HRP20100428T1 - Antibakterijski derivati kvinolina - Google Patents
Antibakterijski derivati kvinolina Download PDFInfo
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- HRP20100428T1 HRP20100428T1 HR20100428T HRP20100428T HRP20100428T1 HR P20100428 T1 HRP20100428 T1 HR P20100428T1 HR 20100428 T HR20100428 T HR 20100428T HR P20100428 T HRP20100428 T HR P20100428T HR P20100428 T1 HRP20100428 T1 HR P20100428T1
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- alkyl
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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 69
- 125000000217 alkyl group Chemical group 0.000 claims abstract 39
- 150000001875 compounds Chemical class 0.000 claims abstract 36
- 125000003118 aryl group Chemical group 0.000 claims abstract 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 19
- 239000001257 hydrogen Substances 0.000 claims abstract 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 18
- 125000001424 substituent group Chemical group 0.000 claims abstract 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 17
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 16
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 11
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 10
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 8
- 125000005984 hexahydro-1H-1,4-diazepinyl group Chemical group 0.000 claims abstract 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 7
- 125000001425 triazolyl group Chemical group 0.000 claims abstract 7
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims abstract 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract 6
- 125000004093 cyano group Chemical group *C#N 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
- 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
- 125000004435 hydrogen atom Chemical class [H]* 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
- 125000005418 aryl aryl group Chemical group 0.000 claims abstract 4
- 125000003386 piperidinyl 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
- 125000002393 azetidinyl 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
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract 2
- 125000004104 aryloxy 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
- 150000002431 hydrogen Chemical group 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000000543 intermediate Substances 0.000 claims 5
- 239000002585 base Substances 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 241000894006 Bacteria Species 0.000 claims 3
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 125000000815 N-oxide group Chemical group 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
- 239000012453 solvate Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 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
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 206010019909 Hernia Diseases 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
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 229910006124 SOCl2 Inorganic materials 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 241000193998 Streptococcus pneumoniae Species 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000003277 amino group Chemical group 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
- 239000012458 free base 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
- 238000000034 method Methods 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
- 125000002911 monocyclic heterocycle group Chemical group 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride 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
- 230000009466 transformation Effects 0.000 claims 1
- 238000000844 transformation Methods 0.000 claims 1
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical group ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- 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
- A61K31/435—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
-
- 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
- C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon 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
- C07D215/12—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
-
- 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
- C07D215/36—Sulfur 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
- C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- 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
- C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
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- General Health & Medical Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Spoj formule (Ia) ili (Ib) uključujući njegove bilo koje stereokemijske izomerne oblike, naznačen time da Q predstavlja radikal formulep je cijeli broj jednak 1, 2, 3 ili 4; q je cijeli broj 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 R3a je vodik, cijano, alkil, arilalkil, aril-O-alkil, aril-alkil-O-alkil, aril, aril-aril, Het, Het-alkil, Het-O-alkil ili Het-alkil-O-alkil; R4 i R5 svaki nesavisno su 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 odabran iz skupine koju čine pirolidino, piperidino, 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-tetrahidroizokvinolin-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, svaki radikal po izboru je supstituiran sa 1, 2, 3 ili 4 suptituenta, svaki supstituent nazavisno odabran između alkil, haloalkil, alkilkarbonil, halo, arilalkil, hidroksi, alkiloksi, amino, mono- ili dialkilamino, aminoalkil, mono- ili dialkilaminoalkil, alkiltio, alkiltioalkil, aril, piridil, pirimidinil, piperidinil po izboru supstituirani sa alkilom ili pirolidinilom po izboru supstituiranim sa arilalkilom; R4a i R5a zajedno sa atomom dušika na kojeg su vezani tvore radikal 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-tetrahidroizokvinolin-2-il, pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil, triazolil, piridinil, piridazinil, pirimidinil, pirazinil i triazinil, svaki radikal je po izboru supstituiran sa 1, 2, 3 ili 4 suptituenta, svaki supstituent je nazavisno odabran između alkila, haloalkila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiltioalkila, ar
Claims (30)
1. Spoj formule (Ia) ili (Ib)
[image]
[image]
uključujući njegove bilo koje stereokemijske izomerne oblike, naznačen time da Q predstavlja radikal formule
[image]
p je cijeli broj jednak 1, 2, 3 ili 4;
q je cijeli broj 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]
R3a je vodik, cijano, alkil, arilalkil, aril-O-alkil, aril-alkil-O-alkil, aril, aril-aril, Het, Het-alkil, Het-O-alkil ili Het-alkil-O-alkil;
R4 i R5 svaki nesavisno su 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 odabran iz skupine koju čine pirolidino, piperidino, 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-tetrahidroizokvinolin-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, svaki radikal po izboru je supstituiran sa 1, 2, 3 ili 4 suptituenta, svaki supstituent nazavisno odabran između alkil, haloalkil, alkilkarbonil, halo, arilalkil, hidroksi, alkiloksi, amino, mono- ili dialkilamino, aminoalkil, mono- ili dialkilaminoalkil, alkiltio, alkiltioalkil, aril, piridil, pirimidinil, piperidinil po izboru supstituirani sa alkilom ili pirolidinilom po izboru supstituiranim sa arilalkilom;
R4a i R5a zajedno sa atomom dušika na kojeg su vezani tvore radikal 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-tetrahidroizokvinolin-2-il, pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil, triazolil, piridinil, piridazinil, pirimidinil, pirazinil i triazinil, svaki radikal je po izboru supstituiran sa 1, 2, 3 ili 4 suptituenta, svaki supstituent je nazavisno odabran 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═;
R11 je vodik ili alkil;
aril je homocikal odabran između fenil, naftil, acenaftil ili tetrahidronaftil, svaki po izboru je supstituiran sa 1, 2 ili 3 supstituenta, svaki supstituent nezavisno je odabran između hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkil, C2-6alkenil po izboru je supstituiran sa fenilom, haloalkilom, alkiloksi, haloalkiloksi, karboksilom, alkiloksikarbonilom, aminokarbonilom, morfolinilom ili mono- ili dialkilaminokarbonilom;
aril1 je homocikal odabran između fenil, naftil, acenaftil ili tetrahidronaftil, svaki je po izboru supstituiran sa 1, 2 ili 3 supstituenta, svaki supstituent nezavisno odabran između hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkil, haloalkil, alkiloksi, alkiltio, haloalkiloksi, karboksil, alkiloksikarbonil, aminokarbonil, morfolinil, Het ili mono- ili dialkilaminokarbonil;
Het je monociklički heterocikal odabran između N-fenoksipiperidinila, piperidinila, pirolila, pirazolila, imidazolila, furanila, tienila, oksazolila, izoksazolila, tiazolila, izotiazolila, piridinila, pirimidinila, pirazinila ili piridazinila; ili biciklički heterocikal odabran između kvinolinila, kvinoksalinila, indolila, benzimidazolila, benzoksazolila, benzizoksazolila, benzotiazolila, benzizotiazolila, benzofuranila, benzotienila, 2,3-dihidrobenzo[1,4]dioksinila ili benzo[1,3]dioksolila; svaki monociklički i biciklički heterocikal po izboru je supstituiran sa 1, 2 ili 3 supstituenta, svaki supstituent nezavisno je odabran između halo, hidroksi, alkil ili alkiloksi;
njegov N-oksid, njegova farmaceutski prihvatljiva sol ili njegov solvat.
2. Spoj prema patentnom 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]
R3a je vodik, cijano, alkil, arilalkil, aril-O-alkil, aril-alkil-O-alkil, aril, Het, Het-alkil, Het-O-alkil ili Het-alkil-O-alkil;
R4 i R5 svaki nezavisno su 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 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-tetrahidroizokvinolin-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, svaki radikal po izboru je supstituiran sa 1, 2, 3 ili 4 suptituenta, svaki je supstituent nazavisno odabran između alkil, haloalkil, alkilkarbonil, halo, arilalkil, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiltioalkil, aril, piridil, pirimidinil, piperidinil ili pirolidinil po izboru supstituiran sa arilalkilom;
aril je homocikal odabran između fenila, naftila, acenaftila ili tetrahidronaftila, svaki po izboru je supstituiran sa 1, 2 ili 3 supstituenta, svaki supstituent je nezavisno odabran između hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkila, haloalkila, alkiloksi, haloalkiloksi, karboksila, alkiloksikarbonila, aminokarbonila, morfolinila ili mono- ili dialkilaminokarbonila.
3. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time da alkil predstavlja C1-6alkil.
4. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da je R1 vodik, halo, aril, Het, C1-6alkil ili C1-6alkiloksi.
5. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da je p jednako 1.
6. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da je R2 vodik, C1-6alkiloksi ili C1-6alkiltio.
7. Spoj prema patentnom zahtjevu 6, naznačen time da je R2 metiloksi.
8. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da je R3 C1-6alkil, arilC1-6alkil, aril ili Het.
9. Spoj prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time da je R3a cijano, C1-6alkil ili arilC1-6alkil.
10. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da je q jednako 1, 2 ili 3.
11. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da R4 i R5 predstavljaju C1-6alkil ili time da R4 i R5 zajedno sa atomom dušika na kojeg su vezani tvore radikal odabran iz skupine koju čine piperidino, piperazino, morfolino, imidazolil, triazolil, svaki od navedenih prstena po izboru supstituiran sa C1-6alkil.
12. Spoj prema bilo kojem od patentnih zahtjeva 1 do 10, naznačen time da R4 i R5 zajedno sa atomom dušika na kojeg su vezani tvore radikal odabran iz skupine koju čine 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-tetrahidroizokvinolin-2-il, 2,5-diazabiciklo[2.2.1]heptil, svaki od navedenih prstena po izboru supstituiran sa C1-6alkil ili arilC1-6alkil.
13. Spoj prema patentnom zahtjevu 12, naznačen time da R4 i R5 zajedno sa atomom dušika na kojeg su vezani tvore radikal odabran iz skupine koja se sastoji od heksahidro-1H-1,4-diazepinil ili 2,5-diazabiciklo[2.2.1]heptil, svaki od navedenih prstena je po izboru supstituiran sa C1-6alkil ili arilC1-6alkil.
14. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da R6 je fenil po izboru supstituiran sa halo, cijano ili C1-6alkiloksi.
15. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da R7 je vodik.
16. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da spoj je spoj formule (Ia).
17. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da Q je radikal formule (a-1).
18. Spoj prema bilo kojem od patentnih zahtjeva 1 do 16, naznačen time da Q je radikal formule (a-2).
19. Spoj prema patentnom zahtjevu 1, naznačen time da R1 je vodik, halo, aril, Het, C1-6alkil ili C1-6alkiloksi; R2 je vodik, C1-6alkiloksi ili C1-6alkiltio; R3 je C1-6alkil, arilC1-6alkil, aril ili Het; R4 i R5 su C1-6alkil; iliR4 i R5 zajedno sa atomom dušika na kojeg su vezani tvore radikal odabran iz skupine koju čine piperidino, piperazino, morfolino, imidazolil, triazolil, heksahidro-1H-1,4-diazepinil ili 2,5-diazabiciklo[2.2.1]heptil, svaki radikal po izboru je supstituiran sa C1-6alkil ili arilC1-6alkil; R6 je fenil po izboru supstituiran sa halo, cijano ili C1-6alkiloksi; R7 je vodik; q je 1, 2 ili 3; p je 1; Q je radikal formule (a-1), (a-2) ili (a-3).
20. Spoj prema patentnom zahtjevu 1, naznačen time da je spoj odabran između
[image]
njegove farmaceutski prihvatljive soli, njegove N-oksidne forme ili njegovog solvata.
21. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da se upotrebljava kao lijek.
22. Spoj prema bilo kojem od patentnih zahtjeva 1 do 20, naznačen time da se upotrebljava kao lijek za liječenje bakterijske infekcije.
23. Farmaceutski pripravak naznačen time da sadrži farmaceutski prihvatljiv nosač i, kao aktivnu tvar, terapeutski djelotvornu količinu spoja kako je definirano u bilo kojem od patentnih zahtjeva 1 do 20.
24. Spoj prema patentnom zahtjevu 22, naznačen time da je bakterijska infekcija, infekcija sa gram-pozitivnom bakterijom.
25. Spoj prema patentnom zahtjevu 24, naznačen time da gram-pozitivna bakterija je Streptococcus pneumoniae ili Staphylococcus aureus.
26. Spoj formule
[image]
njegova farmaceutski prihvatljiva sol, njegova N-oksidna forma ili njegov solvat, naznačeni time da W1 predstavlja pogodnu odlaznu grupu i pri čemu su varijable kako je definirano u patentnom zahtjevu 1.
27. Postupak za pripremu spoja prema patentnom zahtjevu 1, naznačen time da se sastoji od:
a) reakcije intermedijera formule (II-a), (II-b), (II-c) ili (II-d) sa pogodnom kiselinom,
[image]
pri čemu R1, R2, R3, R3a, R4, R5, R6, R7, R8, R9, p i q su kako je definirano u patentnom zahtjevu 1;
b) reakcije intermedijera formule (II-a), (II-b) sa SOCl2 u prisustvu pogodnog otapala,
[image]
pri čemu R1, R2, R3, R4, R5, R6, R7, R8, R9, p i q su kako je definisano u patentnom zahtjevu 1;
c) reakcije intermedijera formule (III-a) ili (II-b) sa intermedijerom formule (IV) uz prisutnost pogodne baze i pogodnog otapala,
[image]
pri čemu R1, R2, R3, R4, R5, R6, R7, R8, R9, p i q su kako je definirano u patentnom zahtjevu 1 i pri čemu W1 predstavlja pogodnu odlaznu grupu;
d) reakcije intermedijera formule (VII) sa dietil cijanometilacetatom u prisutnosti natrij hidrida i pogodnog otapala,
[image]
pri čemu R1, R2, R4, R5, R6, R7, p i q su kako je definirano u patentnom zahtjevu 1;
ili, po želji, pretvaranjem spoja formule (Ia) ili (Ib) jednog u drugog slijedeći u struci poznate transformacije, i nadalje, po želji, pretvaranjem spoja formule (Ia) ili (Ib) u terapeutski aktivnu netoksičnu kiselinsku adicijsku sol tretiranjem sa kiselinom, ili u terapeutski aktivnu netoksičnu baznu adicijsku sol tretiranjem sa bazom, ili obrnuto, pretvaranjem oblika kisele adicijske soli u slobodnu bazu tretiranjem sa lužinom, ili pretvaranjem oblika bazne adicijske soli u slobodnu kiselinu tretiranjem sa kiselinom, i po želji, pripremom stereokemijskih izomernih oblika, kvaternih amina ili njegovih N-oksidnih formi.
28. Kombinacija (a) spoja prema bilo kojem od zahtjeva 1 do 20, i (b) jednog ili više drugih antibakterijskih sredstava.
29. Proizvod naznačen time da sadrži (a) spoj prema bilo kojem od zahtjeva 1 do 20, i (b) jedno ili više drugih antibakterijskih sredstava, kao kombinirani pripravak za istovremenu, odvojenu ili sekvencijalnu upotrebu pri liječenju bakterijske infekcije.
30. Spoj prema zahtjevu 25 naznačen time da je gram-pozitivna bakterija meticilin rezistentna Staphylococcus aureus.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06125546 | 2006-12-06 | ||
| PCT/EP2007/063312 WO2008068266A1 (en) | 2006-12-06 | 2007-12-04 | Antibacterial quinoline derivatives |
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| Publication Number | Publication Date |
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| HRP20100428T1 true HRP20100428T1 (hr) | 2010-09-30 |
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| HR20100428T HRP20100428T1 (hr) | 2006-12-06 | 2010-08-02 | Antibakterijski derivati kvinolina |
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| Country | Link |
|---|---|
| US (1) | US20100069366A1 (hr) |
| EP (1) | EP2099762B1 (hr) |
| JP (1) | JP5356244B2 (hr) |
| KR (1) | KR101514992B1 (hr) |
| CN (1) | CN101547907B (hr) |
| AP (1) | AP2478A (hr) |
| AR (1) | AR064153A1 (hr) |
| AT (1) | ATE467619T1 (hr) |
| AU (1) | AU2007328980B2 (hr) |
| BR (1) | BRPI0719920B8 (hr) |
| CA (1) | CA2668515C (hr) |
| CL (1) | CL2007003519A1 (hr) |
| CY (1) | CY1111188T1 (hr) |
| DE (1) | DE602007006553D1 (hr) |
| DK (1) | DK2099762T3 (hr) |
| EA (1) | EA200970534A1 (hr) |
| ES (1) | ES2345463T3 (hr) |
| HK (1) | HK1137441A1 (hr) |
| HR (1) | HRP20100428T1 (hr) |
| IL (1) | IL199079A (hr) |
| JO (1) | JO2684B1 (hr) |
| ME (1) | ME01127B (hr) |
| MX (1) | MX2009005982A (hr) |
| MY (1) | MY145924A (hr) |
| NO (1) | NO341996B1 (hr) |
| NZ (1) | NZ576863A (hr) |
| PL (1) | PL2099762T3 (hr) |
| PT (1) | PT2099762E (hr) |
| RS (1) | RS51382B (hr) |
| SI (1) | SI2099762T1 (hr) |
| TW (1) | TWI484959B (hr) |
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| JP5857511B2 (ja) * | 2010-08-10 | 2016-02-10 | 住友化学株式会社 | 植物病害防除組成物およびその用途 |
| KR102110366B1 (ko) | 2012-04-27 | 2020-05-14 | 얀센 파마슈티카 엔.브이. | 항균성 퀴놀린 유도체 |
| AU2013254674B2 (en) | 2012-04-27 | 2017-02-02 | Janssen Pharmaceutica Nv | Antibacterial quinoline derivatives |
| CN105017147B (zh) * | 2014-04-30 | 2019-02-01 | 中国医学科学院药物研究所 | 一种回收和利用Bedaquiline立体化学异构体的方法 |
| RU2664587C1 (ru) * | 2014-07-14 | 2018-08-21 | Шанхай Цзя Тань Фарматек Ко. Лтд. | Производные пиридина и их применение против микобактерий |
| 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 |
| 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 |
| BR122021024097B1 (pt) * | 2016-03-07 | 2024-04-30 | The Global Alliance For Tb Drug Development, Inc | Composto antibacteriano, uso do mesmo e composição farmacêutica |
| CN109384716B (zh) * | 2017-08-11 | 2021-06-29 | 海创药业股份有限公司 | 一种氘代喹啉化合物及其制备和用途 |
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| WO1998018326A1 (en) * | 1996-10-28 | 1998-05-07 | Department Of The Army, U.S. Government | Compounds, compositions and methods for treating antibiotic-resistant infections |
| UA82198C2 (uk) * | 2002-07-25 | 2008-03-25 | Янссен Фармацевтика Н.В. | Хінолінові похідні та їх використання як мікобактеріальних інгібіторів, спосіб їх одержання, фармацевтична композиція на їх основі, проміжна сполука |
| NZ547277A (en) * | 2004-01-23 | 2009-08-28 | Janssen Pharmaceutica Nv | Substituted quinolines and their use as mycobacterial inhibitors |
| 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 |
| UA83875C2 (ru) * | 2004-01-29 | 2008-08-26 | Янссен Фармацевтика Н.В. | Производные хинолина для применения в качестве микобактериальных ингибиторов |
| JO2524B1 (en) * | 2004-05-28 | 2010-03-17 | جانسن فارمسيتكا ان في | Use of substituted quinoline derivatives to treat drug-resistant microbial diseases |
| EP1677083A1 (fr) * | 2004-12-22 | 2006-07-05 | Roxer Industries S.A. | Capteur de niveau d'un liquide. |
| EE05697B1 (et) * | 2005-06-08 | 2014-02-17 | Janssen Pharmaceutica N.V. | Kinoliini derivaadid kui antibakteriaalsed toimeained |
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- 2009-06-02 IL IL199079A patent/IL199079A/en active IP Right Grant
- 2009-06-05 ZA ZA200903947A patent/ZA200903947B/xx unknown
- 2009-07-06 NO NO20092539A patent/NO341996B1/no unknown
-
2010
- 2010-02-04 HK HK10101244.0A patent/HK1137441A1/xx unknown
- 2010-08-02 HR HR20100428T patent/HRP20100428T1/hr unknown
- 2010-08-09 CY CY20101100742T patent/CY1111188T1/el unknown
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