JP2005506985A5 - - Google Patents
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- Publication number
- JP2005506985A5 JP2005506985A5 JP2003528819A JP2003528819A JP2005506985A5 JP 2005506985 A5 JP2005506985 A5 JP 2005506985A5 JP 2003528819 A JP2003528819 A JP 2003528819A JP 2003528819 A JP2003528819 A JP 2003528819A JP 2005506985 A5 JP2005506985 A5 JP 2005506985A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pharmaceutically acceptable
- formula
- acceptable salt
- toxic pharmaceutically
- 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
- 150000001875 compounds Chemical class 0.000 claims description 33
- ZKLXUUYLEHCAMF-UUWFMWQGSA-N Oripavine Chemical class C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 ZKLXUUYLEHCAMF-UUWFMWQGSA-N 0.000 claims description 11
- 231100000252 nontoxic Toxicity 0.000 claims description 10
- 230000003000 nontoxic effect Effects 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 230000000202 analgesic effect Effects 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000000729 antidote Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000026251 Opioid-Related disease Diseases 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 201000005040 opiate dependence Diseases 0.000 claims 1
- RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 description 9
- 229960001736 buprenorphine Drugs 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 206010052804 Drug tolerance Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000026781 habituation Effects 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 0 C[C@@](C1)(C2CC1(C(C1)*(*)CC3)C3(C3O)c4c1ccc(O)c4C)C23C(*)=O Chemical compound C[C@@](C1)(C2CC1(C(C1)*(*)CC3)C3(C3O)c4c1ccc(O)c4C)C23C(*)=O 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 241000282560 Macaca mulatta Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QJWZMTFDVIYWPI-UHFFFAOYSA-M [Br-].[Mg+]CCC1=CC=CS1 Chemical compound [Br-].[Mg+]CCC1=CC=CS1 QJWZMTFDVIYWPI-UHFFFAOYSA-M 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000003502 anti-nociceptive effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- -1 bromide compound Chemical class 0.000 description 1
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 229940051808 oripavine derivative analgesics Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 208000037974 severe injury Diseases 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229930003945 thebaine Natural products 0.000 description 1
- FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011421495A CN1233645C (zh) | 2001-09-14 | 2001-09-14 | 新的东罂粟碱衍生物及其医药用途 |
| PCT/CN2002/000642 WO2003024972A1 (en) | 2001-09-14 | 2002-09-13 | New oripavine derivatives and their uses as medicines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005506985A JP2005506985A (ja) | 2005-03-10 |
| JP2005506985A5 true JP2005506985A5 (enExample) | 2009-10-01 |
| JP4532109B2 JP4532109B2 (ja) | 2010-08-25 |
Family
ID=4676657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003528819A Expired - Lifetime JP4532109B2 (ja) | 2001-09-14 | 2002-09-13 | 新規オリパビン誘導体および医薬としてのその使用 |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1439179B1 (enExample) |
| JP (1) | JP4532109B2 (enExample) |
| CN (1) | CN1233645C (enExample) |
| AT (1) | ATE390428T1 (enExample) |
| DE (1) | DE60225827D1 (enExample) |
| MX (1) | MXPA04002422A (enExample) |
| WO (1) | WO2003024972A1 (enExample) |
| ZA (1) | ZA200402733B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1939920B (zh) * | 2005-09-29 | 2011-08-31 | 中国人民解放军军事医学科学院毒物药物研究所 | 东罂粟碱类化合物及其医药用途 |
| ES2329296T3 (es) * | 2006-01-05 | 2009-11-24 | Mallinckrodt, Inc. | El uso de oripavina como material de partida para buprenorfina. |
