RU93004874A - 13,14-DIHYDRO-15 (R) -17-Phenyl-18, 19, 20-TRINOR-PGF2α METHOD FOR OBTAINING THEIR COMPLEX ETHERS AND CYCLOPENT (V) - Google Patents
13,14-DIHYDRO-15 (R) -17-Phenyl-18, 19, 20-TRINOR-PGF2α METHOD FOR OBTAINING THEIR COMPLEX ETHERS AND CYCLOPENT (V)Info
- Publication number
- RU93004874A RU93004874A RU93004874/04A RU93004874A RU93004874A RU 93004874 A RU93004874 A RU 93004874A RU 93004874/04 A RU93004874/04 A RU 93004874/04A RU 93004874 A RU93004874 A RU 93004874A RU 93004874 A RU93004874 A RU 93004874A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- phenyl
- compound
- dihydro
- trinor
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 2
- LMKPHJYTFHAGHK-UHFFFAOYSA-N cyclodrine Chemical compound C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 LMKPHJYTFHAGHK-UHFFFAOYSA-N 0.000 title 1
- 150000002170 ethers Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 6
- -1 isopropyl ester Chemical class 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
Claims (1)
Способ настоящего изобретения включает восстановление оксогруппы в боковой цепи соединения формулы (VII)
превращение полученного 3,3а,4,5,6,6а-гексагидро-2- оксо-4- [ 5′ -фенил- 3′ (R)-гидроксипент- 1′ -енил]-5- ( 4′ -фенилбензоилокси)- 2Н-циклопента[b] фурана формулы (VI)
гидрирование до 3,3а,4,5,6,6а-гексагидро-2-оксо-4-[ 5′ -фенил- 3′ (R)-гидрокси- 1′ -пентил] -5-( 4′ -фенилбензоилокси)-2Н-циклопента [b] фурана формулы (V)
восстановление соединения формулы (V) до 3,3а,4,5,6,6а-гексагидро-2-гидрокси-4-[ 5′ -фенил- 3′ (R)-гидрокси- 1′ -пентил]-5-( 4′ -фенилбензоилокси)-2Н-циклопента [b]-фурана формулы (IV)
удаление защитной группы у соединения формулы (IV) до получения 3,3a, 4,5,6,6а-гексагидро -2,5-дигидрокси-4-[ 5′ - фенил 3′ (R)-гидрокси- 1′ -пентил]-2Н-циклопента [b] фурана формулы (III)
и затем превращение полученного соединения формулы (III) в 13,14-дигидро-15(R)- 17-фенил-18,19,20-тринор- PGF2α формулы (II), используя 4-карбоксибутил -трифенилфосфонийгалид, и превращая соединение формулы (II) с помощью соединения общей формулы R -Х-, где R имеет указанные ранее значения, Х является атомом галоида, сульфатом, мезилом, тозилом, или любой подходящей группой, в 13,14-дигидро-15(R)-17-фенил -18,19,20-тринор- PGF2α сложные эфиры общей формулы (I).The present invention relates to a new method for producing 13,14-dihydro-15 (R) -17-phenyl-18,19,20-trinor-PGF 2α of an isopropyl ester of formula (I), where R is saturated or unsaturated, branched or unbranched or cyclic C 1 - 7 alkyl, or a phenyl or benzyl group
The method of the present invention includes the restoration of the oxo group in the side chain of the compound of formula (VII)
the conversion of the obtained 3,3a, 4,5,6,6a-hexahydro-2-oxo-4- [5'-phenyl-3 '(R) -hydroxypent-1'-phenyl] -5- (4'-phenylbenzyloxy) - 2H-cyclopenta [b] furan formula (VI)
hydrogenation to 3,3a, 4,5,6,6a-hexahydro-2-oxo-4- [5′-phenyl-3 ′ (R) -hydroxy-1 ′ -pentyl] -5- (4′-phenylbenzoyloxy) -2H-cyclopenta [b] furan formula (V)
reducing the compound of formula (V) to 3.3a, 4,5,6,6a-hexahydro-2-hydroxy-4- [5'-phenyl-3 '(R) -hydroxy- 1'-pentyl] -5- ( 4 '-phenylbenzoyloxy) -2H-cyclopenta [b] -furan of formula (IV)
removing the protective group of the compound of formula (IV) to obtain 3,3a, 4,5,6,6a-hexahydro -2,5-dihydroxy-4- [5 ′ - phenyl 3 ′ (R) -hydroxy- 1 ′ -pentyl ] -2H-cyclopenta [b] furan formula (III)
and then converting the obtained compound of formula (III) to 13,14-dihydro-15 (R) -17-phenyl-18,19,20-trinor-PGF 2α of formula (II) using 4-carboxybutyl-triphenylphosphonium halide, and converting the compound of formula (II) using a compound of the general formula R —X—, where R has the previously indicated meanings, X is a halogen atom, sulfate, mesyl, tosyl, or any suitable group, in 13,14-dihydro-15 (R) -17 -phenyl-18,19,20-thinor-PGF 2α esters of general formula (I).
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU2092/91 | 1991-06-24 | ||
| HU2092191 | 1991-06-24 | ||
| HU912092A HU212570B (en) | 1991-06-24 | 1991-06-24 | Process for producing 13,14-dihydro-15(r)-17-phenyl-18,19,20-trinor-pgf2alfa-isopropylester |
| PCT/HU1992/000025 WO1993000329A1 (en) | 1991-06-24 | 1992-06-19 | Chemical process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU93004874A true RU93004874A (en) | 1995-11-27 |
| RU2099325C1 RU2099325C1 (en) | 1997-12-20 |
Family
ID=10957725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU9393004874A RU2099325C1 (en) | 1991-06-24 | 1992-06-19 | METHOD OF SYNTHESIS OF 13,14-DIHYDRO-15(R)-17-PHENYL-18,19,20-TRINOR-PGF2α ESTER |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5466833A (en) |
| EP (1) | EP0544899B1 (en) |
| JP (1) | JP2635213B2 (en) |
| KR (1) | KR0163022B1 (en) |
| CN (1) | CN1035764C (en) |
| AT (1) | ATE127450T1 (en) |
| AU (1) | AU656994B2 (en) |
| BG (1) | BG61261B1 (en) |
| CZ (1) | CZ287168B6 (en) |
| DE (1) | DE69204627T2 (en) |
| DK (1) | DK0544899T3 (en) |
| ES (1) | ES2078055T3 (en) |
| FI (1) | FI104895B (en) |
| GR (1) | GR3017874T3 (en) |
| HU (1) | HU212570B (en) |
| IE (1) | IE71645B1 (en) |
| IL (1) | IL102280A (en) |
| PL (1) | PL170728B1 (en) |
| RO (1) | RO117323B1 (en) |
| RU (1) | RU2099325C1 (en) |
| TW (1) | TW310321B (en) |
| UA (1) | UA39864C2 (en) |
| WO (1) | WO1993000329A1 (en) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5510383A (en) † | 1993-08-03 | 1996-04-23 | Alcon Laboratories, Inc. | Use of cloprostenol, fluprostenol and their salts and esters to treat glaucoma and ocular hypertension |
| US6294563B1 (en) | 1994-10-27 | 2001-09-25 | Allergan Sales, Inc. | Combinations of prostaglandins and brimonidine or derivatives thereof |
| US6225348B1 (en) | 1998-08-20 | 2001-05-01 | Alfred W. Paulsen | Method of treating macular degeneration with a prostaglandin derivative |
| IL143477A (en) | 2001-05-31 | 2009-07-20 | Finetech Pharmaceutical Ltd | Process for the preparation of 17-phenyl-18,19,20-trinor-pgf2?? and its derivatives |
| IL134241A (en) | 2000-01-27 | 2006-06-11 | Finetech Pharmaceutical Ltd | Process for the preparation of latanoprost |
| GB0112699D0 (en) * | 2001-05-24 | 2001-07-18 | Resolution Chemicals Ltd | Process for the preparation of prostglandins and analogues thereof |
| US20110065129A1 (en) * | 2001-07-27 | 2011-03-17 | Lowe Derek B | Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation |
| US20050119262A1 (en) * | 2003-08-21 | 2005-06-02 | Pharmacia Corporation | Method for preventing or treating an optic neuropathy with a cox-2 inhibitor and an intraocular pressure reducing agent |
| ITRM20050231A1 (en) * | 2005-05-13 | 2006-11-14 | Technopharma Sa | PROCEDURE FOR THE SYNTHESIS OF PROSTAGLANDINE DERIVATIVES F. |
| US8546114B2 (en) | 2006-01-18 | 2013-10-01 | Chirogate International Inc. | Processes for the preparation of optically active cyclopentenones and cyclopentenones prepared therefrom |
| US7511168B2 (en) | 2006-01-18 | 2009-03-31 | Shih-Yi Wei | Processes and intermediates for the preparations of prostaglandins |
| JP2008037782A (en) * | 2006-08-04 | 2008-02-21 | Daiichi Fine Chemical Co Ltd | Method for producing prostaglandine derivative |
| US7642370B2 (en) | 2006-08-07 | 2010-01-05 | Daiichi Fine Chemical Co., Ltd. | Method for preparing prostaglandin derivative |
| IT1392492B1 (en) | 2008-12-24 | 2012-03-09 | Ind Chimica Srl | PROCESS FOR THE PURIFICATION OF LATANOPROST, SYNTHETIC ANALOGUE OF PROSTAGLANDINA PGF2ALFA. |
| PH12012501320A1 (en) * | 2010-01-11 | 2013-01-21 | Inotek Pharmaceuticals Corp | Combination, kit and method of reducing intraocular pressure |
| WO2011119969A1 (en) | 2010-03-26 | 2011-09-29 | Inotek Pharmaceuticals Corporation | Method of reducing intraocular pressure in humans using n6 -cyclopentyladenosine (cpa), cpa derivatives or prodrugs thereof |
| EP2495235B1 (en) | 2011-03-04 | 2015-08-05 | Newchem S.p.A. | Process for the synthesis of prostaglandins and intermediates thereof |
| RU2618223C2 (en) | 2011-06-02 | 2017-05-03 | ХИНОИН Зрт. | New methods of prostaglandin amides obtaining |
| HU231203B1 (en) * | 2011-12-21 | 2021-10-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Novel process for the preparation of travoprost |
| HRP20171204T1 (en) | 2012-01-26 | 2017-10-06 | Inotek Pharmaceuticals Corporation | ANHYDRID POLYMORPHES FROM [(2R, 3S, 4R, 5R) -5- (6- (CYCLOPENTYLAMINO) -9H-PURIN-9-IL) -3,4-Dihydroxytetrahydrofuran-2-yl)] METHYL-NITRATE AND THEIR PRODUCTS |
| HU230744B1 (en) * | 2012-11-30 | 2018-01-29 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Novel process for preparing travoprost |
| EP2968389A4 (en) | 2013-03-15 | 2016-08-24 | Inotek Pharmaceuticals Corp | OPHTHALMIC FORMULATIONS |
| HU231214B1 (en) * | 2014-03-13 | 2021-11-29 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | New process for preparing high purity prostaglandins |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE786251A (en) * | 1971-07-14 | 1973-01-15 | Ici Ltd | NEW DERIVATIVES OF CYCLOPENTANE |
| US3971826A (en) * | 1972-07-13 | 1976-07-27 | Pfizer Inc. | 15-Substituted-ω-pentanorprostaglandins |
| DE03014533T1 (en) * | 1988-09-06 | 2004-07-15 | Pharmacia Ab | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
-
1991
- 1991-06-24 HU HU912092A patent/HU212570B/en unknown
-
1992
- 1992-06-19 RO RO93-00230A patent/RO117323B1/en unknown
- 1992-06-19 EP EP92915265A patent/EP0544899B1/en not_active Expired - Lifetime
- 1992-06-19 AU AU22629/92A patent/AU656994B2/en not_active Expired
- 1992-06-19 DK DK92915265.0T patent/DK0544899T3/en active
- 1992-06-19 DE DE69204627T patent/DE69204627T2/en not_active Expired - Lifetime
- 1992-06-19 RU RU9393004874A patent/RU2099325C1/en active
- 1992-06-19 UA UA94010047A patent/UA39864C2/en unknown
- 1992-06-19 ES ES92915265T patent/ES2078055T3/en not_active Expired - Lifetime
- 1992-06-19 KR KR1019930700530A patent/KR0163022B1/en not_active Expired - Lifetime
- 1992-06-19 WO PCT/HU1992/000025 patent/WO1993000329A1/en active IP Right Grant
- 1992-06-19 AT AT92915265T patent/ATE127450T1/en active
- 1992-06-19 PL PL92298127A patent/PL170728B1/en unknown
- 1992-06-19 JP JP5501414A patent/JP2635213B2/en not_active Expired - Lifetime
- 1992-06-22 IL IL102280A patent/IL102280A/en not_active IP Right Cessation
- 1992-06-24 CN CN92108844A patent/CN1035764C/en not_active Expired - Lifetime
- 1992-07-01 IE IE922026A patent/IE71645B1/en not_active IP Right Cessation
- 1992-09-23 TW TW081107537A patent/TW310321B/zh not_active IP Right Cessation
-
1993
- 1993-02-22 FI FI930773A patent/FI104895B/en not_active IP Right Cessation
- 1993-02-23 BG BG97471A patent/BG61261B1/en unknown
- 1993-02-24 CZ CZ1993271A patent/CZ287168B6/en not_active IP Right Cessation
-
1994
- 1994-10-06 US US08/319,327 patent/US5466833A/en not_active Expired - Lifetime
-
1995
- 1995-10-25 GR GR950402979T patent/GR3017874T3/en unknown
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