HRP20100572T1 - 6-heteroarilpiridoindolonski derivati, njihovo dobivanje i terapijska upotreba - Google Patents
6-heteroarilpiridoindolonski derivati, njihovo dobivanje i terapijska upotreba Download PDFInfo
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- HRP20100572T1 HRP20100572T1 HR20100572T HRP20100572T HRP20100572T1 HR P20100572 T1 HRP20100572 T1 HR P20100572T1 HR 20100572 T HR20100572 T HR 20100572T HR P20100572 T HRP20100572 T HR P20100572T HR P20100572 T1 HRP20100572 T1 HR P20100572T1
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- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 59
- -1 -SO2-R12 Chemical group 0.000 claims abstract 52
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 31
- 239000002253 acid Substances 0.000 claims abstract 16
- 150000003839 salts Chemical class 0.000 claims abstract 15
- 239000012453 solvate Substances 0.000 claims abstract 15
- 125000005843 halogen group Chemical group 0.000 claims abstract 13
- 125000001424 substituent group Chemical group 0.000 claims abstract 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 8
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 3
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims abstract 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 5
- 150000004677 hydrates Chemical class 0.000 claims 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000003211 malignant effect Effects 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical group C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 1
- JTQOJZXQILCGHT-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1,9-dimethyl-6-(1h-pyrazol-5-yl)pyrido[2,3-b]indol-2-one Chemical compound O=C1N(C)C=2N(C)C3=CC=C(C=4NN=CC=4)C=C3C=2C=C1C1=CC=C(Cl)C=C1Cl JTQOJZXQILCGHT-UHFFFAOYSA-N 0.000 claims 1
- CCQJUYFVPVBREI-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1,9-dimethyl-6-(2-methyl-1,3-oxazol-4-yl)pyrido[2,3-b]indol-2-one Chemical compound O1C(C)=NC(C=2C=C3C=4C=C(C(=O)N(C)C=4N(C)C3=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1 CCQJUYFVPVBREI-UHFFFAOYSA-N 0.000 claims 1
- NYDKDRFDXYNZFZ-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1,9-dimethyl-6-(2-methyl-1,3-oxazol-5-yl)pyrido[2,3-b]indol-2-one Chemical compound O1C(C)=NC=C1C1=CC=C(N(C)C2=C3C=C(C(=O)N2C)C=2C(=CC(Cl)=CC=2)Cl)C3=C1 NYDKDRFDXYNZFZ-UHFFFAOYSA-N 0.000 claims 1
- GCZKCOYBRBPHCI-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1,9-dimethyl-6-(2-methyl-1,3-thiazol-4-yl)pyrido[2,3-b]indol-2-one Chemical compound S1C(C)=NC(C=2C=C3C=4C=C(C(=O)N(C)C=4N(C)C3=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1 GCZKCOYBRBPHCI-UHFFFAOYSA-N 0.000 claims 1
- NTNYCYHROWMLKJ-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-6-[1-(2,2-dimethylpropanoyl)-4-methylpyrazol-3-yl]-1,9-dimethylpyrido[2,3-b]indol-2-one Chemical compound CC1=CN(C(=O)C(C)(C)C)N=C1C1=CC=C(N(C)C2=C3C=C(C(=O)N2C)C=2C(=CC(Cl)=CC=2)Cl)C3=C1 NTNYCYHROWMLKJ-UHFFFAOYSA-N 0.000 claims 1
- NWZSDAWYFMMQIJ-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-6-[1-(2,2-dimethylpropanoyl)pyrazol-3-yl]-1,9-dimethylpyrido[2,3-b]indol-2-one Chemical compound O=C1N(C)C=2N(C)C3=CC=C(C4=NN(C=C4)C(=O)C(C)(C)C)C=C3C=2C=C1C1=CC=C(Cl)C=C1Cl NWZSDAWYFMMQIJ-UHFFFAOYSA-N 0.000 claims 1
- QUWTVYLPASCIQS-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-6-[1-(methoxymethyl)pyrazol-3-yl]-1,9-dimethylpyrido[2,3-b]indol-2-one Chemical compound COCN1C=CC(C=2C=C3C=4C=C(C(=O)N(C)C=4N(C)C3=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=N1 QUWTVYLPASCIQS-UHFFFAOYSA-N 0.000 claims 1
- SDIYYSGFKAAZHI-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-6-[1-(methoxymethyl)triazol-4-yl]-1,9-dimethylpyrido[2,3-b]indol-2-one Chemical compound N1=NN(COC)C=C1C1=CC=C(N(C)C2=C3C=C(C(=O)N2C)C=2C(=CC(Cl)=CC=2)Cl)C3=C1 SDIYYSGFKAAZHI-UHFFFAOYSA-N 0.000 claims 1
- LUOKWCXJOWPAJS-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-6-[2-(ethoxymethyl)-1,3-thiazol-4-yl]-1,9-dimethylpyrido[2,3-b]indol-2-one Chemical compound S1C(COCC)=NC(C=2C=C3C=4C=C(C(=O)N(C)C=4N(C)C3=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1 LUOKWCXJOWPAJS-UHFFFAOYSA-N 0.000 claims 1
- KQJVRVDEILZHFW-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-6-[2-(hydroxymethyl)-1,3-thiazol-4-yl]-1-methyl-9h-pyrido[2,3-b]indol-2-one Chemical compound O=C1N(C)C=2NC3=CC=C(C=4N=C(CO)SC=4)C=C3C=2C=C1C1=CC=C(Cl)C=C1Cl KQJVRVDEILZHFW-UHFFFAOYSA-N 0.000 claims 1
- JRHOLBXHPIQLLL-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-6-[2-(methoxymethyl)-1,3-thiazol-4-yl]-1,9-dimethylpyrido[2,3-b]indol-2-one Chemical compound S1C(COC)=NC(C=2C=C3C=4C=C(C(=O)N(C)C=4N(C)C3=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1 JRHOLBXHPIQLLL-UHFFFAOYSA-N 0.000 claims 1
- JZDYXYKBWCZEDD-UHFFFAOYSA-N 3-(4-bromophenyl)-6-(1-ethylpyrazol-3-yl)-1,9-dimethylpyrido[2,3-b]indol-2-one Chemical compound CCN1C=CC(C=2C=C3C=4C=C(C(=O)N(C)C=4N(C)C3=CC=2)C=2C=CC(Br)=CC=2)=N1 JZDYXYKBWCZEDD-UHFFFAOYSA-N 0.000 claims 1
- FFPOMZICLTZMLU-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-[2-(ethoxymethyl)-1,3-thiazol-4-yl]-1,9-dimethylpyrido[2,3-b]indol-2-one Chemical compound S1C(COCC)=NC(C=2C=C3C=4C=C(C(=O)N(C)C=4N(C)C3=CC=2)C=2C=CC(Cl)=CC=2)=C1 FFPOMZICLTZMLU-UHFFFAOYSA-N 0.000 claims 1
- ZRVPREUDDRMGLE-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[1-(methoxymethyl)pyrazol-3-yl]-1,9-dimethylpyrido[2,3-b]indol-2-one Chemical compound COCN1C=CC(C=2C=C3C=4C=C(C(=O)N(C)C=4N(C)C3=CC=2)C=2C=CC(F)=CC=2)=N1 ZRVPREUDDRMGLE-UHFFFAOYSA-N 0.000 claims 1
- LYTLHZJJCCVEHX-UHFFFAOYSA-N 6-(2-amino-1,3-thiazol-5-yl)-3-(2-chloro-4-fluorophenyl)-1,9-dimethylpyrido[2,3-b]indol-2-one Chemical compound O=C1N(C)C=2N(C)C3=CC=C(C=4SC(N)=NC=4)C=C3C=2C=C1C1=CC=C(F)C=C1Cl LYTLHZJJCCVEHX-UHFFFAOYSA-N 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 206010004593 Bile duct cancer Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- GGLQUALFDAXJQF-UHFFFAOYSA-N CCOCC1=CC(=NN1C)C2=CC3=C(C=C2)N(C4=C3C=C(CN4C)C5=C(C=C(C=C5)Cl)Cl)C Chemical compound CCOCC1=CC(=NN1C)C2=CC3=C(C=C2)N(C4=C3C=C(CN4C)C5=C(C=C(C=C5)Cl)Cl)C GGLQUALFDAXJQF-UHFFFAOYSA-N 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 206010062767 Hypophysitis Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000034176 Neoplasms, Germ Cell and Embryonal Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 208000007452 Plasmacytoma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 201000000582 Retinoblastoma Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000000389 T-cell leukemia Diseases 0.000 claims 1
- 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006593 Urologic Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- MJERFLAKVFCILK-UHFFFAOYSA-N [4-[3-(2,4-dichlorophenyl)-1,9-dimethyl-2-oxopyrido[2,3-b]indol-6-yl]-1,3-thiazol-2-yl]methyl 2,2-dimethylpropanoate Chemical compound O=C1N(C)C=2N(C)C3=CC=C(C=4N=C(COC(=O)C(C)(C)C)SC=4)C=C3C=2C=C1C1=CC=C(Cl)C=C1Cl MJERFLAKVFCILK-UHFFFAOYSA-N 0.000 claims 1
- 210000004100 adrenal gland Anatomy 0.000 claims 1
- 208000026900 bile duct neoplasm Diseases 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 208000006990 cholangiocarcinoma Diseases 0.000 claims 1
- 201000000322 choriocarcinoma of ovary Diseases 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 210000001508 eye Anatomy 0.000 claims 1
- 210000001752 female genitalia Anatomy 0.000 claims 1
- 201000010175 gallbladder cancer Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 201000011066 hemangioma Diseases 0.000 claims 1
- 201000005787 hematologic cancer Diseases 0.000 claims 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 210000003026 hypopharynx Anatomy 0.000 claims 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims 1
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 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
- 210000000260 male genitalia Anatomy 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 210000002418 meninge Anatomy 0.000 claims 1
- 206010027191 meningioma Diseases 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 201000005962 mycosis fungoides Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 201000005987 myeloid sarcoma Diseases 0.000 claims 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 208000007538 neurilemmoma Diseases 0.000 claims 1
- 210000003300 oropharynx Anatomy 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 210000003635 pituitary gland Anatomy 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- 210000001625 seminal vesicle Anatomy 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 210000000813 small intestine Anatomy 0.000 claims 1
- 201000002314 small intestine cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 206010044412 transitional cell carcinoma Diseases 0.000 claims 1
- 210000004881 tumor cell Anatomy 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
- 201000010653 vesiculitis Diseases 0.000 claims 1
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 abstract 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (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)
Abstract
Spoj formule (I): naznacen time sto: • R1 je atom vodika ili (C1-C4)alkilna, CN, CF3 ili skupina CHF2;• R2 je atom vodika ili (C1-C4)alkilna skupina; • R3 je fenil, koji je nesupstituiran ili je supstituiran jednom ili vise puta, gdje se supstituente neovisno bira izmedu atoma halogena, (C1-C4)alkilne skupine i (C1-C4)alkoksi skupine; • R4 je heterociklicki radikal, kojeg se bira izmedu: • R5 je atom vodika, atom halogena, (C1-C4)alkilna skupina ili (C1-C4)alkoksi skupina; • R6 se bira izmedu atoma vodika, skupine -SO2-R12, (C1-C6)alkilne ili (C1-C6)mono- ili perfluoralkilne skupine, -(CH2)n-NR8R9,-(CH2)n-NH-CO-(C1-C4)alkilne skupine, -(CH2)n-NH-SO2-(C1-C4)alkilne skupine, skupine -(CH2)n-NH-(CH2)m-NR8R9,skupine -(CH2)n-NH-(CH2)m-OR10,skupine -(CH2)n-O-(CH2)m-NR8R9,-(CH2)n-O-(CH2)m-O-(C1-C4)alkilne skupine, skupine -(CH2)nHal, skupine -(C1-C6)alkil-O-R10,skupine -CO2-(CH2)m-O-R10,skupine -(CH2)n-COOR11, (C1-C6)alkilkarbonilne, (C1-C6)mono- ili perfluoralkilkarbonilne, -CO-NH-R10 ili -CO-(C1-C6)alkil-O-(C1-C4)alkilne skupine; • R7 se bira izmedu atoma vodika, (C1-C6)alkilne ili (C1-C6)mono- ili perfluoralkilne skupine, skupine -(CH2)n-NR8R9,-(CH2)n-NH-CO-(C1-C4)alkilne skupine, -(CH2)n-NH-SO2-(C1-C4)alkilne skupine, skupine -(CH2)n-NH-(CH2)m-NR8R9, skupine -(CH2)n-NH-(CH2)m-OR10, skupine -(CH2)n-O-(CH2)m-NR8R9,-(CH2)n-O-(CH2)m-O-(C1-C4)alkilne skupine, skupine -(CH2)nHal, skupine -(C1-C6)alkil-O-R10, skupine -CO2-(CH2)m-O-R10,skupine -(CH2)n-COOR11, (C1-C6)alkilkarbonilne, (C1-C6)mono- ili perfluoralkilkarbonilne, -CO-NH-R10 ili -CO-(C1-C6)alkil-O-(C1-C4)alkilne skupine; • svaki od R8 i R9, medusobno neovisno, atom vodika ili (C1-C4)alkilna skupina, ili R8 i R9, zajedno s atomom dusika na kojeg su vezani, tvore heterociklicki radikal, kojeg se bira izmedu pirolidin-1-ila, piperidin-1-ila, morfolin-4-ila ili piperazinila, izborno supstituiranog na svom drugom atomu dusika; • R10 je atom vodika, (C1-C4)alkilna skupina, (C1-C4)alkilkarbonilna skupina, (C3-C6)cikloalkilkarbonilna skupina, (C3-C6)cikloalkil(C1-C4)alkilkarbonilna skupina, (C3-C6)cikloalkilna skupina, (C5-C6)heterocikloalkilna skupina, (C1-C6)mono- ili perfluoralkilna skupina ili (C3-C6)cikloalkil(C1-C4)alkilna skupina; • R11 je atom vodika ili (C1-C6)alkilna skupina; • R12 je (C1-C6)alkilna skupina, (C1-C6)mono- ili perfluoralkilna skupina, cikloalkilna skupina, cikloalkilalkilna skupina ili (C1-C6)alkil-O-(C1-C4)alkilna skupina; • m je 1 ili 2• n je 0, 1 ili 2; • Hal je atom halogena; u obliku baze ili adicijske soli s kiselinom, te takoder u obliku hidrata ili solvata. Patent sadrzi jos 29 patentnih zahtjeva.
Claims (30)
1. Spoj formule (I):
[image]
naznačen time što:
• R1 je atom vodika ili (C1-C4)alkilna, CN, CF3 ili skupina CHF2;
• R2 je atom vodika ili (C1-C4)alkilna skupina;
• R3 je fenil, koji je nesupstituiran ili je supstituiran jednom ili više puta, gdje se supstituente neovisno bira između atoma halogena, (C1-C4)alkilne skupine i (C1-C4)alkoksi skupine;
• R4 je heterociklički radikal, kojeg se bira između:
[image]
• R5 je atom vodika, atom halogena, (C1-C4)alkilna skupina ili (C1-C4)alkoksi skupina;
• R6 se bira između atoma vodika, skupine -SO2-R12,
(C1-C6)alkilne ili (C1-C6)mono- ili perfluoralkilne skupine,
-(CH2)n-NR8R9,
-(CH2)n-NH-CO-(C1-C4)alkilne skupine,
-(CH2)n-NH-SO2-(C1-C4)alkilne skupine,
skupine -(CH2)n-NH-(CH2)m-NR8R9,
skupine -(CH2)n-NH-(CH2)m-OR10,
skupine -(CH2)n-O-(CH2)m-NR8R9,
-(CH2)n-O-(CH2)m-O-(C1-C4)alkilne skupine,
skupine -(CH2)nHal,
skupine -(C1-C6)alkil-O-R10,
skupine -CO2-(CH2)m-O-R10,
skupine -(CH2)n-COOR11,
(C1-C6)alkilkarbonilne, (C1-C6)mono- ili perfluoralkilkarbonilne, -CO-NH-R10 ili -CO-(C1-C6)alkil-O-(C1-C4)alkilne skupine;
• R7 se bira između atoma vodika,
(C1-C6)alkilne ili (C1-C6)mono- ili perfluoralkilne skupine, skupine -(CH2)n-NR8R9,
-(CH2)n-NH-CO-(C1-C4)alkilne skupine, -(CH2)n-NH-SO2-(C1-C4)alkilne skupine, skupine -(CH2)n-NH-(CH2)m-NR8R9, skupine -(CH2)n-NH-(CH2)m-OR10, skupine -(CH2)n-O-(CH2)m-NR8R9,
-(CH2)n-O-(CH2)m-O-(C1-C4)alkilne skupine, skupine -(CH2)nHal, skupine -(C1-C6)alkil-O-R10, skupine -CO2-(CH2)m-O-R10,
skupine -(CH2)n-COOR11,
(C1-C6)alkilkarbonilne, (C1-C6)mono- ili perfluoralkilkarbonilne, -CO-NH-R10 ili -CO-(C1-C6)alkil-O-(C1-C4)alkilne skupine;
• svaki od R8 i R9, međusobno neovisno, atom vodika ili (C1-C4)alkilna skupina, ili R8 i R9, zajedno s atomom dušika na kojeg su vezani, tvore heterociklički radikal, kojeg se bira između pirolidin-1-ila, piperidin-1-ila, morfolin-4-ila ili piperazinila, izborno supstituiranog na svom drugom atomu dušika;
• R10 je atom vodika, (C1-C4)alkilna skupina, (C1-C4)alkilkarbonilna skupina, (C3-C6)cikloalkilkarbonilna skupina, (C3-C6)cikloalkil(C1-C4)alkilkarbonilna skupina, (C3-C6)cikloalkilna skupina, (C5-C6)heterocikloalkilna skupina, (C1-C6)mono- ili perfluoralkilna skupina ili (C3-C6)cikloalkil(C1-C4)alkilna skupina;
• R11 je atom vodika ili (C1-C6)alkilna skupina;
• R12 je (C1-C6)alkilna skupina, (C1-C6)mono- ili perfluoralkilna skupina, cikloalkilna skupina, cikloalkilalkilna skupina ili (C1-C6)alkil-O-(C1-C4)alkilna skupina;
• m je 1 ili 2
• n je 0, 1 ili 2;
• Hal je atom halogena;
u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
2. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time što:
• R1 je atom vodika ili (C1-C4)alkilna skupina;
• R2 je atom vodika ili (C1-C4)alkilna skupina;
• R3 je fenil, koji je nesupstituiran ili je supstituiran jednom ili više puta, gdje se supstituente neovisno bira između atoma halogena, (C1-C4)alkilne skupine i (C1-C4)alkoksi skupine;
• R4 je heterociklički radikal, kojeg se bira između:
[image]
• R5 je atom vodika, atom halogena, (C1-C4)alkilna skupina ili (C1-C4)alkoksi skupina;
• R6 je atom vodika ili (C1-C4)alkilna skupina;
• R7 je atom vodika, (C1-C4)alkilna skupina, -(CH2)n-NR8R9 skupina, skupina -(CH2)nHal, skupina -CH2-OR10 ili skupina -(CH2)n-COOR11;
• svaki od R8 i R9, međusobno neovisno, atom vodika ili (C1-C4)alkilna skupina, ili R8 i R9, zajedno s atomom dušika na kojeg su vezani, tvore heterociklički radikal, kojeg se bira između pirolidin-1-ila, piperidin-1-ila ili morfolin-4-ila;
• R10 je atom vodika, (C1-C4)alkilna skupina, (C1-C4)alkilkarbonilna skupina ili (C3-C6)cikloalkilkarbonilna skupina;
• R11 je atom vodika ili (C1-C4)alkilna skupina;
• n je 0 ili 1;
• Hal je atom halogena;
u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
3. Spoj formule (IA) u skladu s patentnim zahtjevom 1 ili 2, naznačen time što R4 je 1,3-tiazol, supstituiran s R7, a supstituenti R1 do R7 su kao što je definirano u patentnom zahtjevu 1, u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
4. Spoj formule (IB) u skladu s patentnim zahtjevom 1 ili 2, naznačen time što R4 je 1,3,4-tiadiazol, supstituiran s R7, a supstituenti R1 do R7 su kao što je definirano u patentnom zahtjevu 1, u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
5. Spoj formule (IC) u skladu s patentnim zahtjevom 1 ili 2, naznačen time što R4 je 1,3-oksazol, supstituiran s R7, a supstituenti R1 do R7 su kao što je definirano u patentnom zahtjevu 1, u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
6. Spoj formule (ID) u skladu s patentnim zahtjevom 1 ili 2, naznačen time što R4 je izoksazol, supstituiran s R7, a supstituenti R1 do R7 su kao što je definirano u patentnom zahtjevu 1, u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
7. Spoj formule (IE) u skladu s patentnim zahtjevom 1 ili 2, naznačen time što R4 je 1H-pirazol, supstituiran s R6 i R7, a supstituenti R1 do R7 su kao što je definirano u patentnom zahtjevu 1, u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
8. Spoj formule (IF) u skladu s patentnim zahtjevom 1 ili 2, naznačen time što R4 je 1,2,3-triazol, supstituiran s R6 i R7, a supstituenti R1 do R7 su kao što je definirano u patentnom zahtjevu 1, u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
9. Spoj formule (I) u skladu s patentnim zahtjevom 1 ili 2, naznačen time što:
• R1 je atom vodika ili metil;
• R2 je metil;
• R3 je 2,4-diklorfenil;
• R4 je heterociklički radikal, kojeg se bira između:
[image]
• R5 je atom vodika;
• R6 je atom vodika, metil ili etil;
• R7 je atom vodika, metil, amino, metilamino, aminometil, (dimetilamino)metil, pirolidin-1-ilmetil, klormetil, hidroksimetil, etoksimetil, [(2,2-dimetilpropanoil)oksi]metil, [(ciklopropilkarbonil)oksi]metil, metoksikarbonil, 2-metoksi-2-oksoetil ili karboksimetil;
u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
10. Spoj formule (I) u skladu s patentnim zahtjevom 1 ili 2, naznačen time što:
• R1 je atom vodika ili metil;
• R2 je metil;
• R3 je 2,4-diklorfenil;
• R4 je:
• 2-metil-1,3-tiazol-4-il, 2-amino-1,3-tiazol-4-il, 2-(metilamino)-1,3-tiazol-4-il, 2-(hidroksimetil)-1,3-tiazol-4-il, 2-(etoksimetil)-1,3-tiazol-4-il, 2-[[(2,2-dimetilpropanoil)oksi]metil]-1,3-tiazol-4-il ili 2-[(ciklopropilkarbonil)oksi]metil;
• 1,3-tiazol-2-il, 4-metil-1,3-tiazol-2-il, 4-amino-1,3-tiazol-2-il, 4-(aminometil)-1,3-tiazol-2-il, 4-[(dimetilamino)metil]-1,3-tiazol-2-il, 4-(pirolidin-1-ilmetil)-1,3-tiazol-2-il, 4-(klormetil)-1,3-tiazol-2-il, 4-(2-metoksi-2-oksoetil)-1,3-tiazol-2-il ili 4-(karboksimetil)-1,3-tiazol-2-il;
• 1,3-oksazol-4-il, 2-metil-1,3-oksazol-4-il, 2-amino-1,3-oksazol-4-il, 2-(hidroksimetil)-1,3-oksazol-4-il, 2-(etoksimetil)-1,3-oksazol-4-il ili 2-[[(2,2-dimetilpropanoil)oksi]metil]-1,3-oksazol-4-il;
• 1,3-oksazol-5-il, 2-metil-1,3-oksazol-5-il ili 2-(etoksimetil)-1,3-oksazol-5-il;
• 1,3-oksazol-2-il, 4-metil-1,3-oksazol-2-il ili 5-metil-1,3-oksazol-2-il;
• an izoksazol-5-il, 4-metilizoksazol-5-il ili 3-(metoksikarbonil)izoksazol-5-il;
• 1H-pirazol-5-il, 1-etil-1H-pirazol-5-il, 3-(metoksikarbonil)-1H-pirazol-5-il, 3-metil-1H-pirazol-5-il ili 3-amino-1H-pirazol-5-il;
• 1-metil-1H-pirazol-3-il ili 1-etil-1H-pirazol-3-il;
• 3-amino-1H-pirazol-4-il;
• 5-amino-1,3,4-tiadiazol-2-il;
• 1H-1,2,3-triazol-4-il;
• R5 je atom vodika;
u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
11. Spoj, naznačen time što ga se bira između:
• 6-(2-amino-1,3-tiazol-4-il)-3-(2,4-diklorfenil)-1-metil-1,9-dihidro-2H-pirido[2,3-b]indol-2-ona;
• 3-(2,4-diklorfenil)-6-[2-(hidroksimetil)-1,3-tiazol-4-il]-1-metil-1,9-dihidro-2H-pirido[2,3-b]indol-2-ona;
• 3-(2,4-diklorfenil)-1,9-dimetil-6-(2-metil-1,3-tiazol-4-il)-1,9-dihidro-2H-pirido[2,3-b]indol-2-ona;
• [4-[3-(2,4-diklorfenil)-1,9-dimetil-2-okso-2,9-dihidro-1H-pirido[2,3-b]indol-6-il]-1,3-tiazol-2-il]metil-pivalata;
• 3-(2,4-diklorfenil)-6-[2-(etoksimetil)-1,3-tiazol-4-il]-1,9-dimetil-1,9-dihidro-2H-pirido[2,3-b]indol-2-ona;
• 3-(2,4-diklorfenil)-1,9-dimetil-6-(2-metil-1,3-oksazol-4-il)-1,9-dihidro-2H-pirido[2,3-b]indol-2-ona;
• 3-(2,4-diklorfenil)-1,9-dimetil-6-(2-metil-1,3-oksazol-5-il)-1,9-dihidro-2H-pirido[2,3-b]indol-2-ona;
• 6-(3-amino-1H-pirazol-5-il)-3-(2,4-diklorfenil)-1,9-dimetil-1,9-dihidro-2H-pirido[2,3-b]indol-2-ona;
• 6-[4-(aminometil)-1,3-tiazol-2-il]-3-(2,4-diklorfenil)-1,9.-dimetil-1,9-dihidro-2H-pirido[2,3-b]indol-2-ona;
• 6-(3-amino-1H-pirazol-4-il)-3-(2,4-diklorfenil)-1,9-dimetil-1,9-dihidro-2H-pirido[2,3-b]indol-2-ona;
• 3-(2,4-diklorfenil)-1,9-dimetil-6-(1H-pirazol-5-il)-1,9-dihidro-2H-pirido[2,3-b]indol-2-ona;
• 3-(2,4-diklorfenil)-6-(1-metoksimetil-1H-pirazol-3-il)-1,9-dimetil-1,9-dihidropirido[2,3-b]indol-2-ona;
• 3-(4-bromfenil)-6-(1-etil-1H-pirazol-3-il)-1,9-dimetil-1,9-dihidropirido[2,3-b]indol-2-ona;
• 6-(2-aminotiazol-5-il)-3-(2-klor-4-fluorfenil)-1,9-dimetil-1,9-dihidropirido[2,3-b]indol-2-ona;
• 3-(2,4-diklorfenil)-6-(2-metoksimetiltiazol-4-il)-1,9-dimetil-1,9-dihidropirido[2,3-b]indol-2-ona;
• 3-(2,4-diklorfenil)-6-[1-(2,2-dimetilpropionil)-4-metil-1H-pirazol-3-il]-1,9-dimetil-1,9-dihidropirido[2,3-b]indol-2-ona;
• 3-(2,4-diklorfenil)-6-(5-etoksimetil-1-metil-1H-pirazol-3-il)-1,9-dimetil-1,9-dihidropirido[2,3-b]indol-2-ona;
• 3-(4-fluorfenil)-6-(1-metoksimetil-1H-pirazol-3-il)-1,9-dimetil-1,9-dihidropirido[2,3-b]indol-2-ona;
• 3-(4-fluorfenil)-6-(1-metoksimetil-4-metil-1H-pirazol-3-il)-1,9-dimetil-1,9-dihidropirido[2,3-b]indol-2-ona;
• 3-(4-klorfenil)-6-(2-etoksimetiltiazol-4-il)-1,9-dimetil-1,9-dihidropirido[2,3-b]indol-2-ona;
• 3-(2,4-diklorfenil)-6-[1-(2,2-dimetilpropionil)-1H-pirazol-3-il]-1,9-dimetil-1,9-dihidropirido[2,3-b]indol-2-ona;
• 3-(2,4-diklorfenil)-6-(1-metoksimetil-1H-[1,2,3]triazol-4-il)-1,9-dimetil-1,9-dihidropirido[2,3-b]indol-2-on
u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
12. Spoj formule:
[image]
naznačen time što:
• R1 predstavlja H, a R4 se bira između:
[image]
ili
• R1 predstavlja Me, a R4 se bira između:
[image]
[image]
[image]
gdje su upotrijebljene sljedeće kratice: Me: metil; Et: etil i t-Bu: tert-butil.
13. Spoj u skladu s patentnim zahtjevom 12, naznačen time što je u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
14. Postupak dobivanja spojeva formule (IA) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što:
spoj formule:
[image]
u kojoj su R1, R2, R3 i R5 kao što je definirano u patentnom zahtjevu 1, a Hal je atom vodika, reagira sa spojem formule:
[image]
u kojoj R7 je kao što je definirano u patentnom zahtjevu 1.
15. Postupak dobivanja spojeva formule (IA) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što spoj formule:
[image]
u kojoj su R1, R2, R3 i R5 kao što je definirano u patentnom zahtjevu 1, reagira sa spojem formule:
[image]
u kojoj R7 je kao što je definirano u patentnom zahtjevu 1, a Hal je atom halogena.
16. Postupak dobivanja spojeva formule (IB) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što
spoj formule:
[image]
u kojoj su R1, R2, R3 i R5 kao što je definirano u patentnom zahtjevu 1, reagira sa spojem formule:
[image]
u kojoj R7 je kao što je definirano u patentnom zahtjevu 1.
17. Postupak dobivanja spojeva formule (IC) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što
spoj formule:
[image]
u kojoj su R1, R2, R3 i R5 kao što je definirano u patentnom zahtjevu 1, a Hal je atom halogena, reagira sa spojem formule:
[image]
u kojoj R7 je kao što je definirano u patentnom zahtjevu 1.
18. Postupak dobivanja spojeva formule (IC) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što
A) spoj formule:
[image]
u kojoj R1, R2, R3 i R5 su kao što je definirano u patentnom zahtjevu 1, reagira s funkcionalnim derivatom kiseline formule:
[image]
u kojoj R7 je kao što je definirano u patentnom zahtjevu 1, kako bi se dobilo spoj formule:
[image]
B) tako dobiveni spoj formule (XII) se ciklizira djelovanjem kiseline.
19. Postupak dobivanja spojeva formule (IC) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što
spoj formule:
[image]
u kojoj su R1, R2, R3 i R5 kao što je definirano u patentnom zahtjevu 1, reagira sa spojem formule:
[image]
u kojoj R7 je kao što je definirano u patentnom zahtjevu 1, a Hal je atom halogena.
20. Postupak dobivanja spojeva formule (IC) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što
spoj formule:
[image]
u kojoj su R1, R2, R3 i R5 kao što je definirano u patentnom zahtjevu 1, reagira sa spojem formule:
[image]
u kojoj R7 je kao što je definirano u patentnom zahtjevu 1, a Hal je atom halogena.
21. Postupak dobivanja spojeva formule (ID) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što
spoj formule:
[image]
u kojoj R1, R2, R3, R5 i R7 su kao što je definirano u patentnom zahtjevu 1, reagira s hidroksilaminom.
22. Postupak dobivanja spojeva formule (ID) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što spoj formule (XX):
[image]
u kojoj R1, R2 i R3 su kao što je definirano u patentnom zahtjevu 1, reagira s hidroksilaminom.
23. Postupak dobivanja spojeva formule (ID) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što
spoj formule:
[image]
u kojoj R1, R2, R3, R5 i R7 su kao što je definirano u patentnom zahtjevu 1, reagira s hidroksilaminom.
24. Postupak dobivanja spojeva formule (IE) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što
spoj formule:
[image]
u kojoj R1, R2, R3, R5 i R7 su kao što je definirano u patentnom zahtjevu 1, reagira sa spojem formule:
NH2-NH-R6 (XIX)
u kojoj R6 je kao što je definirano u patentnom zahtjevu 1.
25. Postupak dobivanja spojeva formule (IE) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što
spoj formule:
[image]
u kojoj R1, R2, R3, R5 i R7 su kao što je definirano u patentnom zahtjevu 1, reagira s hidrazinom formule:
NH2-NH-R6 (XIX).
26. Postupak dobivanja spojeva formule (IF) u skladu s patentnim zahtjevom 1, gdje
[image]
naznačen time što
spoj formule (XXII):
[image]
u kojoj su R1, R2, R3 i R5 kao što je definirano za spoj formule (I) u patentnom zahtjevu 1, reagira s natrijevim azidom.
27. Medikament, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 13, ili adicijsku sol navedenog spoja s farmaceutski prihvatljivom kiselinom, ili hidrat ili solvat spoja formule (I).
28. Farmaceutski pripravak, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 13, ili farmaceutski prihvatljivu sol, hidrat ili solvat navedenog spoja, te također najmanje jednu farmaceutski prihvatljivu pomoćnu tvar.
29. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 13, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju i sprječavanju bolesti uzrokovanih ili pogoršanih proliferacijom tumorskih stanica.
30. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 13, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju raka dojke; raka pluća; raka tankog crijeva, raka debelog crijeva i rektuma; raka dišnih puteva, orofarinksa i hipofarinksa; raka; raka jetre, raka želuca, raka žučovoda, raka žučnog mjehura, raka gušterače; raka mokraćnog sustava, uključujući rak bubrega, rak urotela i rak mokraćnog mjehura; raka ženskih genitalija, uključujući rak maternice, rak vrata maternice, rak jajnika, koriokarcinom i trofoblastom; raka muških genitalija, uključujući rak prostate, rak sjemenih mjehurića, rak testisa, tumore germinativnih stanica; raka endokrinih žlijezda, uključujući rak štitnjače, hipofize, nadbubrežne žlijezde; raka kože, uključujući hemangiome, melanome, sarkome, uključujući Kaposijev sarkom; tumora na mozgu, tumora živaca, očiju, moždanih ovojnica, uključujući astrocitome, gliome, glioblastome, retinoblastome, neurinome, neuroblastome, leurilemome, meningiome; tumora koji potiču od zloćudnih hematopoetskih tumora, uključujući leukemije, klorome, plazmacitome, fungoidnu mikozu, leukemiju T-stanica ili limfom, ne-Hodgkinov limfom, zloćudne hematopatije, mijelome.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0510730A FR2892416B1 (fr) | 2005-10-20 | 2005-10-20 | Derives de 6-heteroarylpyridoindolone, leur preparation et leur application en therapeutique |
| PCT/FR2006/002330 WO2007045758A1 (fr) | 2005-10-20 | 2006-10-17 | Derives de 6-heteroarylpyridoindolone, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100572T1 true HRP20100572T1 (hr) | 2011-01-31 |
Family
ID=35953891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100572T HRP20100572T1 (hr) | 2005-10-20 | 2010-10-19 | 6-heteroarilpiridoindolonski derivati, njihovo dobivanje i terapijska upotreba |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US8063061B2 (hr) |
| EP (1) | EP1940840B1 (hr) |
| JP (1) | JP2009512666A (hr) |
| KR (1) | KR20080057300A (hr) |
| CN (1) | CN101312970A (hr) |
| AR (1) | AR056874A1 (hr) |
| AT (1) | ATE474840T1 (hr) |
| AU (1) | AU2006303210A1 (hr) |
| BR (1) | BRPI0617684A2 (hr) |
| CA (1) | CA2625502C (hr) |
| CR (1) | CR9873A (hr) |
| CY (1) | CY1110891T1 (hr) |
| DE (1) | DE602006015675D1 (hr) |
| DK (1) | DK1940840T3 (hr) |
| DO (1) | DOP2006000225A (hr) |
| EA (1) | EA014873B1 (hr) |
| EC (1) | ECSP088370A (hr) |
| ES (1) | ES2348745T3 (hr) |
| FR (1) | FR2892416B1 (hr) |
| GT (1) | GT200600462A (hr) |
| HR (1) | HRP20100572T1 (hr) |
| IL (1) | IL190519A0 (hr) |
| MA (1) | MA29961B1 (hr) |
| NO (1) | NO20082226L (hr) |
| PE (1) | PE20070591A1 (hr) |
| PL (1) | PL1940840T3 (hr) |
| PT (1) | PT1940840E (hr) |
| SI (1) | SI1940840T1 (hr) |
| TN (1) | TNSN08161A1 (hr) |
| TW (1) | TW200734336A (hr) |
| UY (1) | UY29879A1 (hr) |
| WO (1) | WO2007045758A1 (hr) |
| ZA (1) | ZA200803445B (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2823975B1 (fr) | 2001-04-27 | 2003-05-30 | Sanofi Synthelabo | Nouvelle utilisation de pyridoindolone |
| US7456193B2 (en) | 2002-10-23 | 2008-11-25 | Sanofi-Aventis | Pyridoindolone derivatives substituted in the 3-position by a heterocyclic group, their preparation and their application in therapeutics |
| FR2846329B1 (fr) | 2002-10-23 | 2004-12-03 | Sanofi Synthelabo | Derives de pyridoindolone substitues en -3 par un phenyle, leur preparation et leur application en therapeutique |
| FR2869316B1 (fr) | 2004-04-21 | 2006-06-02 | Sanofi Synthelabo | Derives de pyridoindolone substitues en -6, leur preparation et leur application en therapeutique. |
| CA2873658C (en) | 2012-05-17 | 2021-01-26 | Genentech, Inc. | Process for making amino acid compounds |
| CN105793252B (zh) | 2013-12-13 | 2018-01-30 | 豪夫迈·罗氏有限公司 | 布鲁顿氏酪氨酸激酶抑制剂 |
| KR101822767B1 (ko) | 2013-12-13 | 2018-01-26 | 에프. 호프만-라 로슈 아게 | 브루톤 티로신 키나아제의 억제제 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1268772A (en) | 1968-03-15 | 1972-03-29 | Glaxo Lab Ltd | NOVEL alpha-CARBOLINE DERIVATIVES, THE PREPARATION THEREOF AND COMPOSITIONS CONTAINING THE SAME |
| US4263304A (en) | 1978-06-05 | 1981-04-21 | Sumitomo Chemical Company, Limited | 7 H-indolo[2,3-c]isoquinolines |
| SU833971A1 (ru) | 1979-07-10 | 1981-05-30 | Ленинградский Химико-Фармацевтическийинститут | Способ получени 3-фенил-2-оксо- - КАРбОлиНОВ |
| FR2595701B1 (fr) | 1986-03-17 | 1988-07-01 | Sanofi Sa | Derives du pyrido-indole, leur application a titre de medicaments et les compositions les renfermant |
| ATE386131T1 (de) | 1994-04-13 | 2008-03-15 | Univ Rockefeller | Aav-vermittelte überbringung von dna in zellen des nervensystems |
| DE19502753A1 (de) | 1995-01-23 | 1996-07-25 | Schering Ag | Neue 9H-Pyrido[3,4-b]indol-Derivate |
| FR2765581B1 (fr) | 1997-07-03 | 1999-08-06 | Synthelabo | Derives de 3-aryl-1,9-dihydro-2h-pyrido[2,3-b]indol-2-one, leur preparation et leur application en therapeutique |
| FR2765582B1 (fr) | 1997-07-03 | 1999-08-06 | Synthelabo | Derives de 3-alkyl-1,9-dihydro-2h-pyrido[2,3-b]indol-2-one leur preparation et leur application en therapeutique |
| AU3375999A (en) | 1998-04-02 | 1999-10-25 | Neurogen Corporation | Aminoalkyl substituted 5,6,7,8-tetrahydro-9h pyrimidino(2,3-b)indole and 5,6,7,8-tetrahydro-9h-pyrimidino(4,5-b)indole derivatives: crf1 specific ligands |
| IT1313592B1 (it) | 1999-08-03 | 2002-09-09 | Novuspharma Spa | Derivati di 1h-pirido 3,4-b indol-1-one. |
| US20020156016A1 (en) | 2001-03-30 | 2002-10-24 | Gerald Minuk | Control of cell growth by altering cell membrane potentials |
| FR2823975B1 (fr) | 2001-04-27 | 2003-05-30 | Sanofi Synthelabo | Nouvelle utilisation de pyridoindolone |
| US7456193B2 (en) | 2002-10-23 | 2008-11-25 | Sanofi-Aventis | Pyridoindolone derivatives substituted in the 3-position by a heterocyclic group, their preparation and their application in therapeutics |
| FR2846329B1 (fr) * | 2002-10-23 | 2004-12-03 | Sanofi Synthelabo | Derives de pyridoindolone substitues en -3 par un phenyle, leur preparation et leur application en therapeutique |
| FR2846330B1 (fr) * | 2002-10-23 | 2004-12-03 | Sanofi Synthelabo | Derives de pyridoindolone substitues en -3 par groupe heterocyclique, leur preparation et leur application en therapeutique |
| FR2869316B1 (fr) | 2004-04-21 | 2006-06-02 | Sanofi Synthelabo | Derives de pyridoindolone substitues en -6, leur preparation et leur application en therapeutique. |
-
2005
- 2005-10-20 FR FR0510730A patent/FR2892416B1/fr not_active Expired - Fee Related
-
2006
- 2006-10-05 PE PE2006001217A patent/PE20070591A1/es not_active Application Discontinuation
- 2006-10-16 DO DO2006000225A patent/DOP2006000225A/es unknown
- 2006-10-17 AT AT06830970T patent/ATE474840T1/de active
- 2006-10-17 EA EA200801123A patent/EA014873B1/ru not_active IP Right Cessation
- 2006-10-17 BR BRPI0617684-4A patent/BRPI0617684A2/pt not_active IP Right Cessation
- 2006-10-17 DE DE602006015675T patent/DE602006015675D1/de active Active
- 2006-10-17 CA CA2625502A patent/CA2625502C/fr not_active Expired - Fee Related
- 2006-10-17 ES ES06830970T patent/ES2348745T3/es active Active
- 2006-10-17 CN CNA2006800433247A patent/CN101312970A/zh active Pending
- 2006-10-17 SI SI200630800T patent/SI1940840T1/sl unknown
- 2006-10-17 KR KR1020087009373A patent/KR20080057300A/ko not_active Application Discontinuation
- 2006-10-17 ZA ZA200803445A patent/ZA200803445B/xx unknown
- 2006-10-17 EP EP06830970A patent/EP1940840B1/fr active Active
- 2006-10-17 WO PCT/FR2006/002330 patent/WO2007045758A1/fr active Application Filing
- 2006-10-17 JP JP2008536081A patent/JP2009512666A/ja not_active Withdrawn
- 2006-10-17 GT GT200600462A patent/GT200600462A/es unknown
- 2006-10-17 DK DK06830970.7T patent/DK1940840T3/da active
- 2006-10-17 PL PL06830970T patent/PL1940840T3/pl unknown
- 2006-10-17 AU AU2006303210A patent/AU2006303210A1/en not_active Abandoned
- 2006-10-17 PT PT06830970T patent/PT1940840E/pt unknown
- 2006-10-18 AR ARP060104538A patent/AR056874A1/es unknown
- 2006-10-19 TW TW095138582A patent/TW200734336A/zh unknown
- 2006-10-20 UY UY29879A patent/UY29879A1/es unknown
-
2008
- 2008-03-30 IL IL190519A patent/IL190519A0/en unknown
- 2008-04-08 CR CR9873A patent/CR9873A/es not_active Application Discontinuation
- 2008-04-09 US US12/100,079 patent/US8063061B2/en not_active Expired - Fee Related
- 2008-04-10 TN TNP2008000161A patent/TNSN08161A1/en unknown
- 2008-04-15 EC EC2008008370A patent/ECSP088370A/es unknown
- 2008-05-14 NO NO20082226A patent/NO20082226L/no not_active Application Discontinuation
- 2008-05-19 MA MA30945A patent/MA29961B1/fr unknown
-
2010
- 2010-10-13 CY CY20101100910T patent/CY1110891T1/el unknown
- 2010-10-19 HR HR20100572T patent/HRP20100572T1/hr unknown
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