JP2015521994A5 - - Google Patents
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- Publication number
- JP2015521994A5 JP2015521994A5 JP2015519224A JP2015519224A JP2015521994A5 JP 2015521994 A5 JP2015521994 A5 JP 2015521994A5 JP 2015519224 A JP2015519224 A JP 2015519224A JP 2015519224 A JP2015519224 A JP 2015519224A JP 2015521994 A5 JP2015521994 A5 JP 2015521994A5
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- compound
- following general
- phenylimidazo
- maleate
- 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 description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000002367 halogens Chemical group 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- 208000004454 Hyperalgesia Diseases 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000035154 Hyperesthesia Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 206010053552 allodynia Diseases 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- 229910052799 carbon Inorganic materials 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
- 150000004820 halides Chemical class 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain 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
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 1
- BYTUXEPINODQIE-BTJKTKAUSA-N (z)-but-2-enedioic acid;4-[(2-phenylimidazo[2,1-b][1,3]thiazol-6-yl)methyl]morpholine Chemical compound OC(=O)\C=C/C(O)=O.C=1N2C=C(C=3C=CC=CC=3)SC2=NC=1CN1CCOCC1 BYTUXEPINODQIE-BTJKTKAUSA-N 0.000 claims 1
- DTEALRIIJSHRAH-BTJKTKAUSA-N (z)-but-2-enedioic acid;6-[(4-methylpiperazin-1-yl)methyl]-2-pyridin-4-ylimidazo[2,1-b][1,3]thiazole Chemical compound OC(=O)\C=C/C(O)=O.C1CN(C)CCN1CC1=CN(C=C(S2)C=3C=CN=CC=3)C2=N1 DTEALRIIJSHRAH-BTJKTKAUSA-N 0.000 claims 1
- ARQBNHFEPVXOMF-UHFFFAOYSA-N 2-(azepan-1-ylmethyl)-6-phenylimidazo[2,1-b][1,3]thiazole Chemical compound C=1N2C=C(C=3C=CC=CC=3)N=C2SC=1CN1CCCCCC1 ARQBNHFEPVXOMF-UHFFFAOYSA-N 0.000 claims 1
- YAEAAMWSBICPFO-UHFFFAOYSA-N 2-phenyl-6-(2-pyrrolidin-1-ylethoxymethyl)imidazo[2,1-b][1,3]thiazole Chemical compound C=1N2C=C(C=3C=CC=CC=3)SC2=NC=1COCCN1CCCC1 YAEAAMWSBICPFO-UHFFFAOYSA-N 0.000 claims 1
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 claims 1
- FYHYIXRUPSKLMV-UHFFFAOYSA-N 6-(azepan-1-ylmethyl)-2-phenylimidazo[2,1-b][1,3]thiazole Chemical compound C=1N2C=C(C=3C=CC=CC=3)SC2=NC=1CN1CCCCCC1 FYHYIXRUPSKLMV-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- UPIDTADXSUKATL-BTJKTKAUSA-N C(\C=C/C(=O)O)(=O)O.C1(=CC=CC=C1)C1=CN2C(S1)=NC(=C2)CN2CCC(CC2)C2(CC=CC=C2)O Chemical compound C(\C=C/C(=O)O)(=O)O.C1(=CC=CC=C1)C1=CN2C(S1)=NC(=C2)CN2CCC(CC2)C2(CC=CC=C2)O UPIDTADXSUKATL-BTJKTKAUSA-N 0.000 claims 1
- QXMBZDVVQAOOPK-UHFFFAOYSA-N CN1CCN(CC2=CN3C=C(SC3=N2)C2=CC=C(F)C=C2)CC1 Chemical compound CN1CCN(CC2=CN3C=C(SC3=N2)C2=CC=C(F)C=C2)CC1 QXMBZDVVQAOOPK-UHFFFAOYSA-N 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000020358 Learning disease Diseases 0.000 claims 1
- 102000004895 Lipoproteins Human genes 0.000 claims 1
- 108090001030 Lipoproteins Proteins 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- XGRAPXACEKOCRT-BTJKTKAUSA-N OC(=O)\C=C/C(O)=O.C1CN(C)CCN1CCc1cn2cc(-c3ccccc3)sc2n1 Chemical compound OC(=O)\C=C/C(O)=O.C1CN(C)CCN1CCc1cn2cc(-c3ccccc3)sc2n1 XGRAPXACEKOCRT-BTJKTKAUSA-N 0.000 claims 1
- AJWBRSGXCNIGOP-BTJKTKAUSA-N OC(=O)\C=C/C(O)=O.C1CN(C)CCN1Cc1cn2cc(-c3ccccc3)nc2s1 Chemical compound OC(=O)\C=C/C(O)=O.C1CN(C)CCN1Cc1cn2cc(-c3ccccc3)nc2s1 AJWBRSGXCNIGOP-BTJKTKAUSA-N 0.000 claims 1
- QVZIDIPSEVHZEZ-BTJKTKAUSA-N OC(=O)\C=C/C(O)=O.C1CN(C)CCN1Cc1cn2cc(-c3ccccc3)sc2n1 Chemical compound OC(=O)\C=C/C(O)=O.C1CN(C)CCN1Cc1cn2cc(-c3ccccc3)sc2n1 QVZIDIPSEVHZEZ-BTJKTKAUSA-N 0.000 claims 1
- KTCLXNOFSHKYFS-BTJKTKAUSA-N OC(=O)\C=C/C(O)=O.C1CN(C)CCN1Cc1cn2nc(-c3ccccc3)sc2n1 Chemical compound OC(=O)\C=C/C(O)=O.C1CN(C)CCN1Cc1cn2nc(-c3ccccc3)sc2n1 KTCLXNOFSHKYFS-BTJKTKAUSA-N 0.000 claims 1
- KCSRUKZDSOCIJX-BTJKTKAUSA-N OC(=O)\C=C/C(O)=O.s1c2nc(COCCN3CCCCCC3)cn2cc1-c1ccccc1 Chemical compound OC(=O)\C=C/C(O)=O.s1c2nc(COCCN3CCCCCC3)cn2cc1-c1ccccc1 KCSRUKZDSOCIJX-BTJKTKAUSA-N 0.000 claims 1
- MAHJNRSAEXKCTD-BTJKTKAUSA-N OC(=O)\C=C/C(O)=O.s1c2nc(COCCN3CCCCCC3)cn2nc1-c1ccccc1 Chemical compound OC(=O)\C=C/C(O)=O.s1c2nc(COCCN3CCCCCC3)cn2nc1-c1ccccc1 MAHJNRSAEXKCTD-BTJKTKAUSA-N 0.000 claims 1
- MBDIAHGXHKDYIR-BTJKTKAUSA-N OC(=O)\C=C/C(O)=O.s1c2nc(COCCN3CCOCC3)cn2cc1-c1ccccc1 Chemical compound OC(=O)\C=C/C(O)=O.s1c2nc(COCCN3CCOCC3)cn2cc1-c1ccccc1 MBDIAHGXHKDYIR-BTJKTKAUSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 230000005856 abnormality Effects 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 229940025084 amphetamine Drugs 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- -1 boronic acid cyclic ester Chemical class 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 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
- 239000001257 hydrogen Substances 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 201000003723 learning disability Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 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
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 108010085082 sigma receptors Proteins 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 0 CC(C)(CN(*)*)*CC(C)(C)c([s]1)b[n]2c1nc(*)c2 Chemical compound CC(C)(CN(*)*)*CC(C)(C)c([s]1)b[n]2c1nc(*)c2 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12382269.4A EP2682395A1 (en) | 2012-07-04 | 2012-07-04 | Imidazo[2,1-b]thiazole derivatives, their preparation and use as medicaments |
| EP12382269.4 | 2012-07-04 | ||
| PCT/EP2013/064113 WO2014006130A1 (en) | 2012-07-04 | 2013-07-04 | IMIDAZO[2,1-b]THIAZOLE DERIVATIVES, THEIR PREPARATION AND USE AS MEDICAMENTS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015521994A JP2015521994A (ja) | 2015-08-03 |
| JP2015521994A5 true JP2015521994A5 (cg-RX-API-DMAC7.html) | 2017-07-27 |
| JP6401156B2 JP6401156B2 (ja) | 2018-10-03 |
Family
ID=48741189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015519224A Expired - Fee Related JP6401156B2 (ja) | 2012-07-04 | 2013-07-04 | イミダゾ［２，１−ｂ］チアゾール誘導体、その製造方法、および医薬品としての使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9617281B2 (cg-RX-API-DMAC7.html) |
| EP (2) | EP2682395A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6401156B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN104520304B (cg-RX-API-DMAC7.html) |
| CA (1) | CA2878339A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2607183T3 (cg-RX-API-DMAC7.html) |
| IN (1) | IN2015MN00068A (cg-RX-API-DMAC7.html) |
| MX (1) | MX2015000056A (cg-RX-API-DMAC7.html) |
| PT (1) | PT2870164T (cg-RX-API-DMAC7.html) |
| WO (1) | WO2014006130A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017121645A1 (en) * | 2016-01-15 | 2017-07-20 | Laboratorios Del Dr. Esteve, S.A. | 3-ethyl-3-phenylazepane derivatives having multimodal activity against pain |
| WO2020127735A1 (en) * | 2018-12-20 | 2020-06-25 | Intervet International B.V. | New methods of producing (2-amino-4-[6-(4-fluorophenyl)-2-[(4-methyl-1-piperazinyl)methyl]imidazo[2,1-b]thiazol-5-yl]-pyrimidine |
| CN117203211B (zh) * | 2021-11-29 | 2025-08-19 | 中国海洋大学 | 咪唑并噻唑衍生物及其制备方法与应用 |
| WO2024105225A1 (en) | 2022-11-18 | 2024-05-23 | Universitat De Barcelona | Synergistic combinations of a sigma receptor 1 (s1r) antagonist and a soluble epoxide hydrolase inhibitor (sehi) and their use in the treatment of pain |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH621126A5 (cg-RX-API-DMAC7.html) | 1974-02-07 | 1981-01-15 | Plantex Ltd | |
| DE2823686A1 (de) * | 1978-05-31 | 1979-12-06 | Bayer Ag | Imidazo eckige klammer auf 2.1-b eckige klammer zu eckige klammer auf 1.3.4 eckige klammer zu -thiadiazole |
| DE3329621A1 (de) * | 1983-08-17 | 1985-02-28 | Bayer Ag, 5090 Leverkusen | Aminoalkyl-imidazothiadiazol-alkencarbonsaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln |
| US7229480B2 (en) | 2004-02-13 | 2007-06-12 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| EP1634873A1 (en) | 2004-08-27 | 2006-03-15 | Laboratorios Del Dr. Esteve, S.A. | Sigma receptor inhibitors |
| BRPI0514692A (pt) * | 2004-08-27 | 2008-06-17 | Esteve Labor Dr | inibidores do receptor sigma |
| US20060156484A1 (en) | 2005-01-14 | 2006-07-20 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| CN101277965A (zh) * | 2005-08-04 | 2008-10-01 | 西特里斯药业公司 | 作为SIRTUIN调节化合物的咪唑并[2,1-b]噻唑衍生物 |
| AU2006278397B2 (en) | 2005-08-04 | 2013-01-17 | Sirtris Pharmaceuticals, Inc. | Oxazolopyridine derivatives as sirtuin modulators |
| EP1829869A1 (en) | 2006-03-02 | 2007-09-05 | Laboratorios Del Dr. Esteve, S.A. | 4,5,6,7-Tetrahydrobenzo[b]thiophene derivatives and their use as sigma receptor ligands |
| EP1847542A1 (en) | 2006-04-21 | 2007-10-24 | Laboratorios del Dr. Esteve S.A. | Spiro[benzopyran] or spiro[benzofuran] derivatives which inhibit the sigma receptor |
| EP1982714A1 (en) * | 2007-04-16 | 2008-10-22 | Laboratorios del Dr. Esteve S.A. | Pyrano-pyrazole-amines |
| AU2008254588B2 (en) | 2007-05-21 | 2013-01-17 | Sgx Pharmaceuticals, Inc. | Heterocyclic kinase modulators |
| PT2193133E (pt) | 2007-09-27 | 2015-10-22 | Fundación Ct Nac De Investigaciones Oncológicas Carlos Iii | Imidazolotiadiazóis para utilização como inibidores de proteína quinases |
| EP2053052A1 (en) * | 2007-10-23 | 2009-04-29 | Laboratorios del Dr. Esteve S.A. | Process for the preparation of 6-substituted imidazo[2,1-b]thiazole-5-sulfonyl halide |
| EP2070933A1 (en) | 2007-12-07 | 2009-06-17 | Laboratorios del Dr. Esteve S.A. | Tricyclic triazolic compounds |
| EP2395003A1 (en) * | 2010-05-27 | 2011-12-14 | Laboratorios Del. Dr. Esteve, S.A. | Pyrazole compounds as sigma receptor inhibitors |
-
2012
- 2012-07-04 EP EP12382269.4A patent/EP2682395A1/en not_active Withdrawn
-
2013
- 2013-07-04 WO PCT/EP2013/064113 patent/WO2014006130A1/en not_active Ceased
- 2013-07-04 CA CA2878339A patent/CA2878339A1/en not_active Abandoned
- 2013-07-04 JP JP2015519224A patent/JP6401156B2/ja not_active Expired - Fee Related
- 2013-07-04 ES ES13732996.7T patent/ES2607183T3/es active Active
- 2013-07-04 EP EP13732996.7A patent/EP2870164B1/en not_active Not-in-force
- 2013-07-04 PT PT137329967T patent/PT2870164T/pt unknown
- 2013-07-04 MX MX2015000056A patent/MX2015000056A/es unknown
- 2013-07-04 CN CN201380041504.1A patent/CN104520304B/zh not_active Expired - Fee Related
- 2013-07-04 IN IN68MUN2015 patent/IN2015MN00068A/en unknown
- 2013-07-04 US US14/412,257 patent/US9617281B2/en not_active Expired - Fee Related
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