CA2644380A1 - Benzimidazole derivatives - Google Patents
Benzimidazole derivatives Download PDFInfo
- Publication number
- CA2644380A1 CA2644380A1 CA002644380A CA2644380A CA2644380A1 CA 2644380 A1 CA2644380 A1 CA 2644380A1 CA 002644380 A CA002644380 A CA 002644380A CA 2644380 A CA2644380 A CA 2644380A CA 2644380 A1 CA2644380 A1 CA 2644380A1
- Authority
- CA
- Canada
- Prior art keywords
- methoxy
- formula
- compound
- ethyl
- phenyl
- 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
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 3
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- 229940002612 prodrug Drugs 0.000 claims abstract description 9
- 239000000651 prodrug Substances 0.000 claims abstract description 9
- -1 amino, carboxy Chemical group 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 108090000445 Parathyroid hormone Proteins 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 102000003982 Parathyroid hormone Human genes 0.000 claims description 17
- 239000000199 parathyroid hormone Substances 0.000 claims description 17
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 15
- 239000011575 calcium Substances 0.000 claims description 15
- 229910052791 calcium Inorganic materials 0.000 claims description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 15
- 229960001319 parathyroid hormone Drugs 0.000 claims description 15
- 210000000988 bone and bone Anatomy 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 12
- 230000011164 ossification Effects 0.000 claims description 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- XNEWILNREVDHDJ-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfonylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1S(C)(=O)=O XNEWILNREVDHDJ-UHFFFAOYSA-N 0.000 claims description 7
- 206010006956 Calcium deficiency Diseases 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
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- XJIQNOQRLZSHST-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfanylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1SC XJIQNOQRLZSHST-UHFFFAOYSA-N 0.000 claims description 6
- STKOFLRHQQCLDD-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfinylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1S(C)=O STKOFLRHQQCLDD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
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- 102000055006 Calcitonin Human genes 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims description 4
- 229960004015 calcitonin Drugs 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- HNXCBYBLDPXLMN-UHFFFAOYSA-N 4-bromo-7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfanylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(Br)C=1CC1=CC=CN=C1SC HNXCBYBLDPXLMN-UHFFFAOYSA-N 0.000 claims description 3
- ZJKMBBWISFOMSY-UHFFFAOYSA-N 4-bromo-7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfinylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(Br)C=1CC1=CC=CN=C1S(C)=O ZJKMBBWISFOMSY-UHFFFAOYSA-N 0.000 claims description 3
- MXMSONJMVWOEPO-UHFFFAOYSA-N 5-[(2-ethoxypyridin-3-yl)methyl]-7-methoxy-1-(2-methoxyethyl)-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound CCOC1=NC=CC=C1CC1=CC(OC)=C(N(CCOC)C(=N2)C=3C=CC(=CC=3)C(C)C)C2=C1C(F)(F)F MXMSONJMVWOEPO-UHFFFAOYSA-N 0.000 claims description 3
- GXMQKRXNPGPMHC-UHFFFAOYSA-N 7-methoxy-5-[[2-(2-methoxyethoxy)pyridin-3-yl]methyl]-1-(2-methoxyethyl)-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound COCCOC1=NC=CC=C1CC1=CC(OC)=C(N(CCOC)C(=N2)C=3C=CC(=CC=3)C(C)C)C2=C1C(F)(F)F GXMQKRXNPGPMHC-UHFFFAOYSA-N 0.000 claims description 3
- 229940122361 Bisphosphonate Drugs 0.000 claims description 3
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 3
- 229940122156 Cathepsin K inhibitor Drugs 0.000 claims description 3
- 229930003316 Vitamin D Natural products 0.000 claims description 3
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 150000004663 bisphosphonates Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 239000003270 steroid hormone Substances 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 235000019166 vitamin D Nutrition 0.000 claims description 3
- 239000011710 vitamin D Substances 0.000 claims description 3
- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 3
- 229940046008 vitamin d Drugs 0.000 claims description 3
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- YZRCEDKJCYMCGB-UHFFFAOYSA-N 2-[3-[[7-methoxy-1-(2-methoxyethyl)-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazol-5-yl]methyl]pyridin-2-yl]oxy-n,n-dimethylethanamine Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1OCCN(C)C YZRCEDKJCYMCGB-UHFFFAOYSA-N 0.000 claims description 2
- WOFFMODEYRHQGY-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-2-(4-propan-2-ylphenyl)-5-[(2-prop-2-ynoxypyridin-3-yl)methyl]-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1OCC#C WOFFMODEYRHQGY-UHFFFAOYSA-N 0.000 claims description 2
- NIQSGWJDOXIURI-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-methoxypyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1OC NIQSGWJDOXIURI-UHFFFAOYSA-N 0.000 claims description 2
- MFUFZKHPBQXMBL-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-propan-2-yloxypyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1OC(C)C MFUFZKHPBQXMBL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
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- 125000001475 halogen functional group Chemical group 0.000 claims 4
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- 102100036893 Parathyroid hormone Human genes 0.000 claims 3
- 208000001132 Osteoporosis Diseases 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
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- JLTPTSWOAQALBQ-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfanylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=CC=1CC1=CC=CN=C1SC JLTPTSWOAQALBQ-UHFFFAOYSA-N 0.000 description 3
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- RWCZNOSAMSSDCI-UHFFFAOYSA-N [7-methoxy-1-(2-methoxyethyl)-2-(4-propan-2-ylphenyl)benzimidazol-5-yl]-(2-methylsulfanylpyridin-3-yl)methanol Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=CC=1C(O)C1=CC=CN=C1SC RWCZNOSAMSSDCI-UHFFFAOYSA-N 0.000 description 2
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- OGBMKVWORPGQRR-UMXFMPSGSA-N teriparatide Chemical compound C([C@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H](N)CO)C(C)C)[C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CNC=N1 OGBMKVWORPGQRR-UMXFMPSGSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 229960001023 tibolone Drugs 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
- 229960004276 zoledronic acid Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
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- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
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- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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- Psychology (AREA)
- Hospice & Palliative Care (AREA)
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- Urology & Nephrology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0606426.5A GB0606426D0 (en) | 2006-03-30 | 2006-03-30 | Benzimidazole derivatives |
| GB0606426.5 | 2006-03-30 | ||
| PCT/EP2007/002763 WO2007112913A2 (en) | 2006-03-30 | 2007-03-28 | Benzimidazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2644380A1 true CA2644380A1 (en) | 2007-10-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002644380A Abandoned CA2644380A1 (en) | 2006-03-30 | 2007-03-28 | Benzimidazole derivatives |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US20100227889A1 (enExample) |
| EP (1) | EP2004629A2 (enExample) |
| JP (1) | JP2009531363A (enExample) |
| KR (1) | KR20080110769A (enExample) |
| CN (1) | CN101400669A (enExample) |
| AR (1) | AR060334A1 (enExample) |
| AU (1) | AU2007234021B2 (enExample) |
| BR (1) | BRPI0710180A2 (enExample) |
| CA (1) | CA2644380A1 (enExample) |
| CL (1) | CL2007000850A1 (enExample) |
| CR (1) | CR10199A (enExample) |
| EC (1) | ECSP088781A (enExample) |
| GB (1) | GB0606426D0 (enExample) |
| GT (1) | GT200800200A (enExample) |
| IL (1) | IL193475A0 (enExample) |
| MA (1) | MA30341B1 (enExample) |
| MX (1) | MX2008012403A (enExample) |
| NO (1) | NO20084543L (enExample) |
| PE (1) | PE20071149A1 (enExample) |
| RU (1) | RU2008142831A (enExample) |
| TN (1) | TNSN08369A1 (enExample) |
| TW (1) | TW200806647A (enExample) |
| WO (1) | WO2007112913A2 (enExample) |
| ZA (1) | ZA200806833B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1993559T1 (sl) | 2006-02-03 | 2017-01-31 | Opko Renal, Llc | Zdravljenje nezadostnosti in pomanjkanja vitamina D s 25-hidroksivitaminon D2 in 25-hidroksivitaminom D3 |
| PT2679228T (pt) | 2006-06-21 | 2018-04-16 | Opko Ireland Global Holdings Ltd | Terapia utilizando um agente de repleção de vitamina d e um agente de substituição hormonal de vitamina d |
| CN104257667B (zh) | 2007-04-25 | 2019-06-04 | 欧普科Ip 控股Ii 有限公司 | 治疗维生素d不足和缺乏、继发性甲状旁腺功能亢进症和维生素d-响应疾病的方法和组合物 |
| KR101959952B1 (ko) | 2007-04-25 | 2019-03-19 | 사이토크로마 인코포레이티드 | 비타민 ｄ 화합물과 밀랍성 담체를 포함하는 경구 조절성 방출 조성물 |
| ES2783980T3 (es) | 2010-03-29 | 2020-09-21 | Opko Ireland Global Holdings Ltd | Métodos y composiciones para la reducción de niveles de paratiroides |
| EP2643298A1 (en) * | 2010-11-26 | 2013-10-02 | Leo Pharma A/S | Substituted cyclopentyl - azines as casr- active compounds |
| KR101847947B1 (ko) | 2013-03-15 | 2018-05-28 | 옵코 아이피 홀딩스 Ⅱ 인코포레이티드 | 안정화되고 변형된 비타민 ｄ 방출 제형 |
| US10220047B2 (en) | 2014-08-07 | 2019-03-05 | Opko Ireland Global Holdings, Ltd. | Adjunctive therapy with 25-hydroxyvitamin D and articles therefor |
| MY198547A (en) | 2016-03-28 | 2023-09-04 | Opko Ireland Global Holdings Ltd | Methods of vitamin d treatment |
Family Cites Families (5)
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| JP2000026430A (ja) * | 1998-07-02 | 2000-01-25 | Taisho Pharmaceut Co Ltd | ２、５、６−置換ベンズイミダゾール化合物誘導体 |
| US6362202B1 (en) * | 1999-03-02 | 2002-03-26 | Sepracor Inc. | Methods and compositions using (−) norcisapride in combination with proton pump inhibitors or H2 receptor antagonists |
| WO2004041277A1 (en) * | 2002-11-01 | 2004-05-21 | Merck & Co., Inc. | Carbonylamino-benzimidazole derivatives as androgen receptor modulators |
| GB0400781D0 (en) * | 2004-01-14 | 2004-02-18 | Novartis Ag | Organic compounds |
| EP1964548A1 (en) * | 2007-03-02 | 2008-09-03 | Novartis AG | Pharmaceutical compositions comprising a calcilytic agent |
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2006
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2007
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- 2007-03-28 AR ARP070101297A patent/AR060334A1/es not_active Application Discontinuation
- 2007-03-28 JP JP2009501943A patent/JP2009531363A/ja not_active Withdrawn
- 2007-03-28 BR BRPI0710180-5A patent/BRPI0710180A2/pt not_active IP Right Cessation
- 2007-03-28 EP EP07723708A patent/EP2004629A2/en not_active Withdrawn
- 2007-03-28 WO PCT/EP2007/002763 patent/WO2007112913A2/en not_active Ceased
- 2007-03-28 PE PE2007000352A patent/PE20071149A1/es not_active Application Discontinuation
- 2007-03-28 RU RU2008142831/04A patent/RU2008142831A/ru not_active Application Discontinuation
- 2007-03-28 CN CNA2007800087520A patent/CN101400669A/zh active Pending
- 2007-03-28 MX MX2008012403A patent/MX2008012403A/es not_active Application Discontinuation
- 2007-03-28 AU AU2007234021A patent/AU2007234021B2/en not_active Ceased
- 2007-03-28 CA CA002644380A patent/CA2644380A1/en not_active Abandoned
- 2007-03-28 US US12/295,381 patent/US20100227889A1/en not_active Abandoned
- 2007-03-29 CL CL200700850A patent/CL2007000850A1/es unknown
- 2007-03-29 TW TW096111055A patent/TW200806647A/zh unknown
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2008
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- 2008-08-14 IL IL193475A patent/IL193475A0/en unknown
- 2008-09-22 TN TNP2008000369A patent/TNSN08369A1/en unknown
- 2008-09-29 GT GT200800200A patent/GT200800200A/es unknown
- 2008-09-30 EC EC2008008781A patent/ECSP088781A/es unknown
- 2008-10-17 MA MA31302A patent/MA30341B1/fr unknown
- 2008-10-28 NO NO20084543A patent/NO20084543L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007234021A1 (en) | 2007-10-11 |
| WO2007112913A3 (en) | 2007-12-21 |
| TNSN08369A1 (en) | 2009-12-29 |
| WO2007112913A2 (en) | 2007-10-11 |
| US20100227889A1 (en) | 2010-09-09 |
| IL193475A0 (en) | 2009-05-04 |
| JP2009531363A (ja) | 2009-09-03 |
| AU2007234021B2 (en) | 2011-04-28 |
| TW200806647A (en) | 2008-02-01 |
| GT200800200A (es) | 2008-11-10 |
| BRPI0710180A2 (pt) | 2011-08-09 |
| CN101400669A (zh) | 2009-04-01 |
| PE20071149A1 (es) | 2007-12-04 |
| CR10199A (es) | 2008-10-16 |
| GB0606426D0 (en) | 2006-05-10 |
| MA30341B1 (fr) | 2009-04-01 |
| KR20080110769A (ko) | 2008-12-19 |
| AR060334A1 (es) | 2008-06-11 |
| CL2007000850A1 (es) | 2008-03-14 |
| NO20084543L (no) | 2008-10-21 |
| RU2008142831A (ru) | 2010-05-10 |
| MX2008012403A (es) | 2008-10-07 |
| ECSP088781A (es) | 2008-10-31 |
| ZA200806833B (en) | 2009-05-27 |
| EP2004629A2 (en) | 2008-12-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20130328 |