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
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- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
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- 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
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- 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
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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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- 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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- 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)
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- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- 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 (32)
| Country | Link |
|---|---|
| US (3) | US7208501B2 (cs) |
| EP (1) | EP1345937B1 (cs) |
| JP (1) | JP4445704B2 (cs) |
| KR (1) | KR100869722B1 (cs) |
| CN (1) | CN1298717C (cs) |
| AR (1) | AR035410A1 (cs) |
| AT (1) | ATE305468T1 (cs) |
| AU (1) | AU2002228015B2 (cs) |
| BG (1) | BG107930A (cs) |
| BR (1) | BR0116450A (cs) |
| CA (1) | CA2441896A1 (cs) |
| CZ (1) | CZ301323B6 (cs) |
| DE (1) | DE60113719T2 (cs) |
| DK (1) | DK1345937T3 (cs) |
| EC (1) | ECSP034660A (cs) |
| EE (1) | EE200300295A (cs) |
| ES (1) | ES2248409T3 (cs) |
| HU (1) | HUP0303529A3 (cs) |
| IL (1) | IL156499A0 (cs) |
| MX (1) | MXPA03005583A (cs) |
| MY (1) | MY136674A (cs) |
| NO (1) | NO328707B1 (cs) |
| NZ (1) | NZ526580A (cs) |
| PE (1) | PE20020719A1 (cs) |
| PL (1) | PL362989A1 (cs) |
| RU (1) | RU2296762C2 (cs) |
| SI (1) | SI1345937T1 (cs) |
| SK (1) | SK8002003A3 (cs) |
| UA (1) | UA76131C2 (cs) |
| UY (1) | UY27092A1 (cs) |
| WO (1) | WO2002051841A1 (cs) |
| ZA (1) | ZA200304769B (cs) |
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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. |
| DK1300407T4 (da) * | 2000-06-27 | 2011-09-05 | S A L V A T Lab Sa | Carbamater afledt af arylalkylaminer |
| HUP0303529A3 (en) | 2000-12-22 | 2008-03-28 | Almirall Ag | New quinuclidine carbamate derivatives, process for their preparation and pharmaceutical compositions containing them and their use |
| PL363807A1 (en) | 2000-12-28 | 2004-11-29 | Almirall Prodesfarma Ag | Novel quinuclidine derivatives and medicinal compositions containing the same |
| BR0214929A (pt) | 2001-12-14 | 2006-05-30 | Targacept Inc | métodos e composições para o tratamento de distúrbios do sistema nervoso central |
| JP4505227B2 (ja) * | 2001-12-20 | 2010-07-21 | キエシ・フアルマチエウテイチ・ソチエタ・ペル・アチオニ | １−アルキル−１−アゾニアビシクロ［２．２．２］オクタンカルバメート誘導体およびムスカリンレセプターアンタゴニストとしてのそれらの使用 |
| 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 |
| TWI295669B (en) | 2002-10-30 | 2008-04-11 | Theravance Inc | Substituted 4-amino-1-(pyridylmethyl) piperidine and related compounds |
| 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 |
| AU2003214520A1 (en) | 2003-04-09 | 2004-11-01 | Ranbaxy Laboratories Limited | Substituted azabicyclo hexane derivatives as muscarinic receptor antagonists |
| JP2006522787A (ja) | 2003-04-11 | 2006-10-05 | ランバクシー ラボラトリーズ リミテッド | ムスカリン様受容体アンタゴニストとしてのアザビシクロ誘導体 |
| AR044519A1 (es) | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
| EP1626970B1 (en) | 2003-05-28 | 2009-07-08 | Theravance, Inc. | Azabicycloalkane compounds as muscarinic receptor antagonists |
| EP1644356A1 (en) | 2003-07-11 | 2006-04-12 | Theravance, Inc. | Substituted 4-amino-1-benzylpiperidine compounds |
| JP4851937B2 (ja) | 2003-11-21 | 2012-01-11 | セラヴァンス， インコーポレーテッド | β２アドレナリン作動性受容体作動薬活性およびムスカリン受容体拮抗薬活性を有する化合物 |
| GB0401334D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
| EP1723113A1 (en) | 2004-03-11 | 2006-11-22 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| JP2007528416A (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 |
| US7262205B2 (en) | 2004-03-11 | 2007-08-28 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| TWI341836B (en) | 2004-03-11 | 2011-05-11 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
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| JP2007528412A (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有用なビフェニル化合物 |
| JP2007528410A (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 |
| 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 |
| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| ES2246170B1 (es) * | 2004-07-29 | 2007-04-01 | Almirall Prodesfarma, S.A. | Nuevo procedimiento para preparar derivados de carbamato de quinuclidinio. |
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
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| GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| JP2008537931A (ja) | 2005-03-10 | 2008-10-02 | セラヴァンス， インコーポレーテッド | ムスカリン性レセプターアンタゴニストとして有用なビフェニル化合物 |
| WO2006099032A1 (en) | 2005-03-10 | 2006-09-21 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
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| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
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| RU2457209C2 (ru) | 2006-04-21 | 2012-07-27 | Новартис Аг | Производные пурина, предназначенные для применения в качестве агонистов аденозинового рецептора а2а |
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| EP1882691A1 (en) * | 2006-07-26 | 2008-01-30 | CHIESI FARMACEUTICI S.p.A. | Quinuclidine derivatives as M3 antagonists |
| MX2009003185A (es) | 2006-09-29 | 2009-04-03 | Novartis Ag | Pirazolopirimidinas como inhibidores de lipido cinasa pi3k. |
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| US20090010923A1 (en) * | 2007-04-24 | 2009-01-08 | University Of Maryland, Baltimore | Treatment of cancer with anti-muscarinic receptor agents |
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| EP2065385A1 (en) * | 2007-11-28 | 2009-06-03 | Laboratorios SALVAT, S.A. | Stable crystalline salt of (R)-3-fluorophenyl-3,4,5-trifluorobenzylcarbamic acid 1-azabiciyclo [2.2.2]oct-3-yl ester |
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