NO301165B1 - Bicykliske aminderivater og antibakterielle midler inneholdende disse - Google Patents

Bicykliske aminderivater og antibakterielle midler inneholdende disse Download PDF

Info

Publication number: NO301165B1
Authority: NO; Norway
Prior art keywords: compound; diazabicyclo; group; nonan; carboxylic acid
Prior art date: 1992-12-25

Application number

NO934753A

Other languages

English (en)

Norwegian (no)

Other versions

NO934753L (no

NO934753D0 (no

Inventor

Makoto Takemura

Youichi Kimura

Norikazu Matsuhashi

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.)

1992-12-25

Filing date

1993-12-22

Publication date

1997-09-22

1993-12-22 Application filed by Daiichi Seiyaku Co filed Critical Daiichi Seiyaku Co

1993-12-22 Publication of NO934753D0 publication Critical patent/NO934753D0/no

1994-06-27 Publication of NO934753L publication Critical patent/NO934753L/no

1997-09-22 Publication of NO301165B1 publication Critical patent/NO301165B1/no

Links

-1 Bicyclic amine Chemical class 0.000 title claims description 55
239000003242 anti bacterial agent Substances 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims abstract description 119
150000003839 salts Chemical group 0.000 claims abstract description 41
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
125000001424 substituent group Chemical group 0.000 claims abstract description 14
125000005843 halogen group Chemical group 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 8
UUEHXUCGEFZCDA-IGHBBLSQSA-N 7-[(4ar,7ar)-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b][1,4]oxazin-6-yl]-8-chloro-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3C[C@H]4OCCN[C@@H]4C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F UUEHXUCGEFZCDA-IGHBBLSQSA-N 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
ZBWXIXGIUYCWQU-JQWOWJDXSA-N 7-[(4as,7as)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-6,8-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3C[C@H]4NCCC[C@H]4C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F ZBWXIXGIUYCWQU-JQWOWJDXSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
QRIMBUOKWYXGCP-LNFKQOIKSA-N 7-[(4ar,7ar)-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b][1,4]oxazin-6-yl]-5-amino-6,8-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)C=2C(N)=C(F)C(N3C[C@H]4OCCN[C@@H]4C3)=C(F)C=2N1[C@@H]1C[C@@H]1F QRIMBUOKWYXGCP-LNFKQOIKSA-N 0.000 claims description 3
UUEHXUCGEFZCDA-SCUASFONSA-N 7-[(4as,7ar)-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b][1,4]oxazin-6-yl]-8-chloro-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3C[C@H]4OCCN[C@H]4C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F UUEHXUCGEFZCDA-SCUASFONSA-N 0.000 claims description 3
AVLNLRNVQDFBCK-OHBODLIOSA-N 7-[(4as,7as)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-5-amino-6,8-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)C=2C(N)=C(F)C(N3C[C@H]4NCCC[C@H]4C3)=C(F)C=2N1[C@@H]1C[C@@H]1F AVLNLRNVQDFBCK-OHBODLIOSA-N 0.000 claims description 3
KQXSUZGFVICWJM-HYEYJGRESA-N 7-[(4as,7as)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound CC1=C(N2C[C@H]3NCCC[C@H]3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2[C@@H]1C[C@@H]1F KQXSUZGFVICWJM-HYEYJGRESA-N 0.000 claims description 3
UMPPYKWIZQHDTA-GXTWGEPZSA-N 8-chloro-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxo-7-(2,3,4,6-tetrahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl)quinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3CC4=C(CNC4)C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F UMPPYKWIZQHDTA-GXTWGEPZSA-N 0.000 claims description 3
102100035593 POU domain, class 2, transcription factor 1 Human genes 0.000 claims description 3
101710084414 POU domain, class 2, transcription factor 1 Proteins 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 2
230000000845 anti-microbial effect Effects 0.000 abstract description 12
229910052757 nitrogen Inorganic materials 0.000 abstract description 7
125000004433 nitrogen atom Chemical group N* 0.000 abstract description 7
229910052799 carbon Inorganic materials 0.000 abstract description 3
230000003389 potentiating effect Effects 0.000 abstract 1
239000000203 mixture Substances 0.000 description 85
239000000243 solution Substances 0.000 description 82
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 80
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
239000002904 solvent Substances 0.000 description 57
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 46
238000005160 1H NMR spectroscopy Methods 0.000 description 41
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 26
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
101150041968 CDC13 gene Proteins 0.000 description 23
239000013078 crystal Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 20
150000007660 quinolones Chemical class 0.000 description 20
238000002844 melting Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
238000003756 stirring Methods 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
238000001914 filtration Methods 0.000 description 15
238000000921 elemental analysis Methods 0.000 description 14
238000010898 silica gel chromatography Methods 0.000 description 14
239000003480 eluent Substances 0.000 description 13
238000000034 method Methods 0.000 description 13
239000012044 organic layer Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
238000010992 reflux Methods 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
201000010099 disease Diseases 0.000 description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
238000001816 cooling Methods 0.000 description 8
239000000126 substance Substances 0.000 description 8
YSLIPUSJNFIFAB-UHFFFAOYSA-N 2-oxopyridine-1-carboxylic acid Chemical group OC(=O)N1C=CC=CC1=O YSLIPUSJNFIFAB-UHFFFAOYSA-N 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
239000003814 drug Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 6
229910052721 tungsten Inorganic materials 0.000 description 6
239000010937 tungsten Substances 0.000 description 6
HYNVUCYYHOBXLB-POYBYMJQSA-N 8-chloro-6,7-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F HYNVUCYYHOBXLB-POYBYMJQSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
239000000047 product Substances 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
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 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
150000003857 carboxamides Chemical class 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
229940079593 drug Drugs 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000010410 layer Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 3
TUKJTSUSKQOYCD-STHAYSLISA-N (1r,2s)-2-fluorocyclopropan-1-amine Chemical compound N[C@@H]1C[C@@H]1F TUKJTSUSKQOYCD-STHAYSLISA-N 0.000 description 3
ASQOQJYHIYYTEJ-GBESFXJTSA-N (1r,7s,9as)-7-decyl-2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-1-ol Chemical compound O[C@@H]1CCCN2C[C@@H](CCCCCCCCCC)CC[C@H]21 ASQOQJYHIYYTEJ-GBESFXJTSA-N 0.000 description 3
FXRYMAVXKXRENT-BNTLRKBRSA-N (4ar,7ar)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b][1,4]oxazine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.O1CCN[C@@H]2CNC[C@H]21 FXRYMAVXKXRENT-BNTLRKBRSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
206010039438 Salmonella Infections Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
239000004599 antimicrobial 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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
201000003146 cystitis Diseases 0.000 description 3
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
238000010438 heat treatment Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
230000002458 infectious effect Effects 0.000 description 3
244000005700 microbiome Species 0.000 description 3
GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
244000052769 pathogen Species 0.000 description 3
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 3
206010039447 salmonellosis Diseases 0.000 description 3
239000000725 suspension Substances 0.000 description 3
LGYOJUMUXCNZCD-BPLDGKMQSA-N tert-butyl (3r,4r)-3-hydroxy-4-[[(1r)-1-phenylethyl]amino]pyrrolidine-1-carboxylate Chemical compound N([C@H](C)C=1C=CC=CC=1)[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]1O LGYOJUMUXCNZCD-BPLDGKMQSA-N 0.000 description 3
LGEWGFOMLJQHLL-VHSXEESVSA-N tert-butyl (4as,7as)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]2CNC[C@@H]12 LGEWGFOMLJQHLL-VHSXEESVSA-N 0.000 description 3
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 3
238000005303 weighing Methods 0.000 description 3
AFYZAHZKOFBVLE-UONOGXRCSA-N (4as,7as)-6-benzyl-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C([C@H]1NCCC[C@H]1C1)N1CC1=CC=CC=C1 AFYZAHZKOFBVLE-UONOGXRCSA-N 0.000 description 2
HKROEBDHHKMNBZ-CHBKHGQFSA-N (ne)-n-[(e)-1-(4-fluorophenyl)-2-methylpent-1-en-3-ylidene]hydroxylamine Chemical compound CC\C(=N/O)\C(\C)=C\C1=CC=C(F)C=C1 HKROEBDHHKMNBZ-CHBKHGQFSA-N 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
HZQKMZGKYVDMCT-UHFFFAOYSA-N 2-fluorocyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1F HZQKMZGKYVDMCT-UHFFFAOYSA-N 0.000 description 2
RRBLNPCNHNHAFW-UHFFFAOYSA-N 6-benzyl-1,2,3,4,4a,7a-hexahydropyrrolo[3,4-b]pyridine-5,7-dione Chemical compound O=C1C2CCCNC2C(=O)N1CC1=CC=CC=C1 RRBLNPCNHNHAFW-UHFFFAOYSA-N 0.000 description 2
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 2
241000251468 Actinopterygii Species 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
208000003322 Coinfection Diseases 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000204031 Mycoplasma Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
206010035664 Pneumonia Diseases 0.000 description 2
206010040047 Sepsis Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
241000193996 Streptococcus pyogenes Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000002441 X-ray diffraction Methods 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
206010006451 bronchitis Diseases 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000009826 distribution Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
230000029142 excretion Effects 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000002008 hemorrhagic effect Effects 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
208000014674 injury Diseases 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
VWDJXAYQBSRYRB-UHFFFAOYSA-N nonane 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CCCCCCCCC VWDJXAYQBSRYRB-UHFFFAOYSA-N 0.000 description 2
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
206010039083 rhinitis Diseases 0.000 description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
BQVYNDNOBMOGJI-FVQBIDKESA-N tert-butyl (4ar,7ar)-3-oxo-4-[(1r)-1-phenylethyl]-4a,5,7,7a-tetrahydropyrrolo[3,4-b][1,4]oxazine-6-carboxylate Chemical compound C1([C@H](N2C(CO[C@@H]3CN(C[C@H]32)C(=O)OC(C)(C)C)=O)C)=CC=CC=C1 BQVYNDNOBMOGJI-FVQBIDKESA-N 0.000 description 2
CWXMPBSJFAXRLS-DJIMGWMZSA-N tert-butyl (4ar,7ar)-4-[(1r)-1-phenylethyl]-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carboxylate Chemical compound C1([C@H](N2[C@@H]3CN(C[C@H]3OCC2)C(=O)OC(C)(C)C)C)=CC=CC=C1 CWXMPBSJFAXRLS-DJIMGWMZSA-N 0.000 description 2
IWDFFHIOVOXFOW-UHFFFAOYSA-N tert-butyl 6-benzyl-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b]pyridine-1-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)CCCC2CN1CC1=CC=CC=C1 IWDFFHIOVOXFOW-UHFFFAOYSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
230000008733 trauma Effects 0.000 description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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 2
RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 1
KSCPLKVBWDOSAI-NKWVEPMBSA-N (4as,7as)-2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical compound N1CCC[C@H]2CNC[C@H]21 KSCPLKVBWDOSAI-NKWVEPMBSA-N 0.000 description 1
DPRJPRMZJGWLHY-HNGSOEQISA-N (e,3r,5s)-7-[5-(4-fluorophenyl)-3-propan-2-yl-1-pyrazin-2-ylpyrazol-4-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)/C=C/C=1C(C(C)C)=NN(C=2N=CC=NC=2)C=1C1=CC=C(F)C=C1 DPRJPRMZJGWLHY-HNGSOEQISA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
KSCPLKVBWDOSAI-UHFFFAOYSA-N 2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical compound N1CCCC2CNCC21 KSCPLKVBWDOSAI-UHFFFAOYSA-N 0.000 description 1
JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
TXEBWPPWSVMYOA-UHFFFAOYSA-N 4-[3-[(1-amino-2-chloroethyl)amino]propyl]-1-[[3-(2-chlorophenyl)phenyl]methyl]-5-hydroxyimidazolidin-2-one Chemical compound NC(CCl)NCCCC1NC(=O)N(Cc2cccc(c2)-c2ccccc2Cl)C1O TXEBWPPWSVMYOA-UHFFFAOYSA-N 0.000 description 1
WCDLCPLAAKUJNY-UHFFFAOYSA-N 4-[4-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CN3N=CC(=C3N=C2)C2=CNN=C2)C=C1 WCDLCPLAAKUJNY-UHFFFAOYSA-N 0.000 description 1
ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 description 1
KUZSBKJSGSKPJH-VXGBXAGGSA-N 5-[(9R)-6-[(3R)-3-methylmorpholin-4-yl]-11-oxa-1,3,5-triazatricyclo[7.4.0.02,7]trideca-2,4,6-trien-4-yl]pyrazin-2-amine Chemical compound C[C@@H]1COCCN1c1nc(nc2N3CCOC[C@H]3Cc12)-c1cnc(N)cn1 KUZSBKJSGSKPJH-VXGBXAGGSA-N 0.000 description 1
AFYZAHZKOFBVLE-UHFFFAOYSA-N 6-benzyl-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C1C2CCCNC2CN1CC1=CC=CC=C1 AFYZAHZKOFBVLE-UHFFFAOYSA-N 0.000 description 1
DWUBVULEMQOCPO-UHFFFAOYSA-N 6-benzylpyrrolo[3,4-b]pyridine-5,7-dione Chemical compound O=C1C2=NC=CC=C2C(=O)N1CC1=CC=CC=C1 DWUBVULEMQOCPO-UHFFFAOYSA-N 0.000 description 1
UUWKINATYHETDG-PWUKJLEFSA-N 7-[(4as,7as)-1-[(2-methylpropan-2-yl)oxycarbonyl]-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b]pyridin-6-yl]-8-chloro-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@@H]1CCCN([C@@H]1C1)C(=O)OC(C)(C)C)N1C(C=1Cl)=C(F)C=C(C(C(C(O)=O)=C2)=O)C=1N2[C@@H]1C[C@@H]1F UUWKINATYHETDG-PWUKJLEFSA-N 0.000 description 1
MITGKKFYIJJQGL-UHFFFAOYSA-N 9-(4-chlorobenzoyl)-6-methylsulfonyl-2,3-dihydro-1H-carbazol-4-one Chemical compound ClC1=CC=C(C(=O)N2C3=CC=C(C=C3C=3C(CCCC2=3)=O)S(=O)(=O)C)C=C1 MITGKKFYIJJQGL-UHFFFAOYSA-N 0.000 description 1
241000588625 Acinetobacter sp. Species 0.000 description 1
206010000501 Acne conglobata Diseases 0.000 description 1
206010048946 Anal abscess Diseases 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
201000008283 Atrophic Rhinitis Diseases 0.000 description 1
241000271566 Aves Species 0.000 description 1
208000004429 Bacillary Dysentery Diseases 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
206010004016 Bacterial diarrhoea Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000588807 Bordetella Species 0.000 description 1
208000031462 Bovine Mastitis Diseases 0.000 description 1
206010006458 Bronchitis chronic Diseases 0.000 description 1
QUMCIHKVKQYNPA-RUZDIDTESA-N C1(CCCCC1)CN1[C@@H](C=2N(C=3C=NC(=NC1=3)NC1=C(C=C(C(=O)NC3CCN(CC3)C)C=C1)OC)C(=NN=2)C)CC Chemical compound C1(CCCCC1)CN1[C@@H](C=2N(C=3C=NC(=NC1=3)NC1=C(C=C(C(=O)NC3CCN(CC3)C)C=C1)OC)C(=NN=2)C)CC QUMCIHKVKQYNPA-RUZDIDTESA-N 0.000 description 1
QCMHGCDOZLWPOT-FMNCTDSISA-N COC1=C(CC[C@@H]2CCC3=C(C2)C=CC(=C3)[C@H]2CC[C@](N)(CO)C2)C=CC=C1 Chemical compound COC1=C(CC[C@@H]2CCC3=C(C2)C=CC(=C3)[C@H]2CC[C@](N)(CO)C2)C=CC=C1 QCMHGCDOZLWPOT-FMNCTDSISA-N 0.000 description 1
241000589994 Campylobacter sp. Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
206010007882 Cellulitis Diseases 0.000 description 1
241000606153 Chlamydia trachomatis Species 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
206010008631 Cholera Diseases 0.000 description 1
208000014085 Chronic respiratory disease Diseases 0.000 description 1
241000873310 Citrobacter sp. Species 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
238000006969 Curtius rearrangement reaction Methods 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
208000004232 Enteritis Diseases 0.000 description 1
241000147019 Enterobacter sp. Species 0.000 description 1
201000000297 Erysipelas Diseases 0.000 description 1
241000588722 Escherichia Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
206010017915 Gastroenteritis shigella Diseases 0.000 description 1
241000606790 Haemophilus Species 0.000 description 1
241000606768 Haemophilus influenzae Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
ZNSPHKJFQDEABI-NZQKXSOJSA-N Nc1nc(O[C@H](c2ccc(Cl)cc2-c2ccccc2)C(F)(F)F)cc(n1)N1CCC2(CN[C@@H](C2)C(O)=O)CC1 Chemical compound Nc1nc(O[C@H](c2ccc(Cl)cc2-c2ccccc2)C(F)(F)F)cc(n1)N1CCC2(CN[C@@H](C2)C(O)=O)CC1 ZNSPHKJFQDEABI-NZQKXSOJSA-N 0.000 description 1
241000588652 Neisseria gonorrhoeae Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241000606860 Pasteurella Species 0.000 description 1
206010034107 Pasteurella infections Diseases 0.000 description 1
241000334216 Proteus sp. Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
206010037596 Pyelonephritis Diseases 0.000 description 1
206010037651 Pyometra Diseases 0.000 description 1
206010039088 Rhinitis atrophic Diseases 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
241000607714 Serratia sp. Species 0.000 description 1
241000607758 Shigella sp. Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
241000295644 Staphylococcaceae Species 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
241000193998 Streptococcus pneumoniae Species 0.000 description 1
206010042343 Subcutaneous abscess Diseases 0.000 description 1
241000282887 Suidae Species 0.000 description 1
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 1
206010000269 abscess Diseases 0.000 description 1
239000003655 absorption accelerator Substances 0.000 description 1
YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001334 alicyclic compounds Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
229940064004 antiseptic throat preparations Drugs 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
210000000941 bile Anatomy 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
201000009267 bronchiectasis Diseases 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
AEULIVPVIDOLIN-UHFFFAOYSA-N cep-11981 Chemical compound C1=C2C3=C4CNC(=O)C4=C4C5=CN(C)N=C5CCC4=C3N(CC(C)C)C2=CC=C1NC1=NC=CC=N1 AEULIVPVIDOLIN-UHFFFAOYSA-N 0.000 description 1
239000013522 chelant Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000013330 chicken meat Nutrition 0.000 description 1
208000003167 cholangitis Diseases 0.000 description 1
201000001352 cholecystitis Diseases 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
208000007451 chronic bronchitis Diseases 0.000 description 1
201000009151 chronic rhinitis Diseases 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229940125876 compound 15a Drugs 0.000 description 1
229940125890 compound Ia Drugs 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
206010062952 diffuse panbronchiolitis Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
201000010063 epididymitis Diseases 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LZMXLCPYJNRWNQ-UHFFFAOYSA-N ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC(F)=C(F)C(Cl)=C1F LZMXLCPYJNRWNQ-UHFFFAOYSA-N 0.000 description 1
NCRBEUVYYNMIBX-WCBMZHEXSA-N ethyl 8-chloro-6,7-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylate Chemical compound C12=C(Cl)C(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1[C@@H]1C[C@@H]1F NCRBEUVYYNMIBX-WCBMZHEXSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
IZZJFOLOOYFYFG-VKHMYHEASA-N fluorocyclopropane Chemical group F[C@H]1[CH]C1 IZZJFOLOOYFYFG-VKHMYHEASA-N 0.000 description 1
125000006419 fluorocyclopropyl group Chemical group 0.000 description 1
230000003325 follicular Effects 0.000 description 1
235000013305 food Nutrition 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
208000020426 gonococcal urethritis Diseases 0.000 description 1
229940047650 haemophilus influenzae Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
MOTRZVVGCFFABN-UHFFFAOYSA-N hexane;2-propan-2-yloxypropane Chemical compound CCCCCC.CC(C)OC(C)C MOTRZVVGCFFABN-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
201000003265 lymphadenitis Diseases 0.000 description 1
206010025226 lymphangitis Diseases 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
YRCHYHRCBXNYNU-UHFFFAOYSA-N n-[[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]carbamothioyl]-2-(4-fluorophenyl)acetamide Chemical compound N1=CC(CNCCOC)=CC=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=S)NC(=O)CC=4C=CC(F)=CC=4)=CC=3)F)=C2S1 YRCHYHRCBXNYNU-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
238000005192 partition Methods 0.000 description 1
201000005115 pasteurellosis Diseases 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
208000008423 pleurisy Diseases 0.000 description 1
201000006509 pleuropneumonia Diseases 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
201000007094 prostatitis Diseases 0.000 description 1
201000002765 pyometritis Diseases 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
201000005113 shigellosis Diseases 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229940031000 streptococcus pneumoniae Drugs 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
IWDFFHIOVOXFOW-DLBZAZTESA-N tert-butyl (4as,7as)-6-benzyl-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b]pyridine-1-carboxylate Chemical compound C([C@@H]1CCCN([C@@H]1C1)C(=O)OC(C)(C)C)N1CC1=CC=CC=C1 IWDFFHIOVOXFOW-DLBZAZTESA-N 0.000 description 1
LGEWGFOMLJQHLL-UHFFFAOYSA-N tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC2CNCC12 LGEWGFOMLJQHLL-UHFFFAOYSA-N 0.000 description 1
NXZIGGBPLGAPTI-UHFFFAOYSA-N tert-butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC2OC21 NXZIGGBPLGAPTI-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 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
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 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
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
208000000143 urethritis Diseases 0.000 description 1
JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 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
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

