GB1331826A - Prostaglandin analogues and the preparation thereof - Google Patents
Prostaglandin analogues and the preparation thereofInfo
- Publication number
- GB1331826A GB1331826A GB5654571A GB5654571A GB1331826A GB 1331826 A GB1331826 A GB 1331826A GB 5654571 A GB5654571 A GB 5654571A GB 5654571 A GB5654571 A GB 5654571A GB 1331826 A GB1331826 A GB 1331826A
- Authority
- GB
- United Kingdom
- Prior art keywords
- endo
- hex
- cis
- compounds
- oxobicyclo
- 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
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- -1 alkyl radicals Chemical group 0.000 abstract 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000002947 alkylene group Chemical group 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- PFCHFHIRKBAQGU-UHFFFAOYSA-N ethyl n-propyl ketone Natural products CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- BOUIVRIDDCHRQT-UHFFFAOYSA-N hexan-3-one Chemical compound [CH2]CC(=O)CCC BOUIVRIDDCHRQT-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003180 prostaglandins Chemical class 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- JAPMJSVZDUYFKL-UHFFFAOYSA-N bicyclo[3.1.0]hexane Chemical class C1CCC2CC21 JAPMJSVZDUYFKL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 150000001718 carbodiimides Chemical class 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- DIRKGCYOYYAJCL-UHFFFAOYSA-N hexan-3-ol Chemical compound [CH2]CCC(O)CC DIRKGCYOYYAJCL-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 abstract 1
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N n-hexan-3-ol Natural products CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 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
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/27—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing six carbon atoms
-
- 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
- C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
-
- 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
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10333870A | 1970-12-31 | 1970-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1331826A true GB1331826A (en) | 1973-09-26 |
Family
ID=22294645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5654571A Expired GB1331826A (en) | 1970-12-31 | 1971-12-06 | Prostaglandin analogues and the preparation thereof |
Country Status (10)
| Country | Link |
|---|---|
| AU (1) | AU460611B2 (sv) |
| BE (1) | BE777612A (sv) |
| CA (1) | CA972356A (sv) |
| CH (1) | CH605726A5 (sv) |
| DE (1) | DE2165184A1 (sv) |
| FR (1) | FR2120163B1 (sv) |
| GB (1) | GB1331826A (sv) |
| NL (1) | NL7118204A (sv) |
| SE (2) | SE397087B (sv) |
| ZA (1) | ZA718157B (sv) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110790737A (zh) * | 2019-11-07 | 2020-02-14 | 河南中烟工业有限责任公司 | 一种2,3-二氢-3,5-二羟基-6-乙基-4h-吡喃-4-酮的制备方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966795A (en) * | 1973-05-21 | 1976-06-29 | The Upjohn Company | 5-Oxa-11-deoxyphenyl- and phenoxy-substituted prostaglandin F1.sub.α analogs |
| US3968144A (en) * | 1973-05-21 | 1976-07-06 | The Upjohn Company | 5-Oxa-11-deoxy phenyl- and phenoxy-substituted prostalandin E1 analogs |
| US3864387A (en) * | 1973-05-21 | 1975-02-04 | Upjohn Co | 5-Oxa phenyl-and phenoxy-substituted prostaglandin F{HD 1{301 {0 {B analogs |
| US3983163A (en) * | 1973-05-21 | 1976-09-28 | The Upjohn Company | 5-Oxa phenyl- and phenoxy-substituted prostaglandin β, analogs |
| US3980694A (en) * | 1974-04-11 | 1976-09-14 | The Upjohn Company | 4-Oxa phenyl-substituted PGA compounds |
| US3983157A (en) * | 1974-04-11 | 1976-09-28 | The Upjohn Company | 4-Oxa phenyl-substituted PGF compounds |
| US3983158A (en) * | 1974-04-11 | 1976-09-28 | The Upjohn Company | 3-Oxa phenyl-substituted PGA compounds |
-
1971
- 1971-12-02 CA CA129,135A patent/CA972356A/en not_active Expired
- 1971-12-06 GB GB5654571A patent/GB1331826A/en not_active Expired
- 1971-12-06 ZA ZA718157A patent/ZA718157B/xx unknown
- 1971-12-09 AU AU36678/71A patent/AU460611B2/en not_active Expired
- 1971-12-27 SE SE7116625A patent/SE397087B/sv unknown
- 1971-12-29 CH CH1916371A patent/CH605726A5/xx not_active IP Right Cessation
- 1971-12-29 DE DE19712165184 patent/DE2165184A1/de not_active Withdrawn
- 1971-12-30 FR FR7147672A patent/FR2120163B1/fr not_active Expired
- 1971-12-31 BE BE777612A patent/BE777612A/xx not_active IP Right Cessation
- 1971-12-31 NL NL7118204A patent/NL7118204A/xx unknown
-
1975
- 1975-02-17 SE SE7501733A patent/SE7501733L/sv unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110790737A (zh) * | 2019-11-07 | 2020-02-14 | 河南中烟工业有限责任公司 | 一种2,3-二氢-3,5-二羟基-6-乙基-4h-吡喃-4-酮的制备方法 |
| CN110790737B (zh) * | 2019-11-07 | 2022-07-22 | 河南中烟工业有限责任公司 | 一种2,3-二氢-3,5-二羟基-6-乙基-4h-吡喃-4-酮的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| SE7501733L (sv) | 1975-02-17 |
| FR2120163A1 (sv) | 1972-08-11 |
| DE2165184A1 (de) | 1972-07-13 |
| CA972356A (en) | 1975-08-05 |
| SE397087B (sv) | 1977-10-17 |
| FR2120163B1 (sv) | 1975-10-10 |
| AU3667871A (en) | 1973-06-14 |
| AU460611B2 (en) | 1975-05-01 |
| NL7118204A (sv) | 1972-07-04 |
| CH605726A5 (sv) | 1978-10-13 |
| ZA718157B (en) | 1972-09-27 |
| BE777612A (fr) | 1972-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |