HRP20191381T1 - Derivat hidroksamske kiseline - Google Patents

Derivat hidroksamske kiseline Download PDF

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Publication number
HRP20191381T1
HRP20191381T1 HRP20191381T HRP20191381T1 HR P20191381 T1 HRP20191381 T1 HR P20191381T1 HR P20191381 T HRP20191381 T HR P20191381T HR P20191381 T1 HRP20191381 T1 HR P20191381T1
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Croatia
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group
substituents
substituted
alkyl
alkylene
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Hajime Takashima
Risa Tsuruta
Tetsuya Yabuuchi
Yusuke Oka
Hiroki Urabe
Yoichiro Suga
Masato Takahashi
Fumito Uneuchi
Hironori Kotsubo
Muneo Shoji
Yasuko Kawaguchi
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Fujifilm Toyama Chemical Co Ltd
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Publication of HRP20191381T1 publication Critical patent/HRP20191381T1/hr

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/83—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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    • C07C271/06—Esters of carbamic acids
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    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
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    • C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
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    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
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    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
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    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
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    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
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    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
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Claims (13)

1. Spoj predstavljen sljedećom općom formulom [1] ili njegova farmaceutski prihvatljiva sol: naznačen time što R1 predstavlja skupinu C1-6 alkil, pri čemu skupina C1-6 alkil može biti supstituirana s 1 do 3 halogenih atoma koji su isti ili različiti, R2 predstavlja vodikov atom, ili metilnu skupinu, R3 predstavlja vodikov atom, R4 predstavlja metilnu skupinu, A1 predstavlja fenilen skupinu, L predstavlja -C≡C-, -C≡C-C≡C-, -CH=CH-, -CH=CH-C=C-, -C=C-CH=CH-, etilensku skupinu, ili vezu, A2 predstavlja dvovalentnu arilnu skupinu, dvovalentnu heterocikličku skupinu, dvovalentnu djelomično zasićenu kondenziranu policikličku ugljikovodičnu prstenastu skupinu, skupinu C3-8 cikloalkilen, skupinu C3-8 cikloalkenilen, skupinu C1-4 alkilen, ili skupinu C2-4 alkenilen, pri čemu dvovalentna arilna skupina, dvovalentna heterociklička skupina, dvovalentna djelomično zasićena kondenzirana policiklička ugljikovodična prstenasta skupina, skupina C3-8 cikloalkenilen, skupina C3-8 cikloalkilen, skupina C1-4 alkilen, i skupina C2-4 alkenilen mogu biti supstituirane s 1 do 4 supstituenata koji su isti ili različiti i koji su odabrani iz slijedeće skupine supstituenata, Rb: skupina supstituenata, Rb, sadrži halogeni atom, po izboru zaštićenu hidroksi skupinu, merkapto skupinu, cijano skupinu, nitro skupinu, po izboru zaštićenu amino skupinu, po izboru zaštićenu formil skupinu, po izboru zaštićenu karboksi skupinu, karbamoil skupinu, sulfo skupinu, ureido skupinu, gvanidido skupinu, skupinu C1-6 alkil, skupinu C3-8 cikloalkil, skupinu C1-6 haloalkil, skupinu C1-6 hidroksialkil, skupinu C1-6 alkoksi, skupinu C1-6 alkilamino, skupinu di(C1-6 alkil)amino, skupinu C1-6 alkoksikarbonil, skupinu C2-6 alkanoil, te arilnu skupinu, W predstavlja R6-X1-, ili Q-X1-Y2-X3-, Y2 predstavlja -O-, -NR7-, -CO-, -NR7CO-, -CONR7-, -S(O)n-, -OCO-, -COO-, - NR7SO2-, -SO2-NR7-, -OCOO-, -OCONR7-, -NR7CONR8-, ili vezu, X1 i X3 su isti ili različiti i svaki predstavlja skupinu C1-10 alkilen, skupinu C2-10 alkenilen, skupinu C2-10 alkinilen, skupinu C3-8 cikloalkilen, -C1-6 alkilen-C3-8 cikloalkilen-C1-6 alkilen-, ili vezu, pri čemu skupina C1-10 alkilen, skupina C2-10 alkenilen, skupina C2-10 alkinilen, skupina C3-8 cikloalkilen, i skupina -C1-6 alkilen-C3-8 cikloalkilen-C1-6 alkilen- mogu biti supstituirane s 1 do 4 supstituenata koji su isti ili različiti i odabrani su iz skupine supstituenata, Rc, koji će biti prikazani niže, Q predstavlja skupinu C3-8 cikloalkil, arilnu skupinu, ili heterocikličku skupinu, pri čemu skupina C3-8 cikloalkil, arilna skupina i heterociklička skupina mogu biti supstituirane s 1 do 4 supstituenata koji su isti ili različiti i odabrani su iz skupine supstituenata, Rc, koji će biti prikazani niže, te heterociklička skupina može imati različite ugljikove atome na prstenu premoštenom sa skupinom C1-6 alkilen ili skupinom -C1-6 alkilen-O-C1-6 alkilen-, R6 predstavlja vodikov atom, halogeni atom, po izboru zaštićenu hidroksi skupinu, merkapto skupinu, cijano skupinu, nitro skupinu, po izboru zaštićenu amino skupinu, po izboru zaštićenu formil skupinu, po izboru zaštićenu karboksi skupinu, karbamoil skupinu, sulfo skupinu, po izboru zaštićenu fosfatnu skupinu, ureido skupinu, gvanidido skupinu, R7-O-NR8-CO-, R8-ON=CR9-, R8-ON=CR9-NH-, R7-O-NR8-CH=N-, (R7)(R8)N-N=CH-, R8-O-NR8-, N≡C-NR8- ili skupinu C1-6 alkoksi, pri čemu C1-6 alkoksi skupina može biti supstituirana s 1 do 3 hidroksi skupine, R7 i R8 su isti ili različiti i svaki predstavljaju vodikov atom, skupinu C1-6 alkil, skupinu C3-8 cikloalkil, arilnu skupinu, ili heterocikličku skupinu, pri čemu skupina C1-6 alkil, skupina C3-8 cikloalkil, arilna skupina i heterociklička skupina mogu biti supstituirane s 1 do 4 supstituenata koji su isti ili različiti i odabrani su iz skupine supstituenata, Rc, koji će biti prikazani niže, R9 predstavlja vodikov atom, skupinu C1-6 alkil, skupinu C3-8 cikloalkil, amino skupinu, ili skupinu C1-6 alkilamino, i skupina supstituenata, Rc, sadrži halogeni atom, hidroksi skupinu, cijano skupinu, nitro skupinu, amino skupinu, karboksi skupinu, karbamoil skupinu, ureido skupinu, gvanidido skupinu, skupinu C1-6 alkil, skupinu C1-6 hidroksialkil, skupinu C1-6 haloalkil, skupinu C3-8 cikloalkil, skupinu C1-6 alkoksi, skupinu C3-8 cikloalkoksi, skupinu C1-6 alkoksikarbonil, skupinu C1-6 alkoksikarbonilamino, skupinu C2-6 alkanoil, skupinu C1-6 alkilsulfonil, skupinu C1-6 alkiltio, arilnu skupinu, heterocikličku skupinu, skupinu C1-6 alkiliden, skupinu C3-8 cikloalkiliden, monocikličku zasićenu heterociklidensku skupinu i skupinu hidroksiaminokarbonil; pri čemu amino skupina može biti supstituirana sa skupinom C2-6 alkanoil ili jednom ili dvije skupine C1-6 alkil; skupina C1-6 alkil može biti supstituirana s heterocikličkom skupinom; skupina C1-6 alkoksi može biti supstituirana s 1 do 3 supstituenata koji su isti ili različiti i odabrani su od hidroksi skupine, halogenog atoma, skupine C3-8 cikloalkil, skupine C1-6 alkoksi, arilne skupine i heterocikličke skupine; arilna skupina i heterociklička skupina mogu biti supstituirane s 1 do 4 supstituenata koji su isti ili različiti i odabrani su od halogenog atoma, hidroksi skupine, cijano skupine, nitro skupine, amino skupine, karboksi skupine i skupine C1-6 alkil; skupina C1-6 alkiliden može biti supstituirana sa skupinom C1-6 alkoksi; monociklička zasićena heterociklidenska skupina može biti supstituirana s 1 do 2 skupine C1-6 alkil.
2. Spoj predstavljen sljedećom općom formulom [1] ili njegova farmaceutski prihvatljiva sol, prema zahtjevu 1: naznačen time što R1 predstavlja metilnu skupinu, R2 predstavlja vodikov atom, ili metilnu skupinu, R3 predstavlja vodikov atom, R4 predstavlja metilnu skupinu, A1 predstavlja fenilen skupinu, L predstavlja -C≡C-, -C≡C-C≡C-, ili vezu, A2 predstavlja dvovalentnu arilnu skupinu, dvovalentnu heterocikličku skupinu, dvovalentnu djelomično zasićenu kondenziranu policikličku ugljikovodičnu prstenastu skupinu, skupinu C3-8 cikloalkilen, skupinu C1-4 alkilen, ili skupinu C2-4 alkenilen, pri čemu dvovalentna arilna skupina, dvovalentna heterociklička skupina, dvovalentna djelomično zasićena kondenzirana policiklička ugljikovodična prstenasta skupina, skupina C3-8 cikloalkilen, skupina C1-4 alkilen, i skupina C2-4 alkenilen mogu biti supstituirane s 1 do 4 supstituenata koji su isti ili različiti i odabrani su iz slijedeće skupine supstituenata, Rb: skupina supstituenata, Rb, sadrži halogeni atom, po izboru zaštićenu hidroksi skupinu, merkapto skupinu, cijano skupinu, nitro skupinu, po izboru zaštićenu amino skupinu, po izboru zaštićenu formil skupinu, po izboru zaštićenu karboksi skupinu, karbamoil skupinu, sulfo skupinu, ureido skupinu, gvanidido skupinu, skupinu C1-6 alkil, skupinu C3-8 cikloalkil, skupinu C1-6 haloalkil, skupinu C1-6 hidroksialkil, skupinu C1-6 alkoksi, skupinu C1-6 alkilamino, skupinu di(C1-6 alkil)amino, skupinu C1-6 alkoksikarbonil, skupinu C2-6 alkanoil, i arilnu skupinu, W predstavlja R6-X1-, X1 predstavlja skupinu C1-10 alkilen, skupinu C2-10 alkenilen, skupinu C2-10 alkinilen, skupinu C3-8 cikloalkilen, skupinu -C1-6 alkilen-C3-8 cikloalkilen-C1-6 alkilen- ili vezu, pri čemu skupina C1-10 alkilen, skupina C2-10 alkenilen, skupina C2-10 alkinilen, skupina C3-8 cikloalkilen, i skupina -C1-6 alkilen-C3-8 cikloalkilen-C1-6 alkilen- mogu biti supstituirane s 1 do 4 supstituenata koji su isti ili različiti i odabrani su iz skupine supstituenata, Rc, koji će biti prikazani niže, R6 predstavlja vodikov atom, halogeni atom, po izboru zaštićenu hidroksi skupinu, merkapto skupinu, cijano skupinu, nitro skupinu, po izboru zaštićenu amino skupinu, po izboru zaštićenu formil skupinu, po izboru zaštićenu karboksi skupinu, karbamoil skupinu, sulfo skupinu, po izboru zaštićenu fosfatnu skupinu, ureido skupinu, gvanidido skupinu, R7-O-NR8-CO-, R8-ON=CR9-, R8-ON=CR9-NH-, R7-O-NR8-CH=N-, (R7)(R8)N-N=CH-, R8-O-NR8-, N≡C-NR8- ili C1-6 alkoksi skupinu, pri čemu skupina C1-6 alkoksi može biti supstituirana s 1 do 3 hidroksi skupine, R7 i R8 su isti ili različiti i svaki predstavljaju vodikov atom, skupinu C1-6 alkil, skupinu C3-8 cikloalkil, arilnu skupinu, ili heterocikličku skupinu, pri čemu skupina C1-6 alkil, skupina C3-8 cikloalkil, arilna skupina i heterociklička skupina mogu biti supstituirane s 1 do 4 supstituenata koji su isti ili različiti i odabrani su iz skupine supstituenata, Rc, koji će biti prikazani niže, R9 predstavlja vodikov atom, skupinu C1-6 alkil, skupinu C3-8 cikloalkil, amino skupinu, ili skupinu C1-6 alkilamino, i skupina supstituenata, Rc, sadrži halogeni atom, hidroksi skupinu, cijano skupinu, nitro skupinu, amino skupinu, karboksi skupinu, karbamoil skupinu, ureido skupinu, gvanidido skupinu, skupinu C1-6 alkil, skupinu C1-6 hidroksialkil, skupinu C1-6 haloalkil, skupinu C3-8 cikloalkil, skupinu C1-6 alkoksi, skupinu C3-8 cikloalkoksi, skupinu C1-6 alkoksikarbonil, skupinu C1-6 alkoksikarbonilamino, skupinu C2-6 alkanoil, skupinu C1-6 alkilsulfonil, skupinu C1-6 alkiltio, arilnu skupinu, heterocikličku skupinu, skupinu C1-6 alkiliden, skupinu C3-8 cikloalkiliden, monocikličku zasićenu heterociklidensku skupinu i skupinu hidroksiaminokarbonil; pri čemu amino skupina može biti supstituirana sa skupinom C2-6 alkanoil ili jednom ili dvije skupine C1-6 alkil; skupina C1-6 alkil može biti supstituirana s heterocikličkom skupinom; skupina C1-6 alkoksi može biti supstituirana s 1 do 3 supstituenata koji su isti ili različiti i odabrani su od hidroksi skupine, halogenog atoma, skupine C3-8 cikloalkil, skupine C1-6 alkoksi, arilne skupine i heterocikličke skupine; arilna skupina i heterociklička skupina mogu biti supstituirane s 1 do 4 supstituenata koji su isti ili različiti i odabrani su od halogenog atoma, hidroksi skupine, cijano skupine, nitro skupine, amino skupine, karboksi skupine i skupine C1-6 alkil; skupina C1-6 alkiliden može biti supstituirana sa skupinom C1-6 alkoksi; monociklička zasićena heterociklidenska skupina može biti supstituirana s 1 do 2 skupine C1-6 alkil.
3. Spoj ili njegova farmaceutski prihvatljiva sol, prema patentnom zahtjevu 1 ili 2, naznačen time što W je R6-X1-, X1 je metilenska skupina ili veza, R6 je vodikov atom, po izboru zaštićena hidroksi skupina, ili R8-ON=CR9-, R8 je vodikov atom ili skupina C1-6 alkil, pri čemu skupina C1-6 alkil može biti supstituirana s 1 do 4 supstituenata koji su isti ili različiti i odabrani su iz skupine supstituenata, Rc, koji će biti prikazani niže, R9 je vodikov atom, skupina C1-6 alkil, skupina C3-8 cikloalkil, amino skupina, ili skupina C1-6 alkilamino, i skupina supstituenata, Rc, sadrži halogeni atom i hidroksi skupinu.
4. Spoj ili njegova farmaceutski prihvatljiva sol, prema patentnom zahtjevu 1, naznačen time što W je Q-X1-Y2-X3-, Y2 je -O-, -NR7-, ili veza, X1 je skupina C1-4 alkilen ili veza, pri čemu skupina C1-4 alkilen može biti supstituirana s 1 do 4 supstituenata koji su isti ili različiti i odabrani su iz skupine supstituenata, Rc, koji će biti prikazani niže, X3 je metilenska skupina, etilenska skupina, skupina C3-8 cikloalkilen, ili veza, pri čemu metilenska skupina i etilenska skupina mogu biti supstituirane s 1 do 2 metilne skupine, Q je skupina C3-8 cikloalkil, arilna skupina, ili heterociklička skupina, pri čemu skupina C3-8 cikloalkil, arilna skupina, ili heterociklička skupina mogu biti supstituirane s 1 do 4 supstituenata koji su isti ili različiti i odabrani su iz skupine supstituenata, Rc, prikazanih ispod R7 je vodikov atom, skupina C1-6 alkil ili skupina C3-8 cikloalkil, pri čemu skupina C1-6 alkil i skupina C3-8 cikloalkil mogu biti supstituirane s 1 do 4 supstituenata koji su isti ili različiti i odabrani su iz slijedeće skupine supstituenata, Rc, te skupina supstituenata, Rc, sadrži halogeni atom, hidroksi skupinu, skupinu C1-6 alkil, skupinu C1-6 hidroksialkil, skupinu C1-6 haloalkil, skupinu C3-8 cikloalkil, skupinu C1-6 alkoksi, skupinu C3-8 cikloalkoksi, skupinu C2-6 alkanoil, skupinu C1-6 alkiliden i skupinu hidroksiaminokarbonil; pri čemu skupina C1-6 alkoksi može biti supstituirana s 1 do 3 hidroksi skupine ili halogenih atoma; skupina C1-6 alkiliden može biti supstituirana sa skupinom C1-6 alkoksi.
5. Spoj ili njegova farmaceutski prihvatljiva sol, prema patentnom zahtjevu 1 ili 2, naznačen time što W je vodikov atom, halogeni atom, skupina C1-6 alkil, skupina C1-6 alkoksi, ili skupina C1-6 alkilamino, pri čemu skupina C1-6 alkil, skupina C1-6 alkoksi i skupina C1-6 alkilamino mogu biti supstituirane s 1 do 3 supstituenata koji su isti ili različiti i odabrani su iz skupine koju čine halogeni atom, hidroksi skupina, skupina C1-6 alkoksi i morfolino skupina.
6. Spoj ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time što R2 je vodikov atom.
7. Spoj ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time što R2 je metilna skupina.
8. Spoj ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time što L je veza ili -C≡C-.
9. Spoj ili njegova farmaceutski prihvatljiva sol, prema patentnom zahtjevu 8, naznačen time što L je veza.
10. Spoj ili njegova farmaceutski prihvatljiva sol, prema patentnom zahtjevu 8, naznačen time što L je -C≡C-.
11. Farmaceutski pripravak naznačen time što sadrži spoj ili njegovu farmaceutski prihvatljivu sol prema bilo kojem od patentnih zahtjeva 1 do 10.
12. Inhibitor LpxC naznačen time što sadrži spoj ili njegovu farmaceutski prihvatljivu sol prema bilo kojem od patentnih zahtjeva 1 do 10.
13. Antimikrobno sredstvo naznačeno time što sadrži spoj ili njegovu farmaceutski prihvatljivu sol prema bilo kojem od patentnih zahtjeva 1 do 10.
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