KR20110093928A - 아릴알킬카르바메이트 유도체, 그의 제조 방법 및 치료학에서의 그의 용도 - Google Patents
아릴알킬카르바메이트 유도체, 그의 제조 방법 및 치료학에서의 그의 용도 Download PDFInfo
- Publication number
- KR20110093928A KR20110093928A KR1020117015377A KR20117015377A KR20110093928A KR 20110093928 A KR20110093928 A KR 20110093928A KR 1020117015377 A KR1020117015377 A KR 1020117015377A KR 20117015377 A KR20117015377 A KR 20117015377A KR 20110093928 A KR20110093928 A KR 20110093928A
- Authority
- KR
- South Korea
- Prior art keywords
- phenyl
- alkyl
- ethylcarbamate
- group
- optionally substituted
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title abstract description 16
- 239000003814 drug Substances 0.000 title description 10
- 238000002360 preparation method Methods 0.000 title description 5
- -1 biphenylyl Chemical group 0.000 claims abstract description 199
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 40
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 11
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract description 11
- 125000002757 morpholinyl group Chemical group 0.000 abstract description 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract description 11
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract description 10
- KKYIEPKFJPKUCK-UHFFFAOYSA-N 2,2,2-trifluoroethyl n-benzylcarbamate Chemical compound FC(F)(F)COC(=O)NCC1=CC=CC=C1 KKYIEPKFJPKUCK-UHFFFAOYSA-N 0.000 abstract description 10
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract description 10
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 abstract description 10
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 abstract description 10
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 abstract description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract description 10
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 abstract description 10
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 abstract description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract description 10
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 abstract description 10
- 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 abstract description 10
- 125000002541 furyl group Chemical group 0.000 abstract description 10
- 125000002883 imidazolyl group Chemical group 0.000 abstract description 10
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract description 10
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 abstract description 10
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 abstract description 10
- 125000001041 indolyl group Chemical group 0.000 abstract description 10
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 abstract description 10
- 125000001786 isothiazolyl group Chemical group 0.000 abstract description 10
- 125000000842 isoxazolyl group Chemical group 0.000 abstract description 10
- 125000001624 naphthyl group Chemical group 0.000 abstract description 10
- 125000002971 oxazolyl group Chemical group 0.000 abstract description 10
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 abstract description 10
- 125000003373 pyrazinyl group Chemical group 0.000 abstract description 10
- 125000003226 pyrazolyl group Chemical group 0.000 abstract description 10
- 125000002098 pyridazinyl group Chemical group 0.000 abstract description 10
- 125000004076 pyridyl group Chemical group 0.000 abstract description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract description 10
