ZA200501332B - Vanilloid receptor ligands and their use in treatments - Google Patents
Vanilloid receptor ligands and their use in treatments Download PDFInfo
- Publication number
- ZA200501332B ZA200501332B ZA200501332A ZA200501332A ZA200501332B ZA 200501332 B ZA200501332 B ZA 200501332B ZA 200501332 A ZA200501332 A ZA 200501332A ZA 200501332 A ZA200501332 A ZA 200501332A ZA 200501332 B ZA200501332 B ZA 200501332B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrimidin
- phenyl
- trifluoromethyl
- oxy
- dihydro
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims description 6
- 108010062740 TRPV Cation Channels Proteins 0.000 title description 12
- 102000011040 TRPV Cation Channels Human genes 0.000 title description 9
- 239000003446 ligand Substances 0.000 title description 2
- 125000005843 halogen group Chemical group 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000004429 atom Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- -1 cyano, oxo, thioxo Chemical group 0.000 claims description 18
- 238000004859 neutralization-reionization mass spectrometry Methods 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 59
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 17
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 14
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims 10
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 claims 9
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims 8
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 2
- GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 claims 2
- USSYLANTAAUELR-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazine Chemical compound N1NC=NC=C1 USSYLANTAAUELR-UHFFFAOYSA-N 0.000 claims 2
- QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical compound C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 claims 2
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 claims 2
- RMQOXNXLVICLNK-UHFFFAOYSA-N 1,4-dihydro-1,3,5-triazine Chemical compound C1NC=NC=N1 RMQOXNXLVICLNK-UHFFFAOYSA-N 0.000 claims 2
- PNJBXRVMRQIFKK-UHFFFAOYSA-N 1,4-dihydrotriazine Chemical compound C1C=CNN=N1 PNJBXRVMRQIFKK-UHFFFAOYSA-N 0.000 claims 2
- LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical compound C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims 2
- IIATVLXXAYLQIZ-UHFFFAOYSA-N 2,5-dihydro-1,2,4-triazine Chemical compound C1C=NNC=N1 IIATVLXXAYLQIZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- WSXNRJXPTNQJBH-UHFFFAOYSA-N 5,6-dihydro-4h-thiazine Chemical compound C1CSN=CC1 WSXNRJXPTNQJBH-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
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- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
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- WOEGBOLRSDFMRG-NSHDSACASA-N (2s)-2-hydroxy-n-[4-[6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl]oxy-1,3-benzothiazol-2-yl]propanamide Chemical compound C1=CC=C2SC(NC(=O)[C@@H](O)C)=NC2=C1OC(N=CN=1)=CC=1C1=CC=C(C(F)(F)F)C=C1 WOEGBOLRSDFMRG-NSHDSACASA-N 0.000 claims 1
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JP (1) | JP4555082B2 (fr) |
KR (1) | KR20050055694A (fr) |
CN (1) | CN1694873A (fr) |
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2003
- 2003-08-08 MX MXPA05001456A patent/MXPA05001456A/es active IP Right Grant
- 2003-08-08 EP EP03785220A patent/EP1546116A1/fr not_active Withdrawn
- 2003-08-08 AR ARP030102863A patent/AR041191A1/es unknown
- 2003-08-08 BR BR0313255-2A patent/BR0313255A/pt not_active IP Right Cessation
- 2003-08-08 CA CA2493667A patent/CA2493667C/fr not_active Expired - Fee Related
- 2003-08-08 CN CNA038238462A patent/CN1694873A/zh active Pending
- 2003-08-08 KR KR1020057001929A patent/KR20050055694A/ko not_active Application Discontinuation
- 2003-08-08 EA EA200500168A patent/EA010380B1/ru not_active IP Right Cessation
- 2003-08-08 AU AU2003264047A patent/AU2003264047B2/en not_active Ceased
- 2003-08-08 NZ NZ537952A patent/NZ537952A/en unknown
- 2003-08-08 JP JP2004528067A patent/JP4555082B2/ja not_active Expired - Fee Related
- 2003-08-08 RS YUP-2005/0161A patent/RS20050161A/sr unknown
- 2003-08-08 EP EP06008555A patent/EP1717220A3/fr not_active Withdrawn
- 2003-08-08 US US10/638,009 patent/US7144888B2/en not_active Expired - Fee Related
- 2003-08-08 WO PCT/US2003/025191 patent/WO2004014871A1/fr active Application Filing
- 2003-08-08 EP EP10008426A patent/EP2270006A1/fr not_active Withdrawn
- 2003-08-08 TW TW092121826A patent/TW200410945A/zh unknown
- 2003-08-08 PL PL03376372A patent/PL376372A1/xx unknown
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2005
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- 2005-08-01 US US11/195,134 patent/US7148221B2/en not_active Expired - Fee Related
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2008
- 2008-06-05 AU AU2008202517A patent/AU2008202517A1/en not_active Abandoned
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PL376372A1 (en) | 2005-12-27 |
US7332511B2 (en) | 2008-02-19 |
EP1546116A1 (fr) | 2005-06-29 |
RS20050161A (en) | 2007-09-21 |
JP4555082B2 (ja) | 2010-09-29 |
KR20050055694A (ko) | 2005-06-13 |
US7144888B2 (en) | 2006-12-05 |
EA010380B1 (ru) | 2008-08-29 |
US20050272777A1 (en) | 2005-12-08 |
MXPA05001456A (es) | 2005-06-06 |
WO2004014871A8 (fr) | 2005-04-07 |
TW200410945A (en) | 2004-07-01 |
AR041191A1 (es) | 2005-05-04 |
CA2493667A1 (fr) | 2004-02-19 |
NZ537952A (en) | 2008-04-30 |
CN1694873A (zh) | 2005-11-09 |
EP2270006A1 (fr) | 2011-01-05 |
US7148221B2 (en) | 2006-12-12 |
EP1717220A2 (fr) | 2006-11-02 |
AU2003264047B2 (en) | 2008-06-26 |
EA200500168A1 (ru) | 2005-08-25 |
US20040082780A1 (en) | 2004-04-29 |
IL166396A0 (en) | 2006-01-15 |
AU2003264047A1 (en) | 2004-02-25 |
JP2006504670A (ja) | 2006-02-09 |
US20050277631A1 (en) | 2005-12-15 |
NO20051193L (no) | 2005-05-04 |
BR0313255A (pt) | 2005-07-12 |
EP1717220A3 (fr) | 2007-08-22 |
AU2008202517A1 (en) | 2008-06-26 |
WO2004014871A1 (fr) | 2004-02-19 |
CA2493667C (fr) | 2010-04-27 |
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