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

NO934753A 1992-12-25 1993-12-22 Bicykliske aminderivater og antibakterielle midler inneholdende disse NO301165B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP34603092		1992-12-25

Publications (3)

Publication Number	Publication Date
NO934753D0 NO934753D0 (no)	1993-12-22
NO934753L NO934753L (no)	1994-06-27
NO301165B1 true NO301165B1 (no)	1997-09-22

Family

ID=18380663

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO934753A NO301165B1 (no)	1992-12-25	1993-12-22	Bicykliske aminderivater og antibakterielle midler inneholdende disse

Country Status (17)

Country	Link
US (1)	US5654318A (de)
EP (1)	EP0603887B1 (de)
JP (1)	JP3268098B2 (de)
KR (1)	KR100295483B1 (de)
CN (1)	CN1037441C (de)
AT (1)	ATE251157T1 (de)
AU (1)	AU669948B2 (de)
CA (1)	CA2112165C (de)
DE (1)	DE69333223T2 (de)
DK (1)	DK0603887T3 (de)
ES (1)	ES2208636T3 (de)
FI (1)	FI105031B (de)
NO (1)	NO301165B1 (de)
PH (1)	PH31587A (de)
PT (1)	PT603887E (de)
RU (1)	RU2125046C1 (de)
TW (1)	TW264476B (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR0148277B1 (ko) *	1993-01-18	1998-11-02	채영복	신규한 플루오르퀴놀론계 유도체 및 그의 제조방법
KR960004339A (ko) *	1994-07-02	1996-02-23	임성기	신규한 퀴놀린계 화합물 및 그 의 제조방법
AU3618595A (en) *	1994-10-06	1996-05-02	Dainippon Pharmaceutical Co. Ltd.	Pyridonecarboxylic acid derivative and intermediate for the synthesis of the same
DE19546249A1 (de) *	1995-12-12	1997-06-19	Bayer Ag	Neue Kristallmodifikation des 1-Cyclopropyl-7-([S,S]-2,8-diazabicyclo[4,3,0]non-8-yl)-6-fluor-1,4-dihydro-8-methoxy-4-oxo-3-chinolincarbonsäure Hydrochlorid (CDCH), Verfahren zu dessen Herstellung und diese enthaltende pharmazeutische Zubereitungen
ATE228130T1 (de) *	1996-02-23	2002-12-15	Bayer Ag	Gegebenenfalls substituierte 8-cyan-1-cyclopropyl-7-(2,8-diazabicyclo- 4.3.0)-nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3- hinolincarbonsäuren und ihre derivate
AU704735B2 (en) *	1996-02-27	1999-04-29	Dainippon Pharmaceutical Co. Ltd.	Pyridonecarboxylic acid derivatives and intermediates for the synthesis thereo
KR100531967B1 (ko) *	1996-10-25	2005-11-30	다이이찌 세이야꾸 가부시기가이샤	트리사이클릭 아민 유도체, 이를 포함하는 항균제 및 퀴놀론 화합물의 제조방법
DE19652239A1 (de) *	1996-12-16	1998-06-18	Bayer Ag	Verwendung von 7-(2-Oxa-5,8-diazabicyclo[4.3.0]non-8-yl)-chinolon- und -naphthyridoncarbonsäure-Derivaten zur Therapie von Helicobacter-pylori-Infektionen und den damit assoziierten gastroduodenalen Erkrankungen
DE19821039A1 (de) *	1998-05-11	1999-11-18	Bayer Ag	Verfahren zur Herstellung von (S,S)-Benzyl-2,8-diazabicyclo[4.3.0]nonan
DE19931115A1 (de) *	1999-07-06	2001-01-11	Bayer Ag	Racemisierung von R, S-Dioxo-Benzylpyrrolopiperidin
CN1312131C (zh)	2000-02-09	2007-04-25	第一制药株式会社	包含作为活性成分的吡啶酮羧酸的抗耐酸细菌药
MY137020A (en)	2000-04-27	2008-12-31	Abbott Lab	Diazabicyclic central nervous system active agents
US6809105B2 (en)	2000-04-27	2004-10-26	Abbott Laboratories	Diazabicyclic central nervous system active agents
DE10022369A1 (de)	2000-05-08	2001-11-15	Bayer Ag	Verfahren zur Herstellung von Piperidinen
JP5069678B2 (ja) *	2005-05-25	2012-11-07	メルク・シャープ・エンド・ドーム・コーポレイション	糖尿病の治療又は予防のためのジペプチジルペプチダーゼｉｖ阻害剤としてのアミノシクロヘキサン
CN102101861B (zh) *	2008-07-01	2012-07-18	韶远化学科技（上海）有限公司	含氮双杂环医药中间体的合成及工艺方法
EA201101564A1 (ru)	2009-05-15	2012-07-30	Редкс Фарма Лимитед	Редокс производные лекарственных средств
CN102675308A (zh) *	2011-03-17	2012-09-19	苏州中科天马肽工程中心有限公司	一种制备8-苄基-2,8-二氮杂二环[4.3.0]壬烷的方法

Family Cites Families (14)

* 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
NZ210805A (en) *	1984-01-19	1988-04-29	Norton Co	Aluminous abrasive grits or shaped bodies
EP0191185B1 (de) *	1984-12-14	1990-03-07	Daiichi Seiyaku Co., Ltd.	Chinolincarbonsäure-Derivate
DE3509546A1 (de) *	1985-03-16	1986-09-25	Bayer Ag, 5090 Leverkusen	7-amino-1-(subst.cyclopropyl)-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
MY105136A (en) *	1988-04-27	1994-08-30	Daiichi Seiyaku Co	Optically active pyridonecarboxylic acid derivatives.
DE3906365A1 (de) *	1988-07-15	1990-01-18	Bayer Ag	7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe
DE3910663A1 (de) *	1989-04-03	1990-10-04	Bayer Ag	5-alkylchinoloncarbonsaeuren
KR910009330B1 (ko) *	1989-10-23	1991-11-11	재단법인 한국화학연구소	항균작용을 갖는 퀴놀린계 화합물과 그의 제조방법
CA2030217A1 (en) *	1989-11-21	1991-05-22	Jun Imose	Pyridone-carboxylic acid derivatives useful as veterinary medicines
JPH03188080A (ja) *	1989-12-15	1991-08-16	Banyu Pharmaceut Co Ltd	ピリドンカルボン酸誘導体
DE4032560A1 (de) *	1990-10-13	1992-04-16	Bayer Ag	7-(2,7-diazabicyclo(3.3.0)octyl)-3-chinolon- und -naphtyridoncarbonsaeure-derivate
US5696132A (en) *	1991-05-28	1997-12-09	Daiichi Pharmaceutical Co., Ltd.	Pyridonecarboxylic acid derivatives
TW209865B (de) *	1992-01-10	1993-07-21	Bayer Ag
DE4230804A1 (de) *	1992-09-15	1994-03-17	Bayer Ag	7-Isoindolinyl-chinolon- und -naphthyridon-Derivate

