OA12002A - Process for the preparation of isotretinoin. - Google Patents
Process for the preparation of isotretinoin. Download PDFInfo
- Publication number
- OA12002A OA12002A OA1200200035A OA1200200035A OA12002A OA 12002 A OA12002 A OA 12002A OA 1200200035 A OA1200200035 A OA 1200200035A OA 1200200035 A OA1200200035 A OA 1200200035A OA 12002 A OA12002 A OA 12002A
- Authority
- OA
- OAPI
- Prior art keywords
- isotretinoin
- formula
- daim
- solvent
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 229960005280 isotretinoin Drugs 0.000 title claims abstract description 22
- SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 title claims abstract 5
- 238000002360 preparation method Methods 0.000 title abstract description 3
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims abstract description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 6
- 229960001727 tretinoin Drugs 0.000 claims description 6
- 238000010626 work up procedure Methods 0.000 claims description 6
- OPSSCPNCFKJCFR-ANKZSMJWSA-N (2e,4e)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)penta-2,4-dienal Chemical compound O=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OPSSCPNCFKJCFR-ANKZSMJWSA-N 0.000 claims description 5
- JHLHKCWPDVKWNS-UHFFFAOYSA-N 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid Chemical compound CC1=NOC(C=2C(=CC=CC=2)C(O)=O)=N1 JHLHKCWPDVKWNS-UHFFFAOYSA-N 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 239000012535 impurity Substances 0.000 claims description 3
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 4
- 229960000443 hydrochloric acid Drugs 0.000 claims 1
- 235000011167 hydrochloric acid Nutrition 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 229930002330 retinoic acid Natural products 0.000 abstract description 3
- SHGAZHPCJJPHSC-XFYACQKRSA-N isotretinoin Chemical compound OC(=O)/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-XFYACQKRSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229940032330 sulfuric acid Drugs 0.000 description 3
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000007699 photoisomerization reaction Methods 0.000 description 2
- JBYXPOFIGCOSSB-UQGDGPGGSA-N rumenic acid Chemical compound CCCCCC\C=C/C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-UQGDGPGGSA-N 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- SHGAZHPCJJPHSC-SMMNRBFNSA-N (2z,4z,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid Chemical compound OC(=O)\C=C(\C)/C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-SMMNRBFNSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- XRNPHZPFAWLRNJ-UHFFFAOYSA-N 2-hydroxy-3-methyl-2h-furan-5-one Chemical compound CC1=CC(=O)OC1O XRNPHZPFAWLRNJ-UHFFFAOYSA-N 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 description 1
- SHGAZHPCJJPHSC-CDMOMSTLSA-N 9,13-cis-Retinoic acid Chemical compound OC(=O)\C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-CDMOMSTLSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 150000004347 all-trans-retinol derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000012777 commercial manufacturing Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- -1 phosphonate ester Chemical class 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- 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)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1037DE1999 IN190846B (pt) | 1999-07-30 | 1999-07-30 | |
| US09/467,201 US6441226B1 (en) | 1999-07-30 | 1999-12-20 | Process for the preparation of isotretinoin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA12002A true OA12002A (en) | 2006-04-18 |
Family
ID=26324696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200200035A OA12002A (en) | 1999-07-30 | 2000-07-24 | Process for the preparation of isotretinoin. |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1204637B1 (pt) |
| JP (1) | JP2003506349A (pt) |
| CN (1) | CN1167679C (pt) |
| AP (1) | AP2002002414A0 (pt) |
| AT (1) | ATE293596T1 (pt) |
| AU (1) | AU778584B2 (pt) |
| BG (1) | BG106369A (pt) |
| BR (1) | BR0012866A (pt) |
| CA (1) | CA2380026A1 (pt) |
| DE (1) | DE60019611T2 (pt) |
| EA (1) | EA004651B1 (pt) |
| EE (1) | EE200200053A (pt) |
| ES (1) | ES2240117T3 (pt) |
| HK (1) | HK1046901B (pt) |
| HR (1) | HRP20020098A2 (pt) |
| HU (1) | HUP0202230A3 (pt) |
| IL (1) | IL147918A0 (pt) |
| MX (1) | MXPA02001107A (pt) |
| OA (1) | OA12002A (pt) |
| PL (1) | PL353491A1 (pt) |
| PT (1) | PT1204637E (pt) |
| SK (1) | SK1612002A3 (pt) |
| TR (1) | TR200200455T2 (pt) |
| WO (1) | WO2001009089A1 (pt) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447459A (zh) * | 2014-11-28 | 2015-03-25 | 重庆华邦制药有限公司 | 异维a酸的新晶型及其制备方法与应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2951853A (en) * | 1957-06-08 | 1960-09-06 | Sumitomo Chemical Co | Method for preparing polyenecarboxylic acid derivatives |
-
2000
- 2000-07-24 IL IL14791800A patent/IL147918A0/xx not_active IP Right Cessation
- 2000-07-24 DE DE60019611T patent/DE60019611T2/de not_active Expired - Fee Related
- 2000-07-24 OA OA1200200035A patent/OA12002A/en unknown
- 2000-07-24 ES ES00944156T patent/ES2240117T3/es not_active Expired - Lifetime
- 2000-07-24 WO PCT/IB2000/001020 patent/WO2001009089A1/en not_active Ceased
- 2000-07-24 MX MXPA02001107A patent/MXPA02001107A/es active IP Right Grant
- 2000-07-24 SK SK161-2002A patent/SK1612002A3/sk unknown
- 2000-07-24 CN CNB008119988A patent/CN1167679C/zh not_active Expired - Fee Related
- 2000-07-24 PT PT00944156T patent/PT1204637E/pt unknown
- 2000-07-24 AT AT00944156T patent/ATE293596T1/de not_active IP Right Cessation
- 2000-07-24 EA EA200200110A patent/EA004651B1/ru not_active IP Right Cessation
- 2000-07-24 CA CA002380026A patent/CA2380026A1/en not_active Abandoned
- 2000-07-24 AU AU58388/00A patent/AU778584B2/en not_active Ceased
- 2000-07-24 JP JP2001514293A patent/JP2003506349A/ja active Pending
- 2000-07-24 BR BR0012866-0A patent/BR0012866A/pt not_active IP Right Cessation
- 2000-07-24 EP EP00944156A patent/EP1204637B1/en not_active Expired - Lifetime
- 2000-07-24 HK HK02108127.7A patent/HK1046901B/en not_active IP Right Cessation
- 2000-07-24 PL PL00353491A patent/PL353491A1/xx not_active Application Discontinuation
- 2000-07-24 EE EEP200200053A patent/EE200200053A/xx unknown
- 2000-07-24 HU HU0202230A patent/HUP0202230A3/hu unknown
- 2000-07-24 HR HR20020098A patent/HRP20020098A2/xx not_active Application Discontinuation
- 2000-07-24 AP APAP/P/2002/002414A patent/AP2002002414A0/en unknown
- 2000-07-24 TR TR2002/00455T patent/TR200200455T2/xx unknown
-
2002
- 2002-01-30 BG BG106369A patent/BG106369A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR0012866A (pt) | 2002-07-09 |
| HRP20020098A2 (en) | 2003-12-31 |
| CA2380026A1 (en) | 2001-02-08 |
| MXPA02001107A (es) | 2002-08-20 |
| SK1612002A3 (en) | 2002-06-04 |
| HUP0202230A2 (hu) | 2002-11-28 |
| HK1046901B (en) | 2005-09-23 |
| DE60019611T2 (de) | 2006-03-02 |
| WO2001009089A1 (en) | 2001-02-08 |
| AU5838800A (en) | 2001-02-19 |
| EP1204637A1 (en) | 2002-05-15 |
| PT1204637E (pt) | 2005-08-31 |
| EE200200053A (et) | 2003-04-15 |
| EP1204637B1 (en) | 2005-04-20 |
| BG106369A (bg) | 2002-08-30 |
| ATE293596T1 (de) | 2005-05-15 |
| CN1371362A (zh) | 2002-09-25 |
| HUP0202230A3 (en) | 2004-03-01 |
| ES2240117T3 (es) | 2005-10-16 |
| CN1167679C (zh) | 2004-09-22 |
| HK1046901A1 (en) | 2003-01-30 |
| PL353491A1 (en) | 2003-11-17 |
| EA004651B1 (ru) | 2004-06-24 |
| AU778584B2 (en) | 2004-12-09 |
| DE60019611D1 (de) | 2005-05-25 |
| AP2002002414A0 (en) | 2002-03-31 |
| TR200200455T2 (tr) | 2002-07-22 |
| JP2003506349A (ja) | 2003-02-18 |
| IL147918A0 (en) | 2002-08-14 |
| EA200200110A1 (ru) | 2002-08-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK175169B1 (da) | Carotenoid-mellemprodukter, fremgangsmåde til fremstilling deraf samt brug af mellemprodukterne i fremstillingen af carotenoider | |
| EP1328506B1 (fr) | Intermediaires utiles pour la synthese de retinoides | |
| US4946841A (en) | Pyridazine 3,5-dihydroxy carboxylic acids and derivatives thereof, the use thereof for hypercholesterolemia | |
| Gilbert et al. | Enantioselective synthesis of (-)-trichodiene | |
| US7067703B2 (en) | Manufacture of retinoids | |
| OA12002A (en) | Process for the preparation of isotretinoin. | |
| Bezzenine-Lafollée et al. | SmI2-Mediated 3-exo-trig cyclisation of δ-oxo-α, β-unsaturated esters to cyclopropanols and derivatives | |
| US6441226B1 (en) | Process for the preparation of isotretinoin | |
| Yamamoto et al. | Chemistry of cyclic phosphorus compounds. 3. Synthesis of pheromones having an. gamma.,. delta.-unsaturated ketone system from 1, 1-diphenylphospholanium perchlorate | |
| EP0959069B1 (en) | A process for the preparation of 13-CIS-retinoic acid | |
| AU725484B2 (en) | Compounds and method for preparing substituted 4-phenyl-4-cyanocyclohexanoic acids | |
| Lansbury et al. | Total synthesis of pseudoguaianes—I: Preparation of bicyclo [5.3. 0] decane synthons for damsinic acid and helenanolides | |
| HU199768B (en) | Process for production of 3,5-dihydroxi-carbonic acid and its derivatives and medical compositions containing them | |
| TW201141825A (en) | New process for isomerizing fused bicyclic structures and preparation of vitamin D analogs comprising the same | |
| Pratt et al. | Synthesis of (.+-.)-4-De (3-hydroxypropionyl) betaenone B, an advanced model for the betaenones and stamphyloxin I | |
| CZ2002370A3 (cs) | Způsob přípravy izotretinoinu | |
| Park et al. | Effect of C-9 Substituents on the Regioselectivity of A-Ring Reactions in Derivatives of the Wieland-Miescher Ketone | |
| Tanimori et al. | Efficient chemical conversion of (±)-chokol G to (±)-chokols A, B, C, F, and K, chokolic acid B, and chokolal A | |
| Davalian et al. | Synthesis of 7, 8-epoxy-7, 8-dihydroretinoids | |
| Ahn et al. | Reaction of Allylmanganese (II) Reagents with Aldehydes | |
| SU767083A1 (ru) | Способ получени 1,2,5,5,9-пентаметил3-кето- -октагидронафталена | |
| Childress | I. Photoinduced nucleophilic addition to s-cis naphthalenones | |
| TAUB | The Total Synthesis | |
| MXPA96004879A (en) | Methods for the synthesis of retinoids 9-cis and its intermediaries novedo | |
| McCleary | Synthetic and Structural Studies on the Novel Formation of Bicyclo [n. 2.0] alkan-1-ols |