CC=C1 LPWURFKBBUADGL-UHFFFAOYSA-N 0.000 description 3
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 3
- 235000014469 Bacillus subtilis Nutrition 0.000 description 3
- 240000009108 Chlorella vulgaris Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 description 3
- 241000224527 Trichomonas vaginalis Species 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 229940041514 candida albicans extract Drugs 0.000 description 3
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 3
- 210000003754 fetus Anatomy 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 239000012485 toluene extract Substances 0.000 description 3
- 239000012138 yeast extract Substances 0.000 description 3
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- 244000063299 Bacillus subtilis Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- 241001631457 Cannula Species 0.000 description 2
- 235000007089 Chlorella vulgaris Nutrition 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 244000026610 Cynodon dactylon var. affinis Species 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241001149959 Fusarium sp. Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002211 L-ascorbic acid Substances 0.000 description 2
- 235000000069 L-ascorbic acid Nutrition 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- 241000224539 Pentatrichomonas hominis Species 0.000 description 2
- 241000191963 Staphylococcus epidermidis Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- VLSOAXRVHARBEQ-UHFFFAOYSA-N [4-fluoro-2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(F)C=C1CO VLSOAXRVHARBEQ-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical group [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- 229940111685 dibasic potassium phosphate Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000003191 femoral vein Anatomy 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 2
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 239000007143 thioglycolate medium Substances 0.000 description 2
- 108010050327 trypticase-soy broth Proteins 0.000 description 2
- OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 description 1
- YASYFSBQZLXLLE-UHFFFAOYSA-N 1-(2-azidoethyl)-2-(2-iodophenyl)-5-nitroimidazole Chemical compound [N-]=[N+]=NCCN1C([N+](=O)[O-])=CN=C1C1=CC=CC=C1I YASYFSBQZLXLLE-UHFFFAOYSA-N 0.000 description 1
- QQYSFJHLNSBNJW-UHFFFAOYSA-N 1-(2-azidoethyl)-2-ethyl-5-nitroimidazole;hydrochloride Chemical group Cl.CCC1=NC=C([N+]([O-])=O)N1CCN=[N+]=[N-] QQYSFJHLNSBNJW-UHFFFAOYSA-N 0.000 description 1
- FRVHTGNRLREHIV-UHFFFAOYSA-N 1-(2-azidoethyl)-2-methylimidazole;hydrochloride Chemical compound Cl.CC1=NC=CN1CCN=[N+]=[N-] FRVHTGNRLREHIV-UHFFFAOYSA-N 0.000 description 1
- FJAVJPXMVGIHOW-UHFFFAOYSA-N 1-(2-azidoethyl)-5-nitro-2-phenylimidazole Chemical group [N-]=[N+]=NCCN1C([N+](=O)[O-])=CN=C1C1=CC=CC=C1 FJAVJPXMVGIHOW-UHFFFAOYSA-N 0.000 description 1
- HCYPCQYVVSXOAE-UHFFFAOYSA-N 1-(2-azidoethyl)-5-nitroimidazole;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CN=CN1CCN=[N+]=[N-] HCYPCQYVVSXOAE-UHFFFAOYSA-N 0.000 description 1
- HIDWODJQBFAFAE-UHFFFAOYSA-N 1-(2-chloroethyl)-2-ethyl-5-nitroimidazole Chemical compound CCC1=NC=C([N+]([O-])=O)N1CCCl HIDWODJQBFAFAE-UHFFFAOYSA-N 0.000 description 1
- UIVKAVPQIJCCJS-UHFFFAOYSA-N 1-(3-azidopropyl)-2-methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCCN=[N+]=[N-] UIVKAVPQIJCCJS-UHFFFAOYSA-N 0.000 description 1
- XGJOHNQZQXVTSA-UHFFFAOYSA-N 1-(3-azidopropyl)-2-methyl-5-nitroimidazole;hydrochloride Chemical compound Cl.CC1=NC=C([N+]([O-])=O)N1CCCN=[N+]=[N-] XGJOHNQZQXVTSA-UHFFFAOYSA-N 0.000 description 1
- ZIYUWHWFIOERMG-UHFFFAOYSA-N 1-(3-chlorobutyl)-2-methyl-5-nitroimidazole Chemical compound CC(Cl)CCN1C(C)=NC=C1[N+]([O-])=O ZIYUWHWFIOERMG-UHFFFAOYSA-N 0.000 description 1
- JCQFIQJFPHTLGY-UHFFFAOYSA-N 1-(3-chloropropyl)-2-methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCCCl JCQFIQJFPHTLGY-UHFFFAOYSA-N 0.000 description 1
- WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 description 1
- ORFABGGUQBYRCS-UHFFFAOYSA-N 2-[2-(2-iodophenyl)-5-nitroimidazol-1-yl]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCN1C([N+]([O-])=O)=CN=C1C1=CC=CC=C1I ORFABGGUQBYRCS-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000193468 Clostridium perfringens Species 0.000 description 1
- 241001470651 Clostridium perfringens ATCC 13124 Species 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 241000751182 Staphylococcus epidermidis ATCC 12228 Species 0.000 description 1
- 241000224528 Tritrichomonas Species 0.000 description 1
- 241001058196 Tritrichomonas foetus Species 0.000 description 1
- 241001123669 Verticillium albo-atrum Species 0.000 description 1
- HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960002028 atropine sulfate Drugs 0.000 description 1
- 230000003816 axenic effect Effects 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000003457 ganglion blocking agent Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 229960001008 heparin sodium Drugs 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 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
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- VXAPDXVBDZRZKP-UHFFFAOYSA-N nitric acid phosphoric acid Chemical compound O[N+]([O-])=O.OP(O)(O)=O VXAPDXVBDZRZKP-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 210000003437 trachea Anatomy 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
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C07D233/95—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by nitrogen atoms, attached to other ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/603,336 US3962274A (en) | 1975-08-11 | 1975-08-11 | 1-azidoalkylimidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO762782L true NO762782L (nl) | 1977-02-14 |
Family
ID=24414995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO762782A NO762782L (nl) | 1975-08-11 | 1976-08-10 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3962274A (nl) |
| JP (1) | JPS5223077A (nl) |
| AT (1) | AT352713B (nl) |
| AU (1) | AU498354B2 (nl) |
| BE (1) | BE845075A (nl) |
| CA (1) | CA1067503A (nl) |
| CH (1) | CH621778A5 (nl) |
| DE (1) | DE2635914A1 (nl) |
| DK (1) | DK361976A (nl) |
| ES (1) | ES450586A1 (nl) |
| FR (1) | FR2320747A1 (nl) |
| GB (1) | GB1499969A (nl) |
| IE (1) | IE43589B1 (nl) |
| NL (1) | NL7608880A (nl) |
| NO (1) | NO762782L (nl) |
| NZ (1) | NZ181736A (nl) |
| SE (1) | SE7608910L (nl) |
| ZA (1) | ZA764805B (nl) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113387927B (zh) * | 2021-06-17 | 2022-10-04 | 首都医科大学脑重大疾病研究中心(北京脑重大疾病研究院) | 一种用于制备乏氧显像剂的硝基咪唑类衍生物及其制备方法和应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
-
1975
- 1975-08-11 US US05/603,336 patent/US3962274A/en not_active Expired - Lifetime
-
1976
- 1976-08-10 CH CH1019876A patent/CH621778A5/de not_active IP Right Cessation
- 1976-08-10 AU AU16722/76A patent/AU498354B2/en not_active Expired
- 1976-08-10 DE DE19762635914 patent/DE2635914A1/de not_active Withdrawn
- 1976-08-10 ES ES450586A patent/ES450586A1/es not_active Expired
- 1976-08-10 SE SE7608910A patent/SE7608910L/xx unknown
- 1976-08-10 NZ NZ181736A patent/NZ181736A/xx unknown
- 1976-08-10 GB GB33312/76A patent/GB1499969A/en not_active Expired
- 1976-08-10 AT AT595376A patent/AT352713B/de not_active IP Right Cessation
- 1976-08-10 JP JP51095329A patent/JPS5223077A/ja active Pending
- 1976-08-10 NO NO762782A patent/NO762782L/no unknown
- 1976-08-10 CA CA258,784A patent/CA1067503A/en not_active Expired
- 1976-08-10 NL NL7608880A patent/NL7608880A/nl not_active Application Discontinuation
- 1976-08-10 ZA ZA764805A patent/ZA764805B/xx unknown
- 1976-08-10 IE IE1772/76A patent/IE43589B1/en unknown
- 1976-08-11 FR FR7624546A patent/FR2320747A1/fr active Granted
- 1976-08-11 BE BE169719A patent/BE845075A/xx unknown
- 1976-08-11 DK DK361976A patent/DK361976A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA764805B (en) | 1977-09-28 |
| ES450586A1 (es) | 1977-08-16 |
| IE43589B1 (en) | 1981-04-08 |
| AT352713B (de) | 1979-10-10 |
| DK361976A (da) | 1977-02-12 |
| IE43589L (en) | 1977-02-11 |
| CH621778A5 (nl) | 1981-02-27 |
| NL7608880A (nl) | 1977-02-15 |
| GB1499969A (en) | 1978-02-01 |
| AU1672276A (en) | 1978-02-16 |
| NZ181736A (en) | 1978-11-13 |
| BE845075A (fr) | 1977-02-11 |
| AU498354B2 (en) | 1979-03-08 |
| ATA595376A (de) | 1979-03-15 |
| FR2320747A1 (fr) | 1977-03-11 |
| CA1067503A (en) | 1979-12-04 |
| SE7608910L (sv) | 1977-02-12 |
| US3962274A (en) | 1976-06-08 |
| FR2320747B1 (nl) | 1979-09-21 |
| JPS5223077A (en) | 1977-02-21 |
| DE2635914A1 (de) | 1977-03-03 |
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