JP5127697B2 - テトラヒドロチオピラノピラゾールカンナビノイドモジュレーター - Google Patents
テトラヒドロチオピラノピラゾールカンナビノイドモジュレーター Download PDFInfo
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- JP5127697B2 JP5127697B2 JP2008504108A JP2008504108A JP5127697B2 JP 5127697 B2 JP5127697 B2 JP 5127697B2 JP 2008504108 A JP2008504108 A JP 2008504108A JP 2008504108 A JP2008504108 A JP 2008504108A JP 5127697 B2 JP5127697 B2 JP 5127697B2
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- JP
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- Prior art keywords
- phenyl
- tetrahydro
- thiopyrano
- 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.)
- Expired - Fee Related
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- 229930003827 cannabinoid Natural products 0.000 title description 74
- 239000003557 cannabinoid Substances 0.000 title description 74
- UBEXPFAJZMPWAL-UHFFFAOYSA-N 1,2,3,3a-tetrahydrothiopyrano[3,2-c]pyrazole Chemical compound C1=CSC2CNNC2=C1 UBEXPFAJZMPWAL-UHFFFAOYSA-N 0.000 title description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 235
- 150000001875 compounds Chemical class 0.000 claims abstract description 228
- 208000035475 disorder Diseases 0.000 claims abstract description 126
- 201000010099 disease Diseases 0.000 claims abstract description 109
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 108
- 230000001404 mediated effect Effects 0.000 claims abstract description 70
- 239000000203 mixture Substances 0.000 claims description 115
- 125000000217 alkyl group Chemical group 0.000 claims description 104
- 125000003118 aryl group Chemical group 0.000 claims description 80
- 125000003545 alkoxy group Chemical group 0.000 claims description 77
- 229910052736 halogen Inorganic materials 0.000 claims description 75
- 150000002367 halogens Chemical class 0.000 claims description 74
- -1 —NR 8 R 9 Chemical group 0.000 claims description 74
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 57
- 125000000623 heterocyclic group Chemical group 0.000 claims description 57
- 125000002947 alkylene group Chemical group 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 239000003433 contraceptive agent Substances 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 29
- 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 28
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
- 239000000812 cholinergic antagonist Substances 0.000 claims description 27
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 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
- 230000036528 appetite Effects 0.000 claims description 21
- 235000019789 appetite Nutrition 0.000 claims description 21
- 229940124575 antispasmodic agent Drugs 0.000 claims description 20
- 229940124558 contraceptive agent Drugs 0.000 claims description 20
- KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound 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 17
- 239000002469 receptor inverse agonist Substances 0.000 claims description 17
- 206010012601 diabetes mellitus Diseases 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 229960004394 topiramate Drugs 0.000 claims description 16
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 14
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
- 208000002193 Pain Diseases 0.000 claims description 13
- 230000002254 contraceptive effect Effects 0.000 claims description 13
- 230000015654 memory Effects 0.000 claims description 13
- 230000036407 pain Effects 0.000 claims description 13
- 206010010904 Convulsion Diseases 0.000 claims description 12
- 230000013016 learning Effects 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 229960002870 gabapentin Drugs 0.000 claims description 11
- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 claims description 11
- 208000011117 substance-related disease Diseases 0.000 claims description 11
- 229960000604 valproic acid Drugs 0.000 claims description 11
- 125000001118 alkylidene group Chemical group 0.000 claims description 10
- 230000004663 cell proliferation Effects 0.000 claims description 10
- 230000019771 cognition Effects 0.000 claims description 10
- 230000004410 intraocular pressure Effects 0.000 claims description 10
- 229960001848 lamotrigine Drugs 0.000 claims description 10
- 230000004060 metabolic process Effects 0.000 claims description 10
- 210000000056 organ Anatomy 0.000 claims description 10
- 201000009032 substance abuse Diseases 0.000 claims description 10
- 231100000736 substance abuse Toxicity 0.000 claims description 10
- 229940124597 therapeutic agent Drugs 0.000 claims description 10
- 208000010412 Glaucoma Diseases 0.000 claims description 9
- 230000002921 anti-spasmodic effect Effects 0.000 claims description 9
- 230000008602 contraction Effects 0.000 claims description 9
- 230000037023 motor activity Effects 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 208000019022 Mood disease Diseases 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
- 230000004112 neuroprotection Effects 0.000 claims description 6
- 208000023504 respiratory system disease Diseases 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 208000007101 Muscle Cramp Diseases 0.000 claims description 5
- 208000008238 Muscle Spasticity Diseases 0.000 claims description 5
- 208000005392 Spasm Diseases 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 208000026278 immune system disease Diseases 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 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
- 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
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000000391 smoking effect Effects 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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
- HIASVPASZVPMBK-UDWIEESQSA-N (7z)-n-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-1-(4-chlorophenyl)-7-[(4-fluorophenyl)methylidene]-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)=C2CSC\1 HIASVPASZVPMBK-UDWIEESQSA-N 0.000 claims description 3
- NDPCFSUMKGYWHF-UDWIEESQSA-N (7z)-n-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-1-(4-chlorophenyl)-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)=C2CS(=O)(=O)C\1 NDPCFSUMKGYWHF-UDWIEESQSA-N 0.000 claims description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
- 208000016285 Movement disease Diseases 0.000 claims description 3
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims description 3
- ZXINDFJFLUVDAF-SFQUDFHCSA-N [(7z)-1-(2,4-dichlorophenyl)-7-[(4-fluorophenyl)methylidene]-4h-thiopyrano[4,3-c]pyrazol-3-yl]-piperidin-1-ylmethanone Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)N3CCCCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CSC\1 ZXINDFJFLUVDAF-SFQUDFHCSA-N 0.000 claims description 3
- 229960000304 folic acid Drugs 0.000 claims description 3
- 235000019152 folic acid Nutrition 0.000 claims description 3
- 239000011724 folic acid Substances 0.000 claims description 3
- 230000004580 weight loss Effects 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 2
- 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 2
- 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 2
- 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 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 2
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- 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 2
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- BLBTUPYWSFPVEU-UHFFFAOYSA-N potassium;2-methylpropan-2-olate;hydrate Chemical compound O.[K+].CC(C)(C)[O-] BLBTUPYWSFPVEU-UHFFFAOYSA-N 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
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- HHDQUKNFPJLUKD-NSHDSACASA-N tert-butyl n-methylsulfonyl-n-[(1s)-1-phenylethyl]carbamate Chemical compound CC(C)(C)OC(=O)N(S(C)(=O)=O)[C@@H](C)C1=CC=CC=C1 HHDQUKNFPJLUKD-NSHDSACASA-N 0.000 description 1
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- PHCBRBWANGJMHS-UHFFFAOYSA-J tetrasodium;disulfate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O PHCBRBWANGJMHS-UHFFFAOYSA-J 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4162—1,2-Diazoles condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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- A—HUMAN NECESSITIES
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- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
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- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Addiction (AREA)
- Pulmonology (AREA)
- Child & Adolescent Psychology (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66689805P | 2005-03-31 | 2005-03-31 | |
| US60/666.898 | 2005-03-31 | ||
| PCT/US2006/009424 WO2006107561A1 (en) | 2005-03-31 | 2006-03-16 | Tetrahydrothiopyrano pyrazole cannabinoid modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008535829A JP2008535829A (ja) | 2008-09-04 |
| JP2008535829A5 JP2008535829A5 (enExample) | 2009-05-07 |
| JP5127697B2 true JP5127697B2 (ja) | 2013-01-23 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2008504108A Expired - Fee Related JP5127697B2 (ja) | 2005-03-31 | 2006-03-16 | テトラヒドロチオピラノピラゾールカンナビノイドモジュレーター |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US20060223798A1 (enExample) |
| EP (1) | EP1863479B1 (enExample) |
| JP (1) | JP5127697B2 (enExample) |
| KR (1) | KR20080004559A (enExample) |
| CN (1) | CN101189007A (enExample) |
| AT (1) | ATE416768T1 (enExample) |
| AU (1) | AU2006232945B2 (enExample) |
| BR (1) | BRPI0609790A2 (enExample) |
| CA (1) | CA2603104A1 (enExample) |
| CO (1) | CO6321135A2 (enExample) |
| CR (1) | CR9479A (enExample) |
| DE (1) | DE602006004197D1 (enExample) |
| EA (1) | EA200702130A1 (enExample) |
| IL (1) | IL186430A0 (enExample) |
| MX (1) | MX2007012233A (enExample) |
| NO (1) | NO20075463L (enExample) |
| WO (1) | WO2006107561A1 (enExample) |
| ZA (1) | ZA200709342B (enExample) |
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| CN101863903B (zh) * | 2010-06-08 | 2014-03-12 | 沈阳药科大学 | 1,4-二氢噻吩并[3’,2’:5,6]噻喃并[4,3-c]吡唑-3-羧酸衍生物及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| FR2800375B1 (fr) * | 1999-11-03 | 2004-07-23 | Sanofi Synthelabo | Derives tricycliques d'acide pyrazolecarboxylique, leur preparation, les compositions pharmaceutiques en contenant |
| JP2004502642A (ja) * | 2000-02-11 | 2004-01-29 | ブリストル−マイヤーズ スクイブ カンパニー | カンナビノイドレセプターモジュレーター、それらの製造方法、および呼吸系および非呼吸系疾患の処置のためのカンナビノイドレセプターモジュレーターの使用 |
| WO2003035005A2 (en) * | 2001-10-26 | 2003-05-01 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
| US20040214856A1 (en) * | 2003-04-23 | 2004-10-28 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| US7145012B2 (en) * | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
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2006
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- 2006-03-16 WO PCT/US2006/009424 patent/WO2006107561A1/en not_active Ceased
- 2006-03-16 CA CA002603104A patent/CA2603104A1/en not_active Abandoned
- 2006-03-16 KR KR1020077025259A patent/KR20080004559A/ko not_active Withdrawn
- 2006-03-16 EP EP06738484A patent/EP1863479B1/en not_active Expired - Lifetime
- 2006-03-16 US US11/376,844 patent/US20060223798A1/en not_active Abandoned
- 2006-03-16 MX MX2007012233A patent/MX2007012233A/es active IP Right Grant
- 2006-03-16 JP JP2008504108A patent/JP5127697B2/ja not_active Expired - Fee Related
- 2006-03-16 EA EA200702130A patent/EA200702130A1/ru unknown
- 2006-03-16 AT AT06738484T patent/ATE416768T1/de not_active IP Right Cessation
- 2006-03-16 DE DE602006004197T patent/DE602006004197D1/de not_active Expired - Lifetime
- 2006-03-16 CN CNA2006800192594A patent/CN101189007A/zh active Pending
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2007
- 2007-10-07 IL IL186430A patent/IL186430A0/en unknown
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- 2007-10-30 ZA ZA200709342A patent/ZA200709342B/xx unknown
- 2007-12-07 US US11/952,375 patent/US7524964B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7524964B2 (en) | 2009-04-28 |
| BRPI0609790A2 (pt) | 2010-04-27 |
| WO2006107561A1 (en) | 2006-10-12 |
| KR20080004559A (ko) | 2008-01-09 |
| AU2006232945A1 (en) | 2006-10-12 |
| AU2006232945B2 (en) | 2012-02-23 |
| JP2008535829A (ja) | 2008-09-04 |
| MX2007012233A (es) | 2008-03-18 |
| EP1863479B1 (en) | 2008-12-10 |
| CA2603104A1 (en) | 2006-10-12 |
| US20060223798A1 (en) | 2006-10-05 |
| CO6321135A2 (es) | 2011-09-20 |
| DE602006004197D1 (de) | 2009-01-22 |
| EA200702130A1 (ru) | 2008-04-28 |
| EP1863479A1 (en) | 2007-12-12 |
| CR9479A (es) | 2008-09-09 |
| US20080085899A1 (en) | 2008-04-10 |
| IL186430A0 (en) | 2008-01-20 |
| ATE416768T1 (de) | 2008-12-15 |
| ZA200709342B (en) | 2009-09-30 |
| NO20075463L (no) | 2007-12-21 |
| CN101189007A (zh) | 2008-05-28 |
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