ES395814A1 - Cyclopentane derivatives - Google Patents
Cyclopentane derivativesInfo
- Publication number
- ES395814A1 ES395814A1 ES395814A ES395814A ES395814A1 ES 395814 A1 ES395814 A1 ES 395814A1 ES 395814 A ES395814 A ES 395814A ES 395814 A ES395814 A ES 395814A ES 395814 A1 ES395814 A1 ES 395814A1
- Authority
- ES
- Spain
- Prior art keywords
- radical
- carbon atoms
- formula
- substituent
- hydroxy
- 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
- -1 alkylamino radical Chemical class 0.000 abstract 13
- 125000004432 carbon atom Chemical group C* 0.000 abstract 11
- 150000001875 compounds Chemical class 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 abstract 1
- CPVNCBJFUQQXSU-UHFFFAOYSA-N 5-triphenylphosphaniumylpentanoate Chemical class C1(=CC=CC=C1)[P+](CCCCC(=O)[O-])(C1=CC=CC=C1)C1=CC=CC=C1 CPVNCBJFUQQXSU-UHFFFAOYSA-N 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 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
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 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
-
- 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
- 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
-
- 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
- C07F9/4015—Esters of acyclic unsaturated acids
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Procedure for obtaining prostanoic acid derivatives, of general formula: **(See formula)** in which R1 is a hydroxy radical, an amino radical, an alkylamino radical that can have up to 6 carbon atoms, an alkoxy radical of 1 to 6 carbon atoms or an alkoxy radical of 2 to 3 carbon atoms that has as its substituent a β- or γ -diakylamino radical, where each alkyl radical has from 1 to 4 carbon atoms, a β- or γ -pirrodilino, piperidino or morpholino radical; R2 is a hydrogen atom, or R2 and R3 together form the oxo radical; R4 is an n-hexyl radical bearing a straight chain alkyl substituent with 1 to 4 carbon atoms on any of the carbon atoms 1 to 5 of the hexyl radical, or a methyl, ethyl, methylene, ethylidene or vinyl substituent, or one methyl and one methylated substituent, or two methyl substituents on carbon atom 6 of the n-hexyl radical; and A is an ethylene or vinylene radical; and in those compounds where R1 is a hydroxy radical, the base addition salts acceptable for pharmaceutical uses thereof, characterized in that it comprises: (a) the hydrolysis of a compound of the formula: **(See formula)** or a mixed anhydride thereof, where R1 has the meaning indicated above, R2 is a hydroxy radical, an alkanoyloxy radical of 1 to 4 carbon atoms or a tetrahydropyran-2-yloxy radical and R3 is a hydrogen atom, or R2 and R3 together form the oxo radical, A and R4 have the meanings above, and R5 and R6 are each a tetrahydropyran-2-yloxy radical, or an acyloxy radical of 1 to 6 carbon atoms; or (b) In those compounds where R1 is an alkoxy radical of 1 to 6 carbon atoms, the reaction of an acid of the formula: **(See formula)** where A, R2, R3 and R4 have the meanings indicated above, with a diazoalkane of the formula R7.N2, where R7 is an alkyl radical of 1 to 6 carbon atoms; or (c) the reaction of a lactol of the formula: **(See formula)** with a (4-carboxybutyl) triphenylphosphonium salt, where A and R4 have the meanings indicated above; after which, when a salt of a compound in which R1 is a hydroxy radical is needed, the carboxylic acid is reacted with a base. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB48131/70*2A GB1356581A (en) | 1970-10-09 | 1970-10-09 | Cyclopentane derivatives |
| GB181471 | 1971-01-14 | ||
| GB554371 | 1971-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES395814A1 true ES395814A1 (en) | 1975-03-01 |
Family
ID=27253947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES395814A Expired ES395814A1 (en) | 1970-10-09 | 1971-10-07 | Cyclopentane derivatives |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE773728A (en) |
| DE (1) | DE2150361A1 (en) |
| ES (1) | ES395814A1 (en) |
| FR (1) | FR2110335B1 (en) |
| GB (1) | GB1356581A (en) |
| HU (1) | HU163414B (en) |
| IL (1) | IL37821A0 (en) |
| NL (1) | NL7113880A (en) |
| SU (1) | SU439962A3 (en) |
| ZM (1) | ZM14271A1 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3887587A (en) * | 1972-04-17 | 1975-06-03 | Pfizer | Synthesis of prostaglandins of the one-series |
| DE2317019A1 (en) * | 1972-04-27 | 1973-11-08 | Upjohn Co | NEW 4,5 DIDEHYDRO PROSTAGLANDIN |
| US3954741A (en) * | 1972-06-07 | 1976-05-04 | Pfizer Inc. | N-substituted prostaglandin carboxamides |
| GB1520522A (en) * | 1975-06-16 | 1978-08-09 | Ono Pharmaceutical Co | 16-methyleneprostaglandins |
| US5236907A (en) * | 1988-10-01 | 1993-08-17 | R-Tech Ueno Ltd. | Ocular hypotensive agents |
| US6420422B1 (en) | 1987-09-18 | 2002-07-16 | Sucampo Pharmaceuticals, Inc. | Ocular hypotensive agents |
| US5194429A (en) * | 1988-10-01 | 1993-03-16 | K.K. Ueno Seiyaku Oyo Kenkyujo | Ocular hypotensive agents |
| DE68918391T2 (en) * | 1988-10-01 | 1995-01-19 | Ueno Seiyaku Oyo Kenkyujo Kk | Eyepieces hypotensive means. |
| EP2084124B9 (en) | 2006-10-02 | 2015-07-01 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of prostaglandins and related compounds with very high skin penetration rates |
| JP6030168B2 (en) * | 2015-03-09 | 2016-11-24 | テックフィールズ バイオケム カンパニー リミテッド | Positively charged water-soluble prodrugs of prostaglandins and related compounds with very high skin permeability |
| JP6306067B2 (en) * | 2016-01-08 | 2018-04-04 | テックフィールズ バイオケム カンパニー リミテッド | Positively charged water-soluble prodrugs of prostaglandins and related compounds with very high skin permeability |
| JP7141025B1 (en) * | 2021-11-11 | 2022-09-22 | エルデシエロ プライベート リミテッド | Compounds, compositions, methods, and methods of manufacture |
-
1970
- 1970-10-09 GB GB48131/70*2A patent/GB1356581A/en not_active Expired
-
1971
- 1971-09-21 HU HUIE478A patent/HU163414B/hu unknown
- 1971-09-28 IL IL37821A patent/IL37821A0/en unknown
- 1971-10-01 ZM ZM142/71A patent/ZM14271A1/en unknown
- 1971-10-04 SU SU1702653A patent/SU439962A3/en active
- 1971-10-07 ES ES395814A patent/ES395814A1/en not_active Expired
- 1971-10-08 DE DE19712150361 patent/DE2150361A1/en active Pending
- 1971-10-08 BE BE773728A patent/BE773728A/en unknown
- 1971-10-08 NL NL7113880A patent/NL7113880A/xx unknown
- 1971-10-08 FR FR7136366A patent/FR2110335B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE773728A (en) | 1972-04-10 |
| ZM14271A1 (en) | 1972-06-21 |
| FR2110335B1 (en) | 1975-06-06 |
| NL7113880A (en) | 1972-04-11 |
| DE2150361A1 (en) | 1972-04-13 |
| GB1356581A (en) | 1974-06-12 |
| IL37821A0 (en) | 1971-11-29 |
| HU163414B (en) | 1973-08-28 |
| SU439962A3 (en) | 1974-08-15 |
| FR2110335A1 (en) | 1972-06-02 |
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