GB1438093A - Prostaglandins and the manufacture thereof - Google Patents
Prostaglandins and the manufacture thereofInfo
- Publication number
- GB1438093A GB1438093A GB52175A GB52175A GB1438093A GB 1438093 A GB1438093 A GB 1438093A GB 52175 A GB52175 A GB 52175A GB 52175 A GB52175 A GB 52175A GB 1438093 A GB1438093 A GB 1438093A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrahydropyranyl
- alkyl
- prostaglandins
- ethers
- bis
- 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
- 229940094443 oxytocics prostaglandins Drugs 0.000 title abstract 4
- 150000003180 prostaglandins Chemical class 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000002170 ethers Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- IASRMNRQZIRYHM-UHFFFAOYSA-N 6-carboxyhexyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCC(=O)O)C1=CC=CC=C1 IASRMNRQZIRYHM-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 150000002596 lactones Chemical class 0.000 abstract 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- -1 2-tetrahydropyranyl Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1438093 Prostaglandins UPJOHN CO 15 Jan 1975 [16 Oct 1973] 521/75 Divided out of 1409841 Heading C2C The invention comprises optically active prostaglands of the formulµ or racemates thereof, wherein R 1 is H C 1-12 alkyl, C 3-10 cycloalkyl, C 7-12 aralkyl or phenyl optionally substituted 1 to 3 times by halogen atoms or C 1-4 alkyl radicals; R 2 and R 3 each are H, methyl or ethyl; M is T is C 1-3 alkyl, C 1-3 alkoxy, Cl, F, or CF 3 , and s is 0 to 3, with the proviso that not more than two Ts are other than alkyl and when s is 2 or 3 the Ts may be the same or different; the alkanoates (of 2 to 8 carbon atoms in the alkanoyl radical) thereof, and salts thereof when R 1 is H. The PGE analogues are prepared by hydrolysing the corresponding 11,15-bis-(2- tetrahydropyranyl) ethers, obtained by oxidizing the 11,15-bis-(2-tetrahydropyranyl) ethers of the corresponding PGF analogues, which are obtained by reacting (6-carboxyhexyl)triphenylphosphonium bromide with lactals resulting from the reduction of lactones of the formula wherein M<SP>11</SP> is and R 8 is 2-tetrahydropyranyl. PGF analogues are prepared either by hydrolysing the corresponding 11,15-bis-(2-tetrahydropyranyl) ethers or by reacting (6-carboxyhexyl)triphenylphosphonium bromide with the lactals resulting from the reduction of lactones of the above formula in which R 8 is H. The acids obtained by the above processes may be esterified or converted into salts. Pharmaceutical compositions, suitable for oral, parenteral, rectal, vaginal or topical administration, contain the above prostaglandins or salts thereof together with pharmaceutically acceptable carriers. The compounds possess pharmacological activities similar to those of the naturally occurring prostaglandins.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB52175A GB1438093A (en) | 1973-10-16 | 1975-01-15 | Prostaglandins and the manufacture thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB52173A GB1344818A (en) | 1972-04-26 | 1973-10-16 | Apparatus for monitoring a fluid bearing |
| GB52175A GB1438093A (en) | 1973-10-16 | 1975-01-15 | Prostaglandins and the manufacture thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1438093A true GB1438093A (en) | 1976-06-03 |
Family
ID=26235989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB52175A Expired GB1438093A (en) | 1973-10-16 | 1975-01-15 | Prostaglandins and the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1438093A (en) |
-
1975
- 1975-01-15 GB GB52175A patent/GB1438093A/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |