JP2011519343A5 - - Google Patents
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- JP2011519343A5 JP2011519343A5 JP2010539048A JP2010539048A JP2011519343A5 JP 2011519343 A5 JP2011519343 A5 JP 2011519343A5 JP 2010539048 A JP2010539048 A JP 2010539048A JP 2010539048 A JP2010539048 A JP 2010539048A JP 2011519343 A5 JP2011519343 A5 JP 2011519343A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- chromene
- cyclobutane
- dihydrospiro
- chloro
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 522
- -1 nitro, cyano, amino Chemical group 0.000 claims description 326
- VYIBCOSBNVFEIW-UHFFFAOYSA-N 3-phenylpropanamide Chemical compound NC(=O)CCC1=CC=CC=C1 VYIBCOSBNVFEIW-UHFFFAOYSA-N 0.000 claims description 87
- 125000003118 aryl group Chemical group 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 125000001072 heteroaryl group Chemical group 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 51
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 208000002193 Pain Diseases 0.000 claims description 30
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 208000035475 disorder Diseases 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 16
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 16
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 12
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 9
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- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
- 208000011580 syndromic disease Diseases 0.000 claims description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- 230000006870 function Effects 0.000 claims description 6
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
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- QBDKYBYELHDDDG-UHFFFAOYSA-N spiro[3,4-dihydrochromene-2,1'-cyclobutane] Chemical compound C1CCC21OC1=CC=CC=C1CC2 QBDKYBYELHDDDG-UHFFFAOYSA-N 0.000 claims description 5
- UNFGQCCHVMMMRF-UHFFFAOYSA-N 2-phenylbutanamide Chemical compound CCC(C(N)=O)C1=CC=CC=C1 UNFGQCCHVMMMRF-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
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- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 230000000302 ischemic effect Effects 0.000 claims description 4
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- HCVFGRUKYVWXIF-UHFFFAOYSA-N n-(6-chloro-3,4-dihydro-2h-thiochromen-4-yl)-4-(2-cyclopentyloxy-3-methoxyphenyl)butanamide Chemical compound COC1=CC=CC(CCCC(=O)NC2C3=CC(Cl)=CC=C3SCC2)=C1OC1CCCC1 HCVFGRUKYVWXIF-UHFFFAOYSA-N 0.000 claims description 4
- UIQODYCOSLDHFU-UHFFFAOYSA-N n-(6-chlorospiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl)-2-pyridin-2-ylacetamide Chemical compound C1C(NC(=O)CC=2N=CC=CC=2)C2=CC(Cl)=CC=C2OC21CCC2 UIQODYCOSLDHFU-UHFFFAOYSA-N 0.000 claims description 4
- ABINOOJEFPZEPJ-UHFFFAOYSA-N n-(8-chlorospiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl)-2-phenylacetamide Chemical compound O1C=2C(Cl)=CC=CC=2C(NC(=O)CC=2C=CC=CC=2)CC21CCC2 ABINOOJEFPZEPJ-UHFFFAOYSA-N 0.000 claims description 4
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- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 3
- HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical compound C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 claims description 3
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- 206010012289 Dementia Diseases 0.000 claims description 3
- 201000004624 Dermatitis Diseases 0.000 claims description 3
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- 208000004232 Enteritis Diseases 0.000 claims description 3
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- 208000008589 Obesity Diseases 0.000 claims description 3
- 206010033645 Pancreatitis Diseases 0.000 claims description 3
- 208000008469 Peptic Ulcer Diseases 0.000 claims description 3
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
- 208000017442 Retinal disease Diseases 0.000 claims description 3
- 206010038923 Retinopathy Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 208000005392 Spasm Diseases 0.000 claims description 3
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- 208000024780 Urticaria Diseases 0.000 claims description 3
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- 208000009621 actinic keratosis Diseases 0.000 claims description 3
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 3
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- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 3
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- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
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- DJGARHHOHBNZQG-UHFFFAOYSA-N n-(6-chloro-3,4-dihydro-2h-thiochromen-4-yl)-3-(2-cyclopentyloxy-3-methoxyphenyl)propanamide Chemical compound COC1=CC=CC(CCC(=O)NC2C3=CC(Cl)=CC=C3SCC2)=C1OC1CCCC1 DJGARHHOHBNZQG-UHFFFAOYSA-N 0.000 claims description 3
- UOYBBAUKZUIFAF-UHFFFAOYSA-N n-(6-chlorospiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl)-3-naphthalen-1-ylpropanamide Chemical compound C1C(NC(=O)CCC=2C3=CC=CC=C3C=CC=2)C2=CC(Cl)=CC=C2OC21CCC2 UOYBBAUKZUIFAF-UHFFFAOYSA-N 0.000 claims description 3
- JTOKVVSQNLAMLI-OAQYLSRUSA-N n-[(4r)-8-chlorospiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]-2-naphthalen-1-ylacetamide Chemical compound C([C@H](C=1C=CC=C(C=1O1)Cl)NC(=O)CC=2C3=CC=CC=C3C=CC=2)C21CCC2 JTOKVVSQNLAMLI-OAQYLSRUSA-N 0.000 claims description 3
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| IN2481/MUM/2007 | 2007-12-18 | ||
| IN2481MU2007 | 2007-12-18 | ||
| IN647MU2008 | 2008-03-26 | ||
| IN647/MUM/2008 | 2008-03-26 | ||
| PCT/IN2008/000838 WO2009084034A2 (en) | 2007-12-18 | 2008-12-16 | Chromane derivatives as trpv3 modulators |
Publications (2)
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| JP2011519343A JP2011519343A (ja) | 2011-07-07 |
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| US8344010B2 (en) | 2008-12-26 | 2013-01-01 | Glenmark Pharmaceuticals S.A. | Fused imidazole derivatives as TRPV3 antagonist |
| WO2010124200A2 (en) | 2009-04-23 | 2010-10-28 | Transposagen Biopharmaceuticals, Inc. | Genetically modified rat models for cancer |
| WO2011002988A1 (en) | 2009-07-01 | 2011-01-06 | Transposagen Biopharmaceuticals, Inc. | Genetically modified rat models for severe combined immunodeficiency (scid) |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| ES2692546T3 (es) | 2011-12-16 | 2018-12-04 | Poseida Therapeutics, Inc. | Moduladores TRPC4 para usar en el tratamiento o la prevención del dolor |
| BR112017009194A2 (pt) * | 2014-10-31 | 2017-12-26 | Abbvie Sarl | tetra-hidropiranos substituídos e método de uso |
| EP3558298A4 (en) * | 2016-12-20 | 2020-08-05 | Merck Sharp & Dohme Corp. | ANTIDIABETIC SPIROCHROMAN COMPOUNDS |
| RU2713946C1 (ru) * | 2019-11-13 | 2020-02-11 | Федеральное государственное бюджетное учреждение науки Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) | 4,7-диметил-3,4,4a,5,8,8a-гексагидроспиро[хромен-2,1'-циклогексан]-4,8-диол в качестве анальгезирующего средства |
| WO2024140431A1 (en) * | 2022-12-26 | 2024-07-04 | Iongen Therapeutics Co., Ltd. | Compounds comprising heteroaryl rings and compositions and methods thereof |
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| AU553266B2 (en) * | 1982-02-04 | 1986-07-10 | Farmitalia Carlo Erba S.P.A. | Substituted 1,3,4-thiadiazolo(3,2-a) pyrimidines |
| US5021432A (en) * | 1988-04-26 | 1991-06-04 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzopyran compound and its pharmaceutical use |
| US5418245A (en) * | 1990-04-16 | 1995-05-23 | Rhone-Poulenc Rorer International (Holdings) Inc. | Styryl-substituted monocyclic and bicyclic heteroaryl compounds which inhibit EGF receptor tyrosine kinase |
| US5276168A (en) * | 1990-06-18 | 1994-01-04 | E. R. Squibb & Sons, Inc. | Benzopyran derivatives and heterocyclic analogs thereof as antiischemic agents |
| JPH07242666A (ja) | 1994-03-08 | 1995-09-19 | Fujisawa Pharmaceut Co Ltd | 複素環化合物 |
| AU6959898A (en) * | 1997-04-11 | 1998-11-11 | David J. Grainger | Compounds and therapies for the prevention of vascular and non-vascular pathol ogies |
| US6797819B1 (en) * | 1998-06-11 | 2004-09-28 | President And Fellows Of Harvard College | Alkaloids |
| AU4997199A (en) * | 1998-07-16 | 2000-02-07 | Axys Pharmaceuticals, Inc. | Process for the synthesis of benzopyran derivatives |
| US6610749B2 (en) * | 2000-02-18 | 2003-08-26 | Arch Development Corporation | Polyhydroxylated benzene-containing compounds |
| US6559145B2 (en) | 2000-07-12 | 2003-05-06 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
| US20040009537A1 (en) * | 2002-01-11 | 2004-01-15 | Jack Roos | Methods of modulating and of identifying agents that modulate intracellular calcium |
| WO2003059346A1 (en) * | 2002-01-18 | 2003-07-24 | The Genetics Company Inc. | Beta-secretase inhibitors |
| JP2006522835A (ja) * | 2003-04-10 | 2006-10-05 | アムジェン インコーポレイテッド | 環状アミン誘導体およびブラジキニンによって媒介される炎症関連障害の処置におけるそれらの使用 |
| JP5010917B2 (ja) * | 2003-08-29 | 2012-08-29 | エグゼリクシス， インコーポレイテッド | ｃ−Ｋｉｔ調節因子および使用方法 |
| GB0325956D0 (en) * | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| WO2006057323A1 (ja) * | 2004-11-26 | 2006-06-01 | Nagasaki University | アミロイド関連疾患診断用組成物 |
| US7576094B2 (en) * | 2004-12-13 | 2009-08-18 | Eli Lilly And Company | Spiro derivatives as lipoxygenase inhibitors |
| CA2624307C (en) | 2005-10-07 | 2014-04-29 | Glenmark Pharmaceuticals S.A. | Substituted benzofused derivatives and their use as vanilloid receptor ligands |
| US20100152209A1 (en) * | 2005-11-04 | 2010-06-17 | Hydra Biosciences Inc. | Compounds for Modulating TRPV3 Function |
| US7872009B2 (en) * | 2005-11-21 | 2011-01-18 | Amgen Inc. | Beta-Secretase modulators and methods of use |
| DE102006012548A1 (de) * | 2006-03-18 | 2007-09-20 | Bayer Healthcare Ag | Substituierte Chromanol-Derivate und ihre Verwendung |
| US20100101733A1 (en) * | 2008-10-24 | 2010-04-29 | Hsiu-Man Yu Chen | Desktop double-sided adhesive tape dispenser |
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2008
- 2008-12-16 US US12/808,937 patent/US8487121B2/en not_active Expired - Fee Related
- 2008-12-16 EP EP08868132A patent/EP2254879A4/en not_active Withdrawn
- 2008-12-16 JP JP2010539048A patent/JP2011519343A/ja active Pending
- 2008-12-16 EA EA201000675A patent/EA201000675A1/ru unknown
- 2008-12-16 NZ NZ595776A patent/NZ595776A/xx not_active IP Right Cessation
- 2008-12-16 WO PCT/IN2008/000838 patent/WO2009084034A2/en not_active Ceased
- 2008-12-16 AU AU2008344922A patent/AU2008344922A1/en not_active Abandoned
- 2008-12-16 GE GEAP200811876A patent/GEP20125707B/en unknown
- 2008-12-16 CA CA2706566A patent/CA2706566A1/en not_active Abandoned
- 2008-12-16 MX MX2010005704A patent/MX2010005704A/es active IP Right Grant
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