IL303220A - 4-(2-fluoro-4-methoxy-5-3-(((1-methylcyclobutyl)methyl)carbamoyl)bicyclo[2.2.1]heptan-2-yl)carbamoyl)phenoxy)-1-methylcyclohexane-1-carboxylic acid derivatives and similar compounds as rxfp1 modulators for the treatment of heart failure - Google Patents
4-(2-fluoro-4-methoxy-5-3-(((1-methylcyclobutyl)methyl)carbamoyl)bicyclo[2.2.1]heptan-2-yl)carbamoyl)phenoxy)-1-methylcyclohexane-1-carboxylic acid derivatives and similar compounds as rxfp1 modulators for the treatment of heart failureInfo
- Publication number
- IL303220A IL303220A IL303220A IL30322023A IL303220A IL 303220 A IL303220 A IL 303220A IL 303220 A IL303220 A IL 303220A IL 30322023 A IL30322023 A IL 30322023A IL 303220 A IL303220 A IL 303220A
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- Prior art keywords
- compound
- substituted
- substituents
- ome
- membered
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 97
- 206010019280 Heart failures Diseases 0.000 title claims 4
- -1 (1-METHYLCYCLOBUTYL)METHYL Chemical class 0.000 title claims 3
- WVKPYYLOFMTDHB-UHFFFAOYSA-N 2-norbornyl radical Chemical compound C1CC2[CH]CC1C2 WVKPYYLOFMTDHB-UHFFFAOYSA-N 0.000 title claims 2
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 title 2
- 101000869643 Homo sapiens Relaxin receptor 1 Proteins 0.000 title 1
- 102100032444 Relaxin receptor 1 Human genes 0.000 title 1
- 239000002253 acid Substances 0.000 title 1
- 125000001424 substituent group Chemical group 0.000 claims 44
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 24
- 238000000634 powder X-ray diffraction Methods 0.000 claims 24
- 125000005842 heteroatom Chemical group 0.000 claims 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 20
- 229910052760 oxygen Chemical group 0.000 claims 20
- 239000001301 oxygen Chemical group 0.000 claims 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims 18
- 125000002950 monocyclic group Chemical group 0.000 claims 17
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 15
- 229910002483 Cu Ka Inorganic materials 0.000 claims 14
- 230000005855 radiation Effects 0.000 claims 14
- 125000002947 alkylene group Chemical group 0.000 claims 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 11
- 229910052717 sulfur Chemical group 0.000 claims 11
- 239000011593 sulfur Chemical group 0.000 claims 11
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000003367 polycyclic group Chemical group 0.000 claims 7
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000033626 Renal failure acute Diseases 0.000 claims 1
- 201000011040 acute kidney failure Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 208000038002 heart failure with reduced ejection fraction Diseases 0.000 claims 1
- 125000004474 heteroalkylene group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005549 heteroarylene group Chemical group 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
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- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A61P13/00—Drugs for disorders of the urinary system
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/38—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing five carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202063122690P | 2020-12-08 | 2020-12-08 | |
| PCT/EP2021/084673 WO2022122773A1 (en) | 2020-12-08 | 2021-12-07 | 4-(2-fluoro-4-methoxy-5-3-(((1-methylcyclobutyl)methyl)carbamoyl)bicyclo[2.2.1]heptan-2-yl)carbamoyl)phenoxy)-1-methylcyclohexane-1-carboxylic acid derivatives and similar compounds as rxfp1 modulators for the treatment of heart failure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL303220A true IL303220A (en) | 2023-07-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL303220A IL303220A (en) | 2020-12-08 | 2021-12-07 | 4-(2-fluoro-4-methoxy-5-3-(((1-methylcyclobutyl)methyl)carbamoyl)bicyclo[2.2.1]heptan-2-yl)carbamoyl)phenoxy)-1-methylcyclohexane-1-carboxylic acid derivatives and similar compounds as rxfp1 modulators for the treatment of heart failure |
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Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4423058A1 (en) * | 2021-10-29 | 2024-09-04 | Bristol-Myers Squibb Company | Rxfp1 agonists |
| EP4423094B1 (en) * | 2021-10-29 | 2025-12-10 | Bristol-Myers Squibb Company | Rxfp1 modulators for the treatment of heart failure |
| IL312125A (en) * | 2021-10-29 | 2024-06-01 | Bristol Myers Squibb Co | Rxfp1 agonists |
| JP2024540163A (ja) * | 2021-10-29 | 2024-10-31 | ブリストル－マイヤーズ スクイブ カンパニー | Ｒｘｆｐ１アゴニスト |
| CN119325376A (zh) * | 2022-06-07 | 2025-01-17 | 阿斯利康(瑞典)有限公司 | Rxfp1调节剂和sglt2抑制剂的组合 |
| CN119630638A (zh) * | 2022-06-07 | 2025-03-14 | 阿斯利康(瑞典)有限公司 | Rxfp1调节剂的固体形式 |
| US20260069558A1 (en) * | 2022-06-07 | 2026-03-12 | Astrazeneca Ab | Rxfp1 modulators for treating resistant hypertension or heart failure with pulmonary hypertension |
| CN121605099A (zh) * | 2023-08-10 | 2026-03-03 | 深圳信立泰药业股份有限公司 | 一种rxfp1受体调节剂及其制备方法和医药用途 |
| IL326543A (en) | 2023-08-15 | 2026-04-01 | Astrazeneca Ab | Compound azd5462 for use in the treatment of heart failure |
| TW202530177A (zh) * | 2023-10-13 | 2025-08-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 醯胺取代的環烷基類化合物、其製備方法及其在醫藥上的應用 |
| KR20260116187A (ko) | 2023-11-17 | 2026-07-28 | 일라이 릴리 앤드 캄파니 | Rxfp1 수용체 효능제 |
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| US5223534A (en) * | 1989-12-04 | 1993-06-29 | G. D. Searle & Co. | Benzofuuranyl/benofuranylaklyl-N-terminal cycloalkoxy-C-terminal amino hydroxy β-amino acid derivatives |
| WO2004041795A1 (en) * | 2002-10-30 | 2004-05-21 | Guilford Pharmaceuticals Inc. | Novel inhibitors of dipeptidyl peptidase iv |
| US9452973B2 (en) * | 2012-05-04 | 2016-09-27 | The United States Of America, As Represented By The Secretary Department Of Health And Human Services | Modulators of the relaxin receptor 1 |
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2021
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- 2021-12-07 CN CN202180075461.3A patent/CN116547270A/zh active Pending
- 2021-12-07 WO PCT/EP2021/084673 patent/WO2022122773A1/en not_active Ceased
- 2021-12-07 TW TW110145574A patent/TW202237559A/zh unknown
- 2021-12-07 KR KR1020237022785A patent/KR20230118142A/ko active Pending
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- 2021-12-07 AR ARP210103397A patent/AR124193A1/es unknown
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2023
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Also Published As
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|---|---|
| CN116547270A (zh) | 2023-08-04 |
| JP2023552793A (ja) | 2023-12-19 |
| CO2023008303A2 (es) | 2023-09-18 |
| US20230348363A1 (en) | 2023-11-02 |
| AU2021395353A9 (en) | 2024-02-08 |
| UY39559A (es) | 2022-06-30 |
| AU2021395353B2 (en) | 2024-08-29 |
| US11667602B2 (en) | 2023-06-06 |
| AU2021395353A1 (en) | 2023-07-13 |
| KR20230118142A (ko) | 2023-08-10 |
| US20230078576A1 (en) | 2023-03-16 |
| AR124193A1 (es) | 2023-02-22 |
| ECSP23050133A (es) | 2023-08-31 |
| MX2023006178A (es) | 2023-06-08 |
| WO2022122773A1 (en) | 2022-06-16 |
| EP4259605A1 (en) | 2023-10-18 |
| PE20240655A1 (es) | 2024-04-04 |
| CA3203024A1 (en) | 2022-06-16 |
| DOP2023000111A (es) | 2023-07-09 |
| CR20230296A (es) | 2023-09-01 |
| TW202237559A (zh) | 2022-10-01 |
| CL2023001572A1 (es) | 2023-12-15 |
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