NZ566022A - Caspase inhibitor prodrugs - Google Patents
Caspase inhibitor prodrugsInfo
- Publication number
- NZ566022A NZ566022A NZ566022A NZ56602206A NZ566022A NZ 566022 A NZ566022 A NZ 566022A NZ 566022 A NZ566022 A NZ 566022A NZ 56602206 A NZ56602206 A NZ 56602206A NZ 566022 A NZ566022 A NZ 566022A
- Authority
- NZ
- New Zealand
- Prior art keywords
- disease
- 6alkyl
- membered
- compound according
- ring
- Prior art date
Links
- 229940123169 Caspase inhibitor Drugs 0.000 title claims description 13
- 239000000651 prodrug Substances 0.000 title abstract description 18
- 229940002612 prodrug Drugs 0.000 title abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 42
- 201000010099 disease Diseases 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 33
- 102000011727 Caspases Human genes 0.000 claims abstract description 24
- 108010076667 Caspases Proteins 0.000 claims abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 8
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 5
- -1 2-t-butylphenyl Chemical group 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 125000004429 atom Chemical group 0.000 claims description 25
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000001931 aliphatic group Chemical group 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical group FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 230000006907 apoptotic process Effects 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 12
- 208000022993 cryopyrin-associated periodic syndrome Diseases 0.000 claims description 12
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- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 230000001404 mediated effect Effects 0.000 claims description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- 125000002619 bicyclic group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 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
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 8
- 101150041968 CDC13 gene Proteins 0.000 claims description 8
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
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- 230000003213 activating effect Effects 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
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- 238000005481 NMR spectroscopy Methods 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 5
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- 230000001154 acute effect Effects 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 230000009529 traumatic brain injury Effects 0.000 claims description 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 4
- 238000004293 19F NMR spectroscopy Methods 0.000 claims description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- 206010008909 Chronic Hepatitis Diseases 0.000 claims description 4
- 206010064568 Chronic infantile neurological cutaneous and articular syndrome Diseases 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 206010016207 Familial Mediterranean fever Diseases 0.000 claims description 4
- 208000035690 Familial cold urticaria Diseases 0.000 claims description 4
- 102000000589 Interleukin-1 Human genes 0.000 claims description 4
- 108010002352 Interleukin-1 Proteins 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 201000002795 Muckle-Wells syndrome Diseases 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 206010040047 Sepsis Diseases 0.000 claims description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 239000010836 blood and blood product Substances 0.000 claims description 4
- 229940125691 blood product Drugs 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 208000035196 congenital hypomyelinating 2 neuropathy Diseases 0.000 claims description 4
- 210000004351 coronary vessel Anatomy 0.000 claims description 4
- 235000005911 diet Nutrition 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 4
- 230000036303 septic shock Effects 0.000 claims description 4
- 239000003981 vehicle Substances 0.000 claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
- 201000004384 Alopecia Diseases 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
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- 206010055128 Autoimmune neutropenia Diseases 0.000 claims description 3
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- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 3
- 208000004429 Bacillary Dysentery Diseases 0.000 claims description 3
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- 206010068597 Bulbospinal muscular atrophy congenital Diseases 0.000 claims description 3
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000035473 Communicable disease Diseases 0.000 claims description 3
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- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims description 3
- 206010014596 Encephalitis Japanese B Diseases 0.000 claims description 3
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- 208000003807 Graves Disease Diseases 0.000 claims description 3
- 208000015023 Graves' disease Diseases 0.000 claims description 3
- 208000031886 HIV Infections Diseases 0.000 claims description 3
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- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims description 3
- 208000032456 Hemorrhagic Shock Diseases 0.000 claims description 3
- 208000005176 Hepatitis C Diseases 0.000 claims description 3
- 206010019773 Hepatitis G Diseases 0.000 claims description 3
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- 101000960954 Homo sapiens Interleukin-18 Proteins 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
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- 102100039898 Interleukin-18 Human genes 0.000 claims description 3
- 201000005807 Japanese encephalitis Diseases 0.000 claims description 3
- 241000710842 Japanese encephalitis virus Species 0.000 claims description 3
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- 206010027480 Metastatic malignant melanoma Diseases 0.000 claims description 3
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- 206010039710 Scleroderma Diseases 0.000 claims description 3
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- 206010042033 Stevens-Johnson syndrome Diseases 0.000 claims description 3
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 206010043781 Thyroiditis chronic Diseases 0.000 claims description 3
- 206010044223 Toxic epidermal necrolysis Diseases 0.000 claims description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 3
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
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- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 2
- ZCZVGQCBSJLDDS-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridine Chemical compound C1=CC=C2CCCNC2=N1 ZCZVGQCBSJLDDS-UHFFFAOYSA-N 0.000 claims description 2
- XEYKWYIXHMEQGM-UHFFFAOYSA-N 1,2-dihydro-1,8-naphthyridine Chemical compound C1=CC=C2C=CCNC2=N1 XEYKWYIXHMEQGM-UHFFFAOYSA-N 0.000 claims description 2
- UXJHQQLYKUVLIE-UHFFFAOYSA-N 1,2-dihydroacridine Chemical compound C1=CC=C2N=C(C=CCC3)C3=CC2=C1 UXJHQQLYKUVLIE-UHFFFAOYSA-N 0.000 claims description 2
- QRDNXAYNXUKMOO-UHFFFAOYSA-N 1,2-dihydrocinnoline Chemical compound C1=CC=C2C=CNNC2=C1 QRDNXAYNXUKMOO-UHFFFAOYSA-N 0.000 claims description 2
- ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 1,2-dihydrophenazine Chemical compound C1=CC=C2N=C(C=CCC3)C3=NC2=C1 ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 0.000 claims description 2
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 claims description 2
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
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- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 2
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- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 claims description 2
- YQQRKUQVFWYEPV-UHFFFAOYSA-N 5,6-dihydrophenanthridine Chemical compound C1=CC=C2CNC3=CC=CC=C3C2=C1 YQQRKUQVFWYEPV-UHFFFAOYSA-N 0.000 claims description 2
- LDBZRFQWKQUHFF-UHFFFAOYSA-N 5h-pyridazino[4,5-b]indole Chemical compound N1=NC=C2C3=CC=CC=C3NC2=C1 LDBZRFQWKQUHFF-UHFFFAOYSA-N 0.000 claims description 2
- JAALLZGVBSLANN-UHFFFAOYSA-N 5h-pyrido[3,4-b][1,4]benzothiazine Chemical compound N1=CC=C2NC3=CC=CC=C3SC2=C1 JAALLZGVBSLANN-UHFFFAOYSA-N 0.000 claims description 2
- PHHUQAFGPIDWPU-UHFFFAOYSA-N 5h-pyrrolo[3,2-c:4,5-c']dipyridine Chemical compound N1C2=CC=NC=C2C2=C1C=CN=C2 PHHUQAFGPIDWPU-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 2
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- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 2
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
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| EP3970698A4 (en) | 2019-05-31 | 2022-08-31 | LG Chem, Ltd. | INJECTABLE COMPOSITION WITH PRODRUG OF CASPASE INHIBITORS AND METHOD OF MANUFACTURE THEREOF |
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| EP0929311B8 (en) | 1996-09-12 | 2006-02-01 | Idun Pharmaceuticals, Inc. | INHIBITION OF APOPTOSIS USING INTERLEUKIN-1 beta-CONVERTING ENZYME (ICE)/CED-3 FAMILY INHIBITORS |
| NZ330451A (https=) | 1996-09-12 | 2000-01-28 | Idun Pharmaceuticals Inc | |
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-
2006
- 2006-07-20 KR KR1020087004718A patent/KR20080038369A/ko not_active Ceased
- 2006-07-20 CN CNA2006800345091A patent/CN101268084A/zh active Pending
- 2006-07-20 ZA ZA200801172A patent/ZA200801172B/xx unknown
- 2006-07-20 NZ NZ566022A patent/NZ566022A/en not_active IP Right Cessation
- 2006-07-20 WO PCT/US2006/028174 patent/WO2007015931A2/en not_active Ceased
- 2006-07-20 US US11/489,939 patent/US7879891B2/en not_active Expired - Fee Related
- 2006-07-20 RU RU2008107576/04A patent/RU2427582C2/ru not_active IP Right Cessation
- 2006-07-20 EP EP06787963A patent/EP1910379B1/en not_active Not-in-force
- 2006-07-20 AU AU2006276096A patent/AU2006276096A1/en not_active Abandoned
- 2006-07-20 AT AT06787963T patent/ATE529430T1/de not_active IP Right Cessation
- 2006-07-20 JP JP2008523976A patent/JP2009502922A/ja active Pending
- 2006-07-20 CA CA002616337A patent/CA2616337A1/en not_active Abandoned
-
2008
- 2008-01-24 IL IL188997A patent/IL188997A0/en not_active IP Right Cessation
- 2008-02-28 NO NO20081050A patent/NO20081050L/no not_active Application Discontinuation
-
2010
- 2010-12-17 US US12/971,649 patent/US8168798B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR20080038369A (ko) | 2008-05-06 |
| WO2007015931A3 (en) | 2007-06-07 |
| EP1910379A2 (en) | 2008-04-16 |
| US8168798B2 (en) | 2012-05-01 |
| CA2616337A1 (en) | 2007-02-08 |
| AU2006276096A1 (en) | 2007-02-08 |
| EP1910379B1 (en) | 2011-10-19 |
| US20110137037A1 (en) | 2011-06-09 |
| ATE529430T1 (de) | 2011-11-15 |
| US7879891B2 (en) | 2011-02-01 |
| US20070155718A1 (en) | 2007-07-05 |
| IL188997A0 (en) | 2008-08-07 |
| CN101268084A (zh) | 2008-09-17 |
| NO20081050L (no) | 2008-04-28 |
| RU2427582C2 (ru) | 2011-08-27 |
| RU2008107576A (ru) | 2009-09-10 |
| ZA200801172B (en) | 2009-04-29 |
| WO2007015931A2 (en) | 2007-02-08 |
| JP2009502922A (ja) | 2009-01-29 |
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| Date | Code | Title | Description |
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| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |