GB1416113A - Hexahydrocyclopenta-b-furan derivatives and a process for the manufacture thereof - Google Patents
Hexahydrocyclopenta-b-furan derivatives and a process for the manufacture thereofInfo
- Publication number
- GB1416113A GB1416113A GB5929973A GB5929973A GB1416113A GB 1416113 A GB1416113 A GB 1416113A GB 5929973 A GB5929973 A GB 5929973A GB 5929973 A GB5929973 A GB 5929973A GB 1416113 A GB1416113 A GB 1416113A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- xxii
- compounds
- prepared
- hydrolysable
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- XSDLSEOIVCVTQZ-UHFFFAOYSA-N 2h-cyclopenta[b]furan Chemical class C1=CC2=CCOC2=C1 XSDLSEOIVCVTQZ-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- -1 aci-nitro salt Chemical class 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Abstract
1416113 Cyclopenta[b]furan derivatives F HOFFMANN-LA ROCHE & CO AG 21 Dec 1973 [22 Dec 1972] 59299/73 Heading C2C Novel compounds of Formula XXII wherein R is a hydroxy group or an ether or ester group which is hydrolysable to a hydroxy group, are prepared by treating a compound of Formula XV with a peracid to yield a compound XXII in which R is acetoxy, if desired, hydrolysing this compound to give a compound XXII in which R is OH, and, if desired, subjecting the free OH compound to etherification or esterification to yield a compound XXII in which R is a hydrolysable ester or ether group other than acetoxy. Compound XV is prepared from dihydroresorcylic acid via a number of intermediates according to the following reaction scheme in which R 3 is C 2-7 alkanoyl, R 4 is C 1-7 alkyl and X is halogen: Aldehydes of Formula III in which R<SP>1</SP> is an ether or ester group hydrolysable to OH, are prepared by converting a compound XXII to an aci-nitro salt and then oxidizing said salt. Compounds III may be converted to compounds XIX and XXI by known methods. Compounds XXI may be hydrolysed to form the corresponding compound in which R<SP>1</SP> is OH.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31758972A | 1972-12-22 | 1972-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1416113A true GB1416113A (en) | 1975-12-03 |
Family
ID=23234374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5929973A Expired GB1416113A (en) | 1972-12-22 | 1973-12-21 | Hexahydrocyclopenta-b-furan derivatives and a process for the manufacture thereof |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4988860A (en) |
| AT (1) | AT337684B (en) |
| BE (1) | BE808944A (en) |
| CH (2) | CH595371A5 (en) |
| DE (1) | DE2360409A1 (en) |
| FR (1) | FR2211458B1 (en) |
| GB (1) | GB1416113A (en) |
| NL (1) | NL7317408A (en) |
-
1973
- 1973-11-22 CH CH1646973A patent/CH595371A5/xx not_active IP Right Cessation
- 1973-11-22 CH CH745877A patent/CH595372A5/xx not_active IP Right Cessation
- 1973-12-04 DE DE19732360409 patent/DE2360409A1/en not_active Withdrawn
- 1973-12-19 NL NL7317408A patent/NL7317408A/xx not_active Application Discontinuation
- 1973-12-20 FR FR7345777A patent/FR2211458B1/fr not_active Expired
- 1973-12-20 JP JP14201073A patent/JPS4988860A/ja active Pending
- 1973-12-21 GB GB5929973A patent/GB1416113A/en not_active Expired
- 1973-12-21 AT AT1077473A patent/AT337684B/en not_active IP Right Cessation
- 1973-12-21 BE BE139130A patent/BE808944A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT337684B (en) | 1977-07-11 |
| NL7317408A (en) | 1974-06-25 |
| CH595371A5 (en) | 1978-02-15 |
| FR2211458B1 (en) | 1977-06-10 |
| DE2360409A1 (en) | 1974-06-27 |
| ATA1077473A (en) | 1976-11-15 |
| FR2211458A1 (en) | 1974-07-19 |
| BE808944A (en) | 1974-06-21 |
| CH595372A5 (en) | 1978-02-15 |
| JPS4988860A (en) | 1974-08-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |