ES2591156T3 - Inhibidores de F1F0-ATPasas de tipo piridonil guanidina y sus usos terapéuticos - Google Patents
Inhibidores de F1F0-ATPasas de tipo piridonil guanidina y sus usos terapéuticos Download PDFInfo
- Publication number
- ES2591156T3 ES2591156T3 ES11846398.3T ES11846398T ES2591156T3 ES 2591156 T3 ES2591156 T3 ES 2591156T3 ES 11846398 T ES11846398 T ES 11846398T ES 2591156 T3 ES2591156 T3 ES 2591156T3
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- Prior art keywords
- compound
- chlorophenyl
- chemical structure
- fluorophenyl
- alkyl
- Prior art date
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- -1 pyridonyl guanidine Chemical compound 0.000 title claims description 118
- 230000001225 therapeutic effect Effects 0.000 title description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title description 2
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 45
- 125000001424 substituent group Chemical group 0.000 claims abstract description 29
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 27
- 150000002367 halogens Chemical class 0.000 claims abstract description 27
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 125000004475 heteroaralkyl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 4
- 239000012453 solvate Substances 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 53
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 32
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 11
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 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 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
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- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
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- 125000001153 fluoro group Chemical group F* 0.000 claims 1
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- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000005549 heteroarylene group Chemical group 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 108
- 238000004128 high performance liquid chromatography Methods 0.000 description 56
- 238000000034 method Methods 0.000 description 46
- 239000003795 chemical substances by application Substances 0.000 description 31
- 230000014759 maintenance of location Effects 0.000 description 28
- 239000000203 mixture Substances 0.000 description 23
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000009472 formulation Methods 0.000 description 15
- 230000000694 effects Effects 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 9
- 201000010099 disease Diseases 0.000 description 7
- 238000002560 therapeutic procedure Methods 0.000 description 7
- 230000006907 apoptotic process Effects 0.000 description 6
- 125000002993 cycloalkylene group Chemical group 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
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- 238000003786 synthesis reaction Methods 0.000 description 5
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- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
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- 125000003636 chemical group Chemical group 0.000 description 4
- 238000011260 co-administration Methods 0.000 description 4
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- 150000002357 guanidines Chemical class 0.000 description 4
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
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- VTSFNCCQCOEPKF-UHFFFAOYSA-N 3-amino-1h-pyridin-2-one Chemical class NC1=CC=CN=C1O VTSFNCCQCOEPKF-UHFFFAOYSA-N 0.000 description 2
- 102100021870 ATP synthase subunit O, mitochondrial Human genes 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
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- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
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- 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
- A61P9/10—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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- 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
-
- 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
