UA80832C2 - Quinuclidine amide derivatives - Google Patents

Quinuclidine amide derivatives Download PDF

Info

Publication number: UA80832C2
Authority: UA; Ukraine
Prior art keywords: hydroxy; octane; azoniumbicyclo; group; azabicyclo
Prior art date: 2002-07-02

Application number

UAA200500839A

Other languages

English (en)

Ukrainian (uk)

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.)

2002-07-02

Filing date

2003-06-25

Publication date

2007-11-12

2003-06-25 Application filed filed Critical

2007-11-12 Publication of UA80832C2 publication Critical patent/UA80832C2/uk

Links

-1 Quinuclidine amide Chemical class 0.000 title claims abstract description 57
238000000034 method Methods 0.000 claims abstract description 106
238000002360 preparation method Methods 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims abstract description 11
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims abstract description 11
239000005557 antagonist Substances 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 207
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 139
239000000203 mixture Substances 0.000 claims description 89
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 75
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 64
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 26
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
125000000175 2-thienyl group Chemical class S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 15
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000004122 cyclic group Chemical group 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 14
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 13
NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical group 0.000 claims description 11
208000023504 respiratory system disease Diseases 0.000 claims description 10
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 9
125000003368 amide group Chemical group 0.000 claims description 9
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 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
125000000623 heterocyclic group Chemical group 0.000 claims description 9
125000002941 2-furyl group Chemical class O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
208000018522 Gastrointestinal disease Diseases 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 8
208000014001 urinary system disease Diseases 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 7
230000000241 respiratory effect Effects 0.000 claims description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
229920002554 vinyl polymer Polymers 0.000 claims description 7
OZCJTNLELXWUTQ-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octane-2-carboxamide Chemical group C1CN2C(C(=O)N)CC1CC2 OZCJTNLELXWUTQ-UHFFFAOYSA-N 0.000 claims description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000003682 3-furyl group Chemical class O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
125000001541 3-thienyl group Chemical class S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
208000012931 Urologic disease Diseases 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 6
208000010643 digestive system disease Diseases 0.000 claims description 6
208000035475 disorder Diseases 0.000 claims description 6
208000018685 gastrointestinal system disease Diseases 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
125000005605 benzo group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000012634 fragment Substances 0.000 claims description 4
229940126601 medicinal product Drugs 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000006017 1-propenyl group Chemical group 0.000 claims description 3
239000000556 agonist Substances 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
239000000043 antiallergic agent Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
230000003993 interaction Effects 0.000 claims description 3
150000002617 leukotrienes Chemical class 0.000 claims description 3
150000003431 steroids Chemical class 0.000 claims description 3
208000024891 symptom Diseases 0.000 claims description 3
125000001462 1-pyrrolyl group Chemical class [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
239000003112 inhibitor Substances 0.000 claims description 2
150000002902 organometallic compounds Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
230000001575 pathological effect Effects 0.000 claims 5
230000003042 antagnostic effect Effects 0.000 claims 2
239000013066 combination product Substances 0.000 claims 2
229940127555 combination product Drugs 0.000 claims 2
125000004214 1-pyrrolidinyl group Chemical class [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
241000282465 Canis Species 0.000 claims 1
241001024304 Mino Species 0.000 claims 1
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims 1
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims 1
230000008485 antagonism Effects 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 3
238000002560 therapeutic procedure Methods 0.000 abstract 1
238000004949 mass spectrometry Methods 0.000 description 70
239000000243 solution Substances 0.000 description 43
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
238000005160 1H NMR spectroscopy Methods 0.000 description 31
238000005481 NMR spectroscopy Methods 0.000 description 30
239000000047 product Substances 0.000 description 29
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
230000035484 reaction time Effects 0.000 description 12
238000010992 reflux Methods 0.000 description 12
238000005406 washing Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 11
239000002904 solvent Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
239000003480 eluent Substances 0.000 description 10
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
239000011780 sodium chloride Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
239000012047 saturated solution Substances 0.000 description 7
IDCLTMRSSAXUNY-UHFFFAOYSA-N 5-hydroxylansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC(O)=CC=C2N1 IDCLTMRSSAXUNY-UHFFFAOYSA-N 0.000 description 6
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000008101 lactose Substances 0.000 description 6
239000002552 dosage form Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
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208000009079 Bronchial Spasm Diseases 0.000 description 4
208000014181 Bronchial disease Diseases 0.000 description 4
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GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
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XOFMKTIZCDSXFR-UHFFFAOYSA-N 2,2-dithiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(C(=O)O)C1=CC=CS1 XOFMKTIZCDSXFR-UHFFFAOYSA-N 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
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241000700198 Cavia Species 0.000 description 3
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238000004458 analytical method Methods 0.000 description 3
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
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YLMOPFHUYOWWOX-UHFFFAOYSA-N 2-(5-bromothiophen-2-yl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(Br)S1 YLMOPFHUYOWWOX-UHFFFAOYSA-N 0.000 description 2
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PMCNGVWJGLTDLF-UHFFFAOYSA-N 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(O)(C(=O)O)C1CCCC1 PMCNGVWJGLTDLF-UHFFFAOYSA-N 0.000 description 2
PGIOANNVJQQCDT-UHFFFAOYSA-N 2-phenylhexanoic acid Chemical compound CCCCC(C(O)=O)C1=CC=CC=C1 PGIOANNVJQQCDT-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

