HRP20192159T1 - Spojevi za liječenje mišićne atrofije kralježnice - Google Patents
Spojevi za liječenje mišićne atrofije kralježnice Download PDFInfo
- Publication number
- HRP20192159T1 HRP20192159T1 HRP20192159TT HRP20192159T HRP20192159T1 HR P20192159 T1 HRP20192159 T1 HR P20192159T1 HR P20192159T T HRP20192159T T HR P20192159TT HR P20192159 T HRP20192159 T HR P20192159T HR P20192159 T1 HRP20192159 T1 HR P20192159T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyrido
- pyridazin
- pyrimidin
- methylimidazo
- dimethylimidazo
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 39
- 208000002320 spinal muscular atrophy Diseases 0.000 title claims 3
- 239000001257 hydrogen Substances 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 22
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- CRUGWTAPLOCETH-UHFFFAOYSA-N 7-(4,7-diazaspiro[2.5]octan-7-yl)-2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=C(C)C2=N1)C1=CC(=O)N2C=C(C=C(C)C2=N1)N1CCNC2(CC2)C1 CRUGWTAPLOCETH-UHFFFAOYSA-N 0.000 claims 3
- ISVCSHDSFOZLBX-UHFFFAOYSA-N 7-(4,7-diazaspiro[2.5]octan-7-yl)-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=CC2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CCNC2(CC2)C1 ISVCSHDSFOZLBX-UHFFFAOYSA-N 0.000 claims 3
- VICDQEAUPWFDTI-GASCZTMLSA-N 7-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-9-methyl-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C[C@H]1CN(C[C@@H](C)N1)C1=CN2C(=O)C=C(N=C2C(C)=C1)C1=NN2C=C(C)N=C2C=C1 VICDQEAUPWFDTI-GASCZTMLSA-N 0.000 claims 3
- YXFPYQSJPBUTNI-MRXNPFEDSA-N 7-[(8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=CC2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CCN2CCC[C@@H]2C1 YXFPYQSJPBUTNI-MRXNPFEDSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- -1 1,4-diazepan-1-yl Chemical group 0.000 claims 2
- JWXBTBSDAVJRMG-GASCZTMLSA-N 2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)-7-[(3S,5R)-3,5-dimethylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C[C@H]1CN(C[C@@H](C)N1)C1=CN2C(=O)C=C(N=C2C=C1)C1=NN2C=C(C)N=C2C(C)=C1 JWXBTBSDAVJRMG-GASCZTMLSA-N 0.000 claims 2
- COFWKURLHFRZLI-HNNXBMFYSA-N 2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)-9-methyl-7-[(3S)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C[C@H]1CN(CCN1)C1=CN2C(=O)C=C(N=C2C(C)=C1)C1=NN2C=C(C)N=C2C(C)=C1 COFWKURLHFRZLI-HNNXBMFYSA-N 0.000 claims 2
- HUSSYBASIXAKFV-UHFFFAOYSA-N 7-(4,7-diazaspiro[2.5]octan-7-yl)-9-methyl-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=CC2=N1)C1=CC(=O)N2C=C(C=C(C)C2=N1)N1CCNC2(CC2)C1 HUSSYBASIXAKFV-UHFFFAOYSA-N 0.000 claims 2
- YLRYYUXFWWMZDV-QGZVFWFLSA-N 7-[(8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=C(C)C2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CCN2CCC[C@@H]2C1 YLRYYUXFWWMZDV-QGZVFWFLSA-N 0.000 claims 2
- YLRYYUXFWWMZDV-KRWDZBQOSA-N 7-[(8aS)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=C(C)C2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CCN2CCC[C@H]2C1 YLRYYUXFWWMZDV-KRWDZBQOSA-N 0.000 claims 2
- YXFPYQSJPBUTNI-INIZCTEOSA-N 7-[(8aS)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=CC2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CCN2CCC[C@H]2C1 YXFPYQSJPBUTNI-INIZCTEOSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- PXBGTHPHKPNGDM-UHFFFAOYSA-N 2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)-7-(3,3-dimethylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC=1N=C2N(N=C(C=C2C)C=2N=C3N(C(C2)=O)C=C(C=C3)N3CC(NCC3)(C)C)C1 PXBGTHPHKPNGDM-UHFFFAOYSA-N 0.000 claims 1
- ACFOLYZMDFMLCJ-CQSZACIVSA-N 2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)-7-[(3R)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CC=1N=C2N(N=C(C=C2C)C=2N=C3N(C(C2)=O)C=C(C=C3)N3C[C@H](NCC3)C)C1 ACFOLYZMDFMLCJ-CQSZACIVSA-N 0.000 claims 1
- AAYCYOAGHHTAMV-LJQANCHMSA-N 2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)-7-[(3R)-3-pyrrolidin-1-ylpyrrolidin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=C(C)C2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CC[C@H](C1)N1CCCC1 AAYCYOAGHHTAMV-LJQANCHMSA-N 0.000 claims 1
- ACFOLYZMDFMLCJ-AWEZNQCLSA-N 2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)-7-[(3S)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CC=1N=C2N(N=C(C=C2C)C=2N=C3N(C(C2)=O)C=C(C=C3)N3C[C@@H](NCC3)C)C1 ACFOLYZMDFMLCJ-AWEZNQCLSA-N 0.000 claims 1
- AAYCYOAGHHTAMV-IBGZPJMESA-N 2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)-7-[(3S)-3-pyrrolidin-1-ylpyrrolidin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=C(C)C2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CC[C@@H](C1)N1CCCC1 AAYCYOAGHHTAMV-IBGZPJMESA-N 0.000 claims 1
- ZMUUKOBZCNOVEG-IYBDPMFKSA-N 2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)-7-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C[C@H]1CN(C[C@@H](C)N1)C1=CN2C(=O)C=C(N=C2C(C)=C1)C1=NN2C=C(C)N=C2C(C)=C1 ZMUUKOBZCNOVEG-IYBDPMFKSA-N 0.000 claims 1
- JWXBTBSDAVJRMG-GJZGRUSLSA-N 2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)-7-[(3S,5S)-3,5-dimethylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C[C@H]1CN(C[C@H](C)N1)C1=CN2C(=O)C=C(N=C2C=C1)C1=NN2C=C(C)N=C2C(C)=C1 JWXBTBSDAVJRMG-GJZGRUSLSA-N 0.000 claims 1
- COFWKURLHFRZLI-OAHLLOKOSA-N 2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)-9-methyl-7-[(3R)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C[C@@H]1CN(CCN1)C1=CN2C(=O)C=C(N=C2C(C)=C1)C1=NN2C=C(C)N=C2C(C)=C1 COFWKURLHFRZLI-OAHLLOKOSA-N 0.000 claims 1
- FQBWKZIEKHEPQP-UHFFFAOYSA-N 2-(2-methylimidazo[1,2-b]pyridazin-6-yl)-7-(4-methylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC=1N=C2N(N=C(C=C2)C=2N=C3N(C(C2)=O)C=C(C=C3)N3CCN(CC3)C)C1 FQBWKZIEKHEPQP-UHFFFAOYSA-N 0.000 claims 1
- VTERHMMTDUNXPW-CYBMUJFWSA-N 2-(2-methylimidazo[1,2-b]pyridazin-6-yl)-7-[(3R)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CC=1N=C2N(N=C(C=C2)C=2N=C3N(C(C2)=O)C=C(C=C3)N3C[C@H](NCC3)C)C1 VTERHMMTDUNXPW-CYBMUJFWSA-N 0.000 claims 1
- VTERHMMTDUNXPW-ZDUSSCGKSA-N 2-(2-methylimidazo[1,2-b]pyridazin-6-yl)-7-[(3S)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C[C@H]1CN(CCN1)C1=CN2C(=O)C=C(N=C2C=C1)C1=NN2C=C(C)N=C2C=C1 VTERHMMTDUNXPW-ZDUSSCGKSA-N 0.000 claims 1
- WHHDRZLWEHRKJJ-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound N1(CCNCCC1)C=1C=CC=2N(C(C=C(N2)C=2C=C(C=3N(N2)C=C(N3)C)C)=O)C1 WHHDRZLWEHRKJJ-UHFFFAOYSA-N 0.000 claims 1
- CQARAHLOHRWONI-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound N1(CCNCCC1)C=1C=CC=2N(C(C=C(N2)C=2C=CC=3N(N2)C=C(N3)C)=O)C1 CQARAHLOHRWONI-UHFFFAOYSA-N 0.000 claims 1
- HBQHPLRMAGZCML-UHFFFAOYSA-N 7-(3,3-dimethylpiperazin-1-yl)-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1(CN(CCN1)C=1C=CC=2N(C(C=C(N2)C=2C=CC=3N(N2)C=C(N3)C)=O)C1)C HBQHPLRMAGZCML-UHFFFAOYSA-N 0.000 claims 1
- WBCIARXADDFNIO-UHFFFAOYSA-N 7-(3,3-dimethylpiperazin-1-yl)-9-methyl-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1(CN(CCN1)C=1C=C(C=2N(C(C=C(N2)C=2C=CC=3N(N2)C=C(N3)C)=O)C1)C)C WBCIARXADDFNIO-UHFFFAOYSA-N 0.000 claims 1
- ASKZRYGFUPSJPN-UHFFFAOYSA-N 7-(4,7-diazaspiro[2.5]octan-7-yl)-2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=C(C)C2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CCNC2(CC2)C1 ASKZRYGFUPSJPN-UHFFFAOYSA-N 0.000 claims 1
- JGUXKQRSKUERHW-OAHLLOKOSA-N 7-[(3R)-3-ethylpiperazin-1-yl]-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC[C@@H]1CN(CCN1)C1=CN2C(=O)C=C(N=C2C=C1)C1=NN2C=C(C)N=C2C=C1 JGUXKQRSKUERHW-OAHLLOKOSA-N 0.000 claims 1
- VICDQEAUPWFDTI-GJZGRUSLSA-N 7-[(3S,5S)-3,5-dimethylpiperazin-1-yl]-9-methyl-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C[C@H]1CN(C[C@H](C)N1)C1=CN2C(=O)C=C(N=C2C(C)=C1)C1=NN2C=C(C)N=C2C=C1 VICDQEAUPWFDTI-GJZGRUSLSA-N 0.000 claims 1
- ABLKZJZMCINJBX-XMMPIXPASA-N 7-[(8aR)-8a-methyl-1,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=C(C)C2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CCN2CCC[C@]2(C)C1 ABLKZJZMCINJBX-XMMPIXPASA-N 0.000 claims 1
- AJFUUCOVZGEGNK-HSZRJFAPSA-N 7-[(8aR)-8a-methyl-1,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=CC2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CCN2CCC[C@]2(C)C1 AJFUUCOVZGEGNK-HSZRJFAPSA-N 0.000 claims 1
- ABLKZJZMCINJBX-DEOSSOPVSA-N 7-[(8aS)-8a-methyl-1,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-2-(2,8-dimethylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=C(C)C2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CCN2CCC[C@@]2(C)C1 ABLKZJZMCINJBX-DEOSSOPVSA-N 0.000 claims 1
- AJFUUCOVZGEGNK-QHCPKHFHSA-N 7-[(8aS)-8a-methyl-1,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-2-(2-methylimidazo[1,2-b]pyridazin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CN2N=C(C=CC2=N1)C1=CC(=O)N2C=C(C=CC2=N1)N1CCN2CCC[C@@]2(C)C1 AJFUUCOVZGEGNK-QHCPKHFHSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (32)
1. Spoj, naznačen time, da je predstavljen formulom (I)
u kojoj je
R1 vodik ili C1−7−alkil;
R2 vodik, cijano, C1−7−alkil, C1−7−haloalkil ili C3−8−cikloalkil;
R3 vodik, C1−7−alkil ili C3−8−cikloalkil;
A N-heterocikloalkil ili NR12R13, pri čemu N-heterocikloalkil sadrži 1 ili 2 dušikova atoma u prstenu i po izboru je supstituiran s 1, 2, 3 ili 4 supstituenta izabrana od R14;
R12 heterocikloalkil koji sadrži 1 dušikov atom u prstenu, pri čemu je heterocikloalkil po izboru supstituiran s 1, 2, 3 ili 4 supstituenta izabrana od R14;
R13 vodik, C1−7−alkil ili C3−8−cikloalkil;
R14 nezavisno izabran od vodika, C1−7−alkila, amino, amino-C1−7−alkila, C3−8−cikloalkila i heterocikloalkila ili dva R14 zajedno formiraju C1−7−alkilen;
pod uvjetom da ako A predstavlja N-heterocikloalkil koji sadrži samo 1 atom dušika u prstenu, tada je najmanje jedan supstituent R14 amino ili amino-C1−7−alkil;
i njihove farmaceutski prihvatljive soli.
2. Spoj prema patentnom zahtjevu 1, naznačen time, da je
R1 vodik ili C1−7−alkil;
R2 vodik, cijano, C1−7−alkil, C1−7−haloalkil ili C3−8−cikloalkil;
R3 vodik, C1−7−alkil ili C3−8−cikloalkil;
A heterocikloalkil koji sadrži 1 ili 2 dušikova atoma u prstenu, pri čemu je N-heterocikloalkil po izboru supstituiran s 1, 2, 3 ili 4 supstituenta izabrana od R14;
R14 nezavisno izabran od vodika, C1−7−alkila, amino, amino-C1−7−alkila, C3−8−cikloalkila i heterocikloalkila ili dva R14 zajedno formiraju C1−7−alkilen;
pod uvjetom da ako A predstavlja N-heterocikloalkil koji sadrži samo 1 atom dušika u prstenu, tada je najmanje jedan supstituent R14 amino ili amino-C1−7−alkil;
i njihove farmaceutski prihvatljive soli.
3. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time, da je R1 C1−7−alkil.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da je R1 metil.
5. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time, da je R2 vodik ili C1−7−alkil.
6. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da je R2 vodik ili metil.
7. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time, da je R3 vodik ili metil.
8. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time, da je R14 nezavisno izabran od C1−7−alkila i heterocikloalkila ili time, da dva R14 zajedno formiraju C1−7−alkilen.
9. Spoj prema bilo kojem od patentnih zahtjeva 1 do 6, naznačen time, da je R14 nezavisno izabran od metila, etila i pirolidinila ili time, da dva R14 zajedno formiraju etilen.
10. Spoj prema bilo kojem od patentnih zahtjeva 1 do 9, naznačen time, da je A
,
pri čemu je
X N ili CH;
R4 vodik, C1−7−alkil ili −(CH2)m-NR9R10;
R5 vodik ili C1−7−alkil;
R6 vodik ili C1−7−alkil;
R7 vodik ili C1−7−alkil;
R8 vodik ili C1−7−alkil;
R9 i R10 su nezavisno izabrani od vodika, C1−7−alkila i C3−8−cikloalkila;
n 0, 1 ili 2;
m 0, 1, 2 ili 3;
ili R4 i R5 zajedno formiraju C1−7−alkilen;
ili R4 i R7 zajedno formiraju C1−7−alkilen;
ili R5 i R6 zajedno formiraju C2−7−alkilen;
ili R5 i R7 zajedno formiraju C1−7−alkilen;
ili R5 i R9 zajedno formiraju C1−7−alkilen;
ili R7 i R8 zajedno formiraju C2−7−alkilen;
ili R7 i R9 zajedno formiraju C1−7−alkilen;
ili R9 i R10 zajedno formiraju C2−7−alkilen;
pod uvjetom da ako X je CH, onda R4 je −(CH2)m-NR9R10; i
pod uvjetom da ako X je N, a R4 je −(CH2)m-NR9R10, onda m je 2 ili 3.
