LV10092B - Optically active pyridoncarboxylic acid derivatives - Google Patents

Optically active pyridoncarboxylic acid derivatives Download PDF

Info

Publication number: LV10092B
Authority: LV; Latvia
Prior art keywords: cis; amino; compound; group; oxo
Prior art date: 1988-04-27

Application number

LVP-92-696A

Other languages

English (en)

Latvian (lv)

Inventor

Isao Hayakawa

Yoichi Kimura

Original Assignee

Daiichi Seiyaku Co

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.)

1988-04-27

Filing date

1992-12-30

Publication date

1995-02-20

1992-12-30 Application filed by Daiichi Seiyaku Co filed Critical Daiichi Seiyaku Co

1995-02-20 Publication of LV10092B publication Critical patent/LV10092B/en

Links

239000002253 acid Substances 0.000 title description 18
150000001875 compounds Chemical class 0.000 claims abstract description 169
150000003839 salts Chemical class 0.000 claims abstract description 29
YSLIPUSJNFIFAB-UHFFFAOYSA-N 2-oxopyridine-1-carboxylic acid Chemical class OC(=O)N1C=CC=CC1=O YSLIPUSJNFIFAB-UHFFFAOYSA-N 0.000 claims abstract description 20
239000003242 anti bacterial agent Substances 0.000 claims abstract 2
-1 3-aminopyrrolidinyl Chemical group 0.000 claims description 96
125000003277 amino group Chemical group 0.000 claims description 36
125000004122 cyclic group Chemical group 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 11
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
LLSRLLPHUVVLQJ-UHFFFAOYSA-N 1-cycloheptyldiazepane Chemical compound C1CCCCCC1N1NCCCCC1 LLSRLLPHUVVLQJ-UHFFFAOYSA-N 0.000 claims description 3
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical group C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
150000004885 piperazines Chemical class 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
208000015181 infectious disease Diseases 0.000 abstract description 7
230000002458 infectious effect Effects 0.000 abstract description 5
241000894006 Bacteria Species 0.000 abstract description 4
230000000844 anti-bacterial effect Effects 0.000 abstract description 4
238000007911 parenteral administration Methods 0.000 abstract description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 174
230000002829 reductive effect Effects 0.000 description 110
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 98
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 93
229960001701 chloroform Drugs 0.000 description 87
239000002904 solvent Substances 0.000 description 78
239000000203 mixture Substances 0.000 description 77
239000000243 solution Substances 0.000 description 77
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 70
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 68
239000013078 crystal Substances 0.000 description 58
238000002844 melting Methods 0.000 description 55
230000008018 melting Effects 0.000 description 55
238000003756 stirring Methods 0.000 description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
239000011541 reaction mixture Substances 0.000 description 49
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
239000007864 aqueous solution Substances 0.000 description 38
150000001732 carboxylic acid derivatives Chemical group 0.000 description 36
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
235000011167 hydrochloric acid Nutrition 0.000 description 34
229960000443 hydrochloric acid Drugs 0.000 description 34
DTYLXDLAOLOTKT-UHFFFAOYSA-N 1,4-dihydroquinoline-3-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)=CNC2=C1 DTYLXDLAOLOTKT-UHFFFAOYSA-N 0.000 description 33
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
101150041968 CDC13 gene Proteins 0.000 description 29
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 29
238000005160 1H NMR spectroscopy Methods 0.000 description 28
238000004458 analytical method Methods 0.000 description 28
150000002148 esters Chemical class 0.000 description 24
238000001914 filtration Methods 0.000 description 23
229940086542 triethylamine Drugs 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
239000010410 layer Substances 0.000 description 20
239000000284 extract Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
150000007660 quinolones Chemical class 0.000 description 17
238000005481 NMR spectroscopy Methods 0.000 description 16
238000001816 cooling Methods 0.000 description 16
239000003480 eluent Substances 0.000 description 16
VWSDKMQGCVVQBV-NTSWFWBYSA-N tert-butyl n-[(1r,2s)-2-fluorocyclopropyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1C[C@@H]1F VWSDKMQGCVVQBV-NTSWFWBYSA-N 0.000 description 16
238000010992 reflux Methods 0.000 description 15
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
230000000845 anti-microbial effect Effects 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
239000000725 suspension Substances 0.000 description 12
238000001704 evaporation Methods 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
208000033809 Suppuration Diseases 0.000 description 9
239000003814 drug Substances 0.000 description 9
229940079593 drug Drugs 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
201000010099 disease Diseases 0.000 description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
238000010898 silica gel chromatography Methods 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
238000000605 extraction Methods 0.000 description 7
239000012046 mixed solvent Substances 0.000 description 7
230000003389 potentiating effect Effects 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 6
239000012230 colorless oil Substances 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
125000001153 fluoro group Chemical group F* 0.000 description 6
238000000034 method Methods 0.000 description 6
150000002828 nitro derivatives Chemical class 0.000 description 6
125000004433 nitrogen atom Chemical group N* 0.000 description 6
125000004193 piperazinyl group Chemical group 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
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 5
150000008064 anhydrides Chemical class 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
150000003857 carboxamides Chemical class 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
244000005700 microbiome Species 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000012746 preparative thin layer chromatography Methods 0.000 description 5
125000000719 pyrrolidinyl group Chemical group 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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150000001412 amines Chemical class 0.000 description 4
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229910052799 carbon Inorganic materials 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000000746 purification Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
QQWYQAQQADNEIC-RVDMUPIBSA-N tert-butyl [(z)-[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)O\N=C(/C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-RVDMUPIBSA-N 0.000 description 4
HZQKMZGKYVDMCT-GBXIJSLDSA-N (1s,2s)-2-fluorocyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1C[C@@H]1F HZQKMZGKYVDMCT-GBXIJSLDSA-N 0.000 description 3
XRKSEEMBEXHDLZ-UHFFFAOYSA-N 1-benzyl-2-oxopyrrolidine-3-carboxylic acid Chemical compound O=C1C(C(=O)O)CCN1CC1=CC=CC=C1 XRKSEEMBEXHDLZ-UHFFFAOYSA-N 0.000 description 3
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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 3
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
241000283690 Bos taurus Species 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
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NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
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239000012298 atmosphere Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
239000013522 chelant Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
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MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
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125000004430 oxygen atom Chemical group O* 0.000 description 3
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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238000000926 separation method Methods 0.000 description 3
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239000002585 base Substances 0.000 description 2
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229940031000 streptococcus pneumoniae Drugs 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
PRJKGYPRCXZNFO-AWEZNQCLSA-N tert-butyl (3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-3-carboxylate Chemical compound CC(C)(C)OC(=O)N[C@@]1(C(=O)OC(C)(C)C)CCNC1 PRJKGYPRCXZNFO-AWEZNQCLSA-N 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
DQQJBEAXSOOCPG-ZETCQYMHSA-N tert-butyl n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCNC1 DQQJBEAXSOOCPG-ZETCQYMHSA-N 0.000 description 1
BKITXDSDJGOXPN-JGVFFNPUSA-N tert-butyl n-[(3s,4s)-4-methylpyrrolidin-3-yl]carbamate Chemical compound C[C@H]1CNC[C@H]1NC(=O)OC(C)(C)C BKITXDSDJGOXPN-JGVFFNPUSA-N 0.000 description 1
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
101150068774 thyX gene Proteins 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
206010044008 tonsillitis Diseases 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
208000000143 urethritis Diseases 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)
Quinoline Compounds (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

LVP-92-696A 1988-04-27 1992-12-30 Optically active pyridoncarboxylic acid derivatives LV10092B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP10462588		1988-04-27
JP29698488		1988-11-24

Publications (1)

Publication Number	Publication Date
LV10092B true LV10092B (en)	1995-02-20

Family

ID=26445063

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-92-696A LV10092B (en)	1988-04-27	1992-12-30	Optically active pyridoncarboxylic acid derivatives

Country Status (25)

Country	Link
US (4)	US5587386A (fr)
EP (1)	EP0341493B1 (fr)
JP (5)	JP2714597B2 (fr)
KR (1)	KR0184614B1 (fr)
CN (1)	CN1033751C (fr)
AT (1)	ATE182145T1 (fr)
AU (1)	AU625414B2 (fr)
BG (1)	BG61122B2 (fr)
CA (1)	CA1340801C (fr)
DE (1)	DE68929030T2 (fr)
DK (1)	DK175467B1 (fr)
ES (1)	ES2135372T3 (fr)
FI (1)	FI96947C (fr)
GR (1)	GR3031365T3 (fr)
HU (1)	HU211136A9 (fr)
IL (1)	IL90062A (fr)
LV (1)	LV10092B (fr)
MY (1)	MY105136A (fr)
NO (1)	NO175939C (fr)
NZ (1)	NZ228893A (fr)
PT (1)	PT90377B (fr)
RU (1)	RU2075475C1 (fr)
SG (1)	SG48036A1 (fr)
UA (1)	UA29378C2 (fr)
YU (1)	YU48432B (fr)

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KR970704693A (ko) *	1994-07-18	1997-09-06	나가히로 마오미	트리플루오로메틸퀴놀린카르복실산 유도체(trifluoromethylquinolinecarboxylic acid derivative)
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JPH09124556A (ja)	1995-08-30	1997-05-13	Dai Ichi Seiyaku Co Ltd	ハロゲン化シクロプロパン誘導体の製造方法
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ID16655A (id) *	1996-04-24	1997-10-30	Daiichi Seiyaku Co	Turunan-turunan sikloalkilaminometilpirolidina
AU1040597A (en) *	1996-12-04	1998-06-29	Daiichi Pharmaceutical Co., Ltd.	Substituted aminomethylpyrrolidine derivatives
ES2244248T3 (es)	1998-11-24	2005-12-01	Daiichi Pharmaceutical Co., Ltd.	Derivados de aminometilpirrolidina sustituidos por cicloalquilos.
AU2940300A (en)	1999-03-10	2000-09-28	Daiichi Pharmaceutical Co., Ltd.	Aminomethylpyrrolidine derivatives having aromatic substituents
AU3192700A (en)	1999-03-17	2000-10-04	Daiichi Pharmaceutical Co., Ltd.	Medicinal compositions
MXPA02007667A (es)	2000-02-09	2003-04-14	Daiichi Seiyaku Co	Agentes antibacterianos antiacidos-resistentes que contienen acidos piridoncarboxilicos como el ingrediente activo.
BR0111248A (pt) *	2000-03-31	2003-07-08	Daiichi Seiyaku Co	Derivados de ácido quinolonacarboxìlico
CN1326524C (zh)	2000-04-24	2007-07-18	第一制药株式会社	稳定的液体制剂
KR100878667B1 (ko) *	2000-08-08	2009-01-13	다이이찌 세이야꾸 가부시기가이샤	고흡수성 고형 제제