UAA200500839A 2002-07-02 2003-06-25 Quinuclidine amide derivatives UA80832C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES200201539A ES2204295B1 (es)	2002-07-02	2002-07-02	Nuevos derivados de quinuclidina-amida.
PCT/EP2003/006708 WO2004005285A1 (en)	2002-07-02	2003-06-25	New quinuclidine amide derivatives

Publications (1)

Publication Number	Publication Date
UA80832C2 true UA80832C2 (en)	2007-11-12

Family

ID=30011350

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200500839A UA80832C2 (en)	2002-07-02	2003-06-25	Quinuclidine amide derivatives

Country Status (24)

Country	Link
US (2)	US7488735B2 (es)
EP (1)	EP1519933B1 (es)
JP (1)	JP2005533826A (es)
CN (1)	CN100404533C (es)
AR (1)	AR040351A1 (es)
AT (1)	ATE467631T1 (es)
AU (1)	AU2003242757B2 (es)
BR (1)	BR0312216A (es)
CA (1)	CA2492535A1 (es)
DE (1)	DE60332534D1 (es)
EC (1)	ECSP045519A (es)
ES (1)	ES2204295B1 (es)
IL (1)	IL165923A (es)
MX (1)	MXPA04012271A (es)
MY (1)	MY130803A (es)
NO (1)	NO20050164L (es)
NZ (1)	NZ537341A (es)
PE (1)	PE20040644A1 (es)
RU (1)	RU2314306C2 (es)
TW (1)	TW200402420A (es)
UA (1)	UA80832C2 (es)
UY (1)	UY27870A1 (es)
WO (1)	WO2004005285A1 (es)
ZA (1)	ZA200410404B (es)

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2003
- 2003-06-25 MX MXPA04012271A patent/MXPA04012271A/es active IP Right Grant
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- 2003-06-25 UA UAA200500839A patent/UA80832C2/uk unknown
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- 2003-06-25 WO PCT/EP2003/006708 patent/WO2004005285A1/en active Application Filing
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Publication number	Publication date
NO20050164L (no)	2005-04-04
CA2492535A1 (en)	2004-01-15
CN1678610A (zh)	2005-10-05
ES2204295A1 (es)	2004-04-16
TW200402420A (en)	2004-02-16
CN100404533C (zh)	2008-07-23
MXPA04012271A (es)	2005-04-08
ECSP045519A (es)	2005-03-10
US20080234316A1 (en)	2008-09-25
IL165923A (en)	2010-06-30
BR0312216A (pt)	2005-04-12
ZA200410404B (en)	2005-09-05
ATE467631T1 (de)	2010-05-15
US7718670B2 (en)	2010-05-18
AU2003242757B2 (en)	2009-01-08
MY130803A (en)	2007-07-31
RU2005102585A (ru)	2005-10-10
US20060167042A1 (en)	2006-07-27
PE20040644A1 (es)	2004-09-18
EP1519933A1 (en)	2005-04-06
AU2003242757A1 (en)	2004-01-23
IL165923A0 (en)	2006-01-15
US7488735B2 (en)	2009-02-10
AR040351A1 (es)	2005-03-30
JP2005533826A (ja)	2005-11-10
EP1519933B1 (en)	2010-05-12
UY27870A1 (es)	2003-10-31
DE60332534D1 (de)	2010-06-24
NZ537341A (en)	2006-04-28
WO2004005285A1 (en)	2004-01-15
ES2204295B1 (es)	2005-08-01
RU2314306C2 (ru)	2008-01-10

Publication	Publication Date	Title
UA80832C2 (en)	2007-11-12	Quinuclidine amide derivatives
RU2282629C2 (ru)	2006-08-27	Производные хинуклидина, способ их получения и фармацевтическая композиция на их основе
EP1345937B1 (en)	2005-09-28	Quinuclidine carbamate derivatives and their use as m3 antagonists
RU2382041C2 (ru)	2010-02-20	Новые сложные эфиры кватернизованного хинуклидина
ES2203327B1 (es)	2005-06-16	Nuevos carbamatos de quinuclidina y composiciones farmaceuticas que los contienen.
CA3196582A1 (en)	2022-05-05	Bicyclic compounds and uses thereof for the treatment of diseases
WO2023114456A1 (en)	2023-06-22	Uses of bicyclic compounds for the treatment of diseases
TWI304067B (en)	2008-12-11	Novel quinuclidine carbamate derivatives and medicinal compositions containing the same
KR20050024450A (ko)	2005-03-10	신규한 퀴누클리딘 아미드 유도체