KR20080004559A - 테트라하이드로티오피라노 피라졸 카나비노이드 모듈레이터 - Google Patents

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Publication number

KR20080004559A

KR20080004559A KR1020077025259A KR20077025259A KR20080004559A KR 20080004559 A KR20080004559 A KR 20080004559A KR 1020077025259 A KR1020077025259 A KR 1020077025259A KR 20077025259 A KR20077025259 A KR 20077025259A KR 20080004559 A KR20080004559 A KR 20080004559A

Authority

KR

South Korea

Prior art keywords

phenyl

tetrahydro

thiopyrano

carboxylic acid

fluoro

Prior art date

2005-03-31

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.)

Withdrawn

Links

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• 239000003557 cannabinoid Substances 0.000 title description 81
• 229930003827 cannabinoid Natural products 0.000 title description 81
• UBEXPFAJZMPWAL-UHFFFAOYSA-N 1,2,3,3a-tetrahydrothiopyrano[3,2-c]pyrazole Chemical compound C1=CSC2CNNC2=C1 UBEXPFAJZMPWAL-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 282
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 230
• 201000010099 disease Diseases 0.000 claims abstract description 115
• 208000035475 disorder Diseases 0.000 claims abstract description 115
• 238000000034 method Methods 0.000 claims abstract description 115
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 108
• 230000001404 mediated effect Effects 0.000 claims abstract description 66
• 102000005962 receptors Human genes 0.000 claims abstract description 63
• 108020003175 receptors Proteins 0.000 claims abstract description 63
• -1 —NR 8 N 9 Chemical group 0.000 claims description 125
• 239000000203 mixture Substances 0.000 claims description 120
• 125000000217 alkyl group Chemical group 0.000 claims description 102
• 125000003118 aryl group Chemical group 0.000 claims description 78
• 229910052736 halogen Inorganic materials 0.000 claims description 76
• 150000002367 halogens Chemical class 0.000 claims description 76
• 125000003545 alkoxy group Chemical group 0.000 claims description 72
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 60
• 239000003814 drug Substances 0.000 claims description 59
• 125000000623 heterocyclic group Chemical group 0.000 claims description 59
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 57
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 46
• 125000002947 alkylene group Chemical group 0.000 claims description 40
• 229940124597 therapeutic agent Drugs 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 36
• 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 description 34
• 239000003433 contraceptive agent Substances 0.000 claims description 33
• 239000001961 anticonvulsive agent Substances 0.000 claims description 32
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 30
• 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 claims description 26
• 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 26
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 24
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
• NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 22
• 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 description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 16
• 125000004104 aryloxy group Chemical group 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 claims description 15
• 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 claims description 15
• 230000036528 appetite Effects 0.000 claims description 14
• 235000019789 appetite Nutrition 0.000 claims description 14
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
• 206010012601 diabetes mellitus Diseases 0.000 claims description 13
• 229960004394 topiramate Drugs 0.000 claims description 13
• 239000000556 agonist Substances 0.000 claims description 12
• 230000001773 anti-convulsant effect Effects 0.000 claims description 12
• 229960003965 antiepileptics Drugs 0.000 claims description 12
• 239000000651 prodrug Substances 0.000 claims description 12
• 229940002612 prodrug Drugs 0.000 claims description 12
• 230000001225 therapeutic effect Effects 0.000 claims description 12
• 101710187010 Cannabinoid receptor 1 Proteins 0.000 claims description 11
• 102100033868 Cannabinoid receptor 1 Human genes 0.000 claims description 11
• 208000002193 Pain Diseases 0.000 claims description 11
• 229960002870 gabapentin Drugs 0.000 claims description 11
• 230000036407 pain Effects 0.000 claims description 11
• 229960000604 valproic acid Drugs 0.000 claims description 11
• 125000001118 alkylidene group Chemical group 0.000 claims description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• 230000002254 contraceptive effect Effects 0.000 claims description 10
• PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 claims description 10
• 206010010904 Convulsion Diseases 0.000 claims description 9
• FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 claims description 9
• 230000004663 cell proliferation Effects 0.000 claims description 9
• 229940125425 inverse agonist Drugs 0.000 claims description 9
• 229960001848 lamotrigine Drugs 0.000 claims description 9
• 230000013016 learning Effects 0.000 claims description 9
• 230000015654 memory Effects 0.000 claims description 9
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
• 239000003554 cannabinoid 1 receptor agonist Substances 0.000 claims description 8
• 229960000623 carbamazepine Drugs 0.000 claims description 8
• 239000002207 metabolite Substances 0.000 claims description 8
• 208000011117 substance-related disease Diseases 0.000 claims description 8
• 208000007101 Muscle Cramp Diseases 0.000 claims description 7
• 208000005392 Spasm Diseases 0.000 claims description 7
• 239000003555 cannabinoid 1 receptor antagonist Substances 0.000 claims description 7
• 230000019771 cognition Effects 0.000 claims description 7
• 230000004410 intraocular pressure Effects 0.000 claims description 7
• 210000000056 organ Anatomy 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 208000010412 Glaucoma Diseases 0.000 claims description 6
• 230000008602 contraction Effects 0.000 claims description 6
• OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 230000004060 metabolic process Effects 0.000 claims description 6
• 230000000391 smoking effect Effects 0.000 claims description 6
• 230000002269 spontaneous effect Effects 0.000 claims description 6
• 201000009032 substance abuse Diseases 0.000 claims description 6
• 231100000736 substance abuse Toxicity 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 claims description 5
• 208000019022 Mood disease Diseases 0.000 claims description 5
• CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 claims description 5
• 239000005557 antagonist Substances 0.000 claims description 5
• LRNUFCLZJXZYLW-UHFFFAOYSA-N n-piperidin-1-yl-1h-pyrazole-5-carboxamide Chemical compound C1=CNN=C1C(=O)NN1CCCCC1 LRNUFCLZJXZYLW-UHFFFAOYSA-N 0.000 claims description 5
• 229960002036 phenytoin Drugs 0.000 claims description 5
• LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims description 5
• 102000018208 Cannabinoid Receptor Human genes 0.000 claims description 4
• 108050007331 Cannabinoid receptor Proteins 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 208000026278 immune system disease Diseases 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• UOCYIXGKOTWCPB-SECBINFHSA-N n-[(1r)-1-phenylethyl]-1h-pyrazole-5-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C=1C=CNN=1 UOCYIXGKOTWCPB-SECBINFHSA-N 0.000 claims description 4
• 229940127234 oral contraceptive Drugs 0.000 claims description 4
• 239000003539 oral contraceptive agent Substances 0.000 claims description 4
• 239000000583 progesterone congener Substances 0.000 claims description 4
• 208000023504 respiratory system disease Diseases 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 claims description 3
• PDNHLCRMUIGNBV-ZCFIWIBFSA-N (1r)-1-pyridin-2-ylethanamine Chemical compound C[C@@H](N)C1=CC=CC=N1 PDNHLCRMUIGNBV-ZCFIWIBFSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• YSOMEAULYFGOAC-QAEAHILHSA-N (7z)-7-[(5-chlorofuran-2-yl)methylidene]-1-(2,4-dichlorophenyl)-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(Cl)O1 YSOMEAULYFGOAC-QAEAHILHSA-N 0.000 claims description 3
• WVFLFBFAYPGCLV-GXDHUFHOSA-N (7z)-7-[(5-chlorofuran-2-yl)methylidene]-1-(2,4-dichlorophenyl)-5,5-dioxo-n-piperidin-1-yl-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound O1C(Cl)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCCCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CS(=O)(=O)C\1 WVFLFBFAYPGCLV-GXDHUFHOSA-N 0.000 claims description 3
• RIMIUJHVIORMRH-QAEAHILHSA-N (7z)-7-[(5-chlorofuran-2-yl)methylidene]-n-[(1r)-1-cyclohexylethyl]-1-(2,4-dichlorophenyl)-5,5-dioxo-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C1CCCCC1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CS(=O)(=O)C\C2=C/C1=CC=C(Cl)O1 RIMIUJHVIORMRH-QAEAHILHSA-N 0.000 claims description 3
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• YUERNKIYCWEGTA-VXLYETTFSA-N (7z)-n-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CC4CCCC4C3)C=3C(=CC(Cl)=CC=3)Cl)=C2CS(=O)(=O)C\1 YUERNKIYCWEGTA-VXLYETTFSA-N 0.000 claims description 3
• PIBPXNWSOZZNLU-VXLYETTFSA-N (7z)-n-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-1-(2,4-difluorophenyl)-7-[(4-fluorophenyl)methylidene]-5,5-dioxo-4h-thiopyrano[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CC4CCCC4C3)C=3C(=CC(F)=CC=3)F)=C2CS(=O)(=O)C\1 PIBPXNWSOZZNLU-VXLYETTFSA-N 0.000 claims description 3
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