CA2678895A1 - Tricyclic compounds useful in treating iron disorders - Google Patents
Tricyclic compounds useful in treating iron disorders Download PDFInfo
- Publication number
- CA2678895A1 CA2678895A1 CA002678895A CA2678895A CA2678895A1 CA 2678895 A1 CA2678895 A1 CA 2678895A1 CA 002678895 A CA002678895 A CA 002678895A CA 2678895 A CA2678895 A CA 2678895A CA 2678895 A1 CA2678895 A1 CA 2678895A1
- Authority
- CA
- Canada
- Prior art keywords
- optionally substituted
- independently
- alkyl
- hydrogen
- haloalkyl
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 394
- 208000016286 Iron metabolism disease Diseases 0.000 title claims abstract description 64
- 239000000203 mixture Substances 0.000 claims abstract description 115
- 238000000034 method Methods 0.000 claims abstract description 86
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 59
- 150000003839 salts Chemical class 0.000 claims abstract description 55
- 239000000651 prodrug Substances 0.000 claims abstract description 53
- 229940002612 prodrug Drugs 0.000 claims abstract description 53
- 239000012453 solvate Substances 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 384
- 239000001257 hydrogen Substances 0.000 claims description 325
- 229910052739 hydrogen Inorganic materials 0.000 claims description 325
- 150000002431 hydrogen Chemical class 0.000 claims description 253
- 125000001188 haloalkyl group Chemical group 0.000 claims description 231
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 164
- 125000001072 heteroaryl group Chemical group 0.000 claims description 155
- 125000003107 substituted aryl group Chemical group 0.000 claims description 141
- 125000002947 alkylene group Chemical group 0.000 claims description 109
- 125000000623 heterocyclic group Chemical group 0.000 claims description 103
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 93
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 92
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 92
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 87
- 125000003342 alkenyl group Chemical group 0.000 claims description 86
- 241000124008 Mammalia Species 0.000 claims description 72
- 125000000304 alkynyl group Chemical group 0.000 claims description 72
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 70
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 66
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 57
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 52
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 36
- 201000010099 disease Diseases 0.000 claims description 33
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 27
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 26
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 17
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 8
- JIJNVOLXPHRSIV-UHFFFAOYSA-N [1-(carbamimidoylsulfanylmethyl)-5,7-dihydrobenzo[d][2]benzothiepin-11-yl]methyl carbamimidothioate Chemical compound C1SCC2=CC=CC(CSC(N)=N)=C2C2=C1C=CC=C2CSC(=N)N JIJNVOLXPHRSIV-UHFFFAOYSA-N 0.000 claims description 2
- RICFBYYSLVWNTQ-UHFFFAOYSA-N [2,7-ditert-butyl-5-(carbamimidoylsulfanylmethyl)-9,9-dimethylxanthen-4-yl]methyl carbamimidothioate Chemical compound C1=C(C(C)(C)C)C=C2C(C)(C)C3=CC(C(C)(C)C)=CC(CSC(N)=N)=C3OC2=C1CSC(N)=N RICFBYYSLVWNTQ-UHFFFAOYSA-N 0.000 claims description 2
- WUNJWAUWEFKUHK-UHFFFAOYSA-N [2,8-dibromo-6-(carbamimidoylsulfanylmethyl)dibenzofuran-4-yl]methyl carbamimidothioate Chemical compound O1C2=C(CSC(N)=N)C=C(Br)C=C2C2=C1C(CSC(=N)N)=CC(Br)=C2 WUNJWAUWEFKUHK-UHFFFAOYSA-N 0.000 claims description 2
- SOHRRGPNXWNWFZ-UHFFFAOYSA-N [3,7-dibromo-6-(carbamimidoylsulfanylmethyl)dibenzofuran-4-yl]methyl carbamimidothioate Chemical compound O1C2=C(CSC(N)=N)C(Br)=CC=C2C2=C1C(CSC(=N)N)=C(Br)C=C2 SOHRRGPNXWNWFZ-UHFFFAOYSA-N 0.000 claims description 2
- LAYQGYPBCFKBJV-UHFFFAOYSA-N [3,7-dibromo-6-(carbamimidoylsulfanylmethyl)dibenzothiophen-4-yl]methyl carbamimidothioate Chemical compound S1C2=C(CSC(N)=N)C(Br)=CC=C2C2=C1C(CSC(=N)N)=C(Br)C=C2 LAYQGYPBCFKBJV-UHFFFAOYSA-N 0.000 claims description 2
- RYBBRMHNTXACFN-UHFFFAOYSA-N [4,5,8-tris(carbamimidoylsulfanylmethyl)biphenylen-1-yl]methyl carbamimidothioate Chemical compound NC(=N)SCC1=CC=C(CSC(N)=N)C2=C1C1=C2C(CSC(=N)N)=CC=C1CSC(N)=N RYBBRMHNTXACFN-UHFFFAOYSA-N 0.000 claims description 2
- WREKBBIJQCCCDC-UHFFFAOYSA-N [5-(carbamimidoylsulfanylmethyl)-9-methylacridin-4-yl]methyl carbamimidothioate Chemical compound C1=CC=C2C(C)=C(C=CC=C3CSC(N)=N)C3=NC2=C1CSC(N)=N WREKBBIJQCCCDC-UHFFFAOYSA-N 0.000 claims description 2
- FNXISSGFJKJMKY-UHFFFAOYSA-N [5-(carbamimidoylsulfanylmethyl)-9-oxofluoren-4-yl]methyl carbamimidothioate Chemical compound O=C1C2=CC=CC(CSC(N)=N)=C2C2=C1C=CC=C2CSC(=N)N FNXISSGFJKJMKY-UHFFFAOYSA-N 0.000 claims description 2
- ILIIONLTVRSKQT-UHFFFAOYSA-N [5-(carbamimidoylsulfanylmethyl)-9-oxoxanthen-4-yl]methyl carbamimidothioate Chemical compound O1C2=C(CSC(N)=N)C=CC=C2C(=O)C2=C1C(CSC(=N)N)=CC=C2 ILIIONLTVRSKQT-UHFFFAOYSA-N 0.000 claims description 2
- DXUPGDWGOABSDH-UHFFFAOYSA-N [5-(carbamimidoylsulfanylmethyl)acridin-4-yl]methyl carbamimidothioate Chemical compound C1=CC(CSC(N)=N)=C2N=C3C(CSC(=N)N)=CC=CC3=CC2=C1 DXUPGDWGOABSDH-UHFFFAOYSA-N 0.000 claims description 2
- VDJGOFWIPBEKBQ-UHFFFAOYSA-N [6-(carbamimidoylsulfanylmethyl)-3,7-dimethyldibenzofuran-4-yl]methyl carbamimidothioate Chemical compound CC1=CC=C2C3=CC=C(C)C(CSC(N)=N)=C3OC2=C1CSC(N)=N VDJGOFWIPBEKBQ-UHFFFAOYSA-N 0.000 claims description 2
- QBCGOAKVJHROLO-UHFFFAOYSA-N [6-(carbamimidoylsulfanylmethyl)-8-fluorodibenzofuran-4-yl]methyl carbamimidothioate Chemical compound O1C2=C(CSC(N)=N)C=C(F)C=C2C2=C1C(CSC(=N)N)=CC=C2 QBCGOAKVJHROLO-UHFFFAOYSA-N 0.000 claims description 2
- UDMAYDICQXOIIV-UHFFFAOYSA-N [6-(carbamimidoylsulfanylmethyl)-8-fluorodibenzothiophen-4-yl]methyl carbamimidothioate Chemical compound S1C2=C(CSC(N)=N)C=C(F)C=C2C2=C1C(CSC(=N)N)=CC=C2 UDMAYDICQXOIIV-UHFFFAOYSA-N 0.000 claims description 2
- TUFWDUKGFYLACL-UHFFFAOYSA-N [7-bromo-6-(carbamimidoylsulfanylmethyl)dibenzothiophen-4-yl]methyl carbamimidothioate Chemical compound S1C2=C(CSC(N)=N)C(Br)=CC=C2C2=C1C(CSC(=N)N)=CC=C2 TUFWDUKGFYLACL-UHFFFAOYSA-N 0.000 claims description 2
- DADBITCDAOYWIK-UHFFFAOYSA-N [8-(carbamimidoylsulfanylmethyl)-3,6-difluorobiphenylen-1-yl]methyl carbamimidothioate Chemical compound C12=CC(F)=CC(CSC(N)=N)=C2C2=C1C=C(F)C=C2CSC(=N)N DADBITCDAOYWIK-UHFFFAOYSA-N 0.000 claims description 2
- KZPZQJQJVUEFJN-UHFFFAOYSA-N [8-(carbamimidoylsulfanylmethyl)-9-oxofluoren-1-yl]methyl carbamimidothioate Chemical compound C12=CC=CC(CSC(N)=N)=C2C(=O)C2=C1C=CC=C2CSC(=N)N KZPZQJQJVUEFJN-UHFFFAOYSA-N 0.000 claims description 2
- PGLQOIXGWNOUFX-UHFFFAOYSA-N [8-(carbamimidoylsulfanylmethyl)anthracen-1-yl]methyl carbamimidothioate Chemical compound C1=CC(CSC(N)=N)=C2C=C3C(CSC(=N)N)=CC=CC3=CC2=C1 PGLQOIXGWNOUFX-UHFFFAOYSA-N 0.000 claims description 2
