NO323538B1 - Nye P2X7-reseptoragonister for bruk i behandling av inflammatoriske, immun- eller kardiovaskulaere sykdommer, fremgangsmate for fremstilling derav, samt farmasoytiske blandinger som inneholder slike. - Google Patents

Nye P2X7-reseptoragonister for bruk i behandling av inflammatoriske, immun- eller kardiovaskulaere sykdommer, fremgangsmate for fremstilling derav, samt farmasoytiske blandinger som inneholder slike. Download PDF

Info

Publication number: NO323538B1
Authority: NO; Norway
Prior art keywords: oxo; piperidin; benzoxazin; nitro; benzamide
Prior art date: 1999-12-17

Application number

NO20022857A

Other languages

English (en)

Norwegian (no)

Other versions

NO20022857L (no

NO20022857D0 (no

Inventor

Garry Pairaudeau

Stephen Thom

Nicholas Kindon

Bryan Roberts

Andrew Baxter

Original Assignee

Astrazeneca Ab

Priority date (The priority date 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 date listed.)

1999-12-17

Filing date

2002-06-14

Publication date

2007-06-04

2002-06-14 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2002-06-14 Publication of NO20022857D0 publication Critical patent/NO20022857D0/no

2002-08-01 Publication of NO20022857L publication Critical patent/NO20022857L/no

2007-06-04 Publication of NO323538B1 publication Critical patent/NO323538B1/no

Links

238000002360 preparation method Methods 0.000 title claims abstract description 6
102100037602 P2X purinoceptor 7 Human genes 0.000 title description 14
101710189965 P2X purinoceptor 7 Proteins 0.000 title description 14
230000002757 inflammatory effect Effects 0.000 title description 3
239000008194 pharmaceutical composition Substances 0.000 title description 3
208000024172 Cardiovascular disease Diseases 0.000 title description 2
208000026278 immune system disease Diseases 0.000 title description 2
208000027866 inflammatory disease Diseases 0.000 title description 2
239000000018 receptor agonist Substances 0.000 title description 2
229940044601 receptor agonist Drugs 0.000 title description 2
239000000203 mixture Substances 0.000 claims abstract description 56
238000000034 method Methods 0.000 claims abstract description 47
239000003814 drug Substances 0.000 claims abstract description 4
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 114
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 113
150000001875 compounds Chemical class 0.000 claims description 78
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 39
-1 nitro, amino Chemical group 0.000 claims description 35
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
239000012453 solvate Substances 0.000 claims description 12
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
235000005152 nicotinamide Nutrition 0.000 claims description 11
239000011570 nicotinamide Substances 0.000 claims description 11
QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims description 11
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
125000000524 functional group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
238000002560 therapeutic procedure Methods 0.000 claims description 5
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
239000005711 Benzoic acid Substances 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
239000002671 adjuvant Substances 0.000 claims description 4
235000010233 benzoic acid Nutrition 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
OSYLNBLYJPTPGS-UHFFFAOYSA-N 5-chloro-6-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]-n-propan-2-ylpyridine-3-carboxamide Chemical compound ClC1=CC(C(=O)NC(C)C)=CN=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 OSYLNBLYJPTPGS-UHFFFAOYSA-N 0.000 claims description 3
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 3
BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
150000004885 piperazines Chemical group 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
RZNWAPCBXNWJGD-UHFFFAOYSA-N 1-[1-[2-nitro-4-(pyrrolidine-1-carbonyl)phenyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C=1C=C(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)C([N+](=O)[O-])=CC=1C(=O)N1CCCC1 RZNWAPCBXNWJGD-UHFFFAOYSA-N 0.000 claims description 2
YYRFAGCHLGXHTC-UHFFFAOYSA-N 2-decylbenzamide Chemical compound CCCCCCCCCCC1=CC=CC=C1C(N)=O YYRFAGCHLGXHTC-UHFFFAOYSA-N 0.000 claims description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 claims description 2
239000007983 Tris buffer Substances 0.000 claims description 2
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000001207 fluorophenyl group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims 3
WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 claims 2
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical compound OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 2
LZOBTPLSTXJCHY-QHCPKHFHSA-N (2s)-n-[3-chloro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]phenyl]-1-methylpyrrolidine-2-carboxamide Chemical compound CN1CCC[C@H]1C(=O)NC(C=C1Cl)=CC=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 LZOBTPLSTXJCHY-QHCPKHFHSA-N 0.000 claims 1
SYZIUAAQNFJPJY-UHFFFAOYSA-N 1,4-dihydro-3,1-benzoxazin-2-one Chemical compound C1=CC=C2COC(=O)NC2=C1 SYZIUAAQNFJPJY-UHFFFAOYSA-N 0.000 claims 1
MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims 1
NNSYJZXONYAQSY-UHFFFAOYSA-N 1-[1-[2-nitro-4-(4-phenylpiperazine-1-carbonyl)phenyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C=1C=C(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)C([N+](=O)[O-])=CC=1C(=O)N(CC1)CCN1C1=CC=CC=C1 NNSYJZXONYAQSY-UHFFFAOYSA-N 0.000 claims 1
KOHDRSJJKVPPJE-UHFFFAOYSA-N 1-[1-[2-nitro-4-(piperidine-1-carbonyl)phenyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C=1C=C(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)C([N+](=O)[O-])=CC=1C(=O)N1CCCCC1 KOHDRSJJKVPPJE-UHFFFAOYSA-N 0.000 claims 1
OKRNBFHZDGTDRX-UHFFFAOYSA-N 2-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(C(F)(F)F)N=C1 OKRNBFHZDGTDRX-UHFFFAOYSA-N 0.000 claims 1
VXCFWVAOLHYIMK-UHFFFAOYSA-N 2-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]-n-(1h-1,2,4-triazol-5-yl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC(F)(F)C1=NC(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)=NC=C1C(=O)NC=1N=CNN=1 VXCFWVAOLHYIMK-UHFFFAOYSA-N 0.000 claims 1
OPUPBQQWLWFCPU-UHFFFAOYSA-N 2-benzylbenzamide Chemical compound NC(=O)C1=CC=CC=C1CC1=CC=CC=C1 OPUPBQQWLWFCPU-UHFFFAOYSA-N 0.000 claims 1
IZRDLZYOQSBCNG-UHFFFAOYSA-N 2-propylbenzamide Chemical compound CCCC1=CC=CC=C1C(N)=O IZRDLZYOQSBCNG-UHFFFAOYSA-N 0.000 claims 1
GZOJTRITAZODJV-UHFFFAOYSA-N 3,1-benzoxazin-2-one Chemical compound C1=CC=CC2=COC(=O)N=C21 GZOJTRITAZODJV-UHFFFAOYSA-N 0.000 claims 1
UUBSFAVWVHVPLZ-UHFFFAOYSA-N 3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]-n-(2,2,2-trifluoroethyl)benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)NCC(F)(F)F)=CC=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 UUBSFAVWVHVPLZ-UHFFFAOYSA-N 0.000 claims 1
SCQHQSYQRKYVGZ-UHFFFAOYSA-N 3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]-n-(2-phenylethyl)benzamide Chemical compound C=1C=C(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)C([N+](=O)[O-])=CC=1C(=O)NCCC1=CC=CC=C1 SCQHQSYQRKYVGZ-UHFFFAOYSA-N 0.000 claims 1
RIKJKWNZUSPCCM-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=C(C(F)(F)F)N=C1 RIKJKWNZUSPCCM-UHFFFAOYSA-N 0.000 claims 1
WQWNOSPCODIUIF-UHFFFAOYSA-N 6-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]-n-propan-2-ylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC(C)C)=CC=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 WQWNOSPCODIUIF-UHFFFAOYSA-N 0.000 claims 1
BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 claims 1
241000009298 Trigla lyra Species 0.000 claims 1
239000001273 butane Substances 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
ZZHIGDVMMRMUED-UHFFFAOYSA-N ethyl 2-[benzyl-[3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzoyl]amino]acetate Chemical compound C=1C=C(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)C([N+]([O-])=O)=CC=1C(=O)N(CC(=O)OCC)CC1=CC=CC=C1 ZZHIGDVMMRMUED-UHFFFAOYSA-N 0.000 claims 1
UULUZKVFVDVAQB-UHFFFAOYSA-N ethyl 3-hydroxy-2-[[3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzoyl]amino]propanoate Chemical compound [O-][N+](=O)C1=CC(C(=O)NC(CO)C(=O)OCC)=CC=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 UULUZKVFVDVAQB-UHFFFAOYSA-N 0.000 claims 1
WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 1
IRMDGDXZCUEQEP-UHFFFAOYSA-N methyl 2-[[3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzoyl]amino]propanoate Chemical compound [O-][N+](=O)C1=CC(C(=O)NC(C)C(=O)OC)=CC=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 IRMDGDXZCUEQEP-UHFFFAOYSA-N 0.000 claims 1
YBAXWGAREOTWGB-UHFFFAOYSA-N n-(1,3-dihydroxy-2-methylpropan-2-yl)-3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)NC(CO)(CO)C)=CC=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 YBAXWGAREOTWGB-UHFFFAOYSA-N 0.000 claims 1
ADHCQBKTGTUVMF-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzamide Chemical compound C=1C=C(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)C([N+](=O)[O-])=CC=1C(=O)NC(CC1)CCN1CC1=CC=CC=C1 ADHCQBKTGTUVMF-UHFFFAOYSA-N 0.000 claims 1
MSQHARAOGZZCLN-UHFFFAOYSA-N n-(1-hydroxy-3-methoxy-1-phenylpropan-2-yl)-3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzamide Chemical compound C=1C=C(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)C([N+]([O-])=O)=CC=1C(=O)NC(COC)C(O)C1=CC=CC=C1 MSQHARAOGZZCLN-UHFFFAOYSA-N 0.000 claims 1
JDZQZEFZYBQDDZ-UHFFFAOYSA-N n-(1-hydroxypropan-2-yl)-2-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N1=C(C(F)(F)F)C(C(=O)NC(CO)C)=CN=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 JDZQZEFZYBQDDZ-UHFFFAOYSA-N 0.000 claims 1
OFSZBKUNMUOVHT-UHFFFAOYSA-N n-(1-methoxypropan-2-yl)-2-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N1=C(C(F)(F)F)C(C(=O)NC(C)COC)=CN=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 OFSZBKUNMUOVHT-UHFFFAOYSA-N 0.000 claims 1
PZARDHQQBIXBBT-UHFFFAOYSA-N n-(4-hydroxycyclohexyl)-2-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound C1CC(O)CCC1NC(=O)C1=CN=C(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)N=C1C(F)(F)F PZARDHQQBIXBBT-UHFFFAOYSA-N 0.000 claims 1
FUIFLLBPJZSFQS-HXUWFJFHSA-N n-[(2r)-1-amino-3-methyl-1-oxobutan-2-yl]-5-chloro-6-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]pyridine-3-carboxamide Chemical compound ClC1=CC(C(=O)N[C@H](C(C)C)C(N)=O)=CN=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 FUIFLLBPJZSFQS-HXUWFJFHSA-N 0.000 claims 1
AYJPKCGDMBBWLE-HSZRJFAPSA-N n-[(2s)-1-hydroxy-3,3-dimethylbutan-2-yl]-3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)N[C@H](CO)C(C)(C)C)=CC=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 AYJPKCGDMBBWLE-HSZRJFAPSA-N 0.000 claims 1
NDXVXJBIZZDGBQ-UHFFFAOYSA-N n-[3-chloro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]phenyl]propane-2-sulfonamide Chemical compound ClC1=CC(NS(=O)(=O)C(C)C)=CC=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 NDXVXJBIZZDGBQ-UHFFFAOYSA-N 0.000 claims 1
COCSAJHZGSBCGS-UHFFFAOYSA-N n-benzyl-3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzamide Chemical compound C=1C=C(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)C([N+](=O)[O-])=CC=1C(=O)NCC1=CC=CC=C1 COCSAJHZGSBCGS-UHFFFAOYSA-N 0.000 claims 1
APUCASVFGWTVTG-UHFFFAOYSA-N n-benzyl-n-butyl-3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzamide Chemical compound C=1C=C(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)C([N+]([O-])=O)=CC=1C(=O)N(CCCC)CC1=CC=CC=C1 APUCASVFGWTVTG-UHFFFAOYSA-N 0.000 claims 1
LKQUCICFTHBFAL-UHFFFAOYSA-N n-benzylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NCC1=CC=CC=C1 LKQUCICFTHBFAL-UHFFFAOYSA-N 0.000 claims 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 1
SRJOCJYGOFTFLH-UHFFFAOYSA-M piperidine-4-carboxylate Chemical compound [O-]C(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-M 0.000 claims 1
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IUSMUDUXMCPTDC-UHFFFAOYSA-N methyl 2-[3-nitro-4-[4-(2-oxo-3,4-dihydroquinolin-1-yl)piperidin-1-yl]benzoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C(C=C1[N+]([O-])=O)=CC=C1N1CCC(N2C3=CC=CC=C3CCC2=O)CC1 IUSMUDUXMCPTDC-UHFFFAOYSA-N 0.000 description 1
LOCJPOYKBUUVKU-UHFFFAOYSA-N methyl 3-amino-4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(N)=C1 LOCJPOYKBUUVKU-UHFFFAOYSA-N 0.000 description 1
RYYMSFBYYAYGOX-UHFFFAOYSA-N methyl 4-chloro-3-cyanobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C#N)=C1 RYYMSFBYYAYGOX-UHFFFAOYSA-N 0.000 description 1
230000002025 microglial effect Effects 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
NUOJFCBXBFNVGR-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)-3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)N(CCO)CCO)=CC=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 NUOJFCBXBFNVGR-UHFFFAOYSA-N 0.000 description 1
RFJRRGVSHTUCHP-UHFFFAOYSA-N n,n-bis(2-hydroxypropyl)-3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)N(CC(C)O)CC(O)C)=CC=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 RFJRRGVSHTUCHP-UHFFFAOYSA-N 0.000 description 1
PNHGJXUQUYNEDG-UHFFFAOYSA-N n-(1-hydroxy-2-methylpropan-2-yl)-2-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N1=C(C(F)(F)F)C(C(=O)NC(C)(CO)C)=CN=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 PNHGJXUQUYNEDG-UHFFFAOYSA-N 0.000 description 1
BTRAIQDGJFZPPX-UHFFFAOYSA-N n-(4-hydroxybutyl)-3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)NCCCCO)=CC=C1N1CCC(N2C3=CC=CC=C3COC2=O)CC1 BTRAIQDGJFZPPX-UHFFFAOYSA-N 0.000 description 1
FVLVBVSILSHUAF-UHFFFAOYSA-N n-benzyl-3,5-dimethyl-n-propan-2-ylbenzamide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N(C(C)C)CC1=CC=CC=C1 FVLVBVSILSHUAF-UHFFFAOYSA-N 0.000 description 1
ZCMIDVDTAKEVKY-UHFFFAOYSA-N n-benzyl-n-ethyl-3-nitro-4-[4-(2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]benzamide Chemical compound C=1C=C(N2CCC(CC2)N2C3=CC=CC=C3COC2=O)C([N+]([O-])=O)=CC=1C(=O)N(CC)CC1=CC=CC=C1 ZCMIDVDTAKEVKY-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000004770 neurodegeneration Effects 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
238000004634 pharmacological analysis method Methods 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 1
239000011148 porous material Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
SJMCLWCCNYAWRQ-UHFFFAOYSA-N propane-2-sulfonamide Chemical compound CC(C)S(N)(=O)=O SJMCLWCCNYAWRQ-UHFFFAOYSA-N 0.000 description 1
OBLVPWTUALCMGD-UHFFFAOYSA-N pyridin-1-ium-3-carboxamide;chloride Chemical compound Cl.NC(=O)C1=CC=CN=C1 OBLVPWTUALCMGD-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
VWSBNWIPICCWAM-UHFFFAOYSA-N tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate Chemical compound CC1CN(C(=O)OC(C)(C)C)CCC1=O VWSBNWIPICCWAM-UHFFFAOYSA-N 0.000 description 1
UJYNCXNRIMDAHV-UHFFFAOYSA-N tert-butyl 4-(4-methyl-2-oxo-4h-3,1-benzoxazin-1-yl)piperidine-1-carboxylate Chemical compound C12=CC=CC=C2C(C)OC(=O)N1C1CCN(C(=O)OC(C)(C)C)CC1 UJYNCXNRIMDAHV-UHFFFAOYSA-N 0.000 description 1
BRTMDLPSCGNGEC-UHFFFAOYSA-N tert-butyl 4-chloro-3-nitrobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 BRTMDLPSCGNGEC-UHFFFAOYSA-N 0.000 description 1
239000012085 test solution Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
208000027185 varicose disease Diseases 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1

Classifications

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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Pulmonology (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Diabetes (AREA)
Neurosurgery (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Anesthesiology (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Emergency Medicine (AREA)
Obesity (AREA)
Hospice & Palliative Care (AREA)
Endocrinology (AREA)
Heart & Thoracic Surgery (AREA)
Psychiatry (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Transplantation (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO20022857A 1999-12-17 2002-06-14 Nye P2X7-reseptoragonister for bruk i behandling av inflammatoriske, immun- eller kardiovaskulaere sykdommer, fremgangsmate for fremstilling derav, samt farmasoytiske blandinger som inneholder slike. NO323538B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE9904652A SE9904652D0 (sv)	1999-12-17	1999-12-17	Novel Compounds
PCT/SE2000/002504 WO2001044213A1 (en)	1999-12-17	2000-12-12	New p2x7 receptor antagonists for use in the treatment of inflammatory, immune or cardiovascular diseases

Publications (3)

Publication Number	Publication Date
NO20022857D0 NO20022857D0 (no)	2002-06-14
NO20022857L NO20022857L (no)	2002-08-01
NO323538B1 true NO323538B1 (no)	2007-06-04

Family

ID=20418188

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20022857A NO323538B1 (no)	1999-12-17	2002-06-14	Nye P2X7-reseptoragonister for bruk i behandling av inflammatoriske, immun- eller kardiovaskulaere sykdommer, fremgangsmate for fremstilling derav, samt farmasoytiske blandinger som inneholder slike.

Country Status (16)

Country	Link
US (1)	US6812226B2 (zh)
EP (1)	EP1242396B1 (zh)
JP (1)	JP2003516978A (zh)
KR (1)	KR20020067554A (zh)
CN (1)	CN1304382C (zh)
AT (1)	ATE250590T1 (zh)
AU (1)	AU775741B2 (zh)
BR (1)	BR0016396A (zh)
CA (1)	CA2392894A1 (zh)
DE (1)	DE60005560T2 (zh)
IL (1)	IL150085A0 (zh)
MX (1)	MXPA02005788A (zh)
NO (1)	NO323538B1 (zh)
SE (1)	SE9904652D0 (zh)
WO (1)	WO2001044213A1 (zh)
ZA (1)	ZA200204429B (zh)

Families Citing this family (71)

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Publication number	Priority date	Publication date	Assignee	Title
SE9904505D0 (sv)	1999-12-09	1999-12-09	Astra Pharma Prod	Novel compounds
TWI258462B (en) *	1999-12-17	2006-07-21	Astrazeneca Ab	Adamantane derivative compounds, process for preparing the same and pharmaceutical composition comprising the same
SE9904738D0 (sv) *	1999-12-22	1999-12-22	Astra Pharma Prod	Novel compounds
EP2172468A1 (en)	2001-04-18	2010-04-07	Euro-Celtique S.A.	Benzimidazolone compounds
EP2033644A1 (en)	2001-04-18	2009-03-11	Euro-Celtique S.A.	Spiroindene and spiroindane compounds
KR100628292B1 (ko)	2001-04-18	2006-09-27	유로-셀티크 소시에떼 아노뉨	스파이로파이라졸 화합물
US6861421B2 (en)	2001-04-18	2005-03-01	Euro-Celtique S.A	Nociceptin analogs
DE60231257D1 (de)	2001-04-18	2009-04-02	Euro Celtique Sa	1-(4-piperidinyl)-1,3-dihydro-2h-indol-2-on derivate und verwandte verbindungen als nociceptin analoge und orl1 liganden zur behandlung von schmerz
WO2003042190A1 (en)	2001-11-12	2003-05-22	Pfizer Products Inc.	N-alkyl-adamantyl derivatives as p2x7-receptor antagonists
PA8557501A1 (es)	2001-11-12	2003-06-30	Pfizer Prod Inc	Benzamida, heteroarilamida y amidas inversas
JP4472349B2 (ja) *	2002-02-12	2010-06-02	スミスクラインビーチャムコーポレーション	ｐ３８阻害薬として有用なニコチンアミド誘導体
US7176310B1 (en)	2002-04-09	2007-02-13	Ucb Sa	Pyrimidinecarboxamide derivatives and their use as anti-inflammatory agents
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2000
- 2000-12-12 KR KR1020027007697A patent/KR20020067554A/ko active IP Right Grant
- 2000-12-12 AT AT00986154T patent/ATE250590T1/de not_active IP Right Cessation
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- 2000-12-12 CN CNB008189234A patent/CN1304382C/zh not_active Expired - Fee Related
- 2000-12-12 BR BR0016396-1A patent/BR0016396A/pt not_active IP Right Cessation
- 2000-12-12 CA CA002392894A patent/CA2392894A1/en not_active Abandoned
- 2000-12-12 EP EP00986154A patent/EP1242396B1/en not_active Expired - Lifetime
- 2000-12-12 US US10/149,760 patent/US6812226B2/en not_active Expired - Fee Related
- 2000-12-12 JP JP2001544703A patent/JP2003516978A/ja active Pending
- 2000-12-12 AU AU22443/01A patent/AU775741B2/en not_active Ceased
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2002
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Publication number	Publication date
AU775741B2 (en)	2004-08-12
NO20022857L (no)	2002-08-01
SE9904652D0 (sv)	1999-12-17
KR20020067554A (ko)	2002-08-22
DE60005560T2 (de)	2004-07-15
US20030040513A1 (en)	2003-02-27
CA2392894A1 (en)	2001-06-21
BR0016396A (pt)	2002-08-20
CN1434811A (zh)	2003-08-06
US6812226B2 (en)	2004-11-02
EP1242396A1 (en)	2002-09-25
CN1304382C (zh)	2007-03-14
ATE250590T1 (de)	2003-10-15
DE60005560D1 (de)	2003-10-30
AU2244301A (en)	2001-06-25
EP1242396B1 (en)	2003-09-24
WO2001044213A1 (en)	2001-06-21
ZA200204429B (en)	2003-09-03
NO20022857D0 (no)	2002-06-14
IL150085A0 (en)	2002-12-01
JP2003516978A (ja)	2003-05-20
MXPA02005788A (es)	2002-09-18

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