JP2012511580A5 - - Google Patents
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- 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 |
|---|---|---|---|---|
| WO2009076399A2 (en) | 2007-12-11 | 2009-06-18 | Theravance, Inc. | Aminotetralin compounds as mu opioid receptor antagonists |
| ES2402749T3 (es) | 2007-12-11 | 2013-05-08 | Theravance, Inc. | Derivados de 3-carboxipropil-aminotetralina como antagonistas del receptor de opioide mu |
| CA2774021A1 (en) * | 2009-09-18 | 2011-03-24 | Adolor Corporation | Use of opioid receptor antagonist for gastrointestinal tract disorders |
| CN103814010A (zh) * | 2011-09-30 | 2014-05-21 | 施万制药 | 3-[2-甲磺酰基-1-(4-三氟甲基苯氧基)乙基]吡咯烷化合物的结晶形式 |
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 |
| EP1638607A1 (en) * | 2003-04-08 | 2006-03-29 | Progenics Pharmaceuticals, Inc. | Combination therapy for constipation comprising a laxative and a peripheral opioid antagonist |
| SE0301794D0 (sv) * | 2003-06-19 | 2003-06-19 | Astrazeneca Ab | New use III |
| AU2007317788B2 (en) | 2006-11-07 | 2013-05-02 | Nektar Therapeutics | Dosage forms and co-administration of an opioid agonist and an opioid antagonist |
| 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 |
| WO2009076399A2 (en) | 2007-12-11 | 2009-06-18 | Theravance, Inc. | Aminotetralin compounds as mu opioid receptor antagonists |
| ES2402749T3 (es) | 2007-12-11 | 2013-05-08 | Theravance, Inc. | Derivados de 3-carboxipropil-aminotetralina como antagonistas del receptor de opioide mu |
| WO2009124022A1 (en) | 2008-04-01 | 2009-10-08 | Theravance, Inc. | 2 -aminotetralin derivatives as mu opioid receptor antagonists |
-
2009
- 2009-12-09 TW TW098142108A patent/TWI449685B/zh not_active IP Right Cessation
- 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 MY MYPI2011002349A patent/MY179041A/en unknown
- 2009-12-09 CN CN200980149818.7A patent/CN102245564B/zh not_active Expired - Fee Related
- 2009-12-09 MX MX2011006209A patent/MX2011006209A/es active IP Right Grant
- 2009-12-09 EP EP09793383.2A patent/EP2376427B1/en not_active Not-in-force
- 2009-12-09 JP JP2011540855A patent/JP5650657B2/ja not_active Expired - Fee Related
- 2009-12-09 CA CA2745441A patent/CA2745441C/en active Active
- 2009-12-09 RU RU2011128393/04A patent/RU2512390C2/ru active
- 2009-12-09 SG SG2011041605A patent/SG172016A1/en unknown
- 2009-12-09 ES ES09793383.2T patent/ES2645087T3/es active Active
- 2009-12-09 US US12/633,944 patent/US8101794B2/en not_active Expired - Fee Related
- 2009-12-09 WO PCT/US2009/067271 patent/WO2010068649A1/en not_active Ceased
- 2009-12-09 NZ NZ593377A patent/NZ593377A/xx not_active IP Right Cessation
- 2009-12-09 BR BRPI0922920A patent/BRPI0922920A2/pt not_active IP Right Cessation
- 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 CL CL2011001391A patent/CL2011001391A1/es unknown
- 2011-06-08 CO CO11070977A patent/CO6390054A2/es active IP Right Grant
- 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
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