- AVVNVDBKYFRSIR-UHFFFAOYSA-N [8-(carbamimidoylsulfanylmethyl)biphenylen-1-yl]methyl carbamimidothioate Chemical compound C12=CC=CC(CSC(N)=N)=C2C2=C1C=CC=C2CSC(=N)N AVVNVDBKYFRSIR-UHFFFAOYSA-N 0.000 claims description 2
- DVMHUQSGVOMRKB-UHFFFAOYSA-N [9-(carbamimidoylsulfanylmethyl)dibenzothiophen-1-yl]methyl carbamimidothioate Chemical compound S1C2=CC=CC(CSC(N)=N)=C2C2=C1C=CC=C2CSC(=N)N DVMHUQSGVOMRKB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 70
- YKJYRKGMTKPKAH-UHFFFAOYSA-N [6-(carbamimidoylsulfanylmethyl)-8-chloro-2-fluorodibenzothiophen-4-yl]methyl carbamimidothioate Chemical compound C12=CC(Cl)=CC(CSC(N)=N)=C2SC2=C1C=C(F)C=C2CSC(=N)N YKJYRKGMTKPKAH-UHFFFAOYSA-N 0.000 claims 1
- YPBKXBQJGRXXJQ-UHFFFAOYSA-N [6-(carbamimidoylsulfanylmethyl)phenoxathiin-4-yl]methyl carbamimidothioate Chemical compound S1C2=CC=CC(CSC(N)=N)=C2OC2=C1C=CC=C2CSC(=N)N YPBKXBQJGRXXJQ-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 224
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- -1 -CN radical Chemical class 0.000 description 109
- 238000002360 preparation method Methods 0.000 description 106
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- 125000005843 halogen group Chemical group 0.000 description 62
- 238000005481 NMR spectroscopy Methods 0.000 description 58
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 48
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- 206010065973 Iron Overload Diseases 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- 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
- A61P7/06—Antianaemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/08—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing three- or four-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89358507P | 2007-03-07 | 2007-03-07 | |
| US60/893,585 | 2007-03-07 | ||
| PCT/US2008/056250 WO2008109840A1 (en) | 2007-03-07 | 2008-03-07 | Tricyclic compounds useful in treating iron disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2678895A1 true CA2678895A1 (en) | 2008-09-12 |
Family
ID=39512833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002678895A Abandoned CA2678895A1 (en) | 2007-03-07 | 2008-03-07 | Tricyclic compounds useful in treating iron disorders |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20090069408A1 (enExample) |
| EP (1) | EP2061755A1 (enExample) |
| JP (1) | JP2010520884A (enExample) |
| CN (1) | CN101616892A (enExample) |
| AR (1) | AR065628A1 (enExample) |
| AU (1) | AU2008222666A1 (enExample) |
| BR (1) | BRPI0808043A2 (enExample) |
| CA (1) | CA2678895A1 (enExample) |
| CL (1) | CL2008000666A1 (enExample) |
| MX (1) | MX2009009466A (enExample) |
| RU (1) | RU2009136996A (enExample) |
| TW (1) | TW200845961A (enExample) |
| WO (1) | WO2008109840A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2688547A1 (en) * | 2007-06-05 | 2008-12-11 | Xenon Pharmaceuticals, Inc. | Aromatic and heteroaromatic compounds useful in treating iron disorders |
| AR077892A1 (es) | 2009-08-20 | 2011-09-28 | Vifor Int Ag | Quinolinas antagonistas de la hepcidina |
| AR077958A1 (es) | 2009-08-27 | 2011-10-05 | Vifor Int Ag | Quinoxalinonas antagonistas de la hepcidina |
| AR077999A1 (es) | 2009-09-02 | 2011-10-05 | Vifor Int Ag | Antagonistas de pirimidin y triazin-hepcidina |
| TW201113274A (en) | 2009-09-07 | 2011-04-16 | Vifor Int Ag | Novel ethanediamine hepcidine antagonists |
| AR078278A1 (es) | 2009-09-09 | 2011-10-26 | Vifor Int Ag | Antagonistas de la tiazol y oxazol hepcidina, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de anemias y enfermedades asociadas a deficiencias de hierro. |
| US20120214803A1 (en) | 2011-02-18 | 2012-08-23 | Vifor (International) Ag | Novel Sulfonaminoquinoline Hepcidin Antagonists |
| JP6810988B2 (ja) | 2015-10-23 | 2021-01-13 | ヴィフォール （インターナショナル） アクチェンゲゼルシャフトＶｉｆｏｒ （Ｉｎｔｅｒｎａｔｉｏｎａｌ） ＡＧ | 新規なフェロポーチン阻害剤 |
| JOP20180036A1 (ar) | 2017-04-18 | 2019-01-30 | Vifor Int Ag | أملاح لمثبطات فروبورتين جديدة |
| TW202102478A (zh) | 2019-04-01 | 2021-01-16 | 瑞士商威佛（國際）股份有限公司 | 新穎的鐵螯合物 |
| CN114163417B (zh) * | 2021-12-06 | 2023-08-04 | 郑州海阔光电材料有限公司 | 一种3-溴硫芴的合成方法 |
| JP2023177660A (ja) * | 2022-06-02 | 2023-12-14 | 旭化成株式会社 | ルテニウム錯体の製造方法、並びにルテニウム錯体及びこれを用いたジアミンの製造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845770A (en) * | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US4326525A (en) * | 1980-10-14 | 1982-04-27 | Alza Corporation | Osmotic device that improves delivery properties of agent in situ |
| WO1994006802A1 (fr) * | 1992-09-18 | 1994-03-31 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose de thienodiazepine et son utilisation medicinale |
| US6310243B1 (en) * | 1994-09-23 | 2001-10-30 | Nycomed Imaging As | Iodinated x-ray contrast media |
| US6080587A (en) * | 1998-01-23 | 2000-06-27 | Eli Lilly And Company | Method for preparing and selecting pharmaceutically useful sulfur-bridged bi- and triaromatic ring compounds from a structurally diverse universal library |
| GB9815880D0 (en) * | 1998-07-21 | 1998-09-16 | Pfizer Ltd | Heterocycles |
| US20060269498A1 (en) * | 2005-05-17 | 2006-11-30 | Gerard Malle | Hair shaping composition comprising at least one polyguanidine other than hydroxide |
| CA2688547A1 (en) * | 2007-06-05 | 2008-12-11 | Xenon Pharmaceuticals, Inc. | Aromatic and heteroaromatic compounds useful in treating iron disorders |
-
2008
- 2008-03-06 CL CL200800666A patent/CL2008000666A1/es unknown
- 2008-03-06 AR ARP080100936A patent/AR065628A1/es not_active Application Discontinuation
- 2008-03-07 EP EP08754872A patent/EP2061755A1/en not_active Withdrawn
- 2008-03-07 CA CA002678895A patent/CA2678895A1/en not_active Abandoned
- 2008-03-07 JP JP2009552912A patent/JP2010520884A/ja not_active Withdrawn
- 2008-03-07 CN CN200880005559A patent/CN101616892A/zh active Pending
- 2008-03-07 TW TW097108246A patent/TW200845961A/zh unknown
- 2008-03-07 AU AU2008222666A patent/AU2008222666A1/en not_active Abandoned
- 2008-03-07 US US12/044,731 patent/US20090069408A1/en not_active Abandoned
- 2008-03-07 WO PCT/US2008/056250 patent/WO2008109840A1/en not_active Ceased
- 2008-03-07 BR BRPI0808043-7A2A patent/BRPI0808043A2/pt not_active IP Right Cessation
- 2008-03-07 MX MX2009009466A patent/MX2009009466A/es not_active Application Discontinuation
- 2008-03-07 RU RU2009136996/04A patent/RU2009136996A/ru not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR065628A1 (es) | 2009-06-17 |
| AU2008222666A1 (en) | 2008-09-12 |
| EP2061755A1 (en) | 2009-05-27 |
| JP2010520884A (ja) | 2010-06-17 |
| RU2009136996A (ru) | 2011-04-20 |
| WO2008109840A1 (en) | 2008-09-12 |
| CL2008000666A1 (es) | 2008-06-13 |
| BRPI0808043A2 (pt) | 2014-06-24 |
| US20090069408A1 (en) | 2009-03-12 |
| CN101616892A (zh) | 2009-12-30 |
| MX2009009466A (es) | 2009-09-15 |
| TW200845961A (en) | 2008-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20130307 |