- 125000000168 pyrrolyl group Chemical group 0.000 abstract description 10
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 abstract description 10
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 abstract description 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 abstract description 10
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 abstract description 10
- 125000001113 thiadiazolyl group Chemical group 0.000 abstract description 10
- 125000004306 triazinyl group Chemical group 0.000 abstract description 10
- 125000001425 triazolyl group Chemical group 0.000 abstract description 10
- ORMKDOXTVBZIIH-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) n-[(4-bromophenyl)methyl]carbamate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OC(=O)NCC1=CC=C(Br)C=C1 ORMKDOXTVBZIIH-UHFFFAOYSA-N 0.000 abstract description 9
- KCZQJMZEJRESES-UHFFFAOYSA-N (4-cyanophenyl) n-[(4-methoxyphenyl)methyl]carbamate Chemical compound C1=CC(OC)=CC=C1CNC(=O)OC1=CC=C(C#N)C=C1 KCZQJMZEJRESES-UHFFFAOYSA-N 0.000 abstract description 9
- RHQBRRVZUPNXOT-UHFFFAOYSA-N 2,2,2-trifluoroethyl n-[(4-methoxyphenyl)methyl]carbamate Chemical compound COC1=CC=C(CNC(=O)OCC(F)(F)F)C=C1 RHQBRRVZUPNXOT-UHFFFAOYSA-N 0.000 abstract description 9
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 abstract description 9
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract description 9
- LLZADNUQFUMWDF-UHFFFAOYSA-N phenyl n-[(3,4-dichlorophenyl)methyl]carbamate Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC(=O)OC1=CC=CC=C1 LLZADNUQFUMWDF-UHFFFAOYSA-N 0.000 abstract description 9
- BRVIMVMKVQEGJZ-UHFFFAOYSA-N phenyl n-[(3-chlorophenyl)methyl]carbamate Chemical compound ClC1=CC=CC(CNC(=O)OC=2C=CC=CC=2)=C1 BRVIMVMKVQEGJZ-UHFFFAOYSA-N 0.000 abstract description 9
- MUWOBRYEPFTMFS-UHFFFAOYSA-N phenyl n-[(3-nitrophenyl)methyl]carbamate Chemical compound [O-][N+](=O)C1=CC=CC(CNC(=O)OC=2C=CC=CC=2)=C1 MUWOBRYEPFTMFS-UHFFFAOYSA-N 0.000 abstract description 9
- POZVDKJUFVPZTE-UHFFFAOYSA-N phenyl n-[(4-chlorophenyl)methyl]carbamate Chemical compound C1=CC(Cl)=CC=C1CNC(=O)OC1=CC=CC=C1 POZVDKJUFVPZTE-UHFFFAOYSA-N 0.000 abstract description 9
- BOBZFOFRZKZBSH-UHFFFAOYSA-N phenyl n-[(4-methoxyphenyl)methyl]carbamate Chemical compound C1=CC(OC)=CC=C1CNC(=O)OC1=CC=CC=C1 BOBZFOFRZKZBSH-UHFFFAOYSA-N 0.000 abstract description 9
- RBTYEZSXYYODAG-UHFFFAOYSA-N phenyl n-[2-[4-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]carbamate Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1C(C=C1)=CC=C1CCNC(=O)OC1=CC=CC=C1 RBTYEZSXYYODAG-UHFFFAOYSA-N 0.000 abstract description 9
- 239000012453 solvate Substances 0.000 abstract description 9
- 125000000335 thiazolyl group Chemical group 0.000 abstract description 9
- 125000001544 thienyl group Chemical group 0.000 abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 abstract description 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 3
- 239000000194 fatty acid Substances 0.000 abstract description 3
- 229930195729 fatty acid Natural products 0.000 abstract description 3
- 150000004665 fatty acids Chemical class 0.000 abstract description 3
- 150000004677 hydrates Chemical class 0.000 abstract description 3
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 abstract description 3
- 102000004092 Amidohydrolases Human genes 0.000 abstract description 2
- 108090000531 Amidohydrolases Proteins 0.000 abstract description 2
- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 abstract description 2
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 4
- 125000004414 alkyl thio group Chemical group 0.000 abstract 3
- ZXFSQLAVAIODJP-UHFFFAOYSA-N (2,4,5-trichlorophenyl) n-[2-(4-chlorophenyl)ethyl]carbamate Chemical compound C1=CC(Cl)=CC=C1CCNC(=O)OC1=CC(Cl)=C(Cl)C=C1Cl ZXFSQLAVAIODJP-UHFFFAOYSA-N 0.000 abstract 1
- PYKXYOAQGUINKR-UHFFFAOYSA-N (4-chloro-2-nitrophenyl) n-[2-(4-chlorophenyl)ethyl]carbamate Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1OC(=O)NCCC1=CC=C(Cl)C=C1 PYKXYOAQGUINKR-UHFFFAOYSA-N 0.000 abstract 1
- XQJPPIDPGZSDSK-UHFFFAOYSA-N (4-cyanophenyl) n-[2-(4-methylphenyl)ethyl]carbamate Chemical compound C1=CC(C)=CC=C1CCNC(=O)OC1=CC=C(C#N)C=C1 XQJPPIDPGZSDSK-UHFFFAOYSA-N 0.000 abstract 1
- ZZGXWMJVOQXADI-UHFFFAOYSA-N (4-fluorophenyl) n-[2-(4-methoxyphenyl)ethyl]carbamate Chemical compound C1=CC(OC)=CC=C1CCNC(=O)OC1=CC=C(F)C=C1 ZZGXWMJVOQXADI-UHFFFAOYSA-N 0.000 abstract 1
- BXVWSZCHTGEHJU-UHFFFAOYSA-N (4-nitrophenyl) n-[2-(3,4-dimethoxyphenyl)ethyl]carbamate Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)OC1=CC=C([N+]([O-])=O)C=C1 BXVWSZCHTGEHJU-UHFFFAOYSA-N 0.000 abstract 1
- VJKAHDBVHMAWOA-UHFFFAOYSA-N (4-nitrophenyl) n-[2-(4-hydroxyphenyl)ethyl]carbamate Chemical compound C1=CC(O)=CC=C1CCNC(=O)OC1=CC=C([N+]([O-])=O)C=C1 VJKAHDBVHMAWOA-UHFFFAOYSA-N 0.000 abstract 1
- QKYQVQHENBCLEO-UHFFFAOYSA-N (4-nitrophenyl) n-[2-(4-phenylmethoxyphenyl)ethyl]carbamate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)NCCC(C=C1)=CC=C1OCC1=CC=CC=C1 QKYQVQHENBCLEO-UHFFFAOYSA-N 0.000 abstract 1
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
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- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000002111 antiemetic agent Substances 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 229960002708 antigout preparations Drugs 0.000 abstract 1
- 239000003096 antiparasitic agent Substances 0.000 abstract 1
- 239000000939 antiparkinson agent Substances 0.000 abstract 1
- 239000003435 antirheumatic agent Substances 0.000 abstract 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- 239000000824 cytostatic agent Substances 0.000 abstract 1
- 230000001085 cytostatic effect Effects 0.000 abstract 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 239000003176 neuroleptic agent Substances 0.000 abstract 1
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- 230000000324 neuroprotective effect Effects 0.000 abstract 1
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- REERUHWZMHJWGG-UHFFFAOYSA-N phenyl n-[2-(3,4-dimethoxyphenyl)ethyl]carbamate Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)OC1=CC=CC=C1 REERUHWZMHJWGG-UHFFFAOYSA-N 0.000 abstract 1
- BNCYJELNPNIOQQ-UHFFFAOYSA-N phenyl n-[2-(4-thiophen-3-ylphenyl)propyl]carbamate Chemical compound C=1C=C(C2=CSC=C2)C=CC=1C(C)CNC(=O)OC1=CC=CC=C1 BNCYJELNPNIOQQ-UHFFFAOYSA-N 0.000 abstract 1
- DCCBWZOQRKKTRB-UHFFFAOYSA-N phenyl n-[2-[4-(2-amino-1,3-thiazol-4-yl)phenyl]ethyl]carbamate Chemical compound S1C(N)=NC(C=2C=CC(CCNC(=O)OC=3C=CC=CC=3)=CC=2)=C1 DCCBWZOQRKKTRB-UHFFFAOYSA-N 0.000 abstract 1
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 31
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- 239000000126 substance Substances 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
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- RMSPOVPGDBDYKH-UHFFFAOYSA-N (4-phenylphenyl)methanamine Chemical compound C1=CC(CN)=CC=C1C1=CC=CC=C1 RMSPOVPGDBDYKH-UHFFFAOYSA-N 0.000 description 6
