HRP20160585T1 - Antibakterijski derivati kinolina - Google Patents
Antibakterijski derivati kinolina Download PDFInfo
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- HRP20160585T1 HRP20160585T1 HRP20160585TT HRP20160585T HRP20160585T1 HR P20160585 T1 HRP20160585 T1 HR P20160585T1 HR P20160585T T HRP20160585T T HR P20160585TT HR P20160585 T HRP20160585 T HR P20160585T HR P20160585 T1 HRP20160585 T1 HR P20160585T1
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- Prior art keywords
- 6alkyl
- alkyl
- mono
- amino
- compound according
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- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims 3
- 230000000844 anti-bacterial effect Effects 0.000 title 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- -1 -C=N-OR11 Chemical group 0.000 claims 45
- 150000001875 compounds Chemical class 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000001475 halogen functional group Chemical group 0.000 claims 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 6
- 125000002883 imidazolyl group Chemical group 0.000 claims 6
- 125000002757 morpholinyl group Chemical group 0.000 claims 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 4
- 125000004306 triazinyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- 241000894006 Bacteria Species 0.000 claims 3
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims 2
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 claims 2
- 241000191967 Staphylococcus aureus Species 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000005984 hexahydro-1H-1,4-diazepinyl group Chemical group 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl 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
- 201000005010 Streptococcus pneumonia Diseases 0.000 claims 1
- 241000193998 Streptococcus pneumoniae Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005094 alkyl carbonyl amino alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 229960003085 meticillin Drugs 0.000 claims 1
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 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
- C07D215/12—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
- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
-
- 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
- C07D215/38—Nitrogen atoms
-
- 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
-
- 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
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Claims (25)
1. Spoj s formulom (Ia) ili (Ib)
[image]
[image]
uključujući njegov bilo koji stereokemijski izomerni oblik, naznačen time da
q je cijeli broj jednak nula, 1, 2, 3 ili 4;
p je cijeli broj jednak 1, 2, 3 ili 4;
R1 je alkenil, alkinil, -C=N-OR11, amino, mono ili di(alkil)amino, aminoalkil, mono ili di(alkil)aminoalkil, alkilkarbonilaminoalkil, aminokarbonil, mono ili di(alkil)aminokarbonil, arilkarbonil, R5aR4aNalkil, R5aR4aN-, R5aR4aN-C(=O)-;
R2 je vodik, alkiloksi, aril, ariloksi, hidroksi, merkapto, alkiloksialkiloksi, alkiltio, mono ili di(alkil)amino, pirolidino ili radikal s formulom
[image]
u kojoj Y je CH2, O, S, NH ili N-alkil;
R3 je alkil, arilalkil, aril-O-alkil, aril-alkil-O-alkil, aril, Het, Het-alkil, Het-O-alkil, Het-alkil-O-alkil ili
[image]
fenil;
R4 i R5 svaki neovisno su vodik, alkil ili benzil; ili
R4 i R5 zajedno i uključujući N na koji su oni vezani mogu tvoriti radikal koji je odabran iz skupine koju čine pirolidinil, 2-pirolinil, 3-pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil, triazolil, piperidinil, piridinil, piperazinil, imidazolidinil, piridazinil, pirimidinil, pirazinil, triazinil, morfolinil i tiomorfolinil, svaki radikal je proizvoljno supstituiran s alkil, halo, haloalkil, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiloksialkil, alkiltioalkil i pirimidinil;
R4a i R5a zajedno s atomom dušika na koji su vezani tvore radikal odabran iz skupine koju čine 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, svaki radikal je proizvoljno supstituiran s 1, 2, 3 ili 4 supstituenata, svaki supstituent je neovisno odabran od alkila, haloalkila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiltioalkila, arila, piridila ili pirimidinila;
R6 je aril1 ili Het;
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 odabran od fenila, naftila, acenaftila ili tetrahidronaftila, koji je svaki proizvoljno supstituiran s 1, 2 ili 3 supstituenata, gdje je svaki supstituent neovisno odabran iz skupa koji čine hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkil, haloalkil, alkiloksi, haloalkiloksi, karboksil, alkiloksikarbonil, aminokarbonil, morfolinil ili mono- ili dialkilaminokarbonil;
aril1 je homocikal odabran iz skupa koji čine fenil, naftil, acenaftil ili tetrahidronaftil, koji je svaki proizvoljno supstituiran s 1, 2 ili 3 supstituenata, gdje je svaki supstituent neovisno odabran od hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkila, haloalkila, alkiloksi, alkiltio, haloalkiloksi, karboksila, alkiloksikarbonila, aminokarbonila, morfolinila, Het ili mono- ili dialkilaminokarbonila;
Het je monociklički heterocikal odabran iz skupa koji čine N-fenoksipiperidinil, piperidinil, pirolil, pirazolil, imidazolil, furanil, tienil, oksazolil, izoksazolil, tiazolil, izotiazolil, piridinil, pirimidinil, pirazinil ili piridazinil; ili biciklički heterocikal odabran od kinolinila, kinoksalinila, indolila, benzimidazolila, benzoksazolila, benzizoksazolila, benzotiazolila, benzizotiazolila, benzofuranila, benzotienila, 2,3-dihidrobenzo[1,4]dioksinila ili benzo[1,3]dioksolila; svaki monociklički i biciklički heterocikal je proizvoljno supstituiran sa 1, 2 ili 3 supstituenata, te je svaki supstituent neovisno 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
R1 je C2-6alkenil, C2-6alkinil, -C=N-OR11, amino, mono ili di(C1-6alkil)amino, aminoC1-6alkil, mono ili di(C1-6alkil)aminoC1-6alkil, C1-6alkilkarbonilaminoC1-6alkil, aminokarbonil, mono ili di(C1-6alkil)aminokarbonil, arilkarbonil, R5aR4aNalkil, R5aR4aN-, R5aR4aN-C(=O)-;
R2 je vodik, C1-6alkiloksi, aril, ariloksi, hidroksi, merkapto, C1-6alkiloksiC1-6alkiloksi, C1-6alkiltio, mono ili di(C1-6alkil)amino, pirolidino ili radikal s formulom
[image]
pri čemu Y je CH2, O, S, NH ili N-C1-6alkil;
R3 je C1-6alkil, C3-6cikloalkil, arilC1-6alkil, aril-O-C1-6alkil, arilC1-6alkil-O-C1-6alkil, aril, Het, Het-C1-6alkil, Het-O-C1-6alkil ili HetC1-6alkil-O-C1-6alkil, ili
[image]
fenil;
R4 i R5 svaki neovisno su vodik, C1-6alkil ili benzil; ili
R4 i R5 zajedno i uključujući N na koji su oni vezani mogu tvoriti radikal koji je odabran iz skupine koju čine pirolidinil, 2-pirolinil, 3-pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil, triazolil, piperidinil, piridinil, piperazinil, imidazolidinil, piridazinil, pirimidinil, pirazinil, triazinil, morfolinil i tiomorfolinil, svaki radikal je proizvoljno supstituiran s C1-6alkilom, halo, haloC1-6alkilom, hidroksi, C1-6alkiloksi, amino, mono- ili di(C1-6alkil)amino, C1-6alkiltio, C1-6alkiloksiC1-6alkilom, C1-6alkiltioC1-6alkilom i pirimidinilom;
R4a i R5a zajedno s atomom dušika na koji su vezani tvore radikal odabran iz skupine koju čine 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, svaki radikal je proizvoljno supstituiran s 1, 2, 3 ili 4 supstituenata, svaki supstituent je neovisno odabran iz skupa koji čine C1-6alkil, polihaloC1-6alkil, halo, arilC1-6alkil, hidroksi, C1-6alkiloksi, C1-6alkiloksiC1-6alkil, amino, mono- ili di(C1-6alkil)amino3, C1-6alkiltio, C1-6alkiloksiC1-6alkil, C1-6alkiltioC1-6alkil, aril, piridil ili pirimidinil;
R6 je aril1 ili Het;
R7 je vodik, halo, C1-6alkil, aril ili Het;
R8 je vodik ili C1-6alkil;
R9 je oksi; ili
R8 i R9 zajedno tvore radikal -CH=CH-N=;
R11 je vodik ili C1-6alkil;
aril je homocikal odabran od fenila, naftila, acenaftila ili tetrahidronaftila, koji je svaki proizvoljno supstituiran s 1, 2 ili 3 supstituenata, gdje je svaki supstituent neovisno odabran od hidroksi, halo, cijano, nitro, amino, mono- ili di(C1-6alkil)amino C1-6alkila, polihaloC1-6alkila, C1-6alkiloksi, haloC1-6alkiloksi, karboksila, C1-6alkiloksikarbonila, aminokarbonila, morfolinila ili mono- ili di(C1-6alkil)aminokarbonila;
aril1 je homocikal odabran od fenila, naftila, acenaftila ili tetrahidronaftila, koji je svaki proizvoljno supstituiran s 1, 2 ili 3 supstituenata, gdje je svaki supstituent neovisno odabran od hidroksi, halo, cijano, nitro, amino, mono- ili di(C1-6alkil)amino, C1-6alkila, polihaloC1-6alkila, C1-6alkiloksi, C1-6alkiltio, haloC1-6alkiloksi, karboksila, C1-6alkiloksikarbonila, aminokarbonila, morfolinila, Het ili mono- ili di(C1-6alkil)aminokarbonila;
Het je monociklički heterocikal odabran iz skupa koji sadrži N-fenoksipiperidinil piperidinil, pirolil, pirazolil, imidazolil, furanil, tienil, oksazolil, izoksazolil, tiazolil, izotiazolil, piridinil, pirimidinil, pirazinil ili piridazinil; ili biciklički heterocikal odabran od kinolinila, kinoksalinila, indolila, benzimidazolila, benzoksazolila, benzizoksazolila, benzotiazolila, benzizotiazolila, benzofuranila, benzotienila, 2,3-dihidrobenzo[1,4]dioksinila ili benzo[1,3]dioksolila; svaki monociklički i biciklički heterocikal je proizvoljno supstituiran sa 1, 2 ili 3 supstituenata, svaki supstituent je neovisno odabran od halo, hidroksi, C1-6alkila ili C1-6alkiloksi.
3. Spoj prema zahtjevu 1 ili 2 naznačen time da R1 je C2-6alkenil, C2-6alkinil, -C=N-OR11, amino, mono ili di(C1-6alkil)amino, aminoC1-6alkil, mono ili di(C1-6alkil)aminoC1-6alkil, C1-6alkilkarbonilaminoC1-6alkil, aminokarbonil, mono ili di(C1-6alkil)aminokarbonil, R5aR4aNalkil, R5aR4aN-, R5aR4aN-C(=O)-.
4. Spoj prema zahtjevu 3 naznačen time da R1 je C2-6alkenil, C2-6alkinil, -C=N-OR11, R5aR4Nalkil, R5aR4aN- ili R5aR4a-C(=O)-,
5. Spoj prema zahtjevu 4 naznačen time da R1 je C2-6alkenil ili -C=N-OR11.
6. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da p je jednak 1.
7. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da R2 je C1-6alkiloksi.
8. Spoj prema zahtjevu 7 naznačen time da R2 je metiloksi.
9. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da R3 je arilC1-6alkil ili aril.
10. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da q je jednak 1 ili 3.
11. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da R4 i R5 predstavljaju C1-6alkil ili pri čemu R4 i R5 su uzeti zajedno s atomom dušika na koji su vezani i tvore piperidino.
12. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da R6 je fenil proizvoljno supstituiran s halo.
13. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da R7 je vodik.
14. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da spoj je spoj s formulom (Ia).
15. Spoj prema zahtjevu 1 naznačen time da spoj je spoj s formulom (Ia) i pri čemu R1 je C2-6alkenil, C2-6alkinil, -C=N-OR11, amino, aminoC1-6alkil, mono ili di(C1-6alkil)aminoC1-6alkil, C1-6alkilkarbonilaminoC1-6alkil, mono ili di(C1-6alkil)aminokarbonil, arilkarbonil, R5aR4aNalkil, R5aR4aN-, R5aR4aN-C(=O)-; R2 je alkiloksi; R3 je arilalkil ili aril; R4 i R5 su C1-6alkil; ili R4 i R5 zajedno s atomom dušika na koji su vezani tvore piperidino; R6 je fenil, proizvoljno supstituiran s halo; R7 je vodik; R11 je vodik ili C1-6alkil; q je 1 ili 3; p je 1.
16. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da je za uporabu kao lijek.
17. Spoj prema bilo kojem od zahtjeva 1 do 15 naznačen time da je za uporabu kao lijek za liječenje bakterijske infekcije koja obuhvaća mikobakterijsku infekciju.
18. Farmaceutski pripravak naznačen time da sadrži farmaceutski prihvatljiv nosač, te kao aktivan sastojak, terapeutski učinkovitu količinu spoja kako je definirano u bilo kojem od zahtjeva 1 do 15.
19. Spoj za uporabu prema zahtjevu 17 naznačen time da bakterijska infekcija je infekcija s gram-pozitivnom bakterijom.
20. Spoj za uporabu prema zahtjevu 19 naznačen time da gram-pozitivna bakterija je Streptococcus pneumonia ili Staphilococcus aureus.
21. Spoj s formulom
[image]
naznačen time da W2 predstavlja prikladnu odlazeću skupinu i pri čemu su varijable definirane kao u zahtjevu 1.
22. Spoj s formulom
[image]
naznačen time da W2 predstavlja prikladnu odlazeću skupinu i pri čemu su varijable definirane kao u zahtjevu 1.
23. Kombinacija naznačena time da sadrži (a) spoj prema bilo kojem od zahtjeva 1 do 15, i (b) jedno ili više drugih antibakterijskih sredstava.
24. Proizvod koji sadrži (a) spoj prema bilo kojem od zahtjeva 1 do 15, i (b) jedno ili više drugih antibakterijskih sredstava, naznačen time da se koristi kao kombinirani pripravak za istovremenu, odvojenu ili uzastopnu upotrebu za liječenje bakterijske infekcije.
25. Spoj prema zahtjevu 20 naznačen time da gram-pozitivna bakterija je bakterija Staphilococcus aureus otporna na meticilin.
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| EP06125499 | 2006-12-06 | ||
| PCT/EP2007/063313 WO2008068267A1 (en) | 2006-12-06 | 2007-12-04 | Antibacterial quinoline derivatives |
| EP07847811.2A EP2099758B1 (en) | 2006-12-06 | 2007-12-04 | Antibacterial quinoline derivatives |
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| EP (1) | EP2099758B1 (hr) |
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| ES2576491T3 (es) | 2012-04-27 | 2016-07-07 | Janssen Pharmaceutica, N.V. | Derivados de quinolina antibacterianos |
| EA038350B1 (ru) | 2012-04-27 | 2021-08-12 | Янссен Фармацевтика Нв | Антибактериальные хинолиновые производные |
| ES2628365T3 (es) | 2012-10-16 | 2017-08-02 | Janssen Pharmaceutica N.V. | Moduladores de quinolinilo unidos a fenilo de ROR-GAMA-T |
| MX358508B (es) | 2012-10-16 | 2018-08-22 | Janssen Pharmaceutica Nv | Moduladores de quinolinilo unidos a metileno de receptor nuclear de acido retinoico-gamma-t. |
| US9303015B2 (en) | 2012-10-16 | 2016-04-05 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORγt |
| US9328095B2 (en) | 2013-10-15 | 2016-05-03 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORgammat |
| EP3057421B1 (en) | 2013-10-15 | 2019-11-20 | Janssen Pharmaceutica NV | Alkyl linked quinolinyl modulators of ror(gamma)t |
| CA2927182A1 (en) | 2013-10-15 | 2015-04-23 | Janssen Pharmaceutica Nv | Quinolinyl modulators of ror.gamma.t |
| US9403816B2 (en) | 2013-10-15 | 2016-08-02 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of RORγt |
| US9284308B2 (en) | 2013-10-15 | 2016-03-15 | Janssen Pharmaceutica Nv | Methylene linked quinolinyl modulators of RORγt |
| US9221804B2 (en) | 2013-10-15 | 2015-12-29 | Janssen Pharmaceutica Nv | Secondary alcohol quinolinyl modulators of RORγt |
| US10555941B2 (en) | 2013-10-15 | 2020-02-11 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
| BR112017000764B1 (pt) * | 2014-07-14 | 2022-07-12 | Shanghai Jia Tan Pharmatech Co. Ltd. | Composto, método para preparar o composto e uso do composto |
| CN105330595B (zh) * | 2014-07-14 | 2019-12-10 | 上海嘉坦医药科技有限公司 | 吡啶衍生物及其作为抗分支杆菌的应用 |
| AU2016212116B2 (en) * | 2015-01-27 | 2021-07-15 | Janssen Pharmaceutica Nv | Dispersible compositions |
| WO2017121323A1 (zh) * | 2016-01-13 | 2017-07-20 | 辰欣药业股份有限公司 | 一种吡啶衍生物类化合物的制备方法及其中间体和晶型 |
| CN105601566A (zh) * | 2016-02-02 | 2016-05-25 | 张敏 | 一种护理烧伤后感染的药物组合物 |
| US10508097B2 (en) * | 2016-03-07 | 2019-12-17 | The Global Alliance For Tb Drug Development, Inc. | Antibacterial compounds and uses thereof |
| US11857352B2 (en) | 2016-09-06 | 2024-01-02 | The Research Foundation For The State University Of New York | Positron imaging tomography imaging agent composition and method for bacterial infection |
| CN111757879A (zh) * | 2018-01-29 | 2020-10-09 | 卡地拉健康护理有限公司 | 用作抗菌剂的杂环化合物 |
| CA3198350A1 (en) * | 2020-10-22 | 2022-04-28 | Lunella Biotech, Inc. | Mitochondrial atp inhibitors targeting the gamma subunit prevent metastasis |
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| CA2270123A1 (en) * | 1996-10-28 | 1998-05-07 | Department Of The Army, U.S. Government | Compounds, compositions and methods for treating antibiotic-resistant infections |
| PL222801B1 (pl) * | 2002-07-25 | 2016-09-30 | Janssen Pharmaceutica Nv | Pochodne chinoliny, ich zastosowanie, sposób ich wytwarzania oraz kompozycja farmaceutyczna zawierająca je |
| AP2188A (en) | 2004-01-23 | 2010-12-14 | Janssen Pharmaceutica Nv | Substituted quinolines and their use as mycobacterial inhibitors. |
| PT1711181E (pt) | 2004-01-23 | 2009-12-29 | Janssen Pharmaceutica Nv | Derivados quinolina e sua utilização como inibidores micobacterianos |
| AU2005210036B2 (en) | 2004-01-29 | 2010-12-23 | Janssen Pharmaceutica N.V. | Quinoline derivatives for use as mycobacterial inhibitors |
| EP1753427B1 (en) | 2004-05-28 | 2008-04-02 | Janssen Pharmaceutica N.V. | Use of substituted quinoline derivatives for the treatment of drug resistant mycobacterial diseases |
| DK1797115T3 (en) | 2004-09-28 | 2017-10-02 | Janssen Pharmaceutica Nv | BACTERIAL ATP SYNTHASE BINDING DOMAIN. |
| EE05394B1 (et) | 2004-12-24 | 2011-04-15 | Janssen Pharmaceutica N.V. | Kinoliinihendid kasutamiseks latentse tuberkuloosi ravis |
| CA2528849C (en) * | 2005-06-08 | 2014-01-14 | Janssen Pharmaceutica N.V. | Quinoline derivatives as antibacterial agents |
| JO2855B1 (en) * | 2005-08-03 | 2015-03-15 | شركة جانسين فارماسوتيكا ان. في | Quinoline derivatives acting as antibacterial agents |
| JO2952B1 (en) * | 2005-08-03 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Quinoline derivatives acting as antibacterial agents |
| JO2837B1 (en) * | 2005-08-03 | 2014-09-15 | جانسن فارمسيتكا ان في | Quinoline derivatives acting as antibacterial agents |
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