HRP20100384T1 - Antibakterijski derivati kvinolina - Google Patents
Antibakterijski derivati kvinolina Download PDFInfo
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- HRP20100384T1 HRP20100384T1 HR20100384T HRP20100384T HRP20100384T1 HR P20100384 T1 HRP20100384 T1 HR P20100384T1 HR 20100384 T HR20100384 T HR 20100384T HR P20100384 T HRP20100384 T HR P20100384T HR P20100384 T1 HRP20100384 T1 HR P20100384T1
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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 57
- 125000000217 alkyl group Chemical group 0.000 claims abstract 36
- 150000001875 compounds Chemical class 0.000 claims abstract 30
- 125000003118 aryl group Chemical group 0.000 claims abstract 25
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 18
- 125000001424 substituent group Chemical group 0.000 claims abstract 18
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 15
- 239000001257 hydrogen Substances 0.000 claims abstract 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 11
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 10
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 8
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract 6
- 125000003226 pyrazolyl 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims abstract 5
- 125000001422 pyrrolinyl group Chemical group 0.000 claims abstract 5
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000004306 triazinyl group Chemical group 0.000 claims abstract 5
- 125000001425 triazolyl group Chemical group 0.000 claims abstract 5
- 125000003386 piperidinyl 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
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract 3
- 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
- 125000005843 halogen group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 3
- 241000894006 Bacteria Species 0.000 claims 2
- 241000191967 Staphylococcus aureus Species 0.000 claims 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 241000192125 Firmicutes Species 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
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 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
- 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 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
- 125000001475 halogen functional group Chemical group 0.000 abstract 4
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 abstract 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
- C07D215/20—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
-
- 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
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/465—Nicotine; Derivatives thereof
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Abstract
Spoj formule (Ia) ili (Ib) uključujući sve stereokemijske izomerne oblike, naznačen time da jep cijeli broj koji je jednak 1, 2, 3 ili 4; q cijeli broj koji je jednak nula, 1, 2, 3 ili 4; R1 je vodik, cijano, formil, karboksil, halo, alkil, C2-6alkenil, C2-6alkinil, haloalkil, hidroksi, alkiloksi, alkltio, 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, pirolidin ili radikal formule gdje je Y 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 su - svaki nezavisno - vodik; alkil; alkiloksialkil; arilalkil; Het-alkil.; mono- ili dialkilaminoalkil; biciklo[2.2.1]heptil; Het; aril; ili -C(=Nm-NH2; ili R4 i R5 zajedno sa atomom dušika na koji su vezani oblikuju radikal odabran između: pirolidina, piperidina, piperazina, morfolina, 4-tiomorfolina, 1,1-dioksid-tiomorfolinila, azetidinila, 2,3-dihidroizoindol-1-ila, tiazolidin-3-ila, 1,2,3,6- tetrahidropiridila, heksahidro-1H-azepinila, heksahidro-1H-1,4-diazepinila, heksahidro-1,4-oksazepinila, 1,2,3,4-tetrahidroizokvinolin-2-ila, 2,5-diazabiciklo[2.2.1]heptila, pirolinila, pirolila, imidazolidinila, pirazolidinila, 2-imidazolinila, 2-pirazolinila, imidazolila, pirazolila, triazolila, piridinila, piridazinila, pirimidinila, pirazinila i triazinila, gdje je svaki radikal po izboru supstituiran sa 1, 2, 3 ili 4 supstituenta, svaki supstituent je nezavisno izabran između: alkila, haloalkila, alkilkarbonila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, aminoalkila, mono- ili dialkilaminoalkila, alkiltio, alkiltioalkila, arila, piridila, pirimidinila, piperidinila po izboru supstituiranog sa alkilom ili pirolidinila po izboru supstituiranog arilalkilom; R4a i R5a zajedno sa atomom dušika za koji su vezani tvore radikal između slijedećih: pirolidina, piperidina, piperazina, morfolina, 4-tiomorfolina, 2,3-dihidroizoindol-1-ila, tiazolidin-3-ila, 1,2,3,6-tetrahidropiridila, heksahidro-1H-azepinila, heksahidro-1H-1,4-diazepinila, heksahidro-1,4-oksazepinila, 1,2,3,4-tetrahidroizokvinolin-2-ila, pirolinila, pirolila, imidazolidinila, pirazolidinila, 2-imidazolinila, 2-pirazolinila, imidazolila, pirazolila, triazolila, piridinila, piridazinila, pirimidinila, pirazinila i triazinila, a gdje je svaki radikal po izboru supstituiran sa 1, 2, 3 ili 4 supstituenta, svaki supstituent je nezavisno izabran između: 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; iliR8
Claims (24)
1. Spoj formule (Ia) ili (Ib)
[image]
[image]
uključujući sve stereokemijske izomerne oblike, naznačen time da je
p cijeli broj koji je jednak 1, 2, 3 ili 4;
q cijeli broj koji je jednak nula, 1, 2, 3 ili 4;
R1 je vodik, cijano, formil, karboksil, halo, alkil, C2-6alkenil, C2-6alkinil, haloalkil, hidroksi, alkiloksi, alkltio, 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, pirolidin ili radikal formule
[image]
gdje je Y 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 su - svaki nezavisno - vodik; alkil; alkiloksialkil; arilalkil; Het-alkil.; mono- ili dialkilaminoalkil; biciklo[2.2.1]heptil; Het; aril; ili -C(=Nm-NH2; ili
R4 i R5 zajedno sa atomom dušika na koji su vezani oblikuju radikal odabran između: pirolidina, piperidina, piperazina, morfolina, 4-tiomorfolina, 1,1-dioksid-tiomorfolinila, azetidinila, 2,3-dihidroizoindol-1-ila, tiazolidin-3-ila, 1,2,3,6- tetrahidropiridila, heksahidro-1H-azepinila, heksahidro-1H-1,4-diazepinila, heksahidro-1,4-oksazepinila, 1,2,3,4-tetrahidroizokvinolin-2-ila, 2,5-diazabiciklo[2.2.1]heptila, pirolinila, pirolila, imidazolidinila, pirazolidinila, 2-imidazolinila, 2-pirazolinila, imidazolila, pirazolila, triazolila, piridinila, piridazinila, pirimidinila, pirazinila i triazinila, gdje je svaki radikal po izboru supstituiran sa 1, 2, 3 ili 4 supstituenta, svaki supstituent je nezavisno izabran između: alkila, haloalkila, alkilkarbonila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, aminoalkila, mono- ili dialkilaminoalkila, alkiltio, alkiltioalkila, arila, piridila, pirimidinila, piperidinila po izboru supstituiranog sa alkilom ili pirolidinila po izboru supstituiranog arilalkilom;
R4a i R5a zajedno sa atomom dušika za koji su vezani tvore radikal između slijedećih: pirolidina, piperidina, piperazina, morfolina, 4-tiomorfolina, 2,3-dihidroizoindol-1-ila, tiazolidin-3-ila, 1,2,3,6-tetrahidropiridila, heksahidro-1H-azepinila, heksahidro-1H-1,4-diazepinila, heksahidro-1,4-oksazepinila, 1,2,3,4-tetrahidroizokvinolin-2-ila, pirolinila, pirolila, imidazolidinila, pirazolidinila, 2-imidazolinila, 2-pirazolinila, imidazolila, pirazolila, triazolila, piridinila, piridazinila, pirimidinila, pirazinila i triazinila, a gdje je svaki radikal po izboru supstituiran sa 1, 2, 3 ili 4 supstituenta, svaki supstituent je nezavisno izabran između: 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=;
R10 je vodik, C1-6alkil ili arilC1-6alkil;
R11 je vodik ili alkil;
Z je S ili NR10;
aril je homociklični spoj izabran između: fenila, naftila, acenaftila ili tetrahidronaftila, gdje je svaki po izboru supstituiran sa 1, 2 ili 3 supstituenta, svaki supstituent je nezavisno izabran između: hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkila, C2-6alkenila po izboru supstituiranog sa: fenilom, haloalkilom, alkiloksi, haloalkiloksi, karboksilom, alkiloksikarbonilom, aminokarbonilom, morfolinilom ili mono- ili dialkilaminokarbonilom;
aril1 je homociklični spoj izabran između: fenila, naftila, acenaftila ili tetrahidronaftila, gdje je svaki po izboru supstituiran sa 1, 2 ili 3 supstituenta, svaki supstituent je nezavisno izabran između: hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkila, haloalkila, alkiloksi, alkiltio, haloalkiloksi, karboksila, alkiloksikarbonila, aminokarbonila, morfolinila, Het ili mono- ili dialkilaminokarbonila;
Het je monociklično heterociklični spoj izabran između: N-fenoksipiperidinila, piperidinila, pirolila, pirazolila, imidazolila, furanila, tienila, oksazolila, izoksazolila, tiazolila, izotiazolila, piridinila, pirimidinila, pirazinila ili piridazinila; odnosno biciklični heterociklični spoj izabran između: kvinolinila, kvinoksalinila, indolila, benzimidazolila, benzoksazolila, benzizoksazolila, benzotiazolila, benziotiazolila, benzofuranila, benzotienila, 2,3-dihidrobenzo[1,4]dioksinila ili benzo[1,3]dioksolila; gdje je svaki monociklični i biciklični heterociklični spoj po izboru supstituiran sa 1, 2 ili 3 supstituenta, svaki supstituent je nezavisno odabran između: halo, hidroksi, alkil ili alkiloksi;
njihovi N-oksidi, farmaceutski prihvatljive soli ili solvati.
2. Spoj prema zahtjevu 1, naznačen time da je
R3 je alkil, arilalkil, aril-O-alkil, aril-alkil-O-alkil, aril, 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 za koji su vezani tvore radikal između: pirolidina, piperidina, piperazina, morfolina, 4-tiomorfolina, 2,3-dihidroizoindol-1-ila, tiazolidin-3-ila, 1,2,3,6-tetrahidropiridila, heksahidro-1H-azepinila, heksahidro-1H-1,4-diazepinila, heksahidro-1,4-oksazepinila, 1,2,3,4- tetrahidroizokvinolin-2-il, 2,5-diazabiciklo[2.2.1]heptila, pirolinila, pirolila, imidazolidinila, pirazolidinila, 2-imidazolinila, 2-pirazolinila, imidazolila, pirazolila, triazolila, piridinila, piridazinila, pirimidinila, pirazinila i triazinila, svaki radikal po izboru je supstituiran sa 1, 2, 3 ili 4 supstituenta, svaki supstituent nezavisno je izabran između: alkila, haloalkila, alkilkarbonila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiltioalkila, arila, piridila, pirimidinila, piperidinila ili pirolidinila po izboru supstituiran sa arilalkilom;
aril je homociklični spoj izabran između: fenila, naftila, acenaftila ili tetrahidronaftila, gdje je svaki po izboru supstituiran sa 1, 2 ili 3 supstituenta, svaki supstituent je nezavisno izabran između: 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 je R1 halo.
5. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da je p jednako 1.
6. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da je R2 C1-6alkiloksi.
7. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da je R3 aril.
8. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da je q jednako 1 ili 2.
9. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da R4 i R5 predstavljaju C1-6alkil ili gdje su R4 i R5 zajedno sa atomom dušika za koji su vezani i tvore radikal izabran između piperidina ili piperazina, svaki od navedenih prstenova po izboru je supstituiran sa C1-6alkilom.
10. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da je R6 aril.
11. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da je R7 vodik.
12. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da je spoj, spoj formule (Ia).
13. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da je Z jednako S.
14. Spoj prema bilo kojem od prethodnih zahtjeva od 1 do 12 naznačen time da je Z jednako NR10.
15. Spoj prema zahtjevu 1 naznačen time da je R1 halo; R2 je C1-6alkiloksil; R3 je aril; R4 i R5 su C1-4alkil; ili R4 i R5 zajedno sa atomom dušika za koji su vezani i tvore radikal izabran između piperidina ili piperazina, svaki od navedenih prstenova po izboru je supstituiran sa C1-6alkilom;
R6 je aril;
R7 je vodik;
q je 1 ili 2;
p je 1;
R10 je C1-6alkil ili benzil.
16. Spoj prema zahtjevu 15 naznačen time da je R1 brom; R2 je metiloksi; R3 je fenil; R4 i R5 su metil ili etil; ili R4 i R5 zajedno sa atomom dušika za koji su vezani i tvore radikal izabran između piperidina ili piperazina, svaki od navedenih prstenova po izboru je supstituiran sa C1-6alkilom; R6 je fenil.
17. Spoj prema bilo kojem od prethodnih zahtjeva naznačen time da je za upotrebu u medicini.
18. Spoj prema bilo kojem od zahtjeva 1 do 16 naznačen time da je za upotrebu u medicini za liječenje bakterijske infekcije.
19. Farmaceutski pripravak koji uključuje farmaceutski prihvatljiv nosač i, kao aktivnu tvar, terapeutski djelotvornu količinu spoja kako je definirano u bilo kojem od zahtjeva 1 do 16.
20. Spoj prema zahtjevu 18 naznačen time da je bakterijska infekcija infekcija gram-pozitivnim bakterijama.
21. Spoj prema zahtjevu 20 naznačen time da je gram-pozitivna bakterija Streptococcus pneumoniae ili Staphylococcus aureus.
22. Kombinacija (a) spoja prema bilo kojem od zahtjeva 1 do 16, i (b) jednog ili više drugih antibakterijskih sredstava.
23. Proizvod naznačen time da sadrži (a) spoj prema bilo kojem od zahtjeva 1 do 16, i (b) jedno ili više drugih antibakterijskih sredstava, kao kombinirani pripravak za istovremenu, odvojenu ili sekvencijalnu upotrebu pri liječenju bakterijske infekcije.
24. Spoj prema zahtjevu 21 naznačen time da je gram-pozitivna bakterija meticilin rezistentna Staphylococcus aureus.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06125521 | 2006-12-06 | ||
| PCT/EP2007/063315 WO2008068269A1 (en) | 2006-12-06 | 2007-12-04 | Antibacterial quinoline derivatives |
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| HRP20100384T1 true HRP20100384T1 (hr) | 2010-08-31 |
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| JP (1) | JP5356245B2 (hr) |
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| ES2576491T3 (es) | 2012-04-27 | 2016-07-07 | Janssen Pharmaceutica, N.V. | Derivados de quinolina antibacterianos |
| CN104650054B (zh) * | 2013-11-25 | 2019-09-13 | 重庆医药工业研究院有限责任公司 | 一种抗结核菌的喹啉噻吩芳氧乙胺衍生物 |
| 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 |
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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 |
| MXPA04000968A (es) * | 2001-07-31 | 2005-02-17 | Univ Wayne State | Derivados de quinolina y uso de los mismos como agentes antitumor. |
| 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 |
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