AU1791599A - Novel compounds - Google Patents

Novel compounds Download PDF

Info

Publication number: AU1791599A
Authority: AU; Australia
Prior art keywords: pyridyl; yloxy; butyl; dione; group
Prior art date: 1997-12-05
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.): Abandoned

Application number

AU17915/99A

Other languages

English (en)

Inventor

David Cheshire

David Cladingboel

Thomas Mcinally

Michael Mortimore

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

AstraZeneca UK Ltd

Original Assignee

AstraZeneca UK Ltd

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.)

1997-12-05

Filing date

1998-12-01

Publication date

1999-06-28

1998-12-01 Application filed by AstraZeneca UK Ltd filed Critical AstraZeneca UK Ltd

1999-06-28 Publication of AU1791599A publication Critical patent/AU1791599A/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 143
238000000034 method Methods 0.000 claims description 66
-1 cyano, hydroxyl Chemical group 0.000 claims description 36
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 18
239000012453 solvate Substances 0.000 claims description 17
125000004430 oxygen atom Chemical group O* 0.000 claims description 15
125000004076 pyridyl group Chemical group 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
239000002671 adjuvant Substances 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
238000002560 therapeutic procedure Methods 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
YRKNHZJLTKDOHG-JOCHJYFZSA-N 1-[(2r)-1-[4-(3-nitrophenyl)phenoxy]-4-pyridin-3-ylbutan-2-yl]pyrrolidine-2,5-dione Chemical compound [O-][N+](=O)C1=CC=CC(C=2C=CC(OC[C@@H](CCC=3C=NC=CC=3)N3C(CCC3=O)=O)=CC=2)=C1 YRKNHZJLTKDOHG-JOCHJYFZSA-N 0.000 claims description 3
SOKXBLLWWVPZCM-JOCHJYFZSA-N 3-[4-[(2r)-2-(2,4-dioxo-1,3-thiazolidin-3-yl)-4-pyridin-3-ylbutoxy]phenyl]benzonitrile Chemical compound O=C1CSC(=O)N1[C@@H](COC=1C=CC(=CC=1)C=1C=C(C=CC=1)C#N)CCC1=CC=CN=C1 SOKXBLLWWVPZCM-JOCHJYFZSA-N 0.000 claims description 3
DKVAJDQCPRHXSA-HSZRJFAPSA-N 3-[4-[(2r)-2-(2,5-dioxopyrrolidin-1-yl)-4-pyridin-3-ylbutoxy]phenyl]benzonitrile Chemical compound O=C1CCC(=O)N1[C@@H](COC=1C=CC(=CC=1)C=1C=C(C=CC=1)C#N)CCC1=CC=CN=C1 DKVAJDQCPRHXSA-HSZRJFAPSA-N 0.000 claims description 3
LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 claims description 3
CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 claims description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
UCRZVOUYEJDUJF-HXUWFJFHSA-N 1-[(2r)-1-[4-(3-chloro-4-fluorophenyl)phenoxy]-4-pyridin-3-ylbutan-2-yl]pyrrolidine-2,5-dione Chemical compound C1=C(Cl)C(F)=CC=C1C(C=C1)=CC=C1OC[C@H](N1C(CCC1=O)=O)CCC1=CC=CN=C1 UCRZVOUYEJDUJF-HXUWFJFHSA-N 0.000 claims description 2
FZBQIUHDQLEXGE-UHFFFAOYSA-N 1-[1-[4-(6-methoxypyridin-2-yl)phenoxy]-4-pyridin-4-ylbutan-2-yl]piperidine-2,6-dione Chemical compound COC1=CC=CC(C=2C=CC(OCC(CCC=3C=CN=CC=3)N3C(CCCC3=O)=O)=CC=2)=N1 FZBQIUHDQLEXGE-UHFFFAOYSA-N 0.000 claims description 2
YKMPVOXAMQJSAR-NRFANRHFSA-N 5-[4-[(2s)-2-(2,4-dioxo-1,3-thiazolidin-3-yl)-4-pyridin-3-ylbutoxy]phenyl]-2-fluorobenzonitrile Chemical compound C1=C(C#N)C(F)=CC=C1C(C=C1)=CC=C1OC[C@@H](N1C(SCC1=O)=O)CCC1=CC=CN=C1 YKMPVOXAMQJSAR-NRFANRHFSA-N 0.000 claims description 2
206010062016 Immunosuppression Diseases 0.000 claims description 2
