CA2609161A1 - Peptidomimetics selective for the somatostatin receptor subtypes 1 and/or 4 - Google Patents
Peptidomimetics selective for the somatostatin receptor subtypes 1 and/or 4 Download PDFInfo
- Publication number
- CA2609161A1 CA2609161A1 CA002609161A CA2609161A CA2609161A1 CA 2609161 A1 CA2609161 A1 CA 2609161A1 CA 002609161 A CA002609161 A CA 002609161A CA 2609161 A CA2609161 A CA 2609161A CA 2609161 A1 CA2609161 A1 CA 2609161A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- amide
- mmol
- compound
- sulfonic acid
- 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
- 108050001286 Somatostatin Receptor Proteins 0.000 title claims abstract description 29
- 102000011096 Somatostatin receptor Human genes 0.000 title claims abstract description 29
- 239000000816 peptidomimetic Substances 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 203
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
- 239000000556 agonist Substances 0.000 claims abstract description 16
- 201000010099 disease Diseases 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 12
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 239000005557 antagonist Substances 0.000 claims abstract description 9
- 150000001408 amides Chemical class 0.000 claims description 93
- -1 [1-(2-aminoethyl)-3-phenylpropyl]amide (S)-4-methylnaphthalene-1-sulfonic acid [1-(benzylamino-methyl)-2-(1H-imidazol-4-yl)ethyl]amide Chemical compound 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 30
- 235000013350 formula milk Nutrition 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 27
- 101100210114 Schizosaccharomyces pombe (strain 972 / ATCC 24843) sst4 gene Proteins 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
- 206010028980 Neoplasm Diseases 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- ZTDJDNLZVGJTBW-UHFFFAOYSA-N 4-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(C)=CC=C(S(O)(=O)=O)C2=C1 ZTDJDNLZVGJTBW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003601 C2-C6 alkynyl 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
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- 108010064556 somatostatin receptor subtype-4 Proteins 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
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- GRBFFMVWRPNJCA-IBGZPJMESA-N 2-[(3s)-3-[(4-methylnaphthalen-1-yl)sulfonylamino]-4-phenylmethoxybutyl]guanidine Chemical compound C([C@H](CCNC(N)=N)NS(=O)(=O)C1=CC=C(C2=CC=CC=C21)C)OCC1=CC=CC=C1 GRBFFMVWRPNJCA-IBGZPJMESA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004122 cyclic group Chemical group 0.000 claims description 4
- DCBQJALGXDLFFB-SFHVURJKSA-N n-[(2s)-5-amino-1-phenoxypentan-2-yl]-4-methylnaphthalene-1-sulfonamide Chemical compound C([C@H](CCCN)NS(=O)(=O)C1=CC=C(C2=CC=CC=C21)C)OC1=CC=CC=C1 DCBQJALGXDLFFB-SFHVURJKSA-N 0.000 claims description 4
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- CWYDORUNMQIIGU-NRFANRHFSA-N 2-[(3s)-3-[(2,3,4,5,6-pentamethylphenyl)sulfonylamino]-4-phenylmethoxybutyl]guanidine Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1S(=O)(=O)N[C@@H](CCNC(N)=N)COCC1=CC=CC=C1 CWYDORUNMQIIGU-NRFANRHFSA-N 0.000 claims description 3
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- 229920000136 polysorbate Polymers 0.000 claims description 3
- YZUWBOFAYRHWCT-ZZDYIDRTSA-N 4-methyl-n-[(2s)-5-(propan-2-ylamino)-1-(1,2,3,4-tetrahydronaphthalen-1-ylamino)pentan-2-yl]naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)N[C@H](CNC3C4=CC=CC=C4CCC3)CCCNC(C)C)=CC=C(C)C2=C1 YZUWBOFAYRHWCT-ZZDYIDRTSA-N 0.000 claims description 2
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- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 28
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 9
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- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 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 3
- ZVUAHOOPXNCFJG-NRFANRHFSA-N 4-methyl-n-[(2s)-1-phenoxy-5-(propan-2-ylamino)pentan-2-yl]naphthalene-1-sulfonamide Chemical compound C([C@H](CCCNC(C)C)NS(=O)(=O)C=1C2=CC=CC=C2C(C)=CC=1)OC1=CC=CC=C1 ZVUAHOOPXNCFJG-NRFANRHFSA-N 0.000 claims 2
- JHTOXGALCMEOLI-QFIPXVFZSA-N n-[(2s)-1-[2-(dimethylamino)ethylamino]-3-phenylmethoxypropan-2-yl]-4-methylnaphthalene-1-sulfonamide Chemical compound C([C@H](CNCCN(C)C)NS(=O)(=O)C=1C2=CC=CC=C2C(C)=CC=1)OCC1=CC=CC=C1 JHTOXGALCMEOLI-QFIPXVFZSA-N 0.000 claims 2
- FKQBPRCYJZWYDB-NRFANRHFSA-N n-[(2s)-4-(4,5-dihydro-1h-imidazol-2-ylamino)-1-phenylmethoxybutan-2-yl]-4-methylnaphthalene-1-sulfonamide Chemical compound C([C@H](NS(=O)(=O)C1=CC=C(C2=CC=CC=C21)C)COCC=1C=CC=CC=1)CNC1=NCCN1 FKQBPRCYJZWYDB-NRFANRHFSA-N 0.000 claims 2
- KFLMLKMNJWYXOC-FQEVSTJZSA-N n-[(2s)-5-amino-1-benzylsulfanylpentan-2-yl]-4-methylnaphthalene-1-sulfonamide Chemical compound C([C@H](CCCN)NS(=O)(=O)C1=CC=C(C2=CC=CC=C21)C)SCC1=CC=CC=C1 KFLMLKMNJWYXOC-FQEVSTJZSA-N 0.000 claims 2
- XYXBCEXCPBFYHC-UHFFFAOYSA-N n-[2-(benzylamino)-1-piperidin-4-ylethyl]-4-methylnaphthalene-1-sulfonamide Chemical compound C12=CC=CC=C2C(C)=CC=C1S(=O)(=O)NC(C1CCNCC1)CNCC1=CC=CC=C1 XYXBCEXCPBFYHC-UHFFFAOYSA-N 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- SUZMIWGZIWZKCQ-OAQYLSRUSA-N (2r)-n-(2-aminoethyl)-2-[(4-methylnaphthalen-1-yl)sulfonylamino]-3-phenylmethoxypropanamide Chemical compound C([C@@H](NS(=O)(=O)C1=CC=C(C2=CC=CC=C21)C)C(=O)NCCN)OCC1=CC=CC=C1 SUZMIWGZIWZKCQ-OAQYLSRUSA-N 0.000 claims 1
- VQVVZIHQYDLEDJ-OAQYLSRUSA-N (2s)-n-(2-aminoethyl)-3-benzylsulfanyl-2-[(4-methylnaphthalen-1-yl)sulfonylamino]propanamide Chemical compound C([C@@H](NS(=O)(=O)C1=CC=C(C2=CC=CC=C21)C)C(=O)NCCN)SCC1=CC=CC=C1 VQVVZIHQYDLEDJ-OAQYLSRUSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/49—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to sulfur atoms
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- A—HUMAN NECESSITIES
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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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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- A—HUMAN NECESSITIES
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68202005P | 2005-05-18 | 2005-05-18 | |
| US60/682,020 | 2005-05-18 | ||
| FI20055235 | 2005-05-18 | ||
| FI20055235A FI20055235A0 (fi) | 2005-05-18 | 2005-05-18 | Somatostatiinireseptorialatyyppeihin 1 ja/tai 4 selektiivisesti vaikuttavat peptidienkaltaiset yhdisteet |
| PCT/FI2006/050197 WO2006123020A1 (en) | 2005-05-18 | 2006-05-16 | Peptidomimetics selective for the somatostatin receptor subtypes 1 and/or 4 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2609161A1 true CA2609161A1 (en) | 2006-11-23 |
Family
ID=37430963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002609161A Abandoned CA2609161A1 (en) | 2005-05-18 | 2006-05-16 | Peptidomimetics selective for the somatostatin receptor subtypes 1 and/or 4 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20100048549A1 (enExample) |
| EP (1) | EP1885693A4 (enExample) |
| JP (1) | JP2008540618A (enExample) |
| CA (1) | CA2609161A1 (enExample) |
| WO (1) | WO2006123020A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| US8829041B2 (en) | 2006-06-23 | 2014-09-09 | Abbvie Inc. | Cyclopropyl amine derivatives |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| WO2012037258A1 (en) | 2010-09-16 | 2012-03-22 | Abbott Laboratories | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| JP2018538364A (ja) | 2015-11-04 | 2018-12-27 | ユニバーシティー オブ フロリダ リサーチ ファンデーション, インク. | ポリアミンスルホンアミドおよびこれらの使用 |
| CN114949174B (zh) * | 2022-07-19 | 2025-09-30 | 山东大学齐鲁医院 | Cst-14在制备糖尿病皮肤溃疡、破损治疗药物中的应用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4485101A (en) * | 1983-10-11 | 1984-11-27 | Administrators Of The Tulane Educational Fund | Peptides |
| US5409894A (en) * | 1991-03-14 | 1995-04-25 | Sandoz Ltd. | Method of preventing balloon catheterization blood vessel damage |
| JPH069402A (ja) * | 1991-05-15 | 1994-01-18 | Hiroyoshi Hidaka | 抗潰瘍剤 |
| FR2689130B1 (fr) * | 1992-03-30 | 1994-05-27 | Synthelabo | Derives de 1-[2 (arylsulfonylamino)ethyl-1-oxo] piperidine, leur preparation et leur application en therapeutique. |
| US5248673A (en) * | 1992-12-23 | 1993-09-28 | Bristol-Myers Squibb Co. | Bisamidine derivatives as thrombin inhibitors |
| KR0173034B1 (ko) * | 1995-04-28 | 1999-03-30 | 성재갑 | 선택적 트롬빈 억제제 |
| WO1997029097A1 (en) * | 1996-02-09 | 1997-08-14 | Smithkline Beecham Plc | Sulfonamide derivatives as 5ht7 receptor antagonists |
| ATE309993T1 (de) * | 1997-04-21 | 2005-12-15 | Takeda Pharmaceutical | 4,1-benzoxazepine, ihre analoga, und ihre verwendung als somatostatin-agonisten |
| GB9711043D0 (en) * | 1997-05-29 | 1997-07-23 | Ciba Geigy Ag | Organic compounds |
| US6124256A (en) * | 1998-03-27 | 2000-09-26 | Haeyry; Pekka | Method for the prevention of a patient's fibroproliferative vasculopathy |
| CA2327695A1 (en) * | 1998-04-08 | 1999-10-21 | Takeda Chemical Industries, Ltd. | Amine compounds, their production and their use as somatostatin receptor antagonists or agonists |
| FR2800735B1 (fr) * | 1999-11-09 | 2002-02-01 | Centre Nat Rech Scient | Nouvelles aralkyle-1,2-diamines possedant une activite calcimimetique et leur mode de preparation |
| GB0013060D0 (en) * | 2000-05-31 | 2000-07-19 | Astrazeneca Ab | Chemical compounds |
| PL374971A1 (en) * | 2002-08-09 | 2005-11-14 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds and methods to modulate coagulation |
| GB0314476D0 (en) * | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Compounds |
| WO2005033068A1 (en) * | 2003-10-06 | 2005-04-14 | Oy Juvantia Pharma Ltd | Somatostatin receptor 1 and/or 4 selective agonists and antagonists |
| FI20031454A0 (fi) * | 2003-10-06 | 2003-10-06 | Juvantia Pharma Ltd Oy | Selektiivisiä somatostatiinireseptori 1 ja/tai 4 -agonisteja ja -antagonisteja |
| FI20031455A0 (fi) * | 2003-10-06 | 2003-10-06 | Juvantia Pharma Ltd Oy | Sulfonyyliamino-peptidomimeettejä, jotka ovat aktiivisia somatostatiinireseptorialatyyppien 4 (SSTR4) ja 1 (SSTR1) suhteen |
| JP4521531B2 (ja) * | 2004-07-01 | 2010-08-11 | 財団法人名古屋産業科学研究所 | 不斉アシル化触媒及び光学分割方法 |
-
2006
- 2006-05-16 US US11/919,968 patent/US20100048549A1/en not_active Abandoned
- 2006-05-16 CA CA002609161A patent/CA2609161A1/en not_active Abandoned
- 2006-05-16 WO PCT/FI2006/050197 patent/WO2006123020A1/en not_active Ceased
- 2006-05-16 EP EP06725954A patent/EP1885693A4/en not_active Withdrawn
- 2006-05-16 JP JP2008511739A patent/JP2008540618A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20100048549A1 (en) | 2010-02-25 |
| WO2006123020A1 (en) | 2006-11-23 |
| EP1885693A4 (en) | 2010-09-15 |
| JP2008540618A (ja) | 2008-11-20 |
| EP1885693A1 (en) | 2008-02-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20130516 |