JP2008518910A5 - - Google Patents
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- JP2008518910A5 JP2008518910A5 JP2007539018A JP2007539018A JP2008518910A5 JP 2008518910 A5 JP2008518910 A5 JP 2008518910A5 JP 2007539018 A JP2007539018 A JP 2007539018A JP 2007539018 A JP2007539018 A JP 2007539018A JP 2008518910 A5 JP2008518910 A5 JP 2008518910A5
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- JP
- Japan
- Prior art keywords
- compound
- formula
- alkyl
- aryl
- group
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000002252 acyl group Chemical group 0.000 claims description 34
- 229910052801 chlorine Inorganic materials 0.000 claims description 33
- 229910052731 fluorine Inorganic materials 0.000 claims description 31
- -1 phosphorus halides Chemical class 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 229940127240 opiate Drugs 0.000 claims 19
- 230000002194 synthesizing effect Effects 0.000 claims 15
- 239000003638 chemical reducing agent Substances 0.000 claims 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 239000002904 solvent Substances 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 8
- 229940124530 sulfonamide Drugs 0.000 claims 8
- 150000003456 sulfonamides Chemical class 0.000 claims 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 7
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 7
- 235000019253 formic acid Nutrition 0.000 claims 7
- 150000003461 sulfonyl halides Chemical class 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 150000004820 halides Chemical class 0.000 claims 5
- 238000007363 ring formation reaction Methods 0.000 claims 5
- 229910052741 iridium Inorganic materials 0.000 claims 4
- 229910052763 palladium Inorganic materials 0.000 claims 4
- 229910052698 phosphorus Inorganic materials 0.000 claims 4
- 239000011574 phosphorus Substances 0.000 claims 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 4
- 229910052707 ruthenium Inorganic materials 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 3
- 229910052697 platinum Inorganic materials 0.000 claims 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 3
- 150000003457 sulfones Chemical class 0.000 claims 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 150000002466 imines Chemical class 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- 0 *c(cc1O)c(CC(*CC2)C(CC3)C22CC3=O)c2c1O Chemical compound *c(cc1O)c(CC(*CC2)C(CC3)C22CC3=O)c2c1O 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- YNUJWPFONJZFTE-UHFFFAOYSA-N COc1cccc(CCNC(Cc(cc(c(O)c2)O)c2Cl)=O)c1 Chemical compound COc1cccc(CCNC(Cc(cc(c(O)c2)O)c2Cl)=O)c1 YNUJWPFONJZFTE-UHFFFAOYSA-N 0.000 description 1
- IMSQRCLWJIAQPA-UHFFFAOYSA-N Oc(c(O)c1)cc(CC2NCCC(C3)C2C=CC3=O)c1Cl Chemical compound Oc(c(O)c1)cc(CC2NCCC(C3)C2C=CC3=O)c1Cl IMSQRCLWJIAQPA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62539704P | 2004-11-04 | 2004-11-04 | |
| US60/625,397 | 2004-11-04 | ||
| PCT/US2005/038140 WO2006052430A2 (en) | 2004-11-04 | 2005-10-21 | Opiate intermediates and methods of synthesis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008518910A JP2008518910A (ja) | 2008-06-05 |
| JP2008518910A5 true JP2008518910A5 (enExample) | 2008-12-11 |
Family
ID=35695757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007539018A Withdrawn JP2008518910A (ja) | 2004-11-04 | 2005-10-21 | オピエート中間体および合成方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7834184B2 (enExample) |
| EP (1) | EP1812399B1 (enExample) |
| JP (1) | JP2008518910A (enExample) |
| CN (1) | CN101052622A (enExample) |
| AT (1) | ATE450513T1 (enExample) |
| AU (1) | AU2005305210B2 (enExample) |
| CA (1) | CA2585698A1 (enExample) |
| DE (1) | DE602005018092D1 (enExample) |
| ES (1) | ES2336131T3 (enExample) |
| MX (1) | MX2007005194A (enExample) |
| PL (1) | PL1812399T3 (enExample) |
| PT (1) | PT1812399E (enExample) |
| WO (1) | WO2006052430A2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2102163A2 (en) | 2006-12-12 | 2009-09-23 | Mallinckrodt Inc. | Preparation of hexahydroisoquinolines from dihydroisoquinolines |
| WO2011009020A2 (en) | 2009-07-16 | 2011-01-20 | Mallinckrodt Inc. | Compounds and compositions for use in phototherapy and in treatment of ocular neovascular disease and cancers |
| US8431705B2 (en) | 2009-09-24 | 2013-04-30 | Mallinckrodt Llc | One-pot preparation of hexahydroisoquinolines from amides |
| CN108383788A (zh) * | 2018-03-27 | 2018-08-10 | 合肥医工医药有限公司 | 一种二甲啡烷异构体的制备方法 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB685748A (en) | 1949-10-14 | 1953-01-07 | Hoffmann La Roche | Improvements in or relating to isoquinoline derivatives |
| DE1138765B (de) | 1954-12-28 | 1962-10-31 | Farmaceutici Italia | Verfahren zur Herstellung der Kaffeesaeureester der Chinasaeure |
| DE1154268B (de) | 1960-01-07 | 1963-09-12 | Bayer Ag | Die Verhuetung der elektrostatischen Aufladung bei synthetischen Hochpolymeren |
| US3438989A (en) | 1967-03-10 | 1969-04-15 | Warner Lambert Pharmaceutical | Process for the production of ( ) dihydrothebainone |
| US3862327A (en) | 1967-11-01 | 1975-01-21 | Uniroyal Inc | Substituted phenylethyl sulfites useful for controlling mites |
| FR2015566A1 (enExample) | 1968-08-13 | 1970-04-30 | Basf Ag | |
| US3922285A (en) | 1971-03-26 | 1975-11-25 | Hoffmann La Roche | Process for the methylenation of catechols |
| US3914233A (en) | 1972-10-20 | 1975-10-21 | Hoffmann La Roche | 4-Hydroxy-N-substituted morphinan derivatives |
| HU182087B (en) | 1980-01-15 | 1983-12-28 | Mta Kiserleti Orvostudomanyi K | Process for preparing an active substance for the selective inhibition of the multiplication of normal cells and of cells in myeloide leukemia |
| US4410700A (en) | 1980-07-03 | 1983-10-18 | The United States Of America As Represented By The Department Of Health And Human Services | Preparation of chiral 1-benzyl-1,2,3,4-tetrahydroisoquinolines by optical resolution |
| US4727146A (en) | 1980-07-03 | 1988-02-23 | The United States Of America As Represented By The Department Of Health And Human Services | Synthesis of chiral 1-benzyl-1,2,3,4-tetra-hydroisoquinolines by asymmetric reduction |
| US4368326A (en) * | 1980-07-03 | 1983-01-11 | Rice Kenner C | Short total synthesis of dihydrothebainone, dihydrocodeinone, and nordihydroccodeinone |
| US4521601A (en) | 1981-05-20 | 1985-06-04 | The United States Of America As Represented By The Department Of Health & Human Services | Practical total synthesis unnatural enantiomers of opium-derived morphinans |
| US4514569A (en) | 1982-01-28 | 1985-04-30 | Hendrickson James B | Synthesis of 1-substituted isoquinolines |
| US4452601A (en) | 1982-03-19 | 1984-06-05 | Celanese Corporation | Process for the thermal stabilization of acrylic fibers and films |
| US4613668A (en) * | 1983-12-22 | 1986-09-23 | The United States Of America As Represented By The Department Of Health And Human Services | Short total synthesis or morphinan compounds which uses cyclization of a cycloalkylcarbonyl compound selected from cyclopropylcarbonyl and cyclobutylcarbonyl |
| US4727504A (en) * | 1984-07-05 | 1988-02-23 | The Charles Stark Draper Laboratory, Inc. | Interference canceller and signal quantizer |
| US4737504A (en) | 1986-07-25 | 1988-04-12 | Ohio State University Research Foundation | 5-fluoro-and 8-fluoro-trimetoquinol compounds and the processes for their preparation |
| US5668285A (en) | 1986-10-31 | 1997-09-16 | The United States Of America As Represented By The Department Of Health And Human Services | Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates |
| US5023342A (en) | 1988-05-26 | 1991-06-11 | Massachusetts Institute Of Technology | Cyclic sulfate compounds |
| US5189200A (en) | 1990-12-21 | 1993-02-23 | Sepracor, Inc. | Process for the stereoselective transformation of a diol to an alcohol |
| GB9127306D0 (en) | 1991-12-23 | 1992-02-19 | Boots Co Plc | Therapeutic agents |
| JPH06247935A (ja) | 1993-02-25 | 1994-09-06 | Banyu Pharmaceut Co Ltd | ６，７−ジアルコキシ−３，４−ジヒドロイソキノリン−８−オール類、その製造法及び該化合物を用いた６，７−ジアルコキシ−１，２，３，４−テトラヒドロイソキノリン−８−オール類の製造法 |
| US5445164A (en) | 1993-05-11 | 1995-08-29 | Gynetech, Inc. | Cervical tissue sampling device |
| DE69410093T2 (de) | 1993-06-22 | 1998-10-01 | Knoll Ag | Isochinolin-derivate mit therapeutischer wirkung |
| US5869697A (en) | 1994-05-02 | 1999-02-09 | Council Of Scientific & Industrial Research | Process for preparing diltiazem |
| US6043253A (en) | 1998-03-03 | 2000-03-28 | Merck & Co., Inc. | Fused piperidine substituted arylsulfonamides as β3-agonists |
| KR100295740B1 (ko) | 1998-09-17 | 2001-11-05 | 박영구 | N-치환된-하이드록시고리화알킬아민유도체의제조방법 |
| DE60042585D1 (de) | 2000-02-29 | 2009-09-03 | Univ Firenze | 3-Aza-6,8-dioxabicycloÄ3.2.1Üoctane und Analoga sowie diese enthaltende kombinatorische Bibliotheken |
| US6593341B2 (en) | 2001-03-29 | 2003-07-15 | Molecular Design International, Inc. | β3-adrenoreceptor agonists, agonist compositions and methods of making and using the same |
| US6818766B2 (en) | 2002-10-02 | 2004-11-16 | Synthon Bv | Process for making bicalutamide and intermediates thereof |
| US6596734B1 (en) | 2002-10-11 | 2003-07-22 | Molecular Design International, Inc. | Tetrahydroisoquinoline compounds for use as β3-adrenoreceptor agonists |
-
2005
- 2005-10-21 PL PL05812329T patent/PL1812399T3/pl unknown
- 2005-10-21 AT AT05812329T patent/ATE450513T1/de active
- 2005-10-21 US US11/718,263 patent/US7834184B2/en active Active
- 2005-10-21 PT PT05812329T patent/PT1812399E/pt unknown
- 2005-10-21 JP JP2007539018A patent/JP2008518910A/ja not_active Withdrawn
- 2005-10-21 DE DE602005018092T patent/DE602005018092D1/de not_active Expired - Lifetime
- 2005-10-21 ES ES05812329T patent/ES2336131T3/es not_active Expired - Lifetime
- 2005-10-21 CA CA002585698A patent/CA2585698A1/en not_active Abandoned
- 2005-10-21 AU AU2005305210A patent/AU2005305210B2/en not_active Expired
- 2005-10-21 CN CNA2005800376856A patent/CN101052622A/zh active Pending
- 2005-10-21 EP EP05812329A patent/EP1812399B1/en not_active Expired - Lifetime
- 2005-10-21 WO PCT/US2005/038140 patent/WO2006052430A2/en not_active Ceased
- 2005-10-21 MX MX2007005194A patent/MX2007005194A/es active IP Right Grant
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