ES2419007T3 - Ciertas entidades químicas, composiciones y procedimientos - Google Patents
Ciertas entidades químicas, composiciones y procedimientos Download PDFInfo
- Publication number
- ES2419007T3 ES2419007T3 ES06839401T ES06839401T ES2419007T3 ES 2419007 T3 ES2419007 T3 ES 2419007T3 ES 06839401 T ES06839401 T ES 06839401T ES 06839401 T ES06839401 T ES 06839401T ES 2419007 T3 ES2419007 T3 ES 2419007T3
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- amino
- pyridyl
- fluorophenyl
- carboxamide
- 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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- 150000005829 chemical entities Chemical class 0.000 title claims abstract description 97
- 239000000203 mixture Substances 0.000 title claims abstract description 92
- 238000000034 method Methods 0.000 title claims description 34
- -1 azetidinylcarbonyl Chemical group 0.000 claims abstract description 194
- 150000001875 compounds Chemical class 0.000 claims abstract description 166
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 26
- 239000000651 prodrug Substances 0.000 claims abstract description 16
- 229940002612 prodrug Drugs 0.000 claims abstract description 16
- 150000003857 carboxamides Chemical class 0.000 claims abstract description 12
- RWOJZLDBVIMFNU-QGZVFWFLSA-N 1-[3-[[(3r)-4-(azetidine-1-carbonyl)-3-methylpiperazin-1-yl]methyl]-2-fluorophenyl]-3-(6-methylpyridin-3-yl)urea Chemical compound C([C@H](N(CC1)C(=O)N2CCC2)C)N1CC(C=1F)=CC=CC=1NC(=O)NC1=CC=C(C)N=C1 RWOJZLDBVIMFNU-QGZVFWFLSA-N 0.000 claims abstract description 11
- 230000003993 interaction Effects 0.000 claims abstract description 10
- 230000002503 metabolic effect Effects 0.000 claims abstract description 6
- RWOJZLDBVIMFNU-KRWDZBQOSA-N 1-[3-[[(3s)-4-(azetidine-1-carbonyl)-3-methylpiperazin-1-yl]methyl]-2-fluorophenyl]-3-(6-methylpyridin-3-yl)urea Chemical compound C([C@@H](N(CC1)C(=O)N2CCC2)C)N1CC(C=1F)=CC=CC=1NC(=O)NC1=CC=C(C)N=C1 RWOJZLDBVIMFNU-KRWDZBQOSA-N 0.000 claims abstract description 5
- IZRZYECVCRSANQ-UHFFFAOYSA-N 1-[3-[[4-(azetidin-1-ylsulfonyl)piperazin-1-yl]methyl]-2-fluorophenyl]-3-(6-methylpyridin-3-yl)urea Chemical compound C1=NC(C)=CC=C1NC(=O)NC1=CC=CC(CN2CCN(CC2)S(=O)(=O)N2CCC2)=C1F IZRZYECVCRSANQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001408 amides Chemical class 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- LSTDWADRXDWDAJ-QGZVFWFLSA-N 1-[3-[[(3r)-4-(azetidin-1-ylsulfonyl)-3-methylpiperazin-1-yl]methyl]-2-fluorophenyl]-3-(6-methylpyridin-3-yl)urea Chemical compound C([C@H](N(CC1)S(=O)(=O)N2CCC2)C)N1CC(C=1F)=CC=CC=1NC(=O)NC1=CC=C(C)N=C1 LSTDWADRXDWDAJ-QGZVFWFLSA-N 0.000 claims abstract description 4
- BKQNVWFQTMZAHF-FQEVSTJZSA-N 1-[3-[[(3s)-4-(azetidine-1-carbonyl)-3-(methoxymethyl)piperazin-1-yl]methyl]-2-fluorophenyl]-3-(6-methylpyridin-3-yl)urea Chemical compound C([C@H](N(CC1)C(=O)N2CCC2)COC)N1CC(C=1F)=CC=CC=1NC(=O)NC1=CC=C(C)N=C1 BKQNVWFQTMZAHF-FQEVSTJZSA-N 0.000 claims abstract description 4
- IBCRLWHPBQRTIC-UHFFFAOYSA-N 1-[3-[[4-(azetidin-1-ylsulfonyl)piperazin-1-yl]methyl]-2-fluorophenyl]-3-pyridin-3-ylurea Chemical compound C1=CC=C(NC(=O)NC=2C=NC=CC=2)C(F)=C1CN(CC1)CCN1S(=O)(=O)N1CCC1 IBCRLWHPBQRTIC-UHFFFAOYSA-N 0.000 claims abstract description 4
- ADUAFVNSVUGXNW-UHFFFAOYSA-N 1-[3-[[4-(azetidin-1-ylsulfonyl)piperazin-1-yl]methyl]-2-fluorophenyl]-3-pyridin-4-ylurea Chemical compound C1=CC=C(NC(=O)NC=2C=CN=CC=2)C(F)=C1CN(CC1)CCN1S(=O)(=O)N1CCC1 ADUAFVNSVUGXNW-UHFFFAOYSA-N 0.000 claims abstract description 4
- URSIUTCWIJKKNU-UHFFFAOYSA-N 1-[3-[[4-(azetidine-1-carbonyl)piperazin-1-yl]methyl]-2-fluorophenyl]-3-(2-methylpyridin-4-yl)urea Chemical compound C1=NC(C)=CC(NC(=O)NC=2C(=C(CN3CCN(CC3)C(=O)N3CCC3)C=CC=2)F)=C1 URSIUTCWIJKKNU-UHFFFAOYSA-N 0.000 claims abstract description 4
