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 (https=) | 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)
| Country | Link |
|---|---|
| US (2) | US6727247B2 (https=) |
| EP (1) | EP1455792B1 (https=) |
| JP (1) | JP4245483B2 (https=) |
| KR (1) | KR100659793B1 (https=) |
| CN (1) | CN1602196A (https=) |
| AR (1) | AR037731A1 (https=) |
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| CA (1) | CA2469596A1 (https=) |
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| RU (1) | RU2311905C2 (https=) |
| TW (1) | TW200409628A (https=) |
| WO (1) | WO2003049741A1 (https=) |
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| AU2001281817B2 (en) * | 2000-06-21 | 2005-11-24 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives |
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| JPWO2004002531A1 (ja) * | 2002-06-26 | 2005-10-27 | 小野薬品工業株式会社 | 血管の収縮または拡張による疾患治療剤 |
| EP1622569B1 (en) | 2003-04-24 | 2015-12-02 | Incyte Corporation | Aza spiro alkane derivatives as inhibitors of metallproteases |
| PT1636223E (pt) | 2003-05-19 | 2008-05-06 | F Hoffmann-La Roche Ag | Derivados de benzotiazole como ligandos de receptores da adenosina |
| RU2348629C2 (ru) * | 2003-05-30 | 2009-03-10 | Ф.Хоффманн-Ля Рош Аг | Производные бензотиазола и их применение при лечении заболеваний, связанных с аденозиновыми a2a-рецепторами |
| RU2006112847A (ru) | 2003-09-19 | 2007-11-10 | Ф. Хоффманн-Ля Рош Аг (Ch) | Производные тиазолопиридина в качестве лигандов аденозинового рецептора |
| EP1677791A4 (en) | 2003-10-31 | 2007-08-15 | Takeda Pharmaceutical | NITROGENIC CONDENSED HETEROCYCLIC COMPOUNDS |
| EP1720873B1 (en) | 2004-01-08 | 2011-02-23 | F. Hoffmann-La Roche AG | Diaza-spiropiperidine derivatives |
| KR100834179B1 (ko) * | 2004-05-24 | 2008-05-30 | 에프. 호프만-라 로슈 아게 | 4-하이드록시-4-메틸-피페리딘-1-카복실산(4-메톡시-7-모폴린-4-일-벤조티아졸-2-일)-아마이드 |
| RS50574B (sr) * | 2004-05-24 | 2010-05-07 | F. Hoffmann-La Roche Ag. | (4-metoksi-7-morfolin-4-il-benzotiazol-2-il)-amid 4-hidroksi-4-metil-piperidin-1-karboksilne kiseline |
| JP5202946B2 (ja) * | 2004-07-22 | 2013-06-05 | エフ．ホフマン−ラ ロシュ アーゲー | ベンゾチアゾール誘導体 |
| CN1989117B (zh) * | 2004-07-22 | 2011-01-19 | 弗·哈夫曼-拉罗切有限公司 | 取代的苯并噻唑 |
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| WO2006099972A1 (en) | 2005-03-23 | 2006-09-28 | F. Hoffmann-La Roche Ag | Acetylenyl-pyrazolo-pvrimidine derivatives as mglur2 antagonists |
| JP5048675B2 (ja) | 2005-09-27 | 2012-10-17 | エフ．ホフマン−ラ ロシュ アーゲー | ｍＧｌｕＲ２アンタゴニストとしてのオキサジアゾリルピラゾロ−ピリミジン類 |
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| US7910108B2 (en) * | 2006-06-05 | 2011-03-22 | Incyte Corporation | Sheddase inhibitors combined with CD30-binding immunotherapeutics for the treatment of CD30 positive diseases |
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| US20110172230A1 (en) * | 2006-08-23 | 2011-07-14 | Takahiro Ishii | Urea compound or salt thereof |
| TW200833328A (en) * | 2006-12-28 | 2008-08-16 | Actelion Pharmaceuticals Ltd | 2-aza-bicyclo[3.1.0]hexane derivatives |
| JP2010522760A (ja) | 2007-03-28 | 2010-07-08 | アボット・ラボラトリーズ | カンナビノイド受容体リガンドとしての１，３−チアゾール−２（３ｈ）−イリデン化合物 |
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| MX2009012374A (es) | 2007-05-18 | 2009-12-01 | Abbott Lab | Compuestos novedosos como ligandos del receptor de canabinoides. |
| AU2008263166A1 (en) * | 2007-05-25 | 2008-12-18 | Janssen Pharmaceutica N.V. | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| US8455520B2 (en) | 2007-07-17 | 2013-06-04 | Merck Sharp & Dohme Corp. | Soluble epoxide hydrolase inhibitors, compositions containing such compounds and methods of treatment |
| US9193713B2 (en) | 2007-10-12 | 2015-11-24 | Abbvie Inc. | Compounds as cannabinoid receptor ligands |
| US9226907B2 (en) | 2008-02-01 | 2016-01-05 | Abbvie Inc. | Extended release hydrocodone acetaminophen and related methods and uses thereof |
| US8846730B2 (en) | 2008-09-08 | 2014-09-30 | Abbvie Inc. | Compounds as cannabinoid receptor ligands |
| TW201016692A (en) | 2008-09-16 | 2010-05-01 | Abbott Lab | Novel compounds as cannabinoid receptor ligands |
| US8461159B2 (en) | 2008-11-25 | 2013-06-11 | Jannsen Pharmaceutica BV | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| WO2010068452A1 (en) * | 2008-11-25 | 2010-06-17 | Janssen Pharmaceutica Nv | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| PA8854001A1 (es) | 2008-12-16 | 2010-07-27 | Abbott Lab | Compuestos novedosos como ligandos de receptores de canabinoides |
| FR2945531A1 (fr) * | 2009-05-12 | 2010-11-19 | Sanofi Aventis | Derives de 7-aza-spiro°3,5!nonane-7-carboxylates, leur preparation et leur application en therapeutique |
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| US20120083476A1 (en) | 2009-06-05 | 2012-04-05 | Janssen Pharmaceutica Nv | Heteroaryl-substituted spirocyclic diamine urea modulators of fatty acid amide hydrolase |
| WO2011021645A1 (ja) * | 2009-08-19 | 2011-02-24 | 大日本住友製薬株式会社 | ２環性ウレア誘導体、またはその薬学的に許容される塩 |
| UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
| US9605002B2 (en) * | 2012-07-18 | 2017-03-28 | University Of Notre Dame Du Lac | 5,5-heteroaromatic anti-infective compounds |
| WO2014146994A1 (en) * | 2013-03-20 | 2014-09-25 | F. Hoffmann-La Roche Ag | Urea derivatives and their use as fatty-acid binding protein (fabp) inhibitors |
| AR095570A1 (es) * | 2013-03-20 | 2015-10-28 | Hoffmann La Roche | Derivados de urea |
| JP2019533022A (ja) * | 2016-10-24 | 2019-11-14 | ユマニティ セラピューティクス，インコーポレーテッド | 化合物及びその使用 |
| EP3566055B1 (en) | 2017-01-06 | 2025-03-12 | Janssen Pharmaceutica NV | Scd inhibitor for the treatment of neurological disorders |
| CA3083000A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| WO2019141096A1 (zh) * | 2018-01-19 | 2019-07-25 | 四川科伦博泰生物医药股份有限公司 | 取代脲类化合物及其制备方法和用途 |
| WO2019183587A1 (en) | 2018-03-23 | 2019-09-26 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| CN111205244B (zh) * | 2018-11-22 | 2023-08-18 | 上海科技大学 | 噻唑并环类化合物、其制备方法、中间体和应用 |
| WO2020154571A1 (en) | 2019-01-24 | 2020-07-30 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
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| US45615A (en) * | 1864-12-27 | Improvement in cultivators | ||
| US3954766A (en) * | 1975-07-09 | 1976-05-04 | Stanford Research Institute | 1,4-Diazabicyclo[3.2.1]octanes |
| DE3374550D1 (en) | 1982-12-21 | 1987-12-23 | Johnsen Jorgensen Plastics Ltd | Dispensing container |
| DE4241013A1 (de) * | 1992-12-05 | 1994-06-09 | Boehringer Ingelheim Kg | Verwendung von 2-Amino-6-n-propyl-amino-4,5,6,7-tetrahydrobenzothiazol als Arzneimittel mit antidepressiver Wirkung |
| KR20020084116A (ko) | 2000-02-07 | 2002-11-04 | 애보트 게엠베하 운트 콤파니 카게 | 2-벤조티아졸릴 우레아 유도체 및 이의 단백질 키나제억제제로서의 용도 |
| AU2001281817B2 (en) | 2000-06-21 | 2005-11-24 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives |
| US6599901B1 (en) * | 2001-11-19 | 2003-07-29 | Hoffman-La Roche Inc. | Pyridone substituted benzothiazole derivatives |
| 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 DE DE60219682T patent/DE60219682T2/de not_active Expired - Lifetime
- 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 MX MXPA04005444A patent/MXPA04005444A/es active IP Right Grant
- 2002-12-05 WO PCT/EP2002/013761 patent/WO2003049741A1/en not_active Ceased
- 2002-12-05 CA CA002469596A patent/CA2469596A1/en not_active Abandoned
- 2002-12-05 KR KR1020047008868A patent/KR100659793B1/ko not_active Expired - Fee Related
- 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 PL PL02371063A patent/PL371063A1/xx not_active Application Discontinuation
- 2002-12-05 BR BR0214825-0A patent/BR0214825A/pt not_active Application Discontinuation
- 2002-12-05 ES ES02804578T patent/ES2283652T3/es not_active Expired - Lifetime
- 2002-12-05 AU AU2002356626A patent/AU2002356626B2/en not_active Ceased
- 2002-12-05 AT AT02804578T patent/ATE359792T1/de active
- 2002-12-05 RU RU2004121166/15A patent/RU2311905C2/ru not_active IP Right Cessation
- 2002-12-05 PE PE2002001174A patent/PE20030759A1/es not_active Application Discontinuation
- 2002-12-06 AR ARP020104739A patent/AR037731A1/es unknown
- 2002-12-09 GT GT200200266A patent/GT200200266A/es unknown
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2003
- 2003-10-23 US US10/691,770 patent/US7019001B2/en not_active Expired - Fee Related
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