CA2923627C - Atrasentan mandelate salts for the treatment of kidney diseases - Google Patents
Atrasentan mandelate salts for the treatment of kidney diseases Download PDFInfo
- Publication number
- CA2923627C CA2923627C CA2923627A CA2923627A CA2923627C CA 2923627 C CA2923627 C CA 2923627C CA 2923627 A CA2923627 A CA 2923627A CA 2923627 A CA2923627 A CA 2923627A CA 2923627 C CA2923627 C CA 2923627C
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- CA
- Canada
- Prior art keywords
- salt
- atrasentan
- mandelate
- mandelate salt
- crystalline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000006215 rectal suppository Substances 0.000 description 1
- 229960002354 repaglinide Drugs 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 229960000672 rosuvastatin Drugs 0.000 description 1
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011863 silicon-based powder Substances 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 238000000373 single-crystal X-ray diffraction data Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229960002909 spirapril Drugs 0.000 description 1
- HRWCVUIFMSZDJS-SZMVWBNQSA-N spirapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)CC1=CC=CC=C1 HRWCVUIFMSZDJS-SZMVWBNQSA-N 0.000 description 1
- 108700035424 spirapril Proteins 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 229960000943 tartrazine Drugs 0.000 description 1
- 229960000651 tasosartan Drugs 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 229960005187 telmisartan Drugs 0.000 description 1
- 229960001693 terazosin Drugs 0.000 description 1
- VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
- 150000001467 thiazolidinediones Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960005461 torasemide Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940108522 trandate Drugs 0.000 description 1
- 229960002051 trandolapril Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
- 229950005709 vatanidipine Drugs 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229940111503 welchol Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 229940087514 zaroxolyn Drugs 0.000 description 1
- 229960002769 zofenopril Drugs 0.000 description 1
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
- FIKYECRHLXONOX-UHFFFAOYSA-N zolasartan Chemical compound CCCCC1=NC(Cl)=C(C(O)=O)N1CC1=CC=C(OC(=C2Br)C=3C(=CC=CC=3)C3=NNN=N3)C2=C1 FIKYECRHLXONOX-UHFFFAOYSA-N 0.000 description 1
- 229950004433 zolasartan Drugs 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
- C07C59/50—Mandelic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/54—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361877101P | 2013-09-12 | 2013-09-12 | |
| US61/877,101 | 2013-09-12 | ||
| US14/133,297 US8962675B1 (en) | 2013-09-12 | 2013-12-18 | Atrasentan mandelate salts |
| US14/133,297 | 2013-12-18 | ||
| PCT/US2014/054888 WO2015038571A1 (en) | 2013-09-12 | 2014-09-10 | Atrasentan mandelate salts for the treatement of kidney diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2923627A1 CA2923627A1 (en) | 2015-03-19 |
| CA2923627C true CA2923627C (en) | 2022-06-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2923627A Active CA2923627C (en) | 2013-09-12 | 2014-09-10 | Atrasentan mandelate salts for the treatment of kidney diseases |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US8962675B1 (enExample) |
| EP (2) | EP3044222B1 (enExample) |
| JP (1) | JP2016530311A (enExample) |
| CN (1) | CN105745204A (enExample) |
| AU (1) | AU2014318924A1 (enExample) |
| CA (1) | CA2923627C (enExample) |
| CL (1) | CL2016000583A1 (enExample) |
| MX (1) | MX2016003065A (enExample) |
| WO (1) | WO2015038571A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2016103764A (ru) * | 2013-07-08 | 2017-08-11 | Эббви Инк. | Стабилизированные фармацевтические лекарственные формы, содержащие атрасентан |
| CN105905245B (zh) * | 2016-06-03 | 2018-12-25 | 青岛北海船舶重工有限责任公司 | 用于水面无人艇布放回收的吊笼 |
| CN116173014A (zh) | 2019-12-17 | 2023-05-30 | 奇努克医疗公司 | 用阿曲生坦治疗IgA肾病的方法 |
| US20220304979A1 (en) * | 2019-12-17 | 2022-09-29 | Chinook Therapeutics, Inc. | Methods of reducing disease flares |
| CR20230083A (es) | 2020-07-10 | 2023-05-16 | Astrazeneca Ab | Combinación de zibotentan y dapagliflozina para el tratamiento de la enfermedad renal crónica |
| CN120302971A (zh) | 2022-10-28 | 2025-07-11 | 奇努克治疗公司 | 使用内皮素受体拮抗剂和april结合抗体治疗iga肾病 |
Family Cites Families (25)
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| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| US7208517B1 (en) * | 1994-08-19 | 2007-04-24 | Abbott Labortories | Endothelin antagonists |
| US6946481B1 (en) | 1994-08-19 | 2005-09-20 | Abbott Laboratories | Endothelin antagonists |
| US7365093B2 (en) | 1994-08-19 | 2008-04-29 | Abbott Laboratories | Endothelin antagonists |
| US5767144A (en) | 1994-08-19 | 1998-06-16 | Abbott Laboratories | Endothelin antagonists |
| US6162927A (en) | 1994-08-19 | 2000-12-19 | Abbott Laboratories | Endothelin antagonists |
| DE69527072T2 (de) * | 1994-08-19 | 2003-02-13 | Abbott Laboratories, Abbott Park | Endothelin antagoniste |
| US6124341A (en) | 1996-02-13 | 2000-09-26 | Abbott Laboratories | Endothelin antagonists |
| US5801250A (en) | 1996-12-13 | 1998-09-01 | Abbott Laboratories | Process for the stereoselective production of nitro-enamine compounds |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| JP2002524546A (ja) | 1998-09-14 | 2002-08-06 | アボット・ラボラトリーズ | 立体選択性ニトロ化合物の製造方法 |
| US20020055457A1 (en) | 2000-08-07 | 2002-05-09 | Janus Todd J. | Methods of treating cancer and the pain associated therewith using endothelin antagonists |
| WO2002017912A1 (en) * | 2000-08-31 | 2002-03-07 | Abbott Laboratories | Endothelin antagonists |
| US20030022811A1 (en) | 2001-04-11 | 2003-01-30 | Amitabh Singh | Favorable modulation of health-related quality of life and health-related quality-adjusted time-to-progression of disease in patients with prostate cancer |
| US20030092757A1 (en) | 2001-04-11 | 2003-05-15 | Amitabh Singh | Favorable modulation of health-related quality of life and health-related quality-adjusted time-to-progression of disease in patients with prostate cancer |
| UA79248C2 (en) * | 2001-11-09 | 2007-06-11 | Janssen Pharmaceutica Nv | Mandelate salts of substituted tetracyclic tetrahydrofuran derivatives |
| US7297709B2 (en) | 2003-05-22 | 2007-11-20 | Abbott Laboratories | Indazole, benzisoxazole, and benzisothiazole kinase inhibitors |
| WO2006034234A1 (en) | 2004-09-17 | 2006-03-30 | Abbott Laboratories | Crystalline form 3 of atrasentan hydrochloride |
| US20060189675A1 (en) | 2004-09-17 | 2006-08-24 | Steve King | Crystalline form of a drug |
| US20060135596A1 (en) * | 2004-09-17 | 2006-06-22 | Zhang Geoff G | Amorphous form of a drug |
| US20060063825A1 (en) * | 2004-09-17 | 2006-03-23 | Walter Dziki | Crystalline form of a drug |
| US20080132710A1 (en) | 2006-12-04 | 2008-06-05 | Abbott Laboratories | Atrasentan hydrochloride crystalline form 2 |
| EP2294047A2 (en) * | 2008-04-04 | 2011-03-16 | Actavis Group PTC EHF | Novel mandelate salt of fesoterodine |
| US20100184026A1 (en) | 2009-01-22 | 2010-07-22 | Abbott Laboratories | Companion Diagnostic Assays For Endothelin Receptor Antagonists |
-
2013
- 2013-12-18 US US14/133,297 patent/US8962675B1/en active Active
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2014
- 2014-09-10 AU AU2014318924A patent/AU2014318924A1/en not_active Abandoned
- 2014-09-10 CN CN201480061886.9A patent/CN105745204A/zh active Pending
- 2014-09-10 EP EP14780663.2A patent/EP3044222B1/en not_active Not-in-force
- 2014-09-10 WO PCT/US2014/054888 patent/WO2015038571A1/en not_active Ceased
- 2014-09-10 JP JP2016542052A patent/JP2016530311A/ja active Pending
- 2014-09-10 CA CA2923627A patent/CA2923627C/en active Active
- 2014-09-10 MX MX2016003065A patent/MX2016003065A/es unknown
- 2014-09-10 EP EP17172157.4A patent/EP3239148A1/en not_active Withdrawn
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2015
- 2015-01-12 US US14/594,742 patent/US9637476B2/en active Active
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2016
- 2016-03-11 CL CL2016000583A patent/CL2016000583A1/es unknown
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2017
- 2017-03-21 US US15/464,455 patent/US20170190692A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN105745204A (zh) | 2016-07-06 |
| US20150073031A1 (en) | 2015-03-12 |
| US9637476B2 (en) | 2017-05-02 |
| CA2923627A1 (en) | 2015-03-19 |
| EP3044222A1 (en) | 2016-07-20 |
| AU2014318924A1 (en) | 2016-03-17 |
| JP2016530311A (ja) | 2016-09-29 |
| US20170190692A1 (en) | 2017-07-06 |
| US20150126574A1 (en) | 2015-05-07 |
| MX2016003065A (es) | 2016-05-26 |
| EP3044222B1 (en) | 2017-07-05 |
| WO2015038571A1 (en) | 2015-03-19 |
| US8962675B1 (en) | 2015-02-24 |
| EP3239148A1 (en) | 2017-11-01 |
| CL2016000583A1 (es) | 2016-11-11 |
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| Date | Code | Title | Description |
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| EEER | Examination request |
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| EEER | Examination request |
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