- RBCGCWFOCMVKSW-UHFFFAOYSA-N 1-[3-[[4-(azetidine-1-carbonyl)piperazin-1-yl]methyl]-2-fluorophenyl]-3-pyridin-4-ylurea Chemical compound C1=CC=C(NC(=O)NC=2C=CN=CC=2)C(F)=C1CN(CC1)CCN1C(=O)N1CCC1 RBCGCWFOCMVKSW-UHFFFAOYSA-N 0.000 claims abstract description 4
- BWGTYOAYFTZNHW-VYIQYICTSA-N C1=NC(C)=CC(NC(=O)NC=2C(=C(CN3CCN(CC3)C(=N/C#N)\N3CCC3)C=CC=2)F)=C1 Chemical compound C1=NC(C)=CC(NC(=O)NC=2C(=C(CN3CCN(CC3)C(=N/C#N)\N3CCC3)C=CC=2)F)=C1 BWGTYOAYFTZNHW-VYIQYICTSA-N 0.000 claims abstract description 4
- QUVBTHZWUBQHGU-VYIQYICTSA-N C1=NC(C)=CC=C1NC(=O)NC1=CC=CC(CN2CCN(CC2)C(=N/C#N)\N2CCC2)=C1F Chemical compound C1=NC(C)=CC=C1NC(=O)NC1=CC=CC(CN2CCN(CC2)C(=N/C#N)\N2CCC2)=C1F QUVBTHZWUBQHGU-VYIQYICTSA-N 0.000 claims abstract description 4
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- 238000012545 processing Methods 0.000 claims abstract description 4
- VWJPDGKKRPWPGA-UHFFFAOYSA-N 1-[3-[[4-(azetidine-1-carbonyl)piperazin-1-yl]methyl]-2-fluorophenyl]-3-(6-methylpyridin-3-yl)urea Chemical compound C1=NC(C)=CC=C1NC(=O)NC1=CC=CC(CN2CCN(CC2)C(=O)N2CCC2)=C1F VWJPDGKKRPWPGA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 206010019280 Heart failures Diseases 0.000 claims description 44
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 15
- KXNAOTCKJOXZDZ-UHFFFAOYSA-N (6-methylpyridin-3-yl)urea Chemical compound CC1=CC=C(NC(N)=O)C=N1 KXNAOTCKJOXZDZ-UHFFFAOYSA-N 0.000 claims description 12
- 208000019622 heart disease Diseases 0.000 claims description 11
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- 239000003814 drug Substances 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
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- 239000006187 pill Substances 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- WHXXDKTZNZZCQL-FQEVSTJZSA-N 1-[3-[[(3s)-4-(azetidin-1-ylsulfonyl)-3-(methoxymethyl)piperazin-1-yl]methyl]-2-fluorophenyl]-3-(6-methylpyridin-3-yl)urea Chemical compound C([C@H](N(CC1)S(=O)(=O)N2CCC2)COC)N1CC(C=1F)=CC=CC=1NC(=O)NC1=CC=C(C)N=C1 WHXXDKTZNZZCQL-FQEVSTJZSA-N 0.000 claims description 2
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- 208000008253 Systolic Heart Failure Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 159
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 131
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 127
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 127
- 239000000243 solution Substances 0.000 description 102
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 93
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 87
- 239000011541 reaction mixture Substances 0.000 description 80
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 67
- 238000006243 chemical reaction Methods 0.000 description 60
- 125000000217 alkyl group Chemical group 0.000 description 56
- 239000011575 calcium Substances 0.000 description 56
- 235000019439 ethyl acetate Nutrition 0.000 description 56
- 125000001072 heteroaryl group Chemical group 0.000 description 56
- 230000000694 effects Effects 0.000 description 49
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 48
- 229910052791 calcium Inorganic materials 0.000 description 48
- 239000012074 organic phase Substances 0.000 description 46
- 102000003505 Myosin Human genes 0.000 description 45
- 108060008487 Myosin Proteins 0.000 description 43
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 43
- 238000012360 testing method Methods 0.000 description 43
- 230000000747 cardiac effect Effects 0.000 description 42
- 239000001257 hydrogen Substances 0.000 description 41
- 229910052739 hydrogen Inorganic materials 0.000 description 41
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 39
- 239000012267 brine Substances 0.000 description 38
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
- 239000007787 solid Substances 0.000 description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 35
- 229910052938 sodium sulfate Inorganic materials 0.000 description 35
- 235000011152 sodium sulphate Nutrition 0.000 description 35
- 238000000746 purification Methods 0.000 description 34
- 125000003118 aryl group Chemical group 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 238000001802 infusion Methods 0.000 description 28
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- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 26
- 241001465754 Metazoa Species 0.000 description 26
- 150000002431 hydrogen Chemical group 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 25
- 125000000753 cycloalkyl group Chemical group 0.000 description 25
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 25
- 125000001424 substituent group Chemical group 0.000 description 25
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 24
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 24
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 241000700159 Rattus Species 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 210000000107 myocyte Anatomy 0.000 description 21
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 21
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 20
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- KLYUFZKTGVXUOC-FQEVSTJZSA-N tert-butyl n-[(3s)-1-[[4-fluoro-3-[(6-methylpyridin-3-yl)carbamoylamino]phenyl]methyl]piperidin-3-yl]-n-methylcarbamate Chemical compound C1[C@@H](N(C)C(=O)OC(C)(C)C)CCCN1CC1=CC=C(F)C(NC(=O)NC=2C=NC(C)=CC=2)=C1 KLYUFZKTGVXUOC-FQEVSTJZSA-N 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- UPCXAARSWVHVLY-UHFFFAOYSA-N tris(2-hydroxyethyl)azanium;acetate Chemical compound CC(O)=O.OCCN(CCO)CCO UPCXAARSWVHVLY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
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- 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
- A61K31/4965—Non-condensed pyrazines
-
- 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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines 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
- A61K31/535—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
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75140005P | 2005-12-15 | 2005-12-15 | |
| US751400P | 2005-12-15 | ||
| US75635606P | 2006-01-04 | 2006-01-04 | |
| US756356P | 2006-01-04 | ||
| US81797506P | 2006-06-29 | 2006-06-29 | |
| US817975P | 2006-06-29 | ||
| PCT/US2006/047976 WO2007070683A2 (en) | 2005-12-15 | 2006-12-14 | Certain chemical entities, compositions and methods |
Publications (1)
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|---|---|
| ES2419007T3 true ES2419007T3 (es) | 2013-08-19 |
Family
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Family Applications (1)
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|---|---|---|---|
| ES06839401T Active ES2419007T3 (es) | 2005-12-15 | 2006-12-14 | Ciertas entidades químicas, composiciones y procedimientos |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US20070161617A1 (https=) |
| EP (1) | EP1959960B1 (https=) |
| JP (1) | JP5301284B2 (https=) |
| AR (1) | AR058347A1 (https=) |
| ES (1) | ES2419007T3 (https=) |
| PE (1) | PE20071161A1 (https=) |
| TW (1) | TW200808321A (https=) |
| WO (1) | WO2007070683A2 (https=) |
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| ATE552236T1 (de) * | 2003-01-14 | 2012-04-15 | Cytokinetics Inc | Verbindungen, zusammensetzungen und verfahren zur behandlung von herzinsuffizienz |
| ES2522579T3 (es) | 2004-06-17 | 2014-11-17 | Cytokinetics, Inc. | Compuestos, composiciones y métodos |
| US7825120B2 (en) * | 2005-12-15 | 2010-11-02 | Cytokinetics, Inc. | Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas |
| EP1959947A2 (en) * | 2005-12-15 | 2008-08-27 | Cytokinetics, Inc. | Certain chemical entities, compositions and methods |
| ES2419007T3 (es) * | 2005-12-15 | 2013-08-19 | Cytokinetics, Inc. | Ciertas entidades químicas, composiciones y procedimientos |
| US20070208000A1 (en) * | 2005-12-15 | 2007-09-06 | Morgan Bradley P | Certain chemical entities, compositions and methods |
| WO2007078815A2 (en) * | 2005-12-16 | 2007-07-12 | Cytokinetics, Inc. | Certain chemical entities, compositions, and methods |
| WO2007078839A2 (en) | 2005-12-19 | 2007-07-12 | Cytokinetics, Inc. | Compounds, compositions and methods |
| SG11201507258PA (en) * | 2013-03-14 | 2015-10-29 | Amgen Inc | Heterocyclic compounds and their uses |
| US9895308B2 (en) * | 2013-03-14 | 2018-02-20 | Amgen Inc. | Heterocyclic compounds and their uses |
| DK3645002T3 (da) | 2017-06-30 | 2024-12-16 | Amgen Inc | Fremgangsmåder til behandling af hjertesvigt med hjerte-sarkomer-aktivatorer |
| AU2018294254C1 (en) * | 2017-06-30 | 2022-10-13 | Amgen Inc. | Synthesis of omecamtiv mecarbil |
| PE20200924A1 (es) | 2017-09-13 | 2020-09-14 | Amgen Inc | Compuestos de bisamida sustituida que activan el sarcomero cardiaco |
| PT3594199T (pt) | 2018-07-09 | 2020-09-04 | Amgen Inc | 2-fluoro-3-nitrotolueno cristalino e processo para a sua preparação |
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| WO2020131574A1 (en) | 2018-12-18 | 2020-06-25 | Amgen Inc. | Method of reducing aromatic nitro compounds |
| CN110124046B (zh) * | 2019-06-11 | 2023-04-07 | 辽宁大学 | 一种氧化石墨烯负载双氯芬酸二乙胺及其制备方法 |
| US20230090391A1 (en) * | 2020-02-10 | 2023-03-23 | Amgen Inc. | Omecamtiv mecarbil tablet |
| DK4243825T3 (da) | 2020-11-12 | 2025-12-01 | Amgen Inc | Omecamtiv mecarbil til behandling af hjerteinsattsvigt hos udvalgte patientgrupper |
| IL305751A (en) | 2021-03-10 | 2023-11-01 | Amgen Inc | SYNTHESIS OF OMECAMTIV MECARBIL |
| US11986474B1 (en) | 2023-06-27 | 2024-05-21 | Cytokinetics, Incorporated | Methods for treating heart failure by administering cardiac sarcomere activators |
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- 2006-12-14 US US11/640,438 patent/US20070161617A1/en not_active Abandoned
- 2006-12-14 WO PCT/US2006/047976 patent/WO2007070683A2/en not_active Ceased
- 2006-12-14 EP EP06839401.4A patent/EP1959960B1/en active Active
- 2006-12-14 AR ARP060105509A patent/AR058347A1/es unknown
- 2006-12-14 TW TW095146918A patent/TW200808321A/zh unknown
- 2006-12-14 JP JP2008545855A patent/JP5301284B2/ja active Active
- 2006-12-15 PE PE2006001613A patent/PE20071161A1/es not_active Application Discontinuation
-
2009
- 2009-06-11 US US12/483,093 patent/US8445495B2/en active Active
-
2013
- 2013-05-17 US US13/897,086 patent/US8871768B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP1959960A4 (en) | 2010-08-04 |
| PE20071161A1 (es) | 2008-02-03 |
| JP2009519951A (ja) | 2009-05-21 |
| WO2007070683A3 (en) | 2008-11-20 |
| WO2007070683A2 (en) | 2007-06-21 |
| TW200808321A (en) | 2008-02-16 |
| EP1959960A2 (en) | 2008-08-27 |
| US8445495B2 (en) | 2013-05-21 |
| US20100029680A1 (en) | 2010-02-04 |
| AR058347A1 (es) | 2008-01-30 |
| EP1959960B1 (en) | 2013-04-10 |
| JP5301284B2 (ja) | 2013-09-25 |
| US8871768B2 (en) | 2014-10-28 |
| US20070161617A1 (en) | 2007-07-12 |
| US20130324549A1 (en) | 2013-12-05 |
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