TW200906818A - Chemical compounds - Google Patents

Chemical compounds Download PDF

Info

Publication number: TW200906818A
Authority: TW; Taiwan
Prior art keywords: group; alkyl; heterocyclic; optionally substituted; carbon
Prior art date: 2007-07-31

Application number

TW097128670A

Other languages

English (en)

Chinese (zh)

Inventor

Lynsie Almeida

Brian Aquila

Claudio Edmundo Chuaqui

Hui-Ping Guan

Shan Huang

Stephanos Ioannidis

Michelle Lamb

Bo Peng

Jie Shi

Mei Su

Qibin Su

Original Assignee

Astrazeneca Ab

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.)

2007-07-31

Filing date

2008-07-29

Publication date

2009-02-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40304964&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=TW200906818(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2008-07-29 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2009-02-16 Publication of TW200906818A publication Critical patent/TW200906818A/zh

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 234
238000000034 method Methods 0.000 claims abstract description 117
206010028980 Neoplasm Diseases 0.000 claims abstract description 60
150000003839 salts Chemical class 0.000 claims abstract description 57
201000011510 cancer Diseases 0.000 claims abstract description 41
238000011282 treatment Methods 0.000 claims abstract description 25
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 431
125000000217 alkyl group Chemical group 0.000 claims description 254
-1 i-based Chemical group 0.000 claims description 229
229910052799 carbon Inorganic materials 0.000 claims description 179
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 176
125000004452 carbocyclyl group Chemical group 0.000 claims description 149
125000002837 carbocyclic group Chemical group 0.000 claims description 109
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 77
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 75
125000000304 alkynyl group Chemical group 0.000 claims description 58
125000003342 alkenyl group Chemical group 0.000 claims description 50
125000005843 halogen group Chemical group 0.000 claims description 37
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 32
241001465754 Metazoa Species 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 26
125000004093 cyano group Chemical group *C#N 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 21
125000004122 cyclic group Chemical group 0.000 claims description 18
239000007789 gas Substances 0.000 claims description 18
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 17
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
125000006239 protecting group Chemical group 0.000 claims description 15
239000000126 substance Substances 0.000 claims description 15
125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 12
238000006467 substitution reaction Methods 0.000 claims description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 9
229910052707 ruthenium Inorganic materials 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
239000004575 stone Substances 0.000 claims description 7
125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 6
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
150000002923 oximes Chemical class 0.000 claims description 6
230000036961 partial effect Effects 0.000 claims description 6
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
150000002429 hydrazines Chemical class 0.000 claims description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 3
150000004032 porphyrins Chemical class 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 claims 1
TVPDWWYLCZDJKD-UHFFFAOYSA-N 2-morpholin-3-ylethanol Chemical compound OCCC1COCCN1 TVPDWWYLCZDJKD-UHFFFAOYSA-N 0.000 claims 1
UFMLRLOUIAVFNQ-UHFFFAOYSA-N 3-sulfanylpurine Chemical compound SN1C=NC=C2N=CN=C12 UFMLRLOUIAVFNQ-UHFFFAOYSA-N 0.000 claims 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 1
125000004212 difluorophenyl group Chemical group 0.000 claims 1
125000001041 indolyl group Chemical group 0.000 claims 1
125000005358 mercaptoalkyl group Chemical group 0.000 claims 1
PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
125000003431 oxalo group Chemical group 0.000 claims 1
IPOVLZSJBYKHHU-UHFFFAOYSA-N piperidin-3-ylmethanamine Chemical compound NCC1CCCNC1 IPOVLZSJBYKHHU-UHFFFAOYSA-N 0.000 claims 1
125000004646 sulfenyl group Chemical group S(*)* 0.000 claims 1
208000014767 Myeloproliferative disease Diseases 0.000 abstract description 12
239000000543 intermediate Substances 0.000 description 391
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 360
235000019439 ethyl acetate Nutrition 0.000 description 173
239000000243 solution Substances 0.000 description 163
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 138
238000006243 chemical reaction Methods 0.000 description 121
239000000203 mixture Substances 0.000 description 110
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 105
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
239000002585 base Substances 0.000 description 80
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 80
239000011541 reaction mixture Substances 0.000 description 70
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 65
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 61
230000002829 reductive effect Effects 0.000 description 54
230000015572 biosynthetic process Effects 0.000 description 51
OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 50
239000007787 solid Substances 0.000 description 48
238000003786 synthesis reaction Methods 0.000 description 48
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 47
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
229920006395 saturated elastomer Polymers 0.000 description 39
229910052757 nitrogen Inorganic materials 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
239000003921 oil Substances 0.000 description 36
235000019198 oils Nutrition 0.000 description 36
239000007858 starting material Substances 0.000 description 35
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
238000003971 tillage Methods 0.000 description 30
229910001868 water Inorganic materials 0.000 description 30
238000000746 purification Methods 0.000 description 29
239000002904 solvent Substances 0.000 description 29
239000002253 acid Substances 0.000 description 26
239000012044 organic layer Substances 0.000 description 26
239000000047 product Substances 0.000 description 26
150000001412 amines Chemical class 0.000 description 25
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 25
239000000463 material Substances 0.000 description 24
238000003756 stirring Methods 0.000 description 24
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 22
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 21
239000003112 inhibitor Substances 0.000 description 20
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
210000004027 cell Anatomy 0.000 description 19
239000003039 volatile agent Substances 0.000 description 19
102100033793 ALK tyrosine kinase receptor Human genes 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 description 16
125000006413 ring segment Chemical group 0.000 description 16
239000000725 suspension Substances 0.000 description 16
238000005160 1H NMR spectroscopy Methods 0.000 description 15
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 15
102000042838 JAK family Human genes 0.000 description 15
108091082332 JAK family Proteins 0.000 description 15
102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 description 15
238000001704 evaporation Methods 0.000 description 15
229910052717 sulfur Inorganic materials 0.000 description 15
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 14
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 14
239000007864 aqueous solution Substances 0.000 description 14
238000004440 column chromatography Methods 0.000 description 14
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230000008020 evaporation Effects 0.000 description 14
208000002154 non-small cell lung carcinoma Diseases 0.000 description 14
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 14
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239000012074 organic phase Substances 0.000 description 13
239000011734 sodium Substances 0.000 description 13
FJNLCHNQVJVCPY-UHFFFAOYSA-N 2-n-methoxy-2-n-methyl-4-n,6-n-dipropyl-1,3,5-triazine-2,4,6-triamine Chemical compound CCCNC1=NC(NCCC)=NC(N(C)OC)=N1 FJNLCHNQVJVCPY-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
239000012267 brine Substances 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
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BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 12
125000004076 pyridyl group Chemical group 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
208000011580 syndromic disease Diseases 0.000 description 12
206010058314 Dysplasia Diseases 0.000 description 11
239000004480 active ingredient Substances 0.000 description 11
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210000001185 bone marrow Anatomy 0.000 description 10
239000013078 crystal Substances 0.000 description 10
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 10
125000001153 fluoro group Chemical group F* 0.000 description 10
239000012071 phase Substances 0.000 description 10
239000002689 soil Substances 0.000 description 10
208000026310 Breast neoplasm Diseases 0.000 description 9
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125000006615 aromatic heterocyclic group Chemical group 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
125000002950 monocyclic group Chemical group 0.000 description 9
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239000000843 powder Substances 0.000 description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
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208000000587 small cell lung carcinoma Diseases 0.000 description 9
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101000617830 Homo sapiens Sterol O-acyltransferase 1 Proteins 0.000 description 8
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102100021993 Sterol O-acyltransferase 1 Human genes 0.000 description 8
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150000004985 diamines Chemical class 0.000 description 8
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UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 7
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- C07D403/14—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 three or more hetero rings
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

TW097128670A 2007-07-31 2008-07-29 Chemical compounds TW200906818A (en)

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US95315807P	2007-07-31	2007-07-31

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TW200906818A true TW200906818A (en)	2009-02-16

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TW097128670A TW200906818A (en)	2007-07-31	2008-07-29	Chemical compounds

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AR (1)	AR069899A1 (es)
CL (1)	CL2008002243A1 (es)
PE (1)	PE20090895A1 (es)
TW (1)	TW200906818A (es)
UY (1)	UY31254A1 (es)
WO (1)	WO2009016410A2 (es)

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AR091858A1 (es) *	2012-07-25	2015-03-04	Sova Pharmaceuticals Inc	INHIBIDORES DE CISTATIONIN-g-LIASA (CSE)
NZ706999A (en)	2012-10-15	2018-12-21	Agios Pharmaceuticals Inc	Inhibitors of mutant isocitrate dehydrogenase and therapeutical uses thereof
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WO2015003355A2 (en) *	2013-07-11	2015-01-15	Agios Pharmaceuticals, Inc.	Therapeutically active compounds and their methods of use
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US9968595B2 (en)	2014-03-14	2018-05-15	Agios Pharmaceuticals, Inc.	Pharmaceutical compositions of therapeutically active compounds
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HUE063541T2 (hu)	2015-06-11	2024-01-28	Agios Pharmaceuticals Inc	Eljárások piruvát-kináz aktivátorok alkalmazására
IL258684B2 (en)	2015-10-15	2023-04-01	Agios Pharmaceuticals Inc	Combination therapy including an isocitrate dehydrogenase (1idh) inhibitor for use in the treatment of acute myelogenous leukemia (aml) characterized by the presence of a mutant allele of 1idh
CN108697698B (zh)	2015-10-15	2021-12-03	阿吉奥斯制药公司	用于治疗恶性肿瘤的组合疗法
US20200199136A1 (en) *	2017-08-28	2020-06-25	Acurastem Inc.	Pikfyve kinase inhibitors
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2008
- 2008-07-29 TW TW097128670A patent/TW200906818A/zh unknown
- 2008-07-30 CL CL2008002243A patent/CL2008002243A1/es unknown
- 2008-07-30 UY UY31254A patent/UY31254A1/es unknown
- 2008-07-31 PE PE2008001287A patent/PE20090895A1/es not_active Application Discontinuation
- 2008-07-31 AR ARP080103333A patent/AR069899A1/es unknown
- 2008-07-31 WO PCT/GB2008/050644 patent/WO2009016410A2/en not_active Ceased

Also Published As

Publication number	Publication date
UY31254A1 (es)	2009-04-30
WO2009016410A3 (en)	2009-07-02
AR069899A1 (es)	2010-03-03
CL2008002243A1 (es)	2009-08-21
WO2009016410A2 (en)	2009-02-05
PE20090895A1 (es)	2009-08-08

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