CA2577879C - Substituted thienopyrrole carboxylic acid amides, pyrrolothiazole carboxylic acid amides, and related analogs as inhibitors of casein kinase i.epsilon. - Google Patents
Substituted thienopyrrole carboxylic acid amides, pyrrolothiazole carboxylic acid amides, and related analogs as inhibitors of casein kinase i.epsilon. Download PDFInfo
- Publication number
- CA2577879C CA2577879C CA2577879A CA2577879A CA2577879C CA 2577879 C CA2577879 C CA 2577879C CA 2577879 A CA2577879 A CA 2577879A CA 2577879 A CA2577879 A CA 2577879A CA 2577879 C CA2577879 C CA 2577879C
- Authority
- CA
- Canada
- Prior art keywords
- carboxylic acid
- acid amide
- c6alkyl
- thieno
- pyrrole
- 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.)
- Expired - Fee Related
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- 102000008122 Casein Kinase I Human genes 0.000 title claims abstract description 10
- 108010049812 Casein Kinase I Proteins 0.000 title claims abstract description 10
- 239000003112 inhibitor Substances 0.000 title abstract description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title description 8
- YRVMMDZANCTYNL-UHFFFAOYSA-N 2h-pyrrolo[2,3-d][1,3]thiazole-2-carboxamide Chemical class C1=NC2=NC(C(=O)N)SC2=C1 YRVMMDZANCTYNL-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 160
- 238000000034 method Methods 0.000 claims abstract description 72
- 208000019116 sleep disease Diseases 0.000 claims abstract description 25
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 208000019022 Mood disease Diseases 0.000 claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 47
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 40
- 230000000694 effects Effects 0.000 claims description 31
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 208000035475 disorder Diseases 0.000 claims description 22
- 230000027288 circadian rhythm Effects 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 18
- 208000024714 major depressive disease Diseases 0.000 claims description 18
- 230000005764 inhibitory process Effects 0.000 claims description 16
- 208000020401 Depressive disease Diseases 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
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- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 9
- 208000028683 bipolar I disease Diseases 0.000 claims description 8
- 208000022257 bipolar II disease Diseases 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 208000020685 sleep-wake disease Diseases 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical group [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 6
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- OICWBDMISQRIEM-UHFFFAOYSA-N 2,6-bis(phenylsulfanyl)-4h-pyrrolo[3,2-d][1,3]thiazole-5-carboxamide Chemical compound N=1C=2C(SC=3C=CC=CC=3)=C(C(=O)N)NC=2SC=1SC1=CC=CC=C1 OICWBDMISQRIEM-UHFFFAOYSA-N 0.000 claims description 5
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- 230000001668 ameliorated effect Effects 0.000 claims description 5
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- RWXUROFIQSIUQV-UHFFFAOYSA-N 4-phenylsulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC=CC=C1 RWXUROFIQSIUQV-UHFFFAOYSA-N 0.000 claims description 4
- FNWSTCZNXVPFRZ-UHFFFAOYSA-N 4-pyridin-2-ylsulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC=CC=N1 FNWSTCZNXVPFRZ-UHFFFAOYSA-N 0.000 claims description 4
- ZNYIUWSBBGOLAV-UHFFFAOYSA-N 6-(3-fluorophenyl)sulfanyl-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2C=CSC=2C=1SC1=CC=CC(F)=C1 ZNYIUWSBBGOLAV-UHFFFAOYSA-N 0.000 claims description 4
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- SVGBHSTYOGQVPE-UHFFFAOYSA-N 2,6-bis[(3-methoxyphenyl)sulfanyl]-4h-pyrrolo[3,2-d][1,3]thiazole-5-carboxamide Chemical compound COC1=CC=CC(SC=2SC=3NC(=C(SC=4C=C(OC)C=CC=4)C=3N=2)C(N)=O)=C1 SVGBHSTYOGQVPE-UHFFFAOYSA-N 0.000 claims description 3
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- HOQJCJIERRLTCY-UHFFFAOYSA-N 4-(3-bromophenyl)sulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC=CC(Br)=C1 HOQJCJIERRLTCY-UHFFFAOYSA-N 0.000 claims description 3
- GHMABAHOMNASAZ-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC=CC(Cl)=C1 GHMABAHOMNASAZ-UHFFFAOYSA-N 0.000 claims description 3
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- VKJKCISGARMRPR-UHFFFAOYSA-N 6-(3-fluorophenyl)sulfanyl-2-methyl-4h-pyrrolo[3,2-d][1,3]thiazole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC(C)=NC=2C=1SC1=CC=CC(F)=C1 VKJKCISGARMRPR-UHFFFAOYSA-N 0.000 claims description 3
- FUHFQPLBCITXQI-UHFFFAOYSA-N 6-(3-methoxyphenyl)sulfanyl-2-methyl-4h-pyrrolo[3,2-d][1,3]thiazole-5-carboxamide Chemical compound COC1=CC=CC(SC=2C=3N=C(C)SC=3NC=2C(N)=O)=C1 FUHFQPLBCITXQI-UHFFFAOYSA-N 0.000 claims description 3
- DZRGVTJILNYAEW-UHFFFAOYSA-N 6-(3-methoxyphenyl)sulfanyl-4h-pyrrolo[3,2-d][1,3]thiazole-5-carboxamide Chemical compound COC1=CC=CC(SC=2C=3N=CSC=3NC=2C(N)=O)=C1 DZRGVTJILNYAEW-UHFFFAOYSA-N 0.000 claims description 3
- ZNXHNYLEVPGVHR-UHFFFAOYSA-N 6-phenylsulfanyl-4h-pyrrolo[3,2-d][1,3]thiazole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=NC=2C=1SC1=CC=CC=C1 ZNXHNYLEVPGVHR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- KHLCUPKDEHFRCJ-UHFFFAOYSA-N 2-methyl-6-[3-(trifluoromethoxy)phenyl]sulfanyl-4h-pyrrolo[3,2-d][1,3]thiazole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC(C)=NC=2C=1SC1=CC=CC(OC(F)(F)F)=C1 KHLCUPKDEHFRCJ-UHFFFAOYSA-N 0.000 claims description 2
- LLODQNWTXWAEHQ-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC(Cl)=CC(Cl)=C1 LLODQNWTXWAEHQ-UHFFFAOYSA-N 0.000 claims description 2
- NTLRFOPPLIJBSC-UHFFFAOYSA-N 4-pyridin-4-ylsulfanyl-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound NC(=O)C=1NC=2SC=CC=2C=1SC1=CC=NC=C1 NTLRFOPPLIJBSC-UHFFFAOYSA-N 0.000 claims description 2
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- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000012913 prioritisation Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000005470 propylenyl group Chemical group 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
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- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007423 screening assay Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
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- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000012128 staining reagent Substances 0.000 description 1
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- 230000001502 supplementing effect Effects 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
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- 230000003442 weekly effect Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- 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
- C07D495/04—Ortho-condensed systems
-
- 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
- A61K31/41—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
- A61K31/425—Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60334704P | 2004-08-19 | 2004-08-19 | |
| US60/603,347 | 2004-08-19 | ||
| PCT/US2005/029383 WO2006021000A2 (en) | 2004-08-19 | 2005-08-18 | Substituted thienopyrrole carboxylic acid amides, pyrrolothiazole carboxylic acid amides, and related analogs as inhibitors of casein kinase i epsilon |
Publications (2)
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|---|---|
| CA2577879A1 CA2577879A1 (en) | 2006-02-23 |
| CA2577879C true CA2577879C (en) | 2011-07-12 |
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|---|---|---|---|
| CA2577879A Expired - Fee Related CA2577879C (en) | 2004-08-19 | 2005-08-18 | Substituted thienopyrrole carboxylic acid amides, pyrrolothiazole carboxylic acid amides, and related analogs as inhibitors of casein kinase i.epsilon. |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US7393867B2 (enExample) |
| EP (1) | EP1784409B1 (enExample) |
| JP (1) | JP4869232B2 (enExample) |
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| CN (1) | CN100562521C (enExample) |
| AR (1) | AR051008A1 (enExample) |
| AT (1) | ATE471326T1 (enExample) |
| AU (1) | AU2005272584B2 (enExample) |
| BR (1) | BRPI0514419A (enExample) |
| CA (1) | CA2577879C (enExample) |
| CY (1) | CY1110775T1 (enExample) |
| DE (1) | DE602005021889D1 (enExample) |
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| GT (1) | GT200500215A (enExample) |
| HR (1) | HRP20100475T1 (enExample) |
| IL (1) | IL181158A0 (enExample) |
| JO (1) | JO2629B1 (enExample) |
| MY (1) | MY139831A (enExample) |
| PA (1) | PA8642801A1 (enExample) |
| PE (1) | PE20060630A1 (enExample) |
| PL (1) | PL1784409T3 (enExample) |
| PT (1) | PT1784409E (enExample) |
| RS (1) | RS51413B (enExample) |
| RU (1) | RU2403257C2 (enExample) |
| SI (1) | SI1784409T1 (enExample) |
| SV (1) | SV2006002190A (enExample) |
| TW (1) | TWI372149B (enExample) |
| UY (1) | UY29077A1 (enExample) |
| WO (1) | WO2006021000A2 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004312530A1 (en) | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole DAAO inhibitors |
| US8053603B2 (en) | 2006-01-06 | 2011-11-08 | Sunovion Pharmaceuticals Inc. | Tetralone-based monoamine reuptake inhibitors |
| CA2636324C (en) | 2006-01-06 | 2012-03-20 | Sepracor Inc. | Cycloalkylamines as monoamine reuptake inhibitors |
| AU2007233041B2 (en) | 2006-03-31 | 2013-05-02 | Sepracor Inc. | Preparation of chiral amides and amines |
| US7884124B2 (en) | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| US7902252B2 (en) | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| EP1955699A1 (en) * | 2007-02-08 | 2008-08-13 | Boehringer Ingelheim Pharma GmbH & Co. KG | Use of flibanserin for the treatment of insomnia |
| JP5420534B2 (ja) | 2007-05-31 | 2014-02-19 | サノビオン ファーマシューティカルズ インク | モノアミン再取り込み阻害薬としてのフェニル置換シクロアルキルアミン |
| EP2397481B1 (en) * | 2009-02-12 | 2014-03-12 | Pharmadesign, Inc. | Inhibitor of casein kinase 1delta and casein kinase 1epsilon |
| EP2435443B1 (en) * | 2009-05-28 | 2013-07-31 | Vertex Pharmaceuticals Incorporated | Aminopyrazole triazolothiadiazole inhibitors of c-met protien kinase |
| HRP20140252T1 (hr) * | 2009-10-28 | 2014-04-25 | Pfizer Inc. | Derivati imidazola kao inhibitori kazeinske kinaze |
| DE102009058280A1 (de) * | 2009-12-14 | 2011-06-16 | Merck Patent Gmbh | Thiazolderivate |
| RU2562833C2 (ru) | 2010-08-09 | 2015-09-10 | НБ Хелс Лаборатори Ко. Лтд. | Ингибитор казеинкиназы 1 дельта и казеинкиназы 1 е |
| CN109748927A (zh) * | 2017-11-03 | 2019-05-14 | 上海交通大学医学院附属瑞金医院 | 杂芳基酰胺类化合物、其制备方法、药用组合物及其应用 |
Family Cites Families (3)
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| SE9702001D0 (sv) * | 1997-05-28 | 1997-05-28 | Astra Pharma Prod | Novel compounds |
| WO2000075669A1 (en) * | 1999-06-08 | 2000-12-14 | Aventis Pharmaceuticals Inc. | Screening methods for altering circadian rhythm proteins |
| AU2004303826A1 (en) * | 2003-12-11 | 2005-07-07 | Aventis Pharmaceuticals Inc. | Substituted 1H-pyrrolo[3,2-b, 3,2-c, and 2,3-c]pyridine-2-carboxamides and related analogs as inhibitors of casein kinase I Epsilon |
-
2005
- 2005-07-18 JO JO2005104A patent/JO2629B1/en active
- 2005-08-09 SV SV2005002190A patent/SV2006002190A/es not_active Application Discontinuation
- 2005-08-09 GT GT200500215A patent/GT200500215A/es unknown
- 2005-08-16 AR ARP050103439A patent/AR051008A1/es unknown
- 2005-08-17 PE PE2005000956A patent/PE20060630A1/es not_active Application Discontinuation
- 2005-08-18 DE DE602005021889T patent/DE602005021889D1/de not_active Expired - Lifetime
- 2005-08-18 RU RU2007109812/04A patent/RU2403257C2/ru not_active IP Right Cessation
- 2005-08-18 PL PL05826812T patent/PL1784409T3/pl unknown
- 2005-08-18 EP EP05826812A patent/EP1784409B1/en not_active Expired - Lifetime
- 2005-08-18 MY MYPI20053879A patent/MY139831A/en unknown
- 2005-08-18 WO PCT/US2005/029383 patent/WO2006021000A2/en not_active Ceased
- 2005-08-18 JP JP2007528007A patent/JP4869232B2/ja not_active Expired - Fee Related
- 2005-08-18 BR BRPI0514419-1A patent/BRPI0514419A/pt not_active Application Discontinuation
- 2005-08-18 ES ES05826812T patent/ES2347166T3/es not_active Expired - Lifetime
- 2005-08-18 PT PT05826812T patent/PT1784409E/pt unknown
- 2005-08-18 AT AT05826812T patent/ATE471326T1/de active
- 2005-08-18 CN CNB2005800269958A patent/CN100562521C/zh not_active Expired - Fee Related
- 2005-08-18 AU AU2005272584A patent/AU2005272584B2/en not_active Ceased
- 2005-08-18 CA CA2577879A patent/CA2577879C/en not_active Expired - Fee Related
- 2005-08-18 KR KR1020077003865A patent/KR20070045263A/ko not_active Abandoned
- 2005-08-18 DK DK05826812.9T patent/DK1784409T3/da active
- 2005-08-18 RS RSP-2010/0401A patent/RS51413B/sr unknown
- 2005-08-18 HR HR20100475T patent/HRP20100475T1/hr unknown
- 2005-08-18 SI SI200531094T patent/SI1784409T1/sl unknown
- 2005-08-19 PA PA20058642801A patent/PA8642801A1/es unknown
- 2005-08-19 UY UY29077A patent/UY29077A1/es not_active Application Discontinuation
- 2005-08-19 TW TW094128282A patent/TWI372149B/zh not_active IP Right Cessation
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2007
- 2007-02-04 IL IL181158A patent/IL181158A0/en unknown
- 2007-02-13 US US11/674,349 patent/US7393867B2/en not_active Expired - Lifetime
-
2008
- 2008-05-22 US US12/125,450 patent/US7652046B2/en not_active Expired - Lifetime
-
2010
- 2010-09-09 CY CY20101100823T patent/CY1110775T1/el unknown
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