GB1479964A - 2,3-methylene prostaglandins and their preparation - Google Patents
2,3-methylene prostaglandins and their preparationInfo
- Publication number
- GB1479964A GB1479964A GB30268/74A GB3026874A GB1479964A GB 1479964 A GB1479964 A GB 1479964A GB 30268/74 A GB30268/74 A GB 30268/74A GB 3026874 A GB3026874 A GB 3026874A GB 1479964 A GB1479964 A GB 1479964A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- alkyl
- compounds
- radical
- compound
- 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.)
- Expired
Links
- -1 2,3-methylene prostaglandins Chemical class 0.000 title abstract 4
- 229940094443 oxytocics prostaglandins Drugs 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000002997 prostaglandinlike Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- 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
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1479964 2,3-Methyleneprostaglandins SANDOZ Ltd 8 July 1974 [9 July 1973 4 May 1974] 30268/74 Heading C2C [Also in Division C3] The invention comprises optically active 2,3- methyleneprostaglandins of the formulµ or racemates thereof, wherein R 1 is H, C 1-8 alkyl, C 3-10 cycloalkyl or C 7-12 aralkyl, R 2 and R 3 each are H or C 1-4 alkyl, R 4 is 2-tetrahydropyranyl, R 6 is H, C 1-8 alkyl, C 3-10 cycloalkyl or C 7-12 aralkyl, and D is one of the four carbocyclic radicals IIa to IId and A is a carbocyclic radical of Formula IIa or IIb above or of the formula IIe or IIf and salts thereof when R 1 is H and their preparation. The compounds of Formula I above are prepared by hydrolysing the corresponding compound of Formula III, or when D is a radical of the Formula IIb by the acidic dehydration of compound of Formula I above in which D is a carbocyclic radical of the Formula IId. The esters and acids of the compound of Formula I above are obtained by esterification of the corresponding free acids and hydrolysis of the appropriate esters respectively. Compounds of the Formula III above in which A is a carbocyclic radical of the Formula IIa, IIb or IIf are obtained by oxidizing the corresponding compounds of Formula III in which A is a carbocyclic radical of the Formula IIe above or IIg or IIh Compound of Formula III in which A is a carbocyclic radical of the Formula IIe are prepared by reacting compounds of the formula E-CH=CH-CH(OR 4 )-C(R 2 )R 3 -(CH 2 ) 3 CH 3 wherein E is a radical of the Formula Vc with phosphonium halides of the Formula VI wherein X is Cl, BrI and R 5 is naphthyl or phenyl optionally substituted by alkyl, or alkyl. Pharmaceutical compositions contain the above 2,3-methylene prostaglandins of the Formula I above in association with pharmaceutical carriers or diluents. The compounds possess prostaglandin-like activity.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH995973A CH599147A5 (en) | 1973-07-09 | 1973-07-09 | Long-acting synthetic prostaglandins |
| CH604974 | 1974-05-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1479964A true GB1479964A (en) | 1977-07-13 |
Family
ID=25698889
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1901/77A Expired GB1479965A (en) | 1973-07-09 | 1974-07-08 | Cyclopropane carboxylic acid derivatives |
| GB30268/74A Expired GB1479964A (en) | 1973-07-09 | 1974-07-08 | 2,3-methylene prostaglandins and their preparation |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1901/77A Expired GB1479965A (en) | 1973-07-09 | 1974-07-08 | Cyclopropane carboxylic acid derivatives |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5040549A (en) |
| AT (1) | AT355233B (en) |
| CA (1) | CA1050976A (en) |
| DD (1) | DD113348A5 (en) |
| DE (1) | DE2431930A1 (en) |
| DK (1) | DK142143B (en) |
| ES (2) | ES428063A1 (en) |
| FI (1) | FI58117C (en) |
| FR (2) | FR2236490B1 (en) |
| GB (2) | GB1479965A (en) |
| IE (1) | IE41342B1 (en) |
| IL (1) | IL45215A (en) |
| NL (1) | NL7409119A (en) |
| NO (1) | NO742378L (en) |
| SE (2) | SE7408689L (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2638401A1 (en) * | 1975-09-05 | 1977-03-17 | Sandoz Ag | NEW PROSTAGLANDIN, THEIR USE AND MANUFACTURING |
| JPS52116930U (en) * | 1976-03-03 | 1977-09-05 | ||
| JPS55147056U (en) * | 1979-04-06 | 1980-10-22 | ||
| US4431669A (en) * | 1982-12-17 | 1984-02-14 | Schering Corporation | Cyclopropyl substituted polyenes |
| JPH04204679A (en) * | 1990-11-30 | 1992-07-27 | Fuji Photo Film Co Ltd | Electrophotographic image recorder |
-
1974
- 1974-07-01 NO NO742378A patent/NO742378L/no unknown
- 1974-07-01 DK DK352974AA patent/DK142143B/en unknown
- 1974-07-01 FI FI2011/74A patent/FI58117C/en active
- 1974-07-01 SE SE7408689A patent/SE7408689L/xx unknown
- 1974-07-03 DE DE2431930A patent/DE2431930A1/en not_active Withdrawn
- 1974-07-05 DD DD179745A patent/DD113348A5/xx unknown
- 1974-07-05 FR FR7423427A patent/FR2236490B1/fr not_active Expired
- 1974-07-05 NL NL7409119A patent/NL7409119A/en not_active Application Discontinuation
- 1974-07-08 IE IE1443/74A patent/IE41342B1/en unknown
- 1974-07-08 GB GB1901/77A patent/GB1479965A/en not_active Expired
- 1974-07-08 JP JP49077462A patent/JPS5040549A/ja active Pending
- 1974-07-08 GB GB30268/74A patent/GB1479964A/en not_active Expired
- 1974-07-08 AT AT559874A patent/AT355233B/en not_active IP Right Cessation
- 1974-07-08 ES ES74428063A patent/ES428063A1/en not_active Expired
- 1974-07-08 IL IL45215A patent/IL45215A/en unknown
- 1974-07-08 CA CA204,340A patent/CA1050976A/en not_active Expired
-
1975
- 1975-10-30 SE SE7512194A patent/SE7512194L/en unknown
-
1976
- 1976-05-17 ES ES448000A patent/ES448000A1/en not_active Expired
- 1976-10-01 FR FR7629555A patent/FR2318169A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IE41342L (en) | 1975-01-09 |
| FI58117B (en) | 1980-08-29 |
| DK142143C (en) | 1981-02-09 |
| DE2431930A1 (en) | 1975-01-30 |
| FR2236490B1 (en) | 1978-07-21 |
| FR2318169A1 (en) | 1977-02-11 |
| GB1479965A (en) | 1977-07-13 |
| IL45215A (en) | 1977-07-31 |
| NO742378L (en) | 1975-02-03 |
| JPS5040549A (en) | 1975-04-14 |
| DK142143B (en) | 1980-09-08 |
| DK352974A (en) | 1975-03-03 |
| IL45215A0 (en) | 1975-02-10 |
| ES448000A1 (en) | 1977-11-01 |
| SE7408689L (en) | 1975-01-10 |
| FR2318169B1 (en) | 1978-11-03 |
| SE7512194L (en) | 1975-10-30 |
| NL7409119A (en) | 1975-01-13 |
| ES428063A1 (en) | 1977-02-01 |
| FI58117C (en) | 1980-12-10 |
| DD113348A5 (en) | 1975-06-05 |
| FR2236490A1 (en) | 1975-02-07 |
| AT355233B (en) | 1980-02-25 |
| CA1050976A (en) | 1979-03-20 |
| IE41342B1 (en) | 1979-12-05 |
| FI201174A (en) | 1975-01-10 |
| ATA559874A (en) | 1979-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |