JP2008515897A - フェニル誘導体及びそれを使用する方法 - Google Patents
フェニル誘導体及びそれを使用する方法 Download PDFInfo
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- JP2008515897A JP2008515897A JP2007535753A JP2007535753A JP2008515897A JP 2008515897 A JP2008515897 A JP 2008515897A JP 2007535753 A JP2007535753 A JP 2007535753A JP 2007535753 A JP2007535753 A JP 2007535753A JP 2008515897 A JP2008515897 A JP 2008515897A
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- JP
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- Prior art keywords
- dimethyl
- methyl
- oxo
- morpholin
- hexyl
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 118
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 284
- 230000000694 effects Effects 0.000 claims abstract description 55
- 102000018208 Cannabinoid Receptor Human genes 0.000 claims abstract description 38
- 108050007331 Cannabinoid receptor Proteins 0.000 claims abstract description 38
- 208000002193 Pain Diseases 0.000 claims abstract description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 230000036407 pain Effects 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 15
- 230000000302 ischemic effect Effects 0.000 claims abstract description 11
- 230000006907 apoptotic process Effects 0.000 claims abstract description 8
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 6
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 6
- 208000025609 Urogenital disease Diseases 0.000 claims abstract description 6
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 6
- 230000010410 reperfusion Effects 0.000 claims abstract description 5
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 4
- 230000005961 cardioprotection Effects 0.000 claims abstract description 4
- 230000003211 malignant effect Effects 0.000 claims abstract description 4
- 208000010643 digestive system disease Diseases 0.000 claims abstract 3
- 208000018685 gastrointestinal system disease Diseases 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- -1 4- {3 ′-[(3-ethylureido) -methyl] -2-hydroxybiphenyl-4-yl} -4-methylpentyl Chemical group 0.000 claims description 76
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 61
- 229930003827 cannabinoid Natural products 0.000 claims description 49
- 239000003557 cannabinoid Substances 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 230000027455 binding Effects 0.000 claims description 24
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 claims description 22
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 claims description 22
- 229940065144 cannabinoids Drugs 0.000 claims description 22
- 239000004202 carbamide Substances 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 22
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 claims description 21
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 claims description 21
- 210000003169 central nervous system Anatomy 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 150000001408 amides Chemical class 0.000 claims description 15
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- XKJYDRZUEZPHQR-UHFFFAOYSA-N 1-[[2-[4-(1-butoxy-2-methylpropan-2-yl)-2-hydroxyphenyl]phenyl]methyl]-3-ethylurea Chemical compound OC1=CC(C(C)(C)COCCCC)=CC=C1C1=CC=CC=C1CNC(=O)NCC XKJYDRZUEZPHQR-UHFFFAOYSA-N 0.000 claims description 14
- NTXDMOLVKRLXFU-UHFFFAOYSA-N 1-ethyl-3-[[3-[2-hydroxy-4-[1-(2-methoxyethoxy)-2-methylpropan-2-yl]phenyl]phenyl]methyl]urea Chemical compound CCNC(=O)NCC1=CC=CC(C=2C(=CC(=CC=2)C(C)(C)COCCOC)O)=C1 NTXDMOLVKRLXFU-UHFFFAOYSA-N 0.000 claims description 14
- VVRAVZFJSDFNCN-UHFFFAOYSA-N 1-ethyl-3-[[3-[2-hydroxy-4-[2-methyl-1-(3-morpholin-4-yl-3-oxopropoxy)propan-2-yl]phenyl]phenyl]methyl]urea Chemical compound CCNC(=O)NCC1=CC=CC(C=2C(=CC(=CC=2)C(C)(C)COCCC(=O)N2CCOCC2)O)=C1 VVRAVZFJSDFNCN-UHFFFAOYSA-N 0.000 claims description 14
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- DYLZPYREUKSMPN-UHFFFAOYSA-N 1-ethyl-3-[[3-[2-hydroxy-4-(2-methyl-7-morpholin-4-yl-7-oxoheptan-2-yl)phenyl]phenyl]methyl]urea Chemical compound CCNC(=O)NCC1=CC=CC(C=2C(=CC(=CC=2)C(C)(C)CCCCC(=O)N2CCOCC2)O)=C1 DYLZPYREUKSMPN-UHFFFAOYSA-N 0.000 claims description 13
- VRPMOAWLXIIINE-UHFFFAOYSA-N n-[4-[4-[3-[(ethylcarbamoylamino)methyl]phenyl]-3-hydroxyphenyl]-4-methylpentyl]morpholine-4-carboxamide Chemical compound CCNC(=O)NCC1=CC=CC(C=2C(=CC(=CC=2)C(C)(C)CCCNC(=O)N2CCOCC2)O)=C1 VRPMOAWLXIIINE-UHFFFAOYSA-N 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- ODIGHDFCSCTGRP-UHFFFAOYSA-N 1-ethyl-3-[[2-[2-hydroxy-4-(2-methyl-7-morpholin-4-yl-7-oxoheptan-2-yl)phenyl]phenyl]methyl]urea Chemical compound CCNC(=O)NCC1=CC=CC=C1C1=CC=C(C(C)(C)CCCCC(=O)N2CCOCC2)C=C1O ODIGHDFCSCTGRP-UHFFFAOYSA-N 0.000 claims description 11
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 11
- ZYYRQKGUGFTVFS-UHFFFAOYSA-N n-[4-[4-[3-[(ethylcarbamoylamino)methyl]phenyl]-3-hydroxyphenyl]-4-methylpentyl]-2,2-dimethylpropanamide Chemical compound CCNC(=O)NCC1=CC=CC(C=2C(=CC(=CC=2)C(C)(C)CCCNC(=O)C(C)(C)C)O)=C1 ZYYRQKGUGFTVFS-UHFFFAOYSA-N 0.000 claims description 11
- CXDDFBIGVYQIDP-UHFFFAOYSA-N 1-[[3-[2-hydroxy-4-(2-methyl-7-morpholin-4-yl-7-oxoheptan-2-yl)phenyl]phenyl]methyl]-3-methylurea Chemical compound CNC(=O)NCC1=CC=CC(C=2C(=CC(=CC=2)C(C)(C)CCCCC(=O)N2CCOCC2)O)=C1 CXDDFBIGVYQIDP-UHFFFAOYSA-N 0.000 claims description 10
- YQLGBZUAMXVUEI-UHFFFAOYSA-N 1-ethyl-3-[[3-[2-hydroxy-4-[2-methyl-5-(propan-2-ylcarbamoylamino)pentan-2-yl]phenyl]phenyl]methyl]urea Chemical compound CCNC(=O)NCC1=CC=CC(C=2C(=CC(=CC=2)C(C)(C)CCCNC(=O)NC(C)C)O)=C1 YQLGBZUAMXVUEI-UHFFFAOYSA-N 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 10
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- OCDHQJFJELDVRL-UHFFFAOYSA-N n-[[3-[2-hydroxy-4-(2-methyl-7-morpholin-4-yl-7-oxoheptan-2-yl)phenyl]phenyl]methyl]oxolane-2-carboxamide Chemical compound C=1C=C(C=2C=C(CNC(=O)C3OCCC3)C=CC=2)C(O)=CC=1C(C)(C)CCCCC(=O)N1CCOCC1 OCDHQJFJELDVRL-UHFFFAOYSA-N 0.000 claims description 10
- OYKQLEPXISZDLW-UHFFFAOYSA-N 1-[[2-[4-(1-butoxy-2-methylpropan-2-yl)-2-hydroxyphenyl]phenyl]methyl]-3-propylurea Chemical compound OC1=CC(C(C)(C)COCCCC)=CC=C1C1=CC=CC=C1CNC(=O)NCCC OYKQLEPXISZDLW-UHFFFAOYSA-N 0.000 claims description 9
- DAXSMQRQVAKZNG-UHFFFAOYSA-N 1-[[3-[4-(1-butoxy-2-methylpropan-2-yl)-2-hydroxyphenyl]phenyl]methyl]-3-ethylurea Chemical compound OC1=CC(C(C)(C)COCCCC)=CC=C1C1=CC=CC(CNC(=O)NCC)=C1 DAXSMQRQVAKZNG-UHFFFAOYSA-N 0.000 claims description 9
- HTNPSFAZKYMXCR-UHFFFAOYSA-N 1-[[3-[4-(1-butoxy-2-methylpropan-2-yl)-2-hydroxyphenyl]phenyl]methyl]-3-propylurea Chemical compound OC1=CC(C(C)(C)COCCCC)=CC=C1C1=CC=CC(CNC(=O)NCCC)=C1 HTNPSFAZKYMXCR-UHFFFAOYSA-N 0.000 claims description 9
- JHYOROCYFXJGHL-UHFFFAOYSA-N 1-ethyl-3-[[2-[2-hydroxy-4-[1-(2-methoxyethoxy)-2-methylpropan-2-yl]phenyl]phenyl]methyl]urea Chemical compound CCNC(=O)NCC1=CC=CC=C1C1=CC=C(C(C)(C)COCCOC)C=C1O JHYOROCYFXJGHL-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 9
- QBEUIIFDVMSCND-UHFFFAOYSA-N 1-[[2-[2-hydroxy-4-(2-methyl-7-morpholin-4-yl-7-oxoheptan-2-yl)phenyl]phenyl]methyl]-3-methylurea Chemical compound CNC(=O)NCC1=CC=CC=C1C1=CC=C(C(C)(C)CCCCC(=O)N2CCOCC2)C=C1O QBEUIIFDVMSCND-UHFFFAOYSA-N 0.000 claims description 8
- WXBLLNIQMCHXLT-UHFFFAOYSA-N 1-[[2-[2-hydroxy-4-(2-methyl-7-morpholin-4-yl-7-oxoheptan-2-yl)phenyl]phenyl]methyl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NCC1=CC=CC=C1C1=CC=C(C(C)(C)CCCCC(=O)N2CCOCC2)C=C1O WXBLLNIQMCHXLT-UHFFFAOYSA-N 0.000 claims description 8
- LCQYKUDAUNCSSQ-UHFFFAOYSA-N 1-[[3-[2-hydroxy-4-(2-methyl-7-morpholin-4-yl-7-oxoheptan-2-yl)phenyl]phenyl]methyl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NCC1=CC=CC(C=2C(=CC(=CC=2)C(C)(C)CCCCC(=O)N2CCOCC2)O)=C1 LCQYKUDAUNCSSQ-UHFFFAOYSA-N 0.000 claims description 8
- PAYBZLDNIMUAAS-UHFFFAOYSA-N 1-ethyl-3-[[2-[2-hydroxy-4-(2-methyl-7-morpholin-4-yl-7-oxohept-5-en-2-yl)phenyl]phenyl]methyl]urea Chemical compound CCNC(=O)NCC1=CC=CC=C1C1=CC=C(C(C)(C)CCC=CC(=O)N2CCOCC2)C=C1O PAYBZLDNIMUAAS-UHFFFAOYSA-N 0.000 claims description 8
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 8
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 8
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 8
- 238000000338 in vitro Methods 0.000 claims description 8
- CDWBYLUTXBVEIB-UHFFFAOYSA-N 1-ethyl-3-[[3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]phenyl]methyl]urea Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1C1=CC=CC(CNC(=O)NCC)=C1 CDWBYLUTXBVEIB-UHFFFAOYSA-N 0.000 claims description 7
- 229960004126 codeine Drugs 0.000 claims description 7
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- 229960005181 morphine Drugs 0.000 claims description 7
- ZQFKEUYMYUOXKJ-UHFFFAOYSA-N 1-ethyl-3-[[2-[2-hydroxy-4-[2-methyl-5-(propan-2-ylcarbamoylamino)pentan-2-yl]phenyl]phenyl]methyl]urea Chemical compound CCNC(=O)NCC1=CC=CC=C1C1=CC=C(C(C)(C)CCCNC(=O)NC(C)C)C=C1O ZQFKEUYMYUOXKJ-UHFFFAOYSA-N 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- RBOXVHNMENFORY-DNJOTXNNSA-N dihydrocodeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC RBOXVHNMENFORY-DNJOTXNNSA-N 0.000 claims description 6
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- JPQXFNMNYZDVSD-UHFFFAOYSA-N n-[[2-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]phenyl]methyl]methanesulfonamide Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1C1=CC=CC=C1CNS(C)(=O)=O JPQXFNMNYZDVSD-UHFFFAOYSA-N 0.000 claims description 6
- REWRCWAGFNKEQL-UHFFFAOYSA-N n-[[3-[2-hydroxy-4-(2-methyl-7-morpholin-4-yl-7-oxoheptan-2-yl)phenyl]phenyl]methyl]methanesulfonamide Chemical compound C=1C=C(C=2C=C(CNS(C)(=O)=O)C=CC=2)C(O)=CC=1C(C)(C)CCCCC(=O)N1CCOCC1 REWRCWAGFNKEQL-UHFFFAOYSA-N 0.000 claims description 6
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- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims description 5
- XXRUTSUNCKOHFC-UHFFFAOYSA-N 1-ethyl-3-[2-[2-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]phenyl]ethyl]urea Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1C1=CC=CC=C1CCNC(=O)NCC XXRUTSUNCKOHFC-UHFFFAOYSA-N 0.000 claims description 5
- OPDCCVBZYUHIMX-UHFFFAOYSA-N 1-ethyl-3-[2-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]phenyl]urea Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1C1=CC=CC=C1NC(=O)NCC OPDCCVBZYUHIMX-UHFFFAOYSA-N 0.000 claims description 5
- IITIBFWSYVGQBN-UHFFFAOYSA-N 1-ethyl-3-[[2-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]phenyl]methyl]urea Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1C1=CC=CC=C1CNC(=O)NCC IITIBFWSYVGQBN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000036528 appetite Effects 0.000 claims description 5
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- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 claims description 5
- 229960004193 dextropropoxyphene Drugs 0.000 claims description 5
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- UHJYXYOGTXKELL-UHFFFAOYSA-N methyl 6-[3-hydroxy-4-[3-(methanesulfonamido)phenyl]phenyl]-6-methylheptanoate Chemical compound OC1=CC(C(C)(C)CCCCC(=O)OC)=CC=C1C1=CC=CC(NS(C)(=O)=O)=C1 UHJYXYOGTXKELL-UHFFFAOYSA-N 0.000 claims description 5
- CAQBYPHVAJVIHK-UHFFFAOYSA-N n-[2-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]phenyl]methanesulfonamide Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1C1=CC=CC=C1NS(C)(=O)=O CAQBYPHVAJVIHK-UHFFFAOYSA-N 0.000 claims description 5
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- KYNXYODUHRYEFA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-3-[[2-[2-hydroxy-4-(2-methyl-7-morpholin-4-yl-7-oxoheptan-2-yl)phenyl]phenyl]methyl]urea Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)NCC1=CC=CC=C1C1=CC=C(C(C)(C)CCCCC(=O)N2CCOCC2)C=C1O KYNXYODUHRYEFA-UHFFFAOYSA-N 0.000 claims description 4
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- OYPVCNMUTABJQP-UHFFFAOYSA-N 1-ethyl-3-[[3-[2-hydroxy-4-(2-methyl-7-morpholin-4-ylheptan-2-yl)phenyl]phenyl]methyl]urea Chemical compound CCNC(=O)NCC1=CC=CC(C=2C(=CC(=CC=2)C(C)(C)CCCCCN2CCOCC2)O)=C1 OYPVCNMUTABJQP-UHFFFAOYSA-N 0.000 claims description 4
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
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- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/04—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
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- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
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- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
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- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
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- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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| PCT/US2005/035677 WO2006041841A1 (en) | 2004-10-05 | 2005-10-04 | Phenyl derivatives and methods of use |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008524196A (ja) * | 2004-12-21 | 2008-07-10 | ユーシーエル ビジネス ピーエルシー | モジュレーター |
| JP2023505898A (ja) * | 2019-12-16 | 2023-02-13 | スパゴ ナノメディカル アクチエボラグ | フェノール系化合物の固定化 |
| JP2023100613A (ja) * | 2021-01-06 | 2023-07-19 | 中外製薬株式会社 | 化合物ライブラリ |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2654026A1 (en) * | 2006-06-08 | 2007-12-13 | Neurokey A/S | Use of cannabinoid receptor agonists as hypothermia inducing drugs for the treatment of ischemia |
| WO2008109027A2 (en) * | 2007-03-02 | 2008-09-12 | University Of Tennessee Research Foundation, The | Tri-aryl/heteroaroaromatic cannabinoids and use thereof |
| CN101815513B (zh) * | 2007-08-07 | 2012-11-14 | 斯泰伦博斯大学 | 含有对乙酰氨基苯酚的眼用制剂 |
| EP2211619A1 (en) * | 2007-10-18 | 2010-08-04 | Merck Sharp & Dohme Corp. | Substituted 1,2,4-oxadiazoles and analogs thereof as cb2 receptor modulators, useful in the treatment of pain, respiratory and non-respiratory diseases |
| WO2009140078A1 (en) * | 2008-05-16 | 2009-11-19 | The Procter & Gamble Company | Treatment of lower urinary tract dysfunction with cb2-receptor-selective agonists |
| KR20110130489A (ko) * | 2009-03-23 | 2011-12-05 | 스미또모 가가꾸 가부시끼가이샤 | 시클로프로판카르복실산에스테르의 제조 방법 |
| US9855225B2 (en) * | 2011-08-18 | 2018-01-02 | Temple University Office Of Technology Transfer | Cannabinoid receptor treatments |
| CN103288684B (zh) * | 2013-05-03 | 2014-12-10 | 西安交通大学 | 一种具有抗肿瘤活性的联苯脲化合物及其制备方法 |
| US9585867B2 (en) | 2015-08-06 | 2017-03-07 | Charles Everett Ankner | Cannabinod formulation for the sedation of a human or animal |
| US12364668B2 (en) | 2017-11-15 | 2025-07-22 | The Regents Of The University Of California | Treatment of opioid use disorder, opioid withdrawal symptoms, and chronic pain |
| US12409131B2 (en) | 2019-10-03 | 2025-09-09 | Pike Therapeutics Usa, Inc. | Transdermal delivery of dronabinol |
| CN114650809A (zh) | 2019-10-03 | 2022-06-21 | 斯塔顿治疗公司 | 屈大麻酚的透皮递送 |
| CA3155176A1 (en) | 2019-10-11 | 2021-04-15 | Pike Therapeutics, Inc., 1219014 B.C. Ltd. | Transdermal compositions comprising cannabidiol (cbd) for use in the treatment of seizure disorders |
| US12016829B2 (en) | 2019-10-11 | 2024-06-25 | Pike Therapeutics Inc. | Pharmaceutical composition and method for treating seizure disorders |
| CA3155181A1 (en) | 2019-10-14 | 2021-04-22 | Pike Therapeutics, Inc., 1219014 B.C. Ltd. | Transdermal delivery of cannabidiol |
| US12268699B2 (en) | 2019-10-14 | 2025-04-08 | Pike Therapeutics Inc. | Transdermal delivery of tetrahydrocannabinol |
| US12121617B2 (en) | 2019-10-14 | 2024-10-22 | Pike Therapeutics Inc. | Transdermal delivery of cannabidiol |
| JP7687721B2 (ja) * | 2020-12-25 | 2025-06-03 | エムティックスバイオ カンパニ- リミテッド | 新規なアミノアルカン酸にビフェニル基を導入した誘導体化合物およびそれを含む抗炎症用組成物 |
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| JP2002363164A (ja) * | 2001-04-06 | 2002-12-18 | Mitsubishi Chemicals Corp | ピラゾールカルボキサミド類、その中間体およびこれを有効成分とする有害生物防除剤 |
| WO2003091189A1 (en) * | 2002-04-25 | 2003-11-06 | Virginia Commonwealth University | Cannabinoids |
| WO2004017920A2 (en) * | 2002-08-23 | 2004-03-04 | University Of Connecticut | Novel biphenyl and biphenyl-like cannabinoids |
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| US3663608A (en) * | 1969-12-10 | 1972-05-16 | Bristol Myers Co | 1-phenyl-3-aminoalkyl-1,2,3,4-tetrahydronaphthalenes and the salts thereof |
| US4055664A (en) * | 1975-02-10 | 1977-10-25 | Armour Pharmaceutical Company | Pharmaceutical preparations containing 4-(4-biphenylyl) butylamines and treatment of the animal organism therewith |
| DE3063585D1 (en) | 1979-05-19 | 1983-07-07 | Beecham Group Plc | Chroman derivatives, processes for their preparation and pharmaceutical compositions containing them |
| SE0300010D0 (sv) | 2003-01-07 | 2003-01-07 | Astrazeneca Ab | Novel Compounds |
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2005
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- 2005-10-04 WO PCT/US2005/035677 patent/WO2006041841A1/en not_active Ceased
- 2005-10-04 JP JP2007535753A patent/JP2008515897A/ja active Pending
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- 2005-10-04 BR BRPI0516544-0A patent/BRPI0516544A/pt not_active IP Right Cessation
- 2005-10-04 CA CA002583297A patent/CA2583297A1/en not_active Abandoned
- 2005-10-04 AU AU2005294459A patent/AU2005294459A1/en not_active Abandoned
- 2005-10-04 CN CN2005800340695A patent/CN101035758B/zh not_active Expired - Fee Related
- 2005-10-04 EP EP05810259A patent/EP1817277A4/en not_active Withdrawn
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2010
- 2010-01-18 US US12/689,078 patent/US20100168108A1/en not_active Abandoned
Patent Citations (6)
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| JP2002363164A (ja) * | 2001-04-06 | 2002-12-18 | Mitsubishi Chemicals Corp | ピラゾールカルボキサミド類、その中間体およびこれを有効成分とする有害生物防除剤 |
| WO2003091189A1 (en) * | 2002-04-25 | 2003-11-06 | Virginia Commonwealth University | Cannabinoids |
| WO2004017920A2 (en) * | 2002-08-23 | 2004-03-04 | University Of Connecticut | Novel biphenyl and biphenyl-like cannabinoids |
| JP2005536554A (ja) * | 2002-08-23 | 2005-12-02 | ユニバーシティ オブ コネチカット | 新規なビフェニル及びビフェニル様カンナビノイド |
| WO2004046091A2 (en) * | 2002-11-19 | 2004-06-03 | Galderma Research & Development, S.N.C. | Biaromatic compounds which activate ppar-gama type receptors, and use thereof in cosmetic or pharmaceutical compositions |
| WO2004052846A1 (en) * | 2002-12-06 | 2004-06-24 | Bayer Healthcare Ag | Tetrahydro-naphthalene derivatives |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008524196A (ja) * | 2004-12-21 | 2008-07-10 | ユーシーエル ビジネス ピーエルシー | モジュレーター |
| JP2023505898A (ja) * | 2019-12-16 | 2023-02-13 | スパゴ ナノメディカル アクチエボラグ | フェノール系化合物の固定化 |
| JP7675445B2 (ja) | 2019-12-16 | 2025-05-13 | スパゴ ナノメディカル アクチエボラグ | フェノール系化合物の固定化 |
| US12441837B2 (en) | 2019-12-16 | 2025-10-14 | Spago Nanomedical Ab | Immobilization of phenolic compounds |
| JP2023100613A (ja) * | 2021-01-06 | 2023-07-19 | 中外製薬株式会社 | 化合物ライブラリ |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2005294459A1 (en) | 2006-04-20 |
| US7671052B2 (en) | 2010-03-02 |
| WO2006041841A1 (en) | 2006-04-20 |
| US20100168108A1 (en) | 2010-07-01 |
| CA2583297A1 (en) | 2006-04-20 |
| MX2007003826A (es) | 2007-04-23 |
| EP1817277A1 (en) | 2007-08-15 |
| CN101035758A (zh) | 2007-09-12 |
| CN101035758B (zh) | 2010-12-01 |
| US20060074086A1 (en) | 2006-04-06 |
| BRPI0516544A (pt) | 2008-09-09 |
| EP1817277A4 (en) | 2010-03-10 |
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