FR2294696A1 - Oxa-prostaglandin analogues - prepd. by deprotection of tetrahydropyranyloxy-substd. derivs. (BE220676) - Google Patents
Oxa-prostaglandin analogues - prepd. by deprotection of tetrahydropyranyloxy-substd. derivs. (BE220676)Info
- Publication number
- FR2294696A1 FR2294696A1 FR7539194A FR7539194A FR2294696A1 FR 2294696 A1 FR2294696 A1 FR 2294696A1 FR 7539194 A FR7539194 A FR 7539194A FR 7539194 A FR7539194 A FR 7539194A FR 2294696 A1 FR2294696 A1 FR 2294696A1
- Authority
- FR
- France
- Prior art keywords
- substd
- alkyl
- opt
- tri
- mono
- 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.)
- Granted
Links
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 title abstract 2
- 238000010511 deprotection reaction Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 239000003433 contraceptive agent Substances 0.000 abstract 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 239000004015 abortifacient agent Substances 0.000 abstract 1
- 231100000641 abortifacient agent Toxicity 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 230000001088 anti-asthma Effects 0.000 abstract 1
- 230000002785 anti-thrombosis Effects 0.000 abstract 1
- 230000000767 anti-ulcer Effects 0.000 abstract 1
- 239000003146 anticoagulant agent Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940124558 contraceptive agent Drugs 0.000 abstract 1
- 230000002254 contraceptive effect Effects 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000012173 estrus Effects 0.000 abstract 1
- 230000002496 gastric effect Effects 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 230000001939 inductive effect Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000028327 secretion Effects 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Furan Compounds (AREA)
Abstract
Prostaglandin analogues of formula (I) in the natural, optically active configuration or as racemic cpds.: (where R1 + R2 is O, or one of R1 and R2 is H and the other is OH; one of R3 and R4 is H and the other is OH; is 1-5C straight or branched alkyl, or phenyl or benzyl opt. mono- di- or tri-substd. in the nucleus by halogen, CF3, OH, 1-4C alkyl and/or 1-4C alkoxy; R5, when X is 1-5C alkyl, is a diphenyl ether gp. opt. mono- di- or tri-substd. in either or both nuclei by halogen, CF3, OH, 1-4C alkyl and/or 1-4C alkoxy or a phenoxy-(2-5 C straight chain or 3-6C branched chain alkyl) opt. mono-di- or tri-substd. in the nucleus by halogen, CF3, OH, 1-4C alkyl and/or 1-4C alkoxy, or, when X is opt. substd. phenyl, a benzyl residue opt. mono- di- or tri-substd. in the nucleus by halogen, CF3, OH, 1-4C alkyl and/or 1-4C alkoxy, or, when X is opt. substd. benzyl, a phenyl residue opt. mono-, di- or tri-substd. by halogen, CF3, OH, 1-4C alkyl and/or 1-4C alkoxy; and the C-atoms in the 5- and 6-positions and the 13- and 14-positions are all linked by single bonds or all linked by double bonds), e.g. 9-oxo-11 alpha, 15-dihydroxy-16-methyl-16-(3-chloro-4-(4-chlorophenoxy)-phenoxy)-- 5-cis-13-trans-tetranorprostadienoci acid, their physiologically tolerable salts with organic and inorganic bases, and their esters with 1-8C aliphatic, cycloaliphatic and araliphatic alcohols are new. (I) can be used as pharmaceuticals with hypotensive, diuretic, antithrombotic labour-inducing, abortifacient, contraceptive, gastric secretion inhibiting, antiulcer and antiasthmatic activity. They are particularly useful as contraceptives for use in humans and as agents for synchronising oestrus in various animal species. They are more potent and longer-acting than natural prostaglandins.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742460990 DE2460990A1 (en) | 1974-12-21 | 1974-12-21 | NEW PROSTAGLANDIN ANALOGS AND PROCEDURES FOR THEIR PRODUCTION |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2294696A1 true FR2294696A1 (en) | 1976-07-16 |
| FR2294696B1 FR2294696B1 (en) | 1978-07-28 |
Family
ID=5934352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7539194A Granted FR2294696A1 (en) | 1974-12-21 | 1975-12-19 | Oxa-prostaglandin analogues - prepd. by deprotection of tetrahydropyranyloxy-substd. derivs. (BE220676) |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5186449A (en) |
| AU (1) | AU8772775A (en) |
| BE (1) | BE836950A (en) |
| DE (1) | DE2460990A1 (en) |
| DK (1) | DK581075A (en) |
| ES (1) | ES443524A1 (en) |
| FR (1) | FR2294696A1 (en) |
| LU (1) | LU74076A1 (en) |
| NL (1) | NL7514654A (en) |
| SE (1) | SE7514447L (en) |
| ZA (1) | ZA757872B (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4212985A (en) * | 1978-04-28 | 1980-07-15 | The Upjohn Company | cis-4,5-Didehydro-16-phenoxy-PGE1 compounds |
| EP1012137B1 (en) * | 1997-09-09 | 2002-11-06 | The Procter & Gamble Company | Aromatic c16-c20-substituted tetrahydro prostaglandins useful as fp agonists |
| US5977173A (en) * | 1997-09-09 | 1999-11-02 | Wos; John August | Aromatic C16 -C20 -substituted tetrahydro prostaglandins useful as FP agonists |
