JP2007526264A5 - - Google Patents
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- Publication number
- JP2007526264A5 JP2007526264A5 JP2007501151A JP2007501151A JP2007526264A5 JP 2007526264 A5 JP2007526264 A5 JP 2007526264A5 JP 2007501151 A JP2007501151 A JP 2007501151A JP 2007501151 A JP2007501151 A JP 2007501151A JP 2007526264 A5 JP2007526264 A5 JP 2007526264A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- amino
- salt
- tert
- compound
- 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.)
- Granted
Links
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 51
- 150000003839 salts Chemical class 0.000 claims 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 38
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 34
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 33
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 32
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000002904 solvent Substances 0.000 claims 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 21
- 229910052757 nitrogen Inorganic materials 0.000 claims 21
- 229910052760 oxygen Inorganic materials 0.000 claims 21
- 239000001301 oxygen Substances 0.000 claims 21
- 229910052717 sulfur Inorganic materials 0.000 claims 21
- 239000011593 sulfur Substances 0.000 claims 21
- 125000005842 heteroatom Chemical group 0.000 claims 20
- 238000000034 method Methods 0.000 claims 19
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 19
- 239000002243 precursor Substances 0.000 claims 17
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims 16
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 14
- BNBPIAMMLAHLAM-UHFFFAOYSA-N (3-pyridin-4-ylphenyl)methanamine Chemical compound NCC1=CC=CC(C=2C=CN=CC=2)=C1 BNBPIAMMLAHLAM-UHFFFAOYSA-N 0.000 claims 11
- 239000003054 catalyst Substances 0.000 claims 11
- -1 triethylsilyl Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims 10
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 8
- 125000001246 bromo group Chemical group Br* 0.000 claims 7
- 229910052763 palladium Inorganic materials 0.000 claims 7
- 125000002346 iodo group Chemical group I* 0.000 claims 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 5
- 239000002585 base Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- YVTQHZDUDUCGRD-UHFFFAOYSA-N 5-bromofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)O1 YVTQHZDUDUCGRD-UHFFFAOYSA-N 0.000 claims 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 239000012046 mixed solvent Substances 0.000 claims 4
- 229910052697 platinum Inorganic materials 0.000 claims 4
- 150000003512 tertiary amines Chemical class 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- RAKGDCXLJFDTKO-UHFFFAOYSA-N 4-[3-(aminomethyl)phenyl]-1-benzylpiperidin-4-ol Chemical compound NCC1=CC=CC(C2(O)CCN(CC=3C=CC=CC=3)CC2)=C1 RAKGDCXLJFDTKO-UHFFFAOYSA-N 0.000 claims 3
- UKRYIKCRRFOEOD-UHFFFAOYSA-N 5-iodofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(I)O1 UKRYIKCRRFOEOD-UHFFFAOYSA-N 0.000 claims 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 3
- HLYLGGIAMXYWHO-UHFFFAOYSA-N [3-(1-benzyl-3,6-dihydro-2h-pyridin-4-yl)phenyl]methanamine Chemical compound NCC1=CC=CC(C=2CCN(CC=3C=CC=CC=3)CC=2)=C1 HLYLGGIAMXYWHO-UHFFFAOYSA-N 0.000 claims 3
- 150000008282 halocarbons Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- VARANPDDBJNTFG-UHFFFAOYSA-N n-[(3-pyridin-4-ylphenyl)methylidene]hydroxylamine Chemical compound ON=CC1=CC=CC(C=2C=CN=CC=2)=C1 VARANPDDBJNTFG-UHFFFAOYSA-N 0.000 claims 3
- MRFONSPCWQUCAX-UHFFFAOYSA-N tert-butyl n-[(3-piperidin-4-ylphenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(C2CCNCC2)=C1 MRFONSPCWQUCAX-UHFFFAOYSA-N 0.000 claims 3
- RKAWSCANUCNZGE-UHFFFAOYSA-N tert-butyl n-[(3-pyridin-4-ylphenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(C=2C=CN=CC=2)=C1 RKAWSCANUCNZGE-UHFFFAOYSA-N 0.000 claims 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- QGJCZJHFJUXQPY-UHFFFAOYSA-N 1-benzyl-4-[3-[(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)methyl]phenyl]piperidin-4-ol Chemical compound C[Si]1(C)CC[Si](C)(C)N1CC1=CC=CC(C2(O)CCN(CC=3C=CC=CC=3)CC2)=C1 QGJCZJHFJUXQPY-UHFFFAOYSA-N 0.000 claims 2
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 claims 2
- YFPQIXUNBPQKQR-UHFFFAOYSA-N 1-ethynyl-2-fluorobenzene Chemical compound FC1=CC=CC=C1C#C YFPQIXUNBPQKQR-UHFFFAOYSA-N 0.000 claims 2
- LLJRXVHJOJRCSM-UHFFFAOYSA-N 3-pyridin-4-yl-1H-indole Chemical group C=1NC2=CC=CC=C2C=1C1=CC=NC=C1 LLJRXVHJOJRCSM-UHFFFAOYSA-N 0.000 claims 2
- QLVNUZPODFIOGC-UHFFFAOYSA-N 5-bromofuran-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Br)O1 QLVNUZPODFIOGC-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical compound C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims 2
- FTLQSQQQFMZPKO-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-[5-[2-(2-fluorophenyl)ethynyl]furan-2-yl]methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2OC(=CC=2)C#CC=2C(=CC=CC=2)F)=C1 FTLQSQQQFMZPKO-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 2
- VGQOKOYKFDUPPJ-UHFFFAOYSA-N chloro-[2-[chloro(dimethyl)silyl]ethyl]-dimethylsilane Chemical compound C[Si](C)(Cl)CC[Si](C)(C)Cl VGQOKOYKFDUPPJ-UHFFFAOYSA-N 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 150000004678 hydrides Chemical class 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- DNWGNGATLVWMOU-UHFFFAOYSA-N n-benzyl-n-piperidin-1-ylhydroxylamine Chemical compound C1CCCCN1N(O)CC1=CC=CC=C1 DNWGNGATLVWMOU-UHFFFAOYSA-N 0.000 claims 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- 150000002923 oximes Chemical class 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- NDIAZHHZQDSVBJ-UHFFFAOYSA-N tert-butyl n-[[3-(1-benzyl-3,6-dihydro-2h-pyridin-4-yl)phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(C=2CCN(CC=3C=CC=CC=3)CC=2)=C1 NDIAZHHZQDSVBJ-UHFFFAOYSA-N 0.000 claims 2
- KQYRKAUORDFEOC-UHFFFAOYSA-N tert-butyl n-[[3-[1-[5-[2-(2-fluorophenyl)ethynyl]furan-2-carbonyl]piperidin-4-yl]phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(C2CCN(CC2)C(=O)C=2OC(=CC=2)C#CC=2C(=CC=CC=2)F)=C1 KQYRKAUORDFEOC-UHFFFAOYSA-N 0.000 claims 2
- FWOBBEOKTITUHK-UHFFFAOYSA-N tert-butyl n-benzylcarbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC=C1 FWOBBEOKTITUHK-UHFFFAOYSA-N 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims 2
- UGEQUCUBWNAUJS-UHFFFAOYSA-N (3-bromophenyl)methanamine;hydrochloride Chemical compound Cl.NCC1=CC=CC(Br)=C1 UGEQUCUBWNAUJS-UHFFFAOYSA-N 0.000 claims 1
- BUNFDZZVLUCBGM-UHFFFAOYSA-N 1,2,5-azadisilolidine Chemical compound C1C[SiH2]N[SiH2]1 BUNFDZZVLUCBGM-UHFFFAOYSA-N 0.000 claims 1
- DLLSDZVFKPSBOG-UHFFFAOYSA-N 1-[(3-bromophenyl)methyl]-2,2,5,5-tetramethyl-1,2,5-azadisilolidine Chemical compound C[Si]1(C)CC[Si](C)(C)N1CC1=CC=CC(Br)=C1 DLLSDZVFKPSBOG-UHFFFAOYSA-N 0.000 claims 1
- AUWXDKOYCROSFW-UHFFFAOYSA-N 1-[(3-iodophenyl)methyl]-2,2,5,5-tetramethyl-1,2,5-azadisilolidine Chemical compound C[Si]1(C)CC[Si](C)(C)N1CC1=CC=CC(I)=C1 AUWXDKOYCROSFW-UHFFFAOYSA-N 0.000 claims 1
- ANVUAAJNQXEBNM-UHFFFAOYSA-N 3-pyridin-4-ylbenzaldehyde Chemical compound O=CC1=CC=CC(C=2C=CN=CC=2)=C1 ANVUAAJNQXEBNM-UHFFFAOYSA-N 0.000 claims 1
- OGSJPFDYGHOODD-UHFFFAOYSA-N 3-pyridin-4-ylbenzonitrile Chemical compound N#CC1=CC=CC(C=2C=CN=CC=2)=C1 OGSJPFDYGHOODD-UHFFFAOYSA-N 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- PYFDZOCGFHIRST-UHFFFAOYSA-N hydron;(3-iodophenyl)methanamine;chloride Chemical compound Cl.NCC1=CC=CC(I)=C1 PYFDZOCGFHIRST-UHFFFAOYSA-N 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- AODABXYUAWMHSX-UHFFFAOYSA-N tert-butyl n-[[3-[1-(5-bromofuran-2-carbonyl)piperidin-4-yl]phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(C2CCN(CC2)C(=O)C=2OC(Br)=CC=2)=C1 AODABXYUAWMHSX-UHFFFAOYSA-N 0.000 claims 1
- BPNISPBQIJAMSV-CKIAUBSUSA-N C/C=C(\c1ccc(C#Cc2ccccc2F)[o]1)/N(CC1)CCC1c1cccc(CN)c1 Chemical compound C/C=C(\c1ccc(C#Cc2ccccc2F)[o]1)/N(CC1)CCC1c1cccc(CN)c1 BPNISPBQIJAMSV-CKIAUBSUSA-N 0.000 description 1
- 0 CC1(*)C=C(CN2S(C)(C)CC[Si]2(C)C)C=C(C2(CCN(Cc3ccccc3)CC2)O)C=C1 Chemical compound CC1(*)C=C(CN2S(C)(C)CC[Si]2(C)C)C=C(C2(CCN(Cc3ccccc3)CC2)O)C=C1 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04004799A EP1571150A1 (en) | 2004-03-02 | 2004-03-02 | Process for the preparation of tryptase inhibitors |
| EP04004799.5 | 2004-03-02 | ||
| US58574504P | 2004-07-06 | 2004-07-06 | |
| US60/585,745 | 2004-07-06 | ||
| PCT/EP2005/001676 WO2005095385A1 (en) | 2004-03-02 | 2005-02-18 | Process for the preparation of tryptase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007526264A JP2007526264A (ja) | 2007-09-13 |
| JP2007526264A5 true JP2007526264A5 (enExample) | 2008-03-27 |
| JP4851440B2 JP4851440B2 (ja) | 2012-01-11 |
Family
ID=34745976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007501151A Expired - Fee Related JP4851440B2 (ja) | 2004-03-02 | 2005-02-18 | トリプターゼ阻害剤の製造方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20130225825A1 (enExample) |
| EP (2) | EP1571150A1 (enExample) |
| JP (1) | JP4851440B2 (enExample) |
| CN (2) | CN1950362B (enExample) |
| AT (1) | ATE447567T1 (enExample) |
| AU (1) | AU2005229319B2 (enExample) |
| BR (1) | BRPI0508430A (enExample) |
| CA (1) | CA2557391C (enExample) |
| DK (1) | DK1723140T3 (enExample) |
| ES (1) | ES2334245T3 (enExample) |
| NZ (1) | NZ549224A (enExample) |
| PL (1) | PL1723140T3 (enExample) |
| PT (1) | PT1723140E (enExample) |
| RS (1) | RS51144B (enExample) |
| RU (1) | RU2378271C2 (enExample) |
| SI (1) | SI1723140T1 (enExample) |
| TN (1) | TNSN06260A1 (enExample) |
| UA (1) | UA85701C2 (enExample) |
| WO (1) | WO2005095385A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200840566A (en) * | 2006-12-22 | 2008-10-16 | Esteve Labor Dr | Heterocyclyl-substituted-ethylamino-phenyl derivatives, their preparation and use as medicaments |
| CA2706391A1 (en) * | 2007-11-21 | 2009-05-28 | Janssen Pharmaceutica N.V. | Spiropiperidines for use as tryptase inhibitors |
| RS54413B1 (sr) * | 2008-08-22 | 2016-04-28 | Sanofi | [4-(5-aminometil-2-fluoro-fenil)-piperidin-1-il]-[7-fluoro-1-(2-metoksi-etil)-4trifluorometoksi-1h-indol-3-il]metanon kao inhibitor triptaze iz mastocita |
| MY155682A (en) * | 2009-09-24 | 2015-11-13 | Sanofi Aventis Us Llc | Synthesis of (4-fluoro-3-piperidin-4-yl-benzyl)-carbamic acid tert-butyl ester and intermediates thereof |
| CA2785434A1 (en) * | 2009-12-23 | 2011-06-30 | Sanofi | Treatment for inflammatory bowel disease |
| KR20140038527A (ko) | 2011-06-20 | 2014-03-28 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 연충 감염을 치료하기 위한 복소환식 화합물 |
| SG11201402664VA (en) | 2011-11-28 | 2014-06-27 | Du Pont | N- (4 -quinolinylmethyl) sulfonamide derivatives and their use as anthelmintics |
| WO2014099837A1 (en) | 2012-12-18 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Sulfonamide anthelmintics |
| CN111793101B (zh) * | 2020-07-17 | 2022-09-30 | 四川大学 | C-核苷化合物的合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0401166B1 (de) * | 1989-06-01 | 1995-02-22 | Ciba-Geigy Ag | Neue, stickstoffhaltige Titanocene und deren Verwendung |
| US5252753A (en) * | 1991-11-01 | 1993-10-12 | Ortho Pharmaceutical Corporation | Process for the preparation of certain substituted biphenyl tetrazoles and compounds thereof |
| ZA979781B (en) * | 1996-11-14 | 1998-06-08 | Akzo Nobel Nv | Piperidine derivatives. |
| WO1999018053A1 (en) * | 1997-10-02 | 1999-04-15 | The University Of Western Ontario | Preparation of radiolabelled haloaromatics via polymer-bound intermediates |
| US20020045613A1 (en) * | 2000-04-27 | 2002-04-18 | Heinz Pauls | 1-aroyl-piperidinyl benzamidines |
| HU227630B1 (hu) * | 2000-05-22 | 2011-10-28 | Aventis Pharma Inc | Arilmetilamin-származékok triptáz gátlóként való alkalmazásra és ezeket tartalmazó gyógyszerkészítmények |
| WO2004035744A2 (en) * | 2002-10-18 | 2004-04-29 | Biostream, Inc. | Methods for purifying radiolabelled compounds |
| GB0308613D0 (en) * | 2002-12-26 | 2003-05-21 | Aventis Pharma Inc | 4-(3-Aminomethylphenyl) piperidin-1-yl- 5-(2-fluorophenylethynyl) furan-2-yl- methanone as an inhibitor of mast cell tryptase |
-
2004
- 2004-03-02 EP EP04004799A patent/EP1571150A1/en not_active Withdrawn
-
2005
- 2005-02-18 EP EP05779890A patent/EP1723140B1/en not_active Expired - Lifetime
- 2005-02-18 NZ NZ549224A patent/NZ549224A/en not_active IP Right Cessation
- 2005-02-18 AT AT05779890T patent/ATE447567T1/de active
- 2005-02-18 CN CN2005800140491A patent/CN1950362B/zh not_active Expired - Fee Related
- 2005-02-18 DK DK05779890.2T patent/DK1723140T3/da active
- 2005-02-18 RU RU2006134623/04A patent/RU2378271C2/ru not_active IP Right Cessation
- 2005-02-18 CN CN2008101787837A patent/CN101429194B/zh not_active Expired - Fee Related
- 2005-02-18 WO PCT/EP2005/001676 patent/WO2005095385A1/en not_active Ceased
- 2005-02-18 BR BRPI0508430-0A patent/BRPI0508430A/pt not_active IP Right Cessation
- 2005-02-18 SI SI200530896T patent/SI1723140T1/sl unknown
- 2005-02-18 UA UAA200610386A patent/UA85701C2/ru unknown
- 2005-02-18 CA CA2557391A patent/CA2557391C/en not_active Expired - Fee Related
- 2005-02-18 PL PL05779890T patent/PL1723140T3/pl unknown
- 2005-02-18 ES ES05779890T patent/ES2334245T3/es not_active Expired - Lifetime
- 2005-02-18 RS RSP-2009/0532A patent/RS51144B/sr unknown
- 2005-02-18 AU AU2005229319A patent/AU2005229319B2/en not_active Ceased
- 2005-02-18 PT PT05779890T patent/PT1723140E/pt unknown
- 2005-02-18 JP JP2007501151A patent/JP4851440B2/ja not_active Expired - Fee Related
-
2006
- 2006-08-15 TN TNP2006000260A patent/TNSN06260A1/en unknown
-
2013
- 2013-04-11 US US13/861,066 patent/US20130225825A1/en not_active Abandoned
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