AU685225B2 - Novel carbamate derivative and medicinal composition containing the same - Google Patents
Novel carbamate derivative and medicinal composition containing the same Download PDFInfo
- Publication number
- AU685225B2 AU685225B2 AU15909/95A AU1590995A AU685225B2 AU 685225 B2 AU685225 B2 AU 685225B2 AU 15909/95 A AU15909/95 A AU 15909/95A AU 1590995 A AU1590995 A AU 1590995A AU 685225 B2 AU685225 B2 AU 685225B2
- Authority
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- Australia
- Prior art keywords
- group
- ring
- carbamate
- compound
- represented
- Prior art date
- Legal status (The legal status 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 status listed.)
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- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 title description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 13
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
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- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
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- 125000003277 amino group Chemical group 0.000 claims description 7
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
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- 239000007864 aqueous solution Substances 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 13
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 13
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- 238000010438 heat treatment Methods 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 230000027455 binding Effects 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 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 10
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- 229910052739 hydrogen Inorganic materials 0.000 description 10
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- 206010006482 Bronchospasm Diseases 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 7
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- 208000026451 salivation Diseases 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
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
-
- 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—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
- C07D405/02—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1682994 | 1994-02-10 | ||
| JP6-16829 | 1994-02-10 | ||
| JP6-35064 | 1994-03-04 | ||
| JP3506494 | 1994-03-04 | ||
| JP10257994 | 1994-05-17 | ||
| JP6-102579 | 1994-05-17 | ||
| JP6-221335 | 1994-09-16 | ||
| JP22133594 | 1994-09-16 | ||
| JP26741294 | 1994-10-31 | ||
| JP6-267412 | 1994-10-31 | ||
| PCT/JP1995/000168 WO1995021820A1 (en) | 1994-02-10 | 1995-02-08 | Novel carbamate derivative and medicinal composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1590995A AU1590995A (en) | 1995-08-29 |
| AU685225B2 true AU685225B2 (en) | 1998-01-15 |
Family
ID=27519861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU15909/95A Expired - Fee Related AU685225B2 (en) | 1994-02-10 | 1995-02-08 | Novel carbamate derivative and medicinal composition containing the same |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0747355A4 (enExample) |
| KR (1) | KR970701174A (enExample) |
| AU (1) | AU685225B2 (enExample) |
| CA (1) | CA2182568A1 (enExample) |
| HU (1) | HUT76289A (enExample) |
| TW (1) | TW322478B (enExample) |
| WO (1) | WO1995021820A1 (enExample) |
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|---|---|---|---|---|
| CA2249410C (en) * | 1996-03-20 | 2007-06-12 | Wake Forest University | Sigma-2 receptors as biomarkers of tumor cell proliferation |
| WO1998054167A1 (en) * | 1997-05-28 | 1998-12-03 | Mitsubishi-Tokyo Pharmaceuticals, Inc. | Indole compounds |
| SK11402000A3 (sk) * | 1998-02-04 | 2001-03-12 | Banyu Pharmaceutical Co., Ltd | Cyklické n-acylaminoderiváty |
| US6693202B1 (en) | 1999-02-16 | 2004-02-17 | Theravance, Inc. | Muscarinic receptor antagonists |
| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| US7214687B2 (en) | 1999-07-14 | 2007-05-08 | Almirall Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| CA2380074C (en) * | 1999-07-23 | 2009-04-28 | Banyu Pharmaceutical Co., Ltd. | Novel amide derivatives |
| JP2003516390A (ja) * | 1999-12-07 | 2003-05-13 | 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活性を有するカルバメート誘導体 |
| UA73543C2 (uk) | 1999-12-07 | 2005-08-15 | Тераванс, Інк. | Похідні сечовини, фармацевтична композиція та застосування похідного при приготуванні лікарського засобу для лікування захворювання, яке опосередковується мускариновим рецептором |
| CA2407520C (en) | 2000-04-27 | 2010-02-02 | Wake Forest University Health Sciences | Sigma-2 receptors as biomarkers of tumor cell proliferation |
| BR0112297A (pt) * | 2000-06-27 | 2003-05-06 | S A L V A T Lab Sa | Compostos carbamatos derivados de arilalquilaminas |
| EP1345937B1 (en) * | 2000-12-22 | 2005-09-28 | Almirall Prodesfarma AG | Quinuclidine carbamate derivatives and their use as m3 antagonists |
| 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 |
| WO2003037317A1 (en) * | 2001-10-26 | 2003-05-08 | Dey, L.P. | Albuterol inhalation solution, system, kit and method for relieving symptoms of pediatric asthma |
| PL211250B1 (pl) * | 2001-12-20 | 2012-04-30 | Chiesi Farma Spa | Pochodne karbaminianu 1-alkilo-1-azoniabicyklo [2.2.2] oktanu, jej zastosowania, kompozycja farmaceutyczna zawierająca ten związek oraz związek pośredni |
| ES2416304T3 (es) | 2002-01-18 | 2013-07-31 | Astellas Pharma Inc. | Derivado de 2-acilaminotiazol o sal del mismo |
| 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. |
| DE10255040A1 (de) * | 2002-11-26 | 2004-06-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Carbaminsäureester mit anticholinerger Wirksamkeit |
| US7041674B2 (en) * | 2002-11-26 | 2006-05-09 | Boehringer Ingelhiem Pharma Gmbh & Co. Kg | Carbamic acid esters with anticholinergic activity |
| 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 |
| DE602004021959D1 (de) | 2003-11-21 | 2009-08-20 | Theravance Inc | Verbindungen mit agonistischer wirkung am beta2-adrenergen rezeptor und am muscarinischen rezeptor |
| TW200534855A (en) * | 2004-01-13 | 2005-11-01 | Glaxo Group Ltd | Muscarinic acetylcholine receptor antagonists |
| US7456199B2 (en) | 2004-03-11 | 2008-11-25 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| TW200538095A (en) | 2004-03-11 | 2005-12-01 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
| US7501442B2 (en) | 2004-03-11 | 2009-03-10 | 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 |
| US7524962B2 (en) | 2004-03-11 | 2009-04-28 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| 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 |
| WO2005087736A1 (en) | 2004-03-11 | 2005-09-22 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| 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 |
| WO2006023457A1 (en) | 2004-08-16 | 2006-03-02 | Theravance, Inc. | COMPOUNDS HAVING β2 ADRENERGIC RECEPTOR AGONIST AND MUSCARINIC RECEPTOR ANTAGONIST ACTIVITY |
| WO2006023460A2 (en) | 2004-08-16 | 2006-03-02 | Theravance, Inc. | COMPOUNDS HAVING β2 ADRENERGIC RECEPTOR AGONIST AND MUSCARINIC RECEPTOR ANTAGONIST ACTIVITY |
| US7659403B2 (en) | 2005-03-10 | 2010-02-09 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| TWI372749B (en) | 2005-03-10 | 2012-09-21 | Theravance Inc | Crystalline forms of a biphenyl compound |
| US7642355B2 (en) | 2005-03-10 | 2010-01-05 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| EP1856112A1 (en) | 2005-03-10 | 2007-11-21 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| TW200714587A (en) | 2005-03-10 | 2007-04-16 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
| US7479562B2 (en) | 2005-03-10 | 2009-01-20 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| US7728144B2 (en) | 2005-06-13 | 2010-06-01 | Theravance, Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
| EP1904446A2 (en) * | 2005-07-11 | 2008-04-02 | Ranbaxy Laboratories Limited | Azabicyclo derivatives as muscarinic receptor antagonists |
| GB0602778D0 (en) | 2006-02-10 | 2006-03-22 | Glaxo Group Ltd | Novel compound |
| US7973055B2 (en) | 2006-03-09 | 2011-07-05 | Theravance, Inc. | Crystalline forms of a biphenyl compound |
| TW200811104A (en) | 2006-04-25 | 2008-03-01 | Theravance Inc | Crystalline forms of a dimethylphenyl compound |
| TW200811105A (en) | 2006-04-25 | 2008-03-01 | Theravance Inc | Dialkylphenyl compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| ES2298049B1 (es) | 2006-07-21 | 2009-10-20 | Laboratorios Almirall S.A. | Procedimiento para fabricar bromuro de 3(r)-(2-hidroxi-2,2-ditien-2-ilacetoxi)-1-(3-fenoxipropil)-1-azoniabiciclo (2.2.2) octano. |
| US20100144801A1 (en) * | 2006-10-03 | 2010-06-10 | Naresh Kumar | Muscarinic receptor antagonists |
| CA2678193A1 (en) | 2007-02-09 | 2008-08-14 | Astellas Pharma Inc. | Aza-bridged-ring compound |
| WO2008118742A1 (en) * | 2007-03-23 | 2008-10-02 | Abbott Laboratories | Azaadamantane ester and carbamate derivatives and methods of use thereof |
| EP2100599A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2100598A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2206712A1 (en) * | 2008-12-23 | 2010-07-14 | CHIESI FARMACEUTICI S.p.A. | "Alkaloid aminoester derivatives and medicinal composition thereof" |
| PL2453894T3 (pl) | 2009-07-15 | 2016-04-29 | Theravance Biopharma R&D Ip Llc | Postać krystaliczna wolnej zasady związku bifenylowego |
| US9133116B2 (en) | 2010-09-28 | 2015-09-15 | Panacea Biotec Ltd. | Bicyclic compounds |
| BR112013012160A2 (pt) * | 2010-11-26 | 2019-09-24 | Chiesi Farm Spa | compostos, composição farmacêutica, uso de um composto e dispositivo |
| UA118248C2 (uk) * | 2011-03-18 | 2018-12-26 | Джензім Корпорейшн | Інгібітори глюкозилцерамідсинтази |
| EP2510928A1 (en) | 2011-04-15 | 2012-10-17 | Almirall, S.A. | Aclidinium for use in improving the quality of sleep in respiratory patients |
| MA37975B2 (fr) * | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| SG11201506415XA (en) * | 2013-03-15 | 2015-09-29 | Genzyme Corp | Method of preparing glucosylceramide synthase inhibitors |
| KR101538846B1 (ko) * | 2013-07-30 | 2015-07-22 | 동아에스티 주식회사 | 신규한 바이페닐 유도체 및 그의 제조방법 |
| WO2017114377A1 (zh) * | 2015-12-29 | 2017-07-06 | 四川海思科制药有限公司 | 一种苯基杂环衍生物及其在医药上的用途 |
| KR102239776B1 (ko) * | 2016-08-26 | 2021-04-13 | 동아에스티 주식회사 | (r)-(1-메틸피롤리딘-3-일)메틸(3'-클로로-4'-플루오로-[1,1'-비페닐]-2-일)카바메이트의 신규염 및 이의 결정형 |
| MX389419B (es) * | 2016-08-26 | 2025-03-20 | Dong A St Co Ltd | Nueva sal de (r)-(1-metilpirrolidin-3-il) metil (3'-chloro-4'-fluoro- [1,1'-bifenil]-2-il) carbamato y una forma cristalina del misma |
| EP3710483A4 (en) | 2017-11-16 | 2021-10-20 | XL-protein GmbH | PASYLATED VEGFR / PDGFR FUSION PROTEINS AND THEIR USE IN THERAPY |
| EP3720852A1 (en) * | 2017-12-04 | 2020-10-14 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Fluorophenyl substituted muscarinic receptor ligands with selectivity for m3 over m2 |
| US12083115B2 (en) | 2020-02-03 | 2024-09-10 | Genzyme Corporation | Methods for treating neurological symptoms associated with lysosomal storage diseases |
| BR112023000798A2 (pt) | 2020-07-24 | 2023-02-07 | Genzyme Corp | Composições farmacêuticas compreendendo venglustat |
| CN115850157A (zh) * | 2022-11-30 | 2023-03-28 | 济南大学 | 一种1-苄基哌啶-4-基[1,1'-联苯]-2-基氨基甲酸酯的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993020071A1 (en) * | 1992-03-31 | 1993-10-14 | Glaxo Group Limited | Substituted phenylcarbamates and phenylureas, their preparation and their use as 5-ht antagonists |
-
1995
- 1995-02-08 KR KR1019960704353A patent/KR970701174A/ko not_active Withdrawn
- 1995-02-08 AU AU15909/95A patent/AU685225B2/en not_active Expired - Fee Related
- 1995-02-08 CA CA002182568A patent/CA2182568A1/en not_active Abandoned
- 1995-02-08 HU HU9602188A patent/HUT76289A/hu unknown
- 1995-02-08 WO PCT/JP1995/000168 patent/WO1995021820A1/ja not_active Ceased
- 1995-02-08 EP EP95907855A patent/EP0747355A4/en not_active Withdrawn
- 1995-02-09 TW TW084101083A patent/TW322478B/zh active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993020071A1 (en) * | 1992-03-31 | 1993-10-14 | Glaxo Group Limited | Substituted phenylcarbamates and phenylureas, their preparation and their use as 5-ht antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2182568A1 (en) | 1995-08-17 |
| TW322478B (enExample) | 1997-12-11 |
| HU9602188D0 (en) | 1996-10-28 |
| EP0747355A1 (en) | 1996-12-11 |
| AU1590995A (en) | 1995-08-29 |
| WO1995021820A1 (en) | 1995-08-17 |
| KR970701174A (ko) | 1997-03-17 |
| EP0747355A4 (en) | 1997-04-09 |
| HUT76289A (en) | 1997-07-28 |
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