TW200803848A

TW200803848A - Medicament combinations for the treatment of respiratory diseases

Medicament combinations for the treatment of respiratory diseases Download PDF

Info

Publication number: TW200803848A
Authority: TW; Taiwan
Prior art keywords: amino; phenyl; methyl; pharmaceutical combination; methoxy
Prior art date: 2006-02-16

Application number

TW096105758A

Other languages

English (en)

Chinese (zh)

Inventor

Ingo Konetzki

Thierry Bouyssou

Sabine Pestel

Andreas Schnapp

Original Assignee

Boehringer Ingelheim Int

Priority date

2006-02-16

Filing date

2007-02-15

Publication date

2008-01-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=35983924&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=TW200803848(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2007-02-15 Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int

2008-01-16 Publication of TW200803848A publication Critical patent/TW200803848A/zh

Links

239000003814 drug Substances 0.000 title claims abstract description 36
208000023504 respiratory system disease Diseases 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims abstract description 206
239000013543 active substance Substances 0.000 claims abstract description 76
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 31
-1 decyloxy Ethoxy Chemical group 0.000 claims description 206
150000003839 salts Chemical group 0.000 claims description 93
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 84
239000000203 mixture Substances 0.000 claims description 80
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 79
239000002253 acid Substances 0.000 claims description 61
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 47
239000012453 solvate Substances 0.000 claims description 41
239000002904 solvent Substances 0.000 claims description 39
229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 37
239000000812 cholinergic antagonist Substances 0.000 claims description 37
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
229940079593 drug Drugs 0.000 claims description 30
229910052731 fluorine Inorganic materials 0.000 claims description 28
239000011737 fluorine Chemical group 0.000 claims description 28
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 27
150000003431 steroids Chemical class 0.000 claims description 27
239000000546 pharmaceutical excipient Substances 0.000 claims description 26
238000002360 preparation method Methods 0.000 claims description 26
239000003380 propellant Substances 0.000 claims description 24
239000000843 powder Substances 0.000 claims description 23
239000000443 aerosol Substances 0.000 claims description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
239000005557 antagonist Substances 0.000 claims description 17
229940121647 egfr inhibitor Drugs 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 16
239000003112 inhibitor Substances 0.000 claims description 16
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
238000009472 formulation Methods 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
239000000126 substance Substances 0.000 claims description 15
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 13
230000001225 therapeutic effect Effects 0.000 claims description 12
YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 8
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
239000000725 suspension Substances 0.000 claims description 7
239000000052 vinegar Substances 0.000 claims description 7
235000021419 vinegar Nutrition 0.000 claims description 7
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
206010006451 bronchitis Diseases 0.000 claims description 6
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical group F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
201000004624 Dermatitis Diseases 0.000 claims description 4
206010014561 Emphysema Diseases 0.000 claims description 4
206010037423 Pulmonary oedema Diseases 0.000 claims description 4
208000030934 Restrictive pulmonary disease Diseases 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
208000005333 pulmonary edema Diseases 0.000 claims description 4
201000003883 Cystic fibrosis Diseases 0.000 claims description 3
208000011623 Obstructive Lung disease Diseases 0.000 claims description 3
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
230000000747 cardiac effect Effects 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
239000000890 drug combination Substances 0.000 claims description 3
230000002757 inflammatory effect Effects 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
230000000414 obstructive effect Effects 0.000 claims description 3
239000000600 sorbitol Substances 0.000 claims description 3
206010003671 Atrioventricular Block Diseases 0.000 claims description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
208000029523 Interstitial Lung disease Diseases 0.000 claims description 2
201000009267 bronchiectasis Diseases 0.000 claims description 2
239000001273 butane Substances 0.000 claims description 2
230000005796 circulatory shock Effects 0.000 claims description 2
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
150000002016 disaccharides Chemical class 0.000 claims description 2
230000004054 inflammatory process Effects 0.000 claims description 2
210000004072 lung Anatomy 0.000 claims description 2
150000002772 monosaccharides Chemical class 0.000 claims description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
239000001294 propane Substances 0.000 claims description 2
230000033764 rhythmic process Effects 0.000 claims description 2
230000024883 vasodilation Effects 0.000 claims description 2
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
206010049765 Bradyarrhythmia Diseases 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
208000036029 Uterine contractions during pregnancy Diseases 0.000 claims 1
239000003416 antiarrhythmic agent Substances 0.000 claims 1
208000006218 bradycardia Diseases 0.000 claims 1
102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims 1
108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
230000007774 longterm Effects 0.000 claims 1
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 1
229920001542 oligosaccharide Polymers 0.000 claims 1
150000002482 oligosaccharides Chemical class 0.000 claims 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims 1
239000000779 smoke Substances 0.000 claims 1
238000000034 method Methods 0.000 abstract description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 248
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
239000000243 solution Substances 0.000 description 58
238000001819 mass spectrum Methods 0.000 description 55
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
229910052739 hydrogen Inorganic materials 0.000 description 47
239000001257 hydrogen Substances 0.000 description 43
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
238000007792 addition Methods 0.000 description 39
235000019441 ethanol Nutrition 0.000 description 34
239000007789 gas Substances 0.000 description 31
235000019439 ethyl acetate Nutrition 0.000 description 29
239000007787 solid Substances 0.000 description 29
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 28
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 25
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 25
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 24
239000003054 catalyst Substances 0.000 description 24
239000002585 base Substances 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
150000004677 hydrates Chemical class 0.000 description 19
229940102396 methyl bromide Drugs 0.000 description 18
239000012074 organic phase Substances 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
150000001450 anions Chemical class 0.000 description 17
150000001768 cations Chemical class 0.000 description 17
239000003795 chemical substances by application Substances 0.000 description 16
150000002431 hydrogen Chemical class 0.000 description 16
239000003921 oil Substances 0.000 description 16
235000019198 oils Nutrition 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 15
CHRMMMLUWHPZAH-UHFFFAOYSA-N 7-methoxyquinazoline Chemical compound C1=NC=NC2=CC(OC)=CC=C21 CHRMMMLUWHPZAH-UHFFFAOYSA-N 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000011777 magnesium Substances 0.000 description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
150000001412 amines Chemical class 0.000 description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
229910052794 bromium Inorganic materials 0.000 description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
239000000047 product Substances 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 10
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
238000012360 testing method Methods 0.000 description 9
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
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235000011054 acetic acid Nutrition 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 8
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
238000001816 cooling Methods 0.000 description 8
238000005984 hydrogenation reaction Methods 0.000 description 8
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 8
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
241000251468 Actinopterygii Species 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
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238000006243 chemical reaction Methods 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 6
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
208000006673 asthma Diseases 0.000 description 6
125000005605 benzo group Chemical group 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
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201000010099 disease Diseases 0.000 description 6
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
238000002844 melting Methods 0.000 description 6
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VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 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 description 6
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
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CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
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