| DE69832513T2 (en) * | 1997-09-09 | 2006-07-13 | Duke University | AROMATIC C16-C20 SUBSTITUTED TETRAHYDRO PROSTAGLANDINES USE AS FP AGONISTE |
| US6444840B1 (en) | 1998-03-31 | 2002-09-03 | The Procter & Gamble Co. | C11 oxymyl and hydroxylamino prostaglandins useful as FP agonists |
| ES2223180T3 (en) | 1998-03-31 | 2005-02-16 | Duke University | OXIMETABLE C11 PROSTAGLANDINAS AND HYDROXYLAMINE USED AS MEDICINES. |
| NZ513825A (en) | 1999-03-05 | 2001-09-28 | Procter & Gamble | C 16 unsaturated FP-selective prostaglandins analogs |
| US6894175B1 (en) | 1999-08-04 | 2005-05-17 | The Procter & Gamble Company | 2-Decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use |
| US20020037914A1 (en) | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| US20020172693A1 (en) | 2000-03-31 | 2002-11-21 | Delong Michell Anthony | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US20020013294A1 (en) | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
| US8722739B2 (en) | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US8623918B2 (en) | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| CA3045407C (en) | 2009-07-29 | 2024-03-12 | Elise A. Olsen | Compositions and methods for inhibiting hair growth |
-
1974
- 1974-12-21 DE DE19742460990 patent/DE2460990A1/en active Pending
-
1975
- 1975-12-16 ES ES443524A patent/ES443524A1/en not_active Expired
- 1975-12-16 NL NL7514654A patent/NL7514654A/en unknown
- 1975-12-19 AU AU87727/75A patent/AU8772775A/en not_active Expired
- 1975-12-19 JP JP50150665A patent/JPS5186449A/ja active Pending
- 1975-12-19 FR FR7539194A patent/FR2294696A1/en active Granted
- 1975-12-19 LU LU74076A patent/LU74076A1/xx unknown
- 1975-12-19 ZA ZA757872A patent/ZA757872B/en unknown
- 1975-12-19 SE SE7514447A patent/SE7514447L/en unknown
- 1975-12-19 DK DK581075A patent/DK581075A/en unknown
- 1975-12-22 BE BE163013A patent/BE836950A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU8772775A (en) | 1977-06-23 |
| SE7514447L (en) | 1976-06-22 |
| LU74076A1 (en) | 1976-11-11 |
| DK581075A (en) | 1976-06-22 |
| JPS5186449A (en) | 1976-07-29 |
| ZA757872B (en) | 1976-11-24 |
| FR2294696B1 (en) | 1978-07-28 |
| BE836950A (en) | 1976-06-22 |
| NL7514654A (en) | 1976-06-23 |
| DE2460990A1 (en) | 1976-07-01 |
| ES443524A1 (en) | 1977-05-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2294696A1 (en) | Oxa-prostaglandin analogues - prepd. by deprotection of tetrahydropyranyloxy-substd. derivs. (BE220676) | |
| Kirtland et al. | Prostaglandin E1 may act as a “calcium ionophore” | |
| IT1121462B (en) | DL 9 KETO ACID DERIVATIVES TRIENOIC PROSTA PARTICULARLY USEFUL AS MEDICATIONS AND PROCEDURE FOR THEIR PREPARATION | |
| ES8604179A1 (en) | Thiazolidine derivatives, process for the preparation and pharmaceutical compositions thereof | |
| ES449162A1 (en) | 16-Phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives | |
| GB1458315A (en) | Prostanoic acid derivatives | |
| US4089951A (en) | Oestrus or menstrual regulation | |
| US3829579A (en) | Stable solutions of pge-type compounds | |
| FR2399999A1 (en) | Prostane derivs. - useful as contraceptives or for control of the oestrus cycle in animals | |
| ES8201531A1 (en) | Alcoxy-propanol amines useful as medicines, and process for their preparation. | |
| IT1059533B (en) | Tricyclic chromone-2-carboxylic acid derivs - with anti-allergic activity (BE280576) | |
| ES531131A0 (en) | A PROCEDURE FOR PREPARING ACID 5R, 6S, 8R-6- (1-HYDROXYETHYL) -2- (2-CARBAMOYLOXYETHYLTIO) -PENEM-3-CARBOXYLLIC | |
| SE8104703L (en) | HETERO-PROSTAGLAND INGREDIENTS AND PROCEDURES FOR PRODUCING THEREOF | |
| GB1388041A (en) | Benzimidazolyl sulphides and sulphones | |
| GB1389069A (en) | Prostaglandins and the preparation thereof | |
| IT1075678B (en) | 6,9-Oxido prostaglandin analogues - useful as antihypertensives, vasodilators, thrombocyte aggregation inhibitors, etc. | |
| IT1072541B (en) | 6,9-Oxido prostaglandin analogues - useful as antihypertensives, vasodilators, thrombocyte aggregation inhibitors, etc. | |
| GB1464206A (en) | ||
| PT71891A (en) | Process for the preparation of new 16-methoxy-16-methyl-prostaglandin e1 derivatives useful as gastroprotective agents | |
| IT1120412B (en) | Thia-analogues of prostaglandins - prepd e.g. by reacting 1-(carboxyalkyl)-1-cyclopentenes with thio cpds (SW081275 | |
| GB736371A (en) | Improvements in or relating to methods of producing stable aqueous solutions containing vitamin b | |
| ES8604507A1 (en) | Prostaglandins, their preparation and pharmaceutical compositions. | |
| ES8406488A3 (en) | Norescopolamine derivs. for pharmaceutical use | |
| IT1065450B (en) | Novel optically active prostaglandin or its racemate orsalt, useful for providing luteolytic, abortifacient andlabor-inducing activity, controlling reproductive cycle inovulating female mammals and controlling gastric secretion | |
| JPS58121268A (en) | 9-brom-prostaglandin derivative, manufacture and medicine containing same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |