JP2014514288A5 - - Google Patents
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- Publication number
- JP2014514288A5 JP2014514288A5 JP2014501606A JP2014501606A JP2014514288A5 JP 2014514288 A5 JP2014514288 A5 JP 2014514288A5 JP 2014501606 A JP2014501606 A JP 2014501606A JP 2014501606 A JP2014501606 A JP 2014501606A JP 2014514288 A5 JP2014514288 A5 JP 2014514288A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- bisphosphonic acid
- alkyl
- acid derivative
- derivatives
- 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.)
- Granted
Links
- 239000002253 acid Substances 0.000 claims 15
- 230000001588 bifunctional effect Effects 0.000 claims 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 6
- 210000000988 bone and bone Anatomy 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 208000018084 Bone neoplasm Diseases 0.000 claims 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
- 239000003242 anti bacterial agent Substances 0.000 claims 4
- 208000024883 bone remodeling disease Diseases 0.000 claims 4
- 230000008482 dysregulation Effects 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- 230000004060 metabolic process Effects 0.000 claims 4
- 230000000010 osteolytic effect Effects 0.000 claims 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical group OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical group O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims 3
- 125000000524 functional group Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical group [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims 3
- 230000001225 therapeutic effect Effects 0.000 claims 3
- -1 (5-dimethylamino) naphthalene-1-sulfonyl Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 208000005243 Chondrosarcoma Diseases 0.000 claims 2
- 208000006168 Ewing Sarcoma Diseases 0.000 claims 2
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 2
- 208000007569 Giant Cell Tumors Diseases 0.000 claims 2
- 208000037147 Hypercalcaemia Diseases 0.000 claims 2
- 206010027476 Metastases Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 230000000118 anti-neoplastic effect Effects 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 claims 2
- 239000003246 corticosteroid Substances 0.000 claims 2
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical group O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 claims 2
- 229960002949 fluorouracil Drugs 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 230000000148 hypercalcaemia Effects 0.000 claims 2
- 208000030915 hypercalcemia disease Diseases 0.000 claims 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims 2
- 230000009401 metastasis Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 201000008968 osteosarcoma Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 150000003431 steroids Chemical class 0.000 claims 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical group [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- ACTOXUHEUCPTEW-BWHGAVFKSA-N 2-[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2s,5s,6r)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-o Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](O)[C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)[C@@H]1CC[C@H](N(C)C)[C@@H](C)O1 ACTOXUHEUCPTEW-BWHGAVFKSA-N 0.000 claims 1
- WCUXXCKIUMXCIB-UHFFFAOYSA-N 7-nitro-1,2,3-benzoxadiazole Chemical compound [O-][N+](=O)C1=CC=CC2=C1ON=N2 WCUXXCKIUMXCIB-UHFFFAOYSA-N 0.000 claims 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 1
- 108010092160 Dactinomycin Proteins 0.000 claims 1
- BVTJGGGYKAMDBN-UHFFFAOYSA-N Dioxetane Chemical class C1COO1 BVTJGGGYKAMDBN-UHFFFAOYSA-N 0.000 claims 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 1
- 239000004187 Spiramycin Substances 0.000 claims 1
- 101710183280 Topoisomerase Proteins 0.000 claims 1
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 claims 1
- 229930183665 actinomycin Natural products 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229940009456 adriamycin Drugs 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 230000003444 anaesthetic effect Effects 0.000 claims 1
- 229940035674 anesthetics Drugs 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 229960005149 bendazac Drugs 0.000 claims 1
- BYFMCKSPFYVMOU-UHFFFAOYSA-N bendazac Chemical compound C12=CC=CC=C2C(OCC(=O)O)=NN1CC1=CC=CC=C1 BYFMCKSPFYVMOU-UHFFFAOYSA-N 0.000 claims 1
- 229960005274 benzocaine Drugs 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 230000010072 bone remodeling Effects 0.000 claims 1
- 229960002092 busulfan Drugs 0.000 claims 1
- 229960004630 chlorambucil Drugs 0.000 claims 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- 229960001334 corticosteroids Drugs 0.000 claims 1
- 125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 claims 1
- 229960003957 dexamethasone Drugs 0.000 claims 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- 238000002059 diagnostic imaging Methods 0.000 claims 1
- 239000012502 diagnostic product Substances 0.000 claims 1
- 229960001259 diclofenac Drugs 0.000 claims 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims 1
- 229960003668 docetaxel Drugs 0.000 claims 1
- 229960004679 doxorubicin Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 claims 1
- 150000002159 estradiols Chemical class 0.000 claims 1
- 229960003399 estrone Drugs 0.000 claims 1
- 229960005293 etodolac Drugs 0.000 claims 1
- XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 claims 1
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims 1
- 229960005420 etoposide Drugs 0.000 claims 1
- 239000003193 general anesthetic agent Substances 0.000 claims 1
- 229960001680 ibuprofen Drugs 0.000 claims 1
- 229960001101 ifosfamide Drugs 0.000 claims 1
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims 1
- 125000000879 imine group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 229960000905 indomethacin Drugs 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 1
- 229960004768 irinotecan Drugs 0.000 claims 1
- 229960003768 lonazolac Drugs 0.000 claims 1
- XVUQHFRQHBLHQD-UHFFFAOYSA-N lonazolac Chemical compound OC(=O)CC1=CN(C=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1 XVUQHFRQHBLHQD-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 claims 1
- 229960001237 podophyllotoxin Drugs 0.000 claims 1
- YVCVYCSAAZQOJI-UHFFFAOYSA-N podophyllotoxin Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YVCVYCSAAZQOJI-UHFFFAOYSA-N 0.000 claims 1
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical group C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 229940043267 rhodamine b Drugs 0.000 claims 1
- 229960001294 spiramycin Drugs 0.000 claims 1
- 229930191512 spiramycin Natural products 0.000 claims 1
- 235000019372 spiramycin Nutrition 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 230000008685 targeting Effects 0.000 claims 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims 1
- 229960004528 vincristine Drugs 0.000 claims 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims 1
- 0 CC(N1CCN(C)CC1)=* Chemical compound CC(N1CCN(C)CC1)=* 0.000 description 4
- RXYPXQSKLGGKOL-UHFFFAOYSA-N CN1CCN(C)CC1 Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1152546A FR2973378B1 (fr) | 2011-03-28 | 2011-03-28 | Derives d'acide hydroxybisphosphonique bifonctionnels |
| FR1152546 | 2011-03-28 | ||
| PCT/EP2012/055569 WO2012130911A1 (fr) | 2011-03-28 | 2012-03-28 | Derives d'acide hydroxybisphosphonique bifonctionnels |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014514288A JP2014514288A (ja) | 2014-06-19 |
| JP2014514288A5 true JP2014514288A5 (https=) | 2015-05-14 |
| JP6026499B2 JP6026499B2 (ja) | 2016-11-16 |
Family
ID=45926557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014501606A Active JP6026499B2 (ja) | 2011-03-28 | 2012-03-28 | 二機能性ヒドロキシ−ビスホスホン酸誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9173946B2 (https=) |
| EP (1) | EP2691402B1 (https=) |
| JP (1) | JP6026499B2 (https=) |
| CA (1) | CA2831713C (https=) |
| ES (1) | ES2743276T3 (https=) |
| FR (1) | FR2973378B1 (https=) |
| WO (1) | WO2012130911A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3028762B1 (fr) | 2014-11-20 | 2017-01-06 | Atlanthera | Derives hydroxybisphosphoniques hydrosolubles de la doxorubicine |
| JP6209643B2 (ja) * | 2015-04-20 | 2017-10-04 | タイワン ホパックス ケミカルズ マニュファクチャリング カンパニー リミテッドＴａｉｗａｎ Ｈｏｐａｘ Ｃｈｅｍｓ．Ｍｆｇ．Ｃｏ．，Ｌｔｄ | 親骨性薬剤 |
| WO2020163637A1 (en) * | 2019-02-06 | 2020-08-13 | Oregon Health & Science University | Bisphosphonate-linked compounds |
| CN114585316A (zh) * | 2019-07-24 | 2022-06-03 | 布莱阿姆青年大学 | 骨结合化合物 |
| US11679099B2 (en) * | 2020-05-13 | 2023-06-20 | Seoul National University R&Db Foundation | Use of HIF-2α inhibitors for treating chondrosarcoma, or preventing recurrence and metastasis thereof |
| FR3122427B1 (fr) | 2021-04-30 | 2025-03-07 | Atlanthera | Derives hydroxybisphosphoniques de meloxicam pour traitement des maladies inflammatoires osteoarticulaires |
| CN118475661A (zh) * | 2021-12-10 | 2024-08-09 | Ppg工业俄亥俄公司 | 肼基甲酸酯官能化合物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2296080A1 (fr) | 1974-12-26 | 1976-07-23 | Yoshida Kogyo Kk | Bloc fenetre exterieur pourvu d'un appui de chassis fixe perfectionne |
| US4830847A (en) * | 1985-06-28 | 1989-05-16 | The Procter & Gamble Company | Diphosphonate-derivatized macromolecules |
| PH26923A (en) * | 1989-03-08 | 1992-12-03 | Ciba Geigy | N-substituted amino alkanediphosphonic acids |
| IT1303672B1 (it) * | 1998-07-28 | 2001-02-23 | Nicox Sa | Sali nitrati di farmaci attivi nei disordini ossei |
| WO2004089356A2 (en) * | 2003-04-03 | 2004-10-21 | Semafore Pharmaceuticals Inc. | Targeted bone marrow protection agents |
| US8404664B2 (en) * | 2005-08-11 | 2013-03-26 | Targanta Therapeutics, Inc. | Phosphonated Rifamycins and uses thereof for the prevention and treatment of bone and joint infections |
| US8133311B2 (en) * | 2007-04-30 | 2012-03-13 | Cabot Corporation | Pigment dipsersions comprising functionalized non-polymeric dispersants |
| FR2926080B1 (fr) * | 2008-01-03 | 2010-04-02 | Univ Nantes | Procede de synthese de derives d'acide hydroxy-bisphosphonique |
| FR2926081B1 (fr) | 2008-01-03 | 2010-02-19 | Univ Nantes | Derives d'acide hydroxy-bisphosphonique comme vecteur ciblant le tissu osseux |
| EP2289558A1 (en) * | 2009-08-25 | 2011-03-02 | KTB Tumorforschungsgesellschaft mbH | Bisphosphonate-prodrugs |
-
2011
- 2011-03-28 FR FR1152546A patent/FR2973378B1/fr not_active Expired - Fee Related
-
2012
- 2012-03-28 JP JP2014501606A patent/JP6026499B2/ja active Active
- 2012-03-28 WO PCT/EP2012/055569 patent/WO2012130911A1/fr not_active Ceased
- 2012-03-28 US US14/008,986 patent/US9173946B2/en active Active
- 2012-03-28 CA CA2831713A patent/CA2831713C/fr active Active
- 2012-03-28 ES ES12711632T patent/ES2743276T3/es active Active
- 2012-03-28 EP EP12711632.5A patent/EP2691402B1/fr active Active
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