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DK2686310T5 - Benzodioxan-inhibitorerafleukotrien-produktion - Google Patents

Benzodioxan-inhibitorerafleukotrien-produktion Download PDF

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Publication number
DK2686310T5
DK2686310T5 DK12711504.6T DK12711504T DK2686310T5 DK 2686310 T5 DK2686310 T5 DK 2686310T5 DK 12711504 T DK12711504 T DK 12711504T DK 2686310 T5 DK2686310 T5 DK 2686310T5
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Denmark
Prior art keywords
dihydro
benzyl
pyridin
dioxino
mmol
Prior art date
Application number
DK12711504.6T
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English (en)
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DK2686310T3 (da
Inventor
Asitha Abeywardane
Michael J Burke
Thomas Martin Kirrane Jr
Matthew Russell Netherton
Anil Kumar Padyana
Keenan Lana Louise Smith
Hidenori Takahashi
Michael Robert Turner
Qiang Zhang
Qing Zhang
Original Assignee
Boehringer Ingelheim Int
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Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int
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Publication of DK2686310T3 publication Critical patent/DK2686310T3/da
Publication of DK2686310T5 publication Critical patent/DK2686310T5/da

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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A—HUMAN NECESSITIES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
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    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • 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
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    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring

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Claims (9)

  1. P A t E N T K R A V
    1, Forbindelse valgt fra gruppen bestående af: 4--(F-{4“[(2S}-2,3"dihydrO"l,4--benzodiøxin“2-y!jbenzyS}piperidtn-4-yi)butansyre; 4-(i-{4-[(3S}-2i3-dlhydro[l,43dfoxino[2f3-b]pyridin-3-yiJbenzyl>piperldtn-4- yi)benzoesyre; (3S)-3-{4-[(lS,4S}-?~azabicyclo[2,2,l3bept-7-yimethyl]pheny|>-2,3- dihydro[i,43dioxino[2,3-b]pyridin; N-{l-{4-[(3S)-2,3-dibydro[lf4]dioxino|:2,3-b]pyr)din~3-y!]benzyl|pipertdin-4- yOmethansulfonamid; (3S}*3-[4-(azepan-i-ylmethyl)phenyl]-2,3-dihydro[t,4ldioxi!io[2i3-b]pyridin; l''{4-[(2S}~2i3-dihydro-l,4*benzodioxin-2*y!3benzyl>-2-methylpiperidin; 7~{4-[(2S)-2,3-dthydro-Jl?4*benzodtox)n-2-y!3benzyl>*li7-d!azaspiro[4,4]norian-l* carboxamid; 7- {4-[(3S)-2J3-dihydro[if4]dioxino[2#3-b3pyridin-3-y!]benzyi}-l17-d)azaspiro[4,4jnonan-2-on; i“{4-[{2S3-2f3-dihydro-l,4”benzodtoxin-2-yljbenzy1}piperidin-4-carboxylsyre; (l--(4-[(2S)“2/3-dihydro-i,4-benzodtoxin-2-ylJbenzyi[piperidin-4-yl}(morpholin-4- y!)methanon; 8- {4-i(3S}-2f3"dfhydro[i>4jdioxino[2f3-b3pyridin-3-yl]benzyi}-l,3,8- triazaspiro[4.5jdecan-2f4-dion; (3S}-3-{4-'[(3-n'iethoxypiper]din-i-'yi)riiethy!3pbenyi}-2)3"Gihydro[l,4]d!Oxino[2.3- bjpyrSdin; N*(i-{4-[(2S)-2y3-dihydro-l,4'benzodioxin-2'yf]benzyi}pyrroiidin-3'yi)-N- methylacefcamid; l“{4"[{2S)“2f3"dihydrO“l,4"benzod!oxin"2“yljbenzyS>“4-(lfl"dioxfdO“l,2-thiazo!idin“ 2-y!)pipérfdin; (3P.}"l'{4“[{3S)-2i3*dshydro[l,43dioxino[2.3'bjpyndin-3-yrjbenzyl}pyrroiidin-3-oi; W-( l-{4-[(3S}~2,3-d!hydro[l,4jdfOXino[2,3-bjpyridin-3-Y!jbenzyi>pipendin-4-yl)-2-hydroxyacetamid; 4-[(i-{4· [(3S}-2,3-dihydro[l/4]dioxino[2,3-b]pyndin"3“yi]ben?.y!}pipendin-4" y I }met hyi j benzoesyre ; (1- {4-[(3S)-2(3“d!hydro[i,4]dioxino[2,3‘b]pyridin"3-yijbenzyi}p!peridin-4* yi}(morphoiin"4-yf)methanon; (3S)-3-[4-(morphoiin-4-y!methyi)phenyl3-2,3-dihydro[if4]d!ox!noi2)3*bjpyndin; 8-{4~[(2S}-2,3-dfbydro~l,4-benzodfOxin~2-yi3benzyf}-2,8-diazaspiro[4f53decari-i- on; l“{4-[(3S)“2i3-dfhydro[ii4]dioxino[2i3“b3pyridin"3“yl]benzy!>pipendin”4"Carbonitrfl; l--(4~[(2S)-2,3-dihydro~i,4-benzodioxfn~2-yi3benzy!}-N-methylpiperldin~4-' carboxamid; S—f tC^S) ~2,3-di hydroX 1,4]ci iox i r\o [2,3-ti3py rid irv-3 -y Π benzyi} - 2^6 -diazaspiro[4,5]decan-l-on; N-(i-{4-'[(3S)-2#3-dihydro[li43dioxino[2,3-b]pyfidin-3“yi3benzyl>piperidin-4-yl)-2“ hydroxy-2-mefchylpropanamid; N-(i-{4“[(3S)-2#3-dihydTO[lf43dioxini.0|2>;3^:bJ^:i1:din-3-yl]^hzyl>pipir:i||^4-Yl)'-l- hydroxycyciopropancarboxamid; N-<4-[{2S)-2,3"dihydrO"l,4-benzodfoxin~2-yl3benzy!>-N-efchylcydopentanamfne; l~{4-[(3S)“2,3-d!hydro[i,4]d)OXino[2,3~b3pyndin-3~yl]ben2yi}~N~methyipiperid!n-4~ carboxamid; N'-{4-[{3S}-2,3~dihydroti,4]dioxino[2i3'‘b3pyridin-3-y!3benzyl>'N- methylcyciopentanamine; l~[(l*{4-[t3S)-2i3-dihydro[l,4]diox!no[2,3-b]pyridin-3~yl3benzyi>ptperidin-3* y!}methyi3pyrroiidin-2-on; l~{4-[(2S}-2,3-dihydro-l,4-benzodioxin-2-yS3benzy!}-2-methyipyrroiidin; N-{4-[(3S}“2,3-d)hydro[i,43dfOxino[2,3-b3pyridtn-3“yl3benzyl}-2-methyl“i- {pyrroiidin-l-yf)propan-2-amin; N-cyclohexyi-N-{4-[(2S}-2,3-dihydro-l,4-benzodioxin-2-yi3benzyl>-N'/N’- dimethylefchan~i,2-diamin; N-Cl-{4-[(3S}-2/3-d!hYdro[l,43dfOxino[2,3-bJpyrtdin-3-yfibenzyl}pipendin-4- yijacetamid; N-{4~[(3S}-2,3~dihydro[i,4]dioxino[2,3-b] pyridin-3-y!3benzyi}-N-metby|-:2-(pyfidin-2-yl)ethanamin; (3S}-3'[4-(pyrrøi:tdin-l-ySmethyS)pheny1]-2,3-dibydr0|:i,4]dibXfn0[2,3'b]pyndiHi: i*{4“i{3S)-2,3-dihydro{i)4jdioxinoi2,3-b3pyridin-3-yf]benzyS}pfpertdin-3- carboxamid; l-{4-[(3S)-2,3-di hydro[ l,4]dioxino[ 2,3^ b]pyridin*3-y l]benzyi}pjperidin*4- carboxamSd; N-(l-{4-[{2S)-2/3-dihYdro-li4-benzodioxin-2-yf]benzy!}pyrrofSdin-3-yf)acatamid; l"{4~[{3S)-2,3~dihydro[l,43dioxino[2,3“b3pyridin-3-y!3benzyS}“N-{2~ hydroxyethyi}piperidin-4 "Carboxamid; (3S}-3-[4-(l,4-oxa2epan-4-y!methy!3pbeny!3“2f3-dihydroii,43dioxino[2)3*bjpyndln; i-{4-[(2S)-2,3-dihydro-l,4-benzod!oxin-2“yi3benzyf}“N“(2-hydroxyethyl)pfpendin-4- carboxamid; 4-(l-{4-i(2S}-2f3-dihydro-l,4-benzodioxln-2“y!]benzy!}pfperidin-4-y1)benzoesyre; l"{l~{4-[(2S}~2f3"dihydro-l,4-benzodioxin-2~y!]benzyi}psperfdsn-4-yi}urea; 7’"{4-[(2S)-2i3~dihydro-l,4-benzodioxin-2-yi]ben2yS}-l,7-dia2aspiro[4f4]nanan-2- on; ®“{’4“E(3S)"2,3-dihydro[ii43dioxir!o[2,3-b3pyrldin-3"y!]benzyf}-2~methyl-2,S- dia2aspiro[4i5]decan-l-on; l-{4-[(3S)-2f3-dihydro[l/4]dioxino[2,3-b'jpyridin-3-yrjben2yi}pipendln-4-Gi; N - (i - {4-[{ 2S) - 2,3-di hy d ro-1 ,4-benzodioxin-2 -yi] benzyl }piperidl n-4 -ylimethansulfonamid; 3- (i-{4-[(3S}-2/3-dibydro[l,43dfoxino[2f3-b]pyridin-3-yi3benzyl>piperldtn-4-yl}propan~l-oi; (3S)-3-{4-'[(4-mefchylptpertdin-i~yi)methyi3pbenyl>-'2/3'-dihydro[l,43dtoxino[2,3- bjpyridin; N-{4~[(3S)-2,3~dihydro[l,4Jdioxino[2,3-b]pyridin-3-y]]benzyi}-N-ethy!ethanarnine; N-'{4~[(3S}-2,3~dibydro[i,43dfOxino[2,3-bjpyridin-3-y!]benzyi>-i~ {methy!su!fonyl}psperSdln-4~amin; (3S)-3-{4*[(4-fluorpiperidin*l-yl}metbyl]phebyi}^2,3id3:bydmE:i>:43dioXiPo[2,3- bjpyridin; 1. (4-{4-[{3S}-2i3~dlhydro[l,43dioxino[2i3-b3pyf*din-3-yi3benzyl}-l,4~diazepan-i-yi}-ethanon; E{3R)-i-C4-E{2S}-2,3-dthydro-l,4"benzodioxin-2-yi3benzyi}p!pendin-3- yljeddikesyre; (l-'C4-[{3S}-2i3-dihydro[if43:dioxf0o[2,3-b3pyridSn-3-y!]benzyl}pipendin-4- yijmethanoi; 4~[(l-{4-[(2S}-2,3-dShydrQ-i,4-benzodioxin-2-yi3benzYi}piperidin~4- yi}methyl]benzoesyre; (3S}-3~{4-[(4-methy!~i,4-diazepan-l~yi}roelt>y!]phef!yi}~2;3- dthydro[l,43dfoxino[2>3‘b]pyridtn; (3S)-3-{4-[(3-methoxypyrrolidtn-l-yl)methyl]pbenyi>-2,3-dihydro[i,4]dioxtno[2,3- bjpyrldin; 4- (4-[(3S)-2,3-dihydro[ii4]dioxino[2/3-b3pyridin-3-y!]benzyi>plperazin-l-carboxamid; og N~{4-[(2S}-2,3-dihydro-l,4-benzodioxin~2-yi3benzyi}-N,2-dimethylpropan-2-3min; eifer Et farmaceutisk acceptabelt salt deraf,
  2. 2. Forbindelse ifølge krav 1, hvilken forbindelse er 4-{4-[(3S)-2,3· dihydro[if4]dioxino[2,3-b3pyridin-3-yi]benzyl}pfperazin-l-carboxamid eller et farmaceutisk acceptabelt salt deraf,
  3. 3. Forbindelse tfølge krav 1, hvilken forbindelse er l-{4-[(2S)-2,3-dihydro-l,4-benzødioxfn-2-yi]benzy!>ptpendtn-4-carboxyisyre eller et farmaceutisk acceptabelt salt deraf,
  4. 4. Forbindelse ifølge krav i, hvilken forbindelse er [(3R)-l-(4-[(2S}-2,3-dihydro-li4-benzodtoxin“2-yl]benzy!>pipendin-3-yl]eddikesyre eller et farmaceutisk acceptabelt sait deraf.
  5. 5. Farmaceutisk sammensætning omfattende forbindelsen ifølge et hvilket som heist af kravene Its! 4, eller et farmaceutisk acceptabelt salt deraf,
  6. 6. Forbindelse ifølge et hviiket som helst af kravene 1 til 4, eller et farmaceutisk acceptabelt salt deraf, ti! anvendelse som lægemiddel.
  7. 7. Forbindelse ifølge et hvilket som helst af kravene 1 til 4, eller et farmaceutisk acceptabelt salt deraf, ti! anvendelse i en fremgangsmåde ti! behandling af en kardiovaskuiær sygdom.
  8. 8. Forbindelse til anvendelse Ifølge krav?, hvor den kardiovaskulære sygdom er valgt fra gruppen bestående af ateroskierose, myokardieinfarkt, slagtilfælde, aorta-aneurisme, segiceiiekrise, iskøemiereperfusionsskade, pulmonai arteriel hypertension og sepsis.
  9. 9. Forbindelse til anvendelse ifølge krav 7, hvor den kardiovaskulære sygdom er afce- roskierose.
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