SG187654A1 - Matrix metalloproteinase inhibitors - Google Patents

Info

Publication number

SG187654A1

SG187654A1 SG2013007448A SG2013007448A SG187654A1 SG 187654 A1 SG187654 A1 SG 187654A1 SG 2013007448 A SG2013007448 A SG 2013007448A SG 2013007448 A SG2013007448 A SG 2013007448A SG 187654 A1 SG187654 A1 SG 187654A1

Authority

SG

Singapore

Prior art keywords

compound

phenyl

hydroxy

methyl

butanoic acid

Prior art date

2010-07-30

Links

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• 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 403
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 12
• 208000006673 asthma Diseases 0.000 claims abstract description 11
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 9
• 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
• 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 348
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 222
• -1 1,2,3-benzotriazin-3(4H)-yl Chemical group 0.000 claims description 128
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 117
• 125000000217 alkyl group Chemical group 0.000 claims description 38
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 38
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 26
• 239000003112 inhibitor Substances 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 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
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
• 201000010099 disease Diseases 0.000 claims description 11
• 229910052736 halogen Inorganic materials 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
• 150000002367 halogens Chemical group 0.000 claims description 10
• 239000000556 agonist Substances 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
• 150000001356 alkyl thiols Chemical class 0.000 claims description 8
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
• 150000003573 thiols Chemical class 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
• 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• 230000003301 hydrolyzing effect Effects 0.000 claims description 7
• 230000002757 inflammatory effect Effects 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 239000003246 corticosteroid Substances 0.000 claims description 6
• 229960001334 corticosteroids Drugs 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
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 230000008878 coupling Effects 0.000 claims description 5
• 238000010168 coupling process Methods 0.000 claims description 5
• 238000005859 coupling reaction Methods 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 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
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 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
• 229960000676 flunisolide Drugs 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
• 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 4
• 229960002052 salbutamol Drugs 0.000 claims description 4
• 208000011580 syndromic disease Diseases 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
• 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
• 206010003246 arthritis Diseases 0.000 claims description 3
• 208000010668 atopic eczema Diseases 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
• 125000006639 cyclohexyl 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
• 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
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 3
• 238000011321 prophylaxis Methods 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
• 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
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 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
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 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
• 230000001154 acute effect Effects 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
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 2
• 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
• 229940111136 antiinflammatory and antirheumatic drug fenamates Drugs 0.000 claims description 2
• 229960001692 arformoterol Drugs 0.000 claims description 2
• LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 claims description 2
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