11. Spoj prema patentnom zahtjevu 10, naznačen time, da X je N.
12. Spoj prema bilo kojem od patentnih zahtjeva 10 do 11, naznačen time, da n je 1.
13. Spoj prema bilo kojem od patentnih zahtjeva 10 do 12, naznačen time, da je R4 vodik.
14. Spoj prema bilo kojem od patentnih zahtjeva 10 do 13, naznačen time, da je R7 vodik ili metil.
15. Spoj prema bilo kojem od patentnih zahtjeva 10 do 14, naznačen time, da je R8 vodik.
16. Spoj prema bilo kojem od patentnih zahtjeva 10 do 15, naznačen time, da R5 i R6 zajedno formiraju etilen.
17. Spoj prema bilo kojem od patentnih zahtjeva 10 do 16, naznačen time, da R9 i R10 zajedno formiraju butilen.
18. Spoj prema bilo kojem od patentnih zahtjeva 1 do 17, naznačen time, da je A odabran iz skupine koju čine:
pri čemu su R4, R5, R6, R7 i R8 kao što je definirano u bilo kojem od patentnih zahtjeva od 1 do 17 i time, da je R11 vodik ili C1−7−alkil.
19. Spoj prema bilo kojem od patentnih zahtjeva 1 do 18, naznačen time, da je A odabran iz skupine koju čine piperazin-1-il, 1,4-diazepan-1-il, pirolidin-1-il i heksahidropirolo[1,2−a]pirazin-2(1H)-il, od kojih je svaki po izboru supstituiran s 1 ili 2 supstituenta izabrana od R14 kako je definirano prema bilo kojem od patentnih zahtjeva 1 do 33.
20. Spoj prema bilo kojem od patentnih zahtjeva 1 do 19, naznačen time, da je A odabran iz skupine koju čine:
21. Spoj prema bilo kojem od patentnih zahtjeva 1 do 20, naznačen time, da je A odabran iz skupine koju čine:
22. Spoj prema bilo kojem od patentnih zahtjeva 1 do 21, naznačen time, da je odabran iz skupine koju čine:
2-(2-metilimidazo[1,2−b]piridazin-6-il)-7-(4-metilpiperazin-1-il)pirido[1,2−a]pirimidin-4-on;
7-[(8aR)-3,4,6,7,8,8a-heksahidro-1H-pirolo[1,2−a]pirazin-2-il]-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(8aS)-3,4,6,7,8,8a-heksahidro-1H-pirolo[1,2−a]pirazin-2-il]-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(8aR)-3,4,6,7,8,8a-heksahidro-1H-pirolo[1,2−a]pirazin-2-il]-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(8aS)-8a-metil-1,3,4,6,7,8-heksahidropirolo[1,2−a]pirazin-2-il]-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(8aR)-8a-metil-1,3,4,6,7,8-heksahidropirolo[1,2−a]pirazin-2-il]-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-7-[(3S,5R)-3,5-dimetilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-7-[(3S)-3-metilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-7-[(3R)-3-metilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
7-(1,4-diazepan-1-il)-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
2-(2-metilimidazo[1,2−b]piridazin-6-il)-7-[(3S)-3-metilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
2-(2-metilimidazo[1,2−b]piridazin-6-il)-7-[(3R)-3-metilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
7-(1,4-diazepan-1-il)-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(3R,5S)-3,5-dimetilpiperazin-1-il]-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(8aS)-3,4,6,7,8,8a-heksahidro-1H-pirolo[1,2−a]pirazin-2-il]-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(8aS)-8a-metil-1,3,4,6,7,8-heksahidropirolo[1,2−a]pirazin-2-il]-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(8aR)-8a-metil-1,3,4,6,7,8-heksahidropirolo[1,2−a]pirazin-2-il]-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-7-[(3R)-3-pirolidin-1-ilpirolidin-1-il]pirido[1,2−a]pirimidin-4-on;
7-(4,7-diazaspiro[2.5]oktan-7-il)-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-(4,7-diazaspiro[2.5]oktan-7-il)-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
2-(2-metilimidazo[1,2−b]piridazin-6-il)-7-[(3R)-3-pirolidin-1-ilpirolidin-1-il]pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-7-(3,3-dimetilpiperazin-1-il)pirido[1,2−a]pirimidin-4-on;
7-(3,3-dimetilpiperazin-1-il)-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-9-metil-7-[(3S)-3-metilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-9-metil-7-[(3R)-3-metilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-7-[(3R,5S)-3,5-dimetilpiperazin-1-il]-9-metil-pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-7-(3,3-dimetilpiperazin-1-il)-9-metil-pirido[1,2−a]pirimidin-4-on;
7-(4,7-diazaspiro[2.5]oktan-7-il)-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-9-metil-pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-7-[(3S,5S)-3,5-dimetilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-7-[(3S)-3-pirolidin-1-ilpirolidin-1-il]pirido[1,2−a]pirimidin-4-on;
2-(2-metilimidazo[1,2−b]piridazin-6-il)-7-[(3S)-3-pirolidin-1-ilpirolidin-1-il]pirido[1,2−a]pirimidin-4-on;
7-[(3S,5S)-3,5-dimetilpiperazin-1-il]-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
9-metil-2-(2-metilimidazo[1,2−b]piridazin-6-il)-7-[(3S)-3-metilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
9-metil-2-(2-metilimidazo[1,2−b]piridazin-6-il)-7-[(3R)-3-metilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
7-[(3R,5S)-3,5-dimetilpiperazin-1-il]-9-metil-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-(3,3-dimetilpiperazin-1-il)-9-metil-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-(4,7-diazaspiro[2.5]oktan-7-il)-9-metil-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(3S,5S)-3,5-dimetilpiperazin-1-il]-9-metil-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(3R)-3-etilpiperazin-1-il]-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
i njihove farmaceutski prihvatljive soli.
23. Spoj prema bilo kojem od patentnih zahtjeva 1 do 22, naznačen time, da je odabran iz skupine koju čine:
7-[(8aR)-3,4,6,7,8,8a-heksahidro-1H-pirolo[1,2−a]pirazin-2-il]-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(8aS)-3,4,6,7,8,8a-heksahidro-1H-pirolo[1,2−a]pirazin-2-il]-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(8aR)-3,4,6,7,8,8a-heksahidro-1H-pirolo[1,2−a]pirazin-2-il]-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-7-[(3S,5R)-3,5-dimetilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
7-[(3R,5S)-3,5-dimetilpiperazin-1-il]-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-[(8aS)-3,4,6,7,8,8a-heksahidro-1H-pirolo[1,2−a]pirazin-2-il]-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-(4,7-diazaspiro[2.5]oktan-7-il)-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-(4,7-diazaspiro[2.5]oktan-7-il)-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-9-metil-7-[(3S)-3-metilpiperazin-1-il]pirido[1,2−a]pirimidin-4-on;
7-(4,7-diazaspiro[2.5]oktan-7-il)-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-9-metil-pirido[1,2−a]pirimidin-4-on;
7-[(3R,5S)-3,5-dimetilpiperazin-1-il]-9-metil-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
7-(4,7-diazaspiro[2.5]oktan-7-il)-9-metil-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on;
i njihove farmaceutski prihvatljive soli.
24. Spoj prema patentnom zahtjevu 22 ili 23, naznačen time, da je spoj 7-[(8aR)-3,4,6,7,8,8a-heksahidro-1H-pirolo[1,2−a]pirazin-2-il]-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on ili njegova farmaceutski prihvatljiva sol.
25. Spoj prema patentnom zahtjevu 22 ili 23, naznačen time, da je spoj 7-(4,7-diazaspiro[2.5]oktan-7-il)-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on ili njegova farmaceutski prihvatljiva sol.
26. Spoj prema patentnom zahtjevu 22 ili 23, naznačen time, da je spoj 7-(4,7-diazaspiro[2.5]oktan-7-il)-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on ili njegova farmaceutski prihvatljiva sol.
27. Spoj prema patentnom zahtjevu 22 ili 23, naznačen time, da je spoj 7-(4,7-diazaspiro[2.5]oktan-7-il)-2-(2,8-dimetilimidazo[1,2−b]piridazin-6-il)-9-metil-pirido[1,2−a]pirimidin-4-on ili njegova farmaceutski prihvatljiva sol.
28. Spoj prema patentnom zahtjevu 22 ili 23, naznačen time, da je spoj 7-[(3R,5S)-3,5-dimetilpiperazin-1-il]-9-metil-2-(2-metilimidazo[1,2−b]piridazin-6-il)pirido[1,2−a]pirimidin-4-on ili njegova farmaceutski prihvatljiva sol.
29. Spoj prema patentnom zahtjevu 22 ili 23, naznačen time, da je spoj
.
30. Farmaceutski pripravci, naznačeni time, da sadrže spojeve formule (I) prema bilo kojem od patentnih zahtjeva 1 do 29 ili njihove farmaceutski prihvatljive soli i jednu ili više farmaceutski prihvatljivih pomoćnih tvari.
31. Prethodno navedeni spojevi formule (I) prema bilo kojem od patentnih zahtjeva 1 do 29 ili njihove farmaceutski prihvatljive soli, naznačeni time, da se upotrebljavaju kao terapeutski aktivne tvari.
32. Spojevi formule (I) prema bilo kojem od patentnih zahtjeva 1 do 29 ili njihove farmaceutski prihvatljive soli, naznačeni time, da se upotrebljavaju u liječenju ili sprečavanju mišićne atrofije kralježnice (SMA – engl. spinal muscular atrophy).
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201461993839P | 2014-05-15 | 2014-05-15 | |
EP15721701.9A EP3143025B1 (en) | 2014-05-15 | 2015-05-11 | Compounds for treating spinal muscular atrophy |
PCT/EP2015/060343 WO2015173181A1 (en) | 2014-05-15 | 2015-05-11 | Compounds for treating spinal muscular atrophy |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20192159T1 true HRP20192159T1 (hr) | 2020-02-21 |
Family
ID=53175048
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20230637TT HRP20230637T1 (hr) | 2014-05-15 | 2015-05-11 | Postupak za proizvodnju spojeva korisnih za liječenje spinalne mišićne atrofije |
HRP20192159TT HRP20192159T1 (hr) | 2014-05-15 | 2019-11-29 | Spojevi za liječenje mišićne atrofije kralježnice |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20230637TT HRP20230637T1 (hr) | 2014-05-15 | 2015-05-11 | Postupak za proizvodnju spojeva korisnih za liječenje spinalne mišićne atrofije |
Country Status (36)
Country | Link |
---|---|
US (1) | US9969754B2 (hr) |
EP (3) | EP3143025B1 (hr) |
JP (1) | JP6236173B2 (hr) |
KR (2) | KR102256013B1 (hr) |
CN (1) | CN106459092B (hr) |
AR (1) | AR100442A1 (hr) |
AU (1) | AU2015261046C1 (hr) |
BR (1) | BR112016026205B1 (hr) |
CA (1) | CA2948561C (hr) |
CL (1) | CL2016002836A1 (hr) |
CR (1) | CR20160518A (hr) |
DK (1) | DK3143025T3 (hr) |
EA (2) | EA035068B1 (hr) |
ES (2) | ES2949660T3 (hr) |
FR (1) | FR21C1039I2 (hr) |
HR (2) | HRP20230637T1 (hr) |
HU (2) | HUE046491T2 (hr) |
IL (2) | IL248653B (hr) |
LT (1) | LTPA2021010I1 (hr) |
MA (2) | MA51988A (hr) |
MX (1) | MX371050B (hr) |
MY (1) | MY174284A (hr) |
NL (1) | NL301128I2 (hr) |
NO (1) | NO2021035I1 (hr) |
NZ (1) | NZ725008A (hr) |
PE (1) | PE20170128A1 (hr) |
PH (1) | PH12016502081A1 (hr) |
PL (2) | PL3663296T3 (hr) |
PT (1) | PT3143025T (hr) |
RS (1) | RS59718B1 (hr) |
SG (1) | SG11201609497TA (hr) |
SI (2) | SI3143025T1 (hr) |
TW (1) | TWI667239B (hr) |
UA (1) | UA119670C2 (hr) |
WO (1) | WO2015173181A1 (hr) |
ZA (1) | ZA201607026B (hr) |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EA037123B1 (ru) | 2012-02-10 | 2021-02-09 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Соединения для лечения спинальной мышечной атрофии |
KR20160045063A (ko) | 2013-08-19 | 2016-04-26 | 에프. 호프만-라 로슈 아게 | 스크리닝 방법 |
US10882868B2 (en) * | 2014-05-15 | 2021-01-05 | Hoffmann-La Roche Inc. | Compounds for treating spinal muscular atrophy |
EP3298017B1 (en) | 2015-05-20 | 2019-08-14 | H. Hoffnabb-La Roche Ag | Compounds for treating spinal muscular atrophy |
EP3310169B1 (en) | 2015-05-30 | 2023-05-17 | PTC Therapeutics, Inc. | Methods for modulating rna splicing |
CA2996657A1 (en) * | 2015-11-12 | 2017-05-18 | Kathleen Dorothy MCCARTHY | Compounds for treating amyotrophic lateral sclerosis |
WO2017080967A1 (en) | 2015-11-12 | 2017-05-18 | F. Hoffmann-La Roche Ag | Compositions for treating spinal muscular atrophy |
WO2017100726A1 (en) | 2015-12-10 | 2017-06-15 | Ptc Therapeutics, Inc. | Methods for treatng huntington's disease |
WO2017097728A1 (en) | 2015-12-10 | 2017-06-15 | F. Hoffmann-La Roche Ag | Bridged piperidine derivatives |
EP3544435A4 (en) | 2016-11-28 | 2020-11-04 | PTC Therapeutics, Inc. | RNA SPLICE MODULATION PROCESSES |
US11407753B2 (en) | 2017-06-05 | 2022-08-09 | Ptc Therapeutics, Inc. | Compounds for treating Huntington's disease |
KR20200017476A (ko) | 2017-06-14 | 2020-02-18 | 피티씨 테라퓨틱스, 인크. | Rna 스플라이싱의 변경 방법 |
EP3644996B1 (en) | 2017-06-28 | 2023-07-26 | PTC Therapeutics, Inc. | Methods for treating huntington's disease |
US11395822B2 (en) | 2017-06-28 | 2022-07-26 | Ptc Therapeutics, Inc. | Methods for treating Huntington's disease |
JP7075484B2 (ja) * | 2017-09-22 | 2022-05-25 | エフ.ホフマン-ラ ロシュ アーゲー | 7-(4,7-ジアザスピロ[2.5]オクタン-7-イル)-2-(2,8-ジメチルイミダゾ[1,2-b]ピリダジン-6-イル)ピリド[1,2-a]ピリミジン-4-オン誘導体の製造方法 |
CA3078137A1 (en) | 2017-10-03 | 2019-04-11 | F. Hoffmann-La Roche Ag | New treatment of sma |
WO2019191092A1 (en) | 2018-03-27 | 2019-10-03 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
LT3814357T (lt) | 2018-06-27 | 2024-06-25 | Ptc Therapeutics, Inc. | Heterocikliniai ir heteroarilų junginiai, skirti hantingtono ligos gydymui |
BR112020026637A2 (pt) | 2018-06-27 | 2021-03-30 | Reborna Biosciences, Inc. | Agente profilático ou terapêutico para atrofia muscular espinhal |
EP3814360B1 (en) | 2018-06-27 | 2024-10-02 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
CA3116458C (en) | 2018-10-19 | 2023-12-12 | F. Hoffmann-La Roche Ag | New forms of pyrido[1,2-a]pyrimidin-4-one derivatives, its formulation and its process of making |
WO2020249577A1 (en) | 2019-06-12 | 2020-12-17 | F. Hoffmann-La Roche Ag | New treatment of sma |
US20220315607A1 (en) | 2019-07-31 | 2022-10-06 | Teva Pharmaceuticals International Gmbh | Solid state forms of risdiplam and process for preparation thereof |
WO2022048675A1 (zh) * | 2020-09-07 | 2022-03-10 | 苏州科睿思制药有限公司 | Risdiplam晶型及其制备方法和用途 |
WO2022162107A1 (en) | 2021-02-01 | 2022-08-04 | Sandoz Ag | Crystalline form of risdiplam |
JP2024510487A (ja) * | 2021-03-17 | 2024-03-07 | エフ. ホフマン-ラ ロシュ アーゲー | 新規なチアジアゾロピリミドン誘導体 |
IL305203A (en) | 2021-03-17 | 2023-10-01 | Hoffmann La Roche | New histories of thiazolopyrimidines |
KR20230145461A (ko) | 2021-03-18 | 2023-10-17 | 에프. 호프만-라 로슈 아게 | 리스디플람의 제조 방법 |
CN118055767A (zh) | 2021-10-06 | 2024-05-17 | 豪夫迈·罗氏有限公司 | 新颖的组合施用 |
CN118005654A (zh) * | 2022-04-18 | 2024-05-10 | 深圳市塔吉瑞生物医药有限公司 | 取代的吡啶并嘧啶酮类化合物及包含该化合物的组合物及其用途 |
WO2023240236A1 (en) | 2022-06-10 | 2023-12-14 | Voyager Therapeutics, Inc. | Compositions and methods for the treatment of spinal muscular atrophy related disorders |
WO2024069646A1 (en) * | 2022-09-26 | 2024-04-04 | Natco Pharma Limited | Improved process for the preparation of risdiplam and its intermediates |
TW202423419A (zh) | 2022-10-14 | 2024-06-16 | 美商建南德克公司 | 治療脊髓性肌肉萎縮症之方法 |
WO2024154148A1 (en) * | 2023-01-21 | 2024-07-25 | Harman Finochem Limited | Process for preparation of risdiplam, novel intermediates, and process for preparation thereof |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ292806B6 (cs) * | 1996-08-06 | 2003-12-17 | Pfizer Inc. | Pyrido- nebo pyrimido-6,6- nebo -6,7-bicyklické deriváty, farmaceutické kompozice na jejich bázi |
WO2009042907A1 (en) | 2007-09-27 | 2009-04-02 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Isoindoline compounds for the treatment of spinal muscular atrophy and other uses |
WO2009151546A2 (en) * | 2008-05-27 | 2009-12-17 | Ptc Therapeutics, Inc. | Methods for treating spinal muscular atrophy |
KR20100012134A (ko) * | 2008-07-28 | 2010-02-08 | 신호열 | 마우스 |
US8932818B2 (en) | 2008-08-13 | 2015-01-13 | Ptc Therapeutics, Inc. | Screening assays for compounds that modulate programmed ribosomal frameshifting |
EP2337609B1 (en) * | 2008-08-14 | 2016-08-17 | Cardiac Pacemakers, Inc. | Performance assessment and adaptation of an acoustic communication link |
USRE47689E1 (en) * | 2011-12-30 | 2019-11-05 | Ptc Therapeutics, Inc. | Compounds for treating spinal muscular atrophy |
EA037123B1 (ru) | 2012-02-10 | 2021-02-09 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Соединения для лечения спинальной мышечной атрофии |
CA2878895A1 (en) | 2012-07-13 | 2014-01-16 | Indiana University Research & Technology Corporation | Compounds for treatment of spinal muscular atrophy |
WO2017080967A1 (en) | 2015-11-12 | 2017-05-18 | F. Hoffmann-La Roche Ag | Compositions for treating spinal muscular atrophy |
-
2015
- 2015-05-11 BR BR112016026205-0A patent/BR112016026205B1/pt active IP Right Grant
- 2015-05-11 CR CR20160518A patent/CR20160518A/es unknown
- 2015-05-11 UA UAA201612716A patent/UA119670C2/uk unknown
- 2015-05-11 CA CA2948561A patent/CA2948561C/en active Active
- 2015-05-11 MX MX2016014547A patent/MX371050B/es active IP Right Grant
- 2015-05-11 EA EA201692280A patent/EA035068B1/ru active Protection Beyond IP Right Term
- 2015-05-11 DK DK15721701T patent/DK3143025T3/da active
- 2015-05-11 SI SI201531021T patent/SI3143025T1/sl unknown
- 2015-05-11 MY MYPI2016001903A patent/MY174284A/en unknown
- 2015-05-11 HR HRP20230637TT patent/HRP20230637T1/hr unknown
- 2015-05-11 PE PE2016002128A patent/PE20170128A1/es unknown
- 2015-05-11 JP JP2016567816A patent/JP6236173B2/ja active Active
- 2015-05-11 ES ES19200058T patent/ES2949660T3/es active Active
- 2015-05-11 NZ NZ72500815A patent/NZ725008A/en unknown
- 2015-05-11 ES ES15721701T patent/ES2761423T3/es active Active
- 2015-05-11 EP EP15721701.9A patent/EP3143025B1/en active Active
- 2015-05-11 KR KR1020217002966A patent/KR102256013B1/ko active IP Right Grant
- 2015-05-11 CN CN201580027306.9A patent/CN106459092B/zh active Active
- 2015-05-11 MA MA051988A patent/MA51988A/fr unknown
- 2015-05-11 WO PCT/EP2015/060343 patent/WO2015173181A1/en active Application Filing
- 2015-05-11 EP EP19200058.6A patent/EP3663296B1/en active Active
- 2015-05-11 PL PL19200058.6T patent/PL3663296T3/pl unknown
- 2015-05-11 KR KR1020167034983A patent/KR102213740B1/ko active IP Right Grant
- 2015-05-11 SG SG11201609497TA patent/SG11201609497TA/en unknown
- 2015-05-11 PT PT157217019T patent/PT3143025T/pt unknown
- 2015-05-11 RS RS20191541A patent/RS59718B1/sr unknown
- 2015-05-11 PL PL15721701T patent/PL3143025T3/pl unknown
- 2015-05-11 MA MA39995A patent/MA39995B1/fr unknown
- 2015-05-11 AU AU2015261046A patent/AU2015261046C1/en active Active
- 2015-05-11 EP EP23169721.0A patent/EP4241772A3/en active Pending
- 2015-05-11 EA EA202090486A patent/EA202090486A3/ru unknown
- 2015-05-11 HU HUE15721701A patent/HUE046491T2/hu unknown
- 2015-05-11 SI SI201531952T patent/SI3663296T1/sl unknown
- 2015-05-14 AR ARP150101500A patent/AR100442A1/es not_active Application Discontinuation
- 2015-05-14 TW TW104115433A patent/TWI667239B/zh active
-
2016
- 2016-10-12 ZA ZA2016/07026A patent/ZA201607026B/en unknown
- 2016-10-19 PH PH12016502081A patent/PH12016502081A1/en unknown
- 2016-10-31 IL IL24865316A patent/IL248653B/en active IP Right Grant
- 2016-11-08 CL CL2016002836A patent/CL2016002836A1/es unknown
- 2016-11-14 US US15/351,267 patent/US9969754B2/en active Active
-
2019
- 2019-10-17 IL IL270027A patent/IL270027B/en active IP Right Grant
- 2019-11-29 HR HRP20192159TT patent/HRP20192159T1/hr unknown
-
2021
- 2021-09-09 FR FR21C1039C patent/FR21C1039I2/fr active Active
- 2021-09-10 NO NO2021035C patent/NO2021035I1/no unknown
- 2021-09-14 LT LTPA2021010C patent/LTPA2021010I1/lt unknown
- 2021-09-14 HU HUS2100037C patent/HUS2100037I1/hu unknown
- 2021-09-15 NL NL301128C patent/NL301128I2/nl unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HRP20192159T1 (hr) | Spojevi za liječenje mišićne atrofije kralježnice | |
IL257587A (en) | Compounds for the treatment of lateral amyotrophic sclerosis | |
HRP20180080T1 (hr) | Pirimidopirimidinoni korisni kao inhibitori wee-1 kinaze | |
HRP20200624T1 (hr) | Derivati 2-(2,4,5-supstituiranog-anilino)pirimidina kao modulatori egfr korisni za liječenje raka | |
HRP20191268T1 (hr) | Derivati tieno[2,3-c]pirol-4-ona kao inhibitori erk | |
NZ628186A (en) | Compounds for treating spinal muscular atrophy | |
PH12016501164A1 (en) | Heteroaryl substituted nicotinamide compounds | |
HRP20160030T1 (hr) | Derivati 6,7-dihidro-pirazolo[1,5-a]pirazin-4-ilamina koji su korisni kao inhibitori beta-sekretaze (bace) | |
HRP20190814T1 (hr) | 7-benzil-4-(2-metilbenzil)-2,4,6,7,8,9-heksahidroimidazo[1,2-a]pirido[3,4-e]pirimidin-5(1h)-on, njegove soli i postupci uporabe | |
HRP20170090T1 (hr) | Heteroaril supstituirani pirolo[2,3-b]piridini i pirolo[2,3-b]pirimidini kao inhibitori janus kinaze | |
HRP20190748T1 (hr) | Derivati policikličkog amida kao inhibitori cdk9 | |
GEP20156417B (en) | Pyrrolo [2,3-d] pyrimidine derivatives as inhibitors of tropomyosin-related kinases | |
MX2023000782A (es) | 7-bencil-4-(2-metilbencilo)-2,4,6,7,8,9-hexahidroimidazo [1,2-a]pirido[3,4-e]pirimidin-5(1h)-ona, analogos y sales del mismo y su uso en terapia. | |
HRP20151071T1 (hr) | Spojevi pirolopirimidina kao inhibitori za cdk4/6 | |
MX2019007073A (es) | Inhibidores de moléculas pequeñas de la familia de quinasas jak. | |
NZ744349A (en) | Pyrazolo[1,5-a]pyrazin-4-yl derivatives as jak-inhibitors | |
NZ604345A (en) | Pyrazolo[1,5-a]pyrimidines as antiviral agents | |
NZ751509A (en) | Combination therapy with 7-benzyl-4-(2-methylbenzyl)-2,4,6,7,8,9-hexahydroimidazo[1,2-a]pyrido[3,4-e]pyrimidin-5(1h)-one | |
MX352831B (es) | Cristales de sal. | |
MX2020002711A (es) | Proceso para preparacion de 7-(4,7-diazaespiro[2.5]octan-7-il)-2-( 2,8-dimetilimidazo[1,2-b]piridazin-6-il)pirido[1,2-a]pirimidin-4- ona. | |
HK1143810A1 (en) | Imidazo [1,2-a] pyrazine compounds for treatment of viral infections such as hepatitis | |
IL239447B (en) | Converted derivatives of tetrahydro[1,2,4]triazolo[alpha-3,4]pyrimidine-5-yl-benzyl and pharmaceutical preparations containing these derivatives | |
RU2015148189A (ru) | ПРОИЗВОДНЫЕ 2-АМИДОПИРИДО[4, 3-d]ПИРИМИДИН-5-ОНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ИНГИБИТОРОВ WEE-1 | |
RU2014151004A (ru) | Пирролопиримидоновые и пирролопиридоновые ингибиторы танкиразы | |
MX2020009586A (es) | Compuestos de (2-azabiciclo[3.1.0]hexan-2-il)pirazolo[1,5-a]pirimi dina e imidazo[1,2-b]piridazina sustituidos como inhibidores de cinasas trk. |