BRPI0617674A2

BRPI0617674A2 - composições farmacêuticas e seus usos

composições farmacêuticas e seus usos Download PDF

Info

Publication number: BRPI0617674A2
Authority: BR; Brazil
Prior art keywords: compound; hydroxy; azabicyclo; hexyl; phenyl
Prior art date: 2005-10-19

Application number

BRPI0617674-7A

Other languages

English (en)

Portuguese (pt)

Inventor

Abhijit Ray

Sunanda G Dastidar

Rajkumar Shirumalla

Shivani Malhotra

Original Assignee

Ranbaxy Lab Ltd

Priority date

2005-10-19

Filing date

2006-10-19

Publication date

2011-08-02

2006-10-19 Application filed by Ranbaxy Lab Ltd filed Critical Ranbaxy Lab Ltd

2011-08-02 Publication of BRPI0617674A2 publication Critical patent/BRPI0617674A2/pt

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 23
229940121948 Muscarinic receptor antagonist Drugs 0.000 claims abstract description 33
239000003246 corticosteroid Substances 0.000 claims abstract description 25
229960001334 corticosteroids Drugs 0.000 claims abstract description 24
239000000203 mixture Substances 0.000 claims abstract description 24
239000004480 active ingredient Substances 0.000 claims abstract description 14
230000002757 inflammatory effect Effects 0.000 claims abstract description 10
208000026935 allergic disease Diseases 0.000 claims abstract description 9
230000001363 autoimmune Effects 0.000 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 9
208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
239000003112 inhibitor Substances 0.000 claims abstract description 8
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 7
239000000556 agonist Substances 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 5
230000002265 prevention Effects 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 740
-1 cyano, hydroxy Chemical group 0.000 claims description 212
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 156
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 86
150000003839 salts Chemical class 0.000 claims description 44
125000000217 alkyl group Chemical group 0.000 claims description 40
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 32
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 28
150000002367 halogens Chemical class 0.000 claims description 28
239000001301 oxygen Substances 0.000 claims description 28
229910052760 oxygen Inorganic materials 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 27
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
239000011593 sulfur Chemical group 0.000 claims description 20
229910052717 sulfur Inorganic materials 0.000 claims description 20
102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 19
108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims description 19
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 18
125000001072 heteroaryl group Chemical group 0.000 claims description 18
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 15
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 14
229940124748 beta 2 agonist Drugs 0.000 claims description 14
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
239000005557 antagonist Substances 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 13
150000002148 esters Chemical class 0.000 claims description 13
239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims description 13
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 13
150000001204 N-oxides Chemical class 0.000 claims description 12
125000005842 heteroatom Chemical group 0.000 claims description 12
229940043355 kinase inhibitor Drugs 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
239000003757 phosphotransferase inhibitor Substances 0.000 claims description 12
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
239000002207 metabolite Substances 0.000 claims description 11
229910052757 nitrogen Chemical group 0.000 claims description 11
229940095064 tartrate Drugs 0.000 claims description 11
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 10
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
239000000812 cholinergic antagonist Substances 0.000 claims description 10
125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 10
LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 9
125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 9
229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims description 9
239000012453 solvate Substances 0.000 claims description 9
DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
239000000043 antiallergic agent Substances 0.000 claims description 8
125000005018 aryl alkenyl group Chemical group 0.000 claims description 8
125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
229940052760 dopamine agonists Drugs 0.000 claims description 8
239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
229940002612 prodrug Drugs 0.000 claims description 8
239000000651 prodrug Substances 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 7
102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 7
108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 7
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 7
YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 7
229940049953 phenylacetate Drugs 0.000 claims description 7
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
101150030891 MRAS gene Proteins 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
230000003266 anti-allergic effect Effects 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
239000011630 iodine Substances 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical class OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
LZDOONSYVRDDFD-UHFFFAOYSA-N cyclopentyl 2-phenylacetate Chemical compound C1CCCC1OC(=O)CC1=CC=CC=C1 LZDOONSYVRDDFD-UHFFFAOYSA-N 0.000 claims description 3
ALMHSXDYCFOZQD-UHFFFAOYSA-N n-(3-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C)=C1 ALMHSXDYCFOZQD-UHFFFAOYSA-N 0.000 claims description 3
239000013312 porous aromatic framework Substances 0.000 claims description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 2
MGKPFALCNDRSQD-UHFFFAOYSA-N 2-(4-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C=C1 MGKPFALCNDRSQD-UHFFFAOYSA-N 0.000 claims description 2
RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 2
125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 2
101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 claims description 2
101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
150000003892 tartrate salts Chemical class 0.000 claims 2
QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 claims 1
239000002361 compost Substances 0.000 claims 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
JGIBQAXKXCTKNG-UHFFFAOYSA-N n,n-bis(4-fluorophenyl)acetamide Chemical compound C=1C=C(F)C=CC=1N(C(=O)C)C1=CC=C(F)C=C1 JGIBQAXKXCTKNG-UHFFFAOYSA-N 0.000 claims 1
229930195734 saturated hydrocarbon Natural products 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 abstract description 17
239000003085 diluting agent Substances 0.000 abstract description 16
239000003981 vehicle Substances 0.000 abstract description 16
102000043136 MAP kinase family Human genes 0.000 abstract 1
108091054455 MAP kinase family Proteins 0.000 abstract 1
239000012826 P38 inhibitor Substances 0.000 abstract 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 25
239000002953 phosphate buffered saline Substances 0.000 description 25
239000002253 acid Substances 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 17
125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 16
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 15
210000001519 tissue Anatomy 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
238000000034 method Methods 0.000 description 14
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 13
239000003937 drug carrier Substances 0.000 description 13
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 description 12
229960004373 acetylcholine Drugs 0.000 description 12
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 12
FIMXSEMBHGTNKT-RZVDLVGDSA-N scopine Chemical compound C([C@@H]1N2C)[C@H](O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-RZVDLVGDSA-N 0.000 description 12
230000004044 response Effects 0.000 description 11
230000005764 inhibitory process Effects 0.000 description 10
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 9
241001465754 Metazoa Species 0.000 description 8
108010058846 Ovalbumin Proteins 0.000 description 8
239000002552 dosage form Substances 0.000 description 8
229940092253 ovalbumin Drugs 0.000 description 8
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
241000700159 Rattus Species 0.000 description 7
229910000147 aluminium phosphate Inorganic materials 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
229940079593 drug Drugs 0.000 description 7
239000002158 endotoxin Substances 0.000 description 7
229920006008 lipopolysaccharide Polymers 0.000 description 7
238000012360 testing method Methods 0.000 description 7
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 6
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 6
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 6
229960004484 carbachol Drugs 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000001530 fumaric acid Substances 0.000 description 6
239000004310 lactic acid Substances 0.000 description 6
235000014655 lactic acid Nutrition 0.000 description 6
210000000265 leukocyte Anatomy 0.000 description 6
102000005962 receptors Human genes 0.000 description 6
108020003175 receptors Proteins 0.000 description 6
MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 description 6
229960002586 roflumilast Drugs 0.000 description 6
239000011975 tartaric acid Substances 0.000 description 6
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206010002091 Anaesthesia Diseases 0.000 description 5
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
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210000003979 eosinophil Anatomy 0.000 description 5
229960002714 fluticasone Drugs 0.000 description 5
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 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
230000000241 respiratory effect Effects 0.000 description 5
210000003437 trachea Anatomy 0.000 description 5
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 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 description 4
241000700198 Cavia Species 0.000 description 4
239000012981 Hank's balanced salt solution Substances 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 4
229960004436 budesonide Drugs 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
201000010099 disease Diseases 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
229960001867 guaiacol Drugs 0.000 description 4
125000004446 heteroarylalkyl group Chemical group 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
229960001664 mometasone Drugs 0.000 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 description 4
230000003551 muscarinic effect Effects 0.000 description 4
DPHDSIQHVGSITN-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-2-[1-[(4-fluorophenyl)methyl]-5-hydroxyindol-3-yl]-2-oxoacetamide Chemical compound C1=C(C(=O)C(=O)NC=2C(=CN=CC=2Cl)Cl)C2=CC(O)=CC=C2N1CC1=CC=C(F)C=C1 DPHDSIQHVGSITN-UHFFFAOYSA-N 0.000 description 4
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