HRP20110510T1 - Heteroaril-supstituirani piperidini - Google Patents
Heteroaril-supstituirani piperidini Download PDFInfo
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- HRP20110510T1 HRP20110510T1 HR20110510T HRP20110510T HRP20110510T1 HR P20110510 T1 HRP20110510 T1 HR P20110510T1 HR 20110510 T HR20110510 T HR 20110510T HR P20110510 T HRP20110510 T HR P20110510T HR P20110510 T1 HRP20110510 T1 HR P20110510T1
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- 150000003053 piperidines Chemical class 0.000 title 1
- -1 monofluoromethyl Chemical group 0.000 claims abstract 57
- 150000001875 compounds Chemical class 0.000 claims abstract 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 28
- 125000001424 substituent group Chemical group 0.000 claims abstract 25
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract 11
- 150000002367 halogens Chemical class 0.000 claims abstract 11
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 7
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract 5
- 125000005368 heteroarylthio group Chemical group 0.000 claims abstract 4
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 4
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims abstract 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 4
- 238000011321 prophylaxis Methods 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 230000023555 blood coagulation Effects 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 238000000338 in vitro Methods 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 230000009424 thromboembolic effect Effects 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 230000010100 anticoagulation Effects 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
- 229910052801 chlorine Chemical group 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 abstract 1
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Abstract
Spojevi formule naznačeni time daA predstavlja skupinu formule gdje # je točka vezanja na piperidinski prsten, i* je točka vezanja na R2,R1 predstavlja fenil, gdje fenil može biti supstituiran sa 1 do 3 supstituenata odabranih nezavisno jedan od drugoga iz skupine koja sadrži monofluorometil, difluorometil, trifluorometil, monofluorometoksi, difluorometoksi, trifluorometoksi, monofluorometilsulfanil, difluorometilsulfanil, trifluorometilsulfanil, metilsulfonil, C1-C4-alkil, C1-C4-alkoksi, C1-C4-alkoksikarbonil i C3-C6- cikloalkil, gdje C2-C4-alkoksi može biti supstituiran sa supstituentom odabranim iz skupine koja sadrži metoksi i etoksi, igdje cikloalkil može biti supstituiran sa 1 do 3 supstituenta odabrana nezavisno jedan od drugoga iz skupine koja sadrži halogen i C1-C4- alkil, R2 predstavlja vodik, trifluorometil, aminometil, C1-C6-alkil, C2-C6-alkenil, C1- C4-alkoksikarbonil, C3-C6-cikloalkil, ciklopentenil, 4- do 6-člani heterociklil, fenil, 1,3-benzodioksolil, 5- ili 6-člani heteroaril ili piridilaminokarbonil, gdje cikloalkil, heterociklil, fenil i heteroaril mogu biti supstituirani sa 1 do 3 supstituenta odabrana nezavisno jedan od drugoga iz skupine koja sadrži halogen, cijano, amino, monofluorometil, difluorometil, trifluorometil, monofluorometoksi, difluorometoksi, trifluorometoksi, monofluorometilsulfanil, difluorometilsulfanil, trifluorometilsulfanil, C1-C4-alkil, C1-C4-alkoksi, C1-C6-alkilamino, C1-C4-alkoksikarbonilamino, C3-C6-cikloalkil, 4- do 6-člani heterociklil, fenil i 5- ili 6-člani heteroaril, gdje alkilamino može biti supstituiran sa supstituentom odabranim iz skupine koja sadrži C1-C4-alkoksi i C1-C6-alkilamino, igdje C1-C4-alkil može biti supstituiran sa supstituentom odabranim iz skupine koja sadrži halogen, hidroksil, amino, aminokarbonil, C1-C4-alkoksi, C1-C6- alkilamino, C1-C4-alkiltio, C1-C4-alkilkarbonil, C1-C4-alkilkarboniloksi, C1-C4- alkilsulfonil, C1-C4-alkoksikarbonil, C1-C4-alkoksikarbonilamino, C3-C6- cikloalkil, C3-C6-cikloalkilamino, 4- do 6-člani heterociklil, fenil, fenoksi, 5- ili 6-člani heteroaril i 5- ili 6-člani heteroariltio, gdje cikloalkil, heterociklil, fenil, fenoksi, heteroaril i heteroariltio mogu biti supstituirani sa 1 do 3 supstituenta odabrana nezavisno jedan od drugoga iz skupine koja sadrži halogen, cijano, hidroksimetil, monofluorometil, difluorometil, trifluorometil, monofluorometoksi, difluorometoksi, trifluorometoksi, monofluorometilsulfanil, difluorometilsulfanil, trifluorometilsulfanil, C1- C4-alkil, C1-C4-alkoksi, C3-C6-cikloalkil, 4- do 6-člani heterociklil, fenil i 5- ili 6-člani heteroaril, R3 predstavlja C1-C6-alkil, C1-C6-alkoksi, C1-C6-alkilamino, C3-C7-cikloalkil, 4- do 6-člani heterociklil, fenil ili 5- ili 6-člani heteroaril, gdje alkil, C2-C6-alkoksi i alkilamino mogu biti supstituirani sa supstituentom odabranim iz skupine koja sadrži hidroksil, amino, cijano i C1-C4-alkoksi, igdje cikloalkil, heterociklil, fenil i heteroaril mogu biti supstituirani sa 1 do 3 supstit
Claims (13)
1. Spojevi formule
[image]
naznačeni time da
A predstavlja skupinu formule
[image]
[image]
[image]
gdje
# je točka vezanja na piperidinski prsten,
i
* je točka vezanja na R2,
R1 predstavlja fenil,
gdje fenil može biti supstituiran sa 1 do 3 supstituenata odabranih nezavisno jedan od drugoga iz skupine koja sadrži monofluorometil, difluorometil, trifluorometil, monofluorometoksi, difluorometoksi, trifluorometoksi, monofluorometilsulfanil, difluorometilsulfanil, trifluorometilsulfanil, metilsulfonil, C1-C4-alkil, C1-C4-alkoksi, C1-C4-alkoksikarbonil i C3-C6- cikloalkil,
gdje C2-C4-alkoksi može biti supstituiran sa supstituentom odabranim iz skupine koja sadrži metoksi i etoksi,
i
gdje cikloalkil može biti supstituiran sa 1 do 3 supstituenta odabrana nezavisno jedan od drugoga iz skupine koja sadrži halogen i C1-C4- alkil,
R2 predstavlja vodik, trifluorometil, aminometil, C1-C6-alkil, C2-C6-alkenil, C1- C4-alkoksikarbonil, C3-C6-cikloalkil, ciklopentenil, 4- do 6-člani heterociklil, fenil, 1,3-benzodioksolil, 5- ili 6-člani heteroaril ili piridilaminokarbonil,
gdje cikloalkil, heterociklil, fenil i heteroaril mogu biti supstituirani sa 1 do 3 supstituenta odabrana nezavisno jedan od drugoga iz skupine koja sadrži halogen, cijano, amino, monofluorometil, difluorometil, trifluorometil, monofluorometoksi, difluorometoksi, trifluorometoksi, monofluorometilsulfanil, difluorometilsulfanil, trifluorometilsulfanil, C1-C4-alkil, C1-C4-alkoksi, C1-C6-alkilamino, C1-C4-alkoksikarbonilamino, C3-C6-cikloalkil, 4- do 6-člani heterociklil, fenil i 5- ili 6-člani heteroaril,
gdje alkilamino može biti supstituiran sa supstituentom odabranim iz skupine koja sadrži C1-C4-alkoksi i C1-C6-alkilamino,
i
gdje C1-C4-alkil može biti supstituiran sa supstituentom odabranim iz skupine koja sadrži halogen, hidroksil, amino, aminokarbonil, C1-C4-alkoksi, C1-C6- alkilamino, C1-C4-alkiltio, C1-C4-alkilkarbonil, C1-C4-alkilkarboniloksi, C1-C4- alkilsulfonil, C1-C4-alkoksikarbonil, C1-C4-alkoksikarbonilamino, C3-C6- cikloalkil, C3-C6-cikloalkilamino, 4- do 6-člani heterociklil, fenil, fenoksi, 5- ili 6-člani heteroaril i 5- ili 6-člani heteroariltio,
gdje cikloalkil, heterociklil, fenil, fenoksi, heteroaril i heteroariltio mogu biti supstituirani sa 1 do 3 supstituenta odabrana nezavisno jedan od drugoga iz skupine koja sadrži halogen, cijano, hidroksimetil, monofluorometil, difluorometil, trifluorometil, monofluorometoksi, difluorometoksi, trifluorometoksi, monofluorometilsulfanil, difluorometilsulfanil, trifluorometilsulfanil, C1- C4-alkil, C1-C4-alkoksi, C3-C6-cikloalkil, 4- do 6-člani heterociklil, fenil i 5- ili 6-člani heteroaril,
R3 predstavlja C1-C6-alkil, C1-C6-alkoksi, C1-C6-alkilamino, C3-C7-cikloalkil, 4- do 6-člani heterociklil, fenil ili 5- ili 6-člani heteroaril,
gdje alkil, C2-C6-alkoksi i alkilamino mogu biti supstituirani sa supstituentom odabranim iz skupine koja sadrži hidroksil, amino, cijano i C1-C4-alkoksi,
i
gdje cikloalkil, heterociklil, fenil i heteroaril mogu biti supstituirani sa 1 do 3 supstituenta odabrana nezavisno jedan od drugoga iz skupine koja sadrži halogen, cijano, nitro, okso, hidroksil, amino, aminometil, monofluorometil, difluorometil, trifluorometil, monofluorometoksi, difluorometoksi, trifluorometoksi, monofluorometilsulfanil, difluorometilsulfanil, trifluorometilsulfanil, hidroksikarbonil, aminokarbonil, C1-C4-alkil, C1-C4- alkoksi, C1-C6-alkilamino, C1-C4-alkoksikarbonil i C1-C4-alkilaminokarbonil,
ili jedna od njihovih soli, njihovih solvata ili solvata njihovih soli.
2. Spoj prema zahtjevu 1, naznačen time da
A predstavlja skupinu formule
[image]
[image]
gdje
# je točka vezanja na piperidinski prsten,
i
* je točka vezanja na R2,
R1 predstavlja fenil,
gdje je fenil supstituiran sa 1 ili 2 supstituenta odabrana nezavisno jedan od drugoga iz skupine koja sadrži trifluorometil, trifluorometoksi, metil, etil, izopropil i metoksi,
R2 predstavlja metil, etil, izopropil, n-propil, tert-butil, metoksikarbonil, etoksikarbonil, ciklopropil, ciklobutil, azetidinil, oksetanil, pirolidinil, tetrahidropiridinil, fenil, 1,3-benzodioksolil, tienil, furanil, pirolil, tiazolil, izoksazolil, imidazolil, triazolil, piridil, pirimidinil ili pirazinil,
gdje azetidinil, oksetanil, pirolidinil, tetrahidropiridinil, fenil, tienil, furanil, pirolil, tiazolil, izoksazolil, imidazolil, triazolil, piridil, pirimidinil i pirazinil mogu biti supstituirani sa 1 do 2 supstituenta odabrana nezavisno jedan od drugoga iz skupine koja sadrži halogen, trifluorometil, trifluorometoksi, metil, etil, metoksi, etoksi i etilamino,
gdje etilamino može biti supstituiran sa supstituentom odabranim iz skupine koja sadrži metoksi i dimetilamino,
i
gdje metil i etil mogu biti supstituirani sa supstituentom odabranim iz skupine koja sadrži hidroksil, amino, metoksi, etoksi, izopropoksi, dialkilamino, metilsulfonil, ciklopropilamino, morfolinil, fenil i fenoksi,
gdje fenil može biti supstituiran sa 1 ili 2 supstituenta odabrana nezavisno jedan od drugoga iz skupine koja sadrži halogen, hidroksimetil, trifluorometil, trifluorometoksi, metil, etil, metoksi i etoksi,
R3 predstavlja tert-butil, N-metil-N-etilamino, metoksialkilamino, ciklopropil, ciklopentil, azetidinil, 3,3-difluoroazetidinil, 3-hidroksiazetidinil, 3-metilazetidinil, 3-metoksiazetidinil, 3-dimetilaminoazetidinil, piroldinil, 3,3-difluoropiroldin-1-il, 3-hidroksipiroldin-1-il, 3-aminopiroldin-1-il, 4,4-difluoropiperidin-1-il, 4-hidroksipiperidin-1-il, 4-aminopiperidin-1-il, 4-cijanopiperidin-1-il, 3-metoksipiperidin-1-il, tiazolidinil, morfolin-4-il, 2,2- dimetilmorfolin-4-il, 2-oksopiperazin-1-il ili 3-okso-4-metilpiperazin-1-il,
ili jedna od njegovih soli, njegovi solvati ili solvati njegovih soli.
3. Spoj prema zahtjevu 1 ili 2, naznačen time da
A predstavlja skupinu formule
[image]
gdje
# je točka vezanja na piperidinski prsten,
i
* je točka vezanja na R2,
R1 predstavlja fenil,
gdje je fenil supstituiran sa 1 ili 2 supstituenta odabrana nezavisno jedan od drugoga iz skupine koja sadrži trifluorometil, trifluorometoksi, metil i etil,
R2 predstavlja metil, etil ili izopropil,
gdje metil i etil mogu biti supstituirani sa metoksi supstituentom,
R3 predstavlja 3-hidroksiazetidinil, 3-hidroksipiroldin-1-il, 4-hidroksipiperidin-1-il, 4-cijanopiperidin-1-il ili morfolin-4-il,
ili jedna od njegovih soli, njegovi solvati ili solvati njegovih soli.
4. Spoj prema bilo kojem od zahtjeva 1 do 3, naznačen time da su supstituenti -R1 i -A-R2 u cis-položaju jedan prema drugome.
5. Postupak za pripremu spoja prema formuli (I) ili jedne od njegovih soli, njegovih solvata ili solvata njegovih soli prema zahtjevu 1, naznačen time da bilo koji
[A] poj prema formuli
[image]
pri čemu
R1 i R3 imaju značenje dano u zahtjevu 1,
reagira sa spojem prema formuli
[image]
pri čemu
R2 ima značenje dano u zahtjevu 1,
ili
[B] spoj prema formuli
[image]
pri čemu
R1 i R3 imaju značenje dano u zahtjevu 1,
reagira sa spojem prema formuli
[image]
pri čemu
R2 ima značenje dano u zahtjevu 1, te
X1 predstavlja brom ili klor,
ili
[C] spoj prema formuli (II) reagira sa spojem prema formuli
R2CONHNH2 (XVI),
pri čemu
R2 ima značenje dano u zahtjevu 1,
u prisutnosti fosforil klorida ili tionil klorida
ili
[D] spoj prema formuli (II), u prvome koraku, reagira sa spojem prema formuli
R2COCH2NH2 (XVII),
pri čemu
R2 ima značenje dano u zahtjevu 1,
u prisutnosti tionil klorida ili fosforil klorida,
te, u drugom koraku, reagira sa Lawessonovim reagensom
ili
[E] spoj prema formuli (II) reagira sa spojem prema formuli (XVII) u prisutnosti tionil klorida ili fosforil klorida
ili
[F] spoj prema formuli (II) u prvome koraku, reagira sa spojem prema formuli (XVI ) u prisutnosti tionil klorida ili fosforil klorida, te drugom koraku, reagira sa Lawessonovim reagensom
ili
[G] spoj prema formuli
[image]
pri čemu
R1 i R3 imaju značenje dano u zahtjevu 1, i
R4 predstavlja metil ili etil,
reagira sa spojem prema formuli
[image]
pri čemu
R2 ima značenje dano u zahtjevu 1,
u prisutnosti butilitija
ili
[H] spoj prema formuli
[image]
pri čemu
R1 i R3 imaju značenje dano u zahtjevu 1,
reagira sa spojem prema formuli
[image]
pri čemu
R2 ima značenje dano u zahtjevu 1,
ili
[J] spoj prema formuli
[image]
pri čemu
A, R1 i R2 imaju značenje dano u zahtjevu 1,
u prvome koraku, reagira sa 4-nitrofenil kloroformatom, te u drugom koraku, reagira sa spojem prema formuli
R3—H (XXII),
pri čemu
R3 ima značenje dano u zahtjevu 1.
6. Spoj prema bilo kojem od zahtjeva 1 do 4 naznačen time da je za liječenje i/ili profilaksu bolesti.
7. Uporaba spoja prema bilo kojem od zahtjeva 1 do 4 naznačena time da je za pripremu lijeka za liječenje i/ili profilaksu bolesti.
8. Uporaba spoja prema bilo kojem od zahtjeva 1 do 4 naznačena time da je za pripremu lijeka za liječenje i/ili profilaksu kardiovaskularnih poremećaja, tromboembolijskih poremećaja i/ili tumorskih poremećaja
9. Uporaba spoja prema bilo kojem od zahtjeva 1 do 4 naznačena time da je za sprečavanje koagulacije krvi in vitro.
10. Lijek, naznačen time da sadrži spoj prema bilo kojem od zahtjeva 1 do 4 u kombinaciji sa inertnom ne-toksičnom farmaceutski prihvatljivom pomoćnom tvari.
11. Lijek, naznačen time da sadrži spoj prema bilo kojem od zahtjeva 1 do 4 u kombinaciji sa daljnjim aktivnim spojem.
12. Lijek prema zahtjevu 10 ili 11 naznačen time da je za liječenje i/ili profilaksu kardiovaskularnih poremećaja, tromboembolijskih poremećaja i/ili tumorskih poremećaja.
13. Postupak za sprečavanje koagulacije krvi in vitro, naznačen time da je dodana anti-koagulacijska količina spoja prema bilo kojem od zahtjeva 1 do 4
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007057718A DE102007057718A1 (de) | 2007-11-30 | 2007-11-30 | Heteroaryl-substituierte Piperidine |
| DE102008010221A DE102008010221A1 (de) | 2008-02-20 | 2008-02-20 | Heteroaryl-substituierte Piperidine |
| PCT/EP2008/009792 WO2009068214A2 (de) | 2007-11-30 | 2008-11-20 | Heteroaryl-substituierte piperidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110510T1 true HRP20110510T1 (hr) | 2011-08-31 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| HR20110510T HRP20110510T1 (hr) | 2007-11-30 | 2011-07-07 | Heteroaril-supstituirani piperidini |
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|---|---|
| US (2) | US8119663B2 (hr) |
| EP (1) | EP2227466B1 (hr) |
| JP (1) | JP5450435B2 (hr) |
| KR (1) | KR20100114018A (hr) |
| CN (1) | CN101932577B (hr) |
| AR (1) | AR069417A1 (hr) |
| AT (1) | ATE506359T1 (hr) |
| CA (1) | CA2706991A1 (hr) |
| CL (1) | CL2008003473A1 (hr) |
| DE (1) | DE502008003324D1 (hr) |
| DK (1) | DK2227466T3 (hr) |
| HK (1) | HK1152311A1 (hr) |
| HR (1) | HRP20110510T1 (hr) |
| PA (1) | PA8805201A1 (hr) |
| PE (1) | PE20091026A1 (hr) |
| PL (1) | PL2227466T3 (hr) |
| PT (1) | PT2227466E (hr) |
| TW (1) | TW200936135A (hr) |
| UY (1) | UY31484A1 (hr) |
| WO (1) | WO2009068214A2 (hr) |
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| DE102009014484A1 (de) | 2009-03-23 | 2010-09-30 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Piperidine |
| DE102009022896A1 (de) * | 2009-05-27 | 2010-12-02 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Piperidine |
| DE102009022897A1 (de) * | 2009-05-27 | 2010-12-02 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Piperidine |
| DE102009022894A1 (de) * | 2009-05-27 | 2010-12-02 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Piperidine |
| DE102009022895A1 (de) * | 2009-05-27 | 2010-12-02 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Piperidine |
| US20130190506A1 (en) * | 2010-06-28 | 2013-07-25 | Hetero Research Foundation | Process for olmesartan medoxomil |
| US9266896B2 (en) | 2010-07-22 | 2016-02-23 | Zafgen, Inc. | Tricyclic compounds and methods of making and using same |
| WO2012051318A1 (en) | 2010-10-12 | 2012-04-19 | Zafgen Corporation | Sulphonamide compounds and methods of making and using same |
| WO2012054510A1 (en) * | 2010-10-19 | 2012-04-26 | Comentis, Inc. | Oxadiazole compounds which inhibit beta-secretase activity and methods of use thereof |
| WO2012103333A1 (en) | 2011-01-26 | 2012-08-02 | Zafgen Corporation | Tetrazole compounds and methods of making and using same |
| BR112013028666A2 (pt) | 2011-05-06 | 2017-08-08 | Zafgen Inc | compostos de pirazolo sulfonamida tricícilos e métodos para fazer e usar o mesmo |
| CA2835261C (en) | 2011-05-06 | 2019-06-04 | Zafgen, Inc. | Partially saturated tricyclic compounds and methods of making and using same |
| BR112013028665A2 (pt) | 2011-05-06 | 2016-09-06 | Zafgen Inc | compostos de sulfonamida tricíclicos e métodos para fazer e usar os mesmos |
| JP2015509102A (ja) | 2012-01-18 | 2015-03-26 | ザフゲン，インコーポレイテッド | 三環式スルホン化合物並びにその作製および使用方法 |
| JP6035347B2 (ja) | 2012-01-18 | 2016-11-30 | ザフゲン，インコーポレイテッド | 三環式スルホンアミド化合物ならびにその作製および使用方法 |
| JP2015536981A (ja) | 2012-11-05 | 2015-12-24 | ザフゲン，インコーポレイテッド | 三環式化合物ならびにその製造および使用方法 |
| SG11201503521QA (en) | 2012-11-05 | 2015-06-29 | Zafgen Inc | Methods of treating liver diseases |
| AU2013337288A1 (en) | 2012-11-05 | 2015-05-21 | Zafgen, Inc. | Tricyclic compounds for use in the treatment and/or control of obesity |
| CN103965095A (zh) * | 2013-02-04 | 2014-08-06 | 艾琪康医药科技（上海）有限公司 | 1-r1-3-r2-4-氟哌啶及其衍生物的制备方法 |
| CN104341590A (zh) * | 2013-08-01 | 2015-02-11 | 韩冰 | 一种树枝状高分子化合物及其制备和用途 |
| CN113543852A (zh) | 2019-03-06 | 2021-10-22 | 第一三共株式会社 | 吡咯并吡唑衍生物 |
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| ZA951618B (en) * | 1994-03-04 | 1996-08-27 | Lilly Co Eli | Antithrombotic agents |
| US5767144A (en) * | 1994-08-19 | 1998-06-16 | Abbott Laboratories | Endothelin antagonists |
| PT885215E (pt) * | 1996-02-13 | 2006-08-31 | Abbott Lab | Novos derivados de pirrolidina substituidos com benzo-1,3-dioxolilo e benzofuranilo como antagonistas de endotelina |
| WO1997036873A1 (en) * | 1996-04-03 | 1997-10-09 | Merck & Co., Inc. | Piperidines, pyrrolidines and hexahydro-1h-azepines promote release of growth hormone |
| US6403612B2 (en) | 2000-01-31 | 2002-06-11 | Merck & Co., Inc. | Thrombin receptor antagonists |
| CN1243735C (zh) * | 2001-04-19 | 2006-03-01 | 卫材株式会社 | 2－亚氨基吡咯烷衍生物 |
| CN1283252C (zh) * | 2001-10-15 | 2006-11-08 | 詹森药业有限公司 | 用于减少缺血性损伤的取代的4－苯基－4－(1h－咪唑－2－基)－哌啶衍生物 |
| US7030141B2 (en) * | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| CA2571258A1 (en) | 2004-06-24 | 2006-01-05 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| WO2006012226A2 (en) | 2004-06-24 | 2006-02-02 | Incyte Corporation | N-substituted piperidines and their use as pharmaceuticals |
| JP2008504279A (ja) | 2004-06-24 | 2008-02-14 | インサイト・コーポレイション | アミド化合物およびその医薬としての使用 |
| JP2008509910A (ja) | 2004-08-10 | 2008-04-03 | インサイト・コーポレイション | アミド化合物およびその医薬としての使用 |
| DE102004045796A1 (de) | 2004-09-22 | 2006-03-23 | Merck Patent Gmbh | Arzneimittel enthaltend Carbonylverbindungen sowie deren Verwendung |
| JPWO2006051623A1 (ja) * | 2004-11-09 | 2008-05-29 | エーザイ株式会社 | トロンビン受容体アンタゴニストを有効成分とするくも膜下出血に伴う血管攣縮の治療剤 |
| WO2007038138A2 (en) | 2005-09-21 | 2007-04-05 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| AU2007210018A1 (en) | 2006-01-31 | 2007-08-09 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| US20070213311A1 (en) | 2006-03-02 | 2007-09-13 | Yun-Long Li | Modulators of 11-beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same |
| US20070293529A1 (en) * | 2006-05-01 | 2007-12-20 | Yun-Long Li | Tetrasubstituted ureas as modulators of 11-beta hydroxyl steroid dehydrogenase type 1 |
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- 2008-11-20 EP EP08854224A patent/EP2227466B1/de not_active Not-in-force
- 2008-11-20 DE DE502008003324T patent/DE502008003324D1/de active Active
- 2008-11-20 DK DK08854224.6T patent/DK2227466T3/da active
- 2008-11-20 KR KR1020107014447A patent/KR20100114018A/ko not_active Application Discontinuation
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- 2008-11-20 CN CN2008801260263A patent/CN101932577B/zh not_active Expired - Fee Related
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- 2008-11-25 PA PA20088805201A patent/PA8805201A1/xx unknown
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-
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Also Published As
| Publication number | Publication date |
|---|---|
| JP5450435B2 (ja) | 2014-03-26 |
| CN101932577B (zh) | 2013-07-17 |
| TW200936135A (en) | 2009-09-01 |
| WO2009068214A3 (de) | 2009-08-20 |
| US20090306139A1 (en) | 2009-12-10 |
| DK2227466T3 (da) | 2011-08-08 |
| US8119663B2 (en) | 2012-02-21 |
| EP2227466A2 (de) | 2010-09-15 |
| HK1152311A1 (en) | 2012-02-24 |
| ATE506359T1 (de) | 2011-05-15 |
| PE20091026A1 (es) | 2009-07-26 |
| UY31484A1 (es) | 2009-07-17 |
| AR069417A1 (es) | 2010-01-20 |
| EP2227466B1 (de) | 2011-04-20 |
| US20120214788A1 (en) | 2012-08-23 |
| KR20100114018A (ko) | 2010-10-22 |
| JP2011504889A (ja) | 2011-02-17 |
| WO2009068214A2 (de) | 2009-06-04 |
| PT2227466E (pt) | 2011-07-01 |
| PA8805201A1 (es) | 2010-02-12 |
| CN101932577A (zh) | 2010-12-29 |
| CL2008003473A1 (es) | 2009-08-14 |
| DE502008003324D1 (de) | 2011-06-01 |
| PL2227466T3 (pl) | 2011-09-30 |
| CA2706991A1 (en) | 2009-06-04 |
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