| CA2674915C (en) | 2006-10-17 | 2015-06-30 | Penick Corporation | Process for preparing oxymorphone |
| US20080125592A1 (en) | 2006-10-17 | 2008-05-29 | Penick Corporation | Process for preparing oxymorphone, naltrexone, and buprenorphine |
| US8546572B2 (en) * | 2008-03-31 | 2013-10-01 | Sun Pharmaceutical Industries Limited | Process for the preparation of morphinane analogues |
| AU2009300390B2 (en) * | 2008-09-30 | 2015-05-14 | SpecGx LLC | Processes for the production of buprenorphine with reduced impurity formation |
| ES2462756T3 (es) | 2008-09-30 | 2014-05-26 | Mallinckrodt Llc | Procedimientos de síntesis de alcaloides opiáceos con formación reducida de impurezas |
| NZ592005A (en) | 2008-09-30 | 2013-03-28 | Mallinckrodt Llc | Process for the preparation of a N-alkylated ketomorphinan by selective catalytiC hydrogen transfer reduction |
| ES2477190T3 (es) | 2008-09-30 | 2014-07-16 | Mallinckrodt Llc | Procedimiento de reciclaje para aumentar el rendimiento de una reacción de Grignard en la preparación de derivados alcaloides opiáceos |
| CA2738089C (en) | 2008-09-30 | 2017-07-18 | Mallinckrodt Inc. | Processes for the hydrogenation of opiate alkaloid derivatives |
| EP2342207B1 (en) | 2008-09-30 | 2015-11-11 | Mallinckrodt LLC | Processes for the alkylation of norbuprenorphine with reduced impurity formation |
| TWI630208B (zh) * | 2008-12-08 | 2018-07-21 | 歐陸斯迪公司 | 二氫羥戊甲嗎啡 |
| CN102462680B (zh) * | 2010-11-04 | 2016-08-03 | 中国人民解放军军事医学科学院毒物药物研究所 | 噻吩诺啡的长效缓释微球及其组合物和制备方法 |
| CN102382118A (zh) * | 2011-05-23 | 2012-03-21 | 浙江仙琚制药股份有限公司 | 一种7ɑ-乙酰基-6,14-乙基桥四氢蒂巴因的制备方法 |
| GB201309654D0 (en) | 2013-05-30 | 2013-07-17 | Euro Celtique Sa | Method |
| EP3023427A1 (en) | 2014-11-19 | 2016-05-25 | Siegfried AG | Improved method of manufacturing buprenorphine and analogues thereof from oripavine |
| EP3067357A1 (en) | 2015-03-11 | 2016-09-14 | Siegfried AG | Method of manufacturing stereoisomers of buprenorphine and analogues thereof |
| GB2550566A (en) | 2016-05-19 | 2017-11-29 | Chapelglade Ltd | Mattress evaluation system and method |
| CN108530452B (zh) * | 2017-03-01 | 2023-02-03 | 泰州华元医药科技有限公司 | 高效抗成瘾药物 |
| EP4613751A1 (en) | 2024-03-07 | 2025-09-10 | Siegfried AG | Method of making chemical compounds useful for the synthesis of buprenorphine |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB925723A (en) * | 1960-09-05 | 1963-05-08 | J F Macfarlan & Company Ltd | Novel thebaine derivatives |
| US3474101A (en) * | 1960-09-05 | 1969-10-21 | Reckitt & Sons Ltd | Thebaine and oripavine derivatives |
| DE2230154A1 (de) * | 1972-06-21 | 1974-01-17 | Boehringer Sohn Ingelheim | N-(heteroaryl-methyl)-6,14-endoaetheno7alpha-hydroxyalkyl-tetrahydro-nororipavine und -thebaine, deren hydrierungsprodukte und saeureadditionssalze sowie verfahren zu deren herstellung |
| KR100204659B1 (ko) * | 1996-05-28 | 1999-06-15 | 강재헌 | 신규한 부프레노핀계 진통제용 화합물 |
-
2001
- 2001-09-14 CN CNB011421495A patent/CN1233645C/zh not_active Expired - Lifetime
-
2002
- 2002-09-13 AT AT02764501T patent/ATE390428T1/de not_active IP Right Cessation
- 2002-09-13 DE DE60225827T patent/DE60225827D1/de not_active Expired - Lifetime
- 2002-09-13 EP EP02764501A patent/EP1439179B1/en not_active Expired - Lifetime
- 2002-09-13 WO PCT/CN2002/000642 patent/WO2003024972A1/zh not_active Ceased
- 2002-09-13 MX MXPA04002422A patent/MXPA04002422A/es active IP Right Grant
- 2002-09-13 JP JP2003528819A patent/JP4532109B2/ja not_active Expired - Lifetime
-
2004
- 2004-04-07 ZA ZA2004/02733A patent/ZA200402733B/en unknown
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