SK53495A3 - 4-quinolinyl derivatives, method of their production, pharmaceutical agents on their base, method of their production and use - Google Patents

4-quinolinyl derivatives, method of their production, pharmaceutical agents on their base, method of their production and use Download PDF

Info

Publication number: SK53495A3
Authority: SK; Slovakia
Prior art keywords: formula; compounds; acid; mixture; group
Prior art date: 1992-10-27

Application number

SK534-95A

Other languages

English (en)

Slovak (sk)

Inventor

Marc G Venet

Jerome E G Guillemont

Daniel F J Vernier

Franck C Odds

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.)

1992-10-27

Filing date

1993-10-19

Publication date

1995-09-13

1993-10-19 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1995-09-13 Publication of SK53495A3 publication Critical patent/SK53495A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 25
238000004519 manufacturing process Methods 0.000 title claims description 12
SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical class [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 title 1
239000008177 pharmaceutical agent Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 102
-1 trifluromethyl Chemical group 0.000 claims abstract description 37
239000002253 acid Substances 0.000 claims abstract description 33
150000003839 salts Chemical class 0.000 claims abstract description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 19
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 21
239000004480 active ingredient Substances 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
239000003153 chemical reaction reagent Substances 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
150000001204 N-oxides Chemical class 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
239000002585 base Substances 0.000 claims description 7
125000004663 dialkyl amino group Chemical group 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 6
BBRATVCTCKUNNY-UHFFFAOYSA-N 4-[(3-chlorophenyl)-(1,2,4-triazol-1-yl)methyl]quinoline Chemical compound ClC1=CC=CC(C(C=2C3=CC=CC=C3N=CC=2)N2N=CN=C2)=C1 BBRATVCTCKUNNY-UHFFFAOYSA-N 0.000 claims description 4
150000001622 bismuth compounds Chemical class 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000000524 functional group Chemical group 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
229940126409 proton pump inhibitor Drugs 0.000 claims description 3
239000000612 proton pump inhibitor Substances 0.000 claims description 3
230000009466 transformation Effects 0.000 claims description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 108
230000000694 effects Effects 0.000 abstract description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
208000035475 disorder Diseases 0.000 abstract description 3
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 abstract description 3
125000001424 substituent group Chemical group 0.000 abstract description 3
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 abstract description 2
206010019375 Helicobacter infections Diseases 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
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125000001309 chloro group Chemical group Cl* 0.000 description 69
239000000543 intermediate Substances 0.000 description 58
239000000243 solution Substances 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000012044 organic layer Substances 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
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239000000741 silica gel Substances 0.000 description 11
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
150000003254 radicals Chemical class 0.000 description 10
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000000908 ammonium hydroxide Substances 0.000 description 9
238000004440 column chromatography Methods 0.000 description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 8
239000003826 tablet Substances 0.000 description 8
229920000858 Cyclodextrin Polymers 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000003480 eluent Substances 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
239000000047 product Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
241000590002 Helicobacter pylori Species 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
125000001246 bromo group Chemical group Br* 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
229940037467 helicobacter pylori Drugs 0.000 description 5
239000010410 layer Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
150000003248 quinolines Chemical class 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
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 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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150000001450 anions Chemical class 0.000 description 4
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
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125000004433 nitrogen atom Chemical group N* 0.000 description 4
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
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239000001116 FEMA 4028 Substances 0.000 description 3
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238000007126 N-alkylation reaction Methods 0.000 description 3
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239000012298 atmosphere Substances 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
229960004853 betadex Drugs 0.000 description 3
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
150000001728 carbonyl compounds Chemical class 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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239000011737 fluorine Substances 0.000 description 3
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238000000338 in vitro Methods 0.000 description 3
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239000002609 medium Substances 0.000 description 3
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239000007858 starting material Substances 0.000 description 3
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FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 2
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XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 2
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
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MUDSDYNRBDKLGK-UHFFFAOYSA-N 4-methylquinoline Chemical class C1=CC=C2C(C)=CC=NC2=C1 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 description 2
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
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239000002841 Lewis acid Substances 0.000 description 2
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238000002835 absorbance Methods 0.000 description 1
XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 1
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238000005804 alkylation reaction Methods 0.000 description 1
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235000010233 benzoic acid Nutrition 0.000 description 1
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239000011230 binding agent Substances 0.000 description 1
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230000015572 biosynthetic process Effects 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
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238000009835 boiling Methods 0.000 description 1
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
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244000240602 cacao Species 0.000 description 1
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239000007795 chemical reaction product Substances 0.000 description 1
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238000007865 diluting Methods 0.000 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
DBYQHFPBWKKZAT-UHFFFAOYSA-N lithium;benzene Chemical compound [Li+].C1=CC=[C-]C=C1 DBYQHFPBWKKZAT-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
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239000002075 main ingredient Substances 0.000 description 1
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CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 1
ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 description 1
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239000001923 methylcellulose Substances 0.000 description 1
VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
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DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
GCRJSVFPQGRJAD-UHFFFAOYSA-N n-[(3-chlorophenyl)-quinolin-4-ylmethyl]formamide Chemical compound ClC1=CC=CC(C(NC=O)C=2C3=CC=CC=C3N=CC=2)=C1 GCRJSVFPQGRJAD-UHFFFAOYSA-N 0.000 description 1
YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 description 1
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239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 1
229960000381 omeprazole Drugs 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002891 organic anions Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
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150000004965 peroxy acids Chemical class 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000008213 purified water Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical class C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
150000004508 retinoic acid derivatives Chemical class 0.000 description 1
229940085605 saccharin sodium Drugs 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000009097 single-agent therapy Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
201000011549 stomach cancer Diseases 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960005137 succinic acid Drugs 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000004114 suspension culture Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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238000010998 test method Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Medicinal Preparation (AREA)
Steroid Compounds (AREA)

SK534-95A 1992-10-27 1993-10-19 4-quinolinyl derivatives, method of their production, pharmaceutical agents on their base, method of their production and use SK53495A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US96700892A	1992-10-27	1992-10-27
US6980493A	1993-06-01	1993-06-01
PCT/EP1993/002884 WO1994010164A1 (fr)	1992-10-27	1993-10-19	Derives de la 4-quinoleinyle a activite anti-helicobacter

Publications (1)

Publication Number	Publication Date
SK53495A3 true SK53495A3 (en)	1995-09-13

Family

ID=26750446

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK534-95A SK53495A3 (en)	1992-10-27	1993-10-19	4-quinolinyl derivatives, method of their production, pharmaceutical agents on their base, method of their production and use

Country Status (22)

Country	Link
US (1)	US5589484A (fr)
EP (1)	EP0666855B1 (fr)
JP (1)	JPH08502503A (fr)
KR (1)	KR100239003B1 (fr)
AT (1)	ATE143013T1 (fr)
AU (1)	AU675087B2 (fr)
BG (1)	BG99566A (fr)
CA (1)	CA2146651A1 (fr)
CZ (1)	CZ287159B6 (fr)
DE (1)	DE69304930T2 (fr)
DK (1)	DK0666855T3 (fr)
ES (1)	ES2094567T3 (fr)
FI (1)	FI951996A7 (fr)
GR (1)	GR3021690T3 (fr)
HU (1)	HUT71895A (fr)
LV (1)	LV10951B (fr)
NO (1)	NO951588L (fr)
NZ (1)	NZ256871A (fr)
PL (1)	PL175679B1 (fr)
RU (1)	RU2130933C1 (fr)
SK (1)	SK53495A3 (fr)
WO (1)	WO1994010164A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1999061438A1 (fr) *	1998-05-23	1999-12-02	Byk Gulden Lomberg Chemische Fabrik Gmbh	Derives de quinoleine-aminomethyle-pyridyle a activite anti-helicobacter
GB9819382D0 (en)	1998-09-04	1998-10-28	Cerebrus Ltd	Chemical compounds I
TW200803855A (en) *	2006-02-24	2008-01-16	Kalypsys Inc	Quinolones useful as inducible nitric oxide synthase inhibitors
EP2519508B1 (fr) *	2009-12-31	2014-07-02	Viamet Pharmaceuticals, Inc.	Composés inhibiteurs de métallo-enzyme
AU2013385618B2 (en) *	2013-04-02	2017-01-05	Annji Pharmaceutical Co., Ltd.	Multifunctional quinoline derivatives as anti-neurodegenerative agents
US9302992B2 (en)	2013-04-02	2016-04-05	Annji Pharmaceutical Co., Ltd.	Multifunctional quinoline derivatives as anti-neurodegenerative agents
JP6254239B2 (ja) *	2016-02-29	2017-12-27	大日精化工業株式会社	ポリマーの製造方法
JP6245719B1 (ja)	2017-03-24	2017-12-13	大日精化工業株式会社	ポリマーの製造方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT294090B (de) *	1969-04-22	1971-11-10	Degussa	Verfahren zur Herstellung von neuen Aminopyridinen, von deren optisch aktiven bzw. diastereomeren Formen, deren Salzen und deren quartären Verbindungen
CH679582A5 (fr) *	1988-07-18	1992-03-13	Glaxo Group Ltd
GB8827820D0 (en) *	1988-11-29	1988-12-29	Janssen Pharmaceutica Nv	(1h-azol-1-ylmethyl)substituted quinoline derivatives
CA2002864C (fr) *	1988-11-29	1999-11-16	Eddy J. E. Freyne	Derives de quinoline, quinazoline ou quinoxaline (1h-azol-1-ylmethyl) substitues
GB8827822D0 (en) *	1988-11-29	1988-12-29	Janssen Pharmaceutica Nv	(1h-azol-1-ylmethyl)substituted quinoline derivatives
US5185346A (en) *	1988-11-29	1993-02-09	Hanssen Pharmaceutica	(1H-azol-1-ylmethyl)substituted quinoline derivatives
US5128140A (en) *	1991-01-14	1992-07-07	The Procter & Gamble Company	Swallowable pharmaceutical compositions

1993
- 1993-10-19 ES ES93922961T patent/ES2094567T3/es not_active Expired - Lifetime
- 1993-10-19 NZ NZ256871A patent/NZ256871A/en unknown
- 1993-10-19 DK DK93922961.3T patent/DK0666855T3/da active
- 1993-10-19 PL PL93308550A patent/PL175679B1/pl unknown
- 1993-10-19 CA CA002146651A patent/CA2146651A1/fr not_active Abandoned
- 1993-10-19 HU HU9501207A patent/HUT71895A/hu unknown
- 1993-10-19 DE DE69304930T patent/DE69304930T2/de not_active Expired - Fee Related
- 1993-10-19 SK SK534-95A patent/SK53495A3/sk unknown
- 1993-10-19 AT AT93922961T patent/ATE143013T1/de not_active IP Right Cessation
- 1993-10-19 AU AU51782/93A patent/AU675087B2/en not_active Ceased
- 1993-10-19 WO PCT/EP1993/002884 patent/WO1994010164A1/fr not_active Ceased
- 1993-10-19 JP JP6510636A patent/JPH08502503A/ja active Pending
- 1993-10-19 CZ CZ1995837A patent/CZ287159B6/cs not_active IP Right Cessation
- 1993-10-19 EP EP93922961A patent/EP0666855B1/fr not_active Expired - Lifetime
- 1993-10-19 US US08/428,176 patent/US5589484A/en not_active Expired - Fee Related
- 1993-10-19 KR KR1019950701501A patent/KR100239003B1/ko not_active Expired - Fee Related
- 1993-10-19 RU RU95109440A patent/RU2130933C1/ru active
1995
- 1995-04-12 BG BG99566A patent/BG99566A/xx unknown
- 1995-04-26 NO NO951588A patent/NO951588L/no unknown
- 1995-04-26 FI FI951996A patent/FI951996A7/fi unknown
- 1995-05-26 LV LVP-95-143A patent/LV10951B/en unknown
1996
- 1996-11-18 GR GR960403075T patent/GR3021690T3/el unknown

Also Published As

Publication number	Publication date
HUT71895A (en)	1996-02-28
BG99566A (en)	1996-01-31
DK0666855T3 (da)	1996-10-07
PL175679B1 (pl)	1999-01-29
JPH08502503A (ja)	1996-03-19
DE69304930T2 (de)	1997-02-27
LV10951A (lv)	1995-12-20
NZ256871A (en)	1995-09-26
NO951588L (no)	1995-06-27
GR3021690T3 (en)	1997-02-28
DE69304930D1 (de)	1996-10-24
CZ287159B6 (en)	2000-10-11
PL308550A1 (en)	1995-08-21
LV10951B (en)	1996-08-20
ES2094567T3 (es)	1997-01-16
RU2130933C1 (ru)	1999-05-27
AU675087B2 (en)	1997-01-23
FI951996A0 (fi)	1995-04-26
RU95109440A (ru)	1997-03-10
KR100239003B1 (ko)	2000-02-01
CZ83795A3 (en)	1995-09-13
FI951996A7 (fi)	1995-04-26
KR950704297A (ko)	1995-11-17
CA2146651A1 (fr)	1994-05-11
EP0666855A1 (fr)	1995-08-16
EP0666855B1 (fr)	1996-09-18
US5589484A (en)	1996-12-31
ATE143013T1 (de)	1996-10-15
AU5178293A (en)	1994-05-24
HU9501207D0 (en)	1995-06-28
WO1994010164A1 (fr)	1994-05-11
NO951588D0 (no)	1995-04-26

Publication	Publication Date	Title
RU2152392C1 (ru)	2000-07-10	Ацильные производные азолонов, способ их получения, фармацевтическая композиция на их основе и способ ее получения
US4880806A (en)	1989-11-14	1-Cyclopropyl-6-fluoro-7-piperazinyl-1,4-Dihydro-4-oxo-quinoline-3-carboxylic acid derivatives
US5811426A (en)	1998-09-22	Urea and thiourea derivatives of azolones
AP435A (en)	1995-11-17	Substituted azolone derivatives.
EP1107962A1 (fr)	2001-06-20	Derives de quinolin-2-one utiles en tant qu'agents anticancereux
CZ293296B6 (cs)	2004-03-17	(Imidazol-5-yl)methyl-2-chinolinonové deriváty inhibující farnesyl protein transferázu
NZ289853A (en)	1997-11-24	4(sulphonyl)piperazine azolone derivatives for anti-helicobacter compositions
RU2152940C1 (ru)	2000-07-20	Гетероциклические производные азолонов, действующие против helicobacter, фармацевтическая композиция и способ их получения
SK53495A3 (en)	1995-09-13	4-quinolinyl derivatives, method of their production, pharmaceutical agents on their base, method of their production and use
SK127196A3 (en)	1997-05-07	Ester and carbamane derivatives of azolones, process for preparation and use thereof, a composition containing these compounds and process for preparation of this composition
EP0364943B1 (fr)	1994-06-08	Composés benzohétérocycliques