JP2003012667A - キノリンカルボキサミド骨格を有する抗菌剤 - Google Patents

キノリンカルボキサミド骨格を有する抗菌剤

Info

Publication number: JP2003012667A
Authority: JP; Japan
Prior art keywords: group; compound; atom; independently; lower alkyl
Prior art date: 2001-06-26
Legal status (The legal status 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 status listed.): Pending

Application number

JP2001192416A

Other languages

English (en)

Japanese (ja)

Inventor

Minoru Yasuda

実安田

Koichi Ikesue

公一池末

Yutaka Maeda

豊前田

Toshio Yoshida

稔夫吉田

Mihoko Nakajima

充保子中島

Hiroto Hara

裕人原

Kazuteru Yokose

一輝横瀬

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

RRF KENKYUSHO KK

Original Assignee

RRF KENKYUSHO KK

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.)

2001-06-26

Filing date

2001-06-26

Publication date

2003-01-15

2001-06-26 Application filed by RRF KENKYUSHO KK filed Critical RRF KENKYUSHO KK

2001-06-26 Priority to JP2001192416A priority Critical patent/JP2003012667A/ja

2002-06-26 Priority to PCT/JP2002/006395 priority patent/WO2003000681A1/fr

2003-01-15 Publication of JP2003012667A publication Critical patent/JP2003012667A/ja

Status Pending legal-status Critical Current

Links

ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 title claims abstract description 13
239000004599 antimicrobial Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 54
125000000217 alkyl group Chemical group 0.000 claims abstract description 28
125000005843 halogen group Chemical group 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
229910052757 nitrogen Chemical group 0.000 claims abstract description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
229910052799 carbon Inorganic materials 0.000 claims abstract description 9
125000004076 pyridyl group Chemical group 0.000 claims abstract description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 7
125000005956 isoquinolyl group Chemical group 0.000 claims abstract description 7
125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 7
125000005412 pyrazyl group Chemical group 0.000 claims abstract description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000005493 quinolyl group Chemical group 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
239000003242 anti bacterial agent Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
241000192125 Firmicutes Species 0.000 abstract description 11
230000000845 anti-microbial effect Effects 0.000 abstract 1
230000000844 anti-bacterial effect Effects 0.000 description 15
125000001424 substituent group Chemical group 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
125000003545 alkoxy group Chemical group 0.000 description 9
-1 for example Chemical group 0.000 description 8
239000002904 solvent Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
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239000012312 sodium hydride Substances 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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125000002252 acyl group Chemical group 0.000 description 3
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125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
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UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000010410 layer Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000002674 ointment Substances 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
NNQDMQVWOWCVEM-NSCUHMNNSA-N (e)-1-bromoprop-1-ene Chemical compound C\C=C\Br NNQDMQVWOWCVEM-NSCUHMNNSA-N 0.000 description 1
UXTZUUVTGMDXNG-UHFFFAOYSA-N 1,2-benzoxazine-3,4-dione Chemical compound C1=CC=C2C(=O)C(=O)NOC2=C1 UXTZUUVTGMDXNG-UHFFFAOYSA-N 0.000 description 1
XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical group C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
241000194033 Enterococcus Species 0.000 description 1
241000194032 Enterococcus faecalis Species 0.000 description 1
241000194031 Enterococcus faecium Species 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
101000879758 Homo sapiens Sjoegren syndrome nuclear autoantigen 1 Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
102100037330 Sjoegren syndrome nuclear autoantigen 1 Human genes 0.000 description 1
241000191963 Staphylococcus epidermidis Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
108010059993 Vancomycin Proteins 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
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125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
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238000010998 test method Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
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125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
229960003165 vancomycin Drugs 0.000 description 1
MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1

Classifications

- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP2001192416A 2001-06-26 2001-06-26 キノリンカルボキサミド骨格を有する抗菌剤 Pending JP2003012667A (ja)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
JP2001192416A JP2003012667A (ja)	2001-06-26	2001-06-26	キノリンカルボキサミド骨格を有する抗菌剤
PCT/JP2002/006395 WO2003000681A1 (fr)	2001-06-26	2002-06-26	Compose antibacterien comprenant un squelette quinolinecarboxamide