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- 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
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Rheumatology (AREA)
- Dermatology (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US42093410P | 2010-12-08 | 2010-12-08 | |
| US420934P | 2010-12-08 | ||
| PCT/US2011/063945 WO2012078869A1 (en) | 2010-12-08 | 2011-12-08 | Pyridonyl guanidine f1f0-atpase inhibitors and therapeutic uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2591156T3 true ES2591156T3 (es) | 2016-11-25 |
Family
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Family Applications (1)
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| ES11846398.3T Active ES2591156T3 (es) | 2010-12-08 | 2011-12-08 | Inhibidores de F1F0-ATPasas de tipo piridonil guanidina y sus usos terapéuticos |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US9000014B2 (OSRAM) |
| EP (1) | EP2648710B1 (OSRAM) |
| JP (1) | JP6050242B2 (OSRAM) |
| CN (1) | CN103458886B (OSRAM) |
| AU (1) | AU2011338304B2 (OSRAM) |
| CA (1) | CA2820044A1 (OSRAM) |
| ES (1) | ES2591156T3 (OSRAM) |
| IL (1) | IL226790A (OSRAM) |
| MX (1) | MX2013006398A (OSRAM) |
| WO (1) | WO2012078869A1 (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US9169199B2 (en) | 2010-12-08 | 2015-10-27 | Lycera Corporation | Cycloalkyl guanidine F1F0-ATPase inhibitors and therapeutic uses thereof |
| CA2820044A1 (en) | 2010-12-08 | 2012-06-14 | Lycera Corporation | Pyridonyl guanidine f1f0-atpase inhibitors and therapeutic uses thereof |
| HRP20171280T1 (hr) | 2010-12-08 | 2018-01-12 | Lycera Corporation | Pirazolilgvanidinski inhibitori f1f0-atpaze i njihova upotreba u terapiji |
| WO2013185045A1 (en) | 2012-06-08 | 2013-12-12 | Lycera Corporation | Indazole guanidine f1f0-atpase inhibitors and therapeutic uses thereof |
| US9580391B2 (en) | 2012-06-08 | 2017-02-28 | Lycera Corporation | Saturated acyl guanidine for inhibition of F1F0-ATPase |
| WO2013185048A2 (en) | 2012-06-08 | 2013-12-12 | Lycera Corporation | Heterocyclic guanidine f1f0-atpase inhibitors and therapeutic uses thereof |
| WO2015089152A1 (en) | 2013-12-10 | 2015-06-18 | Lycera Corporation | N-substituted pyrazolyl guanidine f1f0-atpase inhibitors and therapeutic uses thereof |
| CA2931851A1 (en) | 2013-12-10 | 2015-06-18 | Lycera Corporation | Trifluoromethyl pyrazolyl guanidine f1f0-atpase inhibitors and therapeutic uses thereof |
| JP2016539983A (ja) * | 2013-12-10 | 2016-12-22 | リセラ・コーポレイションLycera Corporation | アルキルピラゾリルグアニジンf1f0−atpアーゼ阻害剤及びその治療用途 |
| US9553382B2 (en) * | 2014-06-27 | 2017-01-24 | Xiaomi Inc. | Headphone socket assembly and electronic equipment including same |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4977189A (en) | 1986-05-07 | 1990-12-11 | American Cyanamid Company | Substituted guanidinedicarbonyl derivatives |
| JPH07188197A (ja) | 1993-11-17 | 1995-07-25 | Fujisawa Pharmaceut Co Ltd | オキサゾール誘導体 |
| DE4344550A1 (de) | 1993-12-24 | 1995-06-29 | Hoechst Ag | Substituierte 1-Oxo-1,2-dihydro-isochinolinoyl- und 1,1-Dioxo-2H-1,2-benzothiazinoylguanidine, Verfahrenzu ihrer Herstellung, ihre Verwendung als Medikamentt oder Diagnostikum sowie sie enthaltendes Medikamen |
| US7041702B1 (en) | 1997-10-21 | 2006-05-09 | Scion Pharmaceuticals, Inc. | Pharmaceutically active compounds and methods of use |
| JP2002536411A (ja) | 1999-02-09 | 2002-10-29 | ブリストル−マイヤーズ スクイブ カンパニー | Xa因子のラクタム系阻害剤および方法 |
| US7276348B2 (en) | 1999-04-30 | 2007-10-02 | Regents Of The University Of Michigan | Compositions and methods relating to F1F0-ATPase inhibitors and targets thereof |
| CN1202095C (zh) | 1999-07-15 | 2005-05-18 | 住友制药株式会社 | 杂芳环化合物 |
| US6627629B2 (en) | 2000-06-30 | 2003-09-30 | Bristol-Myers Squibb Pharma | N-ureidoheterocycloalkyl-piperidines as modulators of chemokine receptor activity |
| AU2002357137A1 (en) | 2001-12-10 | 2003-06-23 | Bristol-Myers Squibb Company | (1-phenyl-2-heteroaryl)ethyl-guanidine compounds as inhibitors of mitochondrial f1f0 atp hydrolase |
| GB0208224D0 (en) | 2002-04-10 | 2002-05-22 | Celltech R&D Ltd | Chemical compounds |
| US20040009972A1 (en) | 2002-06-17 | 2004-01-15 | Ding Charles Z. | Benzodiazepine inhibitors of mitochondial F1F0 ATP hydrolase and methods of inhibiting F1F0 ATP hydrolase |
| US7109224B2 (en) | 2002-11-06 | 2006-09-19 | Bristol-Myers Squibb Co. | Acyl guanidine compounds and use thereof |
| AU2003297629A1 (en) | 2002-12-04 | 2004-06-23 | Ore Pharmaceuticals Inc. | Modulators of melanocortin receptor |
| DE102004008141A1 (de) | 2004-02-19 | 2005-09-01 | Abbott Gmbh & Co. Kg | Guanidinverbindungen und ihre Verwendung als Bindungspartner für 5-HT5-Rezeptoren |
| US20090275099A1 (en) | 2004-04-27 | 2009-11-05 | Regents Of The University Of Michigan | Methods and compositions for treating diseases and conditions associated with mitochondrial function |
| US20050272723A1 (en) | 2004-04-27 | 2005-12-08 | The Regents Of The University Of Michigan | Methods and compositions for treating diseases and conditions associated with mitochondrial function |
| EP1765325A4 (en) | 2004-07-01 | 2009-08-12 | Synta Pharmaceuticals Corp | HETEROARYL COMPOUNDS SUBSTITUTED IN 2 |
| EP2418206A3 (en) | 2006-06-09 | 2012-06-27 | The Regents of the University of Michigan | Benzodiazepine derivatives useful in the treatment of autoimmune disorders |
| WO2009036175A2 (en) * | 2007-09-14 | 2009-03-19 | The Regents Of The University Of Michigan | F1f0-atpase inhibitors and related methods |
| JP2011507910A (ja) | 2007-12-21 | 2011-03-10 | ユニバーシティー オブ ロチェスター | 真核生物の寿命を変更するための方法 |
| KR100982661B1 (ko) | 2008-04-22 | 2010-09-17 | 전남대학교산학협력단 | 플라스멥신 ⅱ 활성을 저해하는 화합물을 유효성분으로함유하는 말라리아 예방 및 치료를 위한 약학 조성물 및이를 이용한 말라리아 치료방법 |
| US8497307B2 (en) | 2008-09-11 | 2013-07-30 | The Regents Of The University Of Michigan | Aryl guanidine F1F0-ATPase inhibitors and related methods |
| CA2820044A1 (en) | 2010-12-08 | 2012-06-14 | Lycera Corporation | Pyridonyl guanidine f1f0-atpase inhibitors and therapeutic uses thereof |
| HRP20171280T1 (hr) | 2010-12-08 | 2018-01-12 | Lycera Corporation | Pirazolilgvanidinski inhibitori f1f0-atpaze i njihova upotreba u terapiji |
| US9169199B2 (en) | 2010-12-08 | 2015-10-27 | Lycera Corporation | Cycloalkyl guanidine F1F0-ATPase inhibitors and therapeutic uses thereof |
| AU2011338302A1 (en) | 2010-12-08 | 2013-07-11 | Lycera Corporation | Cycloalkyl guanidine F1F0-ATPase inhibitors and therapeutic uses thereof |
| WO2013185048A2 (en) | 2012-06-08 | 2013-12-12 | Lycera Corporation | Heterocyclic guanidine f1f0-atpase inhibitors and therapeutic uses thereof |
| WO2013185045A1 (en) | 2012-06-08 | 2013-12-12 | Lycera Corporation | Indazole guanidine f1f0-atpase inhibitors and therapeutic uses thereof |
| US9580391B2 (en) | 2012-06-08 | 2017-02-28 | Lycera Corporation | Saturated acyl guanidine for inhibition of F1F0-ATPase |
| CA2931851A1 (en) | 2013-12-10 | 2015-06-18 | Lycera Corporation | Trifluoromethyl pyrazolyl guanidine f1f0-atpase inhibitors and therapeutic uses thereof |
-
2011
- 2011-12-08 CA CA2820044A patent/CA2820044A1/en not_active Abandoned
- 2011-12-08 WO PCT/US2011/063945 patent/WO2012078869A1/en not_active Ceased
- 2011-12-08 US US13/992,254 patent/US9000014B2/en not_active Expired - Fee Related
- 2011-12-08 CN CN201180065932.9A patent/CN103458886B/zh not_active Expired - Fee Related
- 2011-12-08 JP JP2013543340A patent/JP6050242B2/ja not_active Expired - Fee Related
- 2011-12-08 EP EP11846398.3A patent/EP2648710B1/en not_active Not-in-force
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2013
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2015
- 2015-04-01 US US14/675,832 patent/US9370507B2/en not_active Expired - Fee Related
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| EP2648710A1 (en) | 2013-10-16 |
| IL226790A (en) | 2017-05-29 |
| US20140051727A1 (en) | 2014-02-20 |
| EP2648710A4 (en) | 2014-04-02 |
| CA2820044A1 (en) | 2012-06-14 |
| JP6050242B2 (ja) | 2016-12-21 |
| WO2012078869A1 (en) | 2012-06-14 |
| AU2011338304B2 (en) | 2016-10-27 |
| JP2014505032A (ja) | 2014-02-27 |
| CN103458886B (zh) | 2016-06-08 |
| EP2648710B1 (en) | 2016-06-15 |
| US9000014B2 (en) | 2015-04-07 |
| MX2013006398A (es) | 2013-12-02 |
| US9370507B2 (en) | 2016-06-21 |
| US20150335625A1 (en) | 2015-11-26 |
| CN103458886A (zh) | 2013-12-18 |
| AU2011338304A1 (en) | 2013-07-11 |
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