NO782399L - Fremgangsmaate ved fremstilling av 1-acyl-2-cyanaziridiner - Google Patents
Fremgangsmaate ved fremstilling av 1-acyl-2-cyanaziridinerInfo
- Publication number
- NO782399L NO782399L NO782399A NO782399A NO782399L NO 782399 L NO782399 L NO 782399L NO 782399 A NO782399 A NO 782399A NO 782399 A NO782399 A NO 782399A NO 782399 L NO782399 L NO 782399L
- Authority
- NO
- Norway
- Prior art keywords
- group
- cyanaziridine
- optionally
- ether
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 136
- PGZUFTROELAOMP-UHFFFAOYSA-N aziridine-2-carbonitrile Chemical compound N#CC1CN1 PGZUFTROELAOMP-UHFFFAOYSA-N 0.000 claims description 123
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- -1 ureido- Chemical class 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 150000002825 nitriles Chemical class 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Chemical group 0.000 claims description 7
- 239000001301 oxygen Chemical group 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- XNMVAVGXJZFTEH-BUYFANAVSA-N (1r,2s,4r)-4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-carboxylic acid Chemical group C1C[C@@]2(C)C(=O)[C@@H](C(O)=O)[C@@H]1C2(C)C XNMVAVGXJZFTEH-BUYFANAVSA-N 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical group CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Chemical group CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 claims description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical group C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical group 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical group C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 497
- 239000000243 solution Substances 0.000 description 128
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 125
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 106
- 239000003921 oil Substances 0.000 description 82
- 235000019198 oils Nutrition 0.000 description 82
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 72
- 239000000706 filtrate Substances 0.000 description 69
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 62
- 150000002168 ethanoic acid esters Chemical class 0.000 description 58
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 54
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 49
- 238000001704 evaporation Methods 0.000 description 49
- 230000008020 evaporation Effects 0.000 description 44
- 238000003756 stirring Methods 0.000 description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- 239000000741 silica gel Substances 0.000 description 35
- 229910002027 silica gel Inorganic materials 0.000 description 35
- 238000001816 cooling Methods 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 30
- 238000001819 mass spectrum Methods 0.000 description 28
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 26
- 235000017557 sodium bicarbonate Nutrition 0.000 description 24
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
- 238000000921 elemental analysis Methods 0.000 description 23
- 239000012071 phase Substances 0.000 description 22
- 239000000126 substance Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 239000012452 mother liquor Substances 0.000 description 19
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- 239000003480 eluent Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- 150000003840 hydrochlorides Chemical class 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000001665 trituration Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229960002449 glycine Drugs 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 230000003308 immunostimulating effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 239000004471 Glycine Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- MYTAKEVMLYCYIE-UHFFFAOYSA-N 2-[(2-phenoxyacetyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)COC1=CC=CC=C1 MYTAKEVMLYCYIE-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- LNQCUTNLHUQZLR-VNPYQEQNSA-N Iridin Natural products O(C)c1c(O)c2C(=O)C(c3cc(OC)c(OC)c(O)c3)=COc2cc1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 LNQCUTNLHUQZLR-VNPYQEQNSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 108010047623 iridine Proteins 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BYYFJADNNPSTCO-UHFFFAOYSA-N 2-[(2-butylsulfanylacetyl)amino]acetic acid Chemical compound CCCCSCC(=O)NCC(O)=O BYYFJADNNPSTCO-UHFFFAOYSA-N 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 230000003327 cancerostatic effect Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- CYTLOMOEKMHGPM-UHFFFAOYSA-N 1-methyl-3-nitropyrazole-4-carbonyl chloride Chemical compound CN1C=C(C(Cl)=O)C([N+]([O-])=O)=N1 CYTLOMOEKMHGPM-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- RVHGZLBJHUREQW-UHFFFAOYSA-N 2-(1-benzofuran-2-carbonylamino)acetic acid Chemical compound C1=CC=C2OC(C(=O)NCC(=O)O)=CC2=C1 RVHGZLBJHUREQW-UHFFFAOYSA-N 0.000 description 2
- NDLLIOPAEOBFKZ-UHFFFAOYSA-N 2-(cyclopropanecarbonylamino)acetic acid Chemical compound OC(=O)CNC(=O)C1CC1 NDLLIOPAEOBFKZ-UHFFFAOYSA-N 0.000 description 2
- SYPPNKVSWGEQBC-UHFFFAOYSA-N 2-[(1-methyl-3-nitropyrazole-4-carbonyl)amino]acetic acid Chemical compound CN1C=C(C(=O)NCC(O)=O)C([N+]([O-])=O)=N1 SYPPNKVSWGEQBC-UHFFFAOYSA-N 0.000 description 2
- OVJKNWZFRRCVGV-UHFFFAOYSA-N 2-[(2-phenylsulfanylacetyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)CSC1=CC=CC=C1 OVJKNWZFRRCVGV-UHFFFAOYSA-N 0.000 description 2
- VABYVFZVTIDNOA-UHFFFAOYSA-N 2-cyclohexylacetyl chloride Chemical compound ClC(=O)CC1CCCCC1 VABYVFZVTIDNOA-UHFFFAOYSA-N 0.000 description 2
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 2
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- KSPQDMRTZZYQLM-UHFFFAOYSA-N N-(2-furoyl)glycine Chemical compound OC(=O)CNC(=O)C1=CC=CO1 KSPQDMRTZZYQLM-UHFFFAOYSA-N 0.000 description 2
- KTHDTJVBEPMMGL-VKHMYHEASA-N N-acetyl-L-alanine Chemical compound OC(=O)[C@H](C)NC(C)=O KTHDTJVBEPMMGL-VKHMYHEASA-N 0.000 description 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- ROXXNENGCGLRSW-UHFFFAOYSA-N N-cyclohexylcarbonylglycine Natural products OC(=O)CNC(=O)C1CCCCC1 ROXXNENGCGLRSW-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- JXIDRUSBYYMCON-UHFFFAOYSA-N butan-2-one;heptane Chemical compound CCC(C)=O.CCCCCCC JXIDRUSBYYMCON-UHFFFAOYSA-N 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- UCAGLBKTLXCODC-UHFFFAOYSA-N carzenide Chemical compound NS(=O)(=O)C1=CC=C(C(O)=O)C=C1 UCAGLBKTLXCODC-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004698 lymphocyte Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- JDRMYOQETPMYQX-UHFFFAOYSA-N monomethyl succinate Chemical compound COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 description 2
- 150000002829 nitrogen Chemical class 0.000 description 2
- 230000003204 osmotic effect Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- UTYVDVLMYQPLQB-UHFFFAOYSA-N phenylacetylglycine Chemical compound OC(=O)CNC(=O)CC1=CC=CC=C1 UTYVDVLMYQPLQB-UHFFFAOYSA-N 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-OLQVQODUSA-N (1s,2r)-cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)[C@H]1CCCC[C@H]1C(O)=O QSAWQNUELGIYBC-OLQVQODUSA-N 0.000 description 1
- XNMVAVGXJZFTEH-NSMOOJLNSA-N (1s,4s)-4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-carboxylic acid Chemical compound C1C[C@]2(C)C(=O)C(C(O)=O)[C@H]1C2(C)C XNMVAVGXJZFTEH-NSMOOJLNSA-N 0.000 description 1
- DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 1
- GRTWTVFDPBKQNU-MQQKCMAXSA-N (2e,4e)-hexa-2,4-dienoyl chloride Chemical compound C\C=C\C=C\C(Cl)=O GRTWTVFDPBKQNU-MQQKCMAXSA-N 0.000 description 1
- DIWVBIXQCNRCFE-MRVPVSSYSA-N (2r)-2-methoxy-2-phenylacetic acid Chemical compound CO[C@@H](C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-MRVPVSSYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- QUCHWTCTBHQQDU-BYPYZUCNSA-N (2s)-2-amino-4-oxopentanoic acid Chemical compound CC(=O)C[C@H](N)C(O)=O QUCHWTCTBHQQDU-BYPYZUCNSA-N 0.000 description 1
- DIWVBIXQCNRCFE-QMMMGPOBSA-N (2s)-2-methoxy-2-phenylacetic acid Chemical compound CO[C@H](C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-QMMMGPOBSA-N 0.000 description 1
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 1
- NRCHXNLCBKWXPH-ZZXKWVIFSA-N (e)-3-(4-hydroxyphenyl)prop-2-enoyl chloride Chemical compound OC1=CC=C(\C=C\C(Cl)=O)C=C1 NRCHXNLCBKWXPH-ZZXKWVIFSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- ZRSGZIMDIHBXIN-UHFFFAOYSA-N 1,3-benzodioxole-5-carbonyl chloride Chemical compound ClC(=O)C1=CC=C2OCOC2=C1 ZRSGZIMDIHBXIN-UHFFFAOYSA-N 0.000 description 1
- TZCXSRUIBDZAOB-UHFFFAOYSA-N 1-(2-imidazol-1-ylacetyl)aziridine-2-carbonitrile Chemical compound C1C(C#N)N1C(=O)CN1C=CN=C1 TZCXSRUIBDZAOB-UHFFFAOYSA-N 0.000 description 1
- CMHIVBVCAQBCFE-UHFFFAOYSA-N 1-(2-methyl-1,3-thiazole-5-carbonyl)aziridine-2-carbonitrile Chemical compound S1C(C)=NC=C1C(=O)N1C(C#N)C1 CMHIVBVCAQBCFE-UHFFFAOYSA-N 0.000 description 1
- MOACFBBDROVXSG-UHFFFAOYSA-N 1-(2-methylsulfanylbenzoyl)aziridine-2-carbonitrile Chemical compound CSC1=CC=CC=C1C(=O)N1C(C#N)C1 MOACFBBDROVXSG-UHFFFAOYSA-N 0.000 description 1
- KDJVBBKMFLYXAB-UHFFFAOYSA-N 1-(2-methylsulfonylbenzoyl)aziridine-2-carbonitrile Chemical compound CS(=O)(=O)C1=CC=CC=C1C(=O)N1C(C#N)C1 KDJVBBKMFLYXAB-UHFFFAOYSA-N 0.000 description 1
- WWYSZVKPIOTREH-UHFFFAOYSA-N 1-(2-pyrazol-1-ylacetyl)aziridine-2-carbonitrile Chemical compound C1C(C#N)N1C(=O)CN1C=CC=N1 WWYSZVKPIOTREH-UHFFFAOYSA-N 0.000 description 1
- UHUGXBTVOJZVMO-UHFFFAOYSA-N 1-(2-pyridin-2-ylacetyl)aziridine-2-carbonitrile Chemical compound C1C(C#N)N1C(=O)CC1=CC=CC=N1 UHUGXBTVOJZVMO-UHFFFAOYSA-N 0.000 description 1
- RNZOVYDOQYLCND-UHFFFAOYSA-N 1-(3,4,5-trimethoxybenzoyl)aziridine-2-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2C(C2)C#N)=C1 RNZOVYDOQYLCND-UHFFFAOYSA-N 0.000 description 1
- TUSNACTZKIRSJN-UHFFFAOYSA-N 1-(3-chloropropanoyl)aziridine-2-carbonitrile Chemical compound ClCCC(=O)N1CC1C#N TUSNACTZKIRSJN-UHFFFAOYSA-N 0.000 description 1
- RZHJJILZUKNEKM-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclopentane-1-carbonyl chloride Chemical compound C=1C=C(Cl)C=CC=1C1(C(=O)Cl)CCCC1 RZHJJILZUKNEKM-UHFFFAOYSA-N 0.000 description 1
- VINOUPJXQKWKJA-UHFFFAOYSA-N 1-(4-cyanobenzoyl)aziridine-2-carbonitrile Chemical compound C=1C=C(C#N)C=CC=1C(=O)N1CC1C#N VINOUPJXQKWKJA-UHFFFAOYSA-N 0.000 description 1
- OOCHUMUZANOKLG-UHFFFAOYSA-N 1-(4-methoxybenzoyl)aziridine-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1C(=O)N1C(C#N)C1 OOCHUMUZANOKLG-UHFFFAOYSA-N 0.000 description 1
- GULXNMXQFNMYAW-UHFFFAOYSA-N 1-(4-phenylbenzoyl)aziridine-2-carbonitrile Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)N1CC1C#N GULXNMXQFNMYAW-UHFFFAOYSA-N 0.000 description 1
- WGVIDSAKCVPXLS-UHFFFAOYSA-N 1-(7-oxabicyclo[2.2.1]heptane-3-carbonyl)aziridine-2-carbonitrile Chemical compound C1C(O2)CCC2C1C(=O)N1CC1C#N WGVIDSAKCVPXLS-UHFFFAOYSA-N 0.000 description 1
- JSZMWXVZJYVSJP-UHFFFAOYSA-N 1-(9h-xanthene-9-carbonyl)aziridine-2-carbonitrile Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)N1CC1C#N JSZMWXVZJYVSJP-UHFFFAOYSA-N 0.000 description 1
- UPJYPQAXUMJODP-UHFFFAOYSA-N 1-(anthracene-9-carbonyl)aziridine-2-carbonitrile Chemical compound C=12C=CC=CC2=CC2=CC=CC=C2C=1C(=O)N1CC1C#N UPJYPQAXUMJODP-UHFFFAOYSA-N 0.000 description 1
- BPTBTANSNLMOSH-UHFFFAOYSA-N 1-(cycloheptanecarbonyl)aziridine-2-carbonitrile Chemical compound C1C(C#N)N1C(=O)C1CCCCCC1 BPTBTANSNLMOSH-UHFFFAOYSA-N 0.000 description 1
- PMFRHTXYHJOLAB-UHFFFAOYSA-N 1-(cyclopropanecarbonyl)aziridine-2-carbonitrile Chemical compound C1C(C#N)N1C(=O)C1CC1 PMFRHTXYHJOLAB-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- LETMWZAQSHREGR-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)cyclopentanecarbonyl]aziridine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C1(C(=O)N2C(C2)C#N)CCCC1 LETMWZAQSHREGR-UHFFFAOYSA-N 0.000 description 1
- YXQMYZXUOFSENK-UHFFFAOYSA-N 1-[2-(1-acetylindol-3-yl)acetyl]aziridine-2-carbonitrile Chemical compound C12=CC=CC=C2N(C(=O)C)C=C1CC(=O)N1CC1C#N YXQMYZXUOFSENK-UHFFFAOYSA-N 0.000 description 1
- USVRPGCGGQRTFL-UHFFFAOYSA-N 1-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]-3-methylsulfonylurea Chemical compound CS(=O)(=O)NC(=O)NCC(=O)N1CC1C#N USVRPGCGGQRTFL-UHFFFAOYSA-N 0.000 description 1
- SKFHOUPUXBMASC-UHFFFAOYSA-N 1-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)NCC(=O)N1CC1C#N SKFHOUPUXBMASC-UHFFFAOYSA-N 0.000 description 1
- OJHPXJMOITVURJ-UHFFFAOYSA-N 1-[2-(phenylsulfanylamino)acetyl]aziridine-2-carbonitrile Chemical compound C1C(C#N)N1C(=O)CNSC1=CC=CC=C1 OJHPXJMOITVURJ-UHFFFAOYSA-N 0.000 description 1
- NWCWEXRJYVJLGU-UHFFFAOYSA-N 1-[2-[(2,5-dioxopyrrolidin-1-yl)amino]acetyl]aziridine-2-carbonitrile Chemical compound C1C(C#N)N1C(=O)CNN1C(=O)CCC1=O NWCWEXRJYVJLGU-UHFFFAOYSA-N 0.000 description 1
- BBZARUBLQZEQIB-UHFFFAOYSA-N 1-[3-(furan-2-yl)prop-2-enoyl]aziridine-2-carbonitrile Chemical compound C1C(C#N)N1C(=O)C=CC1=CC=CO1 BBZARUBLQZEQIB-UHFFFAOYSA-N 0.000 description 1
- ZJDRDTZQVOCKPI-UHFFFAOYSA-N 1-benzofuran-2-carbonyl chloride Chemical compound C1=CC=C2OC(C(=O)Cl)=CC2=C1 ZJDRDTZQVOCKPI-UHFFFAOYSA-N 0.000 description 1
- OWGJXSYVHQEVHS-UHFFFAOYSA-N 1-dichlorophosphorylethane Chemical compound CCP(Cl)(Cl)=O OWGJXSYVHQEVHS-UHFFFAOYSA-N 0.000 description 1
- YTXWLTAAWJGDSW-UHFFFAOYSA-N 1-formylaziridine-2-carbonitrile Chemical compound O=CN1CC1C#N YTXWLTAAWJGDSW-UHFFFAOYSA-N 0.000 description 1
- KLAQNTBUXCCZHC-UHFFFAOYSA-N 1-methyl-3-nitropyrazole Chemical compound CN1C=CC([N+]([O-])=O)=N1 KLAQNTBUXCCZHC-UHFFFAOYSA-N 0.000 description 1
- KTTHDBVMLIBUMC-UHFFFAOYSA-N 1-oxido-1-(pyridine-2-carbonyl)aziridin-1-ium-2-carbonitrile Chemical compound C=1C=CC=NC=1C(=O)[N+]1([O-])CC1C#N KTTHDBVMLIBUMC-UHFFFAOYSA-N 0.000 description 1
- OIOMJMFVZJZABO-UHFFFAOYSA-N 1-prop-2-ynoylaziridine-2-carbonitrile Chemical compound C#CC(=O)N1CC1C#N OIOMJMFVZJZABO-UHFFFAOYSA-N 0.000 description 1
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 1
- CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 1
- WQINSVOOIJDOLJ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetic acid Chemical compound C1=CC=C2C(=O)N(CC(=O)O)C(=O)C2=C1 WQINSVOOIJDOLJ-UHFFFAOYSA-N 0.000 description 1
- JGPIWNNFLKDTSR-UHFFFAOYSA-N 2-(2-oxopyrrolidin-1-yl)acetic acid Chemical compound OC(=O)CN1CCCC1=O JGPIWNNFLKDTSR-UHFFFAOYSA-N 0.000 description 1
- YWECCEXWKFHHQJ-UHFFFAOYSA-N 2-(4-chlorobenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(Cl)C=C1 YWECCEXWKFHHQJ-UHFFFAOYSA-N 0.000 description 1
- JGRMXPSUZIYDRR-UHFFFAOYSA-N 2-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)acetic acid Chemical compound OC(=O)CN1C(=O)CSC1=S JGRMXPSUZIYDRR-UHFFFAOYSA-N 0.000 description 1
- PCFFPRVWXSSCBI-UHFFFAOYSA-N 2-(acetylcarbamoylamino)acetic acid Chemical compound CC(=O)NC(=O)NCC(O)=O PCFFPRVWXSSCBI-UHFFFAOYSA-N 0.000 description 1
- DLLMHEDYJQACRM-UHFFFAOYSA-N 2-(carboxymethyldisulfanyl)acetic acid Chemical compound OC(=O)CSSCC(O)=O DLLMHEDYJQACRM-UHFFFAOYSA-N 0.000 description 1
- LTZMAQOKPJMBRZ-UHFFFAOYSA-N 2-(methanesulfonamido)acetic acid Chemical compound CS(=O)(=O)NCC(O)=O LTZMAQOKPJMBRZ-UHFFFAOYSA-N 0.000 description 1
- SHXTZVXDUILKNY-UHFFFAOYSA-N 2-(n-acetylanilino)acetic acid Chemical compound OC(=O)CN(C(=O)C)C1=CC=CC=C1 SHXTZVXDUILKNY-UHFFFAOYSA-N 0.000 description 1
- XPQCDYYJHJOAIC-UHFFFAOYSA-N 2-(naphthalene-2-carbonylamino)acetic acid Chemical compound C1=CC=CC2=CC(C(=O)NCC(=O)O)=CC=C21 XPQCDYYJHJOAIC-UHFFFAOYSA-N 0.000 description 1
- NXTJGIBOVGESBV-UHFFFAOYSA-N 2-(thiophene-2-carbonylamino)acetic acid Chemical compound OC(=O)CNC(=O)C1=CC=CS1 NXTJGIBOVGESBV-UHFFFAOYSA-N 0.000 description 1
- NSEWCAZRGRZTHU-UHFFFAOYSA-N 2-[(2,4-dichlorobenzoyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)C1=CC=C(Cl)C=C1Cl NSEWCAZRGRZTHU-UHFFFAOYSA-N 0.000 description 1
- ZCASHLUDUSAKNN-UHFFFAOYSA-N 2-[(2-acetamidoacetyl)amino]acetic acid Chemical compound CC(=O)NCC(=O)NCC(O)=O ZCASHLUDUSAKNN-UHFFFAOYSA-N 0.000 description 1
- VDNMXWRIILTOEY-UHFFFAOYSA-N 2-[(2-cyclohexylacetyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)CC1CCCCC1 VDNMXWRIILTOEY-UHFFFAOYSA-N 0.000 description 1
- RSHOGRPEOYNOBS-UHFFFAOYSA-N 2-[(2-methoxyacetyl)amino]acetic acid Chemical compound COCC(=O)NCC(O)=O RSHOGRPEOYNOBS-UHFFFAOYSA-N 0.000 description 1
- COYZIYOEXGRBHQ-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)C1=CC=C(Cl)C=C1 COYZIYOEXGRBHQ-UHFFFAOYSA-N 0.000 description 1
- SIEIOUWSTGWJGE-UHFFFAOYSA-N 2-[(4-methoxyphenyl)formamido]acetic acid Chemical compound COC1=CC=C(C(=O)NCC(O)=O)C=C1 SIEIOUWSTGWJGE-UHFFFAOYSA-N 0.000 description 1
- VDKFCCZUCXYILI-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]acetic acid Chemical compound CC1=CC=C(S(=O)(=O)NCC(O)=O)C=C1 VDKFCCZUCXYILI-UHFFFAOYSA-N 0.000 description 1
- SVXPSKKRNACRPB-UHFFFAOYSA-N 2-[acetyl(methyl)amino]acetic acid Chemical compound CC(=O)N(C)CC(O)=O SVXPSKKRNACRPB-UHFFFAOYSA-N 0.000 description 1
- SVZNKTDJVRIODX-UHFFFAOYSA-N 2-[benzenesulfonyl(propyl)amino]acetic acid Chemical compound CCCN(CC(O)=O)S(=O)(=O)C1=CC=CC=C1 SVZNKTDJVRIODX-UHFFFAOYSA-N 0.000 description 1
- CVVVAKVOCWNDLJ-UHFFFAOYSA-N 2-acetamido-2-cyclohexylacetic acid Chemical compound CC(=O)NC(C(O)=O)C1CCCCC1 CVVVAKVOCWNDLJ-UHFFFAOYSA-N 0.000 description 1
- OQUXDKMVCGSMPI-UHFFFAOYSA-N 2-acetamido-3-ethoxy-3-oxopropanoic acid Chemical compound CCOC(=O)C(C(O)=O)NC(C)=O OQUXDKMVCGSMPI-UHFFFAOYSA-N 0.000 description 1
- SYQTZIOAYGQFCE-UHFFFAOYSA-N 2-acetamidoacetyl chloride Chemical compound CC(=O)NCC(Cl)=O SYQTZIOAYGQFCE-UHFFFAOYSA-N 0.000 description 1
- AWLVTQRRKPBQEQ-UHFFFAOYSA-N 2-benzylsulfanylacetic acid Chemical compound OC(=O)CSCC1=CC=CC=C1 AWLVTQRRKPBQEQ-UHFFFAOYSA-N 0.000 description 1
- RGEPPBABZLNJNW-UHFFFAOYSA-N 2-butylsulfinyl-n-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]acetamide Chemical compound CCCCS(=O)CC(=O)NCC(=O)N1CC1C#N RGEPPBABZLNJNW-UHFFFAOYSA-N 0.000 description 1
- RMSRKYVNQYEPHO-UHFFFAOYSA-N 2-cyanoaziridine-1-carboxamide Chemical compound NC(=O)N1CC1C#N RMSRKYVNQYEPHO-UHFFFAOYSA-N 0.000 description 1
- HTCCQHKKWKMUMG-UHFFFAOYSA-N 2-ethoxypropanoyl chloride Chemical compound CCOC(C)C(Cl)=O HTCCQHKKWKMUMG-UHFFFAOYSA-N 0.000 description 1
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
- VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical compound CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 description 1
- QCXCIYPOMMIBHO-UHFFFAOYSA-N 2-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC1=NC=C(C(O)=O)S1 QCXCIYPOMMIBHO-UHFFFAOYSA-N 0.000 description 1
- DMVXVRUUBZGVTC-UHFFFAOYSA-N 2-methylbenzenecarbothioyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=S DMVXVRUUBZGVTC-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- JJVRWECYWMHJCY-UHFFFAOYSA-N 2-methylsulfonylbenzoyl chloride Chemical compound CS(=O)(=O)C1=CC=CC=C1C(Cl)=O JJVRWECYWMHJCY-UHFFFAOYSA-N 0.000 description 1
- ALNUOSXDMYFQNQ-UHFFFAOYSA-N 2-nitro-1,3-thiazole Chemical compound [O-][N+](=O)C1=NC=CS1 ALNUOSXDMYFQNQ-UHFFFAOYSA-N 0.000 description 1
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- SODZBMGDYKEZJG-UHFFFAOYSA-N 2-phenylcyclopropane-1-carbonyl chloride Chemical compound ClC(=O)C1CC1C1=CC=CC=C1 SODZBMGDYKEZJG-UHFFFAOYSA-N 0.000 description 1
- MOTOSAGBNXXRRE-UHFFFAOYSA-N 2-phenylsulfanylacetic acid Chemical compound OC(=O)CSC1=CC=CC=C1 MOTOSAGBNXXRRE-UHFFFAOYSA-N 0.000 description 1
- TWOLQIUHVMTAAE-UHFFFAOYSA-N 2-phenylsulfanylacetyl chloride Chemical compound ClC(=O)CSC1=CC=CC=C1 TWOLQIUHVMTAAE-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 1
- DXXHRZUOTPMGEH-UHFFFAOYSA-N 3-(1,3-dioxoisoindol-2-yl)propanoic acid Chemical compound C1=CC=C2C(=O)N(CCC(=O)O)C(=O)C2=C1 DXXHRZUOTPMGEH-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- VBLZMFWZOCKETH-UHFFFAOYSA-N 3-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NCC(=O)N1CC1C#N VBLZMFWZOCKETH-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- QHMINZNDPKXLOS-UHFFFAOYSA-N 3-[ethoxycarbonyl(methyl)amino]propanoic acid Chemical compound CCOC(=O)N(C)CCC(O)=O QHMINZNDPKXLOS-UHFFFAOYSA-N 0.000 description 1
- FYWDUQCSMYWUHV-UHFFFAOYSA-N 3-chloro-5-hydroxypentan-2-one Chemical compound CC(=O)C(Cl)CCO FYWDUQCSMYWUHV-UHFFFAOYSA-N 0.000 description 1
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical group ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 description 1
- MXMJHNGIWGMNIG-UHFFFAOYSA-N 3-methylsulfanylpyridazine Chemical compound CSC1=CC=CN=N1 MXMJHNGIWGMNIG-UHFFFAOYSA-N 0.000 description 1
- GAGIHZFTFKBBDR-UHFFFAOYSA-N 3-methylsulfonylpyridazine Chemical compound CS(=O)(=O)C1=CC=CN=N1 GAGIHZFTFKBBDR-UHFFFAOYSA-N 0.000 description 1
- RUEGAVIENIPHGK-UHFFFAOYSA-N 3-phenylimidazolidine-2,4-dione Chemical compound O=C1CNC(=O)N1C1=CC=CC=C1 RUEGAVIENIPHGK-UHFFFAOYSA-N 0.000 description 1
- FQXQBFUUVCDIRK-UHFFFAOYSA-N 3-trifluoromethylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C(F)(F)F)=C1 FQXQBFUUVCDIRK-UHFFFAOYSA-N 0.000 description 1
- XILORGWKMLOGKF-UHFFFAOYSA-N 4-(diethylamino)-4-oxobutanoic acid Chemical compound CCN(CC)C(=O)CCC(O)=O XILORGWKMLOGKF-UHFFFAOYSA-N 0.000 description 1
- UGJDXRVQCYBXAJ-UHFFFAOYSA-N 4-(dimethylamino)benzoyl chloride Chemical compound CN(C)C1=CC=C(C(Cl)=O)C=C1 UGJDXRVQCYBXAJ-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- BOZHPKGNNJPZKV-UHFFFAOYSA-N 4-benzamidobutanoic acid Chemical compound OC(=O)CCCNC(=O)C1=CC=CC=C1 BOZHPKGNNJPZKV-UHFFFAOYSA-N 0.000 description 1
- USEDMAWWQDFMFY-UHFFFAOYSA-N 4-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)C=C1 USEDMAWWQDFMFY-UHFFFAOYSA-N 0.000 description 1
- ADFVYWCDAKWKPH-UHFFFAOYSA-N 4-ethoxycarbonylbenzoic acid Chemical compound CCOC(=O)C1=CC=C(C(O)=O)C=C1 ADFVYWCDAKWKPH-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- DYYLCPSSSFWEEA-UHFFFAOYSA-N 4-methylbenzenesulfinyl chloride Chemical compound CC1=CC=C(S(Cl)=O)C=C1 DYYLCPSSSFWEEA-UHFFFAOYSA-N 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- HHGZQZULOHYEOH-UHFFFAOYSA-N 6-chloropyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)N=N1 HHGZQZULOHYEOH-UHFFFAOYSA-N 0.000 description 1
- UXYLOINHCQMHHY-UHFFFAOYSA-N 6-methylpyridine-2-carbonyl chloride Chemical compound CC1=CC=CC(C(Cl)=O)=N1 UXYLOINHCQMHHY-UHFFFAOYSA-N 0.000 description 1
- LTUUGSGSUZRPRV-UHFFFAOYSA-N 6-methylpyridine-2-carboxylic acid Chemical compound CC1=CC=CC(C(O)=O)=N1 LTUUGSGSUZRPRV-UHFFFAOYSA-N 0.000 description 1
- HNDGKCCVVLYJDF-UHFFFAOYSA-N 6-methylsulfanylpyridazine-3-carboxylic acid Chemical compound CSC1=CC=C(C(O)=O)N=N1 HNDGKCCVVLYJDF-UHFFFAOYSA-N 0.000 description 1
- YPWFNLSXQIGJCK-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]heptane Chemical group C1CC2CCC1O2 YPWFNLSXQIGJCK-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- IFYATEIGOYKKKS-KYZUINATSA-N CC(=O)NC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CC(=O)NC[C@H]1CC[C@H](C(O)=O)CC1 IFYATEIGOYKKKS-KYZUINATSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 241000006460 Cyana Species 0.000 description 1
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- UUCUQJHYUPXDHN-UHFFFAOYSA-N N-Acetylindole Chemical compound C1=CC=C2N(C(=O)C)C=CC2=C1 UUCUQJHYUPXDHN-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- OTCCIMWXFLJLIA-UHFFFAOYSA-N N-acetyl-DL-aspartic acid Natural products CC(=O)NC(C(O)=O)CC(O)=O OTCCIMWXFLJLIA-UHFFFAOYSA-N 0.000 description 1
- OTCCIMWXFLJLIA-BYPYZUCNSA-N N-acetyl-L-aspartic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-BYPYZUCNSA-N 0.000 description 1
- KSMRODHGGIIXDV-YFKPBYRVSA-N N-acetyl-L-glutamine Chemical compound CC(=O)N[C@H](C(O)=O)CCC(N)=O KSMRODHGGIIXDV-YFKPBYRVSA-N 0.000 description 1
- GNMSLDIYJOSUSW-LURJTMIESA-N N-acetyl-L-proline Chemical compound CC(=O)N1CCC[C@H]1C(O)=O GNMSLDIYJOSUSW-LURJTMIESA-N 0.000 description 1
- 108010021523 N-acetylglycylglycine Proteins 0.000 description 1
- XUYPXLNMDZIRQH-UHFFFAOYSA-N N-acetylmethionine Chemical compound CSCCC(C(O)=O)NC(C)=O XUYPXLNMDZIRQH-UHFFFAOYSA-N 0.000 description 1
- CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 1
- UGJBHEZMOKVTIM-UHFFFAOYSA-N N-formylglycine Chemical compound OC(=O)CNC=O UGJBHEZMOKVTIM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- MNYZGNSHBPLAFN-UHFFFAOYSA-N Picolinoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=N1 MNYZGNSHBPLAFN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 101150081514 Spef2 gene Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- MIYSGPLECJTXQX-UHFFFAOYSA-N [1-(2-cyanoaziridine-1-carbonyl)cyclopropyl]methylurea Chemical compound C1C(C#N)N1C(=O)C1(CNC(=O)N)CC1 MIYSGPLECJTXQX-UHFFFAOYSA-N 0.000 description 1
- FTWSUPKOCYVCNX-UHFFFAOYSA-N [2-[[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]carbamoyl]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NCC(=O)N1C(C#N)C1 FTWSUPKOCYVCNX-UHFFFAOYSA-N 0.000 description 1
- PCZGMEKUCFKUTL-UHFFFAOYSA-N [4-(2-cyanoaziridine-1-carbonyl)phenyl]urea Chemical compound C1=CC(NC(=O)N)=CC=C1C(=O)N1C(C#N)C1 PCZGMEKUCFKUTL-UHFFFAOYSA-N 0.000 description 1
- JPRWTCXQSONAKR-BTUGKURYSA-N [4-[(2s)-2-acetamido-3-(2-cyanoaziridin-1-yl)-3-oxopropyl]phenyl] acetate Chemical compound C([C@H](NC(=O)C)C(=O)N1C(C1)C#N)C1=CC=C(OC(C)=O)C=C1 JPRWTCXQSONAKR-BTUGKURYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- WDSCBUNMANHPFH-UHFFFAOYSA-N acexamic acid Chemical compound CC(=O)NCCCCCC(O)=O WDSCBUNMANHPFH-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 150000001601 aromatic carbocyclic compounds Chemical class 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000001185 bone marrow Anatomy 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
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- NLCIYDBRSJQKTO-UHFFFAOYSA-N chloroform;cyclohexane;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl.C1CCCCC1 NLCIYDBRSJQKTO-UHFFFAOYSA-N 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009838 combustion analysis Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- SXIWNIQDOJKDGB-UHFFFAOYSA-N dichloro-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound ClP(Cl)(=S)C1=CC=CC=C1 SXIWNIQDOJKDGB-UHFFFAOYSA-N 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 1
- TXFOLHZMICYNRM-UHFFFAOYSA-N dichlorophosphoryloxybenzene Chemical compound ClP(Cl)(=O)OC1=CC=CC=C1 TXFOLHZMICYNRM-UHFFFAOYSA-N 0.000 description 1
- ILXZMTJXXHNZJS-UHFFFAOYSA-N diethyl hydrogen phosphate;hydrochloride Chemical compound Cl.CCOP(O)(=O)OCC ILXZMTJXXHNZJS-UHFFFAOYSA-N 0.000 description 1
- YBBUMZUSUMRUKT-UHFFFAOYSA-N dimethyl hydrogen phosphate hydrochloride Chemical compound Cl.COP(O)(=O)OC YBBUMZUSUMRUKT-UHFFFAOYSA-N 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000000913 erythropoietic effect Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- YYLWXDIGYFPUSK-ONEGZZNKSA-N ethyl (e)-4-chloro-4-oxobut-2-enoate Chemical compound CCOC(=O)\C=C\C(Cl)=O YYLWXDIGYFPUSK-ONEGZZNKSA-N 0.000 description 1
- JASFTUXTUYZCBW-UHFFFAOYSA-N ethyl dihydrogen phosphate;dihydrochloride Chemical compound Cl.Cl.CCOP(O)(O)=O JASFTUXTUYZCBW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LEDGBSRLPYKDPY-UHFFFAOYSA-N hexanethioyl chloride Chemical compound CCCCCC(Cl)=S LEDGBSRLPYKDPY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229960001438 immunostimulant agent Drugs 0.000 description 1
- 239000003022 immunostimulating agent Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical compound NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002493 microarray Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- WXPLRSVMGRAIGW-UHFFFAOYSA-N n-(1,3-thiazol-2-yl)acetamide Chemical compound CC(=O)NC1=NC=CS1 WXPLRSVMGRAIGW-UHFFFAOYSA-N 0.000 description 1
- PJKDZOOEPLTBIF-LASWEOPPSA-N n-[(2s)-3-(1-acetylimidazol-4-yl)-1-(2-cyanoaziridin-1-yl)-1-oxopropan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)C(=O)N1C(C1)C#N)C1=CN(C(C)=O)C=N1 PJKDZOOEPLTBIF-LASWEOPPSA-N 0.000 description 1
- RHWMENHYZHSQGK-UHFFFAOYSA-N n-[1-(2-cyanoaziridin-1-yl)-1-oxo-3-phenylpropan-2-yl]acetamide Chemical compound C1C(C#N)N1C(=O)C(NC(=O)C)CC1=CC=CC=C1 RHWMENHYZHSQGK-UHFFFAOYSA-N 0.000 description 1
- JAILXKIVQUHDAP-UHFFFAOYSA-N n-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NCC(=O)N1C(C#N)C1 JAILXKIVQUHDAP-UHFFFAOYSA-N 0.000 description 1
- KXOUIWXQHOALPK-UHFFFAOYSA-N n-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]-4-phenylbenzamide Chemical compound C1C(C#N)N1C(=O)CNC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 KXOUIWXQHOALPK-UHFFFAOYSA-N 0.000 description 1
- LWVWMGNIURPVAK-UHFFFAOYSA-N n-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]-6-methylpyridine-2-carboxamide Chemical compound CC1=CC=CC(C(=O)NCC(=O)N2C(C2)C#N)=N1 LWVWMGNIURPVAK-UHFFFAOYSA-N 0.000 description 1
- QNRXYXNBFQBMDH-UHFFFAOYSA-N n-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]acetamide Chemical compound CC(=O)NCC(=O)N1CC1C#N QNRXYXNBFQBMDH-UHFFFAOYSA-N 0.000 description 1
- QBODQHIDBQDKST-UHFFFAOYSA-N n-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]pyridine-2-carboxamide Chemical compound C1C(C#N)N1C(=O)CNC(=O)C1=CC=CC=N1 QBODQHIDBQDKST-UHFFFAOYSA-N 0.000 description 1
- MMIROGAREFWNKF-UHFFFAOYSA-N n-[4-(2-cyanoaziridin-1-yl)-4-oxobutyl]acetamide Chemical compound CC(=O)NCCCC(=O)N1CC1C#N MMIROGAREFWNKF-UHFFFAOYSA-N 0.000 description 1
- JDQQBTCALOGQEO-UHFFFAOYSA-N n-[4-(2-cyanoaziridin-1-yl)-4-oxobutyl]benzamide Chemical compound C1C(C#N)N1C(=O)CCCNC(=O)C1=CC=CC=C1 JDQQBTCALOGQEO-UHFFFAOYSA-N 0.000 description 1
- JNRSLIOSIKQRML-UHFFFAOYSA-N n-[6-(2-cyanoaziridin-1-yl)-6-oxohexyl]acetamide Chemical compound CC(=O)NCCCCCC(=O)N1CC1C#N JNRSLIOSIKQRML-UHFFFAOYSA-N 0.000 description 1
- DRTPFJKYZZXLEG-UHFFFAOYSA-N n-[[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]carbamoyl]acetamide Chemical compound CC(=O)NC(=O)NCC(=O)N1CC1C#N DRTPFJKYZZXLEG-UHFFFAOYSA-N 0.000 description 1
- BTPVNDYWQQXJKH-UHFFFAOYSA-N n-benzyl-n-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]acetamide Chemical compound C=1C=CC=CC=1CN(C(=O)C)CC(=O)N1CC1C#N BTPVNDYWQQXJKH-UHFFFAOYSA-N 0.000 description 1
- FRJPEULACIOLQG-UHFFFAOYSA-N n-cyclohexyl-n-(cyclohexylcarbamoyl)-4-oxopentanamide Chemical compound C1CCCCC1NC(=O)N(C(=O)CCC(=O)C)C1CCCCC1 FRJPEULACIOLQG-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- NRSCPTLHWVWLLH-UHFFFAOYSA-N p-methylhippuric acid Chemical compound CC1=CC=C(C(=O)NCC(O)=O)C=C1 NRSCPTLHWVWLLH-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 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
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical compound OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- PSAYJRPASWETSH-UHFFFAOYSA-N pyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC=N1 PSAYJRPASWETSH-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003450 sulfenic acids Chemical class 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
- C07D203/18—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carboxylic acids, or by sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
- C07D203/24—Sulfur atoms
-
- 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
- C07D231/14—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 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
- C07D231/16—Halogen atoms or nitro radicals
-
- 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
- C07D231/14—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 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- 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
- C07D231/14—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 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/564—Three-membered rings
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F42—AMMUNITION; BLASTING
- F42B—EXPLOSIVE CHARGES, e.g. FOR BLASTING, FIREWORKS, AMMUNITION
- F42B3/00—Blasting cartridges, i.e. case and explosive
- F42B3/087—Flexible or deformable blasting cartridges, e.g. bags or hoses for slurries
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772731264 DE2731264A1 (de) | 1977-07-11 | 1977-07-11 | Neue 1-acyl-2-cyanaziridine, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische zubereitungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO782399L true NO782399L (no) | 1979-01-12 |
Family
ID=6013651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO782399A NO782399L (no) | 1977-07-11 | 1978-07-10 | Fremgangsmaate ved fremstilling av 1-acyl-2-cyanaziridiner |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4267174A (cs) |
| JP (1) | JPS5436254A (cs) |
| AT (1) | AT356663B (cs) |
| AU (2) | AU3782678A (cs) |
| BE (1) | BE868796A (cs) |
| CA (1) | CA1086309A (cs) |
| CS (1) | CS208656B2 (cs) |
| DD (1) | DD137710A5 (cs) |
| DE (1) | DE2731264A1 (cs) |
| DK (1) | DK306978A (cs) |
| ES (1) | ES471512A1 (cs) |
| FI (1) | FI782157A7 (cs) |
| FR (1) | FR2397403A1 (cs) |
| GB (1) | GB1594079A (cs) |
| HU (1) | HU179428B (cs) |
| IL (1) | IL55109A (cs) |
| IT (1) | IT1096910B (cs) |
| LU (1) | LU79937A1 (cs) |
| NL (1) | NL7807276A (cs) |
| NO (1) | NO782399L (cs) |
| NZ (1) | NZ187794A (cs) |
| PL (1) | PL126639B1 (cs) |
| PT (1) | PT68263A (cs) |
| SE (1) | SE7807642L (cs) |
| SU (1) | SU1077565A3 (cs) |
| ZA (1) | ZA783829B (cs) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2906603A1 (de) | 1979-02-21 | 1980-09-04 | Boehringer Mannheim Gmbh | N-substituierte aziridin-2-carbonsaeurederivate, verfahren zu deren herstellung sowie diese substanzen enthaltende arzneimittel |
| US4393000A (en) * | 1979-12-12 | 1983-07-12 | Mitsui Toatsu Chemicals, Inc. | Cyclization process for producing aziridine-2-carboxylic acid or its salts |
| US4925835A (en) * | 1986-05-01 | 1990-05-15 | Sloan-Kettering Institute For Cancer Research | Aziridinyl putrescine containing compositions and their uses in treating prostate cancer |
| US6982263B2 (en) * | 2001-06-08 | 2006-01-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Nitriles useful as reversible inhibitors of cysteine proteases |
| ES2295816T3 (es) * | 2003-01-14 | 2008-04-16 | Arena Pharmaceuticals, Inc. | Derivados arilo y heteroarilo 1,2,3-trisustituidos como moduladores del metabolismo, y profilaxis y tratamiento de transtornos relacionados con los mismos, tales como la diabetes y la hiperglucemia. |
| DE602004017703D1 (de) * | 2003-02-24 | 2008-12-24 | Arena Pharm Inc | Phenyl- und pyridylpiperidinderivate als modulatoren des glucose-metabolismus |
| AR045047A1 (es) * | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| MXPA06014129A (es) * | 2004-06-04 | 2007-03-07 | Arena Pharm Inc | Derivados de arilo y heteroarilo sustituidos como moduladores del metabolismo y profilaxis y tratamiento de trastornos relacionados con los mismos. |
| MY148521A (en) * | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| DOP2006000010A (es) | 2005-01-10 | 2006-07-31 | Arena Pharm Inc | Procedimiento para preparar eteres aromáticos |
| ES2326391T3 (es) * | 2005-09-16 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Moduladores del metabolismo y el tratamiento de trastornos relacionados con el mismo. |
| TW200811140A (en) * | 2006-07-06 | 2008-03-01 | Arena Pharm Inc | Modulators of metabolism and the treatment of disorders related thereto |
| TW200811147A (en) * | 2006-07-06 | 2008-03-01 | Arena Pharm Inc | Modulators of metabolism and the treatment of disorders related thereto |
| JP5856980B2 (ja) | 2010-01-27 | 2016-02-10 | アリーナ ファーマシューティカルズ， インコーポレイテッド | （Ｒ）−２−（７−（４−シクロペンチル−３−（トリフルオロメチル）ベンジルオキシ）−１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドール−３−イル）酢酸およびその塩の調製のためのプロセス |
| WO2012040279A1 (en) | 2010-09-22 | 2012-03-29 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| MX386419B (es) | 2015-01-06 | 2025-03-18 | Arena Pharm Inc | Metodos de condiciones de tratamiento relacionadas con el receptor s1p1. |
| EP3310760B8 (en) | 2015-06-22 | 2022-10-19 | Arena Pharmaceuticals, Inc. | Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid for use in s1p1 receptor-associated disorders |
| AU2018220521A1 (en) | 2017-02-16 | 2019-09-05 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| ES2987794T3 (es) | 2018-06-06 | 2024-11-18 | Arena Pharm Inc | Procedimientos de tratamiento de afecciones relacionadas con el receptor S1P1 |
| LV15518A (lv) * | 2019-02-18 | 2020-08-20 | Latvijas Organiskās Sintēzes Institūts | Aziridīn-2-karboksamīda atvasinājumi kā tioredoksīnreduktāzes inhibitori ar pretvēža un pretmetastatisku iedarbību un to sintēze |
| EP4087651A1 (en) * | 2020-01-10 | 2022-11-16 | Uniwersytet Jagiellonski | Aromatic sulphonamides derivatives that inhibits pdi a1, their synthesis and use |
| EP4087650A1 (en) * | 2020-01-10 | 2022-11-16 | Uniwersytet Jagiellonski | Aromatic sulphonamides derivatives that inhibits pdi a1, their synthesis and use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD110492A1 (cs) * | 1974-03-21 | 1974-12-20 | ||
| JPS5932772B2 (ja) * | 1974-09-21 | 1984-08-10 | 旭光学工業 （株） | 照射光走査装置 |
| DE2528460A1 (de) * | 1975-06-26 | 1977-01-13 | Boehringer Mannheim Gmbh | Verwendung von l-carboxamido-2- cyan-aziridin als immunstimulans |
-
1977
- 1977-07-11 DE DE19772731264 patent/DE2731264A1/de not_active Withdrawn
-
1978
- 1978-05-17 GB GB20099/78A patent/GB1594079A/en not_active Expired
- 1978-06-16 US US05/916,389 patent/US4267174A/en not_active Expired - Lifetime
- 1978-07-04 SU SU782631500A patent/SU1077565A3/ru active
- 1978-07-04 CA CA306,740A patent/CA1086309A/en not_active Expired
- 1978-07-04 FI FI782157A patent/FI782157A7/fi not_active Application Discontinuation
- 1978-07-04 ZA ZA783829A patent/ZA783829B/xx unknown
- 1978-07-05 NL NL7807276A patent/NL7807276A/xx not_active Application Discontinuation
- 1978-07-05 PL PL1978208195A patent/PL126639B1/pl unknown
- 1978-07-06 DD DD78206567A patent/DD137710A5/xx unknown
- 1978-07-06 ES ES471512A patent/ES471512A1/es not_active Expired
- 1978-07-06 BE BE189121A patent/BE868796A/xx unknown
- 1978-07-06 AU AU37826/78A patent/AU3782678A/en active Granted
- 1978-07-06 AU AU37826/78A patent/AU519219B2/en not_active Expired
- 1978-07-07 DK DK783069A patent/DK306978A/da not_active Application Discontinuation
- 1978-07-07 IT IT25474/78A patent/IT1096910B/it active
- 1978-07-07 NZ NZ187794A patent/NZ187794A/xx unknown
- 1978-07-07 CS CS784544A patent/CS208656B2/cs unknown
- 1978-07-07 LU LU79937A patent/LU79937A1/de unknown
- 1978-07-07 SE SE7807642A patent/SE7807642L/xx unknown
- 1978-07-07 PT PT68263A patent/PT68263A/pt unknown
- 1978-07-09 IL IL55109A patent/IL55109A/xx unknown
- 1978-07-10 NO NO782399A patent/NO782399L/no unknown
- 1978-07-10 HU HU78BO1723A patent/HU179428B/hu unknown
- 1978-07-10 FR FR7820468A patent/FR2397403A1/fr not_active Withdrawn
- 1978-07-10 AT AT496478A patent/AT356663B/de not_active IP Right Cessation
- 1978-07-11 JP JP8364578A patent/JPS5436254A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL55109A (en) | 1982-07-30 |
| PT68263A (de) | 1978-08-01 |
| DD137710A5 (de) | 1979-09-19 |
| IT1096910B (it) | 1985-08-26 |
| CA1086309A (en) | 1980-09-23 |
| IL55109A0 (en) | 1978-09-29 |
| ZA783829B (en) | 1980-03-26 |
| NZ187794A (en) | 1980-05-08 |
| GB1594079A (en) | 1981-07-30 |
| AU3782678A (en) | 1980-01-10 |
| AU3782578A (en) | 1980-01-10 |
| NL7807276A (nl) | 1979-01-15 |
| IT7825474A0 (it) | 1978-07-07 |
| ATA496478A (de) | 1979-10-15 |
| LU79937A1 (de) | 1980-02-14 |
| JPS5436254A (en) | 1979-03-16 |
| PL126639B1 (en) | 1983-08-31 |
| AT356663B (de) | 1980-05-12 |
| FR2397403A1 (fr) | 1979-02-09 |
| HU179428B (en) | 1982-10-28 |
| DE2731264A1 (de) | 1979-02-01 |
| AU519219B2 (en) | 1981-11-19 |
| BE868796A (fr) | 1979-01-08 |
| ES471512A1 (es) | 1979-10-01 |
| DK306978A (da) | 1979-01-12 |
| SU1077565A3 (ru) | 1984-02-29 |
| CS208656B2 (en) | 1981-09-15 |
| PL208195A1 (cs) | 1980-03-24 |
| FI782157A7 (fi) | 1979-01-12 |
| SE7807642L (sv) | 1979-03-14 |
| US4267174A (en) | 1981-05-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO782399L (no) | Fremgangsmaate ved fremstilling av 1-acyl-2-cyanaziridiner | |
| US5847155A (en) | Aromatic pyrrolidine amide prolyl endopeptidase inhibitors | |
| NO892982L (no) | Tetrahydro-1-benz-(c,d)-indolpropionsyre-sulfonamider. | |
| KR20010101675A (ko) | 2ｈ-프탈라진-1-온 유도체 및 그 유도체를 유효 성분으로하는 약제 | |
| NO179867B (no) | Sulfonamido- og sulfonamidokarbonyl-pyridin-2-karboksylsyreamider og anvendelse av forbindelsene som legemidler | |
| CA3197619A1 (en) | Benzylamine or benzyl alcohol derivative and use thereof | |
| EP0295049B1 (en) | Thiophene sulfonamide antiglaucoma agents | |
| WO2023143034A1 (zh) | 一种吡啶并咪唑类衍生物及其制备方法与应用 | |
| NO773377L (no) | Fremgangsmaate ved fremstilling av 1-(n-acyl-carbamoyl)-2-cyanaziridiner | |
| KR930006776B1 (ko) | 치환된 이속사졸 유도체의 제조방법 | |
| NO180085B (no) | Acylsulfonamido- og sulfonamidopyridin-2-karboksylsyreestere og deres anvendelse som legemidler | |
| EP0371342B1 (de) | 2-Halogensubstituierte N-Indolylethyl-sulfonsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln | |
| CN111793011B (zh) | 一种苯乙烯砜类nlrp3炎性小体抑制剂及其制备方法与应用 | |
| NO155097B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk aktivt n-(1'-allyl-2'-pyrrolidinylmethyl)-2-methoxy-4-amino-5-methylsulfamoylbenzamid. | |
| NO792510L (no) | Fremgangsmaate ved fremstilling av oxadiazolotriazin-derivater | |
| JPH04225954A (ja) | アミド化合物、その医薬用途および新規１−置換ピロリジンメチルアミン類 | |
| CS252828B2 (en) | Method of n,3-disubstituted 2-oxindole-1-carboxamides production | |
| JPS5833222B2 (ja) | 新規ジペプチド類 | |
| NO841217L (no) | Fremgangsmaate til fremstilling av beta-oxo-alfa-carbamoyl-pyrrolpropionitriler | |
| NO151323B (no) | Analogifremgangsmaate til fremstilling av et terapeutisk aktivt n-(2-tienyl)-2-okso-2,3-dihydro-benzo(b)tiofen-3-karboksamid | |
| NO157697B (no) | Analogifremgangsmte ved fremstilling av ikke-steroidale forbindelser med anti-inflammatorisk og analgesisk effekt. | |
| WO1991013868A1 (de) | Phenylthioalkylcarbonsäure-derivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel | |
| CH636607A5 (en) | 1-(N-Acylcarbamoyl)-2-cyanoaziridines having cancerostatic and immunostimulatory effects, and processes for the preparation thereof | |
| JPS5832871A (ja) | アリ−ルチアゾリジン化合物 | |
| NO810134L (no) | Fremgangsmaate for fremstilling av fysiologisk aktive pyrrolderivater |