GB1445628A - Prostaglandin derivatives - Google Patents
Prostaglandin derivativesInfo
- Publication number
- GB1445628A GB1445628A GB4860373A GB4860373A GB1445628A GB 1445628 A GB1445628 A GB 1445628A GB 4860373 A GB4860373 A GB 4860373A GB 4860373 A GB4860373 A GB 4860373A GB 1445628 A GB1445628 A GB 1445628A
- Authority
- GB
- United Kingdom
- Prior art keywords
- octenyl
- trans
- hydroxy
- give
- methyl
- 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
- 150000003180 prostaglandins Chemical class 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- VNZWEESXAVXXCW-UHFFFAOYSA-N 2-[8-(3-hydroxy-3-methyloct-1-enyl)-1,4-dioxaspiro[4.4]nonan-9-yl]heptanoic acid Chemical compound CCCCCC(C(O)=O)C1C(C=CC(C)(O)CCCCC)CCC11OCCO1 VNZWEESXAVXXCW-UHFFFAOYSA-N 0.000 abstract 1
- RSQSULHRRFCMSE-UHFFFAOYSA-N 2-[8-(3-hydroxyoct-1-enyl)-1,4-dioxaspiro[4.4]nonan-9-yl]heptanoic acid Chemical compound CCCCCC(C(O)=O)C1C(C=CC(O)CCCCC)CCC11OCCO1 RSQSULHRRFCMSE-UHFFFAOYSA-N 0.000 abstract 1
- QMWZFIRTVFSKRB-UHFFFAOYSA-N 2-[8-(3-oxooct-1-enyl)-1,4-dioxaspiro[4.4]nonan-9-yl]heptanoic acid Chemical compound CCCCCC(C(O)=O)C1C(C=CC(=O)CCCCC)CCC11OCCO1 QMWZFIRTVFSKRB-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000003182 bronchodilatating effect Effects 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- 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)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1445628 Prostaglandins AMERICAN HOME PRODUCTS CORP 18 Oct 1973 [27 Oct 1972 26 July 1973] 48603/73 Heading C2C Novel compounds I in which R<SP>1</SP> is H, C 1-6 alkyl, alkali metal or a pharmacologically acceptable cation derived from ammonia or from a basic amine and (a) R is C 1-6 alkyl, A is -CH 2 -CH 2 - and B is trans -CH=CH-, or (b) R is methyl, A is cis -CH=CH- and B is trans -CH = CH-, or (c) R is ethynyl, A is -CH 2 CH 2 - and B is -CH 2 -CH 2 -, or (d) R is ethynyl, A is -CH 2 -CH 2 - and B is trans -CH=CH- or (e) R is ethynyl, A is -CH 2 -CH 2 - and B is trans -CH=CH-, are prepared by oxidizing a compound II or deketalizing a compound III in which Z is a ketalized oxo group and, if desired, esterifying or salifying a free acid obtained. 7 - (3 - Hydroxy - 3 - methyl - 1 - octenyl) - 1,4- dioxaspiro[4,4]non - 6 - ylheptanoic acid is prepared by hydrogenating 16-epi-PGA 2 , methyl ester to give 2-[3-hydroxy-1-octenyl)-5-ozo-cyclopentane - heptanoic acid, methyl ester, acetate, reacting this with ethylene glycol to give the corresponding ketal, hydrolysing this to give 7- (3 - hydroxy - 1 - octenyl) - 1,4 - dioxaspiro - [4,4]- non - 6 - yl - heptanoic acid, oxidizing this to give 7 - (3 - oxo - 1 - octenyl) - 1,4 - dioxaspiro- [4,4]non - 6 - yl - heptanoic acid, and reacting this with methyl magnesium bromide to give the desired compound. 2# - [(3RS) - 3 - hydroxy - 3 - methyloctyl] - 5- oxo - 1α - cyclopentane - heptanoic acid is prepared by hydrogenating 2#-[(3RS)-3-hydroxy-3- methyl - trans - 1 - octenyl - 5 - oxo - 1α - cyclopentaneheptanoic acid. Pharmaceutical compositions having bronchodilatory activity comprise a compound I together with a pharmaceutical carrier. The compositions may be in a form suitable for oral (e.g. inhalation) or parenteral administration.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30157172A | 1972-10-27 | 1972-10-27 | |
| US383007A US3922302A (en) | 1973-07-26 | 1973-07-26 | 15-Ethynyl-11-deoxy PGE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1445628A true GB1445628A (en) | 1976-08-11 |
Family
ID=26972455
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB386476A Expired GB1445630A (en) | 1972-10-27 | 1973-10-18 | Prostaglandin derivatives |
| GB4860373A Expired GB1445628A (en) | 1972-10-27 | 1973-10-18 | Prostaglandin derivatives |
| GB386376A Expired GB1445629A (en) | 1972-10-27 | 1973-10-18 | Prostaglandin derivatives |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB386476A Expired GB1445630A (en) | 1972-10-27 | 1973-10-18 | Prostaglandin derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB386376A Expired GB1445629A (en) | 1972-10-27 | 1973-10-18 | Prostaglandin derivatives |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4980043A (en) |
| CA (1) | CA1018970A (en) |
| DE (1) | DE2353788A1 (en) |
| FR (1) | FR2204422B1 (en) |
| GB (3) | GB1445630A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4091015A (en) * | 1972-10-27 | 1978-05-23 | American Home Products Corporation | 15-Substituted prostanoic acids |
| DE2907118A1 (en) * | 1979-02-20 | 1980-09-04 | Schering Ag | NEW PROSTACYCLINE DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3671570A (en) * | 1970-07-30 | 1972-06-20 | Ayerst Mckenna & Harrison | Derivatives of 9-oxo-15-hydroxyprostanoic acid, homologs thereof and their preparation |
| BE794516A (en) * | 1972-01-26 | 1973-05-16 | Wisconsin Alumni Res Found | NEW PROSTAGLANDINS AND THEIR PREPARATION PROCESS |
-
1973
- 1973-10-12 CA CA183,241A patent/CA1018970A/en not_active Expired
- 1973-10-18 GB GB386476A patent/GB1445630A/en not_active Expired
- 1973-10-18 GB GB4860373A patent/GB1445628A/en not_active Expired
- 1973-10-18 GB GB386376A patent/GB1445629A/en not_active Expired
- 1973-10-26 DE DE19732353788 patent/DE2353788A1/en not_active Withdrawn
- 1973-10-26 FR FR7338302A patent/FR2204422B1/fr not_active Expired
- 1973-10-27 JP JP12116473A patent/JPS4980043A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2204422A1 (en) | 1974-05-24 |
| DE2353788A1 (en) | 1974-05-09 |
| GB1445630A (en) | 1976-08-11 |
| GB1445629A (en) | 1976-08-11 |
| FR2204422B1 (en) | 1977-11-10 |
| CA1018970A (en) | 1977-10-11 |
| JPS4980043A (en) | 1974-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 48S | Specification amended (sect. 8/1949) | ||
| SPA | Amended specification published | ||
| PCNP | Patent ceased through non-payment of renewal fee |