HRP20211336T1 - Difluorometil-aminopiridini i difluorometil-aminopirimidini - Google Patents
Difluorometil-aminopiridini i difluorometil-aminopirimidini Download PDFInfo
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- HRP20211336T1 HRP20211336T1 HRP20211336TT HRP20211336T HRP20211336T1 HR P20211336 T1 HRP20211336 T1 HR P20211336T1 HR P20211336T T HRP20211336T T HR P20211336TT HR P20211336 T HRP20211336 T HR P20211336T HR P20211336 T1 HRP20211336 T1 HR P20211336T1
- Authority
- HR
- Croatia
- Prior art keywords
- difluoromethyl
- amine
- triazin
- pyridin
- azabicyclo
- Prior art date
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- ANDIJFDISUBYSA-UHFFFAOYSA-N 3-(difluoromethyl)pyridin-2-amine Chemical class NC1=NC=CC=C1C(F)F ANDIJFDISUBYSA-UHFFFAOYSA-N 0.000 title 1
- SUVMSNKJNMLRRL-UHFFFAOYSA-N 4-(difluoromethyl)pyrimidin-2-amine Chemical class NC1=NC=CC(C(F)F)=N1 SUVMSNKJNMLRRL-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 3
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Classifications
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
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- 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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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D405/00—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
- C07D405/14—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 three or more hetero rings
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- C07—ORGANIC CHEMISTRY
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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
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- C07D—HETEROCYCLIC COMPOUNDS
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Claims (15)
1. Spoj formule (I),
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gdje
X1, X2 i X3, neovisno jedan o drugome, su N ili CH; pod uvjetom da su najmanje dva od X1, X2 i X3 N;
Y je N ili CH;
R1 i R2 su neovisno jedno o drugome
(i) morfolinil formule (II)
[image]
gdje strelica označava vezu u formuli (I); i
gdje su R3 i R4, neovisno jedan o drugome, H, C1-C3alkil po izboru supstituiran s jednim ili dva od OH, C1-C2fluoroalkil, C1-C2alkoksi, C1-C2alkoksiC1-C3alkil, CN ili C(O)O-C1-C2alkil; ili R3 i R4 zajedno oblikuju dvovalentni ostatak -R5R6- odabran iz -CH2-O-CH2-, -CH2-NH-CH2- ili C1‑C3alkilena izborno supstituiranog s od 1 do 4 F, ili bilo koju od struktura
[image]
gdje strelice označavaju veze u formuli (II); ili
(ii) zasićeni 5- do 6-člani heterociklički prsten Z koji sadrži 1 do 2 heteroatoma neovisno odabrana od N, O i S, po izboru supstituiran s od 1 do 3 R9; pri čemu je R9, nezavisno pri svakom pojavljivanju, halogen, -OH, C1-C3alkil, CH2OH, CH2CH2OH, CH2F, CHF2, CF3, CH2CF3, C1-C2alkoksi, C1-C2alkoksiC1-C3alkil, C3-C6cikloalkil, =O, -NH2, NHCH3 ili N(CH3)2; ili dva R9 supstituenta zajedno oblikuju dvovalentni ostatak -R10R11- odabran od -CH2-O-CH2-, -O-CH2CH2-O- ili C1-C3alkilena izborno supstituiranog s od 1 do 4 F;
pod uvjetom da je najmanje jedan od R1 i R2 morfolinil formule II;
i njegovi tautomeri, solvati i farmaceutski prihvatljive soli.
2. Spoj formule (I) sukladno patentnom zahtjevu 1, gdje su X1, X2 i X3 N; i njegovi tautomeri, solvati i farmaceutski prihvatljive soli.
3. Spoj formule (I) sukladno patentnom zahtjevu 1 ili patentnom zahtjevu 2, gdje su navedeni R1 i navedeni R2,neovisno jedan o drugome, odabrani iz
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4. Spoj formule (I) sukladno patentnom zahtjevu 3, gdje su R1 i R2 neovisno jedan o drugome, odabrani iz
[image]
[image]
5. Spoj formule (I) sukladno patentnom zahtjevu 1, pri čemu je navedeni spoj odabran iz
4-(difluorometil)-5-(4,6-dimorfolino-1,3,5-triazin-2-il)piridin-2-amina;
4-(difluorometil)-5-(4,6-dimorfolino-1,3,5-triazin-2-il)pirimidin-2-amina;
5-(4-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-6-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-1,3,5-triazin-2-il)-4-(difluorometil)piridin-2-amina;
5-(4-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-6-morfolino-1,3,5-triazin-2-il)-4-(difluorometil)piridin-2-amina;
5-(4-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-6-morfolino-1,3,5-triazin-2-il)-4-(difluorometil)pirimidin-2-amina;
5-(4,6-bis((S)-3-metilmorfolino)-1,3,5-triazin-2-il)-4-(difluorometil)piridin-2-amina;
5-(4,6-bis((S)-3-metilmorfolino)-1,3,5-triazin-2-il)-4-(difluorometil)pirimidin-2-amina;
(S)-4-(difluorometil)-5-(4-(3-metilmorfolino)-6-morfolino-1,3,5-triazin-2-il)piridin-2-amina;
(S)-4-(difluorometil)-5-(4-(3-metilmorfolino)-6-morfolino-1,3,5-triazin-2-il)pirimidin-2-amina;
5-(4-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-6-((S)-3-metilmorfolino)-1,3,5-triazin-2-il)-4-(difluorometil)piridin-2-amina;
5-(4-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-6-((S)-3-metilmorfolino)-1,3,5-triazin-2-il)-4-(difluorometil)pirimidin-2-amina;
4-(difluorometil)-5-(4-morfolino-6-(piperazin-1-il)-1,3,5-triazin-2-il)piridin-2-amina;
4-(difluorometil)-5-(4-morfolino-6-(piperazin-1-il)-1,3,5-triazin-2-il)pirimidin-2-amina;
(S)-4-(difluorometil)-5-(4-(3-metilmorfolino)-6-(piperazin-1-il)-1,3,5-triazin-2-il)piridin-2-amina;
(S)-4-(difluorometil)-5-(4-(3-metilmorfolino)-6-(piperazin-1-il)-1,3,5-triazin-2-il)pirimidin-2-amina;
4-(difluorometil)-5-(2,6-dimorfolinopirimidin-4-il)piridin-2-amina;
4'-(difluorometil)-2,6-dimorfolino-[4,5'-bipirimidin]-2'-amina;
4-(difluorometil)-5-(4,6-dimorfolinopirimidin-2-il)piridin-2-amina;
4'-(difluorometil)-4,6-dimorfolino-[2,5'-bipirimidin]-2'-amina;
4-(difluorometil)-5-(4-morfolino-6-tiomorfolino-1,3,5-triazin-2-il)piridin-2-amina;
4-(difluorometil)-5-(4-morfolino-6-tiomorfolino-1,3,5-triazin-2-il)pirimidin-2-amina;
5-(6-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-2-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)pirimidin-4-il)-4-(difluorometil)piridin-2-amina;
5-(2-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-6-morfolinopirimidin-4-il)-4-(difluorometil)piridin-2-amina;
2-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-4'-(difluorometil)-6-morfolino-[4,5'-bipirimidin]-2'-amina;
5-(2,6-bis((S)-3-metilmorfolino)pirimidin-4-il)-4-(difluorometil)piridin-2-amina;
4'-(difluorometil)-2,6-bis((S)-3-metilmorfolino)-[4,5'-bipirimidin]-2'-amina;
(S)-4-(difluorometil)-5-(6-(3-metilmorfolino)-2-morfolinopirimidin-4-il)piridin-2-amina;
(S)-4’-(difluorometil)-6-(3-metilmorfolino)-2-morfolino-[4,5'-bipirimidin]-2'-amina;
5-(4-(8-oksa-3-azabiciklo[3.2.1]oktan-3-il)-6-(8-oksa-3-azabiciklo[3.2.1]oktan-3-il)-1,3,5-triazin-2-il)-4-(difluorometil)piridin-2-amina;
5-[4,6-bis(2,2-dimetilmorfolin-4-il)-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
(S)-4-(difluorometil)-5-(2-(3-metilmorfolino)-6-morfolinopirimidin-4-il)piridin-2-amina;
(S)-4’-(difluorometil)-2-(3-metilmorfolino)-6-morfolino-[4,5'-bipirimidin]-2'-amina;
4-(difluorometil)-5-[4-[(2S,6R)-2,6-dimetilmorfolin-4-il]-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
5-[4,6-bis[(2R,6S)-2,6-dimetilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
4-[4-[6-amino-4-(difluorometil)-3-piridil]-6-morfolino-1,3,5-triazin-2-il]morfolin-3-ona;
4-[4-[2-amino-4-(difluorometil)pirimidin-5-il]-6-morfolino-1,3,5-triazin-2-il]morfolin-3-ona;
5-[4,6-bis(3,7-dioksa-9-azabiciklo[3.3.1]nonan-9-il)-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
4-(difluorometil)-5-[4-(3,7-dioksa-9-azabiciklo[3.3.1]nonan-9-il)-6-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-1,3,5-triazin-2-il]piridin-2-amina;
5-[4,6-bis(3,3-dimetilmorfolin-4-il)-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
5-[4,6-bis[(3R,5S)-3,5-dimetilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
5-[4,6-bis[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
4-(difluorometil)-5-[4-(3,3-dimetilmorfolin-4-il)-6-morfolino-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3R,5S)-3,5-dimetilmorfolin-4-il]-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-(3,3-dimetilmorfolin-4-il)-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3R)-3-(metoksimetil)morfolin-4-il]-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-(3,7-dioksa-9-azabiciklo[3.3.1]nonan-9-il)-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
(4S,5R)-3-[4-[2-amino-4-(difluorometil)pirimidin-5-il]-6-morfolino-1,3,5-triazin-2-il]-4-(hidroksimetil)-5-metil-oksazolidin-2-ona;
(4S,5R)-3-[6-[2-amino-4-(difluorometil)pirimidin-5-il]-2-morfolino-pirimidin-4-il]-4-(hidroksimetil)-5-metil-oksazolidin-2-ona;
4-(difluorometil)-5-[4-[(3R)-3-metilmorfolin-4-il]-6-(3-oksa-6-azabiciklo[3.1.1]heptan-6-il)-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3R)-3-metilmorfolin-4-il]-6-(6-oksa-3-azabiciklo[3.1.1]heptan-3-il)-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3R)-3-metilmorfolin-4-il]-6-[(1R,4R)-2-oksa-5-azabiciklo[2.2.1]heptan-5-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3R)-3-metilmorfolin-4-il]-6-[(1S,4S)-2-oksa-5-azabiciklo[2.2.1]heptan-5-il]-1,3,5-triazin-2-il]piridin-2-amina;
5-[4,6-bis[(3R)-3-etilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
5-[4,6-bis(8-oksa-5-azaspiro[3,5]nonan-5-il)-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
5-[4,6-bis[(3R)-3-izopropilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
5-[4-[(3aR,6aS)-1,3,3a,4,6,6a-heksahidrofuro[3,4-c]pirol-5-il]-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
5-[4-[(4aS,7aR)-2,3,4a,5,7,7a-heksahidro-[1,4]dioksino[2,3-c]pirol-6-il]-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
4-(difluorometil)-5-[4-(4,4-difluoro-1-piperidil)-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3R)-3-metilmorfolin-4-il]-6-(2-oksa-7-azaspiro[3.5]nonan-7-il)-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-(3,3-dimetilmorfolin-4-il)-6-[(3R,5S)-3,5-dimetilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-(3,3-dimetilmorfolin-4-il)-6-[(3R)-3-(metoksimetil)morfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
[(3R)-4-[4-[6-amino-4-(difluorometil)-3-piridil]-6-(3,3-dimetilmorfolin-4-il)-1,3,5-triazin-2-il]morfolin-3-il]metanola;
4-(difluorometil)-5-[4-(3,3-dimetilmorfolin-4-il)-6-(3,7-dioksa-9-azabiciklo[3.3.1]nonan-9-il)-1,3,5-triazin-2-il]piridin-2-amina;
5-[4-(4-ciklopropilpiperazin-1-il)-6-(3,3-dimetilmorfolin-4-il)-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
4-(difluorometil)-5-[4-(3,3-dimetilmorfolin-4-il)-6-[4-(2-metoksietil)piperazin-1-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-(3,3-dimetilmorfolin-4-il)-6-(1,1-diokso-1,4-tiazinan-4-il)-1,3,5-triazin-2-il]piridin-2-amina;
[(3R)-4-[4-[6-amino-4-(difluorometil)-3-piridil]-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]morfolin-3-il]metanola;
4-(difluorometil)-5-[4-[(3R,5R)-3,5-dimetilmorfolin-4-il]-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3S,5S)-3,5-dimetilmorfolin-4-il]-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-morfolino-6-(3-oksa-9-azabiciklo[3.3.1]nonan-9-il)-1,3,5-triazin-2-il]piridin-2-amina;
5-[4,6-bis(3-oksa-9-azabiciklo[3.3.1]nonan-9-il)-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
5-[4-[6-amino-4-(difluorometil)-3-piridil]-6-(3,7-dioksa-9-azabiciklo[3.3.1]nonan-9-il)-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
4-(difluorometil)-5-[4-[(3R)-3-metilmorfolin-4-il]-6-(4-morfolino-1-piperidil)-1,3,5-triazin-2-il]piridin-2-amina;
5-[4-(4-ciklopropilpiperazin-1-il)-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
5-[4-(4-ciklopropilpiperazin-1-il)-6-[(3S,5R)-3,5-dimetilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
4-(difluorometil)-5-[4-[4-(2-metoksietil)piperazin-1-il]-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3S,5R)-3,5-dimetilmorfolin-4-il]-6-[4-(2-metoksietil)piperazin-1-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-(1,1-diokso-1,4-tiazinan-4-il)-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3S,5R)-3,5-dimetilmorfolin-4-il]-6-(1,1-diokso-1,4-tiazinan-4-il)-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3R,5S)-3,5-dimetilmorfolin-4-il]-6-(3,7-dioksa-9-azabiciklo[3.3.1]nonan-9-il)-1,3,5-triazin-2-il]piridin-2-amina;
3-[4-[6-amino-4-(difluorometil)-3-piridil]-6-[(3R,5S)-3,5-dimetilmorfolin-4-il]-1,3,5-triazin-2-il]oksazolidin-2-ona;
5-(4-((1R,2R,4S,5S)-7-oksa-9-azatriciklo[3.3.1.02,4]nonan-9-il)-6-((2R,4S)-7-oksa-9-azatriciklo[3.3.1.02,4]nonan-9-il)-1,3,5-triazin-2-il)-4-(difluorometil)piridin-2-amina;
5-[4,6-bis(6,6-difluoro-3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
5-[4,6-bis(6,7-difluoro-3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-1,3,5-triazin-2-il]-4-(difluorometil))piridin-2-amina;
5-[4-(6-amino-3-piridil)-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina
6. Spoj formule (I) sukladno patentnom zahtjevu 5, pri čemu je navedeni spoj odabran iz skupine koju čine
- 4-(difluorometil)-5-(4,6-dimorfolino-1,3,5-triazin-2-il)pirimidin-2-amin;
- 5-(4-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-6-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-1,3,5-triazin-2-il)-4-(difluorometil)piridin-2-amin;
- 5-(4-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-6-morfolino-1,3,5-triazin-2-il)-4-(difluorometil)piridin-2-amin;
- 5-(4,6-bis((S)-3-metilmorfolino)-1,3,5-triazin-2-il)-4-(difluorometil)pirimidin-2-amin;
- (S)-4-(difluorometil)-5-(4-(3-metilmorfolino)-6-morfolino-1,3,5-triazin-2-il)piridin-2-amin;
- 4-(difluorometil)-5-(4-morfolino-6-(piperazin-1-il)-1,3,5-triazin-2-il)pirimidin-2-amin;
- 4-(difluorometil)-5-(4,6-dimorfolino-1,3,5-triazin-2-il)piridin-2-amin; i
- (S)-4-(difluorometil)-5-(4-(3-metilmorfolino)-6-morfolino-1,3,5-triazin-2-il)pirimidin-2-amin;
i njihovi tautomeri, solvati i farmaceutski prihvatljive soli
7. Spoj formule (I) sukladno patentnom zahtjevu 6, pri čemu je navedeno Spoj odabrano od,
- 4-(difluorometil)-5-(4,6-dimorfolino-1,3,5-triazin-2-il)pirimidin-2-amina;
- 5-(4-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-6-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-1,3,5-triazin-2-il)-4-(difluorometil)piridin-2-amina;
- (S)-4-(difluorometil)-5-(4-(3-metilmorfolino)-6-morfolino-1,3,5-triazin-2-il)piridin-2-amina;
i njihovih tautomera, solvata i farmaceutski prihvatljivih soli.
8. Spoj formule (I) sukladno patentnom zahtjevu 5, pri čemu je navedeni spoj odabran iz
4-[4-[6-amino-4-(difluorometil)-3-piridil]-6-morfolino-1,3,5-triazin-2-il]morfolin-3-ona;
4-[4-[2-amino-4-(difluorometil)pirimidin-5-il]-6-morfolino-1,3,5-triazin-2-il]morfolin-3-ona;
5-[4,6-bis(3,7-dioksa-9-azabiciklo[3.3.1]nonan-9-il)-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
4-(difluorometil)-5-[4-(3,7-dioksa-9-azabiciklo[3.3.1]nonan-9-il)-6-(3-oksa-8-azabiciklo[3.2.1]oktan-8-il)-1,3,5-triazin-2-il]piridin-2-amina;
5-[4,6-bis(3,3-dimetilmorfolin-4-il)-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
5-[4,6-bis[(3R,5S)-3,5-dimetilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
5-[4,6-bis[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]-4-(difluorometil)piridin-2-amina;
4-(difluorometil)-5-[4-(3,3-dimetilmorfolin-4-il)-6-morfolino-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3R,5S)-3,5-dimetilmorfolin-4-il]-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-(3,3-dimetilmorfolin-4-il)-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-[(3R)-3-(metoksimetil)morfolin-4-il]-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
4-(difluorometil)-5-[4-(3,7-dioksa-9-azabiciklo[3.3.1]nonan-9-il)-6-[(3R)-3-metilmorfolin-4-il]-1,3,5-triazin-2-il]piridin-2-amina;
(4S,5R)-3-[4-[2-amino-4-(difluorometil)pirimidin-5-il]-6-morfolino-1,3,5-triazin-2-il]-4-(hidroksimetil)-5-metil-oksazolidin-2-ona;
9. Spoj formule (I) sukladno bilo kojem od patentnih zahtjeva od 1 do 4, gdje su R1 i R2, nezavisno jedan o drugome, morfolinil formule (II).
10. Spoj formule (I) sukladno patentnom zahtjevu 9, gdje je R1 jednak R2.
11. Spoj formule (I) sukladno patentnom zahtjevu 9, gdje R1 nije jednak R2.
12. Spoj formule (I) sukladno bilo kom od patentnih zahtjeva od 1 do 4, gdje su R1 i R2, nezavisno jedan o drugome, morfolinil formule (II) i navedeni zasićeni 5- do 6-člani heterocikličku prsten Z.
13. Spoj formule (I) sukladno patentnom zahtjevu 12, gdje je navedeni 5- do 6-člani heterociklički prsten Z odabran od
[image]
14. Farmaceutski pripravak koji sadrži spoj formule (I) sukladno bilo kojem od patentnih zahtjeva od 1 do 13 i farmaceutski prihvatljiv nosač.
15. Spoj formule (I) sukladno bilo kojem od patentnih zahtjeva od 1 do 13 za uporabu u postupku prevencije ili liječenja bolesti ili poremećaja moduliranog s PI3K i/ili mTOR i/ili PIKK, koji obuhvaća primjenu učinkovite količine navedenog spoja formule (I) sisavcu kojem je takva prevencija ili liječenje potrebno, pri čemu je navedena bolest ili poremećaj hiperproliferativni poremećaj.
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EP15791315.3A EP3218358B1 (en) | 2014-11-11 | 2015-11-10 | Difluoromethyl-aminopyridines and difluoromethyl-aminopyrimidines |
PCT/EP2015/076192 WO2016075130A1 (en) | 2014-11-11 | 2015-11-10 | Difluoromethyl-aminopyridines and difluoromethyl-aminopyrimidines |
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EP (1) | EP3218358B1 (hr) |
JP (1) | JP6689843B2 (hr) |
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RS (1) | RS62289B1 (hr) |
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GB201402431D0 (en) | 2014-02-12 | 2014-03-26 | Karus Therapeutics Ltd | Compounds |
WO2016130501A1 (en) | 2015-02-09 | 2016-08-18 | Incyte Corporation | Aza-heteroaryl compounds as pi3k-gamma inhibitors |
GB201514758D0 (en) * | 2015-08-19 | 2015-09-30 | Karus Therapeutics Ltd | Formulation |
EP4086259A1 (en) | 2015-11-06 | 2022-11-09 | Incyte Corporation | Heterocyclic compounds as pi3k-gamma inhibitors |
MA54567A (fr) * | 2016-01-05 | 2021-10-27 | Incyte Corp | Pyridine et composés de pyridimine en tant qu'inhibiteurs de pi3k-gamma |
US10993947B2 (en) | 2016-05-18 | 2021-05-04 | Torqur | Treatment of skin lesions |
RU2765868C2 (ru) * | 2016-05-18 | 2022-02-04 | Торкур АГ | Лечение неврологических расстройств |
AU2017265384B2 (en) * | 2016-05-18 | 2023-02-23 | The Trustees Of The University Of Pennsylvania | Treatment of skin lesions |
AR108875A1 (es) | 2016-06-24 | 2018-10-03 | Incyte Corp | COMPUESTOS HETEROCÍCLICOS COMO INHIBIDORES DE PI3K-g |
CN107266422A (zh) * | 2017-06-12 | 2017-10-20 | 西安交通大学 | 2‑(5‑嘧啶基)‑4‑吗啉基‑6‑取代均三嗪类化合物及其盐、制备方法和应用 |
MX2020003862A (es) | 2017-10-18 | 2020-08-13 | Incyte Corp | Derivados condensados de imidazol sustituidos por grupos hidroxi terciarios como inhibidores de fosfoinositido 3-cinasas gamma (pi3k-gamma). |
CN109810100B (zh) * | 2017-11-21 | 2022-03-11 | 中国药科大学 | 含有苯并呋喃的parp-1和pi3k双靶点抑制剂 |
RU2020115351A (ru) | 2017-11-23 | 2021-12-23 | Пикур Терапьютикс Аг | Лечение кожных заболеваний |
WO2020030708A1 (en) | 2018-08-07 | 2020-02-13 | Piqur Therapeutics Ag | Treatment of squamous cell carcinoma |
DK3847175T3 (da) | 2018-09-05 | 2024-03-18 | Incyte Corp | Krystallinske former af en phosphoinositid-3-kinase- (pi3k) inhibitor |
CN113906026A (zh) * | 2019-06-06 | 2022-01-07 | 北京泰德制药股份有限公司 | 作为atr激酶抑制剂的2,4,6-三取代的嘧啶化合物 |
CN111039874B (zh) * | 2019-12-13 | 2022-11-04 | 南开大学 | 一种2-胺基-4-甲基嘧啶化合物的零废水制备方法 |
KR20210158019A (ko) | 2020-06-23 | 2021-12-30 | 주식회사 온코빅스 | 포스파티딜이노시톨 3-키나제(pi3k) 억제제로써 pten 과오종 증후군에 의한 종양 세포의 성장 또는 증식을 억제하는데 유용한 신규한 피리미딘 유도체 및 이의 약제학적으로 허용가능한 염, 및 이를 유효성분으로 함유하는 약제학적 조성물 |
WO2022214701A1 (en) * | 2021-04-09 | 2022-10-13 | Universität Basel | Triazine derivative as covalent inhibitors of pi3k |
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AU2006221285B2 (en) * | 2005-03-11 | 2011-03-31 | Zenyaku Kogyo Kabushikikaisha | Immunosuppressive agent and anti-tumor agent comprising heterocyclic compound as active ingredient |
JO2660B1 (en) | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
EA200901065A1 (ru) * | 2007-02-06 | 2010-02-26 | Новартис Аг | Ингибиторы pi 3-киназы и способы их применения |
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