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| FR0311615 | 2003-10-03 |
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| FR2864080B1 (fr) * | 2003-12-23 | 2006-02-03 | Sanofi Synthelabo | Derives de 1-piperazine-et-1-homopiperazine-carboxylates, leur preparation et leur application en therapeutique |
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| FR2885364B1 (fr) * | 2005-05-03 | 2007-06-29 | Sanofi Aventis Sa | Derives d'alkyl-, alkenyl-et alkynylcarbamates, leur preparation et leur application en therapeutique |
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| US8207226B1 (en) | 2008-06-03 | 2012-06-26 | Alcon Research, Ltd. | Use of FAAH antagonists for treating dry eye and ocular pain |
| WO2012058115A2 (en) | 2010-10-28 | 2012-05-03 | Benjamin Cravatt | Anti-cancer serine hydrolase inhibitory carbamates |
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| CN105418460B (zh) * | 2014-08-11 | 2017-04-12 | 苏州鹏旭医药科技有限公司 | 匹莫范色林及其类似化合物中间体,其制备方法和制备匹莫范色林及其类似化合物的方法 |
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| AU2017235461B2 (en) | 2016-03-15 | 2023-02-23 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion |
| KR101978364B1 (ko) * | 2017-06-15 | 2019-05-14 | 크리스탈지노믹스(주) | 알킬카바모일 나프탈렌일옥시 옥테노일 하이드록시아마이드 또는 그 유도체의 약학적으로 허용 가능한 염 및 그 제조방법 |
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| JPS4939815A (enExample) | 1972-08-23 | 1974-04-13 | ||
| DE2326754C3 (de) | 1973-05-25 | 1978-04-20 | Eisenwerk-Gesellschaft Maximilianshuette Mbh, 8458 Sulzbach-Rosenberg | Vorrichtung zum gesteuerten Zuführen eines Frischgases und eines fluiden Schutzmediums |
| JPS531333A (en) | 1976-06-04 | 1978-01-09 | Matsushita Electric Ind Co Ltd | Seath heater |
| JPS56103222A (en) * | 1980-01-22 | 1981-08-18 | Mitsui Toatsu Chem Inc | Preparation of polyurethane |
| SU1363772A1 (ru) * | 1985-07-23 | 2000-02-27 | Уфимский Нефтяной Институт | Способ получения изопропил-n-фенилкарбамата |
| DE3815046A1 (de) * | 1988-05-04 | 1989-11-16 | Basf Ag | 3-chlor-2-methylphenethylaminoderivate |
| IL95994A0 (en) * | 1989-11-15 | 1991-07-18 | American Home Prod | Carbamate esters and pharmaceutical compositions containing them |
| US5112859A (en) * | 1990-09-14 | 1992-05-12 | American Home Products Corporation | Biphenyl amide cholesterol ester hydrolase inhibitors |
| ES2087038B1 (es) * | 1994-11-07 | 1997-03-16 | Uriach & Cia Sa J | Nuevas piperidinas con actividad antagonista del paf. |
| TW375612B (en) * | 1995-04-06 | 1999-12-01 | Janssen Pharmaceutica Nv | 1,3-dihydro-2H-imidazol-2-one derivatives for the treatment of disease states related to an abnormal enzymatic or catalytic activity of phosphodiesterase type IV, preparation thereof and pharmaceutical composition containing the same |
| US5756507A (en) * | 1995-12-14 | 1998-05-26 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
| EP0868178A4 (en) * | 1995-12-14 | 2000-03-29 | Merck & Co Inc | GONADOTROPIN RELEASING HORMON ANTAGONISTS |
| BR9612435A (pt) * | 1995-12-29 | 1999-07-13 | Boehringer Ingelheim Pharamceu | Derivados de fenil tiazol com propreidades anti-herpes |
| US6143917A (en) * | 1997-02-14 | 2000-11-07 | Ube Industries, Ltd. | Process for producing aryl carbamates |
| JP3480296B2 (ja) * | 1997-02-14 | 2003-12-15 | 宇部興産株式会社 | カルバメートの製造方法 |
| JP3453360B2 (ja) * | 1998-02-09 | 2003-10-06 | エルパトローニク アクチエンゲゼルシヤフト | 搬送装置 |
| PE20000942A1 (es) * | 1998-07-31 | 2000-09-28 | Lilly Co Eli | Derivados de amida, carbamato y urea |
| US7183319B2 (en) * | 2000-07-26 | 2007-02-27 | Patrick Anthony Riley | Phenylethylamine derivatives and their use in the treatment of melanoma |
| HN2001000224A (es) * | 2000-10-19 | 2002-06-13 | Pfizer | Compuestos de imidazol condensado con arilo o heteroarilo como agentes anti - inflamatorios y analgesicos. |
| PL373970A1 (en) * | 2002-02-08 | 2005-09-19 | Bristol-Myers Squibb Company | (oxime)carbamoyl fatty acid amide hydrolase inhibitors |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
-
2003
- 2003-10-03 FR FR0311615A patent/FR2860514A1/fr not_active Withdrawn
-
2004
- 2004-10-01 EP EP08012005A patent/EP1972616A1/fr not_active Withdrawn
- 2004-10-01 SG SG200800743-7A patent/SG139760A1/en unknown
- 2004-10-01 BR BRPI0414855-0A patent/BRPI0414855A/pt not_active IP Right Cessation
- 2004-10-01 RS YUP-2006/0239A patent/RS20060239A/sr unknown
- 2004-10-01 RU RU2006114700/04A patent/RU2400472C2/ru not_active IP Right Cessation
- 2004-10-01 JP JP2006530410A patent/JP4822351B2/ja not_active Expired - Fee Related
- 2004-10-01 AU AU2004277436A patent/AU2004277436B2/en not_active Ceased
- 2004-10-01 WO PCT/FR2004/002486 patent/WO2005033066A2/fr not_active Ceased
- 2004-10-01 EP EP04817093A patent/EP1673337B1/fr not_active Expired - Lifetime
- 2004-10-01 CN CN2004800327944A patent/CN1878750B/zh not_active Expired - Fee Related
- 2004-10-01 ME MEP-306/08A patent/MEP30608A/xx unknown
- 2004-10-01 KR KR1020117015377A patent/KR20110093928A/ko not_active Ceased
- 2004-10-01 KR KR1020067006449A patent/KR20060100373A/ko not_active Ceased
- 2004-10-01 MX MXPA06003751A patent/MXPA06003751A/es active IP Right Grant
- 2004-10-01 AT AT04817093T patent/ATE534621T1/de active
- 2004-10-01 NZ NZ546309A patent/NZ546309A/en not_active IP Right Cessation
- 2004-10-01 CA CA002539849A patent/CA2539849A1/fr not_active Abandoned
-
2006
- 2006-03-26 IL IL174555A patent/IL174555A0/en unknown
- 2006-03-27 MA MA28890A patent/MA28074A1/fr unknown
- 2006-03-31 US US11/395,942 patent/US7696374B2/en not_active Expired - Fee Related
- 2006-05-03 NO NO20061982A patent/NO20061982L/no not_active Application Discontinuation
-
2011
- 2011-03-08 AU AU2011201012A patent/AU2011201012B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2539849A1 (fr) | 2005-04-14 |
| KR20060100373A (ko) | 2006-09-20 |
| AU2011201012B2 (en) | 2011-12-15 |
| NO20061982L (no) | 2006-07-03 |
| JP2007507474A (ja) | 2007-03-29 |
| SG139760A1 (en) | 2008-02-29 |
| WO2005033066A3 (fr) | 2006-05-11 |
| FR2860514A1 (fr) | 2005-04-08 |
| NZ546309A (en) | 2010-01-29 |
| IL174555A0 (en) | 2006-08-20 |
| EP1673337A2 (fr) | 2006-06-28 |
| RS20060239A (sr) | 2008-06-05 |
| WO2005033066A2 (fr) | 2005-04-14 |
| US7696374B2 (en) | 2010-04-13 |
| RU2006114700A (ru) | 2007-11-20 |
| AU2004277436A1 (en) | 2005-04-14 |
| JP4822351B2 (ja) | 2011-11-24 |
| ATE534621T1 (de) | 2011-12-15 |
| MEP30608A (en) | 2010-10-10 |
| RU2400472C2 (ru) | 2010-09-27 |
| AU2011201012A1 (en) | 2011-03-31 |
| EP1673337B1 (fr) | 2011-11-23 |
| EP1972616A1 (fr) | 2008-09-24 |
| BRPI0414855A (pt) | 2006-11-21 |
| HK1097250A1 (en) | 2007-06-22 |
| AU2004277436B2 (en) | 2011-04-14 |
| US20060223805A1 (en) | 2006-10-05 |
| CN1878750A (zh) | 2006-12-13 |
| CN1878750B (zh) | 2011-04-20 |
| MXPA06003751A (es) | 2006-06-23 |
| MA28074A1 (fr) | 2006-08-01 |
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