PH26458A - Benzoxazol and benzothiazolamine derivatives useful as anti-anoxic agents - Google Patents

Benzoxazol and benzothiazolamine derivatives useful as anti-anoxic agents Download PDF

Info

Publication number: PH26458A
Authority: PH; Philippines
Prior art keywords: formula; parts; radical; alkyl; aryl
Prior art date: 1984-12-03

Application number

PH33124A

Other languages

English (en)

Inventor

Raymond A Stokbroekx

Marcel G M Luyckx

Frans Janssens

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-12-03

Filing date

1985-12-03

Publication date

1992-07-27

1985-12-03 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1992-07-27 Publication of PH26458A publication Critical patent/PH26458A/en

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
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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
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RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
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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
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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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Chemical Kinetics & Catalysis (AREA)
Neurology (AREA)
Hospice & Palliative Care (AREA)
Toxicology (AREA)
Psychiatry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Hydrogenated Pyridines (AREA)
Pyrrole Compounds (AREA)
Paints Or Removers (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

PH33124A 1984-12-03 1985-12-03 Benzoxazol and benzothiazolamine derivatives useful as anti-anoxic agents PH26458A (en)

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 (da)
JP (1)	JPH0759578B2 (da)
KR (1)	KR870001512B1 (da)
CN (1)	CN1014790B (da)
AT (1)	ATE54916T1 (da)
AU (1)	AU582601B2 (da)
BG (1)	BG60431B2 (da)
CA (1)	CA1260474A (da)
CY (1)	CY1690A (da)
DE (1)	DE3578885D1 (da)
DK (1)	DK165370C (da)
DZ (1)	DZ863A1 (da)
ES (1)	ES8606306A1 (da)
FI (1)	FI82046C (da)
GR (1)	GR852830B (da)
HK (1)	HK49593A (da)
HU (1)	HU196068B (da)
IE (1)	IE58807B1 (da)
IL (1)	IL77197A (da)
MA (1)	MA20582A1 (da)
NO (1)	NO160076C (da)
NZ (1)	NZ214320A (da)
PH (1)	PH26458A (da)
PT (1)	PT81586B (da)
SU (1)	SU1428203A3 (da)
ZA (1)	ZA859224B (da)
ZW (1)	ZW21685A1 (da)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
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
IE63474B1 (en) *	1987-12-24	1995-04-19	Wyeth John & Brother Ltd	Heterocyclic 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
IE912760A1 (en) *	1990-08-06	1992-02-12	Smith Kline French Lab	Compounds
ZW1992A1 (en) *	1991-02-25	1993-09-22	Janssen Pharmaceutica Nv	4-/(2-benzotiazolyl)methylamino/-b-/(3,4-difluorephenoxy)methyl/-1-piperidine ethanol
TW282469B (da) *	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
MX9703839A (es) *	1994-11-24	1997-08-30	Janssen Pharmaceutica Nv	Soluciones intravenosas de lubeluzol.
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
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
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
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
EP1838706A1 (en) *	2004-12-24	2007-10-03	Prosidion Limited	G-protein coupled receptor agonists
MX2007010573A (es) *	2005-03-09	2007-10-04	Hoffmann La Roche	Derivados de benzotiazol, tiazolopiridina, benzooxazol y oxazolopiridina como compuestos antidiabeticos.
CN101253171B (zh) *	2005-09-02	2011-06-15	霍夫曼-拉罗奇有限公司	苯并噁唑、噁唑并吡啶、苯并噻唑和噻唑并吡啶衍生物
DK2151439T3 (da)	2007-04-27	2014-03-10	Daiichi Sankyo Co Ltd	Nitrogeneret aromatisk 6-leddet ringderivat, og farmaceutisk middel omfattende dette
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
CN117229228B (zh) *	2023-09-15	2025-09-12	中国人民解放军军事科学院防化研究院	一种2-硫代苯并噻唑类化合物的合成方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
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 (da) *	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
EP0144101B1 (en) *	1983-11-30	1991-02-06	Janssen Pharmaceutica N.V.	Bicyclic heterocyclyl containing n-(bicyclic heterocyclyl)-4-piperidinamines
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 Expired
- 1985-11-12 SU SU853982357A patent/SU1428203A3/ru active
- 1985-11-22 DE DE8585201937T patent/DE3578885D1/de not_active Expired - Fee Related
- 1985-11-22 EP EP85201937A patent/EP0184257B1/en not_active Expired - Lifetime
- 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 CN CN85108556A patent/CN1014790B/zh not_active Expired
- 1985-12-02 PT PT81586A patent/PT81586B/pt not_active IP Right Cessation
- 1985-12-02 MA MA20807A patent/MA20582A1/fr unknown
- 1985-12-02 IL IL77197A patent/IL77197A/xx not_active IP Right Cessation
- 1985-12-02 FI FI854768A patent/FI82046C/fi not_active IP Right Cessation
- 1985-12-02 IE IE302385A patent/IE58807B1/en not_active IP Right Cessation
- 1985-12-02 DK DK558185A patent/DK165370C/da not_active IP Right Cessation
- 1985-12-02 ZA ZA859224A patent/ZA859224B/xx unknown
- 1985-12-02 AU AU50574/85A patent/AU582601B2/en not_active Ceased
- 1985-12-02 NO NO854837A patent/NO160076C/no unknown
- 1985-12-02 ZW ZW216/85A patent/ZW21685A1/xx unknown
- 1985-12-02 HU HU854596A patent/HU196068B/hu 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/en not_active IP Right Cessation
- 1993-06-16 BG BG097875A patent/BG60431B2/bg unknown
1994
- 1994-01-14 CY CY169094A patent/CY1690A/xx unknown

Also Published As

Publication number	Publication date
NO160076B (no)	1988-11-28
EP0184257A1 (en)	1986-06-11
IL77197A (en)	1991-07-18
FI82046B (fi)	1990-09-28
SU1428203A3 (ru)	1988-09-30
CN85108556A (zh)	1986-07-30
CY1690A (en)	1994-01-14
JPH0759578B2 (ja)	1995-06-28
ES549542A0 (es)	1986-04-16
KR870001512B1 (ko)	1987-08-20
AU5057485A (en)	1986-07-17
BG60431B2 (bg)	1995-03-31
CN1014790B (zh)	1991-11-20
DK558185D0 (da)	1985-12-02
CA1260474A (en)	1989-09-26
ATE54916T1 (de)	1990-08-15
PT81586A (en)	1986-01-01
IE853023L (en)	1986-06-03
KR860004894A (ko)	1986-07-14
ZA859224B (en)	1987-07-29
HUT40668A (en)	1987-01-28
GR852830B (da)	1986-03-27
ZW21685A1 (en)	1987-06-17
DK165370B (da)	1992-11-16
ES8606306A1 (es)	1986-04-16
NZ214320A (en)	1988-03-30
FI854768A7 (fi)	1986-06-04
DZ863A1 (fr)	2004-09-13
DK165370C (da)	1993-04-05
NO854837L (no)	1986-06-04
AU582601B2 (en)	1989-04-06
DE3578885D1 (de)	1990-08-30
FI82046C (fi)	1991-01-10
MA20582A1 (fr)	1986-07-01
FI854768A0 (fi)	1985-12-02
IE58807B1 (en)	1993-11-17
PT81586B (pt)	1988-01-22
JPS61137884A (ja)	1986-06-25
HK49593A (en)	1993-05-27
EP0184257B1 (en)	1990-07-25
DK558185A (da)	1986-06-04
HU196068B (en)	1988-09-28
NO160076C (no)	1989-03-08

Publication	Publication Date	Title
EP0184257B1 (en)	1990-07-25	Benzoxazol- and benzothiazolamine derivatives
EP0196132B1 (en)	1992-08-12	1,2-benzisoxazol-3-yl and 1,2-benzisothiazol-3-yl derivatives
US4634704A (en)	1987-01-06	Anti-allergic five membered heterocyclic ring containing N-(bicyclic heterocycyl)-4-piperidinamines
EP0199400B1 (en)	1990-09-26	Substituted N-[(4-piperidinyl)alkyl] bicyclic condensed ozazol- and thiazolamines
CA2040086C (en)	2003-12-30	Novel 2,9-disubstituted-4h-pyrido[1,2-a]pyrimidin-4-ones
NZ210776A (en)	1988-03-30	4-((bicycloheterocyclyl)-methyl and -hetero)-piperidine derivatives and pharmaceutical compositions
US4835161A (en)	1989-05-30	Anti-histaminic compositions containing n-heterocyclyl-4-piperidinamines
KR0145706B1 (ko)	1998-08-17	항정신병성 3-피페라지닐벤즈아졸 유도체
US4861785A (en)	1989-08-29	Benzoxazol-and benzothiazolamine derivatives, useful as anti-anoxic agents
US4689330A (en)	1987-08-25	Antidepressive substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines
BG60587B1 (bg)	1995-09-29	Имуностимулиращи 6-арил-5,6-дихидроимидазо(2,1-в)тиазолови производни
US5010198A (en)	1991-04-23	Intermediates for the synthesis of benzoxazol- and benzothiazolamine derivatives, useful as anti-anoxic agents
US5728717A (en)	1998-03-17	Pyridiniminyl-1,2-benzisothiazoles
US4826848A (en)	1989-05-02	Antidepressive substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines
US4749702A (en)	1988-06-07	Antidepressive substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines
KR870001511B1 (ko)	1987-08-20	벤조옥사졸-및 벤조티아졸아민 유도체의 제조방법
KR870001647B1 (ko)	1987-09-18	5원 헤테로사이클 고리를 갖는 n-(비사이클 헤테로 사이클 )-4-피페리딘아민의 제조방법
CA1330081C (en)	1994-06-07	Bicyclic heterocyclyl containing n-(bicyclic heterocyclyl)-4-piperidinamines
EP0699675A2 (en)	1996-03-06	3-(4-(1-Substituted-4-piperazinyl)butyl)-4-thiazolidinone and related compounds
IE842551L (en)	1985-04-06	Five membered heterocyclic ring containing n-(bicyclic¹heterocyclyl) -4-piperidinamines.
HK1038009B (en)	2004-12-24	Tricyclic delta3-piperidines as pharmaceuticals
HK1038009A1 (en)	2002-03-01	Tricyclic delta3-piperidines as pharmaceuticals
IL105594A (en)	1994-10-07	History of 3-piperazinylbenzperazole