HRP20110540T1 - Antibakterijski derivati kinolina - Google Patents
Antibakterijski derivati kinolina Download PDFInfo
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- HRP20110540T1 HRP20110540T1 HR20110540T HRP20110540T HRP20110540T1 HR P20110540 T1 HRP20110540 T1 HR P20110540T1 HR 20110540 T HR20110540 T HR 20110540T HR P20110540 T HRP20110540 T HR P20110540T HR P20110540 T1 HRP20110540 T1 HR P20110540T1
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- alkyl
- aryl
- mono
- het
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- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims 2
- 230000000844 anti-bacterial effect Effects 0.000 title 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- -1 cyano, formyl Chemical group 0.000 claims abstract 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract 31
- 150000001875 compounds Chemical class 0.000 claims abstract 26
- 125000003118 aryl group Chemical group 0.000 claims abstract 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 16
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 15
- 125000001424 substituent group Chemical group 0.000 claims abstract 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 13
- 239000001257 hydrogen Substances 0.000 claims abstract 13
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 10
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 9
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 9
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 6
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract 6
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims abstract 5
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract 5
- 125000005984 hexahydro-1H-1,4-diazepinyl group Chemical group 0.000 claims abstract 5
- 125000002632 imidazolidinyl group Chemical group 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract 5
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims abstract 5
- 125000001422 pyrrolinyl group Chemical group 0.000 claims abstract 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 4
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract 4
- 125000004306 triazinyl group Chemical group 0.000 claims abstract 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 3
- 125000001425 triazolyl group Chemical group 0.000 claims abstract 3
- VZLKQEPNZIWSFF-UHFFFAOYSA-N 1-pyrrolidin-1-ylpiperidine Chemical compound C1CCCN1N1CCCCC1 VZLKQEPNZIWSFF-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 2
- 125000005094 alkyl carbonyl amino alkyl group Chemical group 0.000 claims abstract 2
- 125000005418 aryl aryl group Chemical group 0.000 claims abstract 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract 2
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 2
- 125000002393 azetidinyl group Chemical group 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 241000894006 Bacteria Species 0.000 claims 2
- 241000191967 Staphylococcus aureus Species 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 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 claims 1
- 206010062207 Mycobacterial infection Diseases 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 241000193998 Streptococcus pneumoniae Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 229960003085 meticillin Drugs 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
-
- 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
- A61P31/06—Antibacterial agents for tuberculosis
-
- 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
- A61P31/08—Antibacterial agents for leprosy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Spoj, naznačen time, da je prikazan formulom (Ia) ili (Ib) uključujući i bilo koji njegov stereokemijski izomerni oblik, pri čemu p je cijeli broj koji je jednak 1, 2, 3 ili 4; q je cijeli broj koji je jednak nuli, 1, 2, 3 ili 4; R1 je vodik, cijano, formil, karboksil, halo, alkil, C2-6alkenil, C2-6alkinil, haloalkil, hidroksi, alkiloksi, alkiltio, alkiltioalkil -C=N-OR11, amino, mono ili di(alkil)amino, aminoalkil, mono ili di(alkil)aminoalkil, alkilkarbonilaminoalkil, aminokarbonil, mono ili di(alkil)aminokarbonil, arilalkil, arilkarbonil, R5aR4aNalkil, di(aril)alkil, aril, R5aR4aN-, R5aR4aN-C(=O)- ili Het; R2 je vodik, alkiloksi, aril, ariloksi, hidroksi, merkapto, alkiloksialkiloksi, alkiltio, mono ili di(alkil)amino, pirolidino ili radikal formule pri čemu Y je CH2, O, S, NH ili N-alkil; R3 je alkil, arilalkil, aril-O-alkil, aril-alkil-O-alkil, aril, aril-aril, Het, Het-alkil, Het-O-alkil, Het-alkil-O-alkil ili R4 i R5 svaki nezavisno je vodik; alkil; alkiloksialkil; arilalkil; Het-alkil; mono- ili dialkilaminoalkil; biciklo[2.2.1]heptil; Het; aril; ili -C(=NH)-NH2; iliR4 i R5 zajedno sa atomom dušika, na kojeg su vezani, tvore radikal koji je odabran iz skupine koja sadrži pirolidino, piperidin, piperazino, morfolino, 4-tiomorfolino, 1,1-dioksid-tiomorfolinil, azetidinil, 2,3-dihidroizoindol-1-il, tiazolidin-3-il, 1,2,3,6-tetrahidropiridil, heksahidro-1H-azepinil, heksahidro-1H-1,4-diazepinil, heksahidro-1,4-oksazepinil, 1,2,3,4-tetrahidroizokinolin-2-il, 2,5-diazabiciklo[2.2,1]heptil, pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil, triazolil, piridinil, piridazinil, pirimidinil, pirazinil i triazinil, te je svaki radikal proizvoljno supstituiran sa 1, 2, 3 ili 4 supstituenata, te je svaki supstituent nezavisno odabran od alkila, haloalkila, alkilkarbonila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, aminoalkila, mono- ili dialkilaminoalkila, alkiltio, alkiltioalkila, arila, piridila, pirimidinila, piperidinila koji je proizvoljno supstituiran sa alkilom ili pirolidinilom koji je proizvoljno supstituiran sa arilalkilom; R4a i R5a zajedno sa atomom dušika, na kojeg su spojeni, tvore radikal koji je odabran iz skupine koja sadrži pirolidino, piperidino, piperazino, morfolino, 4-tiomorfolino, 2,3-dihidroizoindol-1-il, tiazolidin-3-il, 1,2,3,6-tetrahidropiridil, heksahidro-1H-azepinil, heksahidro-1H-1,4-diazepinil, heksahidro-1,4-oksazepinil, 1,2,3,4-tetrahidroizokinolin-2-il, pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil triazolil, piridinil, piridazinil, pirimidinil, pirazinil i triazinil, te je svaki radikal proizvoljno supstituiran sa 1, 2, 3 ili 4 supstituenata, te je svaki supstituent nezavisno odabran od alkila, haloalkila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiltioalkila, arila, piridila ili pirimidinila; R7 je vodik, halo, alkil, aril ili Het; R8 je
Claims (21)
1. Spoj, naznačen time, da je prikazan formulom (Ia) ili (Ib)
[image]
[image]
uključujući i bilo koji njegov stereokemijski izomerni oblik, pri čemu
p je cijeli broj koji je jednak 1, 2, 3 ili 4;
q je cijeli broj koji je jednak nuli, 1, 2, 3 ili 4;
R1 je vodik, cijano, formil, karboksil, halo, alkil, C2-6alkenil, C2-6alkinil, haloalkil, hidroksi, alkiloksi, alkiltio, alkiltioalkil -C=N-OR11, amino, mono ili di(alkil)amino, aminoalkil, mono ili di(alkil)aminoalkil, alkilkarbonilaminoalkil, aminokarbonil, mono ili di(alkil)aminokarbonil, arilalkil, arilkarbonil, R5aR4aNalkil, di(aril)alkil, aril, R5aR4aN-, R5aR4aN-C(=O)- ili Het;
R2 je vodik, alkiloksi, aril, ariloksi, hidroksi, merkapto, alkiloksialkiloksi, alkiltio, mono ili di(alkil)amino, pirolidino ili radikal formule
[image]
pri čemu Y je CH2, O, S, NH ili N-alkil;
R3 je alkil, arilalkil, aril-O-alkil, aril-alkil-O-alkil, aril, aril-aril, Het, Het-alkil, Het-O-alkil, Het-alkil-O-alkil ili
[image]
R4 i R5 svaki nezavisno je vodik; alkil; alkiloksialkil; arilalkil; Het-alkil; mono- ili dialkilaminoalkil; biciklo[2.2.1]heptil; Het; aril; ili -C(=NH)-NH2; ili
R4 i R5 zajedno sa atomom dušika, na kojeg su vezani, tvore radikal koji je odabran iz skupine koja sadrži pirolidino, piperidin, piperazino, morfolino, 4-tiomorfolino, 1,1-dioksid-tiomorfolinil, azetidinil, 2,3-dihidroizoindol-1-il, tiazolidin-3-il, 1,2,3,6-tetrahidropiridil, heksahidro-1H-azepinil, heksahidro-1H-1,4-diazepinil, heksahidro-1,4-oksazepinil, 1,2,3,4-tetrahidroizokinolin-2-il, 2,5-diazabiciklo[2.2,1]heptil, pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil, triazolil, piridinil, piridazinil, pirimidinil, pirazinil i triazinil, te je svaki radikal proizvoljno supstituiran sa 1, 2, 3 ili 4 supstituenata, te je svaki supstituent nezavisno odabran od alkila, haloalkila, alkilkarbonila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, aminoalkila, mono- ili dialkilaminoalkila, alkiltio, alkiltioalkila, arila, piridila, pirimidinila, piperidinila koji je proizvoljno supstituiran sa alkilom ili pirolidinilom koji je proizvoljno supstituiran sa arilalkilom;
R4a i R5a zajedno sa atomom dušika, na kojeg su spojeni, tvore radikal koji je odabran iz skupine koja sadrži pirolidino, piperidino, piperazino, morfolino, 4-tiomorfolino, 2,3-dihidroizoindol-1-il, tiazolidin-3-il, 1,2,3,6-tetrahidropiridil, heksahidro-1H-azepinil, heksahidro-1H-1,4-diazepinil, heksahidro-1,4-oksazepinil, 1,2,3,4-tetrahidroizokinolin-2-il, pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil triazolil, piridinil, piridazinil, pirimidinil, pirazinil i triazinil, te je svaki radikal proizvoljno supstituiran sa 1, 2, 3 ili 4 supstituenata, te je svaki supstituent nezavisno odabran od alkila, haloalkila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiltioalkila, arila, piridila ili pirimidinila;
R7 je vodik, halo, alkil, aril ili Het;
R8 je vodik ili alkil;
R9 je okso; ili
R8 i R9 zajedno tvore radikal -CH=CH-N=;
R11 je vodik ili alkil;
aril je homocikal koji je odabran od fenila, naftila, acenaftila ili tetrahidronaftila, te je svaki od njih proizvoljno supstituiran sa 1, 2 ili 3 supstituenata, a svaki supstituent je nezavisno odabran od hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkila, C2-6alkenila koji je proizvoljno supstituiran sa fenilom, haloalkilom, alkiloksi, haloalkiloksi, karboksilom, alkiloksikarbonilom, aminokarbonilom, morfolinilom ili mono- ili dialkilaminokarbonilom;
Het je monociklički heterocikal koji je odabran iz N-fenoksipiperidinila, piperidinila, pirolila, pirazolila, imidazolila, furanila, tienila, oksazolila, izoksazolila, tiazolila, izotiazolila, piridinila, pirimidinila, pirazinila ili piridazinila; ili biciklički heterocikal koji je odabran od kvinolinila, kvinoksalinila, indolila, benzimidazolila, benzoksazolila, benzizoksazolila, benzotiazolila, benzizotiazolila, benzofuranila, benzotienila, 2,3-dihidrobenzo[1,4]dioksinila ili benzo[1,3]dioksolila; a svaki monociklički ili biciklički heterocikal je proizvoljno supstituiran sa 1, 2 ili 3 supstituenata, te je svaki supstituent nezavisno odabran od halo, hidroksi, alkila ili alkiloksi;
njegov N-oksid, njegova farmaceutski prihvatljiva sol ili njegov solvat.
2. Spoj prema zahtjevu 1, naznačen time, da
R3 je alkil, arilalkil, aril-O-alkil, aril-alkil-O-alkil, aril, Het, Het-alkil, Het-O-alkil, Het-alkil-O-alkil ili
[image]
R4 i R5 svaki nezavisno je vodik; alkil; alkiloksialkil; arilalkil; Het-alkil; mono- ili dialkilaminoalkil; Het; aril; ili -C(=NH)-NH2; ili
R4 i R5 zajedno sa atomom dušika, na kojeg su spojeni, tvore radikal koji je odabran iz skupine koja sadrži pirolidino, piperidino, piperazino, morfolino, 4-tiomorfolino, 2,3-dihidroizoindol-1-il, tiazolidin-3-il, 1,2,3,6-tetrahidropiridil, heksahidro-1H-azepinil, heksahidro-1H-1,4-diazepinil, heksahidro-1,4-oksazepinil, 1,2,3,4-tetrahidroizokinolin-2-il, 2,5-diazabiciklo[2.2.1]heptil, pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil, triazolil, piridinil, piridazinil, pirimidinil, pirazinil i triazinil, te je svaki radikal proizvoljno supstituiran sa 1,2, 3 ili 4 supstituenata, a svaki supstituent je nezavisno odabran od alkila, haloalkila, alkilkarbonila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiltioalkila, arila, piridila, pirimidinila, piperidinila ili pirolidinila koji je proizvoljno supstituiran sa arilalkilom;
aril je homocikal koji je odabran od fenila, naftila, acenaftila ili tetrahidronaftila, te je svaki od njih proizvoljno supstituiran sa 1, 2 ili 3 supstituenata, a svaki supstituent je nezavisno odabran od hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkila, haloalkila, alkiloksi, haloalkiloksi, karboksila, alkiloksikarbonila, aminokarbonila, morfolinila ili mono- ili dialkilaminokarbonila.
3. Spoj prema zahtjevu 1 ili 2, naznačen time, da alkil predstavlja C1-6alkil.
4. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, da R1 je halo, Het ili aril.
5. Spoj prema zahtjevu 4, naznačen time, da R1 je halo.
6. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, da je p jednako 1.
7. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, da R2 je C1-6alkiloksi.
8. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, da R3 je aril.
9. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, da je q jednako 2, 3 ili 4.
10. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, da R4 i R5 predstavljaju C1-6alkil.
11. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, da R7 je vodik.
12. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, da navedeni spoj je spoj formule (Ia).
13. Spoj prema zahtjevu 12, naznačen time, da R1 je halo; R2 je C1-6alkiloksi; R8 je aril; R4 i R5 su C1-6alkil; R7 je vodik; q je 2, 3 ili 4; te p je 1.
14. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, da se navedeni spoj upotrebljava kao lijek.
15. Spoj prema bilo kojem od zahtjeva 1 do 13, naznačen time, da se navedeni spoj upotrebljava kao lijek za liječenje bakterijske infekcije uključujući i mikobakterijsku infekciju.
16. Farmaceutski pripravak, naznačen time, da sadrži farmaceutski prihvatljivi nosač, te kao aktivan sastojak, terapeutski učinkovitu količinu spoja kako je definirano u bilo kojem od zahtjeva 1 do 13.
17. Spoj prema zahtjevu 15, naznačen time, da navedena bakterijska infekcija je infekcija sa gram-pozitivnom bakterijom.
18. Spoj prema zahtjevu 15, naznačen time, da navedena gram-pozitivna bakterija je Streptococcus pneumoniae ili Staphilococcus aureus.
19. Kombinacija, naznačena time, da sadrži (a) spoj prema bilo kojem od zahtjeva od 1 do 13 i (b) jedno ili više drugih antibakterijskih sredstava.
20. Produkt, naznačen time, da sadrži (a) spoj prema bilo kojem od zahtjeva od 1 do 13 i (b) jedno ili više drugih antibakterijskih sredstava, u obliku kombiniranog pripravka za simultanu, odvojenu ili sekvencijalnu upotrebu kod liječenja bakterijske infekcije.
21. Spoj prema zahtjevu 18, naznačen time, da je navedena gram-pozitivna bakterija Staphilococcus aureus koji je otporan na meticilin.
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EP06125529 | 2006-12-06 | ||
PCT/EP2007/063316 WO2008068270A1 (en) | 2006-12-06 | 2007-12-04 | Antibacterial quinoline derivatives |
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US (1) | US20110166179A1 (hr) |
EP (1) | EP2099759B1 (hr) |
JP (1) | JP5356246B2 (hr) |
KR (1) | KR101526175B1 (hr) |
CN (1) | CN101553471B (hr) |
AR (1) | AR064152A1 (hr) |
AT (1) | ATE509915T1 (hr) |
AU (1) | AU2007328890B2 (hr) |
BR (1) | BRPI0720133A2 (hr) |
CA (1) | CA2669829C (hr) |
CL (1) | CL2007003517A1 (hr) |
CY (1) | CY1112230T1 (hr) |
DK (1) | DK2099759T3 (hr) |
ES (1) | ES2366062T3 (hr) |
HK (1) | HK1137431A1 (hr) |
HR (1) | HRP20110540T1 (hr) |
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ME (1) | ME01245B (hr) |
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PT (1) | PT2099759E (hr) |
RS (1) | RS51848B (hr) |
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HUE041355T2 (hu) * | 2010-01-04 | 2019-05-28 | Nippon Soda Co | Nitrogén-tartalmú heterociklusos vegyület és mezõgazdasági/kertészeti csíraölõ |
AR086411A1 (es) | 2011-05-20 | 2013-12-11 | Nippon Soda Co | Compuesto heterociclico conteniendo nitrogeno y fungicida para el uso en agricultura y jardineria |
RU2486175C2 (ru) * | 2011-09-12 | 2013-06-27 | Закрытое Акционерное Общество "Фарм-Синтез" | Производные хинолина, в частности 5,6,7-замещенные 1-(2-хлорхинолин-3-ил)-4-диметиламино-2-(нафталин-1-ил)-1-фенилбутан-2-олы, способ получения и применение соединений |
DK2841425T3 (en) * | 2012-04-27 | 2016-06-27 | Janssen Pharmaceutica Nv | ANTIBACTERIAL QUINOLIN DERIVATIVES |
EA038350B1 (ru) | 2012-04-27 | 2021-08-12 | Янссен Фармацевтика Нв | Антибактериальные хинолиновые производные |
CN105232540A (zh) * | 2015-09-29 | 2016-01-13 | 王洪燕 | 一种治疗烧伤后感染的药物组合物 |
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BRPI0507065B8 (pt) * | 2004-01-23 | 2021-05-25 | Janssen Pharmaceutica Nv | derivados de quinolina, composição que os compreende, seu processo de preparação e seu uso como inibidores micobacterianos |
JO2524B1 (en) * | 2004-05-28 | 2010-03-17 | جانسن فارمسيتكا ان في | Use of substituted quinoline derivatives to treat drug-resistant microbial diseases |
EE05394B1 (et) * | 2004-12-24 | 2011-04-15 | Janssen Pharmaceutica N.V. | Kinoliinihendid kasutamiseks latentse tuberkuloosi ravis |
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