CA2603104A1 - Tetrahydrothiopyrano pyrazole cannabinoid modulators - Google Patents
Tetrahydrothiopyrano pyrazole cannabinoid modulators Download PDFInfo
- Publication number
- CA2603104A1 CA2603104A1 CA002603104A CA2603104A CA2603104A1 CA 2603104 A1 CA2603104 A1 CA 2603104A1 CA 002603104 A CA002603104 A CA 002603104A CA 2603104 A CA2603104 A CA 2603104A CA 2603104 A1 CA2603104 A1 CA 2603104A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- tetrahydro
- thiopyrano
- pyrazole
- carboxylic 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
- 229930003827 cannabinoid Natural products 0.000 title description 103
- 239000003557 cannabinoid Substances 0.000 title description 103
- UBEXPFAJZMPWAL-UHFFFAOYSA-N 1,2,3,3a-tetrahydrothiopyrano[3,2-c]pyrazole Chemical compound C1=CSC2CNNC2=C1 UBEXPFAJZMPWAL-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 251
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 250
- 208000035475 disorder Diseases 0.000 claims abstract description 130
- 201000010099 disease Diseases 0.000 claims abstract description 120
- 238000000034 method Methods 0.000 claims abstract description 115
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 115
- 230000001404 mediated effect Effects 0.000 claims abstract description 72
- 102000005962 receptors Human genes 0.000 claims abstract description 60
- 108020003175 receptors Proteins 0.000 claims abstract description 60
- 239000000203 mixture Substances 0.000 claims description 113
- -1 C3-C12 cycloalkyl Chemical group 0.000 claims description 107
- 125000000217 alkyl group Chemical group 0.000 claims description 100
- 125000003118 aryl group Chemical group 0.000 claims description 78
- 229910052736 halogen Inorganic materials 0.000 claims description 75
- 150000002367 halogens Chemical class 0.000 claims description 75
- 125000003545 alkoxy group Chemical group 0.000 claims description 72
- 238000002560 therapeutic procedure Methods 0.000 claims description 64
- 125000000623 heterocyclic group Chemical group 0.000 claims description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 239000013066 combination product Substances 0.000 claims description 46
- 229940127555 combination product Drugs 0.000 claims description 46
- 125000002947 alkylene group Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 239000003433 contraceptive agent Substances 0.000 claims description 33
- 239000001961 anticonvulsive agent Substances 0.000 claims description 31
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 30
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 30
- 229940124558 contraceptive agent Drugs 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 claims description 24
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 24
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 208000008589 Obesity Diseases 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 22
- 235000020824 obesity Nutrition 0.000 claims description 22
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 239000002469 receptor inverse agonist Substances 0.000 claims description 20
- KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical group C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 claims description 19
- 239000000556 agonist Substances 0.000 claims description 19
- 229960004394 topiramate Drugs 0.000 claims description 19
- 230000036528 appetite Effects 0.000 claims description 18
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- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 claims description 16
- FJYWNYLUZBMVKI-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-amine Chemical compound C1CCC2CN(N)CC21 FJYWNYLUZBMVKI-UHFFFAOYSA-N 0.000 claims description 16
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 claims description 16
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 claims description 16
- 230000001773 anti-convulsant effect Effects 0.000 claims description 16
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 16
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 229960003965 antiepileptics Drugs 0.000 claims description 15
- 230000004060 metabolic process Effects 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
- XBWOPGDJMAJJDG-SSDOTTSWSA-N (1r)-1-cyclohexylethanamine Chemical compound C[C@@H](N)C1CCCCC1 XBWOPGDJMAJJDG-SSDOTTSWSA-N 0.000 claims description 12
- 206010012601 diabetes mellitus Diseases 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 229960002870 gabapentin Drugs 0.000 claims description 11
- 229940125425 inverse agonist Drugs 0.000 claims description 11
- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 claims description 11
- 239000000651 prodrug Substances 0.000 claims description 11
- 229940002612 prodrug Drugs 0.000 claims description 11
- 229960000604 valproic acid Drugs 0.000 claims description 11
- 102100033868 Cannabinoid receptor 1 Human genes 0.000 claims description 10
- 101710187010 Cannabinoid receptor 1 Proteins 0.000 claims description 10
- 206010061218 Inflammation Diseases 0.000 claims description 10
- 208000002193 Pain Diseases 0.000 claims description 10
- 125000001118 alkylidene group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 230000004054 inflammatory process Effects 0.000 claims description 10
- 229960001848 lamotrigine Drugs 0.000 claims description 10
- 230000036407 pain Effects 0.000 claims description 10
- 239000002464 receptor antagonist Substances 0.000 claims description 10
- 229940124597 therapeutic agent Drugs 0.000 claims description 10
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 claims description 9
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 claims description 9
- 206010010904 Convulsion Diseases 0.000 claims description 9
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 claims description 9
- 230000013016 learning Effects 0.000 claims description 9
- 230000015654 memory Effects 0.000 claims description 9
- 229960000623 carbamazepine Drugs 0.000 claims description 8
- 230000010261 cell growth Effects 0.000 claims description 8
- 230000019771 cognition Effects 0.000 claims description 8
- 230000004410 intraocular pressure Effects 0.000 claims description 8
- 208000011117 substance-related disease Diseases 0.000 claims description 8
- 208000007101 Muscle Cramp Diseases 0.000 claims description 7
- 208000005392 Spasm Diseases 0.000 claims description 7
- 230000002254 contraceptive effect Effects 0.000 claims description 7
- 230000006742 locomotor activity Effects 0.000 claims description 7
- 239000002207 metabolite Substances 0.000 claims description 7
- 210000000056 organ Anatomy 0.000 claims description 7
- 201000009032 substance abuse Diseases 0.000 claims description 7
- 231100000736 substance abuse Toxicity 0.000 claims description 7
- XBWOPGDJMAJJDG-ZETCQYMHSA-N (1s)-1-cyclohexylethanamine Chemical compound C[C@H](N)C1CCCCC1 XBWOPGDJMAJJDG-ZETCQYMHSA-N 0.000 claims description 6
- 208000010412 Glaucoma Diseases 0.000 claims description 6
- UGBKOURNNQREPE-UHFFFAOYSA-N azepan-1-amine Chemical compound NN1CCCCCC1 UGBKOURNNQREPE-UHFFFAOYSA-N 0.000 claims description 6
- 230000008602 contraction Effects 0.000 claims description 6
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 6
- CBYXIIFIKSBHEY-UHFFFAOYSA-N 2,2,4-trimethylbicyclo[2.2.1]heptan-3-amine Chemical compound C1CC2(C)C(N)C(C)(C)C1C2 CBYXIIFIKSBHEY-UHFFFAOYSA-N 0.000 claims description 5
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 229960002036 phenytoin Drugs 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- PDNHLCRMUIGNBV-ZCFIWIBFSA-N (1r)-1-pyridin-2-ylethanamine Chemical compound C[C@@H](N)C1=CC=CC=N1 PDNHLCRMUIGNBV-ZCFIWIBFSA-N 0.000 claims description 4
- LOPKSXMQWBYUOI-DTWKUNHWSA-N (1r,2s)-1-amino-2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2[C@@H](N)[C@@H](O)CC2=C1 LOPKSXMQWBYUOI-DTWKUNHWSA-N 0.000 claims description 4
- BWSIKGOGLDNQBZ-ZCFIWIBFSA-N (2r)-2-(methoxymethyl)pyrrolidin-1-amine Chemical compound COC[C@H]1CCCN1N BWSIKGOGLDNQBZ-ZCFIWIBFSA-N 0.000 claims description 4
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 claims description 4
- 208000019022 Mood disease Diseases 0.000 claims description 4
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229940127234 oral contraceptive Drugs 0.000 claims description 4
- 239000003539 oral contraceptive agent Substances 0.000 claims description 4
- 239000000583 progesterone congener Substances 0.000 claims description 4
- 239000000779 smoke Substances 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- LOPKSXMQWBYUOI-BDAKNGLRSA-N (1s,2r)-1-amino-2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2[C@H](N)[C@H](O)CC2=C1 LOPKSXMQWBYUOI-BDAKNGLRSA-N 0.000 claims description 3
- PQMCFTMVQORYJC-WDSKDSINSA-N (1s,2s)-2-aminocyclohexan-1-ol Chemical compound N[C@H]1CCCC[C@@H]1O PQMCFTMVQORYJC-WDSKDSINSA-N 0.000 claims description 3
- BWSIKGOGLDNQBZ-LURJTMIESA-N (2s)-2-(methoxymethyl)pyrrolidin-1-amine Chemical compound COC[C@@H]1CCCN1N BWSIKGOGLDNQBZ-LURJTMIESA-N 0.000 claims description 3
- NLRZHTGURNWLIU-SYKJDFLGSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1r,2r)-2-hydroxycyclopentyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound O[C@@H]1CCC[C@H]1NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 NLRZHTGURNWLIU-SYKJDFLGSA-N 0.000 claims description 3
- PELZRCABPQTZBQ-NNIWKIFQSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1s)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 PELZRCABPQTZBQ-NNIWKIFQSA-N 0.000 claims description 3
- PBQPQDQJQSMOMU-BFJWEILNSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H]1C2=CC=CC=C2C[C@H]1O)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 PBQPQDQJQSMOMU-BFJWEILNSA-N 0.000 claims description 3
- POOVBRNGDMMGJG-XDHOZWIPSA-N (7z)-1-(2,4-dichlorophenyl)-n-(2,6-dimethylpiperidin-1-yl)-7-[(4-fluorophenyl)methylidene]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound CC1CCCC(C)N1NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 POOVBRNGDMMGJG-XDHOZWIPSA-N 0.000 claims description 3
- PJYLIEXJKCUSPD-UOBPLZBXSA-N (7z)-2-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1r)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C(N(N=C12)C=3C(=CC(Cl)=CC=3)Cl)=C1CSC\C2=C/C1=CC=C(F)C=C1 PJYLIEXJKCUSPD-UOBPLZBXSA-N 0.000 claims description 3
- GJOXDOACLBZDBM-OQLLNIDSSA-N (7z)-n',1-bis(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-4h-thiopyrano[4,3-c]pyrazole-3-carbohydrazide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NNC=3C(=CC(Cl)=CC=3)Cl)C=3C(=CC(Cl)=CC=3)Cl)=C2CSC\1 GJOXDOACLBZDBM-OQLLNIDSSA-N 0.000 claims description 3
- OYROSPQCAJMZKB-VXLYETTFSA-N (7z)-n-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CC4CCCC4C3)C=3C(=CC(Cl)=CC=3)Cl)=C2CSC\1 OYROSPQCAJMZKB-VXLYETTFSA-N 0.000 claims description 3
- IZYVRXYTJZRPSP-QGOAFFKASA-N (7z)-n-(azepan-1-yl)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCCCCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CSC\1 IZYVRXYTJZRPSP-QGOAFFKASA-N 0.000 claims description 3
- VYBOXOIFQOFFMO-UHFFFAOYSA-N 1-benzyl-6,7-dihydro-4h-thiopyrano[4,3-c]pyrazole-3-carboxylic acid Chemical compound C1=2CCSCC=2C(C(=O)O)=NN1CC1=CC=CC=C1 VYBOXOIFQOFFMO-UHFFFAOYSA-N 0.000 claims description 3
- UAHWWAIVYPJROV-UHFFFAOYSA-N 2,6-dimethylpiperidin-1-amine Chemical compound CC1CCCC(C)N1N UAHWWAIVYPJROV-UHFFFAOYSA-N 0.000 claims description 3
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- ZXINDFJFLUVDAF-SFQUDFHCSA-N [(7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-4h-thiopyrano[4,3-c]pyrazol-3-yl]-piperidin-1-ylmethanone Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)N3CCCCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CSC\1 ZXINDFJFLUVDAF-SFQUDFHCSA-N 0.000 claims description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—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
- A61K31/4162—1,2-Diazoles condensed with heterocyclic ring systems
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Endocrinology (AREA)
- Immunology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66689805P | 2005-03-31 | 2005-03-31 | |
| US60/666.898 | 2005-03-31 | ||
| PCT/US2006/009424 WO2006107561A1 (en) | 2005-03-31 | 2006-03-16 | Tetrahydrothiopyrano pyrazole cannabinoid modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2603104A1 true CA2603104A1 (en) | 2006-10-12 |
Family
ID=36587178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002603104A Abandoned CA2603104A1 (en) | 2005-03-31 | 2006-03-16 | Tetrahydrothiopyrano pyrazole cannabinoid modulators |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US20060223798A1 (enExample) |
| EP (1) | EP1863479B1 (enExample) |
| JP (1) | JP5127697B2 (enExample) |
| KR (1) | KR20080004559A (enExample) |
| CN (1) | CN101189007A (enExample) |
| AT (1) | ATE416768T1 (enExample) |
| AU (1) | AU2006232945B2 (enExample) |
| BR (1) | BRPI0609790A2 (enExample) |
| CA (1) | CA2603104A1 (enExample) |
| CO (1) | CO6321135A2 (enExample) |
| CR (1) | CR9479A (enExample) |
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| NO (1) | NO20075463L (enExample) |
| WO (1) | WO2006107561A1 (enExample) |
| ZA (1) | ZA200709342B (enExample) |
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| CN101863903B (zh) * | 2010-06-08 | 2014-03-12 | 沈阳药科大学 | 1,4-二氢噻吩并[3’,2’:5,6]噻喃并[4,3-c]吡唑-3-羧酸衍生物及其应用 |
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| FR2800375B1 (fr) * | 1999-11-03 | 2004-07-23 | Sanofi Synthelabo | Derives tricycliques d'acide pyrazolecarboxylique, leur preparation, les compositions pharmaceutiques en contenant |
| JP2004502642A (ja) * | 2000-02-11 | 2004-01-29 | ブリストル−マイヤーズ スクイブ カンパニー | カンナビノイドレセプターモジュレーター、それらの製造方法、および呼吸系および非呼吸系疾患の処置のためのカンナビノイドレセプターモジュレーターの使用 |
| WO2003035005A2 (en) * | 2001-10-26 | 2003-05-01 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
| US20040214856A1 (en) * | 2003-04-23 | 2004-10-28 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| US7145012B2 (en) * | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
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2006
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- 2006-03-16 US US11/376,844 patent/US20060223798A1/en not_active Abandoned
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2007
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Also Published As
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|---|---|
| US7524964B2 (en) | 2009-04-28 |
| BRPI0609790A2 (pt) | 2010-04-27 |
| WO2006107561A1 (en) | 2006-10-12 |
| KR20080004559A (ko) | 2008-01-09 |
| AU2006232945A1 (en) | 2006-10-12 |
| AU2006232945B2 (en) | 2012-02-23 |
| JP2008535829A (ja) | 2008-09-04 |
| MX2007012233A (es) | 2008-03-18 |
| EP1863479B1 (en) | 2008-12-10 |
| US20060223798A1 (en) | 2006-10-05 |
| CO6321135A2 (es) | 2011-09-20 |
| DE602006004197D1 (de) | 2009-01-22 |
| EA200702130A1 (ru) | 2008-04-28 |
| EP1863479A1 (en) | 2007-12-12 |
| CR9479A (es) | 2008-09-09 |
| US20080085899A1 (en) | 2008-04-10 |
| IL186430A0 (en) | 2008-01-20 |
| ATE416768T1 (de) | 2008-12-15 |
| ZA200709342B (en) | 2009-09-30 |
| NO20075463L (no) | 2007-12-21 |
| CN101189007A (zh) | 2008-05-28 |
| JP5127697B2 (ja) | 2013-01-23 |
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