HRP20241617T1 - Piridazinilni amino-derivati kao inhibitori alk5 - Google Patents
Piridazinilni amino-derivati kao inhibitori alk5 Download PDFInfo
- Publication number
- HRP20241617T1 HRP20241617T1 HRP20241617TT HRP20241617T HRP20241617T1 HR P20241617 T1 HRP20241617 T1 HR P20241617T1 HR P20241617T T HRP20241617T T HR P20241617TT HR P20241617 T HRP20241617 T HR P20241617T HR P20241617 T1 HRP20241617 T1 HR P20241617T1
- Authority
- HR
- Croatia
- Prior art keywords
- fluorophenyl
- chloro
- amino
- pyridin
- pyridazin
- Prior art date
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- -1 PYRIDAZINYL AMINO Chemical class 0.000 title claims 16
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 73
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 206010016654 Fibrosis Diseases 0.000 claims 4
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 230000004761 fibrosis Effects 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- RAYIKMXTWRUOPJ-UHFFFAOYSA-N 2-(4-ethylpiperazin-1-ium-1-yl)-2-methylpropanoate Chemical compound CCN1CCN(C(C)(C)C(O)=O)CC1 RAYIKMXTWRUOPJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 206010054793 Arterial fibrosis Diseases 0.000 claims 1
- OEYWMVKCMARLOK-UHFFFAOYSA-N CC(C)C(C=C1)=CC(C2=CC(NC3=CC=NC4=CC(OCCN5CCN(C)CC5)=CC=C34)=CN=N2)=C1F Chemical compound CC(C)C(C=C1)=CC(C2=CC(NC3=CC=NC4=CC(OCCN5CCN(C)CC5)=CC=C34)=CN=N2)=C1F OEYWMVKCMARLOK-UHFFFAOYSA-N 0.000 claims 1
- CBRDAYRXLUOQFR-UHFFFAOYSA-N CC(C)N(CCN(CCC(NC1=NC=CC(NC2=C(C)N=NC(C(C=C(C=C3)Cl)=C3F)=C2)=C1)=O)C1)C1C(OC)=O Chemical compound CC(C)N(CCN(CCC(NC1=NC=CC(NC2=C(C)N=NC(C(C=C(C=C3)Cl)=C3F)=C2)=C1)=O)C1)C1C(OC)=O CBRDAYRXLUOQFR-UHFFFAOYSA-N 0.000 claims 1
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- 206010019668 Hepatic fibrosis Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- FRPLNQOOYIHEMR-UHFFFAOYSA-N N#CCCN1CCN(CCC(NC2=NC=CC(NC3=C(C(F)(F)F)N=NC(C(C=C(C=C4)Cl)=C4F)=C3)=C2)=O)CC1 Chemical compound N#CCCN1CCN(CCC(NC2=NC=CC(NC3=C(C(F)(F)F)N=NC(C(C=C(C=C4)Cl)=C4F)=C3)=C2)=O)CC1 FRPLNQOOYIHEMR-UHFFFAOYSA-N 0.000 claims 1
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- FHSCSRVTEPNKGX-UHFFFAOYSA-N N-[4-[[6-(5-chloro-2-fluorophenyl)-3-methylpyridazin-4-yl]amino]pyridin-2-yl]-2-piperazin-1-ylacetamide Chemical compound CC(N=NC(C(C=C(C=C1)Cl)=C1F)=C1)=C1NC1=CC(NC(CN2CCNCC2)=O)=NC=C1 FHSCSRVTEPNKGX-UHFFFAOYSA-N 0.000 claims 1
- DXMDCTFKERDDQJ-UHFFFAOYSA-N N-[4-[[6-(5-chloro-2-fluorophenyl)-3-methylpyridazin-4-yl]amino]pyridin-2-yl]-3-[3-(hydroxymethyl)-4-methylpiperazin-1-yl]propanamide Chemical compound CC(N=NC(C(C=C(C=C1)Cl)=C1F)=C1)=C1NC1=CC(NC(CCN2CC(CO)N(C)CC2)=O)=NC=C1 DXMDCTFKERDDQJ-UHFFFAOYSA-N 0.000 claims 1
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- GHYLVDJWXQEOCX-UHFFFAOYSA-N O=C(C1CC1)NC1=NC=CC(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=C1 Chemical compound O=C(C1CC1)NC1=NC=CC(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=C1 GHYLVDJWXQEOCX-UHFFFAOYSA-N 0.000 claims 1
- QFNPDRGXNNTEOB-UHFFFAOYSA-N O=C(CCCN1CCOCC1)NC1=NC=CC(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=C1 Chemical compound O=C(CCCN1CCOCC1)NC1=NC=CC(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=C1 QFNPDRGXNNTEOB-UHFFFAOYSA-N 0.000 claims 1
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- QHQGMDZIOXZSAE-UHFFFAOYSA-N O=C(CCN1CCNCC1)NC1=NC=CC(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=C1 Chemical compound O=C(CCN1CCNCC1)NC1=NC=CC(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=C1 QHQGMDZIOXZSAE-UHFFFAOYSA-N 0.000 claims 1
- VXBMRCPBEOLVNM-UHFFFAOYSA-N O=C(CCN1CCOCC1)NC1=NC=CC(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=C1 Chemical compound O=C(CCN1CCOCC1)NC1=NC=CC(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=C1 VXBMRCPBEOLVNM-UHFFFAOYSA-N 0.000 claims 1
- BLGZYKBWSIPPFL-UHFFFAOYSA-N O=C(N(C1)CC1N1CCCC1)OC1=CC=C(C(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=CC=N2)C2=C1 Chemical compound O=C(N(C1)CC1N1CCCC1)OC1=CC=C(C(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=CC=N2)C2=C1 BLGZYKBWSIPPFL-UHFFFAOYSA-N 0.000 claims 1
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- YKZROSDJGMYWLD-UHFFFAOYSA-N OCCC(CCO)N1CCN(CCOC2=CC=C(C(NC3=CN=NC(C(C=C(C=C4)Cl)=C4F)=C3)=CC=N3)C3=C2)CC1 Chemical compound OCCC(CCO)N1CCN(CCOC2=CC=C(C(NC3=CN=NC(C(C=C(C=C4)Cl)=C4F)=C3)=CC=N3)C3=C2)CC1 YKZROSDJGMYWLD-UHFFFAOYSA-N 0.000 claims 1
- PWBHQALTJPAMBD-UHFFFAOYSA-N OCCN(CC1)CCN1C(OC1=CC=C(C(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=CC=N2)C2=C1)=O Chemical compound OCCN(CC1)CCN1C(OC1=CC=C(C(NC2=CN=NC(C(C=C(C=C3)Cl)=C3F)=C2)=CC=N2)C2=C1)=O PWBHQALTJPAMBD-UHFFFAOYSA-N 0.000 claims 1
- UDCXSIWGTZGVLS-UHFFFAOYSA-N OCCN(CCN1CCN(CCOC2=CC=C(C(NC3=CN=NC(C(C=C(C=C4)Cl)=C4F)=C3)=CC=N3)C3=C2)CC1)CCO Chemical compound OCCN(CCN1CCN(CCOC2=CC=C(C(NC3=CN=NC(C(C=C(C=C4)Cl)=C4F)=C3)=CC=N3)C3=C2)CC1)CCO UDCXSIWGTZGVLS-UHFFFAOYSA-N 0.000 claims 1
- TZSIDHUQFVOFIW-UHFFFAOYSA-N OCCN1CCN(CCC(NC2=NC=CC(NC3=C(C(F)(F)F)N=NC(C(C=C(C=C4)Cl)=C4F)=C3)=C2)=O)CC1 Chemical compound OCCN1CCN(CCC(NC2=NC=CC(NC3=C(C(F)(F)F)N=NC(C(C=C(C=C4)Cl)=C4F)=C3)=C2)=O)CC1 TZSIDHUQFVOFIW-UHFFFAOYSA-N 0.000 claims 1
- HWSIPFXXHNTZOG-UHFFFAOYSA-N OCCN1CCN(CCOC2=CC=C(C(NC3=CN=NC(C(C=C(C=C4)Cl)=C4F)=C3)=CC=N3)C3=C2)CC1 Chemical compound OCCN1CCN(CCOC2=CC=C(C(NC3=CN=NC(C(C=C(C=C4)Cl)=C4F)=C3)=CC=N3)C3=C2)CC1 HWSIPFXXHNTZOG-UHFFFAOYSA-N 0.000 claims 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 230000009787 cardiac fibrosis Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- GCDDETLSKIAHHR-UHFFFAOYSA-N ethyl 1-methylpiperazine-2-carboxylate Chemical compound CCOC(=O)C1CNCCN1C GCDDETLSKIAHHR-UHFFFAOYSA-N 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- VQXJLGJJFHNUHC-UHFFFAOYSA-N n-[2-(4-ethylpiperazin-1-yl)ethyl]acetamide Chemical compound CCN1CCN(CCNC(C)=O)CC1 VQXJLGJJFHNUHC-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 1
- 201000002793 renal fibrosis Diseases 0.000 claims 1
- 230000019491 signal transduction Effects 0.000 claims 1
Classifications
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- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- 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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- 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
- A61K31/535—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- 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
- C07D471/10—Spiro-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
- 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
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20185890 | 2020-07-15 | ||
| PCT/EP2021/069649 WO2022013307A1 (en) | 2020-07-15 | 2021-07-14 | Pyridazinyl amino derivatives as alk5 inhibitors |
| EP21743186.5A EP4182308B1 (en) | 2020-07-15 | 2021-07-14 | Pyridazinyl amino derivatives as alk5 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20241617T1 true HRP20241617T1 (hr) | 2025-01-31 |
Family
ID=71620257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20241617TT HRP20241617T1 (hr) | 2020-07-15 | 2021-07-14 | Piridazinilni amino-derivati kao inhibitori alk5 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US12479826B2 (https=) |
| EP (1) | EP4182308B1 (https=) |
| JP (1) | JP7686741B2 (https=) |
| KR (1) | KR20230051500A (https=) |
| CN (1) | CN116096719B (https=) |
| AR (1) | AR122986A1 (https=) |
| AU (1) | AU2021307559A1 (https=) |
| BR (1) | BR112023000588A8 (https=) |
| CA (1) | CA3184990A1 (https=) |
| DK (1) | DK4182308T3 (https=) |
| ES (1) | ES2997111T3 (https=) |
| FI (1) | FI4182308T3 (https=) |
| HR (1) | HRP20241617T1 (https=) |
| HU (1) | HUE069150T2 (https=) |
| MX (1) | MX2023000521A (https=) |
| PL (1) | PL4182308T3 (https=) |
| PT (1) | PT4182308T (https=) |
| SI (1) | SI4182308T1 (https=) |
| WO (1) | WO2022013307A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP7702205B2 (ja) * | 2021-09-15 | 2025-07-03 | 株式会社東芝 | 新規アミン化合物、酸性ガス吸収剤、酸性ガスの除去方法及び酸性ガス除去 |
| CN114957331A (zh) * | 2022-04-22 | 2022-08-30 | 北京康辰药业股份有限公司 | 磷酸酯取代的环丙酰胺衍生喹唑啉类化合物的制备方法 |
| WO2024180206A1 (en) | 2023-03-02 | 2024-09-06 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as alk5 inhibitors |
| WO2024180207A1 (en) | 2023-03-02 | 2024-09-06 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as alk5 inhibitors |
| KR20240159754A (ko) * | 2023-04-28 | 2024-11-06 | 한국원자력의학원 | N-메틸피페라진 에탄올 카바메이트(N-methylpiperazine ethanol carbamate) 구조를 포함하는 신규 화합물 및 이의 용도 |
| WO2025132458A1 (en) | 2023-12-18 | 2025-06-26 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as alk5 inhibitors |
| WO2025132460A1 (en) | 2023-12-18 | 2025-06-26 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as alk5 inhibitors |
Family Cites Families (19)
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| DE60001229T2 (de) | 1999-04-09 | 2003-10-30 | Smithkline Beecham Corp., Philadelphia | Triarylimidazole |
| AR029803A1 (es) | 2000-02-21 | 2003-07-16 | Smithkline Beecham Plc | Imidazoles sustituidos con piridilo y composiciones farmaceuticas que las comprenden |
| GB0007405D0 (en) | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
| EP1317450B1 (en) * | 2000-09-15 | 2006-11-22 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| CA2423050A1 (en) | 2000-09-20 | 2002-03-28 | Ortho-Mcneil Pharmaceutical, Inc. | Pyrazine derivatives as modulators of tyrosine kinases |
| AR039241A1 (es) | 2002-04-04 | 2005-02-16 | Biogen Inc | Heteroarilos trisustituidos y metodos para su produccion y uso de los mismos |
| JP2006503043A (ja) * | 2002-09-10 | 2006-01-26 | サイオス インク． | ＴＧＦβ阻害剤 |
| AU2004278382B2 (en) * | 2003-09-30 | 2008-09-18 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| BRPI0714409A2 (pt) | 2006-07-14 | 2013-03-12 | Novartis Ag | derivados de pirimidina como inibidores de alk-5 |
| ES2375425T3 (es) | 2007-07-26 | 2012-02-29 | Novartis Ag | Compuestos org�?nicos. |
| BRPI0817434A2 (pt) | 2007-10-17 | 2015-06-16 | Novartis Ag | Composto orgânicos |
| AR070127A1 (es) | 2008-01-11 | 2010-03-17 | Novartis Ag | Pirrolo - pirimidinas y pirrolo -piridinas |
| MX2010007604A (es) | 2008-01-11 | 2010-08-02 | Novartis Ag | Pirimidinas como inhibidores de cinasa. |
| US8343966B2 (en) | 2008-01-11 | 2013-01-01 | Novartis Ag | Organic compounds |
| EA201001687A1 (ru) | 2008-04-29 | 2011-06-30 | Новартис Аг | Производные имидазопиридина в качестве ингибиторов активиноподобной рецепторной киназы ( alk-4 или alk-5 ) |
| CN102596200A (zh) * | 2009-11-07 | 2012-07-18 | 默克专利有限公司 | 作为TGF-β受体激酶抑制剂的杂芳基氨基喹啉类 |
| DK2731949T3 (en) | 2011-07-13 | 2018-06-14 | Tiumbio Co Ltd | 2-PYRIDYL-SUBSTITUTED IMIDAZOLS AS ALK5 AND / OR ALK4 INHIBITORS |
| HRP20201384T1 (hr) * | 2014-01-01 | 2020-11-27 | Medivation Technologies Llc | Spojevi i postupci njihove upotrebe |
| US20200247812A1 (en) * | 2018-07-10 | 2020-08-06 | Integral Biosciences Private Limited | Heterocyclic compounds and methods of use |
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| ES2997111T3 (en) | 2025-03-19 |
| AR122986A1 (es) | 2022-10-19 |
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| CA3184990A1 (en) | 2022-01-20 |
| WO2022013307A1 (en) | 2022-01-20 |
| PT4182308T (pt) | 2024-12-04 |
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| US12479826B2 (en) | 2025-11-25 |
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| US20240018122A1 (en) | 2024-01-18 |
| CN116096719A (zh) | 2023-05-09 |
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| FI4182308T3 (fi) | 2024-12-07 |
| HUE069150T2 (hu) | 2025-02-28 |
| PL4182308T3 (pl) | 2025-01-07 |
| EP4182308B1 (en) | 2024-09-04 |
| CN116096719B (zh) | 2025-09-30 |
| MX2023000521A (es) | 2023-02-13 |
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