ZA200604485B - Novel M3 muscarinic acetylcholine receptor antagonists - Google Patents

Novel M3 muscarinic acetylcholine receptor antagonists Download PDF

Info

Publication number: ZA200604485B
Authority: ZA; South Africa
Prior art keywords: lower alkyl; methyl; phenyl; amino; piperidiniumyl
Prior art date: 2003-12-03

Application number

ZA200604485A

Other languages

English (en)

Inventor

Busch-Petersen Jakob

Jin Jian

Fu Wei

Michael R Palovich

Original Assignee

Glaxo Group 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.)

2003-12-03

Filing date

2006-06-01

Publication date

2007-11-28

2006-06-01 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2007-11-28 Publication of ZA200604485B publication Critical patent/ZA200604485B/en

Links

102000014415 Muscarinic acetylcholine receptor Human genes 0.000 title claims description 15
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 title claims description 15
229940121683 Acetylcholine receptor antagonist Drugs 0.000 title description 2
125000000217 alkyl group Chemical group 0.000 claims description 216
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 101
-1 hydroxy, amino Chemical group 0.000 claims description 101
125000000753 cycloalkyl group Chemical group 0.000 claims description 77
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 61
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
150000001875 compounds Chemical class 0.000 claims description 34
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 23
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 22
125000001475 halogen functional group Chemical group 0.000 claims description 22
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 21
125000002541 furyl group Chemical group 0.000 claims description 21
125000001624 naphthyl group Chemical group 0.000 claims description 21
125000004076 pyridyl group Chemical group 0.000 claims description 21
125000001544 thienyl group Chemical group 0.000 claims description 21
125000001041 indolyl group Chemical group 0.000 claims description 20
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
239000001301 oxygen Chemical group 0.000 claims description 15
229910052760 oxygen Chemical group 0.000 claims description 15
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 12
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
125000002883 imidazolyl group Chemical group 0.000 claims description 9
125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 7
230000001404 mediated effect Effects 0.000 claims description 7
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 6
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
150000002500 ions Chemical class 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 4
208000028257 Joubert syndrome with oculorenal defect Diseases 0.000 claims description 4
229960004373 acetylcholine Drugs 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
230000002401 inhibitory effect Effects 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
102000005962 receptors Human genes 0.000 claims description 3
108020003175 receptors Proteins 0.000 claims description 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
PQFMNVGMJJMLAE-QMMMGPOBSA-N L-tyrosinamide Chemical compound NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 PQFMNVGMJJMLAE-QMMMGPOBSA-N 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
229940112141 dry powder inhaler Drugs 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
206010006458 Bronchitis chronic Diseases 0.000 claims 1
101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 claims 1
206010014561 Emphysema Diseases 0.000 claims 1
241000124008 Mammalia Species 0.000 claims 1
206010061876 Obstruction Diseases 0.000 claims 1
206010039085 Rhinitis allergic Diseases 0.000 claims 1
201000010105 allergic rhinitis Diseases 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
206010006451 bronchitis Diseases 0.000 claims 1
208000007451 chronic bronchitis Diseases 0.000 claims 1
230000001684 chronic effect Effects 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229940071648 metered dose inhaler Drugs 0.000 claims 1
208000005069 pulmonary fibrosis Diseases 0.000 claims 1
230000000241 respiratory effect Effects 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
229920005989 resin Polymers 0.000 description 40
239000011347 resin Substances 0.000 description 40
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
RVWQQCKPTVZHJM-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylbutyric acid Chemical compound CC(O)C(C)(C)C(O)=O RVWQQCKPTVZHJM-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 7
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 7
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000000034 method Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
208000022559 Inflammatory bowel disease Diseases 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
230000000638 stimulation Effects 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
VXSUTXKJWJUPLJ-UHFFFAOYSA-N 2,4-dichloro-8-fluoroquinazoline Chemical compound N1=C(Cl)N=C2C(F)=CC=CC2=C1Cl VXSUTXKJWJUPLJ-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229920001807 Urea-formaldehyde Polymers 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000001022 anti-muscarinic effect Effects 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
230000004064 dysfunction Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
229940073584 methylene chloride Drugs 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
239000000651 prodrug Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 0.000 description 2
230000007017 scission Effects 0.000 description 2
210000002460 smooth muscle Anatomy 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
OJZYLUUHIAKDJT-UHFFFAOYSA-N 2,3-dihydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1O OJZYLUUHIAKDJT-UHFFFAOYSA-N 0.000 description 1
JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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 description 1
102000007527 Autoreceptors Human genes 0.000 description 1
108010071131 Autoreceptors Proteins 0.000 description 1
102000009660 Cholinergic Receptors Human genes 0.000 description 1
108010009685 Cholinergic Receptors Proteins 0.000 description 1
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
229910004373 HOAc Inorganic materials 0.000 description 1
206010021639 Incontinence Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
206010046543 Urinary incontinence Diseases 0.000 description 1
241000251539 Vertebrata <Metazoa> Species 0.000 description 1
230000036428 airway hyperreactivity Effects 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000031018 biological processes and functions Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
IFCMUYKWZSCFLB-UHFFFAOYSA-N carbonochloridic acid;nitrobenzene Chemical compound OC(Cl)=O.[O-][N+](=O)C1=CC=CC=C1 IFCMUYKWZSCFLB-UHFFFAOYSA-N 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
210000002932 cholinergic neuron Anatomy 0.000 description 1
DERZBLKQOCDDDZ-JLHYYAGUSA-N cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 description 1
230000009989 contractile response Effects 0.000 description 1
150000001942 cyclopropanes Chemical class 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
230000002964 excitative effect Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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 description 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 description 1
150000004677 hydrates Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000035873 hypermotility Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000003551 muscarinic effect Effects 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
210000005037 parasympathetic nerve Anatomy 0.000 description 1
230000001991 pathophysiological effect Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000011894 semi-preparative HPLC Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 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
238000002560 therapeutic procedure Methods 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
230000007384 vagal nerve stimulation Effects 0.000 description 1
WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- 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
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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Hydrogenated Pyridines (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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ZA200604485A 2003-12-03 2006-06-01 Novel M3 muscarinic acetylcholine receptor antagonists ZA200604485B (en)

