PH26458A - Benzoxazol and benzothiazolamine derivatives useful as anti-anoxic agents - Google Patents
Benzoxazol and benzothiazolamine derivatives useful as anti-anoxic agents Download PDFInfo
- Publication number
- PH26458A PH26458A PH33124A PH33124A PH26458A PH 26458 A PH26458 A PH 26458A PH 33124 A PH33124 A PH 33124A PH 33124 A PH33124 A PH 33124A PH 26458 A PH26458 A PH 26458A
- Authority
- PH
- Philippines
- Prior art keywords
- formula
- parts
- radical
- alkyl
- aryl
- Prior art date
Links
- 230000000496 anti-anoxic effect Effects 0.000 title claims abstract description 14
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title description 3
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 title description 3
- -1 aryl C2-6 alkenyl Chemical group 0.000 claims abstract description 112
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 20
- 239000004480 active ingredient Substances 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 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 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 150000001721 carbon Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 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 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 206010021143 Hypoxia Diseases 0.000 claims description 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 206010002660 Anoxia Diseases 0.000 claims description 5
- 241000976983 Anoxia Species 0.000 claims description 5
- 230000007953 anoxia Effects 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000007910 systemic administration Methods 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims 2
- 241000252233 Cyprinus carpio Species 0.000 claims 1
- 241001272567 Hominoidea Species 0.000 claims 1
- 101100022451 Mus musculus Mbnl3 gene Proteins 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 239000011717 all-trans-retinol Substances 0.000 claims 1
- 235000019169 all-trans-retinol Nutrition 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 101150115538 nero gene Proteins 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
- 230000000141 anti-hypoxic effect Effects 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 2
- SPLBDRVSAMREPT-UHFFFAOYSA-N 1,3-benzothiazol-2-amine;1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1.C1=CC=C2SC(N)=NC2=C1 SPLBDRVSAMREPT-UHFFFAOYSA-N 0.000 abstract description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 description 145
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 123
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 40
- 239000003480 eluent Substances 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 37
- 229960001701 chloroform Drugs 0.000 description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- 150000003254 radicals Chemical class 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 27
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 26
- 238000003756 stirring Methods 0.000 description 26
- 239000000543 intermediate Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 238000001816 cooling Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 16
- 238000007792 addition Methods 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- 229940083608 sodium hydroxide Drugs 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 150000002540 isothiocyanates Chemical class 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000012258 stirred mixture Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 229950005499 carbon tetrachloride Drugs 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- CJHRMIZAODWVDU-UHFFFAOYSA-N ethyl 3-(methylamino)piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCCC(NC)C1 CJHRMIZAODWVDU-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 5
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- LVQFHDAKZHGEAJ-UHFFFAOYSA-M 4-methylbenzenesulfonate Chemical compound [CH2]C1=CC=C(S([O-])(=O)=O)C=C1 LVQFHDAKZHGEAJ-UHFFFAOYSA-M 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 238000007126 N-alkylation reaction Methods 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 125000004311 dioxin-2-yl group Chemical group [H]C1=C([H])OC(*)=C([H])O1 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- 150000004682 monohydrates Chemical class 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- UBRDNIYFQMHSEA-UHFFFAOYSA-N ethyl 4-(butylamino)piperidine-1-carboxylate Chemical compound CCCCNC1CCN(C(=O)OCC)CC1 UBRDNIYFQMHSEA-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000007954 hypoxia Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(II) oxide Inorganic materials [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 3
- DCXFTFFFMMBKEO-UHFFFAOYSA-N n-methyl-n-pyrrolidin-3-yl-1,3-benzoxazol-2-amine Chemical compound N=1C2=CC=CC=C2OC=1N(C)C1CCNC1 DCXFTFFFMMBKEO-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- BTANRVKWQNVYAZ-SCSAIBSYSA-N (2R)-butan-2-ol Chemical compound CC[C@@H](C)O BTANRVKWQNVYAZ-SCSAIBSYSA-N 0.000 description 2
- AKWLXYPVWJFZMG-QMMMGPOBSA-N (2s)-3-(4-fluorophenoxy)propane-1,2-diol Chemical compound OC[C@H](O)COC1=CC=C(F)C=C1 AKWLXYPVWJFZMG-QMMMGPOBSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- QMWAQHTYWDAKBC-UHFFFAOYSA-N 2-[(3-chlorophenoxy)methyl]oxirane Chemical compound ClC1=CC=CC(OCC2OC2)=C1 QMWAQHTYWDAKBC-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- KWHINWNDDFVYJS-UHFFFAOYSA-N 4-(4-fluorophenoxy)cyclohexan-1-ol Chemical compound C1CC(O)CCC1OC1=CC=C(F)C=C1 KWHINWNDDFVYJS-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- GRIATXVEXOFBGO-UHFFFAOYSA-N 4-methyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC=CC2=C1N=C(N)S2 GRIATXVEXOFBGO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 125000006309 butyl amino group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- SGJSQQLUMMGQOS-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#C[C]1CCCCC1 SGJSQQLUMMGQOS-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- ANBZWDBEKOZNHY-UHFFFAOYSA-N ethanol;oxalic acid Chemical compound CCO.OC(=O)C(O)=O ANBZWDBEKOZNHY-UHFFFAOYSA-N 0.000 description 2
- GDTPFDPNHLKMQG-UHFFFAOYSA-N ethyl 3-(1,3-benzoxazol-2-ylamino)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1NC1=NC2=CC=CC=C2O1 GDTPFDPNHLKMQG-UHFFFAOYSA-N 0.000 description 2
- CIYOQPCBOIRZHQ-UHFFFAOYSA-N ethyl 4-[anilino(methanethioyl)amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N(C=S)NC1=CC=CC=C1 CIYOQPCBOIRZHQ-UHFFFAOYSA-N 0.000 description 2
- LKKAWMNEPUOSKW-UHFFFAOYSA-N ethyl 4-isothiocyanatopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(N=C=S)CC1 LKKAWMNEPUOSKW-UHFFFAOYSA-N 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 231100000225 lethality Toxicity 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- GGVWYFBRIAYWMW-UHFFFAOYSA-N n-methyl-n-piperidin-3-yl-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1N(C)C1CCCNC1 GGVWYFBRIAYWMW-UHFFFAOYSA-N 0.000 description 2
- GUPVGZMYVKFAJU-UHFFFAOYSA-N n-methyl-n-piperidin-4-yl-1,3-benzoxazol-2-amine Chemical compound N=1C2=CC=CC=C2OC=1N(C)C1CCNCC1 GUPVGZMYVKFAJU-UHFFFAOYSA-N 0.000 description 2
- SRPKOCIOQSJHLI-UHFFFAOYSA-N n-piperidin-4-yl-1,3-benzoxazol-2-amine Chemical compound C1CNCCC1NC1=NC2=CC=CC=C2O1 SRPKOCIOQSJHLI-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229940100688 oral solution Drugs 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 229960003415 propylparaben Drugs 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 238000010956 selective crystallization Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- CEZOORGGKZLLAO-UHFFFAOYSA-N (2-phenylcyclopropyl)methanol Chemical compound OCC1CC1C1=CC=CC=C1 CEZOORGGKZLLAO-UHFFFAOYSA-N 0.000 description 1
- CGWDABYOHPEOAD-VIFPVBQESA-N (2r)-2-[(4-fluorophenoxy)methyl]oxirane Chemical compound C1=CC(F)=CC=C1OC[C@@H]1OC1 CGWDABYOHPEOAD-VIFPVBQESA-N 0.000 description 1
- VZWWWGRCXYOHIG-BTJKTKAUSA-N (Z)-but-2-enedioic acid N-methyl-N-[1-(1-phenylbut-3-enyl)piperidin-4-yl]-1,3-benzothiazol-2-amine Chemical compound OC(=O)\C=C/C(O)=O.N=1C2=CC=CC=C2SC=1N(C)C(CC1)CCN1C(CC=C)C1=CC=CC=C1 VZWWWGRCXYOHIG-BTJKTKAUSA-N 0.000 description 1
- KBNPOIOGQWESJX-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-ethyl-n-piperidin-4-yl-1,3-benzothiazol-2-amine Chemical compound OC(=O)\C=C/C(O)=O.N=1C2=CC=CC=C2SC=1N(CC)C1CCNCC1 KBNPOIOGQWESJX-BTJKTKAUSA-N 0.000 description 1
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- QEBSDQBQKRVQHJ-UHFFFAOYSA-N 1-(3-bromopropoxy)-4-methylbenzene Chemical compound CC1=CC=C(OCCCBr)C=C1 QEBSDQBQKRVQHJ-UHFFFAOYSA-N 0.000 description 1
- MKAZHYLXIGBNFL-UHFFFAOYSA-N 1-(3-chloropropylsulfonyl)-4-fluorobenzene Chemical compound FC1=CC=C(S(=O)(=O)CCCCl)C=C1 MKAZHYLXIGBNFL-UHFFFAOYSA-N 0.000 description 1
- XXFGBWPWQZWQAU-UHFFFAOYSA-N 1-(6-bromohexoxy)-3-fluorobenzene Chemical compound FC1=CC=CC(OCCCCCCBr)=C1 XXFGBWPWQZWQAU-UHFFFAOYSA-N 0.000 description 1
- QHZKQLXDXBDDHB-UHFFFAOYSA-N 1-bromobut-3-enylbenzene Chemical compound C=CCC(Br)C1=CC=CC=C1 QHZKQLXDXBDDHB-UHFFFAOYSA-N 0.000 description 1
- KPXDMUAKBMCZKP-UHFFFAOYSA-N 1-chloro-3-(4-chlorobutoxy)benzene Chemical compound ClCCCCOC1=CC=CC(Cl)=C1 KPXDMUAKBMCZKP-UHFFFAOYSA-N 0.000 description 1
- HDBACITVPQEAGG-UHFFFAOYSA-N 1-fluoro-3-isothiocyanatobenzene Chemical compound FC1=CC=CC(N=C=S)=C1 HDBACITVPQEAGG-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940044613 1-propanol Drugs 0.000 description 1
- SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 description 1
- VGNRIKSOWPMTKG-UHFFFAOYSA-N 2-(2,5-dimethylphenoxy)propan-1-ol Chemical compound OCC(C)OC1=CC(C)=CC=C1C VGNRIKSOWPMTKG-UHFFFAOYSA-N 0.000 description 1
- MJJBTCMCULRVQR-UHFFFAOYSA-N 2-(2,5-dimethylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC(C)=CC=C1C MJJBTCMCULRVQR-UHFFFAOYSA-N 0.000 description 1
- LKOFUZPVRNUWAA-UHFFFAOYSA-N 2-(2,6-dichlorophenoxy)propan-1-ol Chemical compound OCC(C)OC1=C(Cl)C=CC=C1Cl LKOFUZPVRNUWAA-UHFFFAOYSA-N 0.000 description 1
- BLQRVFGSRGFRCD-UHFFFAOYSA-N 2-(2,6-dimethylphenoxy)propan-1-ol Chemical compound OCC(C)OC1=C(C)C=CC=C1C BLQRVFGSRGFRCD-UHFFFAOYSA-N 0.000 description 1
- DUAIISPCCJPFDG-UHFFFAOYSA-N 2-(2-methylpiperidin-1-yl)ethanol Chemical compound CC1CCCCN1CCO DUAIISPCCJPFDG-UHFFFAOYSA-N 0.000 description 1
- ZWNAEFZELHPLLH-UHFFFAOYSA-N 2-(3,5-dimethylphenoxy)propan-1-ol Chemical compound OCC(C)OC1=CC(C)=CC(C)=C1 ZWNAEFZELHPLLH-UHFFFAOYSA-N 0.000 description 1
- GUCYUBUHYYOCKC-UHFFFAOYSA-N 2-(3-methylphenoxy)propan-1-ol Chemical compound OCC(C)OC1=CC=CC(C)=C1 GUCYUBUHYYOCKC-UHFFFAOYSA-N 0.000 description 1
- ORTPEEDBOZIXNC-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethyl methanesulfonate Chemical compound COC1=CC=C(CCOS(C)(=O)=O)C=C1 ORTPEEDBOZIXNC-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- VHWHISLSSKROOL-UHFFFAOYSA-N 2-[(2,6-dimethylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC(C)=C1OCC1OC1 VHWHISLSSKROOL-UHFFFAOYSA-N 0.000 description 1
- VRFJLUHAQPBTLE-UHFFFAOYSA-N 2-aminopiperidine-1-carboxylic acid Chemical compound NC1CCCCN1C(O)=O VRFJLUHAQPBTLE-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- MEQBJJUWDCYIAB-UHFFFAOYSA-N 2-chloropyridin-3-amine Chemical compound NC1=CC=CN=C1Cl MEQBJJUWDCYIAB-UHFFFAOYSA-N 0.000 description 1
- ZDWGQFVSHPFXAH-UHFFFAOYSA-N 2-ethenyl-3,4-dihydro-2h-chromene Chemical compound C1=CC=C2OC(C=C)CCC2=C1 ZDWGQFVSHPFXAH-UHFFFAOYSA-N 0.000 description 1
- VIBAHERIPJTOAK-UHFFFAOYSA-N 2-methylsulfonyl-[1,3]thiazolo[4,5-c]pyridine Chemical compound N1=CC=C2SC(S(=O)(=O)C)=NC2=C1 VIBAHERIPJTOAK-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- BWCRDMRLKBPUTD-UHFFFAOYSA-N 2-phenylmethoxypropan-1-ol Chemical compound OCC(C)OCC1=CC=CC=C1 BWCRDMRLKBPUTD-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- LDWQUOIUYGBUPN-UHFFFAOYSA-N 3-(oxiran-2-yl)-2,3-dihydro-1,4-benzodioxine Chemical compound C1OC1C1OC2=CC=CC=C2OC1 LDWQUOIUYGBUPN-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- SJTBRFHBXDZMPS-UHFFFAOYSA-N 3-fluorophenol Chemical compound OC1=CC=CC(F)=C1 SJTBRFHBXDZMPS-UHFFFAOYSA-N 0.000 description 1
- ITBKHVAELWAJTJ-UHFFFAOYSA-N 3-methyl-n-piperidin-4-yl-1,3-benzothiazol-2-imine;hydrobromide Chemical compound Br.CN1C2=CC=CC=C2SC1=NC1CCNCC1 ITBKHVAELWAJTJ-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- XGAFCCUNHIMIRV-UHFFFAOYSA-N 4-chloropyridine;hydron;chloride Chemical compound Cl.ClC1=CC=NC=C1 XGAFCCUNHIMIRV-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 101710179734 6,7-dimethyl-8-ribityllumazine synthase 2 Proteins 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- SBEOHZBRWJATAY-UHFFFAOYSA-N CN(C1CCNCC1)[S+]1C2=CC=CC=C2N=C1 Chemical compound CN(C1CCNCC1)[S+]1C2=CC=CC=C2N=C1 SBEOHZBRWJATAY-UHFFFAOYSA-N 0.000 description 1
- 101100327819 Caenorhabditis elegans chl-1 gene Proteins 0.000 description 1
- 101100168093 Caenorhabditis elegans cogc-2 gene Proteins 0.000 description 1
- 101100011365 Caenorhabditis elegans egl-13 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- GCLPVNQFWPYURD-UHFFFAOYSA-N Cl.Cl.C1CN(CCCC)CCC1N=C1N(C)C2=CC=CN=C2S1 Chemical compound Cl.Cl.C1CN(CCCC)CCC1N=C1N(C)C2=CC=CN=C2S1 GCLPVNQFWPYURD-UHFFFAOYSA-N 0.000 description 1
- 206010053398 Clonic convulsion Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 101710186609 Lipoyl synthase 2 Proteins 0.000 description 1
- 101710122908 Lipoyl synthase 2, chloroplastic Proteins 0.000 description 1
- 101710101072 Lipoyl synthase 2, mitochondrial Proteins 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- ZQOOURZBJDJDCI-UHFFFAOYSA-N N=1C2=CC=CC=C2SC=1N(C)C(C1)CCN1CC=CC1=CC=CC=C1 Chemical compound N=1C2=CC=CC=C2SC=1N(C)C(C1)CCN1CC=CC1=CC=CC=C1 ZQOOURZBJDJDCI-UHFFFAOYSA-N 0.000 description 1
- 101150104466 NOCT gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 235000002357 Ribes grossularia Nutrition 0.000 description 1
- 244000171263 Ribes grossularia Species 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 241000009298 Trigla lyra Species 0.000 description 1
- YGNUPHMVMXPKGU-ZCFIWIBFSA-N [(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl methanesulfonate Chemical compound CC1(C)OC[C@H](COS(C)(=O)=O)O1 YGNUPHMVMXPKGU-ZCFIWIBFSA-N 0.000 description 1
- IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 1
- OSHXRTVCVNSLPD-UHFFFAOYSA-N [1,3]thiazolo[4,5-c]pyridin-2-amine Chemical compound N1=CC=C2SC(N)=NC2=C1 OSHXRTVCVNSLPD-UHFFFAOYSA-N 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WJMOWGFGRONZPA-UHFFFAOYSA-N aziridin-1-yl-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC1 WJMOWGFGRONZPA-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
- AWISGSJZNFRYNE-UHFFFAOYSA-N ethanol;dihydrochloride Chemical compound Cl.Cl.CCO AWISGSJZNFRYNE-UHFFFAOYSA-N 0.000 description 1
- YAVSLZYBYXBAAK-UHFFFAOYSA-N ethanol;piperidine Chemical compound CCO.C1CCNCC1 YAVSLZYBYXBAAK-UHFFFAOYSA-N 0.000 description 1
- ZUVJYEIWTWWKPW-UHFFFAOYSA-N ethyl 3-(1,3-benzoxazol-2-ylmethylamino)pyrrolidine-1-carboxylate;dihydrochloride Chemical compound Cl.Cl.C1N(C(=O)OCC)CCC1NCC1=NC2=CC=CC=C2O1 ZUVJYEIWTWWKPW-UHFFFAOYSA-N 0.000 description 1
- QXRDJELOTXBVSV-UHFFFAOYSA-N ethyl 3-(methylamino)pyrrolidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(NC)C1 QXRDJELOTXBVSV-UHFFFAOYSA-N 0.000 description 1
- AYRKWHRVFHIRPI-UHFFFAOYSA-N ethyl 3-aminopyrrolidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(N)C1 AYRKWHRVFHIRPI-UHFFFAOYSA-N 0.000 description 1
- IVCBAYRIQVTSSJ-UHFFFAOYSA-N ethyl 3-isothiocyanatopyrrolidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(N=C=S)C1 IVCBAYRIQVTSSJ-UHFFFAOYSA-N 0.000 description 1
- XMPLCYHFQKQTIF-UHFFFAOYSA-N ethyl 4-(1,3-benzoxazol-2-ylamino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC2=CC=CC=C2O1 XMPLCYHFQKQTIF-UHFFFAOYSA-N 0.000 description 1
- STWAVTDLVKVADZ-UHFFFAOYSA-N ethyl 4-([1,3]oxazolo[4,5-b]pyridin-2-ylamino)piperidine-1-carboxylate;hydrobromide Chemical compound Br.C1CN(C(=O)OCC)CCC1NC1=NC2=NC=CC=C2O1 STWAVTDLVKVADZ-UHFFFAOYSA-N 0.000 description 1
- DTUBADABRUMHQL-UHFFFAOYSA-N ethyl 4-([1,3]thiazolo[4,5-c]pyridin-2-ylamino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC2=CN=CC=C2S1 DTUBADABRUMHQL-UHFFFAOYSA-N 0.000 description 1
- QKPLFXBOWHKIQH-UHFFFAOYSA-N ethyl 4-(methylamino)piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(NC)CC1 QKPLFXBOWHKIQH-UHFFFAOYSA-N 0.000 description 1
- YQTFNXBVTDBPHT-UHFFFAOYSA-N ethyl 4-(propan-2-ylamino)piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(NC(C)C)CC1 YQTFNXBVTDBPHT-UHFFFAOYSA-N 0.000 description 1
- OGSBRHXJCXCALZ-UHFFFAOYSA-N ethyl 4-[(2-hydroxyphenyl)carbamothioylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC(=S)NC1=CC=CC=C1O OGSBRHXJCXCALZ-UHFFFAOYSA-N 0.000 description 1
- DCKPBSOFKUIEDI-UHFFFAOYSA-N ethyl 4-[(5-bromo-6-methoxy-1,3-benzothiazol-2-yl)methylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NCC1=NC2=CC(Br)=C(OC)C=C2S1 DCKPBSOFKUIEDI-UHFFFAOYSA-N 0.000 description 1
- XWJNHXTVAVOWPG-UHFFFAOYSA-N ethyl 4-[(7-chloro-1,3-benzothiazol-2-yl)methylamino]piperidine-1-carboxylate;hydrobromide Chemical compound Br.C1CN(C(=O)OCC)CCC1NCC1=NC2=CC=CC(Cl)=C2S1 XWJNHXTVAVOWPG-UHFFFAOYSA-N 0.000 description 1
- HGANJBXJEJYOIN-UHFFFAOYSA-N ethyl 4-[2-(1,3-benzothiazol-2-yl)ethylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NCCC1=NC2=CC=CC=C2S1 HGANJBXJEJYOIN-UHFFFAOYSA-N 0.000 description 1
- VZRASHIWSJNQHU-UHFFFAOYSA-N ethyl 4-[ethyl(phenylcarbamothioyl)amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N(CC)C(=S)NC1=CC=CC=C1 VZRASHIWSJNQHU-UHFFFAOYSA-N 0.000 description 1
- GQQQULCEHJQUJT-UHFFFAOYSA-N ethyl 4-aminopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(N)CC1 GQQQULCEHJQUJT-UHFFFAOYSA-N 0.000 description 1
- LUBGFMZTGFXIIN-UHFFFAOYSA-N ethyl 4-oxopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(=O)CC1 LUBGFMZTGFXIIN-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- PGIMLPSFEGBJOD-UHFFFAOYSA-N n-(8-azabicyclo[3.2.1]octan-3-yl)-n-methyl-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(N(C3CC4CCC(N4)C3)C)=NC2=C1 PGIMLPSFEGBJOD-UHFFFAOYSA-N 0.000 description 1
- TVGQDMPSAFYBJO-UHFFFAOYSA-N n-[1-[2-(4-methoxyphenyl)ethyl]piperidin-4-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2SC3=NC=CC=C3N=2)CC1 TVGQDMPSAFYBJO-UHFFFAOYSA-N 0.000 description 1
- ROIFBYKXNRPUJQ-UHFFFAOYSA-N n-benzyl-n-piperidin-4-yl-1,3-benzothiazol-2-amine Chemical compound C=1C=CC=CC=1CN(C=1SC2=CC=CC=C2N=1)C1CCNCC1 ROIFBYKXNRPUJQ-UHFFFAOYSA-N 0.000 description 1
- PFBZXLGUUGDBNI-UHFFFAOYSA-N n-methyl-n-[1-(4-phenoxybutyl)pyrrol-3-yl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1N(C)C(=C1)C=CN1CCCCOC1=CC=CC=C1 PFBZXLGUUGDBNI-UHFFFAOYSA-N 0.000 description 1
- UVQMNJYZIVCBNI-UHFFFAOYSA-N n-methyl-n-[8-(4-phenoxybutyl)-8-azabicyclo[3.2.1]octan-3-yl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1N(C)C(C1)CC2CCC1N2CCCCOC1=CC=CC=C1 UVQMNJYZIVCBNI-UHFFFAOYSA-N 0.000 description 1
- OGBYVEMGSUALDH-UHFFFAOYSA-N n-methyl-n-[8-[3-(3-methylphenoxy)propyl]-8-azabicyclo[3.2.1]octan-3-yl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1N(C)C(C1)CC2CCC1N2CCCOC1=CC=CC(C)=C1 OGBYVEMGSUALDH-UHFFFAOYSA-N 0.000 description 1
- JJWSOMYWAXKFRO-UHFFFAOYSA-N n-methyl-n-piperidin-4-yl-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1N(C)C1CCNCC1 JJWSOMYWAXKFRO-UHFFFAOYSA-N 0.000 description 1
- WVLDRWCTUPHXGC-UHFFFAOYSA-N n-methyl-n-piperidin-4-yl-1,3-benzothiazol-2-amine;hydrate;dihydrobromide Chemical compound O.Br.Br.N=1C2=CC=CC=C2SC=1N(C)C1CCNCC1 WVLDRWCTUPHXGC-UHFFFAOYSA-N 0.000 description 1
- DGOAMKVPHKTVDL-UHFFFAOYSA-N n-methyl-n-pyrrolidin-3-yl-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1N(C)C1CCNC1 DGOAMKVPHKTVDL-UHFFFAOYSA-N 0.000 description 1
- WUUOUFAOQYLHQK-UHFFFAOYSA-N n-piperidin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1CNCCC1NC1=NC2=CC=CC=C2S1 WUUOUFAOQYLHQK-UHFFFAOYSA-N 0.000 description 1
- YEYNLOBXANCYSY-UHFFFAOYSA-N n-piperidin-4-yl-1,3-benzothiazol-2-amine;dihydrobromide Chemical compound Br.Br.C1CNCCC1NC1=NC2=CC=CC=C2S1 YEYNLOBXANCYSY-UHFFFAOYSA-N 0.000 description 1
- YWTKTZXFVDBOJX-UHFFFAOYSA-N n-piperidin-4-yl-n-propan-2-yl-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1N(C(C)C)C1CCNCC1 YWTKTZXFVDBOJX-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229940098462 oral drops Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 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
- 238000010998 test method Methods 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Toxicology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Paints Or Removers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67741284A | 1984-12-03 | 1984-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26458A true PH26458A (en) | 1992-07-27 |
Family
ID=24718604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH33124A PH26458A (en) | 1984-12-03 | 1985-12-03 | Benzoxazol and benzothiazolamine derivatives useful as anti-anoxic agents |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0184257B1 (xx) |
| JP (1) | JPH0759578B2 (xx) |
| KR (1) | KR870001512B1 (xx) |
| CN (1) | CN1014790B (xx) |
| AT (1) | ATE54916T1 (xx) |
| AU (1) | AU582601B2 (xx) |
| BG (1) | BG60431B2 (xx) |
| CA (1) | CA1260474A (xx) |
| CY (1) | CY1690A (xx) |
| DE (1) | DE3578885D1 (xx) |
| DK (1) | DK165370C (xx) |
| DZ (1) | DZ863A1 (xx) |
| ES (1) | ES8606306A1 (xx) |
| FI (1) | FI82046C (xx) |
| GR (1) | GR852830B (xx) |
| HK (1) | HK49593A (xx) |
| HU (1) | HU196068B (xx) |
| IE (1) | IE58807B1 (xx) |
| IL (1) | IL77197A (xx) |
| MA (1) | MA20582A1 (xx) |
| NO (1) | NO160076C (xx) |
| NZ (1) | NZ214320A (xx) |
| PH (1) | PH26458A (xx) |
| PT (1) | PT81586B (xx) |
| SU (1) | SU1428203A3 (xx) |
| ZA (1) | ZA859224B (xx) |
| ZW (1) | ZW21685A1 (xx) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8333514D0 (en) * | 1983-12-16 | 1984-01-25 | Erba Farmitalia | Tetrahydrothiazolo(5 4-c)pyridine derivatives |
| KR930005004B1 (ko) * | 1985-04-15 | 1993-06-11 | 쟈안센 파아마슈우티카 엔. 부이. | 치환된 n-[(4-피페리디닐)알킬]이환 축합 옥사졸아민 및 티아졸아민의 제조방법 |
| GB2225574B (en) * | 1987-12-24 | 1991-04-24 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| AU611976B2 (en) * | 1987-12-24 | 1991-06-27 | John Wyeth & Brother Limited | Aroyl urea and carbamic acid derivatives of azabicyclo compounds |
| JPH0393762A (ja) * | 1989-09-04 | 1991-04-18 | Wako Pure Chem Ind Ltd | ４‐ハロゲノ‐２‐アルコキシイミノ‐３‐オキソ脂肪酸の製造方法 |
| MX9100517A (es) * | 1990-08-06 | 1992-04-01 | Smith Kline French Lab | Compuestos |
| ZW1992A1 (en) * | 1991-02-25 | 1993-09-22 | Janssen Pharmaceutica Nv | 4-/(2-benzotiazolyl)methylamino/-b-/(3,4-difluorephenoxy)methyl/-1-piperidine ethanol |
| TW282469B (xx) * | 1993-06-11 | 1996-08-01 | Janssen Pharmaceutica Nv | |
| GB9318431D0 (en) * | 1993-09-06 | 1993-10-20 | Boots Co Plc | Therapeutic agents |
| FR2725989B1 (fr) * | 1994-10-20 | 1997-01-10 | Pf Medicament | Nouvelles 2-(1-(omega-phenoxyalcoylpiperidin-4-yl) aminomethylene)-2h-benzofuran-3-ones substituees, leur preparation et leur application en therapeutique |
| US5744484A (en) * | 1994-11-24 | 1998-04-28 | Janssen Pharmaceutica, N.V. | Lubeluzole intravenous solutions |
| FR2737207B1 (fr) * | 1995-07-26 | 1997-10-17 | Pf Medicament | Nouvelles n-heterocyclyl-1-aryloxyalcoyl-4-piperidinamines substituees, leur preparation et leur application en therapeutique |
| CN1200122A (zh) * | 1995-10-25 | 1998-11-25 | 詹森药业有限公司 | 鲁贝洛唑n－氧化物 |
| US6211199B1 (en) | 1995-11-17 | 2001-04-03 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases |
| US6423704B2 (en) | 1995-12-20 | 2002-07-23 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic diseases |
| US6194406B1 (en) | 1995-12-20 | 2001-02-27 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease |
| US5922737A (en) * | 1996-02-21 | 1999-07-13 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-Benzimidazol-2-YL-amino) piperidin-1-YL)-2-(arlyl) butyl) benzamides useful for the treatment of allergic diseases |
| US5932571A (en) * | 1996-02-21 | 1999-08-03 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-benzimidazol-2-yl) {1,4}diazepan-1-yl)-2-(aryl) butyl) benzamides useful for the treatment of allergic diseases |
| US5998439A (en) | 1996-02-21 | 1999-12-07 | Hoescht Marion Roussel, Inc. | Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases |
| FR2753970B1 (fr) * | 1996-10-01 | 1998-10-30 | Synthelabo | Derives de n-(benzothiazol-2-yl) piperidine-1-ethanamine, leur preparation et leur application en therapeutique |
| GB0315203D0 (en) * | 2003-06-28 | 2003-08-06 | Celltech R&D Ltd | Chemical compounds |
| JP5065908B2 (ja) * | 2004-12-24 | 2012-11-07 | プロシディオン・リミテッド | Ｇタンパク質結合受容体作動薬 |
| KR100925307B1 (ko) * | 2005-03-09 | 2009-11-04 | 에프. 호프만-라 로슈 아게 | 항당뇨성 화합물로서 벤조티아졸, 티아졸로피리딘,벤조옥사졸 및 옥사졸로피리딘 유도체 |
| ES2359431T3 (es) * | 2005-09-02 | 2011-05-23 | F. Hoffmann-La Roche Ag | Derivados de benzooxazol, oxazolopiridina, benzotiazol y tiazolopiridina. |
| RU2470927C2 (ru) | 2007-04-27 | 2012-12-27 | Дайити Санкио Компани,Лимитед | Производные с азотсодержащим шестичленным ароматическим кольцом и содержащие их фармацевтические продукты |
| FR3001151B1 (fr) | 2013-01-21 | 2016-04-08 | Pf Medicament | Association d'un bloqueur de courant sodique lent et d'un inhibiteur du courant if sinusal et les compositions pharmarceutiques la contenant |
| CN107573301B (zh) * | 2017-11-08 | 2020-08-11 | 江苏长青农化股份有限公司 | 一种三环唑中间体的制备方法 |
| CN114349745B (zh) * | 2022-01-14 | 2023-12-08 | 黑龙江中医药大学 | 一种用于治疗心肌缺血的药物及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE831249C (de) * | 1948-02-09 | 1952-02-11 | Ciba A G | Verfahren zur Herstellung heterocyclisch substituierter Diaminochinazoline |
| GB1234058A (xx) * | 1968-10-21 | 1971-06-03 | ||
| DE2545645C2 (de) * | 1975-10-11 | 1983-04-14 | Bayer Ag, 5090 Leverkusen | Thiazolinylamino-piperidin-Derivate |
| US4634704A (en) * | 1983-10-06 | 1987-01-06 | Janssen Pharmaceutica, N.V. | Anti-allergic five membered heterocyclic ring containing N-(bicyclic heterocycyl)-4-piperidinamines |
| DE3484096D1 (de) * | 1983-11-30 | 1991-03-14 | Janssen Pharmaceutica Nv | Bizyklisches heterozyklyl aufveisende n-(bizyklisches heterozyklyl-4-piperidinamine. |
| PH23995A (en) * | 1984-01-09 | 1990-02-09 | Janssen Pharmaceutica Nv | 4((bicycle heterocyclyl)-methyl and hetero)piperidines |
-
1985
- 1985-10-30 CA CA000494185A patent/CA1260474A/en not_active Expired
- 1985-11-01 KR KR1019850008142A patent/KR870001512B1/ko not_active IP Right Cessation
- 1985-11-12 SU SU853982357A patent/SU1428203A3/ru active
- 1985-11-22 EP EP85201937A patent/EP0184257B1/en not_active Expired - Lifetime
- 1985-11-22 DE DE8585201937T patent/DE3578885D1/de not_active Expired - Fee Related
- 1985-11-22 AT AT85201937T patent/ATE54916T1/de not_active IP Right Cessation
- 1985-11-25 NZ NZ214320A patent/NZ214320A/en unknown
- 1985-11-25 GR GR852830A patent/GR852830B/el unknown
- 1985-12-01 DZ DZ850258A patent/DZ863A1/fr active
- 1985-12-02 HU HU854596A patent/HU196068B/hu not_active IP Right Cessation
- 1985-12-02 CN CN85108556A patent/CN1014790B/zh not_active Expired
- 1985-12-02 FI FI854768A patent/FI82046C/fi not_active IP Right Cessation
- 1985-12-02 MA MA20807A patent/MA20582A1/fr unknown
- 1985-12-02 DK DK558185A patent/DK165370C/da not_active IP Right Cessation
- 1985-12-02 ZW ZW216/85A patent/ZW21685A1/xx unknown
- 1985-12-02 IE IE302385A patent/IE58807B1/en not_active IP Right Cessation
- 1985-12-02 AU AU50574/85A patent/AU582601B2/en not_active Ceased
- 1985-12-02 PT PT81586A patent/PT81586B/pt not_active IP Right Cessation
- 1985-12-02 ZA ZA859224A patent/ZA859224B/xx unknown
- 1985-12-02 NO NO854837A patent/NO160076C/no unknown
- 1985-12-02 IL IL77197A patent/IL77197A/xx not_active IP Right Cessation
- 1985-12-03 JP JP60270848A patent/JPH0759578B2/ja not_active Expired - Fee Related
- 1985-12-03 PH PH33124A patent/PH26458A/en unknown
- 1985-12-03 ES ES549542A patent/ES8606306A1/es not_active Expired
-
1993
- 1993-05-20 HK HK495/93A patent/HK49593A/xx not_active IP Right Cessation
- 1993-06-16 BG BG97875A patent/BG60431B2/bg unknown
-
1994
- 1994-01-14 CY CY169094A patent/CY1690A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PH26458A (en) | Benzoxazol and benzothiazolamine derivatives useful as anti-anoxic agents | |
| EP0196132B1 (en) | 1,2-benzisoxazol-3-yl and 1,2-benzisothiazol-3-yl derivatives | |
| US4634704A (en) | Anti-allergic five membered heterocyclic ring containing N-(bicyclic heterocycyl)-4-piperidinamines | |
| US4835161A (en) | Anti-histaminic compositions containing n-heterocyclyl-4-piperidinamines | |
| EP0199400B1 (en) | Substituted N-[(4-piperidinyl)alkyl] bicyclic condensed ozazol- and thiazolamines | |
| CA2040086C (en) | Novel 2,9-disubstituted-4h-pyrido[1,2-a]pyrimidin-4-ones | |
| KR0145706B1 (ko) | 항정신병성 3-피페라지닐벤즈아졸 유도체 | |
| US4861785A (en) | Benzoxazol-and benzothiazolamine derivatives, useful as anti-anoxic agents | |
| US4689330A (en) | Antidepressive substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines | |
| US5010198A (en) | Intermediates for the synthesis of benzoxazol- and benzothiazolamine derivatives, useful as anti-anoxic agents | |
| CZ580390A3 (en) | 6-ARYL-5,6-DIHYDRO-IMIDAZO£2,1-b|THIAZOLE DERIVATIVES, PROCESS OF THEIR PREPARATION, INTERMEDIATES FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITION CONTAINING THEREOF | |
| US5728717A (en) | Pyridiniminyl-1,2-benzisothiazoles | |
| US4826848A (en) | Antidepressive substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines | |
| US4749702A (en) | Antidepressive substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines | |
| AU6334299A (en) | Tricyclic delta3-piperidines as pharmaceuticals | |
| KR870001511B1 (ko) | 벤조옥사졸-및 벤조티아졸아민 유도체의 제조방법 | |
| KR870001647B1 (ko) | 5원 헤테로사이클 고리를 갖는 n-(비사이클 헤테로 사이클 )-4-피페리딘아민의 제조방법 | |
| EP0699675A2 (en) | 3-(4-(1-Substituted-4-piperazinyl)butyl)-4-thiazolidinone and related compounds | |
| IE842551L (en) | Five membered heterocyclic ring containing n-(bicyclic¹heterocyclyl) -4-piperidinamines. | |
| IL105594A (en) | History of 3-piperazinylbenzperazole |