UA76131C2 - Quinuclidine carbamate derivatives and medicinal compositions containing said derivatives - Google Patents
Quinuclidine carbamate derivatives and medicinal compositions containing said derivatives Download PDFInfo
- Publication number
- UA76131C2 UA76131C2 UA2003065666A UA2003065666A UA76131C2 UA 76131 C2 UA76131 C2 UA 76131C2 UA 2003065666 A UA2003065666 A UA 2003065666A UA 2003065666 A UA2003065666 A UA 2003065666A UA 76131 C2 UA76131 C2 UA 76131C2
- Authority
- UA
- Ukraine
- Prior art keywords
- azoniabicyclo
- octane
- group
- bromide
- azabicyclo
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title description 22
- DSTLXMSUVMLNBP-UHFFFAOYSA-N 1-azoniabicyclo[2.2.2]octane;carbamate Chemical class NC(O)=O.C1CC2CCN1CC2 DSTLXMSUVMLNBP-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 249
- -1 furan-2-ylmethyl Chemical group 0.000 claims abstract description 111
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 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 abstract description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 238000006467 substitution reaction Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 185
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 180
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 126
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 48
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 208000023504 respiratory system disease Diseases 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- WKFZHVFBHYHYAK-UHFFFAOYSA-N benzyl(phenyl)carbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)CC1=CC=CC=C1 WKFZHVFBHYHYAK-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
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- 125000003118 aryl group Chemical group 0.000 claims description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
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- CEWKHVQYIATTIC-UHFFFAOYSA-N butyl(phenyl)carbamic acid Chemical compound CCCCN(C(O)=O)C1=CC=CC=C1 CEWKHVQYIATTIC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
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- CQAMPEQWAJLGTK-UHFFFAOYSA-N benzyl-(4-fluorophenyl)carbamic acid Chemical compound C=1C=C(F)C=CC=1N(C(=O)O)CC1=CC=CC=C1 CQAMPEQWAJLGTK-UHFFFAOYSA-N 0.000 claims description 3
- BAIBBRORQJDVKQ-UHFFFAOYSA-N benzyl-(4-methylphenyl)carbamic acid Chemical compound C1=CC(C)=CC=C1N(C(O)=O)CC1=CC=CC=C1 BAIBBRORQJDVKQ-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- UIMCAHUVQVVYPJ-UHFFFAOYSA-N pentyl(phenyl)carbamic acid Chemical compound CCCCCN(C(O)=O)C1=CC=CC=C1 UIMCAHUVQVVYPJ-UHFFFAOYSA-N 0.000 claims description 3
- OLTPKMBOLARPFC-UHFFFAOYSA-N phenyl(2-phenylethyl)carbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)CCC1=CC=CC=C1 OLTPKMBOLARPFC-UHFFFAOYSA-N 0.000 claims description 3
- MZEJYTHCXCYSHD-UHFFFAOYSA-N phenyl(thiophen-2-ylmethyl)carbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)CC1=CC=CS1 MZEJYTHCXCYSHD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
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- XWDAJKMDKMCFKY-UHFFFAOYSA-N bis(furan-2-ylmethyl)carbamic acid Chemical compound O1C(=CC=C1)CN(C(O)=O)CC=1OC=CC1 XWDAJKMDKMCFKY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
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- 108020003175 receptors Proteins 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
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- A61P11/00—Drugs for disorders of the respiratory system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/14—Antitussive agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200003084 | 2000-12-22 | ||
| PCT/EP2001/015169 WO2002051841A1 (en) | 2000-12-22 | 2001-12-20 | Quinuclidine carbamate derivatives and their use as m3 antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA76131C2 true UA76131C2 (en) | 2006-07-17 |
Family
ID=8496114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003065666A UA76131C2 (en) | 2000-12-22 | 2001-12-20 | Quinuclidine carbamate derivatives and medicinal compositions containing said derivatives |
Country Status (33)
| Country | Link |
|---|---|
| US (3) | US7208501B2 (ja) |
| EP (1) | EP1345937B1 (ja) |
| JP (1) | JP4445704B2 (ja) |
| KR (1) | KR100869722B1 (ja) |
| CN (1) | CN1298717C (ja) |
| AR (1) | AR035410A1 (ja) |
| AT (1) | ATE305468T1 (ja) |
| AU (1) | AU2002228015B2 (ja) |
| BG (1) | BG107930A (ja) |
| BR (1) | BR0116450A (ja) |
| CA (1) | CA2441896A1 (ja) |
| CZ (1) | CZ301323B6 (ja) |
| DE (1) | DE60113719T2 (ja) |
| DK (1) | DK1345937T3 (ja) |
| EC (1) | ECSP034660A (ja) |
| EE (1) | EE200300295A (ja) |
| ES (1) | ES2248409T3 (ja) |
| HK (1) | HK1055120A1 (ja) |
| HU (1) | HUP0303529A3 (ja) |
| IL (1) | IL156499A0 (ja) |
| MX (1) | MXPA03005583A (ja) |
| MY (1) | MY136674A (ja) |
| NO (1) | NO328707B1 (ja) |
| NZ (1) | NZ526580A (ja) |
| PE (1) | PE20020719A1 (ja) |
| PL (1) | PL362989A1 (ja) |
| RU (1) | RU2296762C2 (ja) |
| SI (1) | SI1345937T1 (ja) |
| SK (1) | SK8002003A3 (ja) |
| UA (1) | UA76131C2 (ja) |
| UY (1) | UY27092A1 (ja) |
| WO (1) | WO2002051841A1 (ja) |
| ZA (1) | ZA200304769B (ja) |
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| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| PT1300407E (pt) * | 2000-06-27 | 2004-05-31 | S A L V A T Lab Sa | Compostos carbamatos derivados de arilalquilaminas |
| DK1345937T3 (da) | 2000-12-22 | 2006-01-16 | Almirall Prodesfarma Ag | Quinuclidincarbamatderivater og deres anvendelse som M3-antagonister |
| EE05404B1 (et) | 2000-12-28 | 2011-04-15 | Almirall Prodesfarma Ag | Kinuklidiini derivaat, selle saamine ja kasutamine ravimi valmistamiseks, mis on ette nhtud respiratoorsete, kuseelundite v?i mao-soolte haiguste ravimiseks, ning seda sisaldav ravimkompositsioon |
| NZ533259A (en) | 2001-12-14 | 2007-10-26 | Targacept Inc | Methods and compositions for treatment of central nervous system disorders |
| US7452904B2 (en) * | 2001-12-20 | 2008-11-18 | Chiesi Farmaceutici S.P.A. | 1-alkyl-1-azoniabicyclo' 2.2.2 octane carbamate derivatives and their use as muscarinic receptor antagonists |
| ES2203327B1 (es) * | 2002-06-21 | 2005-06-16 | Almirall Prodesfarma, S.A. | Nuevos carbamatos de quinuclidina y composiciones farmaceuticas que los contienen. |
| ES2204295B1 (es) * | 2002-07-02 | 2005-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de quinuclidina-amida. |
| EA200500173A1 (ru) * | 2002-07-08 | 2005-08-25 | Рэнбакси Лабораториз Лимитед | Производные 3,6-дизамещенного азабицикло[3.1.0]гексана в качестве антагонистов мускариновых рецепторов |
| TW200800953A (en) | 2002-10-30 | 2008-01-01 | Theravance Inc | Intermediates for preparing substituted 4-amino-1-(pyridylmethyl) piperidine |
| PE20040950A1 (es) | 2003-02-14 | 2005-01-01 | Theravance Inc | DERIVADOS DE BIFENILO COMO AGONISTAS DE LOS RECEPTORES ADRENERGICOS ß2 Y COMO ANTAGONISTAS DE LOS RECEPTORES MUSCARINICOS |
| US7517905B2 (en) | 2003-04-09 | 2009-04-14 | Ranbaxy Laboratories Limited | Substituted azabicyclo hexane derivatives as muscarinic receptor antagonists |
| EP1626957A1 (en) | 2003-04-11 | 2006-02-22 | Ranbaxy Laboratories Limited | Azabicyclo derivatives as muscarinic receptor antagonists |
| AR044519A1 (es) | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
| US7358244B2 (en) | 2003-05-28 | 2008-04-15 | Theravance, Inc. | Azabicycloalkane compounds |
| WO2005007645A1 (en) | 2003-07-11 | 2005-01-27 | Theravance, Inc. | Substituted 4-amino-1-benzylpiperidine compounds |
| CA2543858C (en) | 2003-11-21 | 2014-04-15 | Theravance, Inc. | Compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| GB0401334D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
| WO2005087733A1 (en) | 2004-03-11 | 2005-09-22 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| US7456199B2 (en) | 2004-03-11 | 2008-11-25 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
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| JP2007528415A (ja) | 2004-03-11 | 2007-10-11 | セラヴァンス， インコーポレーテッド | ムスカリンレセプターアンタゴニストとしての有用なビフェニル化合物 |
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| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
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| EP1882691A1 (en) | 2006-07-26 | 2008-01-30 | CHIESI FARMACEUTICI S.p.A. | Quinuclidine derivatives as M3 antagonists |
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