CH587283A5 - Omega-norprostaglandins - having prostaglandin like action but having longer lasting and more specific action than PGA, PGE, and PGF - Google Patents
Omega-norprostaglandins - having prostaglandin like action but having longer lasting and more specific action than PGA, PGE, and PGFInfo
- Publication number
- CH587283A5 CH587283A5 CH1525776A CH1525776A CH587283A5 CH 587283 A5 CH587283 A5 CH 587283A5 CH 1525776 A CH1525776 A CH 1525776A CH 1525776 A CH1525776 A CH 1525776A CH 587283 A5 CH587283 A5 CH 587283A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- alkyl
- solution
- dimethyl
- action
- Prior art date
Links
- 230000002045 lasting effect Effects 0.000 title 1
- 230000002997 prostaglandinlike Effects 0.000 title 1
- -1 beta-naphthyl 5-indanyl phenyl Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- 239000000543 intermediate Substances 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000008346 aqueous phase Substances 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012213 gelatinous substance Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- INDCQOTULGRLGI-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-2-dimethoxyphosphorylethanone Chemical compound C1=CC=C2CC(C(=O)CP(=O)(OC)OC)CC2=C1 INDCQOTULGRLGI-UHFFFAOYSA-N 0.000 description 2
- JZFOBTPKPKPPSX-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-3-dimethoxyphosphorylpropan-2-one Chemical compound C1=CC=C2CC(CC(=O)CP(=O)(OC)OC)CC2=C1 JZFOBTPKPKPPSX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- MKDXSYRVLJNDHN-UHFFFAOYSA-N (7-cyclopentyl-2-oxoheptyl)phosphonic acid Chemical compound OP(O)(=O)CC(=O)CCCCCC1CCCC1 MKDXSYRVLJNDHN-UHFFFAOYSA-N 0.000 description 1
- WXJAIFNXTBIJBL-UHFFFAOYSA-N 1-cyclodecyl-2-dimethoxyphosphorylethanone Chemical compound COP(=O)(OC)CC(=O)C1CCCCCCCCC1 WXJAIFNXTBIJBL-UHFFFAOYSA-N 0.000 description 1
- NWPRXAIYBULIEI-UHFFFAOYSA-N 2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid Chemical compound COC(=O)NC(C(O)=O)C(C)(C)C NWPRXAIYBULIEI-UHFFFAOYSA-N 0.000 description 1
- BBHJTCADCKZYSO-UHFFFAOYSA-N 4-(4-ethylcyclohexyl)benzonitrile Chemical compound C1CC(CC)CCC1C1=CC=C(C#N)C=C1 BBHJTCADCKZYSO-UHFFFAOYSA-N 0.000 description 1
- XVKSUXNSSZCHMC-UHFFFAOYSA-N 6-cyclopropyl-1-dimethoxyphosphorylhexan-2-one Chemical compound COP(=O)(OC)CC(=O)CCCCC1CC1 XVKSUXNSSZCHMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- BWGYNDFMGAWDHP-UHFFFAOYSA-N ethyl 2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=CC=C2CC(C(=O)OCC)CC2=C1 BWGYNDFMGAWDHP-UHFFFAOYSA-N 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- RMOPJLIMRSAIMD-UHFFFAOYSA-N methyl 2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=CC=C2CC(C(=O)OC)CC2=C1 RMOPJLIMRSAIMD-UHFFFAOYSA-N 0.000 description 1
- ITYDRDKUXNKSAY-UHFFFAOYSA-N methyl 2-(2,3-dihydro-1h-inden-2-yl)acetate Chemical compound C1=CC=C2CC(CC(=O)OC)CC2=C1 ITYDRDKUXNKSAY-UHFFFAOYSA-N 0.000 description 1
- ASKFJDVCNKIXFI-UHFFFAOYSA-N methyl 6-cyclopentylhexanoate Chemical compound COC(=O)CCCCCC1CCCC1 ASKFJDVCNKIXFI-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- XPQPWPZFBULGKT-UHFFFAOYSA-N methyl undecanoate Chemical compound CCCCCCCCCCC(=O)OC XPQPWPZFBULGKT-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 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
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/34—Unsaturated compounds containing ether groups, groups, groups, or 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
- 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
- C07F9/4018—Esters of cycloaliphatic acids
-
- 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
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30475072A | 1972-11-08 | 1972-11-08 | |
| CH1570773A CH593930A5 (enrdf_load_stackoverflow) | 1972-11-08 | 1973-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH587283A5 true CH587283A5 (en) | 1977-04-29 |
Family
ID=25716890
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1525776A CH587283A5 (en) | 1972-11-08 | 1973-11-08 | Omega-norprostaglandins - having prostaglandin like action but having longer lasting and more specific action than PGA, PGE, and PGF |
| CH1525676A CH593933A5 (enrdf_load_stackoverflow) | 1972-11-08 | 1973-11-08 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1525676A CH593933A5 (enrdf_load_stackoverflow) | 1972-11-08 | 1973-11-08 |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH587283A5 (enrdf_load_stackoverflow) |
-
1973
- 1973-11-08 CH CH1525776A patent/CH587283A5/fr not_active IP Right Cessation
- 1973-11-08 CH CH1525676A patent/CH593933A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH593933A5 (enrdf_load_stackoverflow) | 1977-12-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0729936B1 (fr) | Procédé de synthèse d'acides acryliques alpha-substitués et N-(mercaptoacyl) amino acides | |
| EP0378825B1 (fr) | Esters alicycliques et leur utilisation à titre d'ingrédients parfumants | |
| CH587283A5 (en) | Omega-norprostaglandins - having prostaglandin like action but having longer lasting and more specific action than PGA, PGE, and PGF | |
| FR2505820A1 (fr) | Procede de preparation de derives de (7e-9z)-alcadienols | |
| US4298757A (en) | 2-[2-(2,2-Dihalovinyl)-3,3-dimethylcyclopropyl ]vinyl alkanoates | |
| CH626319A5 (en) | Process for the preparation of lower alkyl esters of racemic trans-2,2-disubstituted-1,3-cyclopropanedicarboxylic acids | |
| EP0153212B1 (fr) | Nouveaux dérivés de la 4,4-diméthyl tétrahydro-2H-pyran-2-one, leur procédé de préparation et leur application à la synthèse de dérivés cyclopropaniques | |
| EP0094304B1 (fr) | Nouveau procédé de préparation de dérivés de l'acide cyclopropane carboxylique et nouveaux intermédiaires | |
| FR2478084A1 (fr) | Nouveaux esters de l'acide tricyclo(5.2.1.02,6)decane-2-carboxylique, leurs procedes de preparation et leur utilisation en parfumerie | |
| JPS647978B2 (enrdf_load_stackoverflow) | ||
| CA1078860A (fr) | Procedes de synthese de derives de prostaglandines | |
| CH650770A5 (fr) | Procedes de preparation de derives d'acides cyclopropane carboxyliques porteurs d'une fonction aldehyde. | |
| EP0433267A2 (fr) | Préparation de l'acide éicosatétraynoique | |
| FR2590259A1 (fr) | Procede de preparation de derives fluores de l'acide phosphonique, et produits obtenus par la mise en oeuvre de ce procede | |
| EP0032713B1 (fr) | Nouveaux sels de phosphonium, procédé pour leur préparation et leur utilisation à titre de produits de départ pour la préparation de composés bicycliques insaturés | |
| EP0277052B1 (fr) | Dérivés de la 4,4-diméthyl tétrahydropyr-2-one, leur procédé de préparation et leur application à la synthèse de produits pyréthrinoides | |
| US3989729A (en) | Synthesis of 8-oxo-4-cis-octenoic acid ester | |
| CA2031241A1 (fr) | Intermediaires, leurs procedes de preparation et leur utilisation pour la synthese des vitamines a et e | |
| US4249015A (en) | Preparation of organic acids and/or esters | |
| FR2565968A1 (fr) | Procede d'obtention d'intermediaires de la preparation de pyrethroides | |
| FR2580644A1 (fr) | Derives de l'acide ascorbique | |
| JPH0840971A (ja) | ヒノキチオール及びその中間生成物の製造方法 | |
| FR2499979A1 (fr) | Procede d'epimerisation d'acides trans chrysanthemiques | |
| EP0579991A2 (fr) | Procédé pour la préparation d'une cétone bicyclique décalinique | |
| EP0333373A2 (en) | Method for synthesizing acyloxycarboxylic acids |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |