JP2012511580A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012511580A5 JP2012511580A5 JP2011540855A JP2011540855A JP2012511580A5 JP 2012511580 A5 JP2012511580 A5 JP 2012511580A5 JP 2011540855 A JP2011540855 A JP 2011540855A JP 2011540855 A JP2011540855 A JP 2011540855A JP 2012511580 A5 JP2012511580 A5 JP 2012511580A5
- Authority
- JP
- Japan
- Prior art keywords
- solid form
- crystalline solid
- cyclohexylmethyl
- diethyl
- methoxy
- 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.)
- Granted
Links
- 239000007787 solid Substances 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 19
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 16
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- QGPLUZHLBRLTMP-QGZVFWFLSA-N benzyl (2s)-2-(cyclohexylmethyl)-4-oxobutanoate Chemical compound C([C@@H](CC=O)C(=O)OCC=1C=CC=CC=1)C1CCCCC1 QGPLUZHLBRLTMP-QGZVFWFLSA-N 0.000 claims description 11
- GDZWTZDSOFTWKE-UHFFFAOYSA-N 2-(cyclohexylmethyl)butanoic acid Chemical compound CCC(C(O)=O)CC1CCCCC1 GDZWTZDSOFTWKE-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- -1 carbamoyl-1,1-diethyl-3-methoxy-1,2,3,4-tetrahydronaphthalen-2-ylamino Chemical group 0.000 claims description 7
- 229940125904 compound 1 Drugs 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000003085 diluting agent Substances 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
- 239000003937 drug carrier Substances 0.000 claims description 6
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- AMMHQMIASWQZNQ-YFNKSVMNSA-N (2s)-4-[[(2s,3s)-7-carbamoyl-1,1-diethyl-3-methoxy-3,4-dihydro-2h-naphthalen-2-yl]amino]-2-(cyclohexylmethyl)butanoic acid Chemical compound C([C@@H](CCN[C@H]1C(C2=CC(=CC=C2C[C@@H]1OC)C(N)=O)(CC)CC)C(O)=O)C1CCCCC1 AMMHQMIASWQZNQ-YFNKSVMNSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 206010054048 Postoperative ileus Diseases 0.000 claims description 4
- 230000001668 ameliorated effect Effects 0.000 claims description 4
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 4
- 230000004064 dysfunction Effects 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 230000000968 intestinal effect Effects 0.000 claims description 4
- 239000002623 mu opiate receptor antagonist Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229940005483 opioid analgesics Drugs 0.000 claims description 3
- ZABOFOZWCJGTEQ-UONOGXRCSA-N (6s,7s)-7-amino-8,8-diethyl-6-methoxy-6,7-dihydro-5h-naphthalene-2-carboxamide Chemical compound C1=C(C(N)=O)C=C2C(CC)(CC)[C@H](N)[C@@H](OC)CC2=C1 ZABOFOZWCJGTEQ-UONOGXRCSA-N 0.000 claims description 2
- YPJUUALGVIQOLR-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-2-carboxamide Chemical compound C1=CC=C2CC(C(=O)N)CCC2=C1 YPJUUALGVIQOLR-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 208000017228 Gastrointestinal motility disease Diseases 0.000 claims description 2
- 230000003042 antagnostic effect Effects 0.000 claims description 2
- NOVYHRPANXDTAC-WEAWZCMZSA-N benzyl (2s)-4-[[(2s,3s)-7-carbamoyl-1,1-diethyl-3-methoxy-3,4-dihydro-2h-naphthalen-2-yl]amino]-2-(cyclohexylmethyl)butanoate Chemical compound C([C@@H](CCN[C@H]1C(C2=CC(=CC=C2C[C@@H]1OC)C(N)=O)(CC)CC)C(=O)OCC=1C=CC=CC=1)C1CCCCC1 NOVYHRPANXDTAC-WEAWZCMZSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229940125782 compound 2 Drugs 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 102000051367 mu Opioid Receptors Human genes 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims description 2
- YLWLJWMLQFYIIT-KRNWZFANSA-M sodium;(1s)-3-(cyclohexylmethyl)-1-hydroxy-4-oxo-4-phenylmethoxybutane-1-sulfonate Chemical compound [Na+].C=1C=CC=CC=1COC(=O)C(C[C@@H](O)S([O-])(=O)=O)CC1CCCCC1 YLWLJWMLQFYIIT-KRNWZFANSA-M 0.000 claims description 2
- 108020001612 μ-opioid receptors Proteins 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 230000005176 gastrointestinal motility Effects 0.000 claims 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 claims 1
- 208000024891 symptom Diseases 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12125408P | 2008-12-10 | 2008-12-10 | |
| US61/121,254 | 2008-12-10 | ||
| PCT/US2009/067271 WO2010068649A1 (en) | 2008-12-10 | 2009-12-09 | Crystalline forms of a 3-carboxypropyl-aminotetralin compound |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012511580A JP2012511580A (ja) | 2012-05-24 |
| JP2012511580A5 true JP2012511580A5 (https=) | 2012-11-08 |
| JP5650657B2 JP5650657B2 (ja) | 2015-01-07 |
Family
ID=42122774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011540855A Expired - Fee Related JP5650657B2 (ja) | 2008-12-10 | 2009-12-09 | ３−カルボキシプロピル−アミノテトラリン化合物の結晶形態 |
Country Status (21)
| Country | Link |
|---|---|
| US (4) | US8101794B2 (https=) |
| EP (1) | EP2376427B1 (https=) |
| JP (1) | JP5650657B2 (https=) |
| KR (1) | KR101685187B1 (https=) |
| CN (1) | CN102245564B (https=) |
| AR (1) | AR074592A1 (https=) |
| AU (1) | AU2009324709B2 (https=) |
| BR (1) | BRPI0922920A2 (https=) |
| CA (1) | CA2745441C (https=) |
| CL (1) | CL2011001391A1 (https=) |
| CO (1) | CO6390054A2 (https=) |
| ES (1) | ES2645087T3 (https=) |
| IL (1) | IL213093A0 (https=) |
| MX (1) | MX2011006209A (https=) |
| MY (1) | MY179041A (https=) |
| NZ (1) | NZ593377A (https=) |
| RU (1) | RU2512390C2 (https=) |
| SG (1) | SG172016A1 (https=) |
| TW (1) | TWI449685B (https=) |
| WO (1) | WO2010068649A1 (https=) |
| ZA (1) | ZA201104319B (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2482107C2 (ru) | 2007-12-11 | 2013-05-20 | Тереванс, Инк. | Производные 3-карбоксипропил-аминотетралина и родственные соединения в качестве антагонистов mu-опиоидного рецептора |
| WO2009076399A2 (en) | 2007-12-11 | 2009-06-18 | Theravance, Inc. | Aminotetralin compounds as mu opioid receptor antagonists |
| AU2010295464B2 (en) * | 2009-09-18 | 2015-11-26 | Merck Sharp & Dohme Corp. | Use of opioid receptor antagonist for gastrointestinal tract disorders |
| US8658691B2 (en) * | 2011-09-30 | 2014-02-25 | Theravance, Inc. | Crystalline forms of a 3-[2-methanesulfonyl-1-(4-trifluoromethyl-phenoxy)ethyl]pyrrolidine compound |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6844368B1 (en) * | 1998-12-22 | 2005-01-18 | Edward Roberts | Compounds useful in pain management |
| US6498196B1 (en) * | 1998-12-22 | 2002-12-24 | Edward Roberts | Compounds useful in pain management |
| US6231594B1 (en) | 1999-08-11 | 2001-05-15 | Radiant Medical, Inc. | Method of controlling body temperature while reducing shivering |
| WO2003097586A1 (en) * | 2002-05-17 | 2003-11-27 | Janssen Pharmaceutica N.V. | Aminotetralin-derived urea modulators of vanilloid vr1 receptor |
| RU2005134364A (ru) * | 2003-04-08 | 2006-06-10 | Проджиникс Фармасьютикалз, Инк. (Us) | Комбинированное лечение запора |
| SE0301794D0 (sv) * | 2003-06-19 | 2003-06-19 | Astrazeneca Ab | New use III |
| JP2010509227A (ja) | 2006-11-07 | 2010-03-25 | ネクター セラピューティックス エイエル，コーポレイション | オピオイド作動薬およびオピオイド拮抗薬の用量形態および同時投与 |
| EP1997493A1 (en) * | 2007-05-28 | 2008-12-03 | Laboratorios del Dr. Esteve S.A. | Combination of a 5-HT7 receptor ligand and an opioid receptor ligand |
| RU2482107C2 (ru) * | 2007-12-11 | 2013-05-20 | Тереванс, Инк. | Производные 3-карбоксипропил-аминотетралина и родственные соединения в качестве антагонистов mu-опиоидного рецептора |
