HRP20100650T2 - Derivati maleimida, farmaceutski pripravci i postupci liječenja raka - Google Patents
Derivati maleimida, farmaceutski pripravci i postupci liječenja raka Download PDFInfo
- Publication number
- HRP20100650T2 HRP20100650T2 HR20100650T HRP20100650T HRP20100650T2 HR P20100650 T2 HRP20100650 T2 HR P20100650T2 HR 20100650 T HR20100650 T HR 20100650T HR P20100650 T HRP20100650 T HR P20100650T HR P20100650 T2 HRP20100650 T2 HR P20100650T2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- group
- aryl
- cancer
- dione
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title claims abstract 10
- 201000011510 cancer Diseases 0.000 title claims abstract 9
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 3
- 230000002062 proliferating effect Effects 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- UCEQXRCJXIVODC-PMACEKPBSA-N LSM-1131 Chemical compound C1CCC2=CC=CC3=C2N1C=C3[C@@H]1C(=O)NC(=O)[C@H]1C1=CNC2=CC=CC=C12 UCEQXRCJXIVODC-PMACEKPBSA-N 0.000 claims 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims 7
- 208000035269 cancer or benign tumor Diseases 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical group OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 5
- 210000000481 breast Anatomy 0.000 claims 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims 5
- UCEQXRCJXIVODC-UXHICEINSA-N (+)-cis-3-(5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinolin-1-yl)-4(1h-indol-3-yl)pyrrolidine-2,5-dione Chemical compound C1CCC2=CC=CC3=C2N1C=C3[C@@H]1C(=O)NC(=O)[C@@H]1C1=CNC2=CC=CC=C12 UCEQXRCJXIVODC-UXHICEINSA-N 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical group OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 3
- 206010006187 Breast cancer Diseases 0.000 claims 3
- 208000026310 Breast neoplasm Diseases 0.000 claims 3
- 239000004471 Glycine Chemical group 0.000 claims 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical group SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 3
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical group OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 3
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical group OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical group OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 3
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical group OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical group OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical group CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 3
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical group CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical group NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical group CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical group C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical group OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical group CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 3
- 208000006994 Precancerous Conditions Diseases 0.000 claims 3
- 125000000539 amino acid group Chemical group 0.000 claims 3
- 229960005261 aspartic acid Drugs 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 210000004027 cell Anatomy 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 229960002989 glutamic acid Drugs 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229910052717 sulfur Chemical group 0.000 claims 3
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 claims 2
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Chemical group OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical group NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Chemical group OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical group OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- IFGCUJZIWBUILZ-UHFFFAOYSA-N sodium 2-[[2-[[hydroxy-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid Chemical compound [Na+].C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(CC(C)C)NP(O)(=O)OC1OC(C)C(O)C(O)C1O IFGCUJZIWBUILZ-UHFFFAOYSA-N 0.000 claims 2
- 239000004475 Arginine Chemical group 0.000 claims 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Chemical group OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 108020004414 DNA Proteins 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Chemical group OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- 208000037396 Intraductal Noninfiltrating Carcinoma Diseases 0.000 claims 1
- 206010073094 Intraductal proliferative breast lesion Diseases 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical group NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical group OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical group C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Chemical group CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 1
- 206010073099 Lobular breast carcinoma in situ Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Chemical group NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Chemical group 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 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
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical group OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Chemical group OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Chemical group CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 1
- 239000004473 Threonine Chemical group 0.000 claims 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Chemical group C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical group CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims 1
- 229940024606 amino acid Drugs 0.000 claims 1
- 235000001014 amino acid Nutrition 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Chemical group OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 235000009697 arginine Nutrition 0.000 claims 1
- 229960001230 asparagine Drugs 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Chemical group OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 201000005389 breast carcinoma in situ Diseases 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Chemical group SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
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- 239000003814 drug Substances 0.000 claims 1
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- 208000028715 ductal breast carcinoma in situ Diseases 0.000 claims 1
- 201000007273 ductal carcinoma in situ Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 201000007280 estrogen-receptor negative breast cancer Diseases 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Chemical group 0.000 claims 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Chemical group OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
- 235000004554 glutamine Nutrition 0.000 claims 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Chemical group OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 206010020718 hyperplasia Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
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- 229960000310 isoleucine Drugs 0.000 claims 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Chemical group CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 1
- 201000011059 lobular neoplasia Diseases 0.000 claims 1
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- 208000020816 lung neoplasm Diseases 0.000 claims 1
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- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 229930182817 methionine Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Chemical group 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
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical group OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 229960005190 phenylalanine Drugs 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Chemical group OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
- 239000004474 valine Chemical group 0.000 claims 1
- YJWKVYOXTBSMBU-UHFFFAOYSA-N 3-(1H-pyrrolo[2,3-h]quinolin-2-yl)pyrrole-2,5-dione Chemical class O=C1NC(=O)C(C=2NC3=C4C=CN=C4C=CC3=CC=2)=C1 YJWKVYOXTBSMBU-UHFFFAOYSA-N 0.000 abstract 2
- SCQZTFRNWYGYQT-UHFFFAOYSA-N O=C1CCC(=O)N1C(N1)=CC=C2C1=C1C=CN=C1C=C2 Chemical class O=C1CCC(=O)N1C(N1)=CC=C2C1=C1C=CN=C1C=C2 SCQZTFRNWYGYQT-UHFFFAOYSA-N 0.000 abstract 2
- -1 pyrroloquinolinyl-pyrrole-2,5-dione compound Chemical class 0.000 abstract 2
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
- C07D471/06—Peri-condensed systems
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- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
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- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4535—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom, e.g. pizotifen
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- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
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- 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
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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- A—HUMAN NECESSITIES
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- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
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Abstract
Pirolokinolinilpirolidin-2,5-dionski spoj formule IVa, IVb, Va ili Vb, ili njegove farmaceutski prihvatljive soli: naznačen time što: R1, R2 i R3 se neovisno bira iz skupine koju čine vodik, F, Cl, Br, I, -NR5R6, -(C1-C6)alkil, -(C1-C6)supstituirani alkil, -(C3-C9)cikloalkil, -(C3-C9)supstituirani cikloalkil, -O-(C1-C6)alkil, -O-(C1-C6)supstituirani alkil, -O-(C3-C9)cikloalkil i -O-(C3-C9)supstituirani cikloalkil, aril, heteroaril, heterociklil; gdje aril je aromatska karbociklička skupina koju čine jedan, dva ili tri aromatska prstena, koji mogu biti kondenzirani s jednim ili više dodatnih nearomatskih karbocikličkih ili heterocikličkih prstena s 4 do 9 članova; gdje heteroaril je heteroaromatska skupina koju čine jedan, dva ili tri prstena, koji sadrže 1-4 heteroatoma, uključujući heteroaromatske skupine koje čine jedan, dva ili tri prstena, koji sadrže 1-4 heteroatoma, kondenzirana s jednim ili više dodatnih nearomatskih prstena s 4 do 9 članova; gdje heterociklil je zasićena ili nezasićena stabilna nearomatska prstenasta struktura, koja može biti kondenzirana, spiro ili premoštena kako bi tvorila dodatni prsten, gdje svaki heterocikl sadrži jedan ili više atoma ugljika i jedan do četiri heteroatoma, koje se bira iz skupine koju čine dušik, kisik i sumpor, uključujući stabilne nearomatske 3-7-eročlane monocikličke heterocikličke prstenaste strukture i 8-11-eročlane bicikličke heterocikličke prstenaste strukture; igdje supstituirani alkil ili supstituirani cikloalkil je alkil ili cikloalkil, supstituiran s jednim ili više supstituenata, koje se neovisno bira iz skupine koju čine fluor, aril, heteroaril i -O-(C1-C6)alkil; R4 se neovisno bira iz skupine koju čine vodik, -(C1-C6)alkil i -CH2R7; R5, R6 se neovisno bira iz skupine koju čine vodik i -(C1-C6)alkil; R7 se neovisno bira iz skupine koju čine -O-P(=O)(OH)2, -O-P(=O)(-OH)(-O-(C1-C6)alkil), -O-P(=O)(-O-(C1-C6)alkil)2, -O-P(=O)(-OH)(-O-(CH2)-fenil), -OP(=O)(-O-(CH2)-fenil)2, karboksilna skupina, aminokiselinska skupina i peptid; Q se bira iz skupine koju čine aril, heteroaril, -O-aril, -S-aril, -O-heteroaril i -S-heteroaril; X se bira iz skupine koju čine -(CH2)-, -(NR8)-, S i O; R8 se neovisno bira iz skupine koju čine vodik, -(C1-C6)alkil, -(C1-C6)supstituirani alkil, -(C3-C9)cikloalkil, -(C3-C9)supstituirani cikloalkil, -O-(C1-C6)alkil, -C(=O)-O-(C1-C6)alkil i -C(=O)-O-(C1-C6)supstituirani alkil; Y se bira iz skupine koju čine -(CH2)- ili veza; gdje navedene arilne, heteroarilne, -O-arilne, -S-arilne, -O-heteroarilne i -S-heteroarilne skupine mogu biti supstituirane s jednim ili više supstituenata, koje se neovisno bira iz skupine koju čine F, Cl, Br, I, -NR5R6, -(C1-C6)alkil, -(C1-C6)supstituirani alkil, -(C3-C9)cikloalkil, -(C3-C9)supstituirani cikloalkil, -O-(C1-C6)alkil, -O-(C1-C6)supstituirani alkil, -O-(C3-C9)cikloalkil, -O-(C3-C9)supstituirani cikloalkil, -aril, -aril-(C1-C6)alkil, -aril-O-(C1-C6)alkil, -O-aril, -O-(C1-C4)alkil-aril, heteroaril, heterociklil, -O-(C1-C4)alkil-hetero
Claims (31)
1. Pirolokinolinilpirolidin-2,5-dionski spoj formule IVa, IVb, Va ili Vb, ili njegove farmaceutski prihvatljive soli:
[image]
naznačen time što:
R1, R2 i R3 se neovisno bira iz skupine koju čine vodik, F, Cl, Br, I, -NR5R6, -(C1-C6)alkil, -(C1-C6)supstituirani alkil, -(C3-C9)cikloalkil, -(C3-C9)supstituirani cikloalkil, -O-(C1-C6)alkil, -O-(C1-C6)supstituirani alkil, -O-(C3-C9)cikloalkil i -O-(C3-C9)supstituirani cikloalkil, aril, heteroaril, heterociklil;
gdje aril je aromatska karbociklička skupina koju čine jedan, dva ili tri aromatska prstena, koji mogu biti kondenzirani s jednim ili više dodatnih nearomatskih karbocikličkih ili heterocikličkih prstena s 4 do 9 članova;
gdje heteroaril je heteroaromatska skupina koju čine jedan, dva ili tri prstena, koji sadrže 1-4 heteroatoma, uključujući heteroaromatske skupine koje čine jedan, dva ili tri prstena, koji sadrže 1-4 heteroatoma, kondenzirana s jednim ili više dodatnih nearomatskih prstena s 4 do 9 članova;
gdje heterociklil je zasićena ili nezasićena stabilna nearomatska prstenasta struktura, koja može biti kondenzirana, spiro ili premoštena kako bi tvorila dodatni prsten, gdje svaki heterocikl sadrži jedan ili više atoma ugljika i jedan do četiri heteroatoma, koje se bira iz skupine koju čine dušik, kisik i sumpor, uključujući stabilne nearomatske 3-7-eročlane monocikličke heterocikličke prstenaste strukture i 8-11-eročlane bicikličke heterocikličke prstenaste strukture; i
gdje supstituirani alkil ili supstituirani cikloalkil je alkil ili cikloalkil, supstituiran s jednim ili više supstituenata, koje se neovisno bira iz skupine koju čine fluor, aril, heteroaril i -O-(C1-C6)alkil;
R4 se neovisno bira iz skupine koju čine vodik, -(C1-C6)alkil i -CH2R7;
R5, R6 se neovisno bira iz skupine koju čine vodik i -(C1-C6)alkil;
R7 se neovisno bira iz skupine koju čine -O-P(=O)(OH)2, -O-P(=O)(-OH)(-O-(C1-C6)alkil), -O-P(=O)(-O-(C1-C6)alkil)2, -O-P(=O)(-OH)(-O-(CH2)-fenil), -OP(=O)(-O-(CH2)-fenil)2, karboksilna skupina, aminokiselinska skupina i peptid;
Q se bira iz skupine koju čine aril, heteroaril, -O-aril, -S-aril, -O-heteroaril i -S-heteroaril;
X se bira iz skupine koju čine -(CH2)-, -(NR8)-, S i O;
R8 se neovisno bira iz skupine koju čine vodik, -(C1-C6)alkil, -(C1-C6)supstituirani alkil, -(C3-C9)cikloalkil, -(C3-C9)supstituirani cikloalkil, -O-(C1-C6)alkil, -C(=O)-O-(C1-C6)alkil i -C(=O)-O-(C1-C6)supstituirani alkil;
Y se bira iz skupine koju čine -(CH2)- ili veza;
gdje navedene arilne, heteroarilne, -O-arilne, -S-arilne, -O-heteroarilne i -S-heteroarilne skupine mogu biti supstituirane s jednim ili više supstituenata, koje se neovisno bira iz skupine koju čine F, Cl, Br, I, -NR5R6, -(C1-C6)alkil, -(C1-C6)supstituirani alkil, -(C3-C9)cikloalkil, -(C3-C9)supstituirani cikloalkil, -O-(C1-C6)alkil, -O-(C1-C6)supstituirani alkil, -O-(C3-C9)cikloalkil, -O-(C3-C9)supstituirani cikloalkil, -aril, -aril-(C1-C6)alkil, -aril-O-(C1-C6)alkil, -O-aril, -O-(C1-C4)alkil-aril, heteroaril, heterociklil, -O-(C1-C4)alkil-heterocikl i -(S(=O)2)-(C1-C6)alkil; i
m je 1 ili 2.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što Q je indolilna skupina ili indolilna skupina supstituirana s jednim ili više supstituenata, koje se neovisno bira iz skupine koju čine: F, Cl, Br, I, -(C1-C6)alkil, -(C1-C6)fluor-supstituirani alkil, -(C3-C9)cikloalkil, -(C3-C9)fluor-supstituirani cikloalkil, -O-(C1-C6)alkil, -O-(C1-C6)fluor-supstituirani alkil, -O-(C3-C9)cikloalkil, -O-(C3-C9)fluor-supstituirani cikloalkil, -aril, -O-aril, -O-(C1-C4)alkil-aril, -O-(C1-C4)alkil-heterocikl i -S(=O)2-(C1-C6)alkil.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R4 je -CH2R7, a R7 je -O-P(=O)(OH)2, -O-P(=O)(-OH)(-O-(C1-C6)alkil), -O-P(=O)(-O-(C1-C6)alkil)2, karboksilna skupina, aminokiselinska skupina ili peptid.
4. Spoj u skladu s patentnim zahtjevom 3, naznačen time što R7 je -O-P(=O)(OH)2, -OP(=O)(-OH)(-O-(C1-C6)alkil) ili -O-P(=O)(-O-(C1-C6)alkil)2.
5. Spoj u skladu s patentnim zahtjevom 3, naznačen time što R7 je karboksilna skupina, aminokiselinska skupina ili peptid.
6. Spoj u skladu s patentnim zahtjevom 5, naznačen time što R7 je alanin, arginin, asparagin, asparaginska kiselina, cistein, glutamin, glutaminska kiselina, glicin, histidin, izoleucin, leucin, lizin, metionin, fenilalanin, prolin, serin, treonin, triptofan, tirozin ili valin.
7. Spoj u skladu s patentnim zahtjevom 6, naznačen time što R7 je l-alanin, l-arginin, l-asparagin, l-asparaginska kiselina, l-cistein, l-glutamin, l-glutaminska kiselina, l-glicin, l-histidin, l-izoleucin, l-leucin, l-lizin, l-metionin, l-fenilalanin, l-prolin, l-serin, l-treonin, l-triptofan, l-tirozin ili l-valin.
8. Spoj u skladu s patentnim zahtjevom 5, naznačen time što R7 je peptid.
9. Spoj u skladu s patentnim zahtjevom 8, naznačen time što navedeni peptid se sastoji od dvije ili više imino- ili aminokiselina, koje se bira iz skupine koju čine: l-alanin, l-arginin, l-asparagin, l-asparaginska kiselina, l-cistein, l-glutamin, l-glutaminska kiselina, l-glicin, l-histidin, l-izoleucin, l-leucin, l-lizin, l-metionin, l-fenilalanin, l-prolin, l-serin, l-treonin, l-triptofan, l-tirozin i l-valin.
10. Spoj u skladu s patentnim zahtjevom 1, naznačen time što X se bira iz skupine koju čine -(NR8)-, S i O.
11. Spoj u skladu s patentnim zahtjevom 1, naznačen time što m je 2.
12. Spoj u skladu s zahtjevom 1, naznačen time što ga se bira iz skupine koju čine (+)-cis-3-(5,6-dihidro-4H-pirolo[3,2,1-ij]kinolin-1-il)-4-(1H-indol-3-il)pirolidin-2,5-dion, (–)-cis-3-(5,6-dihidro-4H-pirolo[3,2,1-ij]kinolin-1-il)-4-(1H-indol-3-il)pirolidin-2,5-dion, (+)-trans-3-(5,6-dihidro-4H-pirolo[3,2,1-ij]kinolin-1-il)-4-(1H-indol-3-il)pirolidin-2,5-dion i (–)-trans-3-(5,6-dihidro-4H-pirolo[3,2,1-ij]kinolin-1-il)-4-(1H-indol-3-il)pirolidin-2,5-dion.
13. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je (–)-trans-3-(5,6-dihidro-4H-pirolo[3,2,1-ij]kinolin-1-il)-4-(1H-indol-3-il)pirolidin-2,5-dion.
14. Farmaceutski pripravak, naznačen time što sadrži spoj formule IVa, IVb, Va, ili Vb u skladu s patentnim zahtjevom 1, ili njegovu farmaceutski prihvatljivu sol, zajedno s jednom ili više farmaceutski prihvatljivih podloga ili pomoćnih tvari.
15. Farmaceutski pripravak u skladu s patentnim zahtjevom 14, naznačen time što spoj je (–)-trans-3-(5,6-dihidro-4H-pirolo[3,2,1-ij]kinolin-1-il)-4-(1H-indol-3-il)pirolidin-2,5-dion.
16. Upotreba terapijski djelotvorne količine spoja formule IVa, IVb, Va ili Vb u skladu s patentnim zahtjevom 1, ili njegove farmaceutski prihvatljive soli, naznačena time što je navedeni spoj namijenjen proizvodnji medikamenta za liječenje poremećaja proliferacije stanica.
17. Upotreba u skladu s patentnim zahtjevom 16, naznačena time što navedeni poremećaj proliferacije stanica je prekancerozno stanje.
18. Upotreba u skladu s patentnim zahtjevom 16, naznačena time što navedeni poremećaj proliferacije stanica je rak.
19. Upotreba u skladu s patentnim zahtjevom 18, naznačena time što navedeni rak je rak pluća, rak debelog crijeva, rak dojke, rak gušterače, rak prostate, kronična mijelogena leukemija, melanom ili rak jajnika.
20. Upotreba u skladu s patentnim zahtjevom 16, naznačena time što navedeni poremećaj proliferacije stanica je poremećaj proliferacije stanica dojke.
21. Upotreba u skladu s patentnim zahtjevom 20, naznačena time što navedeni poremećaj proliferacije stanica dojke je prekancerozno stanje dojke.
22. Upotreba u skladu s patentnim zahtjevom 21, naznačena time što navedeno prekancerozno stanje dojke se bira iz skupine koju čine atipična hiperplazija dojke, duktalni karcinom in situ i lobularni karcinom in situ.
23. Upotreba u skladu s patentnim zahtjevom 20, naznačena time što navedeni poremećaj proliferacije stanica dojke je rak dojke.
24. Upotreba u skladu s patentnim zahtjevom 23, naznačena time što navedeni rak dojke je rak dojke negativan na estrogenski receptor.
25. Upotreba u skladu s patentnim zahtjevom 18, naznačena time što navedeno liječenje raka se sastoji u smanjivanju veličine tumora.
26. Upotreba u skladu s patentnim zahtjevom 18, naznačena time što rak je metastazirajući rak.
27. Upotreba u skladu s patentnim zahtjevom 26, naznačena time što navedeno liječenje raka se sastoji u inhibiranju invazije stanica metastazirajućeg raka.
28. Upotreba u skladu s bilo kojim od patentnih zahtjeva 16-27, 30 ili 31, naznačena time što spoj se bira iz skupine koju čine (+)-cis-3-(5,6-dihidro-4H-pirolo[3,2,1-ij]kinolin-1-il)-4-(1H-indol-3-il)pirolidin-2,5-dion, (–)-cis-3-(5,6-dihidro-4H-pirolo[3,2,1-ij]kinolin-1-il)-4-(1H-indol-3-il)pirolidin-2,5-dion, (+)-trans-3-(5,6-dihidro-4H-pirolo[3,2,1-ij]kinolin-1-il)-4-(1H-indol-3-il)pirolidin-2,5-dion i (–)-trans-3-(5,6-dihidro-4H-pirolo[3,2,1-ij]kinolin-1-il)-4-(1H-indol-3-il)pirolidin-2,5-dion.
29. Upotreba u skladu s bilo kojim od patentnih zahtjeva 16-27, 30 ili 31, naznačena time što spoj je (–)-trans-3-(5,6-dihidro-4H-pirolo[3,2,1-ij]kinolin-1-il)-4-(1H-indol-3-il)pirolidin-2,5-dion.
30. Upotreba u skladu s patentnim zahtjevom 16, naznačena time što stanice s proliferativnim poremećajem sadrže DNA koja kodira c-Met.
31. Upotreba u skladu s patentnim zahtjevom 30, naznačena time što stanice imaju konstitutivno pojačanu aktivnost c-Met.
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US65095105P | 2005-02-09 | 2005-02-09 | |
PCT/US2006/004456 WO2006086484A1 (en) | 2005-02-09 | 2006-02-09 | Meleimide derivatives, pharmaceutical compositions and methods for treatment of cancer |
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EP (2) | EP1846406B9 (hr) |
JP (1) | JP4171061B2 (hr) |
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