JP2005516006A5 - - Google Patents
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- Publication number
- JP2005516006A5 JP2005516006A5 JP2003550790A JP2003550790A JP2005516006A5 JP 2005516006 A5 JP2005516006 A5 JP 2005516006A5 JP 2003550790 A JP2003550790 A JP 2003550790A JP 2003550790 A JP2003550790 A JP 2003550790A JP 2005516006 A5 JP2005516006 A5 JP 2005516006A5
- Authority
- JP
- Japan
- Prior art keywords
- benzothiazol
- methoxy
- morpholin
- aza
- amide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 16
- -1 tetrahydropyran-4-yl Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- KYCAEEFYFFBAAP-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.1]octane Chemical compound C1C2CCN1CCN2 KYCAEEFYFFBAAP-UHFFFAOYSA-N 0.000 claims 3
- KVYOWXUQJLOCIA-UHFFFAOYSA-N 1-oxa-8-azaspiro[4.5]decane Chemical compound C1CCOC21CCNCC2 KVYOWXUQJLOCIA-UHFFFAOYSA-N 0.000 claims 3
- HHIOFHJYOIVJJK-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decan-1-one Chemical compound O=C1NCCC11CCNCC1 HHIOFHJYOIVJJK-UHFFFAOYSA-N 0.000 claims 3
- DIQOUXNTSMWQSA-UHFFFAOYSA-N 2-oxa-5-azabicyclo[2.2.1]heptane Chemical compound C1OC2CNC1C2 DIQOUXNTSMWQSA-UHFFFAOYSA-N 0.000 claims 3
- JNYWVERKQKRXSL-UHFFFAOYSA-N 2-oxa-5-azabicyclo[2.2.2]octane Chemical compound C1NC2CCC1OC2 JNYWVERKQKRXSL-UHFFFAOYSA-N 0.000 claims 3
- GYLMCBOAXJVARF-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptane Chemical compound C1C2CCC1NC2 GYLMCBOAXJVARF-UHFFFAOYSA-N 0.000 claims 3
- KPUSZZFAYGWAHZ-UHFFFAOYSA-N 3-azabicyclo[2.2.2]octane Chemical compound C1CC2CCC1NC2 KPUSZZFAYGWAHZ-UHFFFAOYSA-N 0.000 claims 3
- CJQNJRRDTPULTL-UHFFFAOYSA-N 3-azabicyclo[3.2.1]octane Chemical compound C1C2CCC1CNC2 CJQNJRRDTPULTL-UHFFFAOYSA-N 0.000 claims 3
- LIZKZVQBLDHKCY-UHFFFAOYSA-N 3-azaspiro[5.5]undecane Chemical compound C1CCCCC21CCNCC2 LIZKZVQBLDHKCY-UHFFFAOYSA-N 0.000 claims 3
- CHRAJVQLWOMYQI-UHFFFAOYSA-N 5,8,8-trimethyl-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1(C)C2(C)C CHRAJVQLWOMYQI-UHFFFAOYSA-N 0.000 claims 3
- POOPWPIOIMBTOH-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1O2 POOPWPIOIMBTOH-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- YYMCYJLIYNNOMK-UHFFFAOYSA-N N-normethyltropine Natural products C1C(O)CC2CCC1N2 YYMCYJLIYNNOMK-UHFFFAOYSA-N 0.000 claims 3
- AXMNGEUJXLXFRY-UHFFFAOYSA-N azaspirodecane Chemical compound C1CCCC21CCNCC2 AXMNGEUJXLXFRY-UHFFFAOYSA-N 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- FLBNPQJRBGWRKR-UHFFFAOYSA-N 4-(methanesulfonamidomethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)piperidine-1-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC(CNS(C)(=O)=O)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 FLBNPQJRBGWRKR-UHFFFAOYSA-N 0.000 claims 2
- IFCMUPMBYYVMGO-CYBMUJFWSA-N 4-[(1r)-1-hydroxyethyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)piperidine-1-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC(CC3)[C@@H](C)O)=NC=2C(OC)=CC=C1N1CCOCC1 IFCMUPMBYYVMGO-CYBMUJFWSA-N 0.000 claims 2
- IFCMUPMBYYVMGO-ZDUSSCGKSA-N 4-[(1s)-1-hydroxyethyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)piperidine-1-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC(CC3)[C@H](C)O)=NC=2C(OC)=CC=C1N1CCOCC1 IFCMUPMBYYVMGO-ZDUSSCGKSA-N 0.000 claims 2
- HIONBFAFOGSFGW-UHFFFAOYSA-N 4-benzyl-4-(hydroxymethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)piperidine-1-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC(CO)(CC=4C=CC=CC=4)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 HIONBFAFOGSFGW-UHFFFAOYSA-N 0.000 claims 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims 2
- QFLBKCIGHQIBLY-HDJSIYSDSA-N C1=2SC(NC(=O)N(C)[C@@H]3CC[C@@H](O)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 Chemical compound C1=2SC(NC(=O)N(C)[C@@H]3CC[C@@H](O)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 QFLBKCIGHQIBLY-HDJSIYSDSA-N 0.000 claims 2
- QFLBKCIGHQIBLY-OKILXGFUSA-N C1=2SC(NC(=O)N(C)[C@H]3CC[C@@H](O)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 Chemical compound C1=2SC(NC(=O)N(C)[C@H]3CC[C@@H](O)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 QFLBKCIGHQIBLY-OKILXGFUSA-N 0.000 claims 2
- QUYUZBGIPLRICV-GASCZTMLSA-N C1C[C@@H](OC)CC[C@H]1N(C)C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 Chemical compound C1C[C@@H](OC)CC[C@H]1N(C)C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 QUYUZBGIPLRICV-GASCZTMLSA-N 0.000 claims 2
- 229960005305 adenosine Drugs 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- WJJHANCJJOEBQD-UHFFFAOYSA-N n-(4-chloro-7-piperidin-1-yl-1,3-benzothiazol-2-yl)-4-hydroxy-4-[(4-methylphenyl)methyl]piperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(C(=O)NC=2SC3=C(N4CCCCC4)C=CC(Cl)=C3N=2)CC1 WJJHANCJJOEBQD-UHFFFAOYSA-N 0.000 claims 2
- IYFPKFFZLUBDGN-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-1-oxa-8-azaspiro[4.5]decane-8-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC4(OCCC4)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 IYFPKFFZLUBDGN-UHFFFAOYSA-N 0.000 claims 2
- AJUXKMMSLQDKII-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC4(C(NCC4)=O)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 AJUXKMMSLQDKII-UHFFFAOYSA-N 0.000 claims 2
- YSIZCVKNKKXRDX-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-methyl-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC4(C(N(C)CC4)=O)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 YSIZCVKNKKXRDX-UHFFFAOYSA-N 0.000 claims 2
- HURFKWOYYGOEDL-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxamide Chemical compound C1=2SC(NC(=O)N3C4CCC(OC4)C3)=NC=2C(OC)=CC=C1N1CCOCC1 HURFKWOYYGOEDL-UHFFFAOYSA-N 0.000 claims 2
- YXKZXASPEPLXDA-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3-azabicyclo[2.2.2]octane-3-carboxamide Chemical compound C1=2SC(NC(=O)N3C4CCC(CC4)C3)=NC=2C(OC)=CC=C1N1CCOCC1 YXKZXASPEPLXDA-UHFFFAOYSA-N 0.000 claims 2
- NVJVAOWILSOJGP-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3-azaspiro[5.5]undecane-3-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC4(CCCCC4)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 NVJVAOWILSOJGP-UHFFFAOYSA-N 0.000 claims 2
- WOJYLKMRSKGFTI-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-8-azaspiro[4.5]decane-8-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC4(CCCC4)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 WOJYLKMRSKGFTI-UHFFFAOYSA-N 0.000 claims 2
- LQTHHEQEIWKZGY-UHFFFAOYSA-N n-(4-methoxy-7-piperidin-1-yl-1,3-benzothiazol-2-yl)-1-oxa-8-azaspiro[4.5]decane-8-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC4(OCCC4)CC3)=NC=2C(OC)=CC=C1N1CCCCC1 LQTHHEQEIWKZGY-UHFFFAOYSA-N 0.000 claims 2
- AQNQGBUEVCAVML-UHFFFAOYSA-N oxazepane Chemical compound C1CCNOCC1 AQNQGBUEVCAVML-UHFFFAOYSA-N 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- IIKFXOLJMNWWCH-UHFFFAOYSA-N piperidine-1,4-dicarboxylic acid Chemical compound OC(=O)C1CCN(C(O)=O)CC1 IIKFXOLJMNWWCH-UHFFFAOYSA-N 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- CKOFIRBMZAAFLM-OLZOCXBDSA-N (1r,4s)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3-azabicyclo[2.2.1]heptane-3-carboxamide Chemical compound N1([C@@]2([H])CC[C@](C2)(C1)[H])C(=O)NC(SC1=2)=NC1=C(OC)C=CC=2N1CCOCC1 CKOFIRBMZAAFLM-OLZOCXBDSA-N 0.000 claims 1
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 1
- VGMHMYUFRKBDIS-WHFBIAKZSA-N (1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylic acid Chemical compound C1[C@@H]2N(C(=O)O)C[C@H]1OC2 VGMHMYUFRKBDIS-WHFBIAKZSA-N 0.000 claims 1
- XBKJNVIPKGZBKC-RYUDHWBXSA-N (1s,4s)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxamide Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(=O)NC(SC1=2)=NC1=C(OC)C=CC=2N1CCOCC1 XBKJNVIPKGZBKC-RYUDHWBXSA-N 0.000 claims 1
- RXNXSFVNJXCUGB-LYNSQETBSA-N (5r)-5,8,8-trimethyl-3-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound C1N(C(O)=O)C[C@]2(C)CCC1C2(C)C RXNXSFVNJXCUGB-LYNSQETBSA-N 0.000 claims 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 1
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 1
- CYOQYWSVWLVUNQ-UHFFFAOYSA-N 1-(4,4-difluorocyclohexyl)-3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-1-methylurea Chemical compound C1=2SC(NC(=O)N(C)C3CCC(F)(F)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 CYOQYWSVWLVUNQ-UHFFFAOYSA-N 0.000 claims 1
- QUYUZBGIPLRICV-UHFFFAOYSA-N 1-(4-methoxycyclohexyl)-3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-1-methylurea Chemical compound C1CC(OC)CCC1N(C)C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 QUYUZBGIPLRICV-UHFFFAOYSA-N 0.000 claims 1
- NSGALPBZLUIXNP-UHFFFAOYSA-N 1-cycloheptyl-3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-1-methylurea Chemical compound C1=2SC(NC(=O)N(C)C3CCCCCC3)=NC=2C(OC)=CC=C1N1CCOCC1 NSGALPBZLUIXNP-UHFFFAOYSA-N 0.000 claims 1
- ZMZFUVWCTYCGGP-UHFFFAOYSA-N 1-cyclohexyl-3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-1-methylurea Chemical compound C1=2SC(NC(=O)N(C)C3CCCCC3)=NC=2C(OC)=CC=C1N1CCOCC1 ZMZFUVWCTYCGGP-UHFFFAOYSA-N 0.000 claims 1
- CATYLCHNNIEDLB-UHFFFAOYSA-N 1-cyclopentyl-3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-1-methylurea Chemical compound C1=2SC(NC(=O)N(C)C3CCCC3)=NC=2C(OC)=CC=C1N1CCOCC1 CATYLCHNNIEDLB-UHFFFAOYSA-N 0.000 claims 1
- FBWTZOLFAPRERY-UHFFFAOYSA-N 3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-1-methyl-1-(oxan-4-yl)urea Chemical compound C1=2SC(NC(=O)N(C)C3CCOCC3)=NC=2C(OC)=CC=C1N1CCOCC1 FBWTZOLFAPRERY-UHFFFAOYSA-N 0.000 claims 1
- YLHLDUAMNQPUTF-UHFFFAOYSA-N 4-benzyl-n-(4-chloro-7-piperidin-1-yl-1,3-benzothiazol-2-yl)piperidine-1-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC(CC=4C=CC=CC=4)CC3)=NC=2C(Cl)=CC=C1N1CCCCC1 YLHLDUAMNQPUTF-UHFFFAOYSA-N 0.000 claims 1
- KQPHMMBVFBMPPA-UHFFFAOYSA-N 4-chloro-7-piperidin-1-yl-1,3-benzothiazol-2-amine Chemical compound C=12SC(N)=NC2=C(Cl)C=CC=1N1CCCCC1 KQPHMMBVFBMPPA-UHFFFAOYSA-N 0.000 claims 1
- 102000009346 Adenosine receptors Human genes 0.000 claims 1
- 108050000203 Adenosine receptors Proteins 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- QUYUZBGIPLRICV-SHTZXODSSA-N C1C[C@@H](OC)CC[C@@H]1N(C)C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N(C)C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 QUYUZBGIPLRICV-SHTZXODSSA-N 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 206010013654 Drug abuse Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010021143 Hypoxia Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010038687 Respiratory distress Diseases 0.000 claims 1
- 229940025084 amphetamine Drugs 0.000 claims 1
- 229940125681 anticonvulsant agent Drugs 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 239000000164 antipsychotic agent Substances 0.000 claims 1
- 229940005529 antipsychotics Drugs 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 229930003827 cannabinoid Natural products 0.000 claims 1
- 239000003557 cannabinoid Substances 0.000 claims 1
- 229940065144 cannabinoids Drugs 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 229940045200 cardioprotective agent Drugs 0.000 claims 1
- 239000012659 cardioprotective agent Substances 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 229960004756 ethanol Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000007954 hypoxia Effects 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 229940035363 muscle relaxants Drugs 0.000 claims 1
- 239000003158 myorelaxant agent Substances 0.000 claims 1
- LOCJAPBORDSQSM-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-1,4-diazabicyclo[3.2.1]octane-4-carboxamide Chemical compound C1=2SC(NC(=O)N3C4CCN(C4)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 LOCJAPBORDSQSM-UHFFFAOYSA-N 0.000 claims 1
- QCLZXEPFSSSFEB-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-phenylpiperazine-1-carboxamide Chemical compound C1=2SC(NC(=O)N3CCN(CC3)C=3C=CC=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 QCLZXEPFSSSFEB-UHFFFAOYSA-N 0.000 claims 1
- CDJOLCSVZMPMBZ-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)oxazepane-4-carboxamide Chemical compound C1=2SC(NC(=O)C3CNOCCC3)=NC=2C(OC)=CC=C1N1CCOCC1 CDJOLCSVZMPMBZ-UHFFFAOYSA-N 0.000 claims 1
- IASFCNWEKKVPAZ-UHFFFAOYSA-N n-(4-methoxy-7-piperidin-1-yl-1,3-benzothiazol-2-yl)-4-methyl-3-oxopiperazine-1-carboxamide Chemical compound C1=2SC(NC(=O)N3CC(=O)N(C)CC3)=NC=2C(OC)=CC=C1N1CCCCC1 IASFCNWEKKVPAZ-UHFFFAOYSA-N 0.000 claims 1
- 230000004112 neuroprotection Effects 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 229940005483 opioid analgesics Drugs 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 230000036407 pain Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 229940125723 sedative agent Drugs 0.000 claims 1
- 239000000932 sedative agent Substances 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01129228 | 2001-12-10 | ||
| PCT/EP2002/013761 WO2003049741A1 (en) | 2001-12-10 | 2002-12-05 | Ureas of 2-aminobenzothiazoles as adenosine modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005516006A JP2005516006A (ja) | 2005-06-02 |
| JP2005516006A5 true JP2005516006A5 (cg-RX-API-DMAC7.html) | 2005-12-22 |
| JP4245483B2 JP4245483B2 (ja) | 2009-03-25 |
Family
ID=8179478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003550790A Expired - Fee Related JP4245483B2 (ja) | 2001-12-10 | 2002-12-05 | アデノシン調節薬としての２−アミノベンゾチアゾールの尿素 |
Country Status (20)
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2251419C2 (ru) * | 2000-06-21 | 2005-05-10 | Ф. Хоффманн-Ля Рош Аг | Производные бензотиазола |
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| US45615A (en) * | 1864-12-27 | Improvement in cultivators | ||
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| US6727247B2 (en) * | 2001-12-10 | 2004-04-27 | Hoffman-La Roche Inc. | Substituted benzothiazole amide derivatives |
-
2002
- 2002-12-03 US US10/308,338 patent/US6727247B2/en not_active Expired - Fee Related
- 2002-12-05 BR BR0214825-0A patent/BR0214825A/pt not_active Application Discontinuation
- 2002-12-05 PE PE2002001174A patent/PE20030759A1/es not_active Application Discontinuation
- 2002-12-05 CN CNA028246543A patent/CN1602196A/zh active Pending
- 2002-12-05 PA PA20028559901A patent/PA8559901A1/es unknown
- 2002-12-05 EP EP02804578A patent/EP1455792B1/en not_active Expired - Lifetime
- 2002-12-05 AT AT02804578T patent/ATE359792T1/de active
- 2002-12-05 JP JP2003550790A patent/JP4245483B2/ja not_active Expired - Fee Related
- 2002-12-05 TW TW091135281A patent/TW200409628A/zh unknown
- 2002-12-05 WO PCT/EP2002/013761 patent/WO2003049741A1/en not_active Ceased
- 2002-12-05 PL PL02371063A patent/PL371063A1/xx not_active Application Discontinuation
- 2002-12-05 CA CA002469596A patent/CA2469596A1/en not_active Abandoned
- 2002-12-05 AU AU2002356626A patent/AU2002356626B2/en not_active Ceased
- 2002-12-05 MX MXPA04005444A patent/MXPA04005444A/es active IP Right Grant
- 2002-12-05 KR KR1020047008868A patent/KR100659793B1/ko not_active Expired - Fee Related
- 2002-12-05 DE DE60219682T patent/DE60219682T2/de not_active Expired - Lifetime
- 2002-12-05 ES ES02804578T patent/ES2283652T3/es not_active Expired - Lifetime
- 2002-12-05 RU RU2004121166/15A patent/RU2311905C2/ru not_active IP Right Cessation
- 2002-12-06 AR ARP020104739A patent/AR037731A1/es unknown
- 2002-12-09 GT GT200200266A patent/GT200200266A/es unknown
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- 2003-10-23 US US10/691,770 patent/US7019001B2/en not_active Expired - Fee Related
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