HRP20140437T1 - Bicikliäśki spojevi i njihove uporabe kao dualnih c-src/jak inhibitora - Google Patents
Bicikliäśki spojevi i njihove uporabe kao dualnih c-src/jak inhibitora Download PDFInfo
- Publication number
- HRP20140437T1 HRP20140437T1 HRP20140437AT HRP20140437T HRP20140437T1 HR P20140437 T1 HRP20140437 T1 HR P20140437T1 HR P20140437A T HRP20140437A T HR P20140437AT HR P20140437 T HRP20140437 T HR P20140437T HR P20140437 T1 HRP20140437 T1 HR P20140437T1
- Authority
- HR
- Croatia
- Prior art keywords
- substituted
- phenyl
- methyl
- unsubstituted
- pyrimidin
- Prior art date
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- 229940122245 Janus kinase inhibitor Drugs 0.000 title 1
- 102000001332 SRC Human genes 0.000 title 1
- 108060006706 SRC Proteins 0.000 title 1
- 125000002619 bicyclic group Chemical group 0.000 title 1
- 230000009977 dual effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- MUDHLBBYVLVLQA-UHFFFAOYSA-N C1=CC(C(=O)NC)=CC=C1NC1=NC=C(CN(CC2)C=3C(=CC=C(N)C=3)Cl)C2=N1 Chemical compound C1=CC(C(=O)NC)=CC=C1NC1=NC=C(CN(CC2)C=3C(=CC=C(N)C=3)Cl)C2=N1 MUDHLBBYVLVLQA-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- LCIAAEMZZHAWAG-UHFFFAOYSA-N n-[4-chloro-3-[2-[3-methyl-4-(4-methylpiperazin-1-yl)anilino]-5-oxo-7,8-dihydropyrido[4,3-d]pyrimidin-6-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C(C(=C1)C)=CC=C1NC1=NC=C(C(=O)N(CC2)C=3C(=CC=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=3)Cl)C2=N1 LCIAAEMZZHAWAG-UHFFFAOYSA-N 0.000 claims 2
- VNNKWGYOOWZBFH-UHFFFAOYSA-N n-[4-chloro-3-[2-[4-[2-(cyclopropylamino)-2-oxoethoxy]anilino]-5-oxo-7,8-dihydropyrido[4,3-d]pyrimidin-6-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C(Cl)=CC=2)N2C(C3=CN=C(NC=4C=CC(OCC(=O)NC5CC5)=CC=4)N=C3CC2)=O)=C1 VNNKWGYOOWZBFH-UHFFFAOYSA-N 0.000 claims 2
- WVGSOXRZIVSEQO-UHFFFAOYSA-N n-[4-methyl-3-[2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxo-7,8-dihydropyrido[4,3-d]pyrimidin-6-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(=O)N(CC2)C=3C(=CC=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=3)C)C2=N1 WVGSOXRZIVSEQO-UHFFFAOYSA-N 0.000 claims 2
- 150000003222 pyridines Chemical class 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- XLJBSQRVAHEFDW-UHFFFAOYSA-N 1-cyclopentyl-3-[4-methyl-3-[2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=C(N2CC3=CN=C(NC=4C=CC(OCCN5CCCC5)=CC=4)N=C3CC2)C(C)=CC=C1NC(=O)NC1CCCC1 XLJBSQRVAHEFDW-UHFFFAOYSA-N 0.000 claims 1
- SIWSWPNFRJLOFG-UHFFFAOYSA-N 3-bromo-n-[4-methyl-3-[2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxo-7,8-dihydropyrido[4,3-d]pyrimidin-6-yl]phenyl]benzamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(=O)N(CC2)C=3C(=CC=C(NC(=O)C=4C=C(Br)C=CC=4)C=3)C)C2=N1 SIWSWPNFRJLOFG-UHFFFAOYSA-N 0.000 claims 1
- UZICUOYVCKOCLZ-UHFFFAOYSA-N 4,4,4-trifluoro-3-methyl-n-[4-methyl-3-[2-[4-[2-(4-methylpiperazin-1-yl)ethoxy]anilino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]phenyl]butanamide Chemical compound FC(F)(F)C(C)CC(=O)NC1=CC=C(C)C(N2CC3=CN=C(NC=4C=CC(OCCN5CCN(C)CC5)=CC=4)N=C3CC2)=C1 UZICUOYVCKOCLZ-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- GNZYCJHLEZPHRI-UHFFFAOYSA-N FC(C1=CC(=NC=C1)C(=O)O)(F)F.C1(CC1)NC(=O)C1=NC=C(C=C1)NC=1N=CC2=C(N1)CCN(C2)C2=C(C=CC(=C2)NC(C2=CC(=CC=C2)C(F)(F)F)=O)C Chemical compound FC(C1=CC(=NC=C1)C(=O)O)(F)F.C1(CC1)NC(=O)C1=NC=C(C=C1)NC=1N=CC2=C(N1)CCN(C2)C2=C(C=CC(=C2)NC(C2=CC(=CC=C2)C(F)(F)F)=O)C GNZYCJHLEZPHRI-UHFFFAOYSA-N 0.000 claims 1
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 1
- PBGFGGSCPMAILX-UHFFFAOYSA-N N-[4-chloro-3-[2-[4-(4-methylpiperazin-1-yl)anilino]-5-oxo-7,8-dihydropyrido[4,3-d]pyrimidin-6-yl]phenyl]-3-(trifluoromethyl)benzamide 4-(trifluoromethyl)pyridine-2-carboxylic acid Chemical compound FC(C1=CC(=NC=C1)C(=O)O)(F)F.ClC1=C(C=C(C=C1)NC(C1=CC(=CC=C1)C(F)(F)F)=O)N1C(C2=C(N=C(N=C2)NC2=CC=C(C=C2)N2CCN(CC2)C)CC1)=O PBGFGGSCPMAILX-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 102000004495 STAT3 Transcription Factor Human genes 0.000 claims 1
- 108010017324 STAT3 Transcription Factor Proteins 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 150000002357 guanidines Chemical class 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 208000014951 hematologic disease Diseases 0.000 claims 1
- 208000018706 hematopoietic system disease Diseases 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- SCDTVQOOFJOJPO-UHFFFAOYSA-N n-[3-[2-[4-(cyclopropylsulfamoyl)anilino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(N2CC3=CN=C(NC=4C=CC(=CC=4)S(=O)(=O)NC4CC4)N=C3CC2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 SCDTVQOOFJOJPO-UHFFFAOYSA-N 0.000 claims 1
- FZAJJLSXVPASPF-UHFFFAOYSA-N n-[4-chloro-3-[2-[4-[(4-methylpiperazin-1-yl)methyl]anilino]-5-oxo-7,8-dihydropyrido[4,3-d]pyrimidin-6-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C(=O)N(CC2)C=3C(=CC=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=3)Cl)C2=N1 FZAJJLSXVPASPF-UHFFFAOYSA-N 0.000 claims 1
- CZZVNONIDUMKCY-UHFFFAOYSA-N n-[4-methyl-3-[2-[4-(4-methylpiperazine-1-carbonyl)anilino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(CN(CC2)C=3C(=CC=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=3)C)C2=N1 CZZVNONIDUMKCY-UHFFFAOYSA-N 0.000 claims 1
- JJHRHADNFSGPGT-UHFFFAOYSA-N n-[4-methyl-3-[5-oxo-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-7,8-dihydropyrido[4,3-d]pyrimidin-6-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(N2C(C3=CN=C(NC=4C=CC(OCCN5CCCC5)=CC=4)N=C3CC2)=O)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 JJHRHADNFSGPGT-UHFFFAOYSA-N 0.000 claims 1
- AXVSSJPRDFYPMF-UHFFFAOYSA-N n-cyclopropyl-5-[[6-[2-methyl-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]amino]pyridine-2-carboxamide Chemical compound C1=C(N2CC3=CN=C(NC=4C=NC(=CC=4)C(=O)NC4CC4)N=C3CC2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 AXVSSJPRDFYPMF-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 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
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Claims (14)
1. Spoj formule (I) koji ima strukturu
[image]
gdje
R1 je H, aril, supstituirani aril, alkil, supstituirani alkil, heteroaril, supstituirani heteroaril, heterociklil, supstituirani heterociklil, heterociklilalkil ili supstituirani heterociklilalkil,
X je CH2 ili C=O
R2 je H, (C1-C6)alkil, halogen, CF3, ili -O-(C1-C6)alkil
Y je -NHCO-, -CONH-, -NHSO2-, -NH-, -NCH3-CO-, -NHCH2-, O, -NHCONH- ili -NHCOCH2-
R3 je alkil, supstituirani alkil, aril, ili supstituirani aril, heteroaril, supstituirani heteroaril, cikloalkil, supstituirani cikloalkil ili heterocikloalkil;
gdje
pojam "alkil" odnosi se na zasićene alifatske skupine, uključujući ravno-lančane alkilne skupine, alkilne skupine razgranatog lanca, cikloalkilne (alicikličke) skupine, alkil supstituirane cikloalkilne skupine, i cikloalkil supstituirane alkilne skupine;
pojam "cikloalkil" odnosi se na zasićene ili djelomično zasićene, monocikličke ili fuzionirane ili spiro policikličke karbocikle;
pojam "heterocikloalkil" ili "heterociklil" odnosi se na ne-aromatski djelomično nezasićeni ili potpuno zasićeni 3 do 10-eročlani prstenasti sustav, koji obuhvaća jedan prsten s 3 do 8 atoma u svojoj veličini i bi- ili tri-cikličke sustave prstena koji mogu obuhvaćati aromatske šesteročlane arilne ili heteroarilne prstenove fuzionirane za ne-aromatski prsten;
pojam "supstituirani" odnosi se na supstituciju s bilo kojim jednim ili više ili bilo kojom kombinacijom sljedećih supstituenata: hidroksi, halogen, karboksil, cijano, nitro, okso (=O), tio (=S), supstituirani ili nesupstituirani alkil, supstituirani ili nesupstituirani haloalkil, supstituirani ili nesupstituirani alkoksi, supstituirani ili nesupstituirani haloalkoksi, supstituirani ili nesupstituirani alkenil, supstituirani ili nesupstituirani alkinil, supstituirani ili nesupstituirani aril, supstituirani ili nesupstituirani arilalkil, supstituirani ili nesupstituirani cikloalkil, supstituirani ili nesupstituirani cikloalkenilalkil, supstituirani ili nesupstituirani cikloalkenil, supstituirani ili nesupstituirani amino, supstituirani ili nesupstituirani aril, supstituirani ili nesupstituirani heteroaril, supstituirani ili nesupstituirani heterociklilalkilni prsten, supstituirani ili nesupstituirani heteroarilalkil, supstituirani ili nesupstituirani heterociklički prsten, supstituirani ili nesupstituirani gvanidin;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema zahtjevu 1, formule (II) sa strukturom
[image]
gdje
R1 je vodik, (C1-C4)alkil, fenil, supstituirani fenil , piridin, ili supstituirani piridin,
X je CH2 ili C=O
R2 je H, (C1-C6)alkil, halogen, ili -O(C1-C6)alkil,
R3 je (C1-C6) alkil, cikloalkil, supstituirani cikloalkil, heterocikloalkil, aril, supstituirani aril, heteroaril, supstituirani heteroaril,
[image]
i gdje se supstituenti izabiru iz grupe koja obuhvaća C1-C4 linearni ili razgranati alkil, halo ili nitril supstituirani C1-C4 alkil, -O-alkil (C1-C4), halogen;
ili njegova farmaceutski prihvatljiva sol.
3. Spoj prema zahtjevu 1 ili 2, gdje se R3 izabire iz grupe koja obuhvaća:
[image]
[image]
[image]
[image]
[image]
4. Spoj prema bilo kojem od zahtjeva 1 do 3, gdje
R1 je supstituirani fenil ili supstituirani piridin,
X je CH2 ili C=O
R2 je H, CH3, Cl ili F
R3 se izabire iz grupe koja obuhvaća:
[image]
i
supstituirani fenil, gdje se supstituenti izabiru iz grupe koja obuhvaća Cl, F, Br, CF3 i CH3.
5. Spoj prema bilo kojem od zahtjeva 1 do 4, gdje
R1 se izabire iz grupe koja obuhvaća:
[image]
[image]
i
R3 se izabire iz grupe koja obuhvaća:
[image]
6. Spoj prema bilo kojem od zahtjeva 1 do 5, izabran iz grupe koja obuhvaća:
N-(4-Metil-3-{2-[4-(4-metil-piperazin-1-karbonil)-fenilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-fenil)-3-trifluorometil-benzamid
N-(4-Metil-3-{2-[4-(4-metil-piperazin-1-il)-fenilamino]-5-okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-fenil)-3-trifluorometil-benzamid
5-{6-[2-Metil-5-(3-trifluorometil-benzoilamino)-fenil]-5,6,7,8-tetrahidro-pirido[4,3-d]pirimidin-2-ilamino}-piridin-2-karboksilna kiselina ciklopropilamid
N-{3-[2-(4-Ciklopropilsulfamoil-fenilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-4-metil-fenil}-3-trifluorometil-benzamid
N-(4-Klor-3-{2-[4-(4-metil-piperazin-1-il)-fenilamino]-5-okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-fenil)-3-trifluorometil-benzamid
4-Trifluorometil-piridin-2-karboksilna kiselina {4-klor-3-[2-(4-metilkarbamoil-fenilamino)-7,8-dihidro-5Hpirido[4,3-d]pirimidin-6-il]-fenil}-amid
4,4,4-Trifluoro-3-metil-N-[4-metil-3-(2-{4-[2-(4-metil-piperazin-1-il)-etoksi]-fenilamino}-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il)-fenil]-butiramid
1-Ciklopentil-3-(4-metil-3-{2-[4-(2-pirolidin-1-il-etoksi)-fenilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-fenil)-urea
N-(4-Metil-3-{5-okso-2-[4-(2-pirolidin-1-il-etoksi)-fenilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-fenil)-3-trifluorometil-benzamid
N-{4-Klor-3-[2-(4-ciklopropilkarbamoilmetoksi-fenilamino)-5-
okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-fenil}-3-trifluorometil-benzamid
N-(4-Klor-3-{2-[3-metil-4-(4-metil-piperazin-1-il)-fenilamino]-5-okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-fenil)-3-trifluorometil-benzamid
3-Bromo-N-(4-metil-3-{2-[4-(4-metil-piperazin-1-il)-fenilamino]-5-okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-fenil)-benzamid
N-(4-Klor-3-{2-[4-(4-metil-piperazin-1-ilmetil)-fenilamino]-5-okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-fenil)-3-trifluorometil-benzamid
ili njegova farmaceutski prihvatljiva sol.
7. Spoj prema bilo kojem od zahtjeva 1 do 6, izabran iz grupe koja obuhvaća:
N-(4-Metil-3-{2-[4-(4-metil-piperazin-1-il)-fenilamino]-5-okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-fenil)-3-trifluorometil-benzamid
5-{6-[2-Metil-5-(3-trifluorometil-benzoilamino)-fenil]-5,6,7,8-tetrahidro-pirido[4,3-d]pirimidin-2-ilamino}-piridin-2-karboksilna kiselina ciklopropilamid
4-Trifluorometil-piridin-2-karboksilna kiselina {4-klor-3-[2-(4-metilkarbamoil-fenilamino)-7,8-dihidro-5Hpirido[4,3-d]pirimidin-6-il]-fenil}-amid
ili njegova farmaceutski prihvatljiva sol.
8. Spoj prema bilo kojem od zahtjeva 1 do 7, izabran iz grupe koja obuhvaća:
N-(4-Klor-3-{2-[3-metil-4-(4-metil-piperazin-1-il)-fenilamino]-5-okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-fenil)-3-trifluorometil-benzamid
N-{4-Klor-3-[2-(4-ciklopropilkarbamoilmetoksi-fenilamino)-5-okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-fenil}-3-trifluorometil-benzamid
ili njegova farmaceutski prihvatljiva sol.
9. Spoj prema bilo kojem od zahtjeva 1 do 8, za uporabu u terapiji.
10. Farmaceutska smjesa koja sadrži spoj prema bilo kojem od zahtjeva 1 do 8, i barem jednu farmaceutski prihvatljivu pomoćnu tvar, nosač ili punilo.
11. Spoj prema bilo kojem od zahtjeva 1 do 8, za uporabu u postupku za liječenje bolesti povezane s aktivacijom STAT3 mehanizma, kroz višeciljnu inhibiciju c-SRC i JAK2.
12. Spoj prema zahtjevu 11, gdje je ta bolest rak, autoimuna bolest, bolest kostiju i hematološke bolesti.
13. Spoj prema zahtjevu 12, gdje se kod raka radi o raku dojke, tumoru glave i vrata, melanomu, raku jajnika, raku pluća, raku gušterače, raku kolona, raku maternice, raku želuca, raku bubrega, raku mjehura, raku jetre i raku prostate, i gdje je taj spoj bilo koji spoj prema zahtjevu 7.
14. Spoj prema zahtjevu 12, gdje je rak multipli mijelom, leukemije, mijeloproliferativne neoplazme i limfomi i gdje je taj spoj bilo koji spoj prema zahtjevu 8.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN415CH2010 | 2010-02-17 | ||
| PCT/IB2011/050669 WO2011101806A1 (en) | 2010-02-17 | 2011-02-17 | Bicyclic compounds and their uses as dual c-src / jak inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20140437T1 true HRP20140437T1 (hr) | 2014-08-29 |
Family
ID=43903941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20140437AT HRP20140437T1 (hr) | 2010-02-17 | 2014-05-15 | Bicikliäśki spojevi i njihove uporabe kao dualnih c-src/jak inhibitora |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US8440679B2 (hr) |
| EP (1) | EP2536722B1 (hr) |
| JP (1) | JP2013519725A (hr) |
| KR (1) | KR20120130294A (hr) |
| CN (1) | CN102858770A (hr) |
| AR (1) | AR089641A1 (hr) |
| AU (1) | AU2011216895B2 (hr) |
| BR (1) | BR112012020639A2 (hr) |
| CA (1) | CA2789655A1 (hr) |
| CU (1) | CU20120118A7 (hr) |
| CY (1) | CY1115420T1 (hr) |
| DK (1) | DK2536722T3 (hr) |
| EA (1) | EA201290757A1 (hr) |
| ES (1) | ES2470190T3 (hr) |
| HK (1) | HK1178897A1 (hr) |
| HR (1) | HRP20140437T1 (hr) |
| IL (1) | IL221487A (hr) |
| MX (1) | MX2012009482A (hr) |
| NZ (1) | NZ602271A (hr) |
| PL (1) | PL2536722T3 (hr) |
| PT (1) | PT2536722E (hr) |
| RS (1) | RS53458B (hr) |
| SA (1) | SA111320200B1 (hr) |
| SG (1) | SG183329A1 (hr) |
| SI (1) | SI2536722T1 (hr) |
| SM (1) | SMT201400090B (hr) |
| TW (1) | TW201130838A (hr) |
| WO (1) | WO2011101806A1 (hr) |
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- 2014-05-15 HR HRP20140437AT patent/HRP20140437T1/hr unknown
- 2014-06-03 CY CY20141100393T patent/CY1115420T1/el unknown
- 2014-07-10 SM SM201400090T patent/SMT201400090B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR089641A1 (es) | 2014-09-10 |
| SA111320200B1 (ar) | 2014-02-16 |
| MX2012009482A (es) | 2012-11-29 |
| IL221487A (en) | 2014-11-30 |
| AU2011216895B2 (en) | 2015-11-05 |
| US20130143895A1 (en) | 2013-06-06 |
| TW201130838A (en) | 2011-09-16 |
| WO2011101806A1 (en) | 2011-08-25 |
| CN102858770A (zh) | 2013-01-02 |
| DK2536722T3 (da) | 2014-05-26 |
| RS53458B (en) | 2014-12-31 |
| JP2013519725A (ja) | 2013-05-30 |
| SI2536722T1 (sl) | 2014-10-30 |
| HK1178897A1 (en) | 2013-09-19 |
| ES2470190T3 (es) | 2014-06-23 |
| US20130012518A1 (en) | 2013-01-10 |
| BR112012020639A2 (pt) | 2017-08-08 |
| SG183329A1 (en) | 2012-09-27 |
| CU20120118A7 (es) | 2012-10-15 |
| CA2789655A1 (en) | 2011-08-25 |
| CY1115420T1 (el) | 2017-01-04 |
| PT2536722E (pt) | 2014-05-26 |
| US8440679B2 (en) | 2013-05-14 |
| EA201290757A1 (ru) | 2013-04-30 |
| KR20120130294A (ko) | 2012-11-30 |
| EP2536722A1 (en) | 2012-12-26 |
| NZ602271A (en) | 2013-09-27 |
| US8962637B2 (en) | 2015-02-24 |
| AU2011216895A1 (en) | 2012-09-27 |
| EP2536722B1 (en) | 2014-04-16 |
| PL2536722T3 (pl) | 2014-11-28 |
| SMT201400090B (it) | 2014-09-08 |
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