GB1398340A - Prostaglandins - Google Patents
ProstaglandinsInfo
- Publication number
- GB1398340A GB1398340A GB2682373A GB2682373A GB1398340A GB 1398340 A GB1398340 A GB 1398340A GB 2682373 A GB2682373 A GB 2682373A GB 2682373 A GB2682373 A GB 2682373A GB 1398340 A GB1398340 A GB 1398340A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- cyclopentene
- alkyl
- acyloxy
- yloxy
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 14
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 9
- -1 sulphonyl group Chemical group 0.000 abstract 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- 230000029936 alkylation Effects 0.000 abstract 4
- 238000005804 alkylation reaction Methods 0.000 abstract 4
- 230000003301 hydrolyzing effect Effects 0.000 abstract 4
- PXPYNAJKGKWPAB-UHFFFAOYSA-N 2-(cyclopenten-1-yl)acetaldehyde Chemical class O=CCC1=CCCC1 PXPYNAJKGKWPAB-UHFFFAOYSA-N 0.000 abstract 3
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 230000010933 acylation Effects 0.000 abstract 3
- 238000005917 acylation reaction Methods 0.000 abstract 3
- 125000004423 acyloxy group Chemical group 0.000 abstract 3
- 150000002576 ketones Chemical class 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 238000006264 debenzylation reaction Methods 0.000 abstract 2
- 238000005661 deetherification reaction Methods 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- YURNCBVQZBJDAJ-UHFFFAOYSA-N heptenoic acid group Chemical class C(C=CCCCC)(=O)O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- FLYWBWPHASRCLK-UHFFFAOYSA-N 2-(2-methylcyclopenten-1-yl)acetaldehyde Chemical class CC1=C(CC=O)CCC1 FLYWBWPHASRCLK-UHFFFAOYSA-N 0.000 abstract 1
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 abstract 1
- 101000837626 Homo sapiens Thyroid hormone receptor alpha Proteins 0.000 abstract 1
- 102100028702 Thyroid hormone receptor alpha Human genes 0.000 abstract 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical class NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 abstract 1
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 238000007256 debromination reaction Methods 0.000 abstract 1
- KPSZWAJWFMFMFF-UHFFFAOYSA-N delta-Hexylen-alpha-carbonsaeure Natural products CC=CCCCC(O)=O KPSZWAJWFMFMFF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- PTVJOSBDUWCCNT-UHFFFAOYSA-N methyl 2-(cyclopenten-1-yl)acetate Chemical class COC(=O)CC1=CCCC1 PTVJOSBDUWCCNT-UHFFFAOYSA-N 0.000 abstract 1
- ILSNISVKFYYCCE-UHFFFAOYSA-N methyl 2-cyclopentylacetate Chemical compound COC(=O)CC1CCCC1 ILSNISVKFYYCCE-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- 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
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2567272 | 1972-06-15 | ||
| IT2308673 | 1973-04-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1398340A true GB1398340A (en) | 1975-06-18 |
Family
ID=26328333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2682373A Expired GB1398340A (en) | 1972-06-15 | 1973-06-05 | Prostaglandins |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3862979A (enExample) |
| AU (1) | AU471079B2 (enExample) |
| CA (1) | CA981665A (enExample) |
| CH (2) | CH595340A5 (enExample) |
| DE (1) | DE2330333C2 (enExample) |
| FR (1) | FR2189038B1 (enExample) |
| GB (1) | GB1398340A (enExample) |
| HU (1) | HU170121B (enExample) |
| NL (1) | NL7308384A (enExample) |
| NO (1) | NO142712C (enExample) |
| SE (1) | SE402009B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107226790A (zh) * | 2016-03-25 | 2017-10-03 | 苏州朗科生物技术有限公司 | 一种高纯度他氟前列素及其类似化合物的制备方法及中间体化合物 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996255A (en) * | 1974-04-24 | 1976-12-07 | American Home Products Corporation | Total synthesis of 11-deoxy-15-substituted prostaglandins |
| US3933904A (en) * | 1974-09-13 | 1976-01-20 | American Home Products Corporation | 11,15-Dihydroxy-9,13-prostadienoic acid |
| NL7414650A (nl) * | 1974-11-11 | 1976-05-13 | Akzo Nv | Nieuwe prostaglandine analoga. |
| US3954844A (en) * | 1975-01-03 | 1976-05-04 | G. D. Searle & Co. | (5Z,13E,15S)-15-Hydroxy-11-oxoprosta-5,9.13-trien-1-oic acid and esters |
| AU501803B2 (en) * | 1975-03-21 | 1979-06-28 | Farmitalia Carlo Erba S.P.A. | Fluoro-prostaglandins |
| US4016184A (en) * | 1975-09-17 | 1977-04-05 | The Upjohn Company | 9-Deoxy-9,10-didehydro-PGD1 compounds |
| GB1515986A (en) * | 1976-04-14 | 1978-06-28 | Ici Ltd | Optically active 5-dialkyl-oxymethyl-4-hydroxy-2-cyclopentene-acetic acid derivatives |
| US4238414A (en) * | 1978-02-13 | 1980-12-09 | The Upjohn Company | 2-Decarboxy-2-aminomethyl-6a-carba-PGI2 compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3728382A (en) * | 1970-05-04 | 1973-04-17 | Upjohn Co | 15-methyl and 15-ethyl prostaglandin analogs |
-
1973
- 1973-06-04 US US366978A patent/US3862979A/en not_active Expired - Lifetime
- 1973-06-05 GB GB2682373A patent/GB1398340A/en not_active Expired
- 1973-06-07 AU AU56640/73A patent/AU471079B2/en not_active Expired
- 1973-06-14 CH CH862773A patent/CH595340A5/xx not_active IP Right Cessation
- 1973-06-14 DE DE2330333A patent/DE2330333C2/de not_active Expired
- 1973-06-14 HU HUEA130A patent/HU170121B/hu unknown
- 1973-06-14 CH CH596776A patent/CH583699A5/xx not_active IP Right Cessation
- 1973-06-14 CA CA174,048A patent/CA981665A/en not_active Expired
- 1973-06-14 SE SE7308375A patent/SE402009B/xx unknown
- 1973-06-14 NO NO2483/73A patent/NO142712C/no unknown
- 1973-06-15 FR FR7321866A patent/FR2189038B1/fr not_active Expired
- 1973-06-15 NL NL7308384A patent/NL7308384A/xx not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107226790A (zh) * | 2016-03-25 | 2017-10-03 | 苏州朗科生物技术有限公司 | 一种高纯度他氟前列素及其类似化合物的制备方法及中间体化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US3862979A (en) | 1975-01-28 |
| CA981665A (en) | 1976-01-13 |
| HU170121B (enExample) | 1977-04-28 |
| AU5664073A (en) | 1974-12-12 |
| SE402009B (sv) | 1978-06-12 |
| NO142712C (no) | 1980-10-01 |
| DE2330333C2 (de) | 1982-09-16 |
| AU471079B2 (en) | 1976-04-08 |
| NL7308384A (enExample) | 1973-12-18 |
| DE2330333A1 (de) | 1974-01-17 |
| CH595340A5 (enExample) | 1978-02-15 |
| NO142712B (no) | 1980-06-23 |
| FR2189038A1 (enExample) | 1974-01-25 |
| FR2189038B1 (enExample) | 1976-05-14 |
| CH583699A5 (enExample) | 1977-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |