KR20130047765A - 세로토닌 수용체 조절제로서의 트리사이클릭 인데노-피롤 유도체 - Google Patents
세로토닌 수용체 조절제로서의 트리사이클릭 인데노-피롤 유도체 Download PDFInfo
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- KR20130047765A KR20130047765A KR1020137007788A KR20137007788A KR20130047765A KR 20130047765 A KR20130047765 A KR 20130047765A KR 1020137007788 A KR1020137007788 A KR 1020137007788A KR 20137007788 A KR20137007788 A KR 20137007788A KR 20130047765 A KR20130047765 A KR 20130047765A
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- KR
- South Korea
- Prior art keywords
- mmol
- methyl
- pyrrole
- hexahydroindeno
- calcd
- 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.)
- Withdrawn
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- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title abstract description 7
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 title abstract description 6
- CNAFOLPGHNAMBW-UHFFFAOYSA-N indeno[2,1-b]pyrrole Chemical class C1=CC=CC2=CC3=NC=CC3=C21 CNAFOLPGHNAMBW-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 10
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- 235000020824 obesity Nutrition 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 206010012335 Dependence Diseases 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Chemical group 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
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- 238000000034 method Methods 0.000 description 35
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
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- 239000000706 filtrate Substances 0.000 description 20
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- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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- 239000012267 brine Substances 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
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- 239000003795 chemical substances by application Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
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- 102000005962 receptors Human genes 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- MGRSFLYKZQNIIA-UHFFFAOYSA-N 6-chloro-4-methyl-1,2,3,3a,4,8b-hexahydroindeno[1,2-c]pyrrol-7-ol;ethylcarbamic acid Chemical compound CCNC(O)=O.C12=CC(O)=C(Cl)C=C2C(C)C2C1CNC2 MGRSFLYKZQNIIA-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000002502 liposome Substances 0.000 description 6
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- 238000004366 reverse phase liquid chromatography Methods 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 239000003643 water by type Substances 0.000 description 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
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- 229920006395 saturated elastomer Polymers 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 4
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- 125000004122 cyclic group Chemical group 0.000 description 4
- AFWNYNAYRQBJIV-UHFFFAOYSA-N cyclopenta[a]indene Chemical compound C1=CC=C2C3=CC=CC3=CC2=C1 AFWNYNAYRQBJIV-UHFFFAOYSA-N 0.000 description 4
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- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- PPOWAGATRAVSPP-UHFFFAOYSA-N 1,2,3,8,8a,8b-hexahydroindeno[1,2-c]pyrrole Chemical compound C1=CCC2C3CNCC3=CC2=C1 PPOWAGATRAVSPP-UHFFFAOYSA-N 0.000 description 3
- TUJZGEXAAMUMLD-UHFFFAOYSA-N 6-bromo-7-methoxy-4-methyl-1,2,3,3a,4,8b-hexahydroindeno[1,2-c]pyrrole;ethylcarbamic acid Chemical compound CCNC(O)=O.C1=C(Br)C(OC)=CC2=C1C(C)C1CNCC12 TUJZGEXAAMUMLD-UHFFFAOYSA-N 0.000 description 3
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- PBNAJYXMDIZSKB-UHFFFAOYSA-N tert-butylcarbamic acid;6-(2,6-difluorophenyl)-1,2,3,3a,4,8b-hexahydroindeno[1,2-c]pyrrole Chemical compound CC(C)(C)NC(O)=O.FC1=CC=CC(F)=C1C1=CC=C(C2C(CNC2)C2)C2=C1 PBNAJYXMDIZSKB-UHFFFAOYSA-N 0.000 description 1
- SNFCSIFAOGEHIG-UHFFFAOYSA-N tert-butylcarbamic acid;6-chloro-1,2,3,3a,4,8b-hexahydroindeno[1,2-c]pyrrole Chemical compound CC(C)(C)NC(O)=O.C1C2=CC(Cl)=CC=C2C2C1CNC2 SNFCSIFAOGEHIG-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical group CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical group C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
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- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
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- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
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- 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
-
- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P25/20—Hypnotics; Sedatives
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
- C07D209/56—Ring systems containing three or more rings
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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- Medicinal Chemistry (AREA)
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- Engineering & Computer Science (AREA)
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- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Addiction (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| US60/592,047 | 2004-07-29 | ||
| PCT/US2005/026415 WO2007081299A2 (en) | 2004-07-29 | 2005-07-26 | Tricyclic indeno-pyrrole derivatives as serotonin receptor modulators |
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| US20060025601A1 (en) | 2004-07-29 | 2006-02-02 | Athersys, Inc. | Tricyclic indeno-pyrrole derivatives as serotonin receptor modulators |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| JP4866901B2 (ja) | 2007-02-07 | 2012-02-01 | 協和発酵キリン株式会社 | ３環系化合物 |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| WO2009097995A1 (de) * | 2008-02-07 | 2009-08-13 | Sanofi-Aventis | Neue phenyl-substituierte imidazolidine, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP3081213B1 (en) | 2008-08-06 | 2020-04-01 | Kyowa Kirin Co., Ltd. | Tricyclic compound |
| TW201041851A (en) | 2009-03-10 | 2010-12-01 | Organon Nv | Tricyclic heterocyclic derivatives |
| WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| CN106380440B (zh) * | 2016-08-30 | 2019-02-01 | 华东师范大学 | 一种茚酮并吡咯类衍生物及其合成方法和应用 |
| CN106631989B (zh) * | 2016-11-26 | 2019-07-16 | 威海迪素制药有限公司 | 一种盐酸多奈哌齐有关物质e的制备方法 |
| WO2019131902A1 (ja) | 2017-12-27 | 2019-07-04 | 武田薬品工業株式会社 | 腹圧性尿失禁および便失禁の治療薬 |
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| DE3576334D1 (de) * | 1984-07-25 | 1990-04-12 | Abbott Lab | 1,2,3,3a,8,8a-hexahydro-indeno-(1,2-c)pyrrde. |
| US4622405A (en) * | 1984-07-25 | 1986-11-11 | Abbott Laboratories | 1,2,3,3a,8,8a-hexahydro-indeno[1,2-c]pyrroles useful in the treatment of hypertension |
| EP0422134B1 (en) * | 1988-12-15 | 1996-06-12 | Abbott Laboratories | 5-ht selective agents |
| US5049564A (en) * | 1989-11-17 | 1991-09-17 | Abbott Laboratories | 5-HT selective agents |
| US5244888A (en) * | 1989-11-17 | 1993-09-14 | Abbott Laboratories | 5-HT selective agents |
| TW334423B (en) * | 1993-10-22 | 1998-06-21 | Hoffmann La Roche | Tricyclic 1-aminoethylpyrrole-derivatives |
| US7351711B2 (en) * | 2003-07-31 | 2008-04-01 | Janssen Pharmaceutical, N.V. | Tricyclic indanyls as integrin inhibitors |
| TWI350168B (en) * | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| US20060025601A1 (en) * | 2004-07-29 | 2006-02-02 | Athersys, Inc. | Tricyclic indeno-pyrrole derivatives as serotonin receptor modulators |
-
2005
- 2005-07-26 US US11/189,952 patent/US20060025601A1/en not_active Abandoned
- 2005-07-26 JP JP2007554065A patent/JP4990164B2/ja not_active Expired - Fee Related
- 2005-07-26 KR KR1020137007788A patent/KR20130047765A/ko not_active Withdrawn
- 2005-07-26 CA CA2603249A patent/CA2603249C/en not_active Expired - Fee Related
- 2005-07-26 RU RU2007107494/04A patent/RU2007107494A/ru not_active Application Discontinuation
- 2005-07-26 NZ NZ552806A patent/NZ552806A/en not_active IP Right Cessation
- 2005-07-26 KR KR1020077002230A patent/KR101257233B1/ko not_active Expired - Fee Related
- 2005-07-26 AU AU2005333518A patent/AU2005333518B2/en not_active Ceased
- 2005-07-26 CN CNA2005800255071A patent/CN101516372A/zh active Pending
- 2005-07-26 WO PCT/US2005/026415 patent/WO2007081299A2/en not_active Ceased
- 2005-07-26 EP EP05858534A patent/EP1841738A4/en not_active Withdrawn
- 2005-07-26 BR BRPI0512869-2A patent/BRPI0512869A/pt not_active Application Discontinuation
- 2005-07-28 AR ARP050103146A patent/AR050274A1/es not_active Application Discontinuation
- 2005-07-29 TW TW094125988A patent/TWI377195B/zh not_active IP Right Cessation
-
2007
- 2007-01-24 ZA ZA200700684A patent/ZA200700684B/xx unknown
- 2007-01-25 IL IL180977A patent/IL180977A/en not_active IP Right Cessation
- 2007-02-27 NO NO20071102A patent/NO20071102L/no not_active Application Discontinuation
-
2009
- 2009-06-04 US US12/478,362 patent/US7935830B2/en not_active Expired - Fee Related
-
2011
- 2011-03-25 US US13/071,732 patent/US8232311B2/en not_active Expired - Fee Related
-
2012
- 2012-06-18 US US13/526,249 patent/US8716324B2/en not_active Expired - Fee Related
-
2014
- 2014-03-21 US US14/221,809 patent/US9096520B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU2005333518B2 (en) | 2010-12-02 |
| NO20071102L (no) | 2007-04-20 |
| KR20080025657A (ko) | 2008-03-21 |
| US20090239925A1 (en) | 2009-09-24 |
| AR050274A1 (es) | 2006-10-11 |
| TW200619196A (en) | 2006-06-16 |
| CN101516372A (zh) | 2009-08-26 |
| AU2005333518A1 (en) | 2007-02-22 |
| US8716324B2 (en) | 2014-05-06 |
| EP1841738A4 (en) | 2010-06-02 |
| KR101257233B1 (ko) | 2013-04-29 |
| TWI377195B (en) | 2012-11-21 |
| US7935830B2 (en) | 2011-05-03 |
| US20110172283A1 (en) | 2011-07-14 |
| BRPI0512869A (pt) | 2008-04-08 |
| ZA200700684B (en) | 2008-10-29 |
| WO2007081299A3 (en) | 2007-09-20 |
| NZ552806A (en) | 2009-09-25 |
| JP4990164B2 (ja) | 2012-08-01 |
| US20060025601A1 (en) | 2006-02-02 |
| IL180977A (en) | 2012-08-30 |
| US20140206739A1 (en) | 2014-07-24 |
| RU2007107494A (ru) | 2008-09-10 |
| CA2603249A1 (en) | 2007-07-19 |
| JP2008508365A (ja) | 2008-03-21 |
| US20120252859A1 (en) | 2012-10-04 |
| US8232311B2 (en) | 2012-07-31 |
| CA2603249C (en) | 2014-01-21 |
| US9096520B2 (en) | 2015-08-04 |
| EP1841738A2 (en) | 2007-10-10 |
| WO2007081299A2 (en) | 2007-07-19 |
| AU2005333518A8 (en) | 2008-08-07 |
| IL180977A0 (en) | 2009-02-11 |
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