BG106369A - Метод за получаване на изотретиноин - Google Patents

Метод за получаване на изотретиноин Download PDF

Info

Publication number: BG106369A
Authority: BG; Bulgaria
Prior art keywords: acid; isotretinoin; formula; solvent; water
Prior art date: 1999-07-30

Application number

BG106369A

Other languages

Bulgarian (bg)

English (en)

Inventor

Mohammad Salman

Kaul Vijay Kumar

J. Babu

Naresh Kumar

Original Assignee

Ranbaxy Laboratories Limited

Priority date (The priority date 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 date listed.)

1999-07-30

Filing date

2002-01-30

Publication date

2002-08-30

1999-07-30 Priority claimed from IN1037DE1999 external-priority patent/IN190846B/en

2002-01-30 Application filed by Ranbaxy Laboratories Limited filed Critical Ranbaxy Laboratories Limited

2002-08-30 Publication of BG106369A publication Critical patent/BG106369A/bg

Links

238000000034 method Methods 0.000 title claims abstract description 29
229960005280 isotretinoin Drugs 0.000 title claims abstract description 25
238000002360 preparation method Methods 0.000 title claims abstract description 8
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
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 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
229960001727 tretinoin Drugs 0.000 claims description 7
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 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
238000011161 development Methods 0.000 claims description 6
150000002596 lactones Chemical class 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
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
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
239000011260 aqueous acid Substances 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 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 9
PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 8
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
-1 polyethylene side chain Polymers 0.000 description 5
SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
238000013459 approach Methods 0.000 description 4
238000007699 photoisomerization reaction Methods 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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 3
239000003054 catalyst Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
230000018109 developmental process Effects 0.000 description 3
230000000707 stereoselective effect Effects 0.000 description 3
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 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
208000002874 Acne Vulgaris Diseases 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
206010000496 acne Diseases 0.000 description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
150000001261 hydroxy acids Chemical class 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 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
239000012299 nitrogen atmosphere Substances 0.000 description 2
150000004291 polyenes Polymers 0.000 description 2
JBYXPOFIGCOSSB-UQGDGPGGSA-N rumenic acid Chemical class CCCCCC\C=C/C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-UQGDGPGGSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229910052723 transition metal Inorganic materials 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
XRNPHZPFAWLRNJ-UHFFFAOYSA-N 2-hydroxy-3-methyl-2h-furan-5-one Chemical compound CC1=CC(=O)OC1O XRNPHZPFAWLRNJ-UHFFFAOYSA-N 0.000 description 1
OALHHIHQOFIMEF-UHFFFAOYSA-N 3',6'-dihydroxy-2',4',5',7'-tetraiodo-3h-spiro[2-benzofuran-1,9'-xanthene]-3-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 OALHHIHQOFIMEF-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
FBMORZZOJSDNRQ-UHFFFAOYSA-N Demethoxy,B,HCl-Adriamycin Natural products C1C2C(=C)CCCC2(C)CC2(O)C1=C(C)C(=O)O2 FBMORZZOJSDNRQ-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 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
230000001154 acute effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
210000000589 cicatrix Anatomy 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
JUTMAMXOAOYKHT-UHFFFAOYSA-N karrikinolide Natural products C1=COC=C2OC(=O)C(C)=C21 JUTMAMXOAOYKHT-UHFFFAOYSA-N 0.000 description 1
230000003780 keratinization Effects 0.000 description 1
238000007273 lactonization reaction Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
229960003471 retinol Drugs 0.000 description 1
235000020944 retinol Nutrition 0.000 description 1
239000011607 retinol Substances 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
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
VITGGEBGJPUJMH-UHFFFAOYSA-M sodium;3-methylbut-2-enoate Chemical compound [Na+].CC(C)=CC([O-])=O VITGGEBGJPUJMH-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000017105 transposition Effects 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)

BG106369A 1999-07-30 2002-01-30 Метод за получаване на изотретиноин BG106369A (bg)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IN1037DE1999 IN190846B (de)	1999-07-30	1999-07-30
US09/467,201 US6441226B1 (en)	1999-07-30	1999-12-20	Process for the preparation of isotretinoin
PCT/IB2000/001020 WO2001009089A1 (en)	1999-07-30	2000-07-24	Process for the preparation of isotretinoin

Publications (1)

Publication Number	Publication Date
BG106369A true BG106369A (bg)	2002-08-30

Family

ID=26324696

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG106369A BG106369A (bg)	1999-07-30	2002-01-30	Метод за получаване на изотретиноин

Country Status (24)

Country	Link
EP (1)	EP1204637B1 (de)
JP (1)	JP2003506349A (de)
CN (1)	CN1167679C (de)
AP (1)	AP2002002414A0 (de)
AT (1)	ATE293596T1 (de)
AU (1)	AU778584B2 (de)
BG (1)	BG106369A (de)
BR (1)	BR0012866A (de)
CA (1)	CA2380026A1 (de)
DE (1)	DE60019611T2 (de)
EA (1)	EA004651B1 (de)
EE (1)	EE200200053A (de)
ES (1)	ES2240117T3 (de)
HK (1)	HK1046901B (de)
HR (1)	HRP20020098A2 (de)
HU (1)	HUP0202230A3 (de)
IL (1)	IL147918A0 (de)
MX (1)	MXPA02001107A (de)
OA (1)	OA12002A (de)
PL (1)	PL353491A1 (de)
PT (1)	PT1204637E (de)
SK (1)	SK1612002A3 (de)
TR (1)	TR200200455T2 (de)
WO (1)	WO2001009089A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 OA OA1200200035A patent/OA12002A/en unknown
- 2000-07-24 MX MXPA02001107A patent/MXPA02001107A/es active IP Right Grant
- 2000-07-24 CN CNB008119988A patent/CN1167679C/zh not_active Expired - Fee Related
- 2000-07-24 HU HU0202230A patent/HUP0202230A3/hu unknown
- 2000-07-24 AP APAP/P/2002/002414A patent/AP2002002414A0/en unknown
- 2000-07-24 HR HR20020098A patent/HRP20020098A2/xx not_active Application Discontinuation
- 2000-07-24 EA EA200200110A patent/EA004651B1/ru not_active IP Right Cessation
- 2000-07-24 TR TR2002/00455T patent/TR200200455T2/xx unknown
- 2000-07-24 BR BR0012866-0A patent/BR0012866A/pt not_active IP Right Cessation
- 2000-07-24 EE EEP200200053A patent/EE200200053A/xx unknown
- 2000-07-24 AT AT00944156T patent/ATE293596T1/de not_active IP Right Cessation
- 2000-07-24 WO PCT/IB2000/001020 patent/WO2001009089A1/en not_active Ceased
- 2000-07-24 PL PL00353491A patent/PL353491A1/xx not_active Application Discontinuation
- 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 IL IL14791800A patent/IL147918A0/xx not_active IP Right Cessation
- 2000-07-24 ES ES00944156T patent/ES2240117T3/es not_active Expired - Lifetime
- 2000-07-24 PT PT00944156T patent/PT1204637E/pt unknown
- 2000-07-24 EP EP00944156A patent/EP1204637B1/de not_active Expired - Lifetime
- 2000-07-24 DE DE60019611T patent/DE60019611T2/de not_active Expired - Fee Related
- 2000-07-24 CA CA002380026A patent/CA2380026A1/en not_active Abandoned
- 2000-07-24 HK HK02108127.7A patent/HK1046901B/en not_active IP Right Cessation
- 2000-07-24 SK SK161-2002A patent/SK1612002A3/sk unknown
2002
- 2002-01-30 BG BG106369A patent/BG106369A/bg unknown

Also Published As

Publication number	Publication date
PT1204637E (pt)	2005-08-31
IL147918A0 (en)	2002-08-14
HUP0202230A3 (en)	2004-03-01
DE60019611T2 (de)	2006-03-02
CA2380026A1 (en)	2001-02-08
HK1046901A1 (en)	2003-01-30
BR0012866A (pt)	2002-07-09
EA200200110A1 (ru)	2002-08-29
TR200200455T2 (tr)	2002-07-22
EE200200053A (et)	2003-04-15
MXPA02001107A (es)	2002-08-20
OA12002A (en)	2006-04-18
HUP0202230A2 (hu)	2002-11-28
EP1204637B1 (de)	2005-04-20
WO2001009089A1 (en)	2001-02-08
JP2003506349A (ja)	2003-02-18
SK1612002A3 (en)	2002-06-04
PL353491A1 (en)	2003-11-17
EP1204637A1 (de)	2002-05-15
ATE293596T1 (de)	2005-05-15
AU5838800A (en)	2001-02-19
CN1371362A (zh)	2002-09-25
AU778584B2 (en)	2004-12-09
EA004651B1 (ru)	2004-06-24
DE60019611D1 (de)	2005-05-25
HRP20020098A2 (en)	2003-12-31
CN1167679C (zh)	2004-09-22
AP2002002414A0 (en)	2002-03-31
ES2240117T3 (es)	2005-10-16
HK1046901B (en)	2005-09-23

Publication	Publication Date	Title
Rollinson et al.	1981	Total synthesis of Lauraceae lactones: obtusilactones, litsenolides, and mahubanolides
Widmer	1985	Synthetic advances in the carotenoid field
JP2022036968A (ja)	2022-03-08	３－ヒドロキシ－３，６－ジメチルヘキサヒドロベンゾフラン－２－オンおよびその誘導体の製造
Millar et al.	1984	Synthesis of Z, Z-skipped diene macrolide pheromones for Cryptolestes and Oryzaephilus grain beetles (Coleoptera Cucujidae)
MX2014012400A (es)	2015-01-12	Procedimiento mejorado para preparar (3e, 7e)-homofarnesol.
Gilbert et al.	1993	Enantioselective synthesis of (-)-trichodiene
US6441226B1 (en)	2002-08-27	Process for the preparation of isotretinoin
AU778584B2 (en)	2004-12-09	Process for the preparation of isotretinoin
JPH0237355B2 (de)	1990-08-23
CA2272439C (en)	2010-05-11	A process for the preparation of 13-cis-retinoic acid
JP3579970B2 (ja)	2004-10-20	アリールシクロプロピルケトン類の製造方法
KR100477899B1 (ko)	2005-03-18	레티놀 및 카로틴 화합물의 실용적인 합성방법
CZ2002370A3 (cs)	2002-07-17	Způsob přípravy izotretinoinu
US5808120A (en)	1998-09-15	Method of synthesis of retinoic acid
Davalian et al.	1979	Synthesis of 7, 8-epoxy-7, 8-dihydroretinoids
Kaegi et al.	1981	Preparation of all trans‐retinoic‐11‐3H acid and all trans‐retinyl‐11‐3H acetate
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