HRP20110621T2 - SPOJEVI PIRIDO[2,3-d]PIRIMIDINONA I NJIHOVA UPOTREBA KAO INHIBITORI PI3 - Google Patents
SPOJEVI PIRIDO[2,3-d]PIRIMIDINONA I NJIHOVA UPOTREBA KAO INHIBITORI PI3 Download PDFInfo
- Publication number
- HRP20110621T2 HRP20110621T2 HRP20110621TT HRP20110621T HRP20110621T2 HR P20110621 T2 HRP20110621 T2 HR P20110621T2 HR P20110621T T HRP20110621T T HR P20110621TT HR P20110621 T HRP20110621 T HR P20110621T HR P20110621 T2 HRP20110621 T2 HR P20110621T2
- Authority
- HR
- Croatia
- Prior art keywords
- amino
- methyl
- pyrimidin
- cyclohexyl
- trans
- Prior art date
Links
- MHHOMHMNIRXARC-UHFFFAOYSA-N 1h-pyrido[2,3-d]pyrimidin-2-one Chemical class C1=CN=C2NC(=O)N=CC2=C1 MHHOMHMNIRXARC-UHFFFAOYSA-N 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims 23
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 16
- 125000003342 alkenyl group Chemical group 0.000 claims 13
- -1 amino, carbonyl Chemical group 0.000 claims 12
- 125000000304 alkynyl group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 5
- XDLYKKIQACFMJG-UHFFFAOYSA-N 2-amino-8-[4-(2-hydroxyethoxy)cyclohexyl]-6-(6-methoxypyridin-3-yl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1C1CCC(OCCO)CC1 XDLYKKIQACFMJG-UHFFFAOYSA-N 0.000 claims 3
- LPJUKWATMDFWDN-UHFFFAOYSA-N 2-amino-6-bromo-8-[4-(2-hydroxyethoxy)cyclohexyl]-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C(Br)=CC=2C(C)=NC(N)=NC=2N1C1CCC(OCCO)CC1 LPJUKWATMDFWDN-UHFFFAOYSA-N 0.000 claims 2
- WOMVHFKOGGCXMG-SHTZXODSSA-N C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 Chemical compound C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 WOMVHFKOGGCXMG-SHTZXODSSA-N 0.000 claims 2
- PDCGXSKEKLYDRP-SHTZXODSSA-N C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 PDCGXSKEKLYDRP-SHTZXODSSA-N 0.000 claims 2
- LOYNAYXFINASCA-HDJSIYSDSA-N chembl2375954 Chemical compound O=C1C(C2=CN(C)N=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCC(N)=O)CC1 LOYNAYXFINASCA-HDJSIYSDSA-N 0.000 claims 2
- NNXNZTDFLLHLOS-JOCQHMNTSA-N chembl2375955 Chemical compound O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCC(N)=O)CC1 NNXNZTDFLLHLOS-JOCQHMNTSA-N 0.000 claims 2
- VNSCNWLXUYATCI-HDJSIYSDSA-N chembl2375956 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCC(N)=O)CC1 VNSCNWLXUYATCI-HDJSIYSDSA-N 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- FWILAFBSYLISCN-UHFFFAOYSA-N 2-amino-4-methyl-7-oxo-8-propan-2-yl-n-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1N(C(C)C)C2=NC(N)=NC(C)=C2C=C1C(=O)NC1=CC=NN1 FWILAFBSYLISCN-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- IWYRRPAYAHUCKP-UHFFFAOYSA-N 8-cyclopentyl-4-methyl-2-(methylamino)-7-oxo-n-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1N(C2CCCC2)C2=NC(NC)=NC(C)=C2C=C1C(=O)NC=1C=CNN=1 IWYRRPAYAHUCKP-UHFFFAOYSA-N 0.000 claims 1
- SPZLNUYSXWJTDI-UHFFFAOYSA-N 8-cyclopentyl-4-methyl-2-(methylamino)-7-oxo-n-pyridin-2-ylpyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1N(C2CCCC2)C2=NC(NC)=NC(C)=C2C=C1C(=O)NC1=CC=CC=N1 SPZLNUYSXWJTDI-UHFFFAOYSA-N 0.000 claims 1
- MOWFUTLFKBZDFZ-UHFFFAOYSA-N 8-cyclopentyl-4-methyl-2-(methylamino)-n-(1,2-oxazol-3-yl)-7-oxopyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1N(C2CCCC2)C2=NC(NC)=NC(C)=C2C=C1C(=O)NC=1C=CON=1 MOWFUTLFKBZDFZ-UHFFFAOYSA-N 0.000 claims 1
- HKEYODYWKVJZML-UHFFFAOYSA-N 8-cyclopentyl-n-[(1-ethylpyrazol-4-yl)methyl]-4-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound C1=NN(CC)C=C1CNC(=O)C(C1=O)=CC2=C(C)N=C(NC)N=C2N1C1CCCC1 HKEYODYWKVJZML-UHFFFAOYSA-N 0.000 claims 1
- JVQZXWSJZFSIQS-HAQNSBGRSA-N C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 Chemical compound C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 JVQZXWSJZFSIQS-HAQNSBGRSA-N 0.000 claims 1
- MQYKSHFHKJXVCJ-JOCQHMNTSA-N C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 Chemical compound C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 MQYKSHFHKJXVCJ-JOCQHMNTSA-N 0.000 claims 1
- PCOJUVWPYNNKBZ-ULQDDVLXSA-N C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OC[C@@H](O)CO)CC1 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OC[C@@H](O)CO)CC1 PCOJUVWPYNNKBZ-ULQDDVLXSA-N 0.000 claims 1
- UTGVSQLUEPNLMK-JOCQHMNTSA-N C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 UTGVSQLUEPNLMK-JOCQHMNTSA-N 0.000 claims 1
- KEANLVNTCDMYDG-HDJSIYSDSA-N C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 KEANLVNTCDMYDG-HDJSIYSDSA-N 0.000 claims 1
- IIFFBBBKGQXRDI-HAQNSBGRSA-N C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCC(N)=O)C1 IIFFBBBKGQXRDI-HAQNSBGRSA-N 0.000 claims 1
- ISROHHNFTMLKES-JOCQHMNTSA-N C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 ISROHHNFTMLKES-JOCQHMNTSA-N 0.000 claims 1
- PDCGXSKEKLYDRP-GASCZTMLSA-N C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCCO)CC1 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCCO)CC1 PDCGXSKEKLYDRP-GASCZTMLSA-N 0.000 claims 1
- FMHCGDSGNZNXMH-SHTZXODSSA-N C1C[C@@H](OCC(=O)OC)CC[C@@H]1N1C(=O)C(C=2C=C(F)C(OC)=NC=2)=CC2=C(C)N=C(N)N=C21 Chemical compound C1C[C@@H](OCC(=O)OC)CC[C@@H]1N1C(=O)C(C=2C=C(F)C(OC)=NC=2)=CC2=C(C)N=C(N)N=C21 FMHCGDSGNZNXMH-SHTZXODSSA-N 0.000 claims 1
- YNZNTPOICGBWLG-JOCQHMNTSA-N CCN1N=CC=C1NC(=O)C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](O)CC1 Chemical compound CCN1N=CC=C1NC(=O)C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](O)CC1 YNZNTPOICGBWLG-JOCQHMNTSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- RYSSGCRLQZGFKU-XYPYZODXSA-N O=C1C(C(=O)NC=2NN=CC=2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](O)CC1 Chemical compound O=C1C(C(=O)NC=2NN=CC=2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](O)CC1 RYSSGCRLQZGFKU-XYPYZODXSA-N 0.000 claims 1
- BPRLASJBTWVPSB-SHTZXODSSA-N O=C1C(C2=CN(C)N=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C2=CN(C)N=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 BPRLASJBTWVPSB-SHTZXODSSA-N 0.000 claims 1
- UAADDCZXGPRVQO-OKILXGFUSA-N O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCCO)CC1 UAADDCZXGPRVQO-OKILXGFUSA-N 0.000 claims 1
- UAADDCZXGPRVQO-HDJSIYSDSA-N O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 UAADDCZXGPRVQO-HDJSIYSDSA-N 0.000 claims 1
- GPUZESZBHMOJPX-JOCQHMNTSA-N O=C1C(C2=NNC=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C2=NNC=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 GPUZESZBHMOJPX-JOCQHMNTSA-N 0.000 claims 1
- OHDMKRUUAMWKJE-KDURUIRLSA-N O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCCO)CC1 OHDMKRUUAMWKJE-KDURUIRLSA-N 0.000 claims 1
- OHDMKRUUAMWKJE-WGSAOQKQSA-N O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 OHDMKRUUAMWKJE-WGSAOQKQSA-N 0.000 claims 1
- 125000005631 S-sulfonamido group Chemical group 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000010261 cell growth Effects 0.000 claims 1
- GRHRLQVZBUMCGW-IYARVYRRSA-N chembl2375953 Chemical compound O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCC(N)=O)CC1 GRHRLQVZBUMCGW-IYARVYRRSA-N 0.000 claims 1
- AICMEPHIKCWYDQ-SHTZXODSSA-N chembl2375958 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCC(N)=O)CC1 AICMEPHIKCWYDQ-SHTZXODSSA-N 0.000 claims 1
- GRHRLQVZBUMCGW-HDICACEKSA-N chembl2375959 Chemical compound O=C1C(C=2C=C3C=CC=CC3=NC=2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCC(N)=O)CC1 GRHRLQVZBUMCGW-HDICACEKSA-N 0.000 claims 1
- NNXNZTDFLLHLOS-BETUJISGSA-N chembl2375962 Chemical compound O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@@H]1CC[C@H](OCC(N)=O)CC1 NNXNZTDFLLHLOS-BETUJISGSA-N 0.000 claims 1
- OKZQPXUPXMKTBL-OKILXGFUSA-N chembl2375963 Chemical compound C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCC(N)=O)CC1 OKZQPXUPXMKTBL-OKILXGFUSA-N 0.000 claims 1
- AICMEPHIKCWYDQ-GASCZTMLSA-N chembl2375964 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCC(N)=O)CC1 AICMEPHIKCWYDQ-GASCZTMLSA-N 0.000 claims 1
- 125000004803 chlorobenzyl group 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
Claims (16)
1. Spoj Formule (I)
[image]
ili njegova sol,
naznačen time što:
R1 je H ili (C1 do C6) alkil, izborno supstituiran s najmanje jednom skupinom R5;
A je 3- do 10-eročlana cikloalkilna skupina;
R2 je (C1 do C6) alkil, supstituiran s najmanje jednom skupinom R6, (C3 do C10) cikloalkil, (C2 do C6) cikloheteroalkil, (C6 do C14) aril, (C2 do C9) heteroaril, -NR7aR7b ili -N=CR8aR8b, gdje je svaki od navedenih (C3 do C10) cikloalkila, (C2 do C9) cikloheteroalkila, (C6 do C14) arila, te (C2 do C9) heteroarila izborno supstituiran s najmanje jednom skupinom R9;
R3 je (C1 do C6) alkil, (C3 do C10) cikloalkil, (C2 do C9) cikloheteroalkil, (C2 do C8) alkenil, (C2 do C8) alkinil, halogen, cijano, -(CH2)nC(O)OR10, -(CH2)nC(O)N(R11aR11b), COR12, (C6 do C14) aril ili (C2 do C9) heteroaril, gdje su navedeni (C1 do C6) alkil, (C3 do C10) cikloalkil, (C2 do C9) cikloheteroalkil, (C2 do C8) alkenil, (C2 do C8) alkinil, (C6 do C14) aril i (C2 do C9) heteroaril izborno supstituirani s najmanje jednom skupinom R9;
svaki R4 je neovisno -OH, halogen, CF3, -NR11aR11b, (C1 do C6) alkil, (C1 do C6) alkenil, (C1 do C6) alkinil, (C1 do C6) alkoksi, cijano, (C3 do C10) cikloalkil, (C2 do C9) cikloheteroalkil, (C6 do C14) aril, (C2 do C9) heteroaril, -C(O)R12-C(O)NR11aR11b, -S(O)mR12, -S(O)mNR11aR11b, -NR11aS(O)mR12-(CH2)nC(O)OR10, -(CH2)nC(O)N(R11aR11b), -OC(O)R12, -NR11aC(O)R12 ili -NR11aC(O)N(R11aR11b), gdje je svaki od navedenih (C1 do C6) alkila, (C1 do C6) alkenila, (C1 do C6) alkinila, (C1 do C6) alkoksi, (C3 do C10) cikloalkila, (C2 do C9) cikloheteroalkila, (C6 do C12) arila, te (C2 do C9) heteroarila izborno supstituiran s najmanje jednom skupinom R13;
svaki R5 je neovisno -OH, halogen, CF3, -NR11aR11b, (C1 do C6) alkil, (C1 do C6) alkoksi, cijano, (C3 do C10) cikloalkil, (C2 do C9) cikloheteroalkil, (C6 do C14) aril, (C2 do C9) heteroaril, -S(O)mR12, -S(O)mNR11aR11b, -C(O)R12 ili -C(O)NR11aR11b, gdje je svaki od navedenih (C1 do C6) alkila, (C1 do C6) alkoksi, (C3 do C10) cikloalkila, (C2 do C9) cikloheteroalkila, (C6 do C14) arila, te (C2 do C9) heteroarila izborno supstituiran s najmanje jednom skupinom R9;
svaki R6 je neovisno -OH, (C1 do C6) alkinil, cijano, (C3 do C10) cikloalkil, (C2 do C9) cikloheteroalkil, (C6 do C14) aril, (C2 do C6) heteroaril, -C(O)R12 -C(O)NR11aR11b, -S(O)mR12, -S(O)mNR11aR11b, -NR11aS(O)mR12-(CH2)nC(O)OR10, -(CH2)nC(O)N(R11aR11b), -OC(O)R12, -NR11aC(O)R12 ili -NR11aC(O)N(R11aR11b), gdje je svaki od navedenih (C1 do C6) alkinila, (C3 do C10) cikloalkila, (C2 do C9) cikloheteroalkila, (C6 do C12) arila, te (C2 do C9) heteroarila izborno supstituiran s najmanje jednom skupinom R13;
svaki od R7a i R7b je neovisno H, (C1 do C6) alkil, (C2 do C6)alkenil, (C2 do C6)alkinil, (C3 do C10) cikloalkil ili (C6 do C10)aril, gdje je svaki od navedenih (C1 do C6) alkila, (C2 do C6)alkenila, (C2 do C6)alkinila, (C3 do C10) cikloalkila, te (C6 do C10)arila izborno supstituiran s najmanje jednom skupinom R9; ili se R7a i R7b može uzeti zajedno s atomom dušika kako bi tvorili 5- do 8-eročlani heterociklilni prsten, gdje navedeni heterociklilni prsten ima 1 do 3 heteroatoma u prstenu, koje se bira iz skupine koju čine N, O i S, te gdje je navedeni 5- do 8-eročlani cikloheteroalkilni prsten izborno supstituiran s najmanje jednom skupinom R9;
svaki od R8a i R8b je neovisno H, (C1 do C6) alkil ili (C3 do C10) cikloalkil, gdje je svaki od navedenih (C1 do C6) alkila i (C3 do C10) cikloalkila izborno supstituiran s najmanje jednom skupinom R9;
svaki R9 je neovisno -OH, halogen, CF3, -NR11aR11b, (C1 do C6) alkil, (C1 do C6) alkenil, (C1 do C6) alkinil, (C1 do C6) alkoksi, cijano, (C3 do C10) cikloalkil, (C2 do C9) cikloheteroalkil, (C6 do C14) aril, (C2 do C9) heteroaril, -C(O)R12 -C(O)NR11aR11b, -S(O)mR12, -S(O)mNR11aR11b, -NR11aS(O)mR12 -(CH2)nC(O)OR10, -(CH2)nC(O)N(R11aR11b), -OC(O)R12, -NR11aC(O)R12 ili -NR11aC(O)N(R11aR11b), gdje je svaki od navedenih (C1 do C6) alkila, (C1 do C6) alkenila, (C1 do C6) alkinila, (C1 do C6) alkoksi, (C3 do C10) cikloalkila, (C2 do C9) cikloheteroalkila, (C6 do C12) arila, te (C2 do C9) heteroarila izborno supstituiran s najmanje jednom skupinom R13;
svaki R10 je neovisno H, ili (C1 do C6) alkil;
R11a i R11b svaki od je neovisno H, (C1 do C6) alkil, (C2 do C9) cikloheteroalkil, (C2 do C9) heteroaril ili (C6 do C12) aril, gdje je svaki od navedenih (C1 do C6) alkila, (C2 do C9) cikloheteroalkila, (C2 do C9) heteroarila, te (C6 do C12) arila izborno supstituiran s najmanje jednom skupinom R13;
svaki od R12 je neovisno (C1 do C6) alkil, (C3 do C10) cikloalkil, (C2 do C9) cikloheteroalkil, (C2 do C9) heteroaril ili (C6 do C14) aril, gdje je svaki od navedenih (C1 do C6) alkila, (C3 do C10) cikloalkila, (C2 do C9) cikloheteroalkila, (C2 do C9) heteroarila, te (C6 do C14) arila izborno supstituiran s najmanje jednom skupinom R13;
svaki od R13 je neovisno -OH, halogen, CF3, (C1 do C6) alkil, (C1 do C6) alkenil, (C1 do C6) alkinil, (C1 do C6) alkoksi, cijano, (C3 do C10) cikloalkil, (C2 do C9) cikloheteroalkil, (C6 do C14) aril, (C2 do C9) heteroaril, amino, karbonil, C-amido, sulfinil, S-sulfonamido, C-karboksil, N-amido ili N-karbamil;
svaki m je neovisno 1 ili 2;
svaki n je neovisno 0, 1, 2, 3 ili 4; i
svaki z je cijeli broj, kojeg se neovisno bira između 0, 1, 2, 3, 4, 5, 6, 7 ili 8.
2. Spoj ili sol u skladu s patentnim zahtjevom 1, naznačen time što A je cikloheksil.
3. Spoj ili sol u skladu s patentnim zahtjevom 1 ili 2, naznačen time što R3 je (C6 do C14) aril ili (C2 do C9) heteroaril, gdje su navedeni (C6 do C14) aril ili (C2 do C9) heteroaril izborno supstituirani s najmanje jednom skupinom R9.
4. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira iz skupine koju čine: 2-amino-6-(5-fluor-6-metoksipiridin-3-il)-8-[trans-4-(2-hidroksietoksi)cikloheksil]-4-metilpirido[2,3-d]pirimidin-7(8H)-on; 2-amino-8-[trans-4-(2-hidroksietoksi)cikloheksil]-6-(6-metoksipiridin-3-il)-4-metilpirido[2,3-d]pirimidin-7(8H)-on; 2-amino-8-[trans-4-(2-hidroksietoksi)cikloheksil]-4-metil-6-kinolin-3-ilpirido[2,3-d]pirimidin-7(8H)-on; 2-amino-8-[trans-4-(2-hidroksietoksi)cikloheksil]-6-(2-metoksipirimidin-5-il)-4-metilpirido[2,3-d]pirimidin-7(8H)-on; 2-amino-8-[trans-4-(2-hidroksietoksi)cikloheksil]-4-metil-6-(1H-pirazol-4-il)pirido[2,3-d]pirimidin-7(8H)-on; 2-amino-6-brom-8-[trans-4-(2-hidroksietoksi)cikloheksil]-4-metilpirido[2,3-d]pirimidin-7(8H)-on; 2-amino-8-[cis-4-(2-hidroksietoksi)cikloheksil]-4-metil-6(1H-pirazol-4-il)pirido[2,3-d]pirimidin-7(8H)-on; 2-amino-8-(trans-4-{[(2S)-2,3-dihidroksipropil]oksi}cikloheksil)-6-(6-metoksipiridin-3-il)-4-metilpirido[2,3-d]pirimidin-7(8H)-on; 2-amino-8-[cis-4-(2-hidroksietoksi)cikloheksil]-4-metil-6-kinolin-3-ilpirido[2,3-d]pirimidin-7(8H)-on; 2-amino-6-(5-fluor-6-metoksipiridin-3-il)-8-[cis-4-(2-hidroksietoksi)cikloheksil]-4-metilpirido[2,3-d]pirimidin-7(8H)-on; 2-amino-8-[cis-4-(2-hidroksietoksi)cikloheksil]-6-(2-metoksipirimidin-5-il)-4-metilpirido[2,3-d]pirimidin-7(8H)-on; 2-amino-8-[cis-4-(2-hidroksietoksi)cikloheksil]-6-(6-metoksipiridin-3-il)-4-metilpirido[2,3-d]pirimidin-7(8H)-on; 2-amino-6-brom-8-[cis-4-(2-hidroksietoksi)cikloheksil]-4-metilpirido[2,3-d]pirimidin-7(8H)-on; 2-amino-6-[6-(dimetilamino)piridin-3-il]-8-[trans-4-(2-hidroksietoksi)cikloheksil]-4-metilpirido[2,3-d]pirimidin-7(8H)-on; 2({trans-4-[2-amino-6-(5-fluor-6-metoksipiridin-3-il)-4-metil-7-oksopirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid; metil-({trans-4-[2-amino-6-(5-fluor-6-metoksipiridin-3-il)-4-metil-7-oksopirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetat; 2-amino-8-[trans-4-(2-hidroksietoksi)cikloheksil]-4-metil-6-(1H-pirazol-3-il)pirido[2,3-d]pirimidin-7(8H)-on, 2-amino-8-[trans-4-(2-hidroksietoksi)cikloheksil]-4-metil-6-(1-metil-1H-pirazol-4-il)pirido[2,3-d]pirimidin-7(8H)-on, 2-({cis-4-[2-amino-6-(6-metoksipiridin-3-il)-4-metil-7-oksopirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, 2-({cis-4-[2-amino-6-(5-fluor-6-metoksipiridin-3-il)-4-metil-7-oksopirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, 2-({cis-4-[2-amino-4-metil-7-okso-6-(1H-pirazol-4-il)pirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, 2-({cis-4-[2-amino-4-metil-6-(1-metil-1H-pirazol-4-il)-7-oksopirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, 2-({cis-4-[2-amino-6-(2-metoksipirimidin-5-il)-4-metil-7-oksopirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, 2-{[cis-4-(2-amino-4-metil-7-okso-6-kinolin-3-ilpirido[2,3-d]pirimidin-8(7H)-il)cikloheksil]oksi}acetamid, 2-({trans-4-[2-amino-6-(6-metoksipiridin-3-il)-4-metil-7-oksopirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, 2-{[trans-4-(2-amino-4-metil-7-okso-6-kinolin-3-ilpirido[2,3-d]pirimidin-8(7H)-il)cikloheksil]oksi}acetamid, 2-({trans-4-[2-amino-6-(2-metoksipirimidin-5-il)-4-metil-7-oksopirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, 2-({trans-4-[2-amino-4-metil-7-okso-6-(1H-pirazol-4-il)pirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, 2-({trans-4-[2-amino-4-metil-6-(1-metil-1H-pirazol-4-il)-7-oksopirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, 2-amino-8-[trans-3-(2-hidroksietoksi)ciklobutil]-6-(6-metoksipiridin-3-il)-4-metilpirido[2,3-d]pirimidin-7(8H)-on, 2-amino-6-(5-fluor-6-metoksipiridin-3-il)-8-[trans-3-(2-hidroksietoksi)ciklobutil]-4-metilpirido[2,3-d]pirimidin-7(8H)-on, 2-amino-8-[trans-3-(2-hidroksietoksi)ciklobutil]-6-(2-metoksipirimidin-5-il)-4-metilpirido[2,3-d]pirimidin-7(8H)-on, 2-({trans-3-[2-amino-6-(6-metoksipiridin-3-il)-4-metil-7-oksopirido[2,3-d]pirimidin-8(7H)-il]ciklobutil}oksi)acetamid, 2-({trans-3-[2-amino-6-(5-fluor-6-metoksipiridin-3-il)-4-metil-7-oksopirido[2,3-d]pirimidin-8(7H)-il]ciklobutil}oksi)acetamid, 2-({trans-3-[2-amino-6-(2-metoksipirimidin-5-il)-4-metil-7-oksopirido[2,3-d]pirimidin-8(7H)-il]ciklobutil}oksi)acetamid, ili njihove soli.
5. Spoj Formule (II)
[image]
ili njegova sol,
naznačen time što:
R1 je H ili (C1 do C6) alkil, izborno supstituiran s najmanje jednom skupinom R4;
R2 je (C1 do C6) alkil, (C2 do C8) alkenil, (C3 do C10) cikloalkil, (C5 do C8) cikloalkenil, (C2 do C9) cikloheteroalkil ili -(CH2)n(C6 do C14) aril, gdje su navedeni (C1 do C6) alkil, (C2 do C8) alkenil, (C3 do C10) cikloalkil, (C5 do C8) cikloalkenil, (C2 do C9) cikloheteroalkil, te -(CH2)n(C8 do C14) aril izborno supstituirani s najmanje jednom skupinom R4;
R3 je (C1 do C6) alkil, (C2 do C8) alkenil, cijano, -(CH2)nC(O)OR5a ili -(CH2)nC(O)N(R5aR5b), gdje su navedeni (C1 do C6) alkil ili (C2 do C8) alkenil izborno supstituirani s najmanje jednom skupinom R4;
svaki R4 je neovisno -OH, halogen, CF3, -NR5aR5b, (C1 do C6) alkil, (C1 do C6) alkoksi, cijano, (C3 do C10) cikloalkil, -S(O)mR5a, -S(O)mNR5aR5b, -C(O)R5a ili -C(O)NR5aR5b;
svaki od R5a i R5b je neovisno H, (C1 do C6) alkil, (C2 do C9) cikloheteroalkil, (C2 do C9) heteroaril ili (C6 do C14) aril;
svaki m je neovisno 1 ili 2; i
svaki n je neovisno 0, 1, 2, 3 ili 4.
6. Spoj ili sol u skladu s patentnim zahtjevom 5, naznačen time što R3 je -(CH2)nC(O)N(R5aR5b).
7. Spoj ili sol u skladu s patentnim zahtjevom 5 ili 6, naznačen time što R2 se bira iz skupine koju čine izopropil, alil, ciklopentil, ciklobutil, hidroksicikloheksil, hidroksiciklopentil, hidroksiciklobutil, hidroksicikloheptil, metoksietil, metoksipropil, etil, metil, ciklopropil, ciklopropilmetil, ciklopropiletil, 2-metil-2-hidroksipropil, 3-metil-3-hidroksilbutil, metoksibenzil, te klorbenzil.
8. Spoj u skladu s patentnim zahtjevom 5, naznačen time što ga se bira iz skupine koju čine: 2-amino-8-(trans-4-hidroksicikloheksil)-4-metil-7-okso-N-1H-pirazol-5-il-7,8-dihidropirido[2,3-d]pirimidin-6-karboksamid; 2-amino-N-(1-etil-1H-pirazol-5-il)-8-(trans-4-hidroksicikloheksil)-4-metil-7-okso-7,8-dihidropirido[2,3-d]pirimidin-6-karboksamid; (1H-pirazol-3-il)amid 8-ciklopentil-4-metil-2-metilamino-7-okso-7,8-dihidropirido[2,3-d]pirimidin-6-karboksilne kiseline; 2-amino-8-izopropil-4-metil-7-okso-N-1H-pirazol-5-il-7,8-dihidropirido[2,3-d]pirimidin-6-karboksamid; 2-amino-N-(1-etil-1H-pirazol-6-il)-8-izopropil-4-metil-7-okso-7,8-dihidropirido[2,3-d]pirimidin-6-karboksamid; 8-ciklopentil-N-[(1-etil-1H-pirazol-4-il)metil]-4-metil-2-(metilamino)-7-okso-7,8-dihidropirido[2,3-d]pirimidin-6-karboksamid; 8-ciklopentil-4-metil-2-(metilamino)-7-okso-N-piridin-2-il-7,8-dihidropirido[2,3-d]pirimidin-6-karboksamid; te 8-ciklopentil-N-izoksazol-3-il-4-metil-2-(metilamino)-7-okso-7,8-dihidropirido[2,3-d]pirimidin-6-karboksamid, ili njihove soli.
9. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 2-amino-6-(5-fluor-6-metoksipiridin-3-il)-8-[trans-4-(2-hidroksietoksi)cikloheksil]-4-metilpirido[2,3-d]pirimidin-7(8H)-on, ili njegova sol.
10. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 2-amino-8-[trans-4-(2-hidroksietoksi)cikloheksil]-6-(6-metoksipiridin-3-il)-4-metilpirido[2,3-d]pirimidin-7(8H)-on, ili njegova sol.
11. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 2-amino-8-[trans-4-(2-hidroksietoksi)cikloheksil]-6-(2-metoksipirimidin-5-il)-4-metilpirido[2,3-d]pirimidin-7(8H)-on, ili njegova sol.
12. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 2-({trans-4-[2-amino-6-(2-metoksipirimidin-5-il)-4-metil-7-oksopirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, ili njegova sol.
13. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 2-({trans-4-[2-amino-4-metil-7-okso-6-(1H-pirazol-4-il)pirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, ili njegova sol.
14. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 2-({trans-4-[2-amino-4-metil-6-(1-metil-1H-pirazol-4-il)-7-oksopirido[2,3-d]pirimidin-8(7H)-il]cikloheksil}oksi)acetamid, ili njegova sol.
15. Upotreba spoja, ili soli, u skladu s bilo kojim od patentnih zahtjeva 1 do 10, naznačena time što je navedeni spoj namijenjen proizvodnji medikamenta za liječenje abnormalnog staničnog rasta kod sisavca.
16. Farmaceutski pripravak, naznačen time što sadrži najmanje jedan spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 14, ili njegovu sol, i farmaceutski prihvatljivu podlogu ili razrjeđivač.
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| PCT/IB2007/002578 WO2008032162A1 (en) | 2006-09-15 | 2007-09-03 | Pyrido (2, 3-d) pyrimidin0ne compounds and their use as pi3 inhibitors |
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| SI2139484T1 (sl) * | 2007-04-10 | 2013-10-30 | Exelixis, Inc. | Postopki za zdravljenje raka s pirido pirimidin PI3K alfa inhibitorji |
| CA2683820A1 (en) * | 2007-04-11 | 2008-10-23 | Exelixis, Inc. | Pyrido [2, 3-d] pyrimidin-7-one compounds as inhibitors of p13k-alpha for the treatment of cancer |
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