JP2008535829A5 - - Google Patents
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- Publication number
- JP2008535829A5 JP2008535829A5 JP2008504108A JP2008504108A JP2008535829A5 JP 2008535829 A5 JP2008535829 A5 JP 2008535829A5 JP 2008504108 A JP2008504108 A JP 2008504108A JP 2008504108 A JP2008504108 A JP 2008504108A JP 2008535829 A5 JP2008535829 A5 JP 2008535829A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- thiopyrano
- tetrahydro
- pyrazole
- carboxylic acid
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 46
- 125000003118 aryl group Chemical group 0.000 claims 38
- 229910052736 halogen Inorganic materials 0.000 claims 37
- 150000002367 halogens Chemical class 0.000 claims 37
- 125000003545 alkoxy group Chemical group 0.000 claims 35
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 28
- 125000000623 heterocyclic group Chemical group 0.000 claims 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims 26
- 125000002947 alkylene group Chemical group 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 150000002431 hydrogen Chemical class 0.000 claims 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- -1 —NR 8 R 9 Chemical group 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- 239000004480 active ingredient Substances 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 7
- 125000004104 aryloxy group Chemical group 0.000 claims 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 6
- 125000001118 alkylidene group Chemical group 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 5
- 208000011580 syndromic disease Diseases 0.000 claims 5
- 239000003433 contraceptive agent Substances 0.000 claims 4
- 230000002254 contraceptive effect Effects 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 239000000556 agonist Substances 0.000 claims 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- 102100031151 C-C chemokine receptor type 2 Human genes 0.000 claims 2
- 101710149815 C-C chemokine receptor type 2 Proteins 0.000 claims 2
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 claims 2
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 claims 2
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical group C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 claims 2
- 230000036528 appetite Effects 0.000 claims 2
- 235000019789 appetite Nutrition 0.000 claims 2
- 239000000812 cholinergic antagonist Substances 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000004060 metabolic process Effects 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000000583 progesterone congener Substances 0.000 claims 2
- 239000002469 receptor inverse agonist Substances 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 229960004394 topiramate Drugs 0.000 claims 2
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 claims 1
- OVIPZSJCTHRMHU-GZTJUZNOSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-n-(pyridin-2-ylmethyl)-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NCC=3N=CC=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=C2CS(=O)(=O)C\1 OVIPZSJCTHRMHU-GZTJUZNOSA-N 0.000 claims 1
- WKLHMNPOUZGDHB-UOBPLZBXSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-n-[(1r)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 WKLHMNPOUZGDHB-UOBPLZBXSA-N 0.000 claims 1
- HRECVQBCZODJIK-YAJBTMAUSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-n-[(1r)-1-pyridin-2-ylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1N=CC=CC=1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 HRECVQBCZODJIK-YAJBTMAUSA-N 0.000 claims 1
- WKLHMNPOUZGDHB-NNIWKIFQSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-n-[(1s)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 WKLHMNPOUZGDHB-NNIWKIFQSA-N 0.000 claims 1
- OFCMZYZMEAKBTI-SFQUDFHCSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-n-piperidin-1-yl-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCCCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CS(=O)(=O)C\1 OFCMZYZMEAKBTI-SFQUDFHCSA-N 0.000 claims 1
- AXMPUIGLHSHCLA-AVOCASMFSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-5-oxo-n-[(1r)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CS(=O)C\C2=C/C1=CC=C(F)C=C1 AXMPUIGLHSHCLA-AVOCASMFSA-N 0.000 claims 1
- YEPPHSKZRQDPFU-SFQUDFHCSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-5-oxo-n-piperidin-1-yl-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCCCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CS(=O)C\1 YEPPHSKZRQDPFU-SFQUDFHCSA-N 0.000 claims 1
- PELZRCABPQTZBQ-UOBPLZBXSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1r)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 PELZRCABPQTZBQ-UOBPLZBXSA-N 0.000 claims 1
- MKTSQSZQVWOLGK-YAJBTMAUSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1r)-1-pyridin-2-ylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1N=CC=CC=1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 MKTSQSZQVWOLGK-YAJBTMAUSA-N 0.000 claims 1
- YOVWYQHRLSQCEY-ZQATUQSNSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1r,2r)-2-hydroxycyclohexyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound O[C@@H]1CCCC[C@H]1NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 YOVWYQHRLSQCEY-ZQATUQSNSA-N 0.000 claims 1
- NLRZHTGURNWLIU-SYKJDFLGSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1r,2r)-2-hydroxycyclopentyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound O[C@@H]1CCC[C@H]1NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 NLRZHTGURNWLIU-SYKJDFLGSA-N 0.000 claims 1
- PBQPQDQJQSMOMU-UNQBSXFESA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1r,2s)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@@H]1C2=CC=CC=C2C[C@@H]1O)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 PBQPQDQJQSMOMU-UNQBSXFESA-N 0.000 claims 1
- UWQXBQBQXNSQEK-UNQBSXFESA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1r,2s)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-5,5-dioxo-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@@H]1C2=CC=CC=C2C[C@@H]1O)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 UWQXBQBQXNSQEK-UNQBSXFESA-N 0.000 claims 1
- PELZRCABPQTZBQ-NNIWKIFQSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1s)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 PELZRCABPQTZBQ-NNIWKIFQSA-N 0.000 claims 1
- UWQXBQBQXNSQEK-BFJWEILNSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-5,5-dioxo-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H]1C2=CC=CC=C2C[C@H]1O)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 UWQXBQBQXNSQEK-BFJWEILNSA-N 0.000 claims 1
- AYFLQMYEGOTWSE-JFDTWPCUSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1s,2s)-2-hydroxycyclohexyl]-5,5-dioxo-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound O[C@H]1CCCC[C@@H]1NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 AYFLQMYEGOTWSE-JFDTWPCUSA-N 0.000 claims 1
- XVWXKJOJCDHHHA-FVECTHPASA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound COC[C@H]1CCCN1NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 XVWXKJOJCDHHHA-FVECTHPASA-N 0.000 claims 1
- URESYLXNEURLES-FVECTHPASA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]-5,5-dioxo-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound COC[C@H]1CCCN1NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 URESYLXNEURLES-FVECTHPASA-N 0.000 claims 1
- XVWXKJOJCDHHHA-KDMTZKAISA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound COC[C@@H]1CCCN1NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 XVWXKJOJCDHHHA-KDMTZKAISA-N 0.000 claims 1
- URESYLXNEURLES-KDMTZKAISA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]-5,5-dioxo-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound COC[C@@H]1CCCN1NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 URESYLXNEURLES-KDMTZKAISA-N 0.000 claims 1
- IPXVSLUMYPDGFQ-SFQUDFHCSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-piperidin-1-yl-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCCCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CSC\1 IPXVSLUMYPDGFQ-SFQUDFHCSA-N 0.000 claims 1
- JENYBNXKZRCRSJ-LFIBNONCSA-N (7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-pyrrolidin-1-yl-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CSC\1 JENYBNXKZRCRSJ-LFIBNONCSA-N 0.000 claims 1
- POOVBRNGDMMGJG-XDHOZWIPSA-N (7z)-1-(2,4-dichlorophenyl)-n-(2,6-dimethylpiperidin-1-yl)-7-[(4-fluorophenyl)methylidene]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound CC1CCCC(C)N1NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 POOVBRNGDMMGJG-XDHOZWIPSA-N 0.000 claims 1
