IL39079A - 16-loweralkyl and 16,16-diloweralkyl prostaglandins of the a2,b2,e2,and f2 types and process for making them - Google Patents
16-loweralkyl and 16,16-diloweralkyl prostaglandins of the a2,b2,e2,and f2 types and process for making themInfo
- Publication number
- IL39079A IL39079A IL39079A IL3907972A IL39079A IL 39079 A IL39079 A IL 39079A IL 39079 A IL39079 A IL 39079A IL 3907972 A IL3907972 A IL 3907972A IL 39079 A IL39079 A IL 39079A
- Authority
- IL
- Israel
- Prior art keywords
- hydrogen
- methyl
- compound
- formula
- racemic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 13
- 229940094443 oxytocics prostaglandins Drugs 0.000 title 1
- 150000003180 prostaglandins Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 45
- 229910052739 hydrogen Inorganic materials 0.000 claims 45
- 239000001257 hydrogen Substances 0.000 claims 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 24
- 150000002431 hydrogen Chemical class 0.000 claims 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 230000003287 optical effect Effects 0.000 claims 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 101150052863 THY1 gene Proteins 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 229960002986 dinoprostone Drugs 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- OKTJSMMVPCPJKN-BJUDXGSMSA-N carbon-11 Chemical group [11C] OKTJSMMVPCPJKN-BJUDXGSMSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000018044 dehydration Effects 0.000 claims 2
- 238000006297 dehydration reaction Methods 0.000 claims 2
- PRFXRIUZNKLRHM-UHFFFAOYSA-N l-prostaglandin B2 Natural products CCCCCC(O)C=CC1=C(CC=CCCCC(O)=O)C(=O)CC1 PRFXRIUZNKLRHM-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 230000009466 transformation Effects 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 claims 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 claims 1
- -1 tetrahydropyranyl oxy groups Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (1)
1. 2701 WHAT IS CLAIMED IS: -1- optical ly active compound of the formula or a racemic compound of that formula and the mirror image thereof, wherein ) is one of the four carbocyclic moieties wherein f~\ indicates attachment of hydroxyl to the cyclo- pentane ring in alpha or beta configuration, wherein Ri is hydrogen, a 1 ky 1 of one to 8 carbon atoms, inclusive, or a pharmacological ly acceptable cation, and wherein R2 and R3 are hydrogen, methyl, or ethyl, provided that at least one of R≥ and R3 is not hydrogen. . ., -2- An opt i ca 11 y act i ve compound according to claim 1. A racemic compound according to claim 1. -4- An optical ly active or racemic compound according to claim 1 w he re i n T) is 2701 0 ; HO and i is hydrogen or alkyl of one to 4 carbon atoms, s i ve . -5- An optically active or racemi c compound according to claim 1 wherei n T) is R.i is hydrogen or alkyl of one to 4 carbon atoms, inclusive and \ indicates alpha or beta attachment of hydroxyl to the cyclopentane ring. -6- An optically active or racemi c compound according to claim 1 wherein ) is and Ri is hydrogen or alkyl of one to 4 carbon atoms, i n c 1 u s i ve . An optically active or racemi c compound according to c 1 a i m 1 he re i n ) is 2701 and Ri is hydrogen or alkyl of one to 4 carbon atoms, inclu s i ve . -8- 16-Methy 1 -PGE2 , optically active compounds according to claim. wherein Ri and R2 are hydrogen, and R3 is methyl -9- Racemic Ιβ-me thy 1 - PGE2 , compounds according to claim 4 wherein Ri and R2 are hydrogen, and R3 is methyl. -10- l6, 16-Di methyl -PGE2, an optical ly active compound according to claim 4 wherein Ri is hydrogen, and R≤ and R3 a re me thy 1. -11- Racemic l6,l6-d i me thy 1 - PGE≤ , a compound according to claim 4 wherein Ri is hydrogen, and R≥ and R3 are methyl. -12- Ιβ-Methy 1 -PGF2a, optically active compounds accord i ng to claim 5 wherein Ri and R2 are hydrogen, R3 is methyl and O i s a lpha . -13- Racemic 16-Methy 1 -PGF2a, compounds according to claim 5 wherein Ri and R2 are hydrogen, R3 is methyl, and <^-J i s a 1 pha . -14- l6, 16-D i methy 1 - PGF2a, an optically active compound according to claim 5 wherein Ri is hydrogen, R2 and R3 are meth l, and r^-J is alpha. -15- Racemic l6, 16-d i me thy 1 - PGF2a, a compound according to claim 5 wherein Ri is hydrogen, R2 and R3 are methyl, and 39079/2 t^~) is alpha. -16- 16- ethyl -PGF2 β , optically active compounds according to claim 5 wherein and R2 are hydrogen, is methyl and is beta. -17- Racemic 16-Methyl-PGF,-. β , compounds according to claim 5 wherein R-| and R2 are hydrogen, R^ is methyl, and is beta. -18- 16-Methyl-PGA2, optically active compounds according to claim 6 wherein R- and R2 are hydrogen, and Rg is methyl. -19- Racemic 16-methyl-PGA2, compounds according to claim 6 wherein R- and R2 are hydrogen, and R3 is methyl. -20- 16,16-Dimethyl-PGA2, an optically active compound according to claim 6 wherein R-j is hydrogen, and R2 and Rg are methyl . -65- 39079/2 Ιβ-Methy 1 - PGB2 , optical ly active compounds accordi ng to claim 7 wherein Ri and R2 are hydrogen, and R3 is methyl - 22 - Racemic l6-mefhy 1 -PGB2 ,' compounds accordi ng to claim 7 wherein Ri and R2 are hydrogen,; and R3 is methyl . - 23 -- l6, l6-D i me thy 1 - PGB2 , an optical ly acti e compound according to claim 7 wherein Ri is hydrogen and R2 and R3 a re me t h y 1. . - 24 - A process for preparing an optical ly active compound of the formula or a racemic compound of that formula and the mirror image the re of, whe re i n 2 and R3 are hydrogen, methyl, or ethyl, provided that at least one of R2 and R3 is not hydrogen; which comprises starting with an optical ly active or racemic compound of the formula 39079/2 0 wherein and are as defined above, and Rg is hydrogen or tetrahydropyranyl, and subjecting said compound successively to the following reactions: a) reduction of the laxtone oxo group to a hydroxy group; b) Wittig al Ration with a compound of the formula Hal-CCH^-COOH wherein Hal is bromo or chloro; and c) transformation of tetrahydropyranyl oxy groups to hydroxy groups; with the proviso that step c) is omitted when Rj- is hydrogen. -25- A process according to claim 24 wherein R^ is tetrahydropyranyl . -26- A process according to claim 25 wherein R2 is hydrogen and R3 is methyl. -27- A process according to claim 25 wherein R£ and Rg are methyl . -28- A process according to claim 24 wherein R5 is hydrogen, and step c) is omitted. -29- A process according to claim 28 wherein R? is hydrogen 2701 and R3 is methyl . - 0- 30- 28 A process according to claim ββ wherein R≤ and 3 are me thy 1. -It- -31- A process for preparing an optical ly active compound of the formula or a racemi c compound of that formula and the mi rror image thereof, wherein R2 and R3 are hydrogen, methyl, or ethyl, provided that at least one of R≤ and R3 is not hydrogen, which comprises starting with an opt i ca 11 y act i ve or racemi c compound of the formula wherein R2 and R3.are as defined above, and subjecting said compound successively to the fol lowing reactions: a) replacement of the hydroxyl hydrogens by tetra-hydropyranyl groups; b) reduction of the lactone oxo group to a hydroxy group; c) Wittig alkylation with a compound of the formula Ha 1 - (CH2 -COOH - wherein Hal is bromo or chloro; 2701 d ) oxidation of the 9-hydroxy to oxo; and e) transformation of the tetrahydropyrany loxy groups to hydroxy groups. -h- 31 A process according to claim J wherein R2 is hydrogen and Rs is me thy 1. -Kb- 33- 31 A process according to claim 7fi wherein R≥ and 3 are me thy 1. ■-nh- 34- A process for produci ng an optically active compound of the formula or a racemic compound of that formula and the mirror image thereof, wherein R≤ and R3 are hydrogen, methyl, or ethyl, provided that at least one of R≥ and R3 is not hydrogen; wherein R7. is hydrogen or alky 1 of one to 8 carbon atoms, inclusive; and wherein r\ indicates attachment of hydroxyl to the cyclopentane ring in alpha or beta configuration; which comprises reacting an optical ly active or racemic compound of the formula 2701 wherein R2, R3, and R7 are as defined above, with a car-bonyl reducing agent which does not alter ester, acid, or ethylenic moieties. 35 -n- A process for producing an optical ly active compound of the formula or a racemic compound of that formula and the mirror image thereof, wherein R∑ and R3 are hydrogen, methyl, or ethyl, provided that at least one of R2 and R3 is not hydrogen; and wherein R7 is hydrogen or a 1 ky 1 of one to 8 carbon atoms, inclusive; which comprises acid dehydration of an optically active or racemic compound of the formula wherein R2 R3, and R7 are as defi ned above . -7&- 36- A process for producing an optically active compound of the formu la or a racemic compound of that formula and the mirror image thereof, wherein R2 and R3 are hydrogen, methyl, or ethyl, 2701 9 provided that at least one of R2 and 3 is not hydrogen; 10 and wherein R7 is hydrogen or alky 1 of one to 8 carbon 11 atoms, inclusive; which comprises carbodiimide dehydration 12 of an optically active or racemic compound of the formula IT wherein R2, R3, and RY are as defined above. -77- -37- 1 A process for producing an optically active compound 2 of the formula 7 or a racemic compound of that formula and the mirror image 8 thereof, wherein R2 and R3 are hydrogen, methyl, or ethyl, 9 provided that at least one of R≥ and R3 is not hydrogen; 10 and where i n RY i s hydrogen or alky 1 of one to 8. carbon 11 atoms inclusive; which comprises reacting an optically 12 active or racemi c compound of the formula 17 wherein R2, -R3, and are as defined above, with a base l8 whose water solution has pH greater th - COHEN ZEDE & SPISBACH
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13334271A | 1971-04-12 | 1971-04-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL39079A0 IL39079A0 (en) | 1972-05-30 |
| IL39079A true IL39079A (en) | 1976-08-31 |
Family
ID=22458141
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL39079A IL39079A (en) | 1971-04-12 | 1972-03-26 | 16-loweralkyl and 16,16-diloweralkyl prostaglandins of the a2,b2,e2,and f2 types and process for making them |
| IL4715172A IL47151A (en) | 1971-04-12 | 1972-03-26 | 5alpha-hydroxy-2beta-(3alpha-(hydroxy or tetrahydropyranyloxy)-trans-1-octenyl)-1alpha-cyclopentane acetic acid or aldehyde ypsilon-lactone or ypsilon-lactol derivatives and their preparation |
| IL4715072A IL47150A (en) | 1971-04-12 | 1972-03-26 | 3alpha-benzoyloxy-5alpha-hydroxy-2beta-(trans-1-octenyl)-1alpha-cyclopentane acetic acid ypsilon-lactone derivatives and process for their preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL4715172A IL47151A (en) | 1971-04-12 | 1972-03-26 | 5alpha-hydroxy-2beta-(3alpha-(hydroxy or tetrahydropyranyloxy)-trans-1-octenyl)-1alpha-cyclopentane acetic acid or aldehyde ypsilon-lactone or ypsilon-lactol derivatives and their preparation |
| IL4715072A IL47150A (en) | 1971-04-12 | 1972-03-26 | 3alpha-benzoyloxy-5alpha-hydroxy-2beta-(trans-1-octenyl)-1alpha-cyclopentane acetic acid ypsilon-lactone derivatives and process for their preparation |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5314551B1 (en) |
| AR (2) | AR194589A1 (en) |
| ES (1) | ES401665A1 (en) |
| FI (1) | FI54293C (en) |
| HU (2) | HU166656B (en) |
| IL (3) | IL39079A (en) |
| NO (3) | NO135936C (en) |
| PH (1) | PH10946A (en) |
| PL (2) | PL96861B1 (en) |
| SU (2) | SU439087A3 (en) |
| ZA (1) | ZA721936B (en) |
-
1972
- 1972-03-21 ZA ZA721936A patent/ZA721936B/en unknown
- 1972-03-26 IL IL39079A patent/IL39079A/en unknown
- 1972-03-26 IL IL4715172A patent/IL47151A/en unknown
- 1972-03-26 IL IL4715072A patent/IL47150A/en unknown
- 1972-04-03 PH PH13409A patent/PH10946A/en unknown
- 1972-04-05 JP JP3358872A patent/JPS5314551B1/ja active Pending
- 1972-04-06 AR AR24133772A patent/AR194589A1/en active
- 1972-04-10 PL PL15464272A patent/PL96861B1/en unknown
- 1972-04-10 PL PL18399072A patent/PL96666B1/en unknown
- 1972-04-11 NO NO122772A patent/NO135936C/no unknown
- 1972-04-11 HU HUUO000081 patent/HU166656B/hu unknown
- 1972-04-11 SU SU1773037A patent/SU439087A3/ru active
- 1972-04-11 ES ES401665A patent/ES401665A1/en not_active Expired
- 1972-04-11 HU HUUO000075 patent/HU165856B/hu unknown
- 1972-04-11 FI FI101772A patent/FI54293C/en active
- 1972-08-21 SU SU721821458A patent/SU628814A3/en active
- 1972-11-27 NO NO434172A patent/NO138252C/en unknown
- 1972-11-27 NO NO434272A patent/NO140423C/en unknown
-
1973
- 1973-02-27 AR AR24682173A patent/AR194784A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| PH10946A (en) | 1977-10-05 |
| NO140423C (en) | 1979-08-29 |
| ZA721936B (en) | 1973-01-31 |
| FI54293B (en) | 1978-07-31 |
| IL47150A (en) | 1976-08-31 |
| SU628814A3 (en) | 1978-10-15 |
| JPS5314551B1 (en) | 1978-05-18 |
| NO135936B (en) | 1977-03-21 |
| ES401665A1 (en) | 1975-03-01 |
| NO135936C (en) | 1977-06-29 |
| SU439087A3 (en) | 1974-08-05 |
| FI54293C (en) | 1978-11-10 |
| AR194784A1 (en) | 1973-08-14 |
| AR194589A1 (en) | 1973-07-31 |
| HU165856B (en) | 1974-11-28 |
| NO140423B (en) | 1979-05-21 |
| IL47151A (en) | 1976-08-31 |
| HU166656B (en) | 1975-04-28 |
| IL39079A0 (en) | 1972-05-30 |
| NO138252C (en) | 1978-08-02 |
| PL96666B1 (en) | 1978-01-31 |
| PL96861B1 (en) | 1978-01-31 |
| NO138252B (en) | 1978-04-24 |
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