HRP20100696T1 - Hiv inhibirajuci 5-(hidroksimetilen i aminometilen) supstituirani pirimidini - Google Patents
Hiv inhibirajuci 5-(hidroksimetilen i aminometilen) supstituirani pirimidini Download PDFInfo
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- HRP20100696T1 HRP20100696T1 HR20100696T HRP20100696T HRP20100696T1 HR P20100696 T1 HRP20100696 T1 HR P20100696T1 HR 20100696 T HR20100696 T HR 20100696T HR P20100696 T HRP20100696 T HR P20100696T HR P20100696 T1 HRP20100696 T1 HR P20100696T1
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- alkyl
- het
- 6alkyl
- amino
- optionally substituted
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- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 title abstract 2
- 230000002401 inhibitory effect Effects 0.000 title abstract 2
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- -1 cyano, amino Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 241000725303 Human immunodeficiency virus Species 0.000 abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000010076 replication Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two 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
- A61K31/395—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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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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
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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Abstract
Spoj formule njegov stereokemijski izomerni oblik, njegova farmaceutski prihvatljiva adicijska sol, njegov farmaceutski prihvatljiv hidrat ili solvat, njegov N-oksid, naznacen time da svaki R1 nezavisno je vodik; aril; formil; C1-6alkilkarbonil; C1-6alkil; C1-6alkiloksikarbonil; R2, R3, R7 i R8 nezavisno su vodik; hidroksi; halo; C3-7cikloalkil; C1-6alkiloksi; karboksil; C1-6alkiloksikarbonil; cijano; nitro; amino; mono- ili di(C1-6alkil)amino; polihaloC1-6alkil; polihaloC1-6alkiloksi; -C(=O)R10; C1-6alkil po izboru supstituiran sa halo, cijano ili -C(=O)R10; C2-6alkenil po izboru supstituiran sa halo, cijano ili -C(=O)R10; C2-6alkinil po izboru supstituiran sa halo, cijano ili -C(=O)R10;R4 i R9 nezavisno su hidroksi; halo; C3-7cikloalkil; C1-6alkiloksi; karboksil; C1-6alkiloksikarbonil; formil; cijano; nitro; amino; mono- ili di(C1-6alkil)amino; polihaloC1-6alkil; polihaloC1-6alkiloksi; -C(=O)R10; cijano; -S(=O)rR10; -NH-S(=O)rR10; -NHC(=O)H; -C(=O)NHNH2; -NHC(=O)R10; Het; -Y'-Het; C1-12alkil po izboru supstituiran sa halo, cijano, amino, mono- ili di(C1-6alkil)-amino, -C(=O)-R10, Het ili sa C1-6alkiloksi; C2-12alkenil po izboru supstituiran sa halo, cijano, amino, mono- ili di(C1-6alkil)amino, -C(=O)-R10, Het ili sa C1-6alkiloksi; C2-12alkinil po izboru supstituiran sa halo, cijano, amino, mono- i di(C1-6alkil)amino, -C(=O)-R10, Het ili sa C1-6alkiloksi; R5 je C1-6alkil po izboru supstituiran sa Ar ili sa Het; C2-6alkenil po izboru supstituiran sa Ar ili sa Het; C2-6alkinil po izboru supstituiran sa Ar ili sa Het; C3-7cikloalkil; Ar; Het; R6 je H, C1-6alkil, Het; Y je -OR11, -NR12R13;svaki R10 nezavisno je C1-6alkil, amino, mono- ili di(C1-6alkil)amino ili polihalo-C1-6alkil; R11 je vodik ili C1-6alkil po izboru supstituiran sa hidroksi, C1-6alkiloksi, fenilom ili piridilom; R12 je vodik ili C1-6alkil; R13 je vodik ili C1-6alkil; ili R12 i R13 uzeti zajedno sa atomom dusika na koji su supstituirani formiraju pirolidinil; piperidinil; morfolinil; piperazinil; piperazinil po izboru supstituiran sa C1-6alkil ili C1-6alkilkarbonil; imidazolil; X je -NR1-, -O-, -C(=O)-, -CH2-, -CHOH-, -S-, -S(=O)r-;svaki Y' nezavisno je -NR1-, -O-, -C(=O)-, -S-, -S(=O)r-;svaki r nezavisno je 1 ili 2; Het je 5- ili 6-clani potpunosti nezasiceni prsten pri cemu jedan, dva, tri ili cetiri clana prstena su hetero atomi, svaki nezavisno odabran od dusika, kisika i sumpora, i pri cemu su preostali clanovi prstena atomi ugljika; te gdje je moguce, bilo koji clan prstena dusika moze po izboru biti supstituiran sa C1-6alkilom; koji 5- ili 6-clani prsten moze po izboru biti aneliran sa benzenskim, tiofenskim ili piridinskim prstenom; i pri cemu bilo koji atom ugljika u prstenu, ukljucujuci bilo koji ugljik iz po izboru aneliranog benzenskog, tiofenskog ili piridinskog prstena, moze, svaki nezavisno, po izboru biti supstituiran sa supstituentom odabranim od halo, hidroksi, merkapto, cijano, C1-6alkil, hidroksiC1-4alkil, karboksiC1-4alkil, C1-4alkiloksiC1-4alkil, C1-4alkiloksik
Claims (10)
1. Spoj formule
[image]
njegov stereokemijski izomerni oblik, njegova farmaceutski prihvatljiva adicijska sol, njegov farmaceutski prihvatljiv hidrat ili solvat, njegov N-oksid, naznačen time da
svaki R1 nezavisno je vodik; aril; formil; C1-6alkilkarbonil; C1-6alkil;
C1-6alkiloksikarbonil;
R2, R3, R7 i R8 nezavisno su vodik; hidroksi; halo; C3-7cikloalkil; C1-6alkiloksi; karboksil; C1-6alkiloksikarbonil; cijano; nitro; amino; mono- ili di(C1-6alkil)amino; polihaloC1-6alkil; polihaloC1-6alkiloksi; -C(=O)R10; C1-6alkil po izboru supstituiran sa halo, cijano ili -C(=O)R10; C2-6alkenil po izboru supstituiran sa halo, cijano ili -C(=O)R10; C2-6alkinil po izboru supstituiran sa halo, cijano ili -C(=O)R10;
R4 i R9 nezavisno su hidroksi; halo; C3-7cikloalkil; C1-6alkiloksi; karboksil; C1-6alkiloksikarbonil; formil; cijano; nitro; amino; mono- ili di(C1-6alkil)amino; polihaloC1-6alkil; polihaloC1-6alkiloksi; -C(=O)R10; cijano; -S(=O)rR10; -NH-S(=O)rR10; -NHC(=O)H; -C(=O)NHNH2; -NHC(=O)R10; Het; -Y'-Het; C1-12alkil po izboru supstituiran sa halo, cijano, amino, mono- ili di(C1-6alkil)-amino, -C(=O)-R10, Het ili sa C1-6alkiloksi; C2-12alkenil po izboru supstituiran sa halo, cijano, amino, mono- ili di(C1-6alkil)amino, -C(=O)-R10, Het ili sa C1-6alkiloksi; C2-12alkinil po izboru supstituiran sa halo, cijano, amino, mono- i di(C1-6alkil)amino, -C(=O)-R10, Het ili sa C1-6alkiloksi;
R5 je C1-6alkil po izboru supstituiran sa Ar ili sa Het; C2-6alkenil po izboru supstituiran sa Ar ili sa Het; C2-6alkinil po izboru supstituiran sa Ar ili sa Het; C3-7cikloalkil; Ar; Het;
R6 je H, C1-6alkil, Het;
Y je -OR11, -NR12R13;
svaki R10 nezavisno je C1-6alkil, amino, mono- ili di(C1-6alkil)amino ili polihalo-C1-6alkil;
R11 je vodik ili C1-6alkil po izboru supstituiran sa hidroksi, C1-6alkiloksi, fenilom ili piridilom;
R12 je vodik ili C1-6alkil;
R13 je vodik ili C1-6alkil; ili R12 i R13 uzeti zajedno sa atomom dušika na koji su supstituirani formiraju pirolidinil; piperidinil; morfolinil; piperazinil; piperazinil po izboru supstituiran sa C1-6alkil ili C1-6alkilkarbonil; imidazolil;
X je -NR1-, -O-, -C(=O)-, -CH2-, -CHOH-, -S-, -S(=O)r-;
svaki Y' nezavisno je -NR1-, -O-, -C(=O)-, -S-, -S(=O)r-;
svaki r nezavisno je 1 ili 2;
Het je 5- ili 6-člani potpunosti nezasićeni prsten pri čemu jedan, dva, tri ili četiri člana prstena su hetero atomi, svaki nezavisno odabran od dušika, kisika i sumpora, i pri čemu su preostali članovi prstena atomi ugljika; te gdje je moguće, bilo koji član prstena dušika može po izboru biti supstituiran sa C1-6alkilom; koji 5- ili 6-člani prsten može po izboru biti aneliran sa benzenskim, tiofenskim ili piridinskim prstenom; i pri čemu bilo koji atom ugljika u prstenu, uključujući bilo koji ugljik iz po izboru aneliranog benzenskog, tiofenskog ili piridinskog prstena, može, svaki nezavisno, po izboru biti supstituiran sa supstituentom odabranim od halo, hidroksi, merkapto, cijano, C1-6alkil, hidroksiC1-4alkil, karboksiC1-4alkil, C1-4alkiloksiC1-4alkil, C1-4alkiloksikarbonilC1-4alkil, cijanoC1-4alkil, mono- i di(C1-4alkil)aminoC1-4alkil, Het1C1-4alkil, arilC1-4alkil, polihaloC1-4alkil, C3-7cikloalkil, C2-6alkenil, C2-6alkinil, aril-C2-4alkenil, C1-4alkiloksi, -OCONH2, polihaloC1-4alkiloksi, ariloksi, amino, mono- i di-C1-4alkilamino, pirolidinil, piperidinil, morfolinil, piperazinil, 4-C1-6alkilpiperazinil, C1-4alkilkarbonilamino, formil, C1-4alkilkarbonil, C1-4alkiloksi-karbonil, aminokarbonil, mono- i diC1-4alkilaminokarbonil, aril, Het1;
Het1 je piridil, tienil, furanil, oksazolil, izoksazolil, imidazolil, pirazolil, tiazolil, tiadiazolil, oksadiazolil kvinolinil, benzotienil, benzofuranil; koji svaki može biti po izboru supstituiran sa jednim ili dva C1-4alkil radikala;
svaki aril nezavisno je fenil ili fenil supstituiran sa jednim, dva, tri, četiri ili pet supstituenata svaki nezavisno odabran od halo, hidroksi, merkapto, C1-6alkil, C2-6alkenil, C2-6alkinil, hidroksiC1-6alkil, aminoC1-6alkil, mono i di(C1-6alkil)-aminoC1-6alkil, C1-6alkilkarbonil, C3-7cikloalkil, C1-6alkiloksi, fenilC1-6alkiloksi, C1-6alkiloksikarbonil, aminosulfonil, C1-6alkiltio, cijano, nitro, polihaloC1-6alkil, polihaloC1-6alkiloksi, aminokarbonil, fenil, Het i -Y'-Het.
2. Spoj prema zahtjevu 1 naznačen time da je spoj formule
[image]
pri čemu X, Y, R1, R4, R5, R6, R7, R8 i R9 su kako je definirano u zahtjevu 1.
3. Spoj prema zahtjevima 1 ili 2 naznačen time da R1 je vodik.
4. Spoj prema zahtjevima 1 ili 3 naznačen time da R2, R3, R7 i R8 nezavisno su vodik; hidroksi; halo; C1-6alkil; C1-6alkiloksi; cijano; amino; mono- ili di(C1-6alkil)amino; polihaloC1-6alkil.
5. Spoj prema zahtjevima 1 do 4 naznačen time da R4 i R9 nezavisno su cijano; C1-6alkil supstituiran sa cijano; C2-6alkenil supstituiran sa cijano.
6. Spoj prema bilo kojem od zahtjeva 1 do 5 naznačen time da R5 je C1-6alkil supstituiran sa Ar ili sa Het, C2-6alkenil, C2-6alkinil po izboru supstituiran sa Het, C3-7cikloalkil, Ar, Het;
R6 je H, C1-6alkil, Het;
Y je OR11, NR12R13;
R11 je vodik ili C1-6alkil po izboru supstituiran sa hidroksi, C1-6alkiloksi, fenilom ili piridilom;
R12 je vodik ili C1-6alkil;
R13 je vodik ili C1-6alkil; ili R12 i R13 uzeti zajedno sa atomom dušika na koji su supstituirani formiraju imidazolil.
7. Spoj prema bilo kojem od zahtjeva 1 do 5 naznačen time da R5 je C2-6alkenil, C2-6alkinil supstituiran sa Het, Ar, Het;
R6 je H, C1-6alkil, Het;
Y je OR11, NR12R13;
R11 je vodik ili C1-6alkil po izboru supstituiran sa hidroksi, C1-6alkiloksi;
R12 je vodik ili C1-6alkil;
R13 je vodik.
8. Spoj prema bilo kojem od zahtjeva 1 do 7 naznačen time da svaki Het nezavisno je piridil, tienil, tiazolil, furanil, svaki od kojih može biti po izboru supstituiran sa radikalom odabranim od C1-6alkil.
9. Spoj prema bilo kojem od zahtjeva 1 do 8 naznačen time da svaki aril nezavisno može biti fenil po izboru supstituiran sa C1-6alkil, amino, mono- ili diC1-6alkil-amino, C1-6alkiloksi, aminosulfonil, Het, potonji je posebice tiadiazolil.
10. Farmaceutski pripravak naznačen time da sadrži farmaceutski prihvatljiv nosač i kao aktivnu tvar terapeutski učinkovitu količinu spoja prema bilo kojem od zahtjeva 1 do 9.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06112045 | 2006-03-30 | ||
| PCT/EP2007/053113 WO2007113256A1 (en) | 2006-03-30 | 2007-03-30 | Hiv inhibiting 5-(hydroxymethylene and aminomethylene) substituted pyrimidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100696T1 true HRP20100696T1 (hr) | 2011-01-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| HR20100696T HRP20100696T1 (hr) | 2006-03-30 | 2010-12-17 | Hiv inhibirajuci 5-(hidroksimetilen i aminometilen) supstituirani pirimidini |
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| US (1) | US8163745B2 (hr) |
| EP (1) | EP2004641B1 (hr) |
| JP (1) | JP5070278B2 (hr) |
| KR (1) | KR20080104040A (hr) |
| CN (1) | CN101410394B (hr) |
| AT (1) | ATE482953T1 (hr) |
| AU (1) | AU2007233739B2 (hr) |
| BR (1) | BRPI0709266B8 (hr) |
| CA (1) | CA2645959C (hr) |
| DE (1) | DE602007009508D1 (hr) |
| DK (1) | DK2004641T3 (hr) |
| ES (1) | ES2353725T3 (hr) |
| HR (1) | HRP20100696T1 (hr) |
| IL (1) | IL193725A (hr) |
| MX (1) | MX2008012577A (hr) |
| RU (1) | RU2452737C2 (hr) |
| SI (1) | SI2004641T1 (hr) |
| WO (1) | WO2007113256A1 (hr) |
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| CN101119976B (zh) * | 2005-02-18 | 2010-12-22 | 泰博特克药品有限公司 | 抑制hiv的2-(4-氰基苯氨基)嘧啶氧化物衍生物 |
| JP5185283B2 (ja) * | 2006-12-29 | 2013-04-17 | テイボテク・フアーマシユーチカルズ | Ｈｉｖ阻害６−置換ピリミジン |
| SI2300013T1 (en) | 2008-05-21 | 2018-03-30 | Adriad Pharmacaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| US11351168B1 (en) | 2008-06-27 | 2022-06-07 | Celgene Car Llc | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| ES2711249T3 (es) | 2008-06-27 | 2019-04-30 | Celgene Car Llc | Compuestos de heteroarilo y usos de los mismos |
| US8338439B2 (en) | 2008-06-27 | 2012-12-25 | Celgene Avilomics Research, Inc. | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| KR101705158B1 (ko) | 2009-05-05 | 2017-02-09 | 다나-파버 캔서 인스티튜트 인크. | Ｅｇｆｒ 억제제 및 질환 치료방법 |
| KR20130099040A (ko) | 2010-08-10 | 2013-09-05 | 셀진 아빌로믹스 리서치, 인코포레이티드 | Ｂｔｋ 억제제의 베실레이트 염 |
| NZ609957A (en) | 2010-11-01 | 2015-08-28 | Celgene Avilomics Res Inc | Heterocyclic compounds and uses thereof |
| ES2635713T3 (es) | 2010-11-01 | 2017-10-04 | Celgene Car Llc | Compuestos de heteroarilo y usos de los mismos |
| JP5957003B2 (ja) | 2010-11-10 | 2016-07-27 | セルジーン アヴィロミクス リサーチ， インコーポレイテッド | 変異体選択的ｅｇｆｒ阻害剤およびその使用 |
| EA201391626A1 (ru) | 2011-05-04 | 2014-03-31 | Ариад Фармасьютикалз, Инк. | Соединения для ингибирования клеточной пролиферации в egfr-стимулированных типах рака |
| CN102260215A (zh) * | 2011-05-13 | 2011-11-30 | 复旦大学 | 一种二芳基嘧啶类衍生物及其制备方法和用途 |
| JP2014532658A (ja) | 2011-10-28 | 2014-12-08 | セルジーン アヴィロミクス リサーチ， インコーポレイテッド | ブルトン型チロシンキナーゼ疾患または障害を治療する方法 |
| SG10201700799WA (en) | 2012-03-15 | 2017-02-27 | Celgene Avilomics Res Inc | Salts of an epidermal growth factor receptor kinase inhibitor |
| ES2880109T3 (es) | 2012-03-15 | 2021-11-23 | Celgene Car Llc | Formas sólidas de un inhibidor de la cinasa del receptor del factor de crecimiento epidérmico |
| JP6469567B2 (ja) | 2012-05-05 | 2019-02-13 | アリアド・ファーマシューティカルズ・インコーポレイテッド | Ｅｇｆｒ発動性がんの細胞増殖阻害用化合物 |
| EP2935226A4 (en) | 2012-12-21 | 2016-11-02 | Celgene Avilomics Res Inc | HETEROARYL COMPOUNDS AND USES THEREOF |
| WO2014124230A2 (en) | 2013-02-08 | 2014-08-14 | Celgene Avilomics Research, Inc. | Erk inhibitors and uses thereof |
| US9611283B1 (en) | 2013-04-10 | 2017-04-04 | Ariad Pharmaceuticals, Inc. | Methods for inhibiting cell proliferation in ALK-driven cancers |
| US9492471B2 (en) | 2013-08-27 | 2016-11-15 | Celgene Avilomics Research, Inc. | Methods of treating a disease or disorder associated with Bruton'S Tyrosine Kinase |
| CN103483272B (zh) * | 2013-09-29 | 2015-10-21 | 山东大学 | 间二芳烃-多取代嘧啶类衍生物及其制备方法与应用 |
| RU2547844C1 (ru) * | 2013-10-29 | 2015-04-10 | Федеральное государственное бюджетное учреждение науки Институт органического синтеза им. И.Я. Постовского Уральского отделения Российской академии наук | Способ получения 5-(гет)арил-4-(2-тиенил)-2-(тио)морфолилпиримидина |
| US9415049B2 (en) | 2013-12-20 | 2016-08-16 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| EP3179858B1 (en) | 2014-08-13 | 2019-05-15 | Celgene Car Llc | Forms and compositions of an erk inhibitor |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459731A (en) | 1966-12-16 | 1969-08-05 | Corn Products Co | Cyclodextrin polyethers and their production |
| NZ322907A (en) | 1995-11-23 | 1998-12-23 | Janssen Pharmaceutica Nv | Solid mixtures of cyclodextrins prepared via melt-extrusion |
| SK287996B6 (sk) | 1998-03-27 | 2012-09-03 | Janssen Pharmaceutica N. V. | Pyrimide compound, pharmaceutical composition the compound is comprised, method for preparation thereof, combination and product containing the composition and use of the pyrimide compound |
| HU230394B1 (hu) | 1998-11-10 | 2016-04-28 | Janssen Pharmaceutica N.V. | HIV-vírus szaporodását gátló pirimidin-származékok |
| EP1282606B1 (en) * | 2000-05-08 | 2015-04-22 | Janssen Pharmaceutica NV | Hiv replication inhibiting pyrimidines and triazines |
| JO3429B1 (ar) | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | مشتقات برميدينات مثبطة فيروس الايدز |
| BRPI0406809A (pt) * | 2003-01-17 | 2005-12-27 | Warner Lambert Co | Heterociclos substituìdos de 2-aminopiridina como inibidores da proliferação celular |
| MXPA05008364A (es) * | 2003-02-07 | 2005-11-04 | Janssen Pharmaceutica Nv | Derivados de pirimidina para la prevencion de una infeccion por vih. |
| RU2403244C2 (ru) * | 2004-09-30 | 2010-11-10 | Тиботек Фармасьютикалз Лтд. | Вич-ингибирующие 5-карбо- или гетероциклические замещенные пиримидины |
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- 2007-03-30 KR KR1020087023894A patent/KR20080104040A/ko not_active Application Discontinuation
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- 2007-03-30 CN CN2007800110048A patent/CN101410394B/zh active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| CN101410394A (zh) | 2009-04-15 |
| EP2004641B1 (en) | 2010-09-29 |
| DE602007009508D1 (de) | 2010-11-11 |
| BRPI0709266A2 (pt) | 2011-06-28 |
| BRPI0709266B8 (pt) | 2021-05-25 |
| ATE482953T1 (de) | 2010-10-15 |
| RU2008143018A (ru) | 2010-05-10 |
| RU2452737C2 (ru) | 2012-06-10 |
| CN101410394B (zh) | 2012-02-08 |
| WO2007113256A1 (en) | 2007-10-11 |
| CA2645959C (en) | 2016-05-17 |
| DK2004641T3 (da) | 2011-01-24 |
| AU2007233739A1 (en) | 2007-10-11 |
| US8163745B2 (en) | 2012-04-24 |
| BRPI0709266B1 (pt) | 2020-09-29 |
| JP5070278B2 (ja) | 2012-11-07 |
| AU2007233739B2 (en) | 2013-01-17 |
| MX2008012577A (es) | 2008-10-10 |
| ES2353725T3 (es) | 2011-03-04 |
| IL193725A0 (en) | 2009-05-04 |
| CA2645959A1 (en) | 2007-10-11 |
| EP2004641A1 (en) | 2008-12-24 |
| SI2004641T1 (sl) | 2011-02-28 |
| JP2009531395A (ja) | 2009-09-03 |
| US20100234375A1 (en) | 2010-09-16 |
| IL193725A (en) | 2014-11-30 |
| KR20080104040A (ko) | 2008-11-28 |
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