JP2006524247A - （＋）−ｐ−メンタ−２，８−ジエン−１−オールの製造方法 - Google Patents
（＋）−ｐ−メンタ−２，８−ジエン−１−オールの製造方法 Download PDFInfo
- Publication number
- JP2006524247A JP2006524247A JP2006510032A JP2006510032A JP2006524247A JP 2006524247 A JP2006524247 A JP 2006524247A JP 2006510032 A JP2006510032 A JP 2006510032A JP 2006510032 A JP2006510032 A JP 2006510032A JP 2006524247 A JP2006524247 A JP 2006524247A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl
- amine
- lewis acid
- oxide
- 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- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 49
- 239000002841 Lewis acid Substances 0.000 claims abstract description 23
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 23
- CCEFMUBVSUDRLG-XNWIYYODSA-N Limonene-1,2-epoxide Chemical compound C1[C@H](C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-XNWIYYODSA-N 0.000 claims abstract description 14
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 230000000707 stereoselective effect Effects 0.000 claims description 12
- -1 alkyl metal halides Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910001507 metal halide Inorganic materials 0.000 claims description 6
- 238000007142 ring opening reaction Methods 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
- 150000004820 halides Chemical group 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229940087305 limonene Drugs 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000011236 particulate material Substances 0.000 claims description 3
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- 150000005215 alkyl ethers Chemical class 0.000 claims 5
- CCEFMUBVSUDRLG-KXUCPTDWSA-N D-limonene 1,2-Epoxide Chemical compound C1[C@H](C(=C)C)CC[C@@]2(C)O[C@H]21 CCEFMUBVSUDRLG-KXUCPTDWSA-N 0.000 claims 2
- 150000002118 epoxides Chemical group 0.000 claims 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 2
- 125000000815 N-oxide group Chemical group 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 150000002924 oxiranes Chemical group 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 6
- YTJVBLPAMBTDCH-RDBSUJKOSA-N (1s,2s,4r)-1-methyl-2-morpholin-4-yl-4-prop-1-en-2-ylcyclohexan-1-ol Chemical compound C1[C@H](C(=C)C)CC[C@](C)(O)[C@H]1N1CCOCC1 YTJVBLPAMBTDCH-RDBSUJKOSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 4
- 229910013594 LiOAc Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 229960004242 dronabinol Drugs 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 235000001510 limonene Nutrition 0.000 description 3
- 238000000197 pyrolysis Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical group [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical group [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CCEFMUBVSUDRLG-BBBLOLIVSA-N (+)-trans-limonene oxide Chemical compound C1[C@H](C(=C)C)CC[C@]2(C)O[C@@H]21 CCEFMUBVSUDRLG-BBBLOLIVSA-N 0.000 description 1
- FIBYEHQMESYELP-UJMBWUOASA-N (1S,2S,4R)-1-methyl-2-piperidin-1-yl-4-prop-1-en-2-ylcyclohexan-1-ol Chemical compound N1(CCCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C.N1(CCCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C FIBYEHQMESYELP-UJMBWUOASA-N 0.000 description 1
- 229930007447 (4R)-limonene 1alpha,2alpha-epoxide Natural products 0.000 description 1
- 238000006728 Cope elimination reaction Methods 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- NLEIDZBFXWJTHY-DAVHSNPESA-N N1(CCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C.N1(CCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C Chemical compound N1(CCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C.N1(CCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C NLEIDZBFXWJTHY-DAVHSNPESA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 240000004308 marijuana Species 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical group O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46504603P | 2003-04-24 | 2003-04-24 | |
| PCT/US2004/011509 WO2004096740A2 (en) | 2003-04-24 | 2004-04-14 | Process for preparation of (+)-p-mentha-2,8-diene-1-ol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006524247A true JP2006524247A (ja) | 2006-10-26 |
| JP2006524247A5 JP2006524247A5 (enExample) | 2007-05-17 |
Family
ID=33418173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006510032A Withdrawn JP2006524247A (ja) | 2003-04-24 | 2004-04-14 | （＋）−ｐ−メンタ−２，８−ジエン−１−オールの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7323607B2 (enExample) |
| EP (1) | EP1660421A2 (enExample) |
| JP (1) | JP2006524247A (enExample) |
| CN (1) | CN1777569A (enExample) |
| AU (1) | AU2004234350A1 (enExample) |
| CA (1) | CA2523419C (enExample) |
| MX (1) | MXPA05011292A (enExample) |
| WO (1) | WO2004096740A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023038912A (ja) * | 2021-09-07 | 2023-03-17 | 旭富製藥科技股▲分▼有限公司 | テルペノイドアミノアルコール誘導体を精製するための方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009536623A (ja) | 2006-04-24 | 2009-10-15 | アラーガン、インコーポレイテッド | 眼圧降下剤としてのアブノーマル・カンナビジオール化合物 |
| CN112661656B (zh) * | 2020-12-19 | 2022-05-20 | 浙江新和成股份有限公司 | (1s,4r)-1-甲基-4-(1-甲基乙烯基)-2-环己烯-1-醇的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3538164A (en) * | 1968-02-08 | 1970-11-03 | Reynolds Tobacco Co R | Synthesis of dihydrocarvone |
| US3814733A (en) * | 1970-07-27 | 1974-06-04 | Smc Corp | Isomerization of(+)-trans-2,3-epoxy-ciscarane to(+)-cis-2,8-p-methadiene-1-ol |
| US3734930A (en) * | 1971-09-22 | 1973-05-22 | R Razdan | Direct synthesis of ({31 )-trans-{66 {11 tetrahydrocannabinol from olivetol and ({30 )-trans-{66 {11 -carene oxide |
| US4025516A (en) * | 1975-06-23 | 1977-05-24 | The John C. Sheehan Institute For Research, Inc. | Process for the preparation of (-)-6a,10a-trans-6a,7,8,10a-tetrahydrodibenzo[b,d]-pyrans |
| IL48824A (en) * | 1976-01-12 | 1980-05-30 | Yissum Res Dev Co | Pharmaceutical compositions containing (3s,js) tetrahydrocanabinol derivatives and some novel compounds of this type |
| US4296257A (en) * | 1980-01-07 | 1981-10-20 | Scm Corporation | Process for producing dihydrocarvone geometric isomers |
| CH646933A5 (fr) * | 1981-05-04 | 1984-12-28 | Firmenich & Cie | Procede pour la preparation de (+)-p-mentha-2,8-diene-1-ol. |
| US6262278B1 (en) * | 1995-03-14 | 2001-07-17 | President And Fellows Of Harvard College | Stereoselective ring opening reactions |
| US5777137A (en) * | 1995-11-01 | 1998-07-07 | University Of Florida | Pancratistatins and processes for their production |
-
2004
- 2004-04-14 CA CA2523419A patent/CA2523419C/en not_active Expired - Fee Related
- 2004-04-14 AU AU2004234350A patent/AU2004234350A1/en not_active Abandoned
- 2004-04-14 EP EP04760258A patent/EP1660421A2/en not_active Withdrawn
- 2004-04-14 CN CNA2004800109761A patent/CN1777569A/zh active Pending
- 2004-04-14 US US10/549,976 patent/US7323607B2/en not_active Expired - Lifetime
- 2004-04-14 MX MXPA05011292A patent/MXPA05011292A/es active IP Right Grant
- 2004-04-14 WO PCT/US2004/011509 patent/WO2004096740A2/en not_active Ceased
- 2004-04-14 JP JP2006510032A patent/JP2006524247A/ja not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023038912A (ja) * | 2021-09-07 | 2023-03-17 | 旭富製藥科技股▲分▼有限公司 | テルペノイドアミノアルコール誘導体を精製するための方法 |
| JP7367147B2 (ja) | 2021-09-07 | 2023-10-23 | 旭富製藥科技股▲分▼有限公司 | テルペノイドアミノアルコール誘導体を精製するための方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2523419C (en) | 2012-05-01 |
| CN1777569A (zh) | 2006-05-24 |
| CA2523419A1 (en) | 2004-11-11 |
| US7323607B2 (en) | 2008-01-29 |
| WO2004096740A2 (en) | 2004-11-11 |
| EP1660421A2 (en) | 2006-05-31 |
| MXPA05011292A (es) | 2006-01-24 |
| US20060084828A1 (en) | 2006-04-20 |
| WO2004096740A3 (en) | 2005-06-02 |
| AU2004234350A1 (en) | 2004-11-11 |
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