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US52676603P	2003-12-03	2003-12-03

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ZA200604485B true ZA200604485B (en)	2007-11-28

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ZA200604485A ZA200604485B (en)	2003-12-03	2006-06-01	Novel M3 muscarinic acetylcholine receptor antagonists

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US (1)	US20070179180A1 (fr)
EP (1)	EP1694327A4 (fr)
JP (1)	JP2007513182A (fr)
KR (1)	KR20060123414A (fr)
CN (1)	CN1913895A (fr)
AR (1)	AR046783A1 (fr)
AU (1)	AU2004296208A1 (fr)
BR (1)	BRPI0417343A (fr)
CA (1)	CA2549273A1 (fr)
IL (1)	IL176078A0 (fr)
IS (1)	IS8522A (fr)
MA (1)	MA28218A1 (fr)
MX (1)	MXPA06006256A (fr)
NO (1)	NO20063032L (fr)
PE (1)	PE20050861A1 (fr)
RU (1)	RU2006123418A (fr)
TW (1)	TW200530226A (fr)
UY (1)	UY28646A1 (fr)
WO (1)	WO2005055941A2 (fr)
ZA (1)	ZA200604485B (fr)

Families Citing this family (22)

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TW200519108A (en) *	2003-07-17	2005-06-16	Glaxo Group Ltd	Muscarinic acetylcholine receptor antagonists
BRPI0415281A (pt) *	2003-10-17	2006-12-19	Glaxo Group Ltd	antagonistas de receptor de acetilcolina muscarìnico
PE20050489A1 (es) *	2003-11-04	2005-09-02	Glaxo Group Ltd	Antagonistas de receptores de acetilcolina muscarinicos
US20090253908A1 (en) *	2004-03-11	2009-10-08	Glaxo Group Limited	Novel m3 muscarinic acetylchoine receptor antagonists
EP1725238A4 (fr) *	2004-03-17	2009-04-01	Glaxo Group Ltd	Antagonistes du recepteur muscarinique a l'acetylcholine m 3
WO2005095407A1 (fr) *	2004-03-17	2005-10-13	Glaxo Group Limited	Antagonistes du recepteur d'acetylcholine muscarinique m3
PE20060259A1 (es)	2004-04-27	2006-03-25	Glaxo Group Ltd	Compuestos de quinuclidina como antagonistas del receptor de acetilcolina muscarinico
JP2007537261A (ja) *	2004-05-13	2007-12-20	グラクソ　グループ　リミテッド	ムスカリン性アセチルコリン受容体アンタゴニスト
TW200630337A (en) *	2004-10-14	2006-09-01	Euro Celtique Sa	Piperidinyl compounds and the use thereof
US7932247B2 (en) *	2004-11-15	2011-04-26	Glaxo Group Limited	M3 muscarinic acetylcholine receptor antagonists
WO2007016639A2 (fr) *	2005-08-02	2007-02-08	Glaxo Group Limited	Antagonistes des recepteurs de l' acetylcholine muscarinique m3
WO2007022351A2 (fr)	2005-08-18	2007-02-22	Glaxo Group Limited	Antagonistes de recepteurs d'acetylcholine muscarinique
WO2007110449A1 (fr) *	2006-03-29	2007-10-04	Euro-Celtique S.A.	Composés de benzènesulfonamide et utilisation de ceux-ci
US8937181B2 (en) *	2006-04-13	2015-01-20	Purdue Pharma L.P.	Benzenesulfonamide compounds and the use thereof
TW200815353A (en) *	2006-04-13	2008-04-01	Euro Celtique Sa	Benzenesulfonamide compounds and their use
ES2554646T3 (es) *	2007-02-23	2015-12-22	Theravance Biopharma R&D Ip, Llc	Compuestos de difenilmetilo de amonio cuaternario, de utilidad como antagonistas de receptores muscarínicos
US8399486B2 (en) *	2007-04-09	2013-03-19	Purdue Pharma L.P.	Benzenesulfonyl compounds and the use thereof
US8765736B2 (en) *	2007-09-28	2014-07-01	Purdue Pharma L.P.	Benzenesulfonamide compounds and the use thereof
AR070563A1 (es)	2008-02-06	2010-04-21	Glaxo Group Ltd	Compuesto de un biciclo condensado pirazol-piridin-amina, composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para el tratamiento de enfermedades respiratorias.
UY31637A1 (es)	2008-02-06	2009-08-03		Farmacoforos duales-antagonistas muscarinicos de pde4
PE20091553A1 (es)	2008-02-06	2009-10-30	Glaxo Group Ltd	Farmacoforos duales - antagonistas muscarinicos de pde4
WO2010094643A1 (fr)	2009-02-17	2010-08-26	Glaxo Group Limited	Dérivés de quinoline et applications associées dans la rhinite et l'urticaire

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US6482837B1 (en) *	1998-04-24	2002-11-19	University Of Rochester	Antimuscarinic compounds and methods for treatment of bladder diseases
US7576117B1 (en) *	1999-08-04	2009-08-18	Teijin Limited	Cyclic amine CCR3 antagonist
DE10063008A1 (de) *	2000-12-16	2002-06-20	Merck Patent Gmbh	Carbonsäureamidderivate
DE10201550A1 (de) *	2002-01-17	2003-07-31	Merck Patent Gmbh	Phenoxy-Piperidine

2004
- 2004-12-01 PE PE2004001184A patent/PE20050861A1/es not_active Application Discontinuation
- 2004-12-01 AR ARP040104478A patent/AR046783A1/es unknown
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- 2004-12-03 CN CNA2004800412735A patent/CN1913895A/zh active Pending
- 2004-12-03 MX MXPA06006256A patent/MXPA06006256A/es not_active Application Discontinuation
- 2004-12-03 WO PCT/US2004/040668 patent/WO2005055941A2/fr not_active Ceased
- 2004-12-03 US US10/581,229 patent/US20070179180A1/en not_active Abandoned
- 2004-12-03 BR BRPI0417343-0A patent/BRPI0417343A/pt not_active Application Discontinuation
- 2004-12-03 CA CA002549273A patent/CA2549273A1/fr not_active Abandoned
- 2004-12-03 EP EP04813056A patent/EP1694327A4/fr not_active Withdrawn
- 2004-12-03 KR KR1020067013263A patent/KR20060123414A/ko not_active Withdrawn
- 2004-12-03 AU AU2004296208A patent/AU2004296208A1/en not_active Abandoned
- 2004-12-03 RU RU2006123418/04A patent/RU2006123418A/ru not_active Application Discontinuation
- 2004-12-03 JP JP2006542826A patent/JP2007513182A/ja active Pending
2006
- 2006-05-31 IL IL176078A patent/IL176078A0/en unknown
- 2006-06-01 ZA ZA200604485A patent/ZA200604485B/en unknown
- 2006-06-02 MA MA29069A patent/MA28218A1/fr unknown
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Also Published As

Publication number	Publication date
CA2549273A1 (fr)	2005-06-23
MXPA06006256A (es)	2006-08-23
PE20050861A1 (es)	2005-12-10
WO2005055941A3 (fr)	2006-02-16
JP2007513182A (ja)	2007-05-24
EP1694327A2 (fr)	2006-08-30
NO20063032L (no)	2006-08-30
IL176078A0 (en)	2006-10-05
RU2006123418A (ru)	2008-01-10
AU2004296208A1 (en)	2005-06-23
MA28218A1 (fr)	2006-10-02
TW200530226A (en)	2005-09-16
KR20060123414A (ko)	2006-12-01
CN1913895A (zh)	2007-02-14
IS8522A (is)	2006-06-26
UY28646A1 (es)	2005-06-30
AR046783A1 (es)	2005-12-21
BRPI0417343A (pt)	2007-03-13
US20070179180A1 (en)	2007-08-02
EP1694327A4 (fr)	2009-11-25
WO2005055941A2 (fr)	2005-06-23

Publication	Publication Date	Title
ZA200604485B (en)	2007-11-28	Novel M3 muscarinic acetylcholine receptor antagonists
US6683074B1 (en)	2004-01-27	Cyclic amine derivatives-CCR-3 receptor antagonists
CA2760562C (fr)	2016-07-19	Inhibiteurs a mecanisme double pour le traitement de maladie
EP1434765B1 (fr)	2009-12-02	Piperidines substituees avec liaison selective au recepteur h3 de l'histamine
US6437147B1 (en)	2002-08-20	Imidazole compounds
ZA200604395B (en)	2007-10-31	Novel M3 Muscarinic Acetylcholine receptor antagonists
HRP20030748A2 (en)	2004-12-31	Derivatives of n-(arylsulfonyl)beta-aminoacids comprising a substituted aminomethyl group, the preparation method thereof and the pharmaceutical compositions containing same
NZ546012A (en)	2009-12-24	Bicyclic [3.1.0] derivatives as glycine transporter inhibitors
RS52234B (sr)	2012-10-31	3-(1,3-benzodioksol-5-il)-6-(4-ciklopropilpiperazin-1-il)-piridazin, njegove soli i solvati i njegova upotreba kao antagonista histamin h3 receptora
JP2007528420A (ja)	2007-10-11	新規ｍ３ムスカリン性アセチルコリン受容体アンタゴニスト
AU2013302319A1 (en)	2015-02-26	VEGFR3 inhibitors
US6339087B1 (en)	2002-01-15	Cyclic amine derivatives-CCR-3 receptor antagonists
WO2007018514A1 (fr)	2007-02-15	Nouveaux antagonistes récepteurs d’acétylcholine muscarinique m3
US7462631B2 (en)	2008-12-09	Thiophene-2-carboxamide derivatives, preparation and therapeutic application thereof
CN101300226B (zh)	2012-05-30	对组蛋白脱乙酰酶具有抑制活性的烷基氨甲酰基萘氧基辛烯酰基羟基酰胺衍生物及其制备方法
JP5064503B2 (ja)	2012-10-31	Ｇｌｙｔ１に対する阻害剤としての二環芳香族置換アミド
JP5142152B2 (ja)	2013-02-13	４，５−ジアリールピロール誘導体、この調製方法および治療におけるこの使用
CN109843379A (zh)	2019-06-04	取代脲及其制备和使用方法
JP5734948B2 (ja)	2015-06-17	３−アルコキシ−４，５−ジアリールチオフェン−２−カルボキサミドの誘導体、この調製およびこの治療的使用
WO2007001225A1 (fr)	2007-01-04	Modulateurs d'alpha 7
MXPA00008362A (en)	2001-07-31	2-arylethyl-(piperidin-4-ylmethyl)amine derivatives as muscarinic receptor antagonists