RU2004136997A (ru) *	2002-05-17	2005-06-27	Дайити Фармасьютикал Ко., Лтд. (JP)	Способ получения производных хинолонкарбоновой кислоты
ATE488489T1 (de) *	2003-01-07	2010-12-15	Daiichi Sankyo Co Ltd	Verfahren zur reduktiven deshalogenierung
US7085154B2 (en) *	2003-06-03	2006-08-01	Samsung Electronics Co., Ltd.	Device and method for pulse width control in a phase change memory device
WO2005111015A1 (fr) *	2004-05-13	2005-11-24	Daiichi Pharmaceutical Co., Ltd.	Dérivé de pyrrolidine substituée
RU2420524C2 (ru) *	2005-05-19	2011-06-10	Дайити Санкио Компани, Лимитед	Производные три- или тетра-замещенного-3-аминопирролидина
JP5063032B2 (ja) *	2005-05-19	2012-10-31	第一三共株式会社	トリ−、テトラ−置換−３−アミノピロリジン誘導体
US7563805B2 (en)	2005-05-19	2009-07-21	Daiichi Pharmaceutical Co., Ltd.	Tri-, tetra-substituted-3-aminopyrrolidine derivative
US7928232B2 (en) *	2005-05-20	2011-04-19	Daiichi Sankyo Company, Limited	Method for producing asymmetric tetrasubstituted carbon atom-containing compound
US7977346B2 (en)	2006-01-17	2011-07-12	Guoqing Paul Chen	Spiro compounds and methods of use
TWI386401B (zh) *	2006-03-27	2013-02-21	Daiichi Seiyaku Co	醫藥用水合物
MY162052A (en)	2007-01-05	2017-05-31	Daiichi Sankyo Co Ltd	Fused substitute aminopyrrolidine derivative
ES2401415T3 (es)	2008-07-11	2013-04-19	Sumitomo Chemical Company, Limited	Procedimiento para producir el ácido (1S, 2R)-2-cloro-2-fluorociclopropanocarboxílico
FR2961207B1 (fr) *	2010-06-09	2013-01-18	Oreal	Utilisation d'un derive de 4- carboxy 2-pyrrolidinone comme solvant dans les compositions cosmetiques ; compositions cosmetiques les contenant ; nouveaux composes
CN103467448B (zh) *	2013-09-18	2015-04-15	浙江司太立制药股份有限公司	7-(3-氨基-4-烷氧亚胺基-1-哌啶基)-1-[(1r,2s)-2-氟环丙基]喹诺酮羧酸类化合物及其制备方法
EP2957561A1 (fr) *	2014-06-18	2015-12-23	Université Paris 6 Pierre et Marie Curie UPMC	Nouveaux fluoroquinolones et leur utilisation pour traiter des infections bactériennes
CN105330590B (zh) *	2015-10-15	2018-09-25	广州市朗启医药科技有限责任公司	西他沙星五元环侧链中间体的制备方法
CN109912504B (zh) *	2019-04-04	2020-11-10	山东省联合农药工业有限公司	一种喹啉羧酸类化合物及其制备方法与用途

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1989
- 1989-04-24 IL IL9006289A patent/IL90062A/en unknown
- 1989-04-24 MY MYPI89000521A patent/MY105136A/en unknown
- 1989-04-25 NO NO891698A patent/NO175939C/no not_active IP Right Cessation
- 1989-04-26 FI FI891980A patent/FI96947C/fi not_active IP Right Cessation
- 1989-04-26 PT PT90377A patent/PT90377B/pt not_active IP Right Cessation
- 1989-04-26 NZ NZ228893A patent/NZ228893A/xx unknown
- 1989-04-26 AU AU33702/89A patent/AU625414B2/en not_active Ceased
- 1989-04-26 JP JP1106762A patent/JP2714597B2/ja not_active Expired - Lifetime
- 1989-04-26 CA CA000597865A patent/CA1340801C/fr not_active Expired - Fee Related
- 1989-04-26 AT AT89107550T patent/ATE182145T1/de not_active IP Right Cessation
- 1989-04-26 ES ES89107550T patent/ES2135372T3/es not_active Expired - Lifetime
- 1989-04-26 DE DE68929030T patent/DE68929030T2/de not_active Expired - Lifetime
- 1989-04-26 YU YU87589A patent/YU48432B/sh unknown
- 1989-04-26 SG SG1996006401A patent/SG48036A1/en unknown
- 1989-04-26 EP EP89107550A patent/EP0341493B1/fr not_active Expired - Lifetime
- 1989-04-26 UA UA5001894A patent/UA29378C2/uk unknown
- 1989-04-27 CN CN89103911A patent/CN1033751C/zh not_active Expired - Lifetime
- 1989-04-27 DK DK205789A patent/DK175467B1/da not_active IP Right Cessation
- 1989-04-27 KR KR1019890005539A patent/KR0184614B1/ko not_active Expired - Lifetime
1991
- 1991-10-29 RU SU915001894A patent/RU2075475C1/ru not_active IP Right Cessation
1992
- 1992-12-30 LV LVP-92-696A patent/LV10092B/en unknown
1993
- 1993-10-28 US US08/142,105 patent/US5587386A/en not_active Ceased
1994
- 1994-02-28 BG BG098620A patent/BG61122B2/bg unknown
1995
- 1995-04-13 JP JP7088282A patent/JP2903292B2/ja not_active Expired - Lifetime
- 1995-06-07 US US08/477,886 patent/US5767127A/en not_active Expired - Lifetime
- 1995-06-22 HU HU95P/P00371P patent/HU211136A9/hu unknown
1997
- 1997-07-31 JP JP9205599A patent/JP2917010B2/ja not_active Expired - Fee Related
1998
- 1998-04-06 US US09/055,127 patent/US6031102A/en not_active Expired - Fee Related
- 1998-08-20 JP JP10233763A patent/JPH11124367A/ja active Pending
- 1998-08-20 JP JP10233764A patent/JPH11124380A/ja active Pending
1999
- 1999-09-29 GR GR990402459T patent/GR3031365T3/el unknown
2004
- 2004-06-03 US US10/859,587 patent/USRE41149E1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
YU48432B (sh)	1998-07-10
ATE182145T1 (de)	1999-07-15
FI891980A0 (fi)	1989-04-26
KR900016205A (ko)	1990-11-12
JP2714597B2 (ja)	1998-02-16
USRE41149E1 (en)	2010-02-23
ES2135372T3 (es)	1999-11-01
UA29378C2 (uk)	2000-11-15
EP0341493B1 (fr)	1999-07-14
EP0341493A2 (fr)	1989-11-15
DE68929030T2 (de)	2000-03-23
EP0341493A3 (fr)	1990-12-19
US5587386A (en)	1996-12-24
JPH11124380A (ja)	1999-05-11
CN1037507A (zh)	1989-11-29
CA1340801C (fr)	1999-10-26
GR3031365T3 (en)	2000-01-31
NO175939C (no)	1995-01-04
HU211136A9 (en)	1995-10-30
DK205789D0 (da)	1989-04-27
PT90377B (pt)	1994-09-30
NO175939B (no)	1994-09-26
DK205789A (da)	1989-10-28
JPH11124367A (ja)	1999-05-11
CN1033751C (zh)	1997-01-08
RU2075475C1 (ru)	1997-03-20
FI891980A7 (fi)	1989-10-28
JP2903292B2 (ja)	1999-06-07
NO891698L (no)	1989-10-30
PT90377A (pt)	1989-11-10
BG61122B2 (bg)	1996-11-29
JPH07300416A (ja)	1995-11-14
JP2917010B2 (ja)	1999-07-12
DK175467B1 (da)	2004-11-01
IL90062A0 (en)	1989-12-15
NZ228893A (en)	1990-06-26
US5767127A (en)	1998-06-16
MY105136A (en)	1994-08-30
YU87589A (en)	1990-12-31
JPH1067779A (ja)	1998-03-10
NO891698D0 (no)	1989-04-25
SG48036A1 (en)	1998-04-17
AU625414B2 (en)	1992-07-09
US6031102A (en)	2000-02-29
IL90062A (en)	1994-10-07
JPH02231475A (ja)	1990-09-13
FI96947B (fi)	1996-06-14
KR0184614B1 (ko)	1999-05-01
DE68929030D1 (de)	1999-08-19
FI96947C (fi)	1996-09-25
AU3370289A (en)	1989-11-02
HK1002108A1 (en)	1998-07-31

Publication	Publication Date	Title
LV10092B (en)	1995-02-20	Optically active pyridoncarboxylic acid derivatives
JP5475841B2 (ja)	2014-04-16	トリ−、テトラ−置換−３−アミノピロリジン誘導体
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