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2001192416A JP2003012667A (ja)	2001-06-26	2001-06-26	キノリンカルボキサミド骨格を有する抗菌剤

Publications (1)

Publication Number	Publication Date
JP2003012667A true JP2003012667A (ja)	2003-01-15

Family

ID=19030870

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2001192416A Pending JP2003012667A (ja)	2001-06-26	2001-06-26	キノリンカルボキサミド骨格を有する抗菌剤

Country Status (2)

Country	Link
JP (1)	JP2003012667A (fr)
WO (1)	WO2003000681A1 (fr)

Cited By (10)

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JP2007169259A (ja) *	2005-07-14	2007-07-05	Sumitomo Chemical Co Ltd	カルボキサミド化合物及びその植物病害防除用途
US7495103B2 (en)	2004-06-24	2009-02-24	Vertex Pharmaceuticals Incorporated	Modulators of ATP-binding cassette transporters
JP2009544732A (ja) *	2006-07-26	2009-12-17	ノバルティスアクチエンゲゼルシャフト	ウンデカプレニルピロホスフェートシンターゼの阻害剤
US9139530B2 (en)	2005-12-28	2015-09-22	Vertex Pharmaceuticals Incorporated	Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US9701639B2 (en)	2014-10-07	2017-07-11	Vertex Pharmaceuticals Incorporated	Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator
JP2017523213A (ja) *	2014-08-06	2017-08-17	ノバルティスアーゲー	抗菌薬としてのキノロン誘導体
US9751839B2 (en)	2009-03-20	2017-09-05	Vertex Pharmaceuticals Incorporated	Process for making modulators of cystic fibrosis transmembrane conductance regulator
US10272046B2 (en)	2012-02-27	2019-04-30	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof
US10646481B2 (en)	2008-08-13	2020-05-12	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof
US12458635B2 (en)	2008-08-13	2025-11-04	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof

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KR20130065728A (ko)	2010-10-14	2013-06-19	임뮤나르 에이비	Ahr 활성화제로서의 1,2-디히드로-4-히드록시-2-옥소-퀴놀린-3-카르복사닐리드
CN113307768B (zh) *	2021-04-29	2023-12-12	中国农业科学院兰州畜牧与兽药研究所	喹诺酮类衍生物及其制备方法和用途

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE52670B1 (en) *	1981-03-03	1988-01-20	Leo Ab	Heterocyclic carboxamides,compositions containing such compounds,and processes for their preparation

2001
- 2001-06-26 JP JP2001192416A patent/JP2003012667A/ja active Pending
2002
- 2002-06-26 WO PCT/JP2002/006395 patent/WO2003000681A1/fr not_active Ceased

Cited By (20)

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Publication number	Priority date	Publication date	Assignee	Title
US10662192B2 (en)	2004-06-24	2020-05-26	Vertex Pharmaceuticals Incorporated	Modulators of ATP-binding cassette transporters
US7495103B2 (en)	2004-06-24	2009-02-24	Vertex Pharmaceuticals Incorporated	Modulators of ATP-binding cassette transporters
US9090619B2 (en)	2004-06-24	2015-07-28	Vertex Pharmaceuticals Incorporated	Modulators of ATP-binding cassette transporters
JP2007169259A (ja) *	2005-07-14	2007-07-05	Sumitomo Chemical Co Ltd	カルボキサミド化合物及びその植物病害防除用途
US11291662B2 (en)	2005-12-28	2022-04-05	Vertex Pharmaceuticals Incorporated	Solid forms of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US9139530B2 (en)	2005-12-28	2015-09-22	Vertex Pharmaceuticals Incorporated	Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US9670163B2 (en)	2005-12-28	2017-06-06	Vertex Pharmaceuticals Incorporated	Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US9931334B2 (en)	2005-12-28	2018-04-03	Vertex Pharmaceuticals Incorporated	Solid forms of N[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US10537565B2 (en)	2005-12-28	2020-01-21	Vertex Pharmaceuticals Incorporated	Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
JP2009544732A (ja) *	2006-07-26	2009-12-17	ノバルティスアクチエンゲゼルシャフト	ウンデカプレニルピロホスフェートシンターゼの阻害剤
US12458635B2 (en)	2008-08-13	2025-11-04	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof
US11564916B2 (en)	2008-08-13	2023-01-31	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof
US10646481B2 (en)	2008-08-13	2020-05-12	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof
US9751839B2 (en)	2009-03-20	2017-09-05	Vertex Pharmaceuticals Incorporated	Process for making modulators of cystic fibrosis transmembrane conductance regulator
US11147770B2 (en)	2012-02-27	2021-10-19	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof
US10272046B2 (en)	2012-02-27	2019-04-30	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof
US11752106B2 (en)	2012-02-27	2023-09-12	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof
US12214083B2 (en)	2012-02-27	2025-02-04	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof
JP2017523213A (ja) *	2014-08-06	2017-08-17	ノバルティスアーゲー	抗菌薬としてのキノロン誘導体
US9701639B2 (en)	2014-10-07	2017-07-11	Vertex Pharmaceuticals Incorporated	Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator

Also Published As

Publication number	Publication date
WO2003000681A1 (fr)	2003-01-03

Publication	Publication Date	Title
TWI282335B (en)	2007-06-11	A61k 31/437 200601 a i vhtw a61p 31/04 200601 a i vhtw
JPS62161763A (ja)	1987-07-17	７‐アミノ‐１シクロプロピル‐４‐オキソ‐１，４‐ジヒドロ‐ナフチリジンまたは‐キノリン‐３‐カルボン酸類またはその塩及びそれらの製造法
JP2004522792A5 (fr)	2006-01-05
WO1992009279A1 (fr)	1992-06-11	Derive de 2-arylthiazole et composition pharmaceutique contenant ce derive
TW200410963A (en)	2004-07-01	Heterocyclic derivatives
JPH0710848B2 (ja)	1995-02-08	ピリジン−３−カルボキサミド誘導体
KR100602977B1 (ko)	2006-07-20	안트라닐산 아미드 및 ｖｅｇｆ 수용체 티로신 키나제억제제로서 그의 용도
JP2002020386A (ja)	2002-01-23	ピラゾロピリジン誘導体
JPH02289548A (ja)	1990-11-29	ピリジン化合物
WO2003000681A1 (fr)	2003-01-03	Compose antibacterien comprenant un squelette quinolinecarboxamide
CN105814018B (zh)	2018-03-20	新型脲类化合物、制备方法及其用途
KR102076820B1 (ko)	2020-02-13	신규한 항진균성 옥소다이하이드로피리딘카보하이드라자이드 유도체
JPH01146879A (ja)	1989-06-08	アゼチジニルキノロンカルボン酸とそのエステル類
JPH0317078A (ja)	1991-01-25	８‐置換４‐（ヘテロサイクリルメチルアミノ）‐キノリン
RU2236408C2 (ru)	2004-09-20	1-(6-амино-3,5-дифторпиридин-2-ил)-8-бром-7(3-этил-аминоазетидин-1-ил)-6- фтор-4-оксо-1,4-дигидрохинолин-3-карбоновая кислота, лекарственная композиция и способ лечения на основе этого соединения
JP4294469B2 (ja)	2009-07-15	Ｐｄｅｉｖ阻害剤
JP2004137185A (ja)	2004-05-13	チオフェン骨格を有する抗菌剤
HUP0204476A2 (en)	2003-05-28	Therapeutically useful new salts of cck inhibitors, process for the preparation thereof and pharmaceutical compositions containing them
CN116874468B (zh)	2025-08-29	具有2-吡啶取代甲酰胺结构的小分子化合物的合成和应用
JPH0240383A (ja)	1990-02-09	１，４−ジヒドロピリジン誘導体
DK1370539T3 (da)	2012-02-13	HIV-inhiberende N-aminoimidazolderivater
EP4085054B1 (fr)	2025-02-19	Nouveaux agonistes inverses pqsr
RU2822464C2 (ru)	2024-07-05	Ингибиторы аврора-киназы и их применение
JPH0616678A (ja)	1994-01-25	キノリンカルボン酸誘導体
JPH0616665A (ja)	1994-01-25	キノロンカルボン酸誘導体及び該化合物を有効成分とする抗菌剤