1993
- 1993-12-22 NO NO934753A patent/NO301165B1/no not_active IP Right Cessation
- 1993-12-22 JP JP32301193A patent/JP3268098B2/ja not_active Expired - Fee Related
- 1993-12-22 CA CA002112165A patent/CA2112165C/en not_active Expired - Fee Related
- 1993-12-23 ES ES93120802T patent/ES2208636T3/es not_active Expired - Lifetime
- 1993-12-23 DE DE69333223T patent/DE69333223T2/de not_active Expired - Fee Related
- 1993-12-23 AT AT93120802T patent/ATE251157T1/de not_active IP Right Cessation
- 1993-12-23 EP EP93120802A patent/EP0603887B1/de not_active Expired - Lifetime
- 1993-12-23 DK DK93120802T patent/DK0603887T3/da active
- 1993-12-23 TW TW082110919A patent/TW264476B/zh active
- 1993-12-23 PT PT93120802T patent/PT603887E/pt unknown
- 1993-12-23 FI FI935830A patent/FI105031B/fi not_active IP Right Cessation
- 1993-12-23 RU RU93056853A patent/RU2125046C1/ru not_active IP Right Cessation
- 1993-12-23 AU AU52695/93A patent/AU669948B2/en not_active Ceased
- 1993-12-23 US US08/172,233 patent/US5654318A/en not_active Expired - Lifetime
- 1993-12-24 PH PH47546A patent/PH31587A/en unknown
- 1993-12-24 KR KR1019930029472A patent/KR100295483B1/ko not_active Expired - Fee Related
- 1993-12-25 CN CN93121757A patent/CN1037441C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0603887A3 (de)	1995-04-26
DE69333223T2 (de)	2004-08-05
JP3268098B2 (ja)	2002-03-25
PH31587A (en)	1998-11-03
CA2112165C (en)	2003-04-08
FI935830A0 (fi)	1993-12-23
PT603887E (pt)	2004-02-27
CN1037441C (zh)	1998-02-18
JPH06239857A (ja)	1994-08-30
ES2208636T3 (es)	2004-06-16
KR940014397A (ko)	1994-07-18
ATE251157T1 (de)	2003-10-15
EP0603887A2 (de)	1994-06-29
DK0603887T3 (da)	2004-01-26
US5654318A (en)	1997-08-05
RU2125046C1 (ru)	1999-01-20
NO934753L (no)	1994-06-27
NO934753D0 (no)	1993-12-22
EP0603887B1 (de)	2003-10-01
CN1095068A (zh)	1994-11-16
AU669948B2 (en)	1996-06-27
AU5269593A (en)	1994-07-07
DE69333223D1 (de)	2003-11-06
FI935830L (fi)	1994-06-26
FI105031B (fi)	2000-05-31
KR100295483B1 (ko)	2001-09-17
CA2112165A1 (en)	1994-06-26
TW264476B (de)	1995-12-01

Legal Events

Date	Code	Title	Description
2005-09-12	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US5587386A (en)	1996-12-24	Optically active pyridonecarboxylic acid derivatives
NO301165B1 (no)	1997-09-22	Bicykliske aminderivater og antibakterielle midler inneholdende disse
IE63492B1 (en)	1995-05-03	A Spiro Compound
JP3215500B2 (ja)	2001-10-09	ピリドンカルボン酸誘導体
US6586604B2 (en)	2003-07-01	Tricyclic amine derivatives
JP4094061B2 (ja)	2008-06-04	シス置換アミノシクロプロパン誘導体
JPWO1998002431A1 (ja)	1999-08-24	シス置換アミノシクロプロパン誘導体
JPH10287669A (ja)	1998-10-27	置換アミノメチルピロリジン誘導体
KR100551462B1 (ko)	2006-02-14	치환된 사이클로부틸아민 유도체
EP0488227B1 (de)	1997-02-26	Optisch aktive Pyridobenzoxazinderivate
JPH0372476A (ja)	1991-03-27	光学活性キノロンカルボン酸誘導体
JP4132155B2 (ja)	2008-08-13	三環性アミン誘導体
WO1996024593A1 (en)	1996-08-15	Heterocyclic spiro derivatives
JPWO1992021659A1 (ja)	1993-06-03	ピリドンカルボン酸誘導体
JPH1081682A (ja)	1998-03-31	シス置換アミノシクロプロパン誘導体
WO1998024781A1 (en)	1998-06-11	Substituted aminomethylpyrrolidine derivatives