JP4159363B2 - α２Ｂアドレナリン受容体の調節剤として有用な（２−ヒドロキシ）エチル−チオウレア - Google Patents
α２Ｂアドレナリン受容体の調節剤として有用な（２−ヒドロキシ）エチル−チオウレア Download PDFInfo
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- JP4159363B2 JP4159363B2 JP2002567898A JP2002567898A JP4159363B2 JP 4159363 B2 JP4159363 B2 JP 4159363B2 JP 2002567898 A JP2002567898 A JP 2002567898A JP 2002567898 A JP2002567898 A JP 2002567898A JP 4159363 B2 JP4159363 B2 JP 4159363B2
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- IPSVDERFJPMANL-UHFFFAOYSA-N 2-hydroxyethylthiourea Chemical compound NC(=S)NCCO IPSVDERFJPMANL-UHFFFAOYSA-N 0.000 title description 3
- 102000030484 alpha-2 Adrenergic Receptor Human genes 0.000 title 1
- 108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 218
- 208000002193 Pain Diseases 0.000 claims description 46
- 230000000694 effects Effects 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 230000036407 pain Effects 0.000 claims description 21
- 108060003345 Adrenergic Receptor Proteins 0.000 claims description 19
- 102000017910 Adrenergic receptor Human genes 0.000 claims description 19
- 208000000094 Chronic Pain Diseases 0.000 claims description 17
- -1 n- butyl Chemical group 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 208000004454 Hyperalgesia Diseases 0.000 claims description 10
- 239000000556 agonist Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 206010053552 allodynia Diseases 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000000048 adrenergic agonist Substances 0.000 claims description 5
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 18
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 98
- 238000004611 spectroscopical analysis Methods 0.000 description 89
- 238000000034 method Methods 0.000 description 80
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 53
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 239000000203 mixture Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
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- 235000019439 ethyl acetate Nutrition 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 18
- 239000012267 brine Substances 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 15
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 14
- 230000004044 response Effects 0.000 description 14
- 241000700159 Rattus Species 0.000 description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 239000003480 eluent Substances 0.000 description 11
- 150000002540 isothiocyanates Chemical class 0.000 description 11
- CIRVCLYLBPPWHB-UHFFFAOYSA-N tert-butyl-(2-isothiocyanatoethoxy)-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCN=C=S CIRVCLYLBPPWHB-UHFFFAOYSA-N 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 150000001540 azides Chemical class 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 206010039897 Sedation Diseases 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 208000005298 acute pain Diseases 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 210000003141 lower extremity Anatomy 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 7
- 230000036280 sedation Effects 0.000 description 7
- 230000000638 stimulation Effects 0.000 description 7
- IITQJMYAYSNIMI-UHFFFAOYSA-N 3-Methyl-2-cyclohexen-1-one Chemical compound CC1=CC(=O)CCC1 IITQJMYAYSNIMI-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 230000001404 mediated effect Effects 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000001356 surgical procedure Methods 0.000 description 6
- LKTNAAYQZJAXCJ-UHFFFAOYSA-N 2-methylcyclohex-2-en-1-one Chemical compound CC1=CCCCC1=O LKTNAAYQZJAXCJ-UHFFFAOYSA-N 0.000 description 5
- 0 CCN(C)C(C)[*+] Chemical compound CCN(C)C(C)[*+] 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 5
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000001647 drug administration Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- MGQAYMJJBRADGQ-UHFFFAOYSA-N methyl 3-methylcyclopentene-1-carboxylate Chemical compound COC(=O)C1=CC(C)CC1 MGQAYMJJBRADGQ-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 230000035807 sensation Effects 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 4
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 4
- 229930182837 (R)-adrenaline Natural products 0.000 description 4
- GUQXGIGHAPLAER-UHFFFAOYSA-N 1-(azidomethyl)-2-methylcyclohexene Chemical compound CC1=C(CN=[N+]=[N-])CCCC1 GUQXGIGHAPLAER-UHFFFAOYSA-N 0.000 description 4
- VOQWNMCMLHXRHX-UHFFFAOYSA-N 1-(cyclohex-2-en-1-ylmethyl)-3-(2-hydroxyethyl)thiourea Chemical compound OCCNC(=S)NCC1CCCC=C1 VOQWNMCMLHXRHX-UHFFFAOYSA-N 0.000 description 4
- AHAATKOSNXIXCX-UHFFFAOYSA-N 2-ethylcyclohex-2-en-1-one Chemical compound CCC1=CCCCC1=O AHAATKOSNXIXCX-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 description 4
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 description 4
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical class O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 4
- 230000002526 effect on cardiovascular system Effects 0.000 description 4
- 229960005139 epinephrine Drugs 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 229960002748 norepinephrine Drugs 0.000 description 4
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
- 210000001032 spinal nerve Anatomy 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- 210000001170 unmyelinated nerve fiber Anatomy 0.000 description 4
- NNPLIBITKZHWBR-UHFFFAOYSA-N (3-ethylcyclohex-2-en-1-yl)methanol Chemical compound CCC1=CC(CO)CCC1 NNPLIBITKZHWBR-UHFFFAOYSA-N 0.000 description 3
- CJCVPKOMPJQGRU-UHFFFAOYSA-N 1-(4-hydroxycyclohexyl)-3-(2-hydroxyethyl)thiourea Chemical compound OCCNC(=S)NC1CCC(O)CC1 CJCVPKOMPJQGRU-UHFFFAOYSA-N 0.000 description 3
- OSSNZOUVMDUFJA-UHFFFAOYSA-N 1-cyclohexyl-3-(2-hydroxyethyl)thiourea Chemical compound OCCNC(=S)NC1CCCCC1 OSSNZOUVMDUFJA-UHFFFAOYSA-N 0.000 description 3
- ALWMJSIQQQUYMJ-UHFFFAOYSA-N 1-ethyl-3-methylidenecyclohexene Chemical compound CCC1=CC(=C)CCC1 ALWMJSIQQQUYMJ-UHFFFAOYSA-N 0.000 description 3
- LJNIRZXCJFJLRC-UHFFFAOYSA-N 1-methyl-3-methylidenecyclohexene Chemical compound CC1=CC(=C)CCC1 LJNIRZXCJFJLRC-UHFFFAOYSA-N 0.000 description 3
- FRJKTQQNQDTORT-UHFFFAOYSA-N 2,3-Dimethyl-2-cyclohexen-1-one Chemical compound CC1=C(C)C(=O)CCC1 FRJKTQQNQDTORT-UHFFFAOYSA-N 0.000 description 3
- SVDKKDWANPIULS-UHFFFAOYSA-N 2-bromocyclohex-2-en-1-ol Chemical compound OC1CCCC=C1Br SVDKKDWANPIULS-UHFFFAOYSA-N 0.000 description 3
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- IFHHPGZMZLSINV-UHFFFAOYSA-N 3-(azidomethyl)-1-ethylcyclohexene Chemical compound CCC1=CC(CN=[N+]=[N-])CCC1 IFHHPGZMZLSINV-UHFFFAOYSA-N 0.000 description 3
- UORVPNKUEOFRLW-UHFFFAOYSA-N 3-ethylcyclohex-2-en-1-one Chemical compound CCC1=CC(=O)CCC1 UORVPNKUEOFRLW-UHFFFAOYSA-N 0.000 description 3
- RVTKUJWGFBADIN-UHFFFAOYSA-N 4-ethylcyclohexan-1-ol Chemical compound CCC1CCC(O)CC1 RVTKUJWGFBADIN-UHFFFAOYSA-N 0.000 description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- BMCQFFXPECPDPS-UHFFFAOYSA-N cycloheptylmethanol Chemical compound OCC1CCCCCC1 BMCQFFXPECPDPS-UHFFFAOYSA-N 0.000 description 3
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- 239000013613 expression plasmid Substances 0.000 description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- XFKLXBXAKOWFCJ-UHFFFAOYSA-N methyl 2-butylcyclopentene-1-carboxylate Chemical compound CCCCC1=C(C(=O)OC)CCC1 XFKLXBXAKOWFCJ-UHFFFAOYSA-N 0.000 description 3
- PZBBESSUKAHBHD-UHFFFAOYSA-N methyl 2-oxocyclopentane-1-carboxylate Chemical compound COC(=O)C1CCCC1=O PZBBESSUKAHBHD-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
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- ANAXDWKWZJIQLA-UHFFFAOYSA-N (2-chlorocyclohexen-1-yl)methanol Chemical compound OCC1=C(Cl)CCCC1 ANAXDWKWZJIQLA-UHFFFAOYSA-N 0.000 description 2
- INUXCMRSNBOSFP-UHFFFAOYSA-N (2-ethylcyclohex-2-en-1-yl)methanol Chemical compound CCC1=CCCCC1CO INUXCMRSNBOSFP-UHFFFAOYSA-N 0.000 description 2
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- DVNZWWVLJACYBN-UHFFFAOYSA-N 1-(2,3-dimethylcyclohex-2-en-1-yl)-3-(2-hydroxyethyl)thiourea Chemical compound CC1=C(C)C(NC(=S)NCCO)CCC1 DVNZWWVLJACYBN-UHFFFAOYSA-N 0.000 description 2
- ARTALHJTUZXKBU-UHFFFAOYSA-N 1-(2-bromocyclohex-2-en-1-yl)-3-(2-hydroxyethyl)thiourea Chemical compound OCCNC(=S)NC1CCCC=C1Br ARTALHJTUZXKBU-UHFFFAOYSA-N 0.000 description 2
- DDEASLNLUCSTGA-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-(2-methylcyclohex-2-en-1-yl)thiourea Chemical compound CC1=CCCCC1NC(=S)NCCO DDEASLNLUCSTGA-UHFFFAOYSA-N 0.000 description 2
- JKKKTRYQOVZTLE-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-(2-propylcyclohex-2-en-1-yl)thiourea Chemical compound CCCC1=CCCCC1NC(=S)NCCO JKKKTRYQOVZTLE-UHFFFAOYSA-N 0.000 description 2
- HRQPDSXXSJSJDE-IUCAKERBSA-N 1-(2-hydroxyethyl)-3-[(1s,3s)-3-methylcyclohexyl]thiourea Chemical compound C[C@H]1CCC[C@H](NC(=S)NCCO)C1 HRQPDSXXSJSJDE-IUCAKERBSA-N 0.000 description 2
- PFGMKEUVHIWSDI-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-[(2-methylcyclohex-2-en-1-yl)methyl]thiourea Chemical compound CC1=CCCCC1CNC(=S)NCCO PFGMKEUVHIWSDI-UHFFFAOYSA-N 0.000 description 2
- CZCRXCUTDTTYSW-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-[(2-methylcyclohexen-1-yl)methyl]thiourea Chemical compound CC1=C(CNC(=S)NCCO)CCCC1 CZCRXCUTDTTYSW-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/10—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/08—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/14—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/794,874 US6534542B2 (en) | 2001-02-27 | 2001-02-27 | (2-hydroxy)ethyl-thioureas useful as modulators of α2B adrenergic receptors |
| PCT/US2002/005021 WO2002068384A2 (en) | 2001-02-27 | 2002-02-19 | (2-hydroxy)ethyl-thioureas useful as modulators of alpha2b adrenergic receptors |
Publications (3)
| Publication Number | Publication Date |
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| JP2004524312A JP2004524312A (ja) | 2004-08-12 |
| JP2004524312A5 JP2004524312A5 (enExample) | 2005-12-22 |
| JP4159363B2 true JP4159363B2 (ja) | 2008-10-01 |
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| JP2002567898A Expired - Fee Related JP4159363B2 (ja) | 2001-02-27 | 2002-02-19 | α２Ｂアドレナリン受容体の調節剤として有用な（２−ヒドロキシ）エチル−チオウレア |
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| Country | Link |
|---|---|
| US (1) | US6534542B2 (enExample) |
| EP (1) | EP1381593A2 (enExample) |
| JP (1) | JP4159363B2 (enExample) |
| AU (1) | AU2002242203B2 (enExample) |
| CA (1) | CA2439838C (enExample) |
| WO (1) | WO2002068384A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105531251A (zh) * | 2013-09-12 | 2016-04-27 | 信越化学工业株式会社 | 用于制备环薰衣草醇及其衍生物的方法 |
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| US20060280774A1 (en) * | 1995-06-02 | 2006-12-14 | Allergan, Inc. | Compositions and methods for treating glaucoma |
| US5869079A (en) * | 1995-06-02 | 1999-02-09 | Oculex Pharmaceuticals, Inc. | Formulation for controlled release of drugs by combining hydrophilic and hydrophobic agents |
| US6329369B1 (en) * | 1997-12-04 | 2001-12-11 | Allergan Sales, Inc. | Methods of treating pain and other conditions |
| US6726918B1 (en) | 2000-07-05 | 2004-04-27 | Oculex Pharmaceuticals, Inc. | Methods for treating inflammation-mediated conditions of the eye |
| ATE306951T1 (de) | 2000-11-29 | 2005-11-15 | Allergan Inc | Verhinderung von transplantatabstossung im auge |
| US7276522B2 (en) * | 2002-05-21 | 2007-10-02 | Allergan, Inc. | 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones, 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds |
| US7358269B2 (en) | 2002-05-21 | 2008-04-15 | Allergan, Inc. | 2-((2-Thioxo-2,3-dihydro-1H-imidazol-4-yl)methyl)-3,4-dihydronapthalen-1(2H)-one |
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| US2161772A (en) * | 1936-04-17 | 1939-06-06 | Monsanto Chemicals | Phenol stabilization |
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| US5212176A (en) | 1990-06-29 | 1993-05-18 | Abbott Laboratories | R(+)-terazosin |
| US5580892A (en) * | 1993-10-22 | 1996-12-03 | Allergan | Method for using 2-(2-alkylphenylamino)-oxazolines as adrenergic agents |
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2001
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2002
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- 2002-02-19 EP EP02707824A patent/EP1381593A2/en not_active Withdrawn
- 2002-02-19 JP JP2002567898A patent/JP4159363B2/ja not_active Expired - Fee Related
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105531251A (zh) * | 2013-09-12 | 2016-04-27 | 信越化学工业株式会社 | 用于制备环薰衣草醇及其衍生物的方法 |
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| CA2439838C (en) | 2012-01-24 |
| EP1381593A2 (en) | 2004-01-21 |
| JP2004524312A (ja) | 2004-08-12 |
| AU2002242203B2 (en) | 2007-01-18 |
| WO2002068384A3 (en) | 2003-03-06 |
| WO2002068384A2 (en) | 2002-09-06 |
| CA2439838A1 (en) | 2002-09-06 |
| US6534542B2 (en) | 2003-03-18 |
| US20020161051A1 (en) | 2002-10-31 |
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