- UYUGOIUWPKBVLM-XDHOZWIPSA-N (7z)-1-(2,4-dichlorophenyl)-n-(2,6-dimethylpiperidin-1-yl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound CC1CCCC(C)N1NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 UYUGOIUWPKBVLM-XDHOZWIPSA-N 0.000 claims 1
- UDMHCKQOVWJRFY-ISPGYRLHSA-N (7z)-1-(4-chlorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-n-[(1r)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C=CC(Cl)=CC=2)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 UDMHCKQOVWJRFY-ISPGYRLHSA-N 0.000 claims 1
- DCQJSZCZXLMJLB-NBVRZTHBSA-N (7z)-1-(4-chlorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-n-piperidin-1-yl-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCCCC3)C=3C=CC(Cl)=CC=3)=C2CS(=O)(=O)C\1 DCQJSZCZXLMJLB-NBVRZTHBSA-N 0.000 claims 1
- AJNIPYNNFIAMRO-XDJHFCHBSA-N (7z)-1-(4-chlorophenyl)-7-[(4-fluorophenyl)methylidene]-n'-methyl-5,5-dioxo-n'-phenyl-4h-thiopyrano[4,3-c]pyrazole-3-carbohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)C1=NN(C=2C=CC(Cl)=CC=2)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 AJNIPYNNFIAMRO-XDJHFCHBSA-N 0.000 claims 1
- FEANEXDEJVFZTJ-ISPGYRLHSA-N (7z)-1-(4-chlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1r)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C=CC(Cl)=CC=2)C2=C1CSC\C2=C/C1=CC=C(F)C=C1 FEANEXDEJVFZTJ-ISPGYRLHSA-N 0.000 claims 1
- BLZRKIRWCUFBAH-NBVRZTHBSA-N (7z)-1-(4-chlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-piperidin-1-yl-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCCCC3)C=3C=CC(Cl)=CC=3)=C2CSC\1 BLZRKIRWCUFBAH-NBVRZTHBSA-N 0.000 claims 1
- ARTBSHLCWHOIHI-GHRIWEEISA-N (7z)-1-(4-chlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-pyrrolidin-1-yl-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCCC3)C=3C=CC(Cl)=CC=3)=C2CSC\1 ARTBSHLCWHOIHI-GHRIWEEISA-N 0.000 claims 1
- NETMBGXSKGTJMB-UOBPLZBXSA-N (7z)-2-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-n-[(1r)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C(N(N=C12)C=3C(=CC(Cl)=CC=3)Cl)=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 NETMBGXSKGTJMB-UOBPLZBXSA-N 0.000 claims 1
- NETMBGXSKGTJMB-NNIWKIFQSA-N (7z)-2-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-n-[(1s)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)C(N(N=C12)C=3C(=CC(Cl)=CC=3)Cl)=C1CS(=O)(=O)C\C2=C/C1=CC=C(F)C=C1 NETMBGXSKGTJMB-NNIWKIFQSA-N 0.000 claims 1
- ZHBIAACONKEDTJ-SFQUDFHCSA-N (7z)-2-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-n-piperidin-1-yl-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C2=NN(C=3C(=CC(Cl)=CC=3)Cl)C(C(=O)NN3CCCCC3)=C2CS(=O)(=O)C\1 ZHBIAACONKEDTJ-SFQUDFHCSA-N 0.000 claims 1
- PJYLIEXJKCUSPD-UOBPLZBXSA-N (7z)-2-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-n-[(1r)-1-phenylethyl]-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C(N(N=C12)C=3C(=CC(Cl)=CC=3)Cl)=C1CSC\C2=C/C1=CC=C(F)C=C1 PJYLIEXJKCUSPD-UOBPLZBXSA-N 0.000 claims 1
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- 2006-03-16 WO PCT/US2006/009424 patent/WO2006107561A1/en not_active Ceased
- 2006-03-16 JP JP2008504108A patent/JP5127697B2/ja not_active Expired - Fee Related
- 2006-03-16 MX MX2007012233A patent/MX2007012233A/es active IP Right Grant
- 2006-03-16 EA EA200702130A patent/EA200702130A1/ru unknown
- 2006-03-16 AU AU2006232945A patent/AU2006232945B2/en not_active Ceased
- 2006-03-16 DE DE602006004197T patent/DE602006004197D1/de active Active
- 2006-03-16 EP EP06738484A patent/EP1863479B1/en active Active
- 2006-03-16 KR KR1020077025259A patent/KR20080004559A/ko not_active Withdrawn
- 2006-03-16 BR BRPI0609790-1A patent/BRPI0609790A2/pt not_active IP Right Cessation
- 2006-03-16 US US11/376,844 patent/US20060223798A1/en not_active Abandoned
-
2007
- 2007-10-07 IL IL186430A patent/IL186430A0/en unknown
- 2007-10-17 CO CO07109275A patent/CO6321135A2/es not_active Application Discontinuation
- 2007-10-29 CR CR9479A patent/CR9479A/es not_active Application Discontinuation
- 2007-10-29 NO NO20075463A patent/NO20075463L/no not_active Application Discontinuation
- 2007-10-30 ZA ZA200709342A patent/ZA200709342B/xx unknown
- 2007-12-07 US US11/952,375 patent/US7524964B2/en not_active Expired - Fee Related
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