JP2010531854A5 - - Google Patents
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- JP2010531854A5 JP2010531854A5 JP2010513980A JP2010513980A JP2010531854A5 JP 2010531854 A5 JP2010531854 A5 JP 2010531854A5 JP 2010513980 A JP2010513980 A JP 2010513980A JP 2010513980 A JP2010513980 A JP 2010513980A JP 2010531854 A5 JP2010531854 A5 JP 2010531854A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- halo
- compound
- amino
- amyloid
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims description 148
- 125000005843 halogen group Chemical group 0.000 claims description 127
- 239000008194 pharmaceutical composition Substances 0.000 claims description 62
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims description 43
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims description 43
- 208000037259 Amyloid Plaque Diseases 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 38
- 241000124008 Mammalia Species 0.000 claims description 35
- 241001465754 Metazoa Species 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 201000010099 disease Diseases 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 210000004556 brain Anatomy 0.000 claims description 27
- 125000004122 cyclic group Chemical group 0.000 claims description 26
- 230000015572 biosynthetic process Effects 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 239000000544 cholinesterase inhibitor Substances 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 208000024827 Alzheimer disease Diseases 0.000 claims description 14
- 230000001149 cognitive effect Effects 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 206010027175 memory impairment Diseases 0.000 claims description 13
- 229940122041 Cholinesterase inhibitor Drugs 0.000 claims description 12
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 12
- 230000007087 memory ability Effects 0.000 claims description 12
- 208000010877 cognitive disease Diseases 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 9
- 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 9
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims description 8
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 230000003111 delayed effect Effects 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 6
- 229960003530 donepezil Drugs 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229960004136 rivastigmine Drugs 0.000 claims description 6
- 229960001685 tacrine Drugs 0.000 claims description 6
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims description 6
- 206010065040 AIDS dementia complex Diseases 0.000 claims description 5
- 230000007351 Aβ plaque formation Effects 0.000 claims description 5
- 206010007509 Cardiac amyloidosis Diseases 0.000 claims description 5
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims description 5
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims description 5
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims description 5
- 206010012289 Dementia Diseases 0.000 claims description 5
- 201000010374 Down Syndrome Diseases 0.000 claims description 5
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims description 5
- 241000282412 Homo Species 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 201000011523 endocrine gland cancer Diseases 0.000 claims description 5
- 201000010901 lateral sclerosis Diseases 0.000 claims description 5
- 208000002780 macular degeneration Diseases 0.000 claims description 5
- 208000005264 motor neuron disease Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 235000018102 proteins Nutrition 0.000 claims description 5
- 102000004169 proteins and genes Human genes 0.000 claims description 5
- 108090000623 proteins and genes Proteins 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- LZXHHNKULPHARO-UHFFFAOYSA-M (3,4-dichlorophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=C(Cl)C(Cl)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LZXHHNKULPHARO-UHFFFAOYSA-M 0.000 claims description 4
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Amino-1-propanesulfonic acid Natural products NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 claims description 4
- 208000002177 Cataract Diseases 0.000 claims description 4
- 206010061323 Optic neuropathy Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 230000006933 amyloid-beta aggregation Effects 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 229960003980 galantamine Drugs 0.000 claims description 4
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- -1 monosubstituted amino Chemical group 0.000 claims description 4
- 201000001119 neuropathy Diseases 0.000 claims description 4
- 230000007823 neuropathy Effects 0.000 claims description 4
- 208000020911 optic nerve disease Diseases 0.000 claims description 4
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 4
- 102000013498 tau Proteins Human genes 0.000 claims description 4
- 108010026424 tau Proteins Proteins 0.000 claims description 4
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims description 3
- 208000009829 Lewy Body Disease Diseases 0.000 claims description 3
- 201000002832 Lewy body dementia Diseases 0.000 claims description 3
- 206010002022 amyloidosis Diseases 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 2
- 208000018282 ACys amyloidosis Diseases 0.000 claims description 2
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 claims description 2
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 claims description 2
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims description 2
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 2
- 230000033616 DNA repair Effects 0.000 claims description 2
- 208000007487 Familial Cerebral Amyloid Angiopathy Diseases 0.000 claims description 2
- 235000008100 Ginkgo biloba Nutrition 0.000 claims description 2
- 244000194101 Ginkgo biloba Species 0.000 claims description 2
- 208000032849 Hereditary cerebral hemorrhage with amyloidosis Diseases 0.000 claims description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 2
- RDHQFKQIGNGIED-MRVPVSSYSA-N O-acetyl-L-carnitine Chemical compound CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C RDHQFKQIGNGIED-MRVPVSSYSA-N 0.000 claims description 2
- 206010048327 Supranuclear palsy Diseases 0.000 claims description 2
- 229930003779 Vitamin B12 Natural products 0.000 claims description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 2
- 229960004373 acetylcholine Drugs 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 239000000556 agonist Substances 0.000 claims description 2
- 230000001668 ameliorated effect Effects 0.000 claims description 2
- 230000002424 anti-apoptotic effect Effects 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
- 229960004372 aripiprazole Drugs 0.000 claims description 2
- 239000005667 attractant Substances 0.000 claims description 2
- 239000003693 atypical antipsychotic agent Substances 0.000 claims description 2
- 229940127236 atypical antipsychotics Drugs 0.000 claims description 2
- 239000002439 beta secretase inhibitor Substances 0.000 claims description 2
- 229940088623 biologically active substance Drugs 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000001413 cellular effect Effects 0.000 claims description 2
- 239000002738 chelating agent Substances 0.000 claims description 2
- 230000031902 chemoattractant activity Effects 0.000 claims description 2
- 229960001231 choline Drugs 0.000 claims description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 2
- 229960004170 clozapine Drugs 0.000 claims description 2
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims description 2
- AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 claims description 2
- 230000019771 cognition Effects 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 2
- 235000018417 cysteine Nutrition 0.000 claims description 2
- 230000008021 deposition Effects 0.000 claims description 2
- 235000015872 dietary supplement Nutrition 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000003540 gamma secretase inhibitor Substances 0.000 claims description 2
- JGPMMRGNQUBGND-UHFFFAOYSA-N idebenone Chemical compound COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O JGPMMRGNQUBGND-UHFFFAOYSA-N 0.000 claims description 2
- 229960004135 idebenone Drugs 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 235000010445 lecithin Nutrition 0.000 claims description 2
- 239000000787 lecithin Substances 0.000 claims description 2
- 210000004558 lewy body Anatomy 0.000 claims description 2
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000002858 neurotransmitter agent Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229960005017 olanzapine Drugs 0.000 claims description 2
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 230000036542 oxidative stress Effects 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 229940002612 prodrug Drugs 0.000 claims description 2
- MGNVWUDMMXZUDI-UHFFFAOYSA-N propane-1,3-disulfonic acid Chemical compound OS(=O)(=O)CCCS(O)(=O)=O MGNVWUDMMXZUDI-UHFFFAOYSA-N 0.000 claims description 2
- 229940043131 pyroglutamate Drugs 0.000 claims description 2
- 229960001534 risperidone Drugs 0.000 claims description 2
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 239000011715 vitamin B12 Substances 0.000 claims description 2
- 235000019163 vitamin B12 Nutrition 0.000 claims description 2
- 229960000607 ziprasidone Drugs 0.000 claims description 2
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07111491 | 2007-07-02 | ||
| PCT/EP2008/058527 WO2009004038A2 (en) | 2007-07-02 | 2008-07-02 | Therapeutic compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010531854A JP2010531854A (ja) | 2010-09-30 |
| JP2010531854A5 true JP2010531854A5 (https=) | 2010-11-11 |
Family
ID=40020257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010513980A Withdrawn JP2010531854A (ja) | 2007-07-02 | 2008-07-02 | 抗アミロイド剤としてのピレンゼピンおよびその誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20100247688A1 (https=) |
| EP (1) | EP2173355A2 (https=) |
| JP (1) | JP2010531854A (https=) |
| KR (1) | KR20100038424A (https=) |
| CN (1) | CN101778634A (https=) |
| AU (1) | AU2008270247A1 (https=) |
| BR (1) | BRPI0812849A2 (https=) |
| CA (1) | CA2691844A1 (https=) |
| IL (1) | IL202768A0 (https=) |
| MX (1) | MX2009014126A (https=) |
| NZ (1) | NZ582314A (https=) |
| RU (1) | RU2010103105A (https=) |
| WO (1) | WO2009004038A2 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010081825A2 (en) | 2009-01-13 | 2010-07-22 | Proteosys Ag | Pirenzepine as an agent in cancer treatment |
| EP2708540B1 (en) | 2011-05-10 | 2018-07-25 | Kyowa Hakko Kirin Co., Ltd. | Pyrimido-diazepinone compound |
| WO2013068592A1 (en) * | 2011-11-10 | 2013-05-16 | Fondation Jerome Lejeune | Inhibitors of cystathionine beta synthase to reduce the neurotoxic overproduction of endogenous hydrogen sulfide |
| CN116635034A (zh) * | 2020-09-22 | 2023-08-22 | K·E·克拉伦斯-史密斯 | 用于治疗人低胆碱能障碍的药物组合 |
| JP2023544224A (ja) * | 2020-09-22 | 2023-10-20 | キャスリーン、イー．クラレンス－スミス | ヒト低コリン作動性障害の処置のための医薬の組合せ |
| WO2023137098A1 (en) * | 2022-01-16 | 2023-07-20 | Winsantor, Inc. | Compositions and methods for improving sexual sensory disorders |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1795183B1 (de) * | 1968-08-20 | 1972-07-20 | Thomae Gmbh Dr K | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate und Arzneimittel |
| DE3818299A1 (de) * | 1988-05-30 | 1989-12-07 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE4112014A1 (de) * | 1991-04-12 | 1992-10-15 | Thomae Gmbh Dr K | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel zur behandlung von erkrankungen des zentralnervensystems und zur foerderung der cerebralen durchblutung |
| US8466144B2 (en) * | 2004-07-16 | 2013-06-18 | Proteosys Ag | Muscarinic antagonists with parp and sir modulating activity as cytoprotective agents |
| MX2008000461A (es) * | 2005-07-12 | 2008-03-10 | Abbott Gmbh & Co Kg | Compuestos de piridazina como inhibidores de la glucogeno sintasa cinasa 3. |
-
2008
- 2008-07-02 US US12/667,445 patent/US20100247688A1/en not_active Abandoned
- 2008-07-02 EP EP08774661A patent/EP2173355A2/en not_active Withdrawn
- 2008-07-02 JP JP2010513980A patent/JP2010531854A/ja not_active Withdrawn
- 2008-07-02 CA CA002691844A patent/CA2691844A1/en not_active Abandoned
- 2008-07-02 KR KR1020107002421A patent/KR20100038424A/ko not_active Withdrawn
- 2008-07-02 WO PCT/EP2008/058527 patent/WO2009004038A2/en not_active Ceased
- 2008-07-02 CN CN200880103247A patent/CN101778634A/zh active Pending
- 2008-07-02 AU AU2008270247A patent/AU2008270247A1/en not_active Abandoned
- 2008-07-02 NZ NZ582314A patent/NZ582314A/en not_active IP Right Cessation
- 2008-07-02 MX MX2009014126A patent/MX2009014126A/es not_active Application Discontinuation
- 2008-07-02 BR BRPI0812849-9A2A patent/BRPI0812849A2/pt not_active IP Right Cessation
- 2008-07-02 RU RU2010103105/15A patent/RU2010103105A/ru not_active Application Discontinuation
-
2009
- 2009-12-16 IL IL202768A patent/IL202768A0/en unknown
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