CA1064484A - Preparation of 15-methyl-13,14-dihydroprostaglandins in epimerically pure form - Google Patents
Preparation of 15-methyl-13,14-dihydroprostaglandins in epimerically pure formInfo
- Publication number
- CA1064484A CA1064484A CA248,124A CA248124A CA1064484A CA 1064484 A CA1064484 A CA 1064484A CA 248124 A CA248124 A CA 248124A CA 1064484 A CA1064484 A CA 1064484A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- mixture
- reaction product
- methyl
- formula
- 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
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- -1 inclusive Chemical group 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 150000002596 lactones Chemical class 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- 230000001131 transforming effect Effects 0.000 claims 1
- 150000003180 prostaglandins Chemical class 0.000 abstract description 76
- 238000000034 method Methods 0.000 abstract description 62
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract description 28
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- 230000000875 corresponding effect Effects 0.000 description 35
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 30
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- 239000000047 product Substances 0.000 description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
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- 239000008346 aqueous phase Substances 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
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- 239000002599 prostaglandin synthase inhibitor Substances 0.000 description 7
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 7
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- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 238000011176 pooling Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000036584 pressor response Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CBOMORHDRONZRN-QLOYDKTKSA-N prostaglandin E3 Chemical compound CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O CBOMORHDRONZRN-QLOYDKTKSA-N 0.000 description 1
- NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 108700022737 rat Fat1 Proteins 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008085 renal dysfunction Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 206010040560 shock Diseases 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- UNFWWIHTNXNPBV-WXKVUWSESA-N spectinomycin Chemical compound O([C@@H]1[C@@H](NC)[C@@H](O)[C@H]([C@@H]([C@H]1O1)O)NC)[C@]2(O)[C@H]1O[C@H](C)CC2=O UNFWWIHTNXNPBV-WXKVUWSESA-N 0.000 description 1
- 229960000268 spectinomycin Drugs 0.000 description 1
- 230000019100 sperm motility Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 229940064707 sympathomimetics Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- JJPVWQWOOQYHCB-UHFFFAOYSA-N triethyl(phenyl)azanium Chemical compound CC[N+](CC)(CC)C1=CC=CC=C1 JJPVWQWOOQYHCB-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57076975A | 1975-04-23 | 1975-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064484A true CA1064484A (en) | 1979-10-16 |
Family
ID=24280988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA248,124A Expired CA1064484A (en) | 1975-04-23 | 1976-03-17 | Preparation of 15-methyl-13,14-dihydroprostaglandins in epimerically pure form |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS51127066A (hu) |
| BE (1) | BE841056A (hu) |
| CA (1) | CA1064484A (hu) |
| CH (1) | CH614432A5 (hu) |
| DE (1) | DE2613327A1 (hu) |
| FR (2) | FR2308359A1 (hu) |
| GB (1) | GB1494463A (hu) |
| HU (1) | HU175189B (hu) |
| MX (1) | MX3291E (hu) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2134673A1 (en) * | 1971-04-30 | 1972-12-08 | Ono Pharmaceutical Co | Novel optically active isomers of prostaglandin analoguesof natural configuration useful as hypotensive agents, diuretics,contraceptives, for treating gastric ulcer and asthma, and forinhibiting platelet aggregation |
| BE788209A (fr) * | 1971-09-01 | 1973-02-28 | Pfizer | Derives tetrazoyliques des prostaglandines naturelles |
| AR207434A1 (es) * | 1972-06-07 | 1976-10-08 | Pfizer | Procedimiento para preparar carboxamido prostaglandinas n-substituidas |
| US4100355A (en) * | 1972-09-15 | 1978-07-11 | The Upjohn Company | 8β,12α-PGE2 -type compounds |
| US3962312A (en) * | 1972-09-21 | 1976-06-08 | Ono Pharmaceutical Company | 9,11,15-Trihydroxy prost-5-enoic acid analogues |
-
1976
- 1976-03-10 MX MX5976U patent/MX3291E/es unknown
- 1976-03-17 CA CA248,124A patent/CA1064484A/en not_active Expired
- 1976-03-29 DE DE19762613327 patent/DE2613327A1/de not_active Withdrawn
- 1976-03-30 CH CH396476A patent/CH614432A5/xx not_active IP Right Cessation
- 1976-03-31 GB GB1292176A patent/GB1494463A/en not_active Expired
- 1976-04-08 JP JP3883476A patent/JPS51127066A/ja active Pending
- 1976-04-21 HU HU76UO119A patent/HU175189B/hu unknown
- 1976-04-22 FR FR7611899A patent/FR2308359A1/fr active Granted
- 1976-04-23 BE BE166402A patent/BE841056A/xx not_active IP Right Cessation
-
1977
- 1977-02-03 FR FR7703045A patent/FR2348210A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2348210B1 (hu) | 1981-10-02 |
| GB1494463A (en) | 1977-12-07 |
| CH614432A5 (en) | 1979-11-30 |
| FR2348210A1 (fr) | 1977-11-10 |
| AU1260376A (en) | 1977-10-06 |
| MX3291E (es) | 1980-08-22 |
| FR2308359A1 (fr) | 1976-11-19 |
| FR2308359B1 (hu) | 1978-11-17 |
| JPS51127066A (en) | 1976-11-05 |
| BE841056A (fr) | 1976-10-25 |
| HU175189B (hu) | 1980-05-28 |
| DE2613327A1 (de) | 1976-11-04 |
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