UA80190C2 - Sustituted indoline and indole derivatives - Google Patents

Sustituted indoline and indole derivatives Download PDF

Info

Publication number: UA80190C2
Authority: UA; Ukraine
Prior art keywords: alk; cycloalk; dihydro; indol; halogen
Prior art date: 2003-04-25

Application number

UAA200509297A

Other languages

English (en)

Ukrainian (uk)

Inventor

Nikolay Khanzhin

Mario Rottlonder

William Patrick Watson

Original Assignee

Lundbeck & Co As H

Priority date (The priority date 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 date listed.)

2003-04-25

Filing date

2004-04-23

Publication date

2007-08-27

2004-04-23 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2004-04-23 Priority claimed from PCT/DK2004/000283 external-priority patent/WO2004096767A1/en

2007-08-27 Publication of UA80190C2 publication Critical patent/UA80190C2/uk

Links

SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims description 25
150000002475 indoles Chemical class 0.000 title description 8
229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 44
150000001875 compounds Chemical class 0.000 claims description 424
239000001257 hydrogen Substances 0.000 claims description 50
229910052739 hydrogen Inorganic materials 0.000 claims description 50
229910052757 nitrogen Inorganic materials 0.000 claims description 45
125000004433 nitrogen atom Chemical group N* 0.000 claims description 43
-1 Св-aluk(en/yn)yl Substances 0.000 claims description 42
125000005842 heteroatom Chemical group 0.000 claims description 40
150000002431 hydrogen Chemical class 0.000 claims description 40
206010010904 Convulsion Diseases 0.000 claims description 32
229920006395 saturated elastomer Polymers 0.000 claims description 32
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
229910052709 silver Inorganic materials 0.000 claims description 30
229910052736 halogen Inorganic materials 0.000 claims description 27
150000002367 halogens Chemical class 0.000 claims description 27
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 25
208000019901 Anxiety disease Diseases 0.000 claims description 24
208000035475 disorder Diseases 0.000 claims description 23
206010015037 epilepsy Diseases 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
125000002252 acyl group Chemical group 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000004093 cyano group Chemical group *C#N 0.000 claims description 21
230000000694 effects Effects 0.000 claims description 21
108020001213 potassium channel Proteins 0.000 claims description 20
102000004257 Potassium Channel Human genes 0.000 claims description 19
230000002265 prevention Effects 0.000 claims description 18
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 17
208000004296 neuralgia Diseases 0.000 claims description 17
208000021722 neuropathic pain Diseases 0.000 claims description 17
239000008194 pharmaceutical composition Substances 0.000 claims description 17
125000004430 oxygen atom Chemical group O* 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 14
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 13
230000005764 inhibitory process Effects 0.000 claims description 13
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 claims description 13
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical class CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 11
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical class C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 11
150000002500 ions Chemical class 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 10
230000001537 neural effect Effects 0.000 claims description 10
230000004770 neurodegeneration Effects 0.000 claims description 10
239000003085 diluting agent Substances 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
150000002476 indolines Chemical class 0.000 claims description 9
208000015122 neurodegenerative disease Diseases 0.000 claims description 9
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 8
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 8
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125000004434 sulfur atom Chemical group 0.000 claims description 7
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229910052717 sulfur Inorganic materials 0.000 claims description 6
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HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
208000019906 panic disease Diseases 0.000 claims description 5
208000028173 post-traumatic stress disease Diseases 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
DWADUBFYTSATQR-UHFFFAOYSA-N 1-[(5-chlorothiophen-2-yl)methyl]-2,3-dihydroindol-5-amine Chemical compound C1CC2=CC(N)=CC=C2N1CC1=CC=C(Cl)S1 DWADUBFYTSATQR-UHFFFAOYSA-N 0.000 claims description 4
208000030507 AIDS Diseases 0.000 claims description 4
229910017982 Ag—Si Inorganic materials 0.000 claims description 4
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
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206010070863 Toxicity to various agents Diseases 0.000 claims description 3
206010053552 allodynia Diseases 0.000 claims description 3
STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 3
208000005809 status epilepticus Diseases 0.000 claims description 3
UEERNRSKJQAXQM-UHFFFAOYSA-N 1-(1-benzyl-2,3-dihydroindol-5-yl)-3-phenylurea Chemical compound C=1C=C2N(CC=3C=CC=CC=3)CCC2=CC=1NC(=O)NC1=CC=CC=C1 UEERNRSKJQAXQM-UHFFFAOYSA-N 0.000 claims description 2
241000124008 Mammalia Species 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
230000000917 hyperalgesic effect Effects 0.000 claims description 2
NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
101100001447 Pseudomonas oleovorans alkK gene Proteins 0.000 claims 1
QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 claims 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
229940080818 propionamide Drugs 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 71
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
125000001424 substituent group Chemical group 0.000 description 48
239000000243 solution Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
238000000034 method Methods 0.000 description 27
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
PCOBBVZJEWWZFR-UHFFFAOYSA-N ezogabine Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(F)C=C1 PCOBBVZJEWWZFR-UHFFFAOYSA-N 0.000 description 15
229960003312 retigabine Drugs 0.000 description 15
239000002904 solvent Substances 0.000 description 15
125000001072 heteroaryl group Chemical group 0.000 description 14
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 14
238000001914 filtration Methods 0.000 description 13
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
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230000001773 anti-convulsant effect Effects 0.000 description 11
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229910002699 Ag–S Inorganic materials 0.000 description 10
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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
150000001299 aldehydes Chemical class 0.000 description 8
229960003965 antiepileptics Drugs 0.000 description 8
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 5
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UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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PBJUNZJWGZTSKL-MRXNPFEDSA-N tiagabine Chemical compound C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C PBJUNZJWGZTSKL-MRXNPFEDSA-N 0.000 description 1
229960001918 tiagabine Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229960004394 topiramate Drugs 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
210000000427 trigeminal ganglion Anatomy 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
210000001213 vestibule labyrinth Anatomy 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
229940046009 vitamin E Drugs 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
229960002911 zonisamide Drugs 0.000 description 1
UBQNRHZMVUUOMG-UHFFFAOYSA-N zonisamide Chemical compound C1=CC=C2C(CS(=O)(=O)N)=NOC2=C1 UBQNRHZMVUUOMG-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/40—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
- A61K31/403—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 condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

UAA200509297A 2003-04-25 2004-04-23 Sustituted indoline and indole derivatives UA80190C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA200300631		2003-04-25
PCT/DK2004/000283 WO2004096767A1 (en)	2003-04-25	2004-04-23	Sustituted indoline and indole derivatives

Publications (1)

Publication Number	Publication Date
UA80190C2 true UA80190C2 (en)	2007-08-27

Family

ID=58707218

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200509297A UA80190C2 (en)	2003-04-25	2004-04-23	Sustituted indoline and indole derivatives

Country Status (10)

Country	Link
KR (1)	KR20060004957A (is)
CN (1)	CN1777582A (is)
AR (1)	AR044517A1 (is)
BR (1)	BRPI0409317A (is)
CA (1)	CA2523102A1 (is)
EA (1)	EA200501669A1 (is)
IS (1)	IS8002A (is)
NZ (1)	NZ541999A (is)
UA (1)	UA80190C2 (is)
ZA (1)	ZA200507186B (is)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103508960B (zh) *	2012-06-29	2017-12-12	江苏先声药业有限公司	苯并杂环衍生物
CN108863893A (zh) *	2018-07-09	2018-11-23	湖南博隽生物医药有限公司	二氢吲哚类衍生物及其在药物中的应用
CN112010808B (zh) *	2019-05-31	2021-11-30	上海挚盟医药科技有限公司	作为钾通道调节剂的四氢-1h-苯氮杂卓类化合物及其制备和应用

2004
- 2004-04-23 KR KR1020057020204A patent/KR20060004957A/ko not_active Ceased
- 2004-04-23 CA CA002523102A patent/CA2523102A1/en not_active Abandoned
- 2004-04-23 CN CNA2004800110190A patent/CN1777582A/zh active Pending
- 2004-04-23 NZ NZ541999A patent/NZ541999A/en unknown
- 2004-04-23 UA UAA200509297A patent/UA80190C2/uk unknown
- 2004-04-23 AR ARP040101392A patent/AR044517A1/es not_active Application Discontinuation
- 2004-04-23 ZA ZA200507186A patent/ZA200507186B/en unknown
- 2004-04-23 BR BRPI0409317-8A patent/BRPI0409317A/pt not_active IP Right Cessation
- 2004-04-23 EA EA200501669A patent/EA200501669A1/ru unknown
2005
- 2005-08-29 IS IS8002A patent/IS8002A/is unknown

Also Published As

Publication number	Publication date
IS8002A (is)	2005-08-29
EA200501669A1 (ru)	2006-04-28
CA2523102A1 (en)	2004-11-11
ZA200507186B (en)	2006-11-29
BRPI0409317A (pt)	2006-04-25
AR044517A1 (es)	2005-09-14
CN1777582A (zh)	2006-05-24
KR20060004957A (ko)	2006-01-16
NZ541999A (en)	2009-03-31

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