HRP20161763T1 - Derivati dihidropirazolopirimidinona - Google Patents
Derivati dihidropirazolopirimidinona Download PDFInfo
- Publication number
- HRP20161763T1 HRP20161763T1 HRP20161763TT HRP20161763T HRP20161763T1 HR P20161763 T1 HRP20161763 T1 HR P20161763T1 HR P20161763T T HRP20161763T T HR P20161763TT HR P20161763 T HRP20161763 T HR P20161763T HR P20161763 T1 HRP20161763 T1 HR P20161763T1
- Authority
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- Croatia
- Prior art keywords
- group
- lower alkyl
- alkyl group
- atom
- salt
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 claims 63
- 125000002947 alkylene group Chemical group 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000005843 halogen group Chemical group 0.000 claims 27
- 239000000824 cytostatic agent Substances 0.000 claims 25
- 230000001085 cytostatic effect Effects 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 21
- 150000002148 esters Chemical class 0.000 claims 20
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000002252 acyl group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000004434 sulfur atom Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 5
- 102000014150 Interferons Human genes 0.000 claims 4
- 108010050904 Interferons Proteins 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 4
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 239000000945 filler Substances 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- -1 S-1 Chemical compound 0.000 claims 3
- 230000002152 alkylating effect Effects 0.000 claims 3
- 239000003242 anti bacterial agent Substances 0.000 claims 3
- 229940088710 antibiotic agent Drugs 0.000 claims 3
- 230000008512 biological response Effects 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
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- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 2
- 230000000340 anti-metabolite Effects 0.000 claims 2
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- 239000002256 antimetabolite Substances 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
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- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 2
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- 229940047124 interferons Drugs 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
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- 238000002360 preparation method Methods 0.000 claims 2
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- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims 1
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims 1
- SIXNPTDIGGECMY-UHFFFAOYSA-N 1-[6-(1-hydroxy-2-methylpropan-2-yl)pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-propan-2-ylpyrazolo[3,4-d]pyrimidin-3-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C(=O)N(C(C)C)N1C1=CC=CC(C(C)(C)CO)=N1 SIXNPTDIGGECMY-UHFFFAOYSA-N 0.000 claims 1
- YXWIZDNGPJIRJQ-UHFFFAOYSA-N 1-[6-(2-hydroxypropan-2-yl)pyridin-2-yl]-6-[4-(1-methylpiperidin-4-yl)anilino]-2-propan-2-ylpyrazolo[3,4-d]pyrimidin-3-one Chemical compound C12=NC(NC=3C=CC(=CC=3)C3CCN(C)CC3)=NC=C2C(=O)N(C(C)C)N1C1=CC=CC(C(C)(C)O)=N1 YXWIZDNGPJIRJQ-UHFFFAOYSA-N 0.000 claims 1
- ISZVUZJIEBIZNI-UHFFFAOYSA-N 1-[6-(2-hydroxypropan-2-yl)pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-propan-2-ylpyrazolo[3,4-d]pyrimidin-3-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C(=O)N(C(C)C)N1C1=CC=CC(C(C)(C)O)=N1 ISZVUZJIEBIZNI-UHFFFAOYSA-N 0.000 claims 1
- 102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 claims 1
- WEIKOTSVYFTLLM-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-[6-(1-hydroxycyclobutyl)pyridin-2-yl]-6-[3-methyl-4-(4-methylpiperazin-1-yl)anilino]pyrazolo[3,4-d]pyrimidin-3-one Chemical compound C1CN(C)CCN1C(C(=C1)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)N(C=3N=C(C=CC=3)C3(O)CCC3)C2=N1 WEIKOTSVYFTLLM-UHFFFAOYSA-N 0.000 claims 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- RKPMUISFYCLVCI-UHFFFAOYSA-N 3-[2-ethyl-6-[3-methyl-4-(4-methylpiperazin-1-yl)anilino]-3-oxopyrazolo[3,4-d]pyrimidin-1-yl]-n,n-dimethylbenzamide Chemical compound C12=NC(NC=3C=C(C)C(N4CCN(C)CC4)=CC=3)=NC=C2C(=O)N(CC)N1C1=CC=CC(C(=O)N(C)C)=C1 RKPMUISFYCLVCI-UHFFFAOYSA-N 0.000 claims 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims 1
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- ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 claims 1
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- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims 1
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- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4162—1,2-Diazoles condensed with heterocyclic ring 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (22)
1. Spoj općenite formule (I):
[image]
gdje;
Ar1 je fenil, koji ima supstituent odabran iz grupe koju čine halogen atom, niža alkilna skupina, halo-niža alkilna skupina, hidroksi-niža alkilna skupina, niža alkoksi skupina, niža alkanoil skupina, hidroksi-niža alkilamino skupina, karbamoil skupina, hidroksi-niža alkilkarbamoil skupina, heteroaromatska skupina po izboru supstituirana nižom alkilnom skupinom, i skupina -Q1-A1-Q2-A2(R1a)R1b;
A1 je jednostruka veza, atom kisika ili atom sumpora, ili je imino skupina po izboru supstituirana nižom alkilnom skupinom;
A2 je atom dušika, ili je metin ili 1-vinil-2-iliden skupina po izboru supstituirana hidroksil skupinom, nižom alkilnom skupinom ili hidroksi-nižom alkilnom skupinom;
Q1 je jednostruka veza, karbonil skupina, ili metilen skupina po izboru supstituirana nižom alkilnom skupinom;
Q2 je jednostruka veza, ili etilen skupina po izboru supstituirana nižom alkilnom skupinom;
R1a i R1b su nezavisno atom vodika, niža alkilna skupina ili hidroksi-niža alkilna skupina, ili zajedno formiraju nižu alkilen skupinu gdje jedna ili više metilenskih skupina koje čine nižu alkilen skupinu mogu nezavisno biti zamijenjene atomom kisika, atomom sumpora, sulfinil skupinom, sulfonilom skupinom, karbonil skupinom, vinilen skupinom ili skupinom -N(R1c)-, i/ili supstituirane hidroksil skupinom ili nižom alkilnom skupinom;
R1c je atom vodika, niža alkenil skupina ili skupina -Q3-A3(R1d)R1e;
A3 je atom dušika, ili je metin ili 1-vinil-2-iliden skupina po izboru supstituirana hidroksil skupinom, nižom alkilnom skupinom ili hidroksi-nižom alkilnom skupinom;
Q3 je jednostruka veza ili niža alkilen skupina, gdje jedna ili više metilenskih skupina koje čine nižu alkilen skupinu mogu nezavisno biti zamijenjene atomom kisika, atomom sumpora, karbonil skupinom, sulfinil skupinom ili sulfonil skupinom, i/ili supstituirane atomom halogena, cijano skupinom, hidroksil skupinom ili nižom alkilnom skupinom;
R1d i R1e su nezavisno atom vodika, halogen atom, cijano skupina, hidroksil skupina, niža alkilna skupina ili hidroksi-niža alkilna skupina, ili zajedno formiraju nižu alkilen skupina gdje jedna ili više metilenskih skupina koje čine nižu alkilen skupinu mogu nezavisno biti zamijenjene atomom kisika, atomom sumpora, sulfinil skupinom, sulfonilom skupinom, karbonil skupinom, vinilen skupinom ili skupinom -N(R1f)-, i/ili supstituirane hidroksil skupinom ili nižom alkilnom skupinom;
R1f je atom vodika, niža alkilna skupina, halo-niža alkilna skupina, niža alkenil skupina ili niža alkanoil skupina;
R1 je niža alkilna skupina, niža alkenil skupina, niža alkinil skupina ili ciklo-niža alkilna skupina po izboru supstituirana halogen atomom, ili je aril skupina, aralkil skupina ili heteroaromatska skupina koja po izboru ima supstituent odabran iz grupe koju čine halogen atom, cijano skupina, amino skupina i niža alkilna skupina;
R2 je atom vodika, niža alkilna skupina, niža alkenil skupina ili niža alkinil skupina, ili je aril skupina, aralkil skupina ili heteroaromatska skupina koja po izboru ima supstituent odabran iz grupe koju čine halogen atom, cijano skupina, nitro skupina, karboksil skupina, skupina -Q4-A4(R1g)R1h i skupina -Q5-Ara, gdje jedna ili dvije ili više metilen skupina koje čine nižu alkilnu skupinu, nižu alkenil skupinu ili nižu alkinil skupinu mogu nezavisno biti zamijenjene atomom kisika, atomom sumpora, sulfinil skupinom, sulfonil skupinom, karbonil skupinom ili skupinom -N(R1j)-, i/ili supstituirane halogen atomom;
A4 je atom dušika, ili je metin skupina po izboru supstituirana halogen atomom, hidroksil skupinom, nižom alkilnom skupinom ili hidroksi-nižom alkilnom skupinom;
Ara je aril skupina ili heteroaromatska skupina, koja može imati supstituent odabran iz grupe koju čine halogen atom, niža alkilna skupina, halo-niža alkilna skupina, hidroksi-niža alkilna skupina i niža alkoksi skupina;
Q4 je jednostruka veza ili niža alkilen skupina, gdje jedna ili više metilenskih skupina koje čine nižu alkilen skupinu mogu nezavisno biti zamijenjene atomom kisika ili karbonil skupinom, i/ili supstituirane nižom alkilnom skupinom;
Q5 je jednostruka veza, atom kisika, atom sumpora, karbonil skupina ili niža alkilen skupina, gdje jedna ili više metilenskih skupina koje čine nižu alkilen skupinu mogu nezavisno biti zamijenjene atomom kisika, atomom sumpora ili karbonil skupinom, i/ili supstituirane halogen atomom ili nižom alkilnom skupinom;
R1g i R1h su nezavisno atom vodika, halogen atom, cijano skupina, hidroksil skupina, niža alkilna skupina, niža alkoksi-niža alkil skupina, niža alkanoil skupina, niža alkoksikarbonil skupina ili niža alkilsulfonil skupina, ili zajedno formiraju nižu alkilen skupinu, gdje jedna ili više metilenskih skupina koje čine nižu alkilen skupinu mogu nezavisno biti zamijenjene atomom kisika, atomom sumpora, sulfinil skupinom, sulfonil skupinom, karbonil skupinom ili skupinom -N(R1i)-, i/ili supstituirane halogen atomom ili nižom alkilnom skupinom;
R1i je atom vodika, niža alkilna skupina ili halo-niža alkilna skupina;
R1j je atom vodika ili niža alkilna skupina;
R3 je atom vodika ili niža alkilna skupina;
R4 je atom vodika, halogen atom, hidroksil skupina, niža alkilna skupina ili skupina -N(R1k)R1m;
R1k i R1m su nezavisno atom vodika ili niža alkilna skupina;
niža alkil skupina je linearna ili razgranata alkil skupina s 1 do 6 atoma ugljika;
niža alkoksi skupina je linearna ili razgranata alkoksi skupina s 1 do 6 atoma ugljika;
niža alkanoil skupina je alkanoil skupina s 2 do 7 atoma ugljika;
niža alkilen skupina je linearna ili razgranata alkilen skupina s 1 do 6 atoma ugljika;
niža alkenil skupina je linearna ili razgranata alkenil skupina s 2 do 6 atoma ugljika;
niža alkinil skupina je linearna ili razgranata alkinil skupina s 2 do 6 atoma ugljika i
ciklo-niža alkil skupina je cikloalkil skupina s 3 do 6 atoma ugljika; uz uvjet da su isključeni spojevi gdje je R1 metil skupina i R2 je nesupstituirana fenil skupina,
ili njegova sol ili ester.
2. Spoj općenite formule (I-1) prema zahtjevu 1, ili njegova sol ili ester:
[image]
gdje,
R5 i R6 su nezavisno atom vodika, halogen atom, niža alkilna skupina, halo-niža alkilna skupina, hidroksi-niža alkilna skupina, niža alkoksi skupina, niža alkanoil skupina, hidroksi-niža alkilamino skupina, karbamoil skupina ili hidroksi-niža alkilkarbamoil skupina;
R10 je niža alkilna skupina, niža alkenil skupina ili niža alkinil skupina, koje mogu biti supstituirane atomom halogena;
R20 je aril skupina ili heteroaromatska skupina, koje mogu imati supstituent odabran iz grupe koju čine halogen atom, cijano skupina, nitro skupina, karboksil skupina, skupina -Q4-A4(R1g)R1h i skupina -Q5-Ara; i
sve ostale skupine su kako su definirane u zahtjevu 1;
uz uvjet da su isključeni spojevi gdje je R10 metil skupina i R20 je nesupstituirana fenil skupina.
3. Spoj općenite formule (I-2) prema zahtjevu 1, ili njegova sol ili ester:
[image]
gdje,
R5 i R6 su nezavisno atom vodika, halogen atom, niža alkilna skupina, halo-niža alkilna skupina, hidroksi-niža alkilna skupina, niža alkoksi skupina, niža alkanoil skupina, hidroksi-niža alkilamino skupina, karbamoil skupina ili hidroksi-niža alkilkarbamoil skupina;
R11 je skupina formule (a-1) ili (a-2):
[image]
R7a, R7b, R8a i R8b su nezavisno atom vodika, halogen atom ili cijano skupina;
R8c je atom vodika ili niža alkilna skupina;
R20 je aril skupina ili heteroaromatska skupina, koje mogu imati supstituent odabran iz grupe koju čine halogen atom, cijano skupina, nitro skupina, karboksil skupina, skupina -Q4-A4(R1g)R1h i skupina -Q5-Ara; i
sve ostale skupine su kako su definirane u zahtjevu 1.
4. Spoj općenite formule (I-3) prema zahtjevu 1, ili njegova sol ili ester:
[image]
gdje,
R5 i R6 su nezavisno atom vodika, halogen atom, niža alkilna skupina, halo-niža alkilna skupina, hidroksi-niža alkilna skupina, niža alkoksi skupina, niža alkanoil skupina, hidroksi-niža alkilamino skupina, karbamoil skupina ili hidroksi-niža alkilkarbamoil skupina;
R12 je skupina formule (a-1):
[image]
R7a i R7b su nezavisno atom vodika, halogen atom ili cijano skupina;
R21 je niža alkilna skupina; i
sve druge varijable su kako su definirane u zahtjevu 1.
5. Spoj prema zahtjevu 2, ili njegova sol ili ester, gdje
R10 je niža alkilna skupina po izboru supstituirana halogen atomom; ili
R10 je niža alkenil ili niža alkinil skupina po izboru supstituirana halogen atomom; ili
R10 je niža alkenil po izboru supstituirana halogen atomom.
6. Spoj prema zahtjevu 5, ili njegova sol ili ester, gdje je R10 etil skupina ili izopropil skupina.
7. Spoj prema zahtjevu 5, ili njegova sol ili ester, gdje je R10 alil skupina, 2-metil-2-propenil skupina ili 3-metil-2-butenil skupina.
8. Spoj prema zahtjevu 2, ili njegova sol ili ester, gdje R20 je fenil skupina, tienil skupina, pirazolil skupina ili piridil skupina, koja može imati supstituent odabran iz grupe koju čine halogen atom, cijano skupina, nitro skupina, karboksil skupina, skupina -Q4-A4(R1g)R1h i skupina -Q5-Ara; ili R20je fenil ili piridil skupina sa skupinom -Q4-A4(R1g)R1h.
9. Spoj prema zahtjevu 2, ili njegova sol ili ester, gdje u skupini formule -Q1-A1-Q2-A2(R1a)R1b,
(i) A1, Q1 i Q2 su jednostruka veza, A2 je atom dušika, i R1a i R1b zajedno formiraju nižu alkilen skupinu gdje jedna ili dvije metilen skupine koje čine nižu alkilen skupinu mogu nezavisno biti zamijenjene atomom kisika, sulfonil skupinom, karbonil skupinom ili skupinom -N(R1c)-, i/ili supstituirane hidroksil skupinom;
(ii) A1, Q1 i Q2 su jednostruka veza, A2 je metin ili 1-vinil-2-iliden skupina po izboru supstituirana hidroksil skupinom, i R1a i R1b zajedno formiraju nižu alkilen skupinu gdje je jedna metilen skupina koja čini nižu alkilen skupinu zamijenjena skupinom -N(R1c)- ;
(iii) A1 je atom kisika, A2 je metin skupina, Q1 i Q2 su jednostruka veza, i R1a i R1b zajedno formiraju nižu alkilen skupinu gdje je jedna metilen skupina koja čini nižu alkilen skupinu zamijenjena skupinom -N(R1c)-;
(iv) A1 je atom kisika, A2 je atom dušika, Q1 je jednostruka veza, Q2 je etilen skupina, i R1a i R1b su nezavisno niža alkilna skupina; ili
(v) A1 i Q2 su jednostruka veza, A2 je atom dušika, Q1 je metilen skupina, i R1a i R1b su nezavisno niža alkilna skupina.
10. Spoj prema zahtjevu 2, ili njegova sol ili ester, gdje je R10 niža alkenil ili niža alkinil skupina po izboru supstituirana halogen atomom, R20 je fenil ili piridil skupina sa skupinom -Q4-A4(R1g)R1h, i skupina -Q1-A1-Q2-A2(R1a)R1b je odabrana prema formuli (aa1’):
[image]
11. Spoj prema zahtjevu 9 ili 10, ili njegova sol ili ester, gdje R1c je atom vodika ili skupina -Q3-A3(R1d)R1e, i u skupini -Q3-A3(R1d)R1e;
(i) A3 je metin skupina po izboru supstituirana hidroksil skupinom ili nižom alkilnom skupinom, Q3 je jednostruka veza, i R1d i R1e su nezavisno atom vodika ili niža alkilna skupina;
(ii) A3 je metin skupina, Q3 je jednostruka veza ili niža alkilen skupina, i R1d i R1e zajedno formiraju nižu alkilen skupinu gdje jedna metilen skupina koja čini nižu alkilen skupinu može biti zamijenjena skupinom -N(R1f)-;
(iii) A3 je metin skupina po izboru supstituirana hidroksil skupinom ili nižom alkilnom skupinom, Q3 je niža alkilen skupina gdje jedna ili dvije metilen skupine koje čine nižu alkilen skupinu mogu nezavisno biti zamijenjene atomom kisika, karbonil skupinom ili sulfonil skupinom, i/ili supstituirane hidroksil skupinom, i R1d i R1e su nezavisno atom vodika, halogen atom, cijano skupina ili niža alkilna skupina; ili
(iv) A3 je atom dušika, Q3 je niža alkilen skupina gdje je jedna metilen skupina koja čini nižu alkilen skupinu zamijenjena karbonil skupinom, i R1d i R1e su nezavisno atom vodika ili niža alkil skupina.
12. Spoj prema zahtjevu 1, ili njegova sol, koji je kako slijedi:
3-(2-etil-6-{[3-metil-4-(4-metilpiperazin-1-il)fenil]amino}-3-okso-1,2-dihidro-3H-pirazolo[3,4-d]pirimidin-1-il)-N,N-dimetilbenzamid,
2-benzil-6-{[3-metil-4-(4-metilpiperazin-1-il)fenil]amino}-1-fenil-1,2-dihidro-3H-pirazolo[3,4-d]pirimidin-3-on,
2-(2-klorofenil)-1-[6-(1-hidroksiciklobutil)piridin-2-il]-6-{[3-metil-4-(4-metilpiperazin-1-il)fenil]amino}-1,2-dihidro-3H-pirazolo[3,4-d]pirimidin-3-on,
1-[6-(1-hidroksi-1-metiletil)piridin-2-il]-2-izopropil-6-{[4-(4-metilpiperazin-1-il)fenil]amino}-1,2-dihidro-3H-pirazolo[3,4-d]pirimidin-3-on, ili
1-[6-(2-hidroksi-1,1-dimetiletil)piridin-2-il]-2-izopropil-6-{[4-(4-metilpiperazin-1-il)fenil]amino}-1,2-dihidro-3H-pirazolo[3,4-d]pirimidin-3-on.
13. Spoj prema zahtjevu 1, ili njegova sol, koji je 2-alil-6-{[3-(hidroksimetil)-4-(4-metilpiperazin-1-il)fenil]amino}-1-(3-tienil)-1,2-dihidro-3H-pirazolo[3,4-d]pirimidin-3-on.
14. Spoj prema zahtjevu 1, ili njegova sol, koji je 1-[6-(1-hidroksi-1-metiletil)piridin-2-il]-2-izopropil-6-{[4-(1-metilpiperidin-4-il)fenil]amino}-1,2-dihidro-3H-pirazolo[3,4-d]pirimidin-3-on.
15. Spoj prema zahtjevu 1, ili njegova sol, koji je 2-alil-1-[6-(3-metil-2-oksoimidazolidin-1-il)piridin-2-il]-6-{[4-(4-metilpiperazin-1-il)fenil]amino}-1,2-dihidro-3H-pirazolo[3,4-d]pirimidin-3-on.
16. Farmaceutski pripravak koji sadrži terapijski učinkovitu količinu spoja prema bilo kojem od prethodnih zahtjeva, ili njegovu sol ili ester, i farmaceutski prikladan nosač ili punilo.
17. Spoj prema bilo kojem od zahtjeva 1 do 15, ili njegova sol ili ester za uporabu u liječenju.
18. Spoj prema bilo kojem od zahtjeva 1 do 15, ili njegova sol ili ester za uporabu u liječenju raka.
19. Uporaba spoja prema bilo kojem od zahtjeva 1 do 15, ili njegova sol ili ester za proizvodnju lijeka za liječenje raka.
20. Kombinirani pripravak za istodobnu, odvojenu ili uzastopnu primjenu za uporabu u liječenju raka, obuhvaća sljedeća dva zasebna pripravka (a) i (b):
(a) pripravak koji sadrži, zajedno s farmaceutski prikladnim nosačem ili punilom, spoj prema bilo kojem od zahtjeva 1 do 15 ili njegovu farmaceutski prikladnu sol ili ester; i
(b) pripravak koji sadrži, zajedno s farmaceutski prikladnim nosačem ili punilom, jedno sredstvo protiv raka odabrano iz grupe koju čine alkilirajući citostatici, antimetaboliti citostatici, citostatici antibiotici, biljni citostatici, platinom-koordinirani kompleksni spojevi citostatici, citostatici derivati kamptotecina, citostatici inhibitori tirozin kinaze, monoklonska protutijela, interferoni, modulatori biološkog odgovora, i drugi citostatici ili njihova farmaceutski prikladna sol ili ester, gdje:
alkilirajući citostatici su N-oksid dušikovog plikavca, ciklofosfamid, ifosfamid, melfalan, busulfan, mitobronitol, karbokvon, tiotepa, ranimustin, nimustin, temozolomid, i karmustin;
antimetaboliti citostatici su metotreksat, 6-merkaptopurin ribozid, merkaptopurin, 5-fluorouracil, tegafur, doksifluridin, karmofur, citarabin, citarabin okfosfat, enocitabin, S-1, gemcitabin, fludarabin, i pemetreksed dinatrij;
citostatici antibiotici su aktinomicin D, doksorubicin, daunorubicin, neocarzinostatin, bleomicin, peplomicin, mitomicin C, aklarubicin, pirarubicin, epirubicin, zinostatin stimalamer, idarubicin, sirolimus, i valrubicin;
biljni citostatici su vinkristin, vinblastin, vindeshin, etopozid, sobuzoksan, docetaksel, paklitaksel, i vinorelbin;
platinom-koordinirani kompleksni spojevi citostatici su cisplatin, karboplatin, nedaplatin, i oksaliplatin;
citostatici derivati kamptotecina su irinotekan, topotekan, i kamptotecin;
citostatici inhibitori tirozin kinaze su gefitinib, imatinib, i erlotinib;
monoklonska protutijela su cetuksimab, bevacizumab, rituksimab, alemtuzumab, i trastuzumab;
interferoni su interferon α, interferon α-2a, interferon α-2b, interferon β, interferon γ-1a i interferon γ-n1,
modulatori biološkog odgovora su krestin, lentinan, sizofiran, picibanil, ili ubenimeks, i
drugi citostatici su mitoksantron, L-asparaginaza, prokarbazin, dakarbazin, hidroksikarbamid, pentostatin, tretinoin, alefacept, darbepoetin alfa, anastrozol, eksemestan, bicalutamid, leuprorelin, flutamid, fulvestrant, pegaptanib oktasodium, denileukin diftitoks, aldesleukin, tirotropin alfa, arsen trioksid, bortezomib, kapecitabin i goserelin.
21. Farmaceutski pripravak koji sadrži, zajedno s farmaceutski prikladnim nosačem ili punilom, spoj prema bilo kojem od zahtjeva 1 do 15, ili njegovu farmaceutski prikladnu sol ili ester; i citostatik odabran iz grupe koju čine alkilirajući citostatici, antimetaboliti citostatici, citostatici antibiotici, biljni citostatici, platinom-koordinirani kompleksni spojevi citostatici, citostatici derivati kamptotecina, citostatici inhibitori tirozin kinaze, monoklonska protutijela, modulatori biološkog odgovora, i drugi citostatici, gdje je definicija svake vrste citostatika kako je dano u zahtjevu 20, ili njihovu farmaceutski prikladnu sol ili ester.
22. Spoj prema bilo kojem od zahtjeva 1 do 15, ili njegova sol ili ester za uporabu kao senzibilizatora zračenja.
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| JP2006124208 | 2006-04-27 | ||
| PCT/JP2007/059416 WO2007126128A1 (ja) | 2006-04-27 | 2007-04-25 | ジヒドロピラゾロピリミジノン誘導体 |
| EP07742851.4A EP2017278B1 (en) | 2006-04-27 | 2007-04-25 | Dihydropyrazolopyrimidinone derivative |
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| MA (1) | MA30428B1 (hr) |
| MX (1) | MX2008013063A (hr) |
| MY (1) | MY145408A (hr) |
| NO (1) | NO341617B1 (hr) |
| NZ (1) | NZ571196A (hr) |
| PE (1) | PE20080695A1 (hr) |
| PL (2) | PL2017278T3 (hr) |
| PT (2) | PT2017278T (hr) |
| RU (1) | RU2437885C2 (hr) |
| SI (2) | SI2016080T1 (hr) |
| SV (1) | SV2009003060A (hr) |
| TW (1) | TWI409262B (hr) |
| UA (1) | UA96152C2 (hr) |
| WO (2) | WO2007126128A1 (hr) |
| ZA (1) | ZA200807748B (hr) |
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2009
- 2009-10-29 HK HK09110110.5A patent/HK1132498A1/xx unknown
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2010
- 2010-02-08 JP JP2010025458A patent/JP5167291B2/ja active Active
- 2010-10-18 HR HR20100563T patent/HRP20100563T1/hr unknown
- 2010-10-27 CY CY20101100973T patent/CY1111069T1/el unknown
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2011
- 2011-03-22 US US13/053,798 patent/US8791125B2/en active Active
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2014
- 2014-06-24 US US14/312,982 patent/US20140303178A1/en not_active Abandoned
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2016
- 2016-12-21 HR HRP20161763TT patent/HRP20161763T1/hr unknown
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2017
- 2017-01-27 CY CY20171100129T patent/CY1118526T1/el unknown
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