230000001506 immunosuppresive effect Effects 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 1
SLEGIHLFNXPGIL-UHFFFAOYSA-N 3-[1-[4-(4-chlorophenyl)phenoxy]-4-pyridin-4-ylbutan-2-yl]-1,3-oxazolidin-2-one Chemical compound C1=CC(Cl)=CC=C1C(C=C1)=CC=C1OCC(N1C(OCC1)=O)CCC1=CC=NC=C1 SLEGIHLFNXPGIL-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
239000000243 solution Substances 0.000 description 62
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
239000007787 solid Substances 0.000 description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
238000002844 melting Methods 0.000 description 33
230000008018 melting Effects 0.000 description 33
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
239000000203 mixture Substances 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
238000005160 1H NMR spectroscopy Methods 0.000 description 23
238000005481 NMR spectroscopy Methods 0.000 description 23
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 22
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 21
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 18
239000003921 oil Substances 0.000 description 16
235000019198 oils Nutrition 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
102100037602 P2X purinoceptor 7 Human genes 0.000 description 12
101710189965 P2X purinoceptor 7 Proteins 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 12
238000000746 purification Methods 0.000 description 12
229960002317 succinimide Drugs 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
238000010626 work up procedure Methods 0.000 description 12
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
210000004027 cell Anatomy 0.000 description 8
229960004132 diethyl ether Drugs 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
238000010898 silica gel chromatography Methods 0.000 description 7
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 6
239000005695 Ammonium acetate Substances 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
BURJIEWNHIKROD-FWDYTFEUSA-N [[(2r,3r,4r,5s)-5-(6-aminopurin-9-yl)-4,5-dibenzoyl-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O=C([C@@]1(O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@]1(N1C=2N=CN=C(C=2N=C1)N)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 BURJIEWNHIKROD-FWDYTFEUSA-N 0.000 description 6
229940043376 ammonium acetate Drugs 0.000 description 6
235000019257 ammonium acetate Nutrition 0.000 description 6
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
239000006260 foam Substances 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000002245 particle Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000003643 water by type Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
ZMDQVFXSNXQAHC-UHFFFAOYSA-N 1-(4-bromophenoxy)-4-pyridin-4-ylbutan-2-ol Chemical compound C=1C=C(Br)C=CC=1OCC(O)CCC1=CC=NC=C1 ZMDQVFXSNXQAHC-UHFFFAOYSA-N 0.000 description 4
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
239000001273 butane Substances 0.000 description 4
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
230000000694 effects Effects 0.000 description 4
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
RQKAJAWLEOSVNY-LJQANCHMSA-N 3-[(2r)-1-[4-(3-chloro-4-fluorophenyl)phenoxy]-4-pyridin-3-ylbutan-2-yl]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(Cl)C(F)=CC=C1C(C=C1)=CC=C1OC[C@H](N1C(SCC1=O)=O)CCC1=CC=CN=C1 RQKAJAWLEOSVNY-LJQANCHMSA-N 0.000 description 3
MHPBKBRTYLDOKT-HSZRJFAPSA-N 5-[4-[(2r)-2-(2,4-dioxo-1,3-thiazolidin-3-yl)-4-pyridin-3-ylbutoxy]phenyl]benzene-1,3-dicarbonitrile Chemical compound O=C1CSC(=O)N1[C@@H](COC=1C=CC(=CC=1)C=1C=C(C=C(C=1)C#N)C#N)CCC1=CC=CN=C1 MHPBKBRTYLDOKT-HSZRJFAPSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical compound [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 3
229960005542 ethidium bromide Drugs 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
238000004808 supercritical fluid chromatography Methods 0.000 description 3
NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 3
CEKZUJSMKIQUHB-SFHVURJKSA-N (2s)-1-[4-(3-chloro-4-fluorophenyl)phenoxy]-4-pyridin-3-ylbutan-2-ol Chemical compound C([C@H](O)COC=1C=CC(=CC=1)C=1C=C(Cl)C(F)=CC=1)CC1=CC=CN=C1 CEKZUJSMKIQUHB-SFHVURJKSA-N 0.000 description 2
BIYKPXDURAAHNL-FQEVSTJZSA-N (2s)-1-[4-(3-fluorophenyl)phenoxy]-4-pyridin-3-ylbutan-2-ol Chemical compound C([C@H](O)COC=1C=CC(=CC=1)C=1C=C(F)C=CC=1)CC1=CC=CN=C1 BIYKPXDURAAHNL-FQEVSTJZSA-N 0.000 description 2
UWORNNFYITUECW-UHFFFAOYSA-N 1-(4-phenylphenoxy)-4-pyridin-3-ylbutan-2-amine Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1OCC(N)CCC1=CC=CN=C1 UWORNNFYITUECW-UHFFFAOYSA-N 0.000 description 2
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
KMODISUYWZPVGV-UHFFFAOYSA-N 2-bromo-6-methoxypyridine Chemical compound COC1=CC=CC(Br)=N1 KMODISUYWZPVGV-UHFFFAOYSA-N 0.000 description 2
XBAHGVPCQKCVQQ-OAQYLSRUSA-N 3-[(2r)-1-[4-(3-fluorophenyl)phenoxy]-4-pyridin-3-ylbutan-2-yl]-1,3-thiazolidine-2,4-dione Chemical compound FC1=CC=CC(C=2C=CC(OC[C@@H](CCC=3C=NC=CC=3)N3C(SCC3=O)=O)=CC=2)=C1 XBAHGVPCQKCVQQ-OAQYLSRUSA-N 0.000 description 2
SOKXBLLWWVPZCM-QFIPXVFZSA-N 3-[4-[(2s)-2-(2,4-dioxo-1,3-thiazolidin-3-yl)-4-pyridin-3-ylbutoxy]phenyl]benzonitrile Chemical compound O=C1CSC(=O)N1[C@H](COC=1C=CC(=CC=1)C=1C=C(C=CC=1)C#N)CCC1=CC=CN=C1 SOKXBLLWWVPZCM-QFIPXVFZSA-N 0.000 description 2
ZNRGSYUVFVNSAW-UHFFFAOYSA-N 3-nitrophenylboronic acid Chemical compound OB(O)C1=CC=CC([N+]([O-])=O)=C1 ZNRGSYUVFVNSAW-UHFFFAOYSA-N 0.000 description 2
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
HZECSUSPMAVEFQ-UHFFFAOYSA-N 4-pyridin-3-ylbutan-2-ol Chemical compound CC(O)CCC1=CC=CN=C1 HZECSUSPMAVEFQ-UHFFFAOYSA-N 0.000 description 2
DTTZJRAEFQOOBU-QFIPXVFZSA-N 5-[4-[(2s)-2-hydroxy-4-pyridin-3-ylbutoxy]phenyl]benzene-1,3-dicarbonitrile Chemical compound C([C@H](O)COC=1C=CC(=CC=1)C=1C=C(C=C(C=1)C#N)C#N)CC1=CC=CN=C1 DTTZJRAEFQOOBU-QFIPXVFZSA-N 0.000 description 2
KEODZYDOBHDZOT-UHFFFAOYSA-N 5-bromobenzene-1,3-dicarbonitrile Chemical compound BrC1=CC(C#N)=CC(C#N)=C1 KEODZYDOBHDZOT-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
102000000589 Interleukin-1 Human genes 0.000 description 2
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229940044601 receptor agonist Drugs 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
238000011160 research Methods 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229910021653 sulphate ion Inorganic materials 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
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
239000012085 test solution Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
208000027185 varicose disease Diseases 0.000 description 1

Classifications

- 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
- C07D401/02—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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms
- 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
- C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

AU17915/99A 1997-12-05 1998-12-01 Novel compounds Abandoned AU1791599A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
SE9704546		1997-12-05
SE9704546A SE9704546D0 (sv)	1997-12-05	1997-12-05	Novel compounds
PCT/SE1998/002190 WO1999029686A1 (en)	1997-12-05	1998-12-01	Novel compounds

Publications (1)

Publication Number	Publication Date
AU1791599A true AU1791599A (en)	1999-06-28

Family

ID=20409283

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU17915/99A Abandoned AU1791599A (en)	1997-12-05	1998-12-01	Novel compounds

Country Status (16)

Country	Link
EP (1)	EP1037889A1 (xx)
JP (1)	JP2001525406A (xx)
KR (1)	KR20010032800A (xx)
CN (1)	CN1284074A (xx)
AU (1)	AU1791599A (xx)
BR (1)	BR9813378A (xx)
CA (1)	CA2312357A1 (xx)
EE (1)	EE200000321A (xx)
HU (1)	HUP0100731A3 (xx)
IL (1)	IL136368A0 (xx)
NO (1)	NO20002787L (xx)
PL (1)	PL340837A1 (xx)
SE (1)	SE9704546D0 (xx)
SK (1)	SK8442000A3 (xx)
TR (1)	TR200001544T2 (xx)
WO (1)	WO1999029686A1 (xx)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
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SE9901875D0 (sv) *	1999-05-25	1999-05-25	Astra Pharma Prod	Novel compounds
SE9904505D0 (sv)	1999-12-09	1999-12-09	Astra Pharma Prod	Novel compounds
SE9904652D0 (sv)	1999-12-17	1999-12-17	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
JP2002330787A (ja) *	2000-10-21	2002-11-19	Astrazeneca Ab	化学物質
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
US7071223B1 (en)	2002-12-31	2006-07-04	Pfizer, Inc.	Benzamide inhibitors of the P2X7 receptor
PA8591801A1 (es)	2002-12-31	2004-07-26	Pfizer Prod Inc	Inhibidores benzamidicos del receptor p2x7.
ATE355273T1 (de)	2003-05-12	2006-03-15	Pfizer Prod Inc	Benzamidinhibitoren des p2x7-rezeptors
GB0324498D0 (en)	2003-07-21	2003-11-26	Aventis Pharma Inc	Heterocyclic compounds as P2X7 ion channel blockers
MXPA06014022A (es)	2004-06-29	2007-02-08	Pfizer Prod Inc	Prcedimientos para preparar inhibidores de p2x7.
BRPI0709596A2 (pt)	2006-03-16	2011-07-19	Renovis Inc	compostos bicicloeteroarila como moduladores de p2x7 e seus usos
CA2645556C (en)	2006-03-16	2016-05-24	Renovis, Inc.	Bicycloheteroaryl compounds as p2x7 modulators and uses thereof
TWI464148B (zh)	2006-03-16	2014-12-11	Evotec Us Inc	作為ｐ２ｘ7調節劑之雙環雜芳基化合物與其用途
TW200813018A (en)	2006-06-09	2008-03-16	Astrazeneca Ab	Novel compounds
GB0613473D0 (en) *	2006-07-06	2006-08-16	Glaxo Group Ltd	Novel compounds
BRPI0714062A2 (pt)	2006-07-06	2012-12-18	Glaxo Group Ltd	n-fenil-metil-5-oxo-prolina-2-amidas substituìdas como antagonistas do receptor da p2x, e os seus métodos de uso
ES2576643T3 (es)	2007-03-09	2016-07-08	Second Genome, Inc.	Compuestos de bicicloheteroarilo como moduladores de P2X7 y usos de los mismos
US20100168171A1 (en) *	2007-03-28	2010-07-01	Paul John Beswick	Piperidinone Carboxamide Derivatives as P2X7 Modulators
WO2008119685A2 (en) *	2007-03-29	2008-10-09	Glaxo Group Limited	Oxazolidine and morpholine carboxamide derivatives as p2x7 modulators
JP2010523524A (ja) *	2007-04-03	2010-07-15	グラクソグループリミテッド	Ｐ２ｘ７調節因子としてのイミダゾリジンカルボキサミド誘導体
US8119661B2 (en)	2007-09-11	2012-02-21	Astrazeneca Ab	Piperidine derivatives and their use as muscarinic receptor modulators
GB0803729D0 (en) *	2008-02-29	2008-04-09	Ge Healthcare Ltd	Imaging the central nervous system
ATE494926T1 (de)	2008-03-25	2011-01-15	Affectis Pharmaceuticals Ag	Neuartige p2x7r-antagonisten und ihre verwendung
WO2010118921A1 (en)	2009-04-14	2010-10-21	Affectis Pharmaceuticals Ag	Novel p2x7r antagonists and their use
EP2322149A1 (en)	2009-11-03	2011-05-18	Universidad del Pais Vasco	Methods and compositions for the treatment of ischemia
BR112012028850A2 (pt)	2010-05-14	2015-09-15	Affectis Pharmaceuticals Ag	métodos para a preparação de antagonistas de p2x7r
WO2012110190A1 (en)	2011-02-17	2012-08-23	Affectis Pharmaceuticals Ag	Novel p2x7r antagonists and their use
WO2012163456A1 (en)	2011-05-27	2012-12-06	Affectis Pharmaceuticals Ag	Novel p2x7r antagonists and their use
WO2012163792A1 (en)	2011-05-27	2012-12-06	Affectis Pharmaceuticals Ag	Novel p2x7r antagonists and their use
JP7337083B2 (ja)	2017-11-21	2023-09-01	スリーエムイノベイティブプロパティズカンパニー	口腔用植物系水中油型エマルジョン及び使用方法
CN111511348A (zh)	2017-12-20	2020-08-07	3M创新有限公司	口腔组合物及使用方法
EP3727336A1 (en)	2017-12-20	2020-10-28	3M Innovative Properties Company	Oral compositions and methods of use
CN113226287B (zh)	2018-12-29	2025-10-17	舒万诺知识产权公司	口腔制品及使用方法

1997
- 1997-12-05 SE SE9704546A patent/SE9704546D0/xx unknown
1998
- 1998-12-01 IL IL13636898A patent/IL136368A0/xx unknown
- 1998-12-01 CN CN98813490A patent/CN1284074A/zh active Pending
- 1998-12-01 PL PL98340837A patent/PL340837A1/xx unknown
- 1998-12-01 AU AU17915/99A patent/AU1791599A/en not_active Abandoned
- 1998-12-01 TR TR2000/01544T patent/TR200001544T2/xx unknown
- 1998-12-01 HU HU0100731A patent/HUP0100731A3/hu unknown
- 1998-12-01 EP EP98962753A patent/EP1037889A1/en not_active Withdrawn
- 1998-12-01 KR KR1020007006117A patent/KR20010032800A/ko not_active Withdrawn
- 1998-12-01 CA CA002312357A patent/CA2312357A1/en not_active Abandoned
- 1998-12-01 EE EEP200000321A patent/EE200000321A/xx unknown
- 1998-12-01 JP JP2000524280A patent/JP2001525406A/ja not_active Withdrawn
- 1998-12-01 SK SK844-2000A patent/SK8442000A3/sk unknown
- 1998-12-01 BR BR9813378-0A patent/BR9813378A/pt not_active Application Discontinuation
- 1998-12-01 WO PCT/SE1998/002190 patent/WO1999029686A1/en not_active Ceased
2000
- 2000-05-31 NO NO20002787A patent/NO20002787L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CA2312357A1 (en)	1999-06-17
SE9704546D0 (sv)	1997-12-05
SK8442000A3 (en)	2001-01-18
HUP0100731A2 (hu)	2002-05-29
TR200001544T2 (tr)	2000-11-21
BR9813378A (pt)	2000-10-10
PL340837A1 (en)	2001-02-26
NO20002787L (no)	2000-08-01
EP1037889A1 (en)	2000-09-27
JP2001525406A (ja)	2001-12-11
HUP0100731A3 (en)	2002-08-28
NO20002787D0 (no)	2000-05-31
CN1284074A (zh)	2001-02-14
IL136368A0 (en)	2001-06-14
WO1999029686A1 (en)	1999-06-17
KR20010032800A (ko)	2001-04-25
EE200000321A (et)	2001-08-15

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AU1791599A (en)	1999-06-28	Novel compounds
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AU2020286381C1 (en)	2025-07-10	Imidazolo derivatives, compositions and methods as orexin antagonists
JP2020530446A (ja)	2020-10-22	化合物、組成物、及び、方法
AU2006207300B2 (en)	2011-03-03	Substituted triazole derivatives as oxytocin antagonists
KR20160090304A (ko)	2016-07-29	우레아 유도체 또는 그의 약리학적으로 허용되는 염
US9718812B2 (en)	2017-08-01	Substituted thiazole or oxazole P2X7 receptor antagonists
DE69222280T2 (de)	1998-03-05	Kondensierte Benzeoxyessigsäurederivate
EP2974730B1 (en)	2018-01-31	Drug for respiratory diseases
JP2016523851A (ja)	2016-08-12	新規ｃｙｐ１７阻害剤／抗アンドロゲン
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Legal Events

Date	Code	Title	Description
2001-02-22	MK1	Application lapsed section 142(2)(a) - no request for examination in relevant period