IL36682A - 15-alkyl prostaglandins - Google Patents
15-alkyl prostaglandinsInfo
- Publication number
- IL36682A IL36682A IL36682A IL3668271A IL36682A IL 36682 A IL36682 A IL 36682A IL 36682 A IL36682 A IL 36682A IL 3668271 A IL3668271 A IL 3668271A IL 36682 A IL36682 A IL 36682A
- Authority
- IL
- Israel
- Prior art keywords
- methyl
- inclusive
- racemic
- compound according
- formula
- Prior art date
Links
- 229940094443 oxytocics prostaglandins Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 150000004702 methyl esters Chemical class 0.000 claims 4
- 239000000047 product Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- -1 inclusive Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 229960002986 dinoprostone Drugs 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 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
- 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
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)
- Medicines Containing Plant Substances (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Claims (28)
1. A process for producing an optically active compound of the f o rmu 1 a : or a racemic compound of that formula and the mirror image thereof, or the 15-epimer of either of those, wherein X is trans-CH=CH- or -CH2CH2-, and Y and Z are both -CH2CH2- , or wherein X is trans-CH=CH- and Y is cis-CHsCH-, and Z is -CH2CH2' in iii I ΓΙΙ111ΓΤΤ wherein R2 is methyl or ethyl, wherein R4 is hydrogen or alkyl of ope to 8 carbon atoms, inclusive, and wherein indicates attachment of hydroxy %o the ring in alpha or beta configuration, which comprises the steps, ( ) reacting an optically active compound of the formula: 0 (A)3-Si- Y- (CH2)3-C-0-R3 (A)3-Si- CH2-Z-CH2CH3 or a racemic compound of that formula and the mirror image thereof, wherein A is alkyl of one to 4 carbon atoms, inclusive,^ phenyl, phenyl substituted with one or 2 fluoro, chloro, or alkyl of one to carbon atoms, inclusive, or alkyl of to 12 carbon atoms, inclusive, wherein R3 is alkyl of one to 8 carbon atoms, inclusive, or -Si (A )3 wherein A i§ as defined above, and wherein X, Y, Z, and ^-τ^ are as defined above, with a compound of the formula R2MgX wherein X is chloro, bromo, or iodOj and R2 is as defined above, and (2) hydrolyzing the reaction product of step (l).
2. A process according to claim 1 wherein the product is optically active, with the formula shown*
3. A process according to claim 1 wherein the product is racemic, with the formula shown and the mdaror image thereof.
4. . A process according to claim 1 wherein the product is optically active, with the formula shown but epimeric at C-15»
5. A purocess according to claim 1 wherein the product is racemic, with the formula shown and the mirror image thereof but both epimeric at C-15.
6. An optically active compound of the formula t or a racemic compound of that formula and the mirror image thereof, wherein is hydrogen, alkyl of one to 8 carbon atoms, inclusive, or a pharmacologically acceptable cation, wherein R9 is methyl or ethyl, wherein A is - erein X is trans -CH=CH- or -CHgCHg- and Y and Z are both -CH2CH2-, or wherein X is trans-CH=CH- , Y is cis-CH=CH- , and Z proviso that R9 is ethyl when A is =0 or , and Y and Z are both -CH2CH2-.
7. * A compound according to claim 6 wherein A is =0.
8. A compound according to claim 6 wherein A is
9. A compound according to claim 6 wherein A is ^OH.
10. A compound according to any one of claims 6 to 9i inclusive, wherein X, Y, and Z are all -CHgCHg-.
11. A compound according to any one of claims 6 to 9» inclusive, wherein X is trans-CH=CH- , and Y and Z are both -CHgCHg-.
12. A compound according to any one of claims 6 to 9, inclusive, wherein X is trans-CH==CH, Y is cis-CH=CH-, and Z is -CH2CH2-.
13. A compound according to any one <£ claims to 12, inclusive wherein R^ is hydrogen.
14. A compound according to any one of claims 6 to 12, inclusive wherein R^ is methyl.
15. An optically active compound according to any one of claims 6 to 14, inclusive.
16. A racemic compound according to any one of claims 6 to 14, Inclusive.
17. Dihydro-15-methyl-K^ methyl ester.
18. Dihydro-15-methyl-PGF methyl ester. la
19. Dihydro-15-methyl-PGF^.
20. 15-Eth l-PGF2a- -methyl ester.
21. 15- ethyl-PGF .
22. 15-Methyl-PGE2its methyl ester and isopropyl ester.
23. 15-Methyl-PGF2a, its methyl ester and THAM salt.
24. 15-Methyl-PGF2£ and its methyl ester.
25. Racemic 15-methyl-PGFnQ. Ip
26. Racemlc 15-methyl-PGE2.
27. Racemic 15-methyl-PGF^ .
28. Racemic 15-methyl-PGF
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3451870A | 1970-05-04 | 1970-05-04 | |
| US3454970A | 1970-05-04 | 1970-05-04 | |
| US3730770A | 1970-05-14 | 1970-05-14 | |
| US3730870A | 1970-05-14 | 1970-05-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL36682A0 IL36682A0 (en) | 1971-06-23 |
| IL36682A true IL36682A (en) | 1976-04-30 |
Family
ID=27488226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL36682A IL36682A (en) | 1970-05-04 | 1971-04-21 | 15-alkyl prostaglandins |
Country Status (9)
| Country | Link |
|---|---|
| CA (1) | CA959485A (en) |
| DE (2) | DE2121980C3 (en) |
| FR (1) | FR2100627B1 (en) |
| GB (2) | GB1314293A (en) |
| IL (1) | IL36682A (en) |
| MY (1) | MY7400305A (en) |
| NL (1) | NL154729B (en) |
| NO (2) | NO135935C (en) |
| SE (1) | SE388852B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2258668C3 (en) * | 1971-12-03 | 1981-08-06 | Syntex Corp., Panama-City | New prostaglandins, processes for their production and pharmaceuticals containing them |
| US3887587A (en) * | 1972-04-17 | 1975-06-03 | Pfizer | Synthesis of prostaglandins of the one-series |
-
1971
- 1971-04-15 CA CA110,447A patent/CA959485A/en not_active Expired
- 1971-04-21 IL IL36682A patent/IL36682A/en unknown
- 1971-04-29 SE SE7105577A patent/SE388852B/en unknown
- 1971-05-03 NO NO1638/71A patent/NO135935C/no unknown
- 1971-05-03 FR FR7115790A patent/FR2100627B1/fr not_active Expired
- 1971-05-03 NL NL717105999A patent/NL154729B/en not_active IP Right Cessation
- 1971-05-04 GB GB4292972A patent/GB1314293A/en not_active Expired
- 1971-05-04 DE DE2121980A patent/DE2121980C3/en not_active Expired
- 1971-05-04 DE DE2166630A patent/DE2166630C3/en not_active Expired
- 1971-05-04 GB GB1289871*[A patent/GB1314291A/en not_active Expired
-
1972
- 1972-06-13 NO NO2080/72A patent/NO140422C/en unknown
-
1974
- 1974-12-30 MY MY305/74A patent/MY7400305A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2121980C3 (en) | 1980-02-14 |
| SE388852B (en) | 1976-10-18 |
| IL36682A0 (en) | 1971-06-23 |
| NO140422B (en) | 1979-05-21 |
| DE2166630B2 (en) | 1979-02-22 |
| NL154729B (en) | 1977-10-17 |
| DE2166630A1 (en) | 1974-12-12 |
| GB1314293A (en) | 1973-04-18 |
| GB1314291A (en) | 1973-04-18 |
| NO135935B (en) | 1977-03-21 |
| DE2121980B2 (en) | 1979-06-07 |
| FR2100627B1 (en) | 1981-12-18 |
| NO135935C (en) | 1977-06-29 |
| DE2166630C3 (en) | 1979-10-11 |
| NL7105999A (en) | 1971-11-08 |
| NO140422C (en) | 1979-08-29 |
| CA959485A (en) | 1974-12-17 |
| FR2100627A1 (en) | 1972-03-24 |
| DE2121980A1 (en) | 1971-11-25 |
| MY7400305A (en) | 1974-12-31 |
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