DE2627673A1 - Prostaglandinartige 1,15-lactone sowie verfahren zu deren herstellung - Google Patents
Prostaglandinartige 1,15-lactone sowie verfahren zu deren herstellungInfo
- Publication number
- DE2627673A1 DE2627673A1 DE19762627673 DE2627673A DE2627673A1 DE 2627673 A1 DE2627673 A1 DE 2627673A1 DE 19762627673 DE19762627673 DE 19762627673 DE 2627673 A DE2627673 A DE 2627673A DE 2627673 A1 DE2627673 A1 DE 2627673A1
- Authority
- DE
- Germany
- Prior art keywords
- compound according
- formula
- radical
- lactone
- methyl
- 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- Withdrawn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
- 230000002997 prostaglandinlike Effects 0.000 title claims description 26
- 238000000034 method Methods 0.000 title description 245
- 238000002360 preparation method Methods 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims description 506
- -1 methyl radicals Chemical class 0.000 claims description 165
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 89
- 239000000203 mixture Substances 0.000 claims description 88
- 150000003254 radicals Chemical class 0.000 claims description 66
- 229910052731 fluorine Inorganic materials 0.000 claims description 55
- 239000007795 chemical reaction product Substances 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- 230000002829 reductive effect Effects 0.000 claims description 41
- 229910052801 chlorine Inorganic materials 0.000 claims description 35
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 258
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 231
- 239000000243 solution Substances 0.000 description 123
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 107
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- 150000003180 prostaglandins Chemical class 0.000 description 94
- 150000002596 lactones Chemical class 0.000 description 85
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 60
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 57
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 239000011737 fluorine Substances 0.000 description 50
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 41
- 125000006239 protecting group Chemical group 0.000 description 40
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 25
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- 239000007858 starting material Substances 0.000 description 14
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical class O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 13
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- 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
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58972475A | 1975-06-23 | 1975-06-23 | |
| US05/670,524 US4045449A (en) | 1975-06-23 | 1976-03-29 | PG-type 1,15-lactones |
| US05/670,523 US4032543A (en) | 1975-06-23 | 1976-03-29 | Pg-type 1,11-lactones |
| US05/670,522 US4049648A (en) | 1975-06-23 | 1976-03-29 | PG-type, 1,9-lactones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2627673A1 true DE2627673A1 (de) | 1977-01-20 |
Family
ID=27504992
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762627673 Withdrawn DE2627673A1 (de) | 1975-06-23 | 1976-06-21 | Prostaglandinartige 1,15-lactone sowie verfahren zu deren herstellung |
| DE19762627671 Withdrawn DE2627671A1 (de) | 1975-06-23 | 1976-06-21 | Arzneimittel, enthaltend ein lacton eines prostaglandins oder prostaglandinanalogen |
| DE19762627674 Withdrawn DE2627674A1 (de) | 1975-06-23 | 1976-06-21 | Prostaglandinartige 1,11-lactone und ein verfahren zu ihrer herstellung |
| DE19762627675 Withdrawn DE2627675A1 (de) | 1975-06-23 | 1976-06-21 | 1,9-lactone von prostaglandinderivaten und verfahren zu ihrer herstellung |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762627671 Withdrawn DE2627671A1 (de) | 1975-06-23 | 1976-06-21 | Arzneimittel, enthaltend ein lacton eines prostaglandins oder prostaglandinanalogen |
| DE19762627674 Withdrawn DE2627674A1 (de) | 1975-06-23 | 1976-06-21 | Prostaglandinartige 1,11-lactone und ein verfahren zu ihrer herstellung |
| DE19762627675 Withdrawn DE2627675A1 (de) | 1975-06-23 | 1976-06-21 | 1,9-lactone von prostaglandinderivaten und verfahren zu ihrer herstellung |
Country Status (5)
| Country | Link |
|---|---|
| US (4) | US4045449A (enExample) |
| DE (4) | DE2627673A1 (enExample) |
| FR (4) | FR2315267A1 (enExample) |
| GB (3) | GB1554023A (enExample) |
| NL (4) | NL7606612A (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA772255B (en) * | 1976-05-04 | 1978-11-29 | Upjohn Co | Prostaglandin analogs |
| US4102897A (en) * | 1976-08-20 | 1978-07-25 | The Upjohn Company | Dialkylacetal-containing thromboxane B, 1,9-lactone intermediates |
| US4131738A (en) * | 1977-07-05 | 1978-12-26 | The Upjohn Company | 6-Hydroxy-PGE1 compounds |
| US4188332A (en) * | 1978-04-05 | 1980-02-12 | The Upjohn Company | Trans-2,3-didehydro-9-deoxy-9-methylene-PGF,1,11- or 1,15-lactones |
| US4289785A (en) * | 1980-08-06 | 1981-09-15 | The Upjohn Company | Method and compositions involving prostaglandins |
| US4927846A (en) * | 1988-11-23 | 1990-05-22 | Allergan, Inc. | Intraocular pressure reducing 1,11-lactone prostaglandins |
| US5028624A (en) * | 1989-07-27 | 1991-07-02 | Allergan, Inc. | Intraocular pressure reducing 9,15-diacyl prostaglandins |
| JP3181677B2 (ja) | 1992-03-25 | 2001-07-03 | 旭硝子株式会社 | 双環性エノールラクトン類とその製造方法 |
| JP2003531824A (ja) * | 2000-02-01 | 2003-10-28 | ケイマン ケミカル カムパニー，インク． | フルプロステノールおよび関連プロスタグランジンＦ２α類似体の内部１，１５−ラクトン、ならびに緑内障および眼高血圧の治療におけるそれらの使用 |
| US7504739B2 (en) | 2001-10-05 | 2009-03-17 | Enis Ben M | Method of transporting and storing wind generated energy using a pipeline |
| EP1501530B1 (en) * | 2002-03-21 | 2009-02-18 | Cayman Chemical Company | Prostaglandin f2 alpha analogs in combination with antimicrobial for treating glaucoma |
| ES2824842T3 (es) | 2009-07-13 | 2021-05-13 | Patheon Api Services Inc | Síntesis de prostanoides |
| US9115109B2 (en) * | 2013-08-15 | 2015-08-25 | Chirogate International Inc. | Processes and intermediates for the preparations of isomer free prostaglandins |
| JP6488472B2 (ja) | 2013-09-30 | 2019-03-27 | パテオン エーピーアイ サービシーズ インコーポレイテッドＰａｔｈｅｏｎ Ａｐｉ Ｓｅｒｖｉｃｅｓ Ｉｎｃ． | メタセシスを用いるプロスタグランジンおよびプロスタグランジン中間体の新規合成経路 |
| WO2019113210A1 (en) | 2017-12-05 | 2019-06-13 | Anthos Partners, Lp | Phosphonium-based ionic drug conjugates |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3872107A (en) * | 1972-09-08 | 1975-03-18 | Syntex Inc | Difluoromethylene substituted prostaglandin intermediates |
| JPS5013385A (enExample) * | 1973-06-08 | 1975-02-12 |
-
1976
- 1976-03-29 US US05/670,524 patent/US4045449A/en not_active Expired - Lifetime
- 1976-03-29 US US05/670,523 patent/US4032543A/en not_active Expired - Lifetime
- 1976-03-29 US US05/670,522 patent/US4049648A/en not_active Expired - Lifetime
- 1976-06-03 US US05/692,439 patent/US4067991A/en not_active Expired - Lifetime
- 1976-06-18 NL NL7606612A patent/NL7606612A/xx not_active Application Discontinuation
- 1976-06-21 DE DE19762627673 patent/DE2627673A1/de not_active Withdrawn
- 1976-06-21 DE DE19762627671 patent/DE2627671A1/de not_active Withdrawn
- 1976-06-21 DE DE19762627674 patent/DE2627674A1/de not_active Withdrawn
- 1976-06-21 DE DE19762627675 patent/DE2627675A1/de not_active Withdrawn
- 1976-06-22 FR FR7618967A patent/FR2315267A1/fr active Granted
- 1976-06-22 FR FR7618966A patent/FR2315266A1/fr active Granted
- 1976-06-22 FR FR7618969A patent/FR2361877A1/fr active Granted
- 1976-06-22 NL NL7606764A patent/NL7606764A/xx unknown
- 1976-06-22 NL NL7606765A patent/NL7606765A/xx not_active Application Discontinuation
- 1976-06-22 NL NL7606763A patent/NL7606763A/xx not_active Application Discontinuation
- 1976-06-22 FR FR7618968A patent/FR2315268A1/fr active Granted
- 1976-06-23 GB GB26181/76A patent/GB1554023A/en not_active Expired
- 1976-06-23 GB GB26185/76A patent/GB1554025A/en not_active Expired
- 1976-06-23 GB GB26180/76A patent/GB1554024A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2627675A1 (de) | 1977-01-13 |
| DE2627674A1 (de) | 1977-01-20 |
| FR2315268B1 (enExample) | 1984-06-29 |
| FR2361877A1 (fr) | 1978-03-17 |
| NL7606764A (nl) | 1976-12-27 |
| AU1428776A (en) | 1977-12-01 |
| NL7606765A (nl) | 1976-12-27 |
| FR2315266A1 (fr) | 1977-01-21 |
| GB1554025A (en) | 1979-10-17 |
| NL7606612A (nl) | 1976-12-27 |
| AU1428976A (en) | 1977-12-01 |
| DE2627671A1 (de) | 1977-01-13 |
| GB1554023A (en) | 1979-10-17 |
| FR2361877B1 (enExample) | 1984-03-16 |
| US4045449A (en) | 1977-08-30 |
| GB1554024A (en) | 1979-10-17 |
| AU1429076A (en) | 1977-12-01 |
| FR2315267B1 (enExample) | 1984-03-16 |
| US4032543A (en) | 1977-06-28 |
| NL7606763A (nl) | 1976-12-27 |
| US4049648A (en) | 1977-09-20 |
| US4067991A (en) | 1978-01-10 |
| FR2315267A1 (fr) | 1977-01-21 |
| FR2315268A1 (fr) | 1977-01-21 |
| FR2315266B1 (enExample) | 1979-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |