MX2007007895A - Inhibidores multiciclicos de bis-amida mmp. - Google Patents
Inhibidores multiciclicos de bis-amida mmp.Info
- Publication number
- MX2007007895A MX2007007895A MX2007007895A MX2007007895A MX2007007895A MX 2007007895 A MX2007007895 A MX 2007007895A MX 2007007895 A MX2007007895 A MX 2007007895A MX 2007007895 A MX2007007895 A MX 2007007895A MX 2007007895 A MX2007007895 A MX 2007007895A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- group
- optionally substituted
- aryl
- cycloalkyl
- Prior art date
Links
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 title abstract description 29
- 229940124761 MMP inhibitor Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 270
- 102100027995 Collagenase 3 Human genes 0.000 claims abstract description 58
- 108050005238 Collagenase 3 Proteins 0.000 claims abstract description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 46
- 239000003112 inhibitor Substances 0.000 claims abstract description 29
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 559
- 229910052739 hydrogen Inorganic materials 0.000 claims description 272
- 239000001257 hydrogen Substances 0.000 claims description 272
- 125000003118 aryl group Chemical group 0.000 claims description 242
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 241
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 196
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 194
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 190
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 190
- 125000001072 heteroaryl group Chemical group 0.000 claims description 182
- 229910052717 sulfur Inorganic materials 0.000 claims description 182
- 125000001188 haloalkyl group Chemical group 0.000 claims description 153
- -1 C (O) NR10Rn Chemical group 0.000 claims description 112
- 125000000304 alkynyl group Chemical group 0.000 claims description 103
- 125000005843 halogen group Chemical group 0.000 claims description 101
- 125000003342 alkenyl group Chemical group 0.000 claims description 93
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 90
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 85
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 77
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 74
- 229910052757 nitrogen Inorganic materials 0.000 claims description 72
- 201000010099 disease Diseases 0.000 claims description 66
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 66
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 60
- 229910052799 carbon Inorganic materials 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 55
- 125000004122 cyclic group Chemical group 0.000 claims description 44
- 125000005842 heteroatom Chemical group 0.000 claims description 44
- 229910052760 oxygen Inorganic materials 0.000 claims description 43
- 125000002619 bicyclic group Chemical group 0.000 claims description 39
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 38
- 239000003814 drug Substances 0.000 claims description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 29
- 229920006395 saturated elastomer Polymers 0.000 claims description 28
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 230000001404 mediated effect Effects 0.000 claims description 24
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 150000001204 N-oxides Chemical class 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
- 229940111134 coxibs Drugs 0.000 claims description 16
- 239000003260 cyclooxygenase 1 inhibitor Substances 0.000 claims description 16
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 14
- 229940079593 drug Drugs 0.000 claims description 14
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 14
- 239000003018 immunosuppressive agent Substances 0.000 claims description 14
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 150000003431 steroids Chemical class 0.000 claims description 14
- 230000001225 therapeutic effect Effects 0.000 claims description 14
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- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 13
- 230000008512 biological response Effects 0.000 claims description 13
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- 239000003607 modifier Substances 0.000 claims description 13
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 13
- 239000002988 disease modifying antirheumatic drug Substances 0.000 claims description 12
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229940123907 Disease modifying antirheumatic drug Drugs 0.000 claims description 11
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 11
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- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 11
- 229960002702 piroxicam Drugs 0.000 claims description 11
- 102000019034 Chemokines Human genes 0.000 claims description 10
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 208000002223 abdominal aortic aneurysm Diseases 0.000 claims description 9
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- 229910052701 rubidium Inorganic materials 0.000 claims description 9
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 8
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 8
- 239000005557 antagonist Substances 0.000 claims description 8
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- 230000006378 damage Effects 0.000 claims description 8
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 8
- 229960000485 methotrexate Drugs 0.000 claims description 8
- 208000011580 syndromic disease Diseases 0.000 claims description 8
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 7
- 206010065390 Inflammatory pain Diseases 0.000 claims description 7
- 229960000590 celecoxib Drugs 0.000 claims description 7
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 7
- 230000002757 inflammatory effect Effects 0.000 claims description 7
- 229960000371 rofecoxib Drugs 0.000 claims description 7
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical group C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 229960002004 valdecoxib Drugs 0.000 claims description 7
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 7
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 6
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 210000001519 tissue Anatomy 0.000 claims description 5
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims description 4
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 4
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims description 4
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 4
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- 208000031229 Cardiomyopathies Diseases 0.000 claims description 4
- 229940122444 Chemokine receptor antagonist Drugs 0.000 claims description 4
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 4
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 4
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 4
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 4
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- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 4
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- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 4
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- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 4
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- HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 claims description 4
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- HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 claims description 4
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/00—Drugs for skeletal disorders
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| PCT/US2005/047421 WO2006083454A1 (en) | 2004-12-31 | 2005-12-31 | Multicyclic bis-amide mmp inhibitors |
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| US20070155738A1 (en) | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| US20070155737A1 (en) * | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| WO2007079199A2 (en) * | 2005-12-30 | 2007-07-12 | Alantos Pharmaceuticals, Holding, Inc. | Substituted bis-amide metalloprotease inhibitors |
| EP2069313A2 (en) * | 2006-06-29 | 2009-06-17 | Alantos Pharmaceuticals Holdings, Inc. | Metalloprotease inhibitors |
| ATE528306T1 (de) * | 2006-11-02 | 2011-10-15 | Piramal Life Sciences Ltd | Benzoxazepin-verbindungen, ihre herstellung und verwendung |
| US20080221092A1 (en) * | 2006-11-20 | 2008-09-11 | Harald Bluhm | Heterobicyclic metalloprotease inhibitors |
| CA2670083A1 (en) * | 2006-11-20 | 2008-05-29 | Alantos Pharmaceuticals Holding, Inc. | Heterobicyclic metalloprotease inhibitors |
| CA2680312A1 (en) * | 2007-03-07 | 2008-09-12 | Alantos Pharmaceuticals Holding, Inc. | Metalloprotease inhibitors containing a heterocyclic moiety |
| WO2008149191A1 (en) * | 2007-06-05 | 2008-12-11 | Pfizer Inc. | Hetero bicyclic carboxamide derivatives and their pharmaceutical use and compositions |
| JP5487214B2 (ja) | 2008-12-19 | 2014-05-07 | ブリストル−マイヤーズ スクイブ カンパニー | キナーゼ阻害剤として有用なカルバゾールカルボキシアミド化合物 |
| US8362048B2 (en) | 2009-11-13 | 2013-01-29 | Receptos, Inc. | Selective sphingosine 1 phosphate receptor modulators and methods of chiral synthesis |
| KR101771755B1 (ko) * | 2009-11-13 | 2017-08-25 | 셀진 인터내셔널 Ii 에스에이알엘 | 선택적 헤테로시클릭 스핑고신 1 포스페이트 수용체 조절자 |
| NZ599913A (en) | 2009-11-13 | 2014-08-29 | Receptos Inc | Sphingosine 1 phosphate receptor modulators and methods of chiral synthesis |
| JP5809157B2 (ja) | 2010-10-08 | 2015-11-10 | 持田製薬株式会社 | 環状アミド誘導体 |
| JP5420796B2 (ja) | 2011-04-27 | 2014-02-19 | 持田製薬株式会社 | 新規3−ヒドロキシイソチアゾール1−オキシド誘導体 |
| CA2834465A1 (en) | 2011-04-28 | 2012-11-01 | Mochida Pharmaceutical Co., Ltd. | Cyclic amide derivative |
| WO2012158550A2 (en) | 2011-05-13 | 2012-11-22 | Receptos, Inc. | Selective heterocyclic sphingosine 1 phosphate receptor modulators |
| JP2014527511A (ja) | 2011-06-24 | 2014-10-16 | アムジエン・インコーポレーテツド | Trpm8拮抗剤及び治療におけるそれらの使用 |
| EP2723718A1 (en) | 2011-06-24 | 2014-04-30 | Amgen Inc. | Trpm8 antagonists and their use in treatments |
| US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
| CN105101979B (zh) | 2012-12-21 | 2021-10-08 | 安斯泰来再生医药协会 | 由多能干细胞制备血小板的方法及其组合物 |
| WO2018083105A1 (en) * | 2016-11-01 | 2018-05-11 | F. Hoffmann-La Roche Ag | Pyridazine derivatives as rorc modulators |
| WO2019100106A1 (en) * | 2017-11-24 | 2019-05-31 | The University Of Sydney | Antibacterial compounds and methods of use thereof |
| SI3740481T1 (sl) | 2018-01-19 | 2024-09-30 | Cytokinetics, Inc. | Analogi dihidrobenzofurana in indena kot zaviralci srčne sarkomere |
| EP3814343B1 (en) | 2018-06-26 | 2023-01-11 | Cytokinetics, Inc. | Cardiac sarcomere inhibitors |
| EP3814342B1 (en) | 2018-06-26 | 2022-07-27 | Cytokinetics, Inc. | Cardiac sarcomere inhibitors |
| AU2019328556B2 (en) | 2018-08-31 | 2025-09-04 | Cytokinetics, Inc. | Cardiac sarcomere inhibitors |
| MX2021012325A (es) * | 2019-04-08 | 2022-05-18 | Pi Industries Ltd | Nuevos compuestos de oxadiazol para controlar o prevenir hongos fitopatogénicos. |
| GB201908453D0 (en) | 2019-06-12 | 2019-07-24 | Enterprise Therapeutics Ltd | Compounds for treating respiratory disease |
| JP2024508526A (ja) | 2021-03-04 | 2024-02-27 | サイトキネティックス, インコーポレイテッド | 心筋サルコメア阻害剤 |
| AR126681A1 (es) | 2021-08-03 | 2023-11-01 | Cytokinetics Inc | Proceso para la preparación de aficamten |
| EP4431491A4 (en) * | 2021-11-08 | 2025-03-05 | Asahi Kasei Kabushiki Kaisha | CARBONYL COMPOUND, METHOD FOR PRODUCING A CARBONYL COMPOUND, METHOD FOR PRODUCING AN ISOCYANATE COMPOUND AND ISOCYANATE COMPOSITION |
| CN118302407A (zh) * | 2021-11-08 | 2024-07-05 | 旭化成株式会社 | 羰基化合物、羰基化合物的制造方法、异氰酸酯化合物的制造方法以及异氰酸酯组合物 |
| CN115778930B (zh) * | 2022-12-08 | 2024-02-27 | 陕西中医药大学 | 一种具有血管舒张活性的二硫缩醛类化合物在制备具有血管舒张活性药物方面的应用 |
| WO2025124698A1 (en) | 2023-12-12 | 2025-06-19 | Idorsia Pharmaceuticals Ltd | Aryl sulfone and sulfanone derivatives as orexin receptor modulators |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1368323B1 (en) * | 2001-02-14 | 2010-06-30 | Warner-Lambert Company LLC | Pyrimidine matrix metalloproteinase inhibitors |
| DE10160357A1 (de) * | 2001-12-08 | 2003-06-18 | Aventis Pharma Gmbh | Verwendung von Pyridin-2,4-dicarbonsäurediamiden und Pyrimidin-4,6-dicarbonsäurediamiden zur selektiven Inhibierung von Kollagenasen |
| ATE388941T1 (de) * | 2002-11-02 | 2008-03-15 | Sanofi Aventis Deutschland | Neue pyrimidin-4,6-dicarbons urediamide zur selektiven inhibierung von kollagenasen |
| DE10300017A1 (de) * | 2003-01-03 | 2004-07-15 | Aventis Pharma Deutschland Gmbh | Selektive MMP 13 Inhibitoren |
-
2005
- 2005-12-30 US US11/324,037 patent/US20060173183A1/en not_active Abandoned
- 2005-12-31 JP JP2007549640A patent/JP2008526761A/ja not_active Abandoned
- 2005-12-31 AU AU2005326659A patent/AU2005326659A1/en not_active Abandoned
- 2005-12-31 WO PCT/US2005/047421 patent/WO2006083454A1/en not_active Ceased
- 2005-12-31 CA CA002589328A patent/CA2589328A1/en not_active Abandoned
- 2005-12-31 EP EP05855910A patent/EP1843820A1/en not_active Withdrawn
- 2005-12-31 MX MX2007007895A patent/MX2007007895A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2589328A1 (en) | 2006-08-10 |
| WO2006083454A1 (en) | 2006-08-10 |
| JP2008526761A (ja) | 2008-07-24 |
| AU2005326659A1 (en) | 2006-08-10 |
| EP1843820A1 (en) | 2007-10-17 |
| US20060173183A1 (en) | 2006-08-03 |
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| FA | Abandonment or withdrawal |