NO323563B1 - Heterocykliske quinolonforbindelser med antibakteriell effekt, farmasoytisk sammensetning omfattende slike samt anvendelse av slike forbindelser for fremstilling av antimikrobielle medikamenter - Google Patents
Heterocykliske quinolonforbindelser med antibakteriell effekt, farmasoytisk sammensetning omfattende slike samt anvendelse av slike forbindelser for fremstilling av antimikrobielle medikamenter Download PDFInfo
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- NO323563B1 NO323563B1 NO20001340A NO20001340A NO323563B1 NO 323563 B1 NO323563 B1 NO 323563B1 NO 20001340 A NO20001340 A NO 20001340A NO 20001340 A NO20001340 A NO 20001340A NO 323563 B1 NO323563 B1 NO 323563B1
- Authority
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- Norway
- Prior art keywords
- methoxy
- oxo
- dihydro
- amino
- cyclopropyl
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- 150000001875 compounds Chemical class 0.000 title claims description 92
- -1 Heterocyclic quinolone compounds Chemical class 0.000 title claims description 66
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 title description 13
- 230000000845 anti-microbial effect Effects 0.000 title description 12
- 239000003814 drug Substances 0.000 title description 7
- 229940079593 drug Drugs 0.000 title description 7
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000001153 fluoro group Chemical group F* 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 208000015181 infectious disease Diseases 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 230000003287 optical effect Effects 0.000 claims description 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 230000000813 microbial effect Effects 0.000 claims description 7
- ZASYVQUJFRKPOO-UHFFFAOYSA-N 7-(3-aminopiperidin-1-yl)-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(N2CC(N)CCC2)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 ZASYVQUJFRKPOO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 4
- YGFPIYYPDFYIGE-UHFFFAOYSA-N 7-(3-amino-4-methylpiperidin-1-yl)-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(N2CC(N)C(C)CC2)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 YGFPIYYPDFYIGE-UHFFFAOYSA-N 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- LALGDARALUYBLT-UHFFFAOYSA-N 8-methoxy-4-oxo-1-propylquinoline-3-carboxylic acid Chemical compound C1=CC(OC)=C2N(CCC)C=C(C(O)=O)C(=O)C2=C1 LALGDARALUYBLT-UHFFFAOYSA-N 0.000 claims 5
- FUDKJNYIYARHMJ-UHFFFAOYSA-N 7-(3-amino-4-ethylpiperidin-1-yl)-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)C(CC)CCN1C1=CC=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1OC FUDKJNYIYARHMJ-UHFFFAOYSA-N 0.000 claims 1
- GNXOXGZXNPZHGK-UHFFFAOYSA-N 7-(4-amino-6-azaspiro[2.5]octan-2-yl)-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(C2C3(C(CNCC3)N)C2)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 GNXOXGZXNPZHGK-UHFFFAOYSA-N 0.000 claims 1
- AGPNGVLMDLSZJZ-UHFFFAOYSA-N 7-(5-amino-2-methylpiperidin-1-yl)-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(N2C(CCC(N)C2)C)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 AGPNGVLMDLSZJZ-UHFFFAOYSA-N 0.000 claims 1
- JIUAJJKGVHHMAV-UHFFFAOYSA-N 7-(6-amino-4-azaspiro[2.5]octan-2-yl)-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(C2C3(NCC(N)CC3)C2)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 JIUAJJKGVHHMAV-UHFFFAOYSA-N 0.000 claims 1
- VLXPXJGCUSCJBX-UHFFFAOYSA-N 7-(7-amino-5-azaspiro[2.5]octan-2-yl)-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(C2C3(CC(N)CNC3)C2)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 VLXPXJGCUSCJBX-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- VBYIVPZYCNKFFD-UHFFFAOYSA-N n-fluorohydroxylamine Chemical compound ONF VBYIVPZYCNKFFD-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 82
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 77
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 41
- 239000002904 solvent Substances 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 125000004432 carbon atom Chemical group C* 0.000 description 34
- 239000000047 product Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
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- 150000007660 quinolones Chemical class 0.000 description 15
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
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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 6
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Classifications
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- 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
-
- 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
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5889197P | 1997-09-15 | 1997-09-15 | |
US13985998A | 1998-08-25 | 1998-08-25 | |
PCT/US1998/019138 WO1999014214A1 (en) | 1997-09-15 | 1998-09-15 | Antimicrobial quinolones, their compositions and uses |
Publications (3)
Publication Number | Publication Date |
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NO20001340D0 NO20001340D0 (no) | 2000-03-15 |
NO20001340L NO20001340L (no) | 2000-05-15 |
NO323563B1 true NO323563B1 (no) | 2007-06-11 |
Family
ID=26738133
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO20001340A NO323563B1 (no) | 1997-09-15 | 2000-03-15 | Heterocykliske quinolonforbindelser med antibakteriell effekt, farmasoytisk sammensetning omfattende slike samt anvendelse av slike forbindelser for fremstilling av antimikrobielle medikamenter |
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EP (1) | EP1015445B1 (da) |
JP (1) | JP4669607B2 (da) |
KR (1) | KR100423778B1 (da) |
CN (1) | CN1264837C (da) |
AR (1) | AR013493A1 (da) |
AT (1) | ATE423776T1 (da) |
AU (1) | AU735186B2 (da) |
BR (1) | BR9812644B1 (da) |
CA (1) | CA2303389C (da) |
CO (1) | CO4970702A1 (da) |
CY (1) | CY1110255T1 (da) |
CZ (1) | CZ299554B6 (da) |
DE (1) | DE69840599D1 (da) |
DK (1) | DK1015445T3 (da) |
ES (1) | ES2321042T3 (da) |
HK (1) | HK1030415A1 (da) |
HU (1) | HUP0100051A3 (da) |
ID (1) | ID24703A (da) |
IL (2) | IL135036A0 (da) |
MY (1) | MY138335A (da) |
NO (1) | NO323563B1 (da) |
NZ (1) | NZ503740A (da) |
PE (1) | PE128799A1 (da) |
PL (1) | PL339408A1 (da) |
PT (1) | PT1015445E (da) |
RU (1) | RU2193558C2 (da) |
SA (1) | SA99191136B1 (da) |
SK (1) | SK286420B6 (da) |
TR (2) | TR200001435T2 (da) |
WO (1) | WO1999014214A1 (da) |
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- 1998-09-15 CA CA002303389A patent/CA2303389C/en not_active Expired - Lifetime
- 1998-09-15 SK SK381-2000A patent/SK286420B6/sk not_active IP Right Cessation
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1999
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2005
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