GB1467813A - Cyclopentane derivatives - Google Patents
Cyclopentane derivativesInfo
- Publication number
- GB1467813A GB1467813A GB2447373A GB2447373A GB1467813A GB 1467813 A GB1467813 A GB 1467813A GB 2447373 A GB2447373 A GB 2447373A GB 2447373 A GB2447373 A GB 2447373A GB 1467813 A GB1467813 A GB 1467813A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- chloro
- compounds
- alkyl
- groups
- 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
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 2
- 150000003180 prostaglandins Chemical class 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 abstract 1
- LQEIHJCPWVRMDQ-UHFFFAOYSA-N 1-butan-2-yloxy-3-chloropropan-2-one Chemical compound CCC(C)OCC(=O)CCl LQEIHJCPWVRMDQ-UHFFFAOYSA-N 0.000 abstract 1
- MBAAZSBVJHIYFR-UHFFFAOYSA-N 1-chloro-3,3-dimethylheptan-2-one Chemical compound CCCCC(C)(C)C(=O)CCl MBAAZSBVJHIYFR-UHFFFAOYSA-N 0.000 abstract 1
- KZHXZSDWLIUHIP-UHFFFAOYSA-N 1-chloro-3-propan-2-yloxypropan-2-one Chemical compound CC(C)OCC(=O)CCl KZHXZSDWLIUHIP-UHFFFAOYSA-N 0.000 abstract 1
- DASDXHZRVCSYEA-UHFFFAOYSA-N 1-chloro-3-propoxypropan-2-one Chemical compound CCCOCC(=O)CCl DASDXHZRVCSYEA-UHFFFAOYSA-N 0.000 abstract 1
- NZMRJUYBKVFDFI-UHFFFAOYSA-N 1-chloro-3-propylhexan-2-one Chemical compound CCCC(CCC)C(=O)CCl NZMRJUYBKVFDFI-UHFFFAOYSA-N 0.000 abstract 1
- BKHLXOAPZZVLIM-UHFFFAOYSA-N 1-chloro-4-ethoxybutan-2-one Chemical compound CCOCCC(=O)CCl BKHLXOAPZZVLIM-UHFFFAOYSA-N 0.000 abstract 1
- RVLHTMZQVHPUPP-UHFFFAOYSA-N 4-(2-chloroethylidene)octane Chemical compound ClCC=C(CCCC)CCC RVLHTMZQVHPUPP-UHFFFAOYSA-N 0.000 abstract 1
- 101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical class OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 abstract 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000005020 hydroxyalkenyl group Chemical group 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 125000005646 oximino group Chemical group 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 239000008016 pharmaceutical coating Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- -1 phosphonium halides Chemical class 0.000 abstract 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000002997 prostaglandinlike Effects 0.000 abstract 1
- 150000003839 salts Chemical class 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1467813 Prostaglandins MAY & BAKER Ltd 17 May 1974 [22 May 1973] 24473/73 Addition to 1398072 Headings C2C and C2P The invention comprises a process for preparing compounds of Formula IX wherein R 1 is C 1-10 alkyl optionally substituted by alkoxy, or C 5-7 cycloalkyl or adamentyl; R 5 is H or alkyl, n is 5 to 8; and A is =C(OR 6 ) 2 or =C=NOR 8 , wherein the symbols R 7 are identical alkyl groups or together form an ethylene linkage optionally substituted by identical alkyl radicals on each chain; and R 8 is alkyl by reacting aldehydes of the Formula III with phosphonates of the formula wherein R 12 is C 1-4 alkyl, in the presence of bases, the conversion of compounds of Formula IX so obtained into compounds of Formula XII by oxidizing the hydroxymethyl groups to carboxy groups, reducing the oxo group in the resulting cyclopentane carboxylic acids to hydroxy groups and converting the acetal or oximino groups A in the resulting (hydroxyalkenyl)cyclopentanealkanoic acids to carbonyl groups by known methods, and certain compounds falling within the scope of Formula I in patent Specification No. 1,398,072 but not specifically described therein. The following intermediates are also prepared: 1 - chloro - 3 - propylheptan - 2 - ene; 1 - chloro- 3,3 - dimethylheptan - 2 - one; 1 - chloro - 3- propoxyacetone; 1 - chloro - 3 - (1 - methylpropoxy)acetone; 1 - chloro - 3 - isopropoxyacetone; 4 - chloroacetylheptane; and 1- chloro-4-ethoxybutan-2-one. Phosphoranes of the formula are prepared reacting compounds of the formula HalCH 2 COR 1 , wherein Hal is Br or Cl with triphenylphosphine followed by reaction of the resulting phosphonium halides with inorganic bases. Phosphonates of the formula are prepared by reacting dimethyl methylphosphonate with esters of the formula wherein R 13 is ethyl. Pharmaceutical compositions, suitable for oral, parenteral, vaginal or rectal administration, contain the above novel prostaglandins or non-toxic salts thereof together with pharmaceutical carriers and coatings. The compounds possess prostaglandin-like pharmacological properties.
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2447373A GB1467813A (en) | 1973-05-22 | 1973-05-22 | Cyclopentane derivatives |
| AU69161/74A AU492967B2 (en) | 1973-05-22 | 1974-05-20 | Cyclopentane derivatives |
| IE1070/74A IE39273B1 (en) | 1973-05-22 | 1974-05-20 | Cyclopentane derivatives |
| ZA00743195A ZA743195B (en) | 1973-05-22 | 1974-05-20 | Cyclopentane derivatives |
| HU74MA2574A HU175493B (en) | 1973-05-22 | 1974-05-20 | Process for producing cyclopentane derivatives |
| CH695674A CH570956A5 (en) | 1973-05-22 | 1974-05-21 | |
| CH416375A CH592621A5 (en) | 1973-05-22 | 1974-05-21 | |
| NL7406842A NL7406842A (en) | 1973-05-22 | 1974-05-21 | |
| FR7417641A FR2230360B2 (en) | 1973-05-22 | 1974-05-21 | |
| CH5776A CH599150A5 (en) | 1973-05-22 | 1974-05-21 | PROCESS FOR THE PREPARATION OF CYCLOPENTANE DERIVATIVES. |
| BE144604A BE815372R (en) | 1973-05-22 | 1974-05-21 | PROCESS FOR THE PREPARATION OF CYCLOPENTANE DERIVATIVES |
| CH416475A CH584674A5 (en) | 1973-05-22 | 1974-05-21 | |
| DE19742424862 DE2424862A1 (en) | 1973-05-22 | 1974-05-22 | CYCLOPENTAN DERIVATIVES |
| CA200,518A CA1039278A (en) | 1973-05-22 | 1974-05-22 | Cyclopentane derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2447373A GB1467813A (en) | 1973-05-22 | 1973-05-22 | Cyclopentane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1467813A true GB1467813A (en) | 1977-03-23 |
Family
ID=10212252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2447373A Expired GB1467813A (en) | 1973-05-22 | 1973-05-22 | Cyclopentane derivatives |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE815372R (en) |
| CA (1) | CA1039278A (en) |
| CH (4) | CH599150A5 (en) |
| DE (1) | DE2424862A1 (en) |
| FR (1) | FR2230360B2 (en) |
| GB (1) | GB1467813A (en) |
| HU (1) | HU175493B (en) |
| IE (1) | IE39273B1 (en) |
| NL (1) | NL7406842A (en) |
| ZA (1) | ZA743195B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1398072A (en) * | 1971-06-14 | 1975-06-18 | May & Baker Ltd | Cyclopentane derivatives |
-
1973
- 1973-05-22 GB GB2447373A patent/GB1467813A/en not_active Expired
-
1974
- 1974-05-20 HU HU74MA2574A patent/HU175493B/en unknown
- 1974-05-20 ZA ZA00743195A patent/ZA743195B/en unknown
- 1974-05-20 IE IE1070/74A patent/IE39273B1/en unknown
- 1974-05-21 FR FR7417641A patent/FR2230360B2/fr not_active Expired
- 1974-05-21 CH CH5776A patent/CH599150A5/en not_active IP Right Cessation
- 1974-05-21 NL NL7406842A patent/NL7406842A/xx not_active Application Discontinuation
- 1974-05-21 CH CH695674A patent/CH570956A5/xx not_active IP Right Cessation
- 1974-05-21 BE BE144604A patent/BE815372R/en active
- 1974-05-21 CH CH416375A patent/CH592621A5/xx not_active IP Right Cessation
- 1974-05-21 CH CH416475A patent/CH584674A5/xx not_active IP Right Cessation
- 1974-05-22 DE DE19742424862 patent/DE2424862A1/en not_active Withdrawn
- 1974-05-22 CA CA200,518A patent/CA1039278A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE39273L (en) | 1974-11-22 |
| ZA743195B (en) | 1975-05-28 |
| CA1039278A (en) | 1978-09-26 |
| CH584674A5 (en) | 1977-02-15 |
| CH592621A5 (en) | 1977-10-31 |
| AU6916174A (en) | 1975-11-20 |
| DE2424862A1 (en) | 1974-12-12 |
| IE39273B1 (en) | 1978-09-13 |
| BE815372R (en) | 1974-11-21 |
| FR2230360A2 (en) | 1974-12-20 |
| CH570956A5 (en) | 1975-12-31 |
| NL7406842A (en) | 1974-11-26 |
| CH599150A5 (en) | 1978-05-12 |
| HU175493B (en) | 1980-08-28 |
| FR2230360B2 (en) | 1979-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |