CA2807097A1 - Inhibiteurs de metalloproteinase de matrice - Google Patents

Inhibiteurs de metalloproteinase de matrice Download PDF

Info

Publication number: CA2807097A1
Authority: CA; Canada
Prior art keywords: compound; oxo; phenyl; hydroxy; methyl
Prior art date: 2010-07-30
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.): Abandoned

Application number

CA2807097A

Other languages

English (en)

Inventor

Manoj Kumar Khera

Jitendra Sattigeri

Viswajanani Sattigeri

Neeraj Kumar Yadav

Kewal Kumar

Abdul Rehman Abdul Rauf

Ian A. Cliffe

Pradip Kumar Bhatnagar

Abhijit Ray

Punit Srivastava

Sunanda Ghosh Dastidar

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ranbaxy Laboratories Ltd

Original Assignee

Ranbaxy Laboratories Ltd

Priority date (The priority date 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 date listed.)

2010-07-30

Filing date

2011-07-14

Publication date

2012-02-02

2011-07-14 Application filed by Ranbaxy Laboratories Ltd filed Critical Ranbaxy Laboratories Ltd

2012-02-02 Publication of CA2807097A1 publication Critical patent/CA2807097A1/fr

Status Abandoned legal-status Critical Current

Links

239000003771 matrix metalloproteinase inhibitor Substances 0.000 title description 5
229940121386 matrix metalloproteinase inhibitor Drugs 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 416
208000027866 inflammatory disease Diseases 0.000 claims abstract description 13
208000006673 asthma Diseases 0.000 claims abstract description 11
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 9
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims abstract description 8
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims abstract description 8
201000000028 adult respiratory distress syndrome Diseases 0.000 claims abstract description 8
206010028980 Neoplasm Diseases 0.000 claims abstract description 6
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 6
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 5
206010027476 Metastases Diseases 0.000 claims abstract description 5
206010035664 Pneumonia Diseases 0.000 claims abstract description 5
201000004681 Psoriasis Diseases 0.000 claims abstract description 5
201000001263 Psoriatic Arthritis Diseases 0.000 claims abstract description 5
208000036824 Psoriatic arthropathy Diseases 0.000 claims abstract description 5
208000006011 Stroke Diseases 0.000 claims abstract description 5
230000009401 metastasis Effects 0.000 claims abstract description 5
201000006417 multiple sclerosis Diseases 0.000 claims abstract description 5
201000008482 osteoarthritis Diseases 0.000 claims abstract description 5
208000037803 restenosis Diseases 0.000 claims abstract description 5
206010039083 rhinitis Diseases 0.000 claims abstract description 5
208000003556 Dry Eye Syndromes Diseases 0.000 claims abstract description 4
206010013774 Dry eye Diseases 0.000 claims abstract description 4
206010019280 Heart failures Diseases 0.000 claims abstract description 4
208000007565 gingivitis Diseases 0.000 claims abstract description 4
230000000302 ischemic effect Effects 0.000 claims abstract description 4
208000017169 kidney disease Diseases 0.000 claims abstract description 4
230000035755 proliferation Effects 0.000 claims abstract description 4
208000005069 pulmonary fibrosis Diseases 0.000 claims abstract description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 140
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 114
-1 2,4,5-trifluoro-3-methoxyphenyl Chemical group 0.000 claims description 94
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 51
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
239000002253 acid Substances 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 33
125000000623 heterocyclic group Chemical group 0.000 claims description 29
125000001072 heteroaryl group Chemical group 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 26
239000003112 inhibitor Substances 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 19
125000003342 alkenyl group Chemical group 0.000 claims description 16
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 14
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical group 0.000 claims description 11
239000012453 solvate Substances 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
239000000556 agonist Substances 0.000 claims description 8
150000001356 alkyl thiols Chemical class 0.000 claims description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000002877 alkyl aryl group Chemical group 0.000 claims description 7
125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
208000026935 allergic disease Diseases 0.000 claims description 7
125000004367 cycloalkylaryl group Chemical group 0.000 claims description 7
150000002431 hydrogen Chemical group 0.000 claims description 7
230000003301 hydrolyzing effect Effects 0.000 claims description 7
230000002757 inflammatory effect Effects 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
150000003573 thiols Chemical class 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
239000003246 corticosteroid Substances 0.000 claims description 6
229960001334 corticosteroids Drugs 0.000 claims description 6
230000008878 coupling Effects 0.000 claims description 6
238000010168 coupling process Methods 0.000 claims description 6
238000005859 coupling reaction Methods 0.000 claims description 6
229940124761 MMP inhibitor Drugs 0.000 claims description 5
239000005557 antagonist Substances 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 4
239000004072 C09CA03 - Valsartan Substances 0.000 claims description 4
LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 claims description 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 description 4
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 4
238000006668 aldol addition reaction Methods 0.000 claims description 4
NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 claims description 4
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 4
229960004436 budesonide Drugs 0.000 claims description 4
229960003728 ciclesonide Drugs 0.000 claims description 4
229960003957 dexamethasone Drugs 0.000 claims description 4
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000001207 fluorophenyl group Chemical group 0.000 claims description 4
229960002714 fluticasone Drugs 0.000 claims description 4
MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims description 4
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 4
229960001664 mometasone Drugs 0.000 claims description 4
QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 claims description 4
229960002052 salbutamol Drugs 0.000 claims description 4
RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 claims description 4
229960005294 triamcinolone Drugs 0.000 claims description 4
GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims description 4
229960004699 valsartan Drugs 0.000 claims description 4
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
239000002260 anti-inflammatory agent Substances 0.000 claims description 3
239000002220 antihypertensive agent Substances 0.000 claims description 3
229940030600 antihypertensive agent Drugs 0.000 claims description 3
229960005475 antiinfective agent Drugs 0.000 claims description 3
239000004599 antimicrobial Substances 0.000 claims description 3
229940125388 beta agonist Drugs 0.000 claims description 3
125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims description 3
125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 3
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 3
229960000676 flunisolide Drugs 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
239000003018 immunosuppressive agent Substances 0.000 claims description 3
229940125721 immunosuppressive agent Drugs 0.000 claims description 3
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 3
238000011321 prophylaxis Methods 0.000 claims description 3
MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 2
BDEMEPFDHBEHKV-SIKLNZKXSA-N (2s)-2-[(s)-[4-[(2-fluorobenzoyl)amino]phenyl]-hydroxymethyl]-4-(4-oxo-1,2,3-benzotriazin-3-yl)butanoic acid Chemical compound C1=CC([C@H]([C@H](CCN2C(C3=CC=CC=C3N=N2)=O)C(O)=O)O)=CC=C1NC(=O)C1=CC=CC=C1F BDEMEPFDHBEHKV-SIKLNZKXSA-N 0.000 claims description 2
KQZSMOGWYFPKCH-UJPCIWJBSA-N (8s,9s,10r,11s,13s,14s,17r)-17-acetyl-11,17-dihydroxy-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)C[C@@H]2O KQZSMOGWYFPKCH-UJPCIWJBSA-N 0.000 claims description 2
NDAUXUAQIAJITI-LBPRGKRZSA-N (R)-salbutamol Chemical compound CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-LBPRGKRZSA-N 0.000 claims description 2
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
YREYLAVBNPACJM-UHFFFAOYSA-N 2-(tert-butylamino)-1-(2-chlorophenyl)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC=CC=C1Cl YREYLAVBNPACJM-UHFFFAOYSA-N 0.000 claims description 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 claims description 2
IHOXNOQMRZISPV-YJYMSZOUSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]azaniumyl]ethyl]-2-oxo-1h-quinolin-8-olate Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 IHOXNOQMRZISPV-YJYMSZOUSA-N 0.000 claims description 2
239000005541 ACE inhibitor Substances 0.000 claims description 2
ZMYGOSBRLPSJNB-SOMXGXJRSA-N Amelometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O ZMYGOSBRLPSJNB-SOMXGXJRSA-N 0.000 claims description 2
102100024167 C-C chemokine receptor type 3 Human genes 0.000 claims description 2
101710149862 C-C chemokine receptor type 3 Proteins 0.000 claims description 2
239000002126 C01EB10 - Adenosine Substances 0.000 claims description 2
239000002083 C09CA01 - Losartan Substances 0.000 claims description 2
239000002080 C09CA02 - Eprosartan Substances 0.000 claims description 2
239000002947 C09CA04 - Irbesartan Substances 0.000 claims description 2
239000002053 C09CA06 - Candesartan Substances 0.000 claims description 2
239000005537 C09CA07 - Telmisartan Substances 0.000 claims description 2
108010059108 CD18 Antigens Proteins 0.000 claims description 2
229940127291 Calcium channel antagonist Drugs 0.000 claims description 2
102000005600 Cathepsins Human genes 0.000 claims description 2
108010084457 Cathepsins Proteins 0.000 claims description 2
108010036949 Cyclosporine Proteins 0.000 claims description 2
VOVIALXJUBGFJZ-VXKMTNQYSA-N Dexbudesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3O[C@@H](CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-VXKMTNQYSA-N 0.000 claims description 2
WYQPLTPSGFELIB-JTQPXKBDSA-N Difluprednate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2CC[C@@](C(=O)COC(C)=O)(OC(=O)CCC)[C@@]2(C)C[C@@H]1O WYQPLTPSGFELIB-JTQPXKBDSA-N 0.000 claims description 2
108010061435 Enalapril Proteins 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
102000000589 Interleukin-1 Human genes 0.000 claims description 2
108010002352 Interleukin-1 Proteins 0.000 claims description 2
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 2
239000000867 Lipoxygenase Inhibitor Substances 0.000 claims description 2
108010007859 Lisinopril Proteins 0.000 claims description 2
FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 claims description 2
102100029438 Nitric oxide synthase, inducible Human genes 0.000 claims description 2
101710089543 Nitric oxide synthase, inducible Proteins 0.000 claims description 2
229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 2
VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 claims description 2
108700023400 Platelet-activating factor receptors Proteins 0.000 claims description 2
BPZSYCZIITTYBL-YJYMSZOUSA-N R-Formoterol Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-YJYMSZOUSA-N 0.000 claims description 2
101100545004 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YSP2 gene Proteins 0.000 claims description 2
GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims description 2
102000001400 Tryptase Human genes 0.000 claims description 2
108060005989 Tryptase Proteins 0.000 claims description 2
MVLBCBPGBUAVJQ-CENSZEJFSA-N [(6s,8s,9r,10s,11s,13s,14s,16r,17r)-17-(chloromethylsulfanylcarbonyl)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCCl)(OC(=O)CC)[C@@]2(C)C[C@@H]1O MVLBCBPGBUAVJQ-CENSZEJFSA-N 0.000 claims description 2
UYVYDRXVNVNQEA-BJTOFBPUSA-N [2-[(8s,9r,10s,11s,13s,14s,16s,17r)-9-chloro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 4-(acetamidomethyl)cyclohexane-1-carboxylate Chemical compound O=C([C@]1(O)[C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@@H]1C)COC(=O)C1CCC(CNC(C)=O)CC1 UYVYDRXVNVNQEA-BJTOFBPUSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
229960005305 adenosine Drugs 0.000 claims description 2
229960000552 alclometasone Drugs 0.000 claims description 2
FJXOGVLKCZQRDN-PHCHRAKRSA-N alclometasone Chemical compound C([C@H]1Cl)C2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O FJXOGVLKCZQRDN-PHCHRAKRSA-N 0.000 claims description 2
229960003099 amcinonide Drugs 0.000 claims description 2
ILKJAFIWWBXGDU-MOGDOJJUSA-N amcinonide Chemical compound O([C@@]1([C@H](O2)C[C@@H]3[C@@]1(C[C@H](O)[C@]1(F)[C@@]4(C)C=CC(=O)C=C4CC[C@H]13)C)C(=O)COC(=O)C)C12CCCC1 ILKJAFIWWBXGDU-MOGDOJJUSA-N 0.000 claims description 2
229950008046 amelometasone Drugs 0.000 claims description 2
229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 2
239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 2
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230000003110 anti-inflammatory effect Effects 0.000 claims description 2
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229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000000926 separation method Methods 0.000 description 1
201000001223 septic arthritis Diseases 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
231100000019 skin ulcer Toxicity 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
229960001945 sparteine Drugs 0.000 description 1
SLRCCWJSBJZJBV-AJNGGQMLSA-N sparteine Chemical compound C1N2CCCC[C@H]2[C@@H]2CN3CCCC[C@H]3[C@H]1C2 SLRCCWJSBJZJBV-AJNGGQMLSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
108091007196 stromelysin Proteins 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
230000008093 supporting effect Effects 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
201000004595 synovitis Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
230000008685 targeting Effects 0.000 description 1
201000004415 tendinitis Diseases 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000005309 thioalkoxy group Chemical group 0.000 description 1
230000007838 tissue remodeling Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000008733 trauma Effects 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
150000008648 triflates Chemical class 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
230000005747 tumor angiogenesis Effects 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000009736 wetting Methods 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Rheumatology (AREA)
Urology & Nephrology (AREA)
Oncology (AREA)
Vascular Medicine (AREA)
Dermatology (AREA)
Communicable Diseases (AREA)
Pain & Pain Management (AREA)
Transplantation (AREA)
Ophthalmology & Optometry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Hospice & Palliative Care (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Otolaryngology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA2807097A 2010-07-30 2011-07-14 Inhibiteurs de metalloproteinase de matrice Abandoned CA2807097A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IN1810DE2010		2010-07-30
IN1810/DEL/2010		2010-07-30
PCT/IB2011/053155 WO2012014114A1 (fr)	2010-07-30	2011-07-14	Inhibiteurs de métalloprotéinase de matrice

Publications (1)

Publication Number	Publication Date
CA2807097A1 true CA2807097A1 (fr)	2012-02-02

Family

ID=44720049

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2807097A Abandoned CA2807097A1 (fr)	2010-07-30	2011-07-14	Inhibiteurs de metalloproteinase de matrice

Country Status (12)

Country	Link
EP (1)	EP2598493A1 (fr)
JP (1)	JP2013537533A (fr)
KR (1)	KR20130042590A (fr)
CN (1)	CN103119030A (fr)
AU (1)	AU2011284397A1 (fr)
BR (1)	BR112013002370A2 (fr)
CA (1)	CA2807097A1 (fr)
CO (1)	CO6680674A2 (fr)
MX (1)	MX2013001240A (fr)
PH (1)	PH12013500198A1 (fr)
SG (1)	SG187654A1 (fr)
WO (1)	WO2012014114A1 (fr)

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AU2013256064B2 (en)	2012-05-03	2018-01-04	Alcon Inc.	Pharmaceutical nanoparticles showing improved mucosal transport
US11596599B2 (en)	2012-05-03	2023-03-07	The Johns Hopkins University	Compositions and methods for ophthalmic and/or other applications
KR102310775B1 (ko)	2012-05-03	2021-10-07	칼라 파마슈티컬스, 인크.	개선된 점막 수송을 나타내는 제약 나노입자
JP6669499B2 (ja)	2013-02-15	2020-03-18	カラファーマシューティカルズインコーポレイテッド	治療用化合物
JP2016510000A (ja)	2013-02-20	2016-04-04	カラファーマシューティカルズインコーポレイテッド	治療用化合物およびその使用
US9688688B2 (en)	2013-02-20	2017-06-27	Kala Pharmaceuticals, Inc.	Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof
CN103304634B (zh) *	2013-05-30	2015-04-29	温州芳植生物科技有限公司	基质金属蛋白酶-2多肽抑制剂及其应用
CN103254290B (zh) *	2013-05-30	2014-09-03	南通广泰生化制品有限公司	基质金属蛋白酶-2多肽抑制剂及其应用
NZ719185A (en)	2013-11-01	2017-11-24	Kala Pharmaceuticals Inc	Crystalline forms of therapeutic compounds and uses thereof
US9890173B2 (en)	2013-11-01	2018-02-13	Kala Pharmaceuticals, Inc.	Crystalline forms of therapeutic compounds and uses thereof
WO2015150366A1 (fr) *	2014-04-03	2015-10-08	Bayer Pharma Aktiengesellschaft	Dérivés d'éthers phénoliques à substitutions cycliques et leur utilisation
US20170119776A1 (en)	2014-04-03	2017-05-04	Bayer Pharma Aktiengesellschaft	Chiral 2,5-disubstituted cyclopentanecarboxylic acid derivatives and use thereof
US20170114049A1 (en)	2014-04-03	2017-04-27	Bayer Pharma Aktiengesellschaft	2,5-disubstituted cyclopentane carboxylic acids for the treatment of respiratory tract diseases
WO2015150364A1 (fr) *	2014-04-03	2015-10-08	Bayer Pharma Aktiengesellschaft	Acides benzotriazinonebutyriques substitués et leur utilisation
EP3126339A1 (fr)	2014-04-03	2017-02-08	Bayer Pharma Aktiengesellschaft	Acides cyclopentanecarboxyliques à disubstitution 2,5 et leur utilisation
WO2015189117A1 (fr) *	2014-06-12	2015-12-17	Bayer Pharma Aktiengesellschaft	Dérivés de l'acide 4-oxobutanoïque hétérobicycliques substitués et utilisation desdits dérivés
JOP20190024A1 (ar)	2016-08-26	2019-02-19	Gilead Sciences Inc	مركبات بيروليزين بها استبدال واستخداماتها
AU2017324713B2 (en)	2016-09-08	2020-08-13	KALA BIO, Inc.	Crystalline forms of therapeutic compounds and uses thereof
KR20190051010A (ko)	2016-09-08	2019-05-14	칼라 파마슈티컬스, 인크.	치료 화합물의 결정형 및 그의 용도
EP3509423A4 (fr)	2016-09-08	2020-05-13	Kala Pharmaceuticals, Inc.	Formes cristallines de composés thérapeutiques et leurs utilisations
PL3759109T3 (pl)	2018-02-26	2024-03-04	Gilead Sciences, Inc.	Podstawione związki pirolizyny jako inhibitory replikacji hbv
CN121001714A (zh) *	2023-09-12	2025-11-21	株式会社Lg化学	具有抗炎活性的化妆品组合物

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2011
- 2011-07-14 SG SG2013007448A patent/SG187654A1/en unknown
- 2011-07-14 KR KR1020137005055A patent/KR20130042590A/ko not_active Withdrawn
- 2011-07-14 WO PCT/IB2011/053155 patent/WO2012014114A1/fr not_active Ceased
- 2011-07-14 EP EP11763767.8A patent/EP2598493A1/fr not_active Withdrawn
- 2011-07-14 MX MX2013001240A patent/MX2013001240A/es not_active Application Discontinuation
- 2011-07-14 BR BR112013002370A patent/BR112013002370A2/pt not_active IP Right Cessation
- 2011-07-14 PH PH1/2013/500198A patent/PH12013500198A1/en unknown
- 2011-07-14 CN CN2011800461515A patent/CN103119030A/zh active Pending
- 2011-07-14 AU AU2011284397A patent/AU2011284397A1/en not_active Abandoned
- 2011-07-14 JP JP2013522322A patent/JP2013537533A/ja not_active Withdrawn
- 2011-07-14 CA CA2807097A patent/CA2807097A1/fr not_active Abandoned
2013
- 2013-02-28 CO CO13040146A patent/CO6680674A2/es not_active Application Discontinuation

Also Published As

Publication number	Publication date
CN103119030A (zh)	2013-05-22
EP2598493A1 (fr)	2013-06-05
JP2013537533A (ja)	2013-10-03
CO6680674A2 (es)	2013-05-31
WO2012014114A1 (fr)	2012-02-02
SG187654A1 (en)	2013-03-28
BR112013002370A2 (pt)	2017-06-20
PH12013500198A1 (en)	2013-03-11
KR20130042590A (ko)	2013-04-26
AU2011284397A1 (en)	2013-02-21
MX2013001240A (es)	2013-08-27

Legal Events

Date	Code	Title	Description
2013-03-08	EEER	Examination request	Effective date: 20130130
2014-09-09	FZDE	Discontinued	Effective date: 20140715

Publication	Publication Date	Title
CA2807097A1 (fr)	2012-02-02	Inhibiteurs de metalloproteinase de matrice
CA2812319A1 (fr)	2012-03-29	Inhibiteurs de metalloproteinase matricielle
JP6002785B2 (ja)	2016-10-05	ナトリウムチャネルモジュレーターとしてのベンゾイミダゾールおよびイミダゾピリジン誘導体
JP4592077B2 (ja)	2010-12-01	嘔吐、抑鬱、不安および咳の処置のためのニューロキニン−１（ｎｋ−１）アンタゴニストとしての１−アミド−４−フェニル−４−ベンジルオキシメチル−ピペリジン誘導体および関連化合物
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