| WO2009076399A2 (en) | 2007-12-11 | 2009-06-18 | Theravance, Inc. | Aminotetralin compounds as mu opioid receptor antagonists |
| US8153686B2 (en) | 2008-04-01 | 2012-04-10 | Theravance, Inc. | Amino- and amido-aminotetralin derivatives and related compounds as mu opioid receptor antagonists |
-
2009
- 2009-12-09 JP JP2011540855A patent/JP5650657B2/ja not_active Expired - Fee Related
- 2009-12-09 SG SG2011041605A patent/SG172016A1/en unknown
- 2009-12-09 NZ NZ593377A patent/NZ593377A/xx not_active IP Right Cessation
- 2009-12-09 TW TW098142108A patent/TWI449685B/zh not_active IP Right Cessation
- 2009-12-09 WO PCT/US2009/067271 patent/WO2010068649A1/en not_active Ceased
- 2009-12-09 MX MX2011006209A patent/MX2011006209A/es active IP Right Grant
- 2009-12-09 KR KR1020117015637A patent/KR101685187B1/ko not_active Expired - Fee Related
- 2009-12-09 AU AU2009324709A patent/AU2009324709B2/en not_active Ceased
- 2009-12-09 BR BRPI0922920A patent/BRPI0922920A2/pt not_active IP Right Cessation
- 2009-12-09 MY MYPI2011002349A patent/MY179041A/en unknown
- 2009-12-09 EP EP09793383.2A patent/EP2376427B1/en not_active Not-in-force
- 2009-12-09 US US12/633,944 patent/US8101794B2/en not_active Expired - Fee Related
- 2009-12-09 RU RU2011128393/04A patent/RU2512390C2/ru active
- 2009-12-09 CA CA2745441A patent/CA2745441C/en active Active
- 2009-12-09 ES ES09793383.2T patent/ES2645087T3/es active Active
- 2009-12-09 CN CN200980149818.7A patent/CN102245564B/zh not_active Expired - Fee Related
- 2009-12-10 AR ARP090104803A patent/AR074592A1/es unknown
-
2011
- 2011-05-24 IL IL213093A patent/IL213093A0/en active IP Right Grant
- 2011-06-08 CO CO11070977A patent/CO6390054A2/es active IP Right Grant
- 2011-06-08 CL CL2011001391A patent/CL2011001391A1/es unknown
- 2011-06-09 ZA ZA2011/04319A patent/ZA201104319B/en unknown
- 2011-12-19 US US13/330,358 patent/US8324236B2/en not_active Expired - Fee Related
-
2012
- 2012-10-29 US US13/663,083 patent/US8486958B2/en not_active Expired - Fee Related
-
2013
- 2013-06-17 US US13/919,260 patent/US8969367B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI660956B (zh) | 調節蛋白質激酶之化合物的合成 | |
| CN100369894C (zh) | 氧化氮合酶抑制剂磷酸盐 | |
| JP5064024B2 (ja) | イマチニブの製造方法、及び該方法により製造されたイマチニブ | |
| CN104981458B (zh) | 组蛋白去甲基化酶抑制剂 | |
| JP4477097B2 (ja) | 中枢神経系障害の治療のための（２ｓ）−（４ｅ）−ｎ−メチル−５−［３−（５−イソプロポキシピリジン）イル］−４−ペンテン−２−アミンの多形形態 | |
| EP2970123A1 (en) | Salt of omecamtiv mecarbil and process for preparing salt | |
| JP2014521726A5 (https=) | ||
| CN1227233C (zh) | 纯晶形的5－氯－3－(4－甲磺酰基苯基)－6′－甲基－[2,3′]联吡啶及其合成方法 | |
| JP2011505356A5 (https=) | ||
| KR20240018528A (ko) | 신규의 염 및 결정 | |
| JP6644685B2 (ja) | ポマリドミドの調製およびその精製のための改善された方法 | |
| JP2012511580A5 (https=) | ||
| JP2008535848A5 (https=) | ||
| AU2022265730A1 (en) | Expanded dosage regimens for integrin inhibitors | |
| CN102232070A (zh) | (r)-5-((e)-2-(吡咯烷-3-基乙烯基)嘧啶的合成和新的盐形式 | |
| JP2011506463A5 (https=) | ||
| TW201718516A (zh) | 組蛋白去乙醯酶抑制劑之晶形 | |
| RU2011128393A (ru) | Кристаллические формы соединения 3-карбоксипропил-аминотетралина | |
| JP2013544271A5 (https=) | ||
| EP2516412A1 (en) | Processes for the purification of lubiprostone | |
| JP2008507578A (ja) | 塩酸イトプリド中間体としての４−［２−（ジメチルアミノ）エトキシ］ベンジルアミンを製造する方法 | |
| WO2014081047A1 (en) | Process for the preparation of (1s,4s,5s)-4-bromo-6-oxabicyclo[3.2.1] octan-7-one | |
| CA2582507A1 (en) | Compounds, compositions containing them, preparation thereof and uses thereof iii | |
| JP2008534537A5 (https=) | ||
| JP2006524208A5 (https=) |