IL42425A - 13-cis-prostaglandin derivatives of the pge1 and pgf1 series and their preparation - Google Patents
13-cis-prostaglandin derivatives of the pge1 and pgf1 series and their preparationInfo
- Publication number
- IL42425A IL42425A IL42425A IL4242573A IL42425A IL 42425 A IL42425 A IL 42425A IL 42425 A IL42425 A IL 42425A IL 4242573 A IL4242573 A IL 4242573A IL 42425 A IL42425 A IL 42425A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- cis
- group
- lithium
- octen
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims 35
- 150000001875 compounds Chemical class 0.000 claims 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 31
- 238000000034 method Methods 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 14
- 239000002253 acid Chemical group 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 239000003153 chemical reaction reagent Substances 0.000 claims 9
- 229910052744 lithium Inorganic materials 0.000 claims 9
- -1 prostaglandin compound Chemical class 0.000 claims 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 7
- 238000002844 melting Methods 0.000 claims 7
- 230000008018 melting Effects 0.000 claims 7
- 239000002904 solvent Substances 0.000 claims 7
- CZWNWBUDJIIZHU-UHFFFAOYSA-N 1-iodooct-1-en-1-ol Chemical compound CCCCCCC=C(O)I CZWNWBUDJIIZHU-UHFFFAOYSA-N 0.000 claims 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 5
- 239000010949 copper Substances 0.000 claims 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052802 copper Inorganic materials 0.000 claims 4
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 claims 4
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims 4
- KQDYMAYUKUZGDA-NFXKFNAJSA-N (z,3r)-1-iodooct-1-en-3-ol Chemical compound CCCCC[C@@H](O)\C=C/I KQDYMAYUKUZGDA-NFXKFNAJSA-N 0.000 claims 3
- KQDYMAYUKUZGDA-UAPHAKCISA-N (z,3s)-1-iodooct-1-en-3-ol Chemical compound CCCCC[C@H](O)\C=C/I KQDYMAYUKUZGDA-UAPHAKCISA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000002170 ethers Chemical class 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 claims 3
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- OPHUWKNKFYBPDR-UHFFFAOYSA-N copper lithium Chemical compound [Li].[Cu] OPHUWKNKFYBPDR-UHFFFAOYSA-N 0.000 claims 2
- 125000001033 ether group Chemical group 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 claims 2
- 230000000536 complexating effect Effects 0.000 claims 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 150000002527 isonitriles Chemical class 0.000 claims 1
- MLEBCSIXQCGXGO-UHFFFAOYSA-N lithium;copper(1+) Chemical compound [Li+].[Cu+] MLEBCSIXQCGXGO-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- VSMOENVRRABVKN-UHFFFAOYSA-N oct-1-en-3-ol Chemical compound CCCCCC(O)C=C VSMOENVRRABVKN-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000003791 organic solvent mixture Substances 0.000 claims 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims 1
- 150000003180 prostaglandins Chemical class 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical group CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 claims 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 claims 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 claims 1
- DAGQYUCAQQEEJD-UHFFFAOYSA-N tris(2-methylpropyl)phosphane Chemical compound CC(C)CP(CC(C)C)CC(C)C DAGQYUCAQQEEJD-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
- C12N9/20—Triglyceride splitting, e.g. by means of lipase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P31/00—Preparation of compounds containing a five-membered ring having two side-chains in ortho position to each other, and having at least one oxygen atom directly bound to the ring in ortho position to one of the side-chains, one side-chain containing, not directly bound 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 at least one oxygen atom bound in gamma-position to the ring, e.g. prostaglandins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US272880A US3867377A (en) | 1972-07-18 | 1972-07-18 | Method of making 13-cis prostaglandin derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42425A0 IL42425A0 (en) | 1973-08-29 |
| IL42425A true IL42425A (en) | 1976-09-30 |
Family
ID=23041674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42425A IL42425A (en) | 1972-07-18 | 1973-06-01 | 13-cis-prostaglandin derivatives of the pge1 and pgf1 series and their preparation |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3867377A (th) |
| JP (1) | JPS4992027A (th) |
| AT (1) | AT341688B (th) |
| AU (1) | AU474934B2 (th) |
| BE (2) | BE802386A (th) |
| CA (1) | CA1038378A (th) |
| CH (1) | CH592620A5 (th) |
| DE (2) | DE2357571A1 (th) |
| ES (1) | ES416998A1 (th) |
| FR (2) | FR2192830B1 (th) |
| GB (1) | GB1430995A (th) |
| IL (1) | IL42425A (th) |
| NL (1) | NL7310007A (th) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4110368A (en) * | 1972-07-24 | 1978-08-29 | American Cyanamid Company | Hydro substituted prostanoic acids and esters |
| US3998852A (en) * | 1973-04-16 | 1976-12-21 | Syntex (U.S.A.) Inc. | Novel prostaglandin intermediates and process for the production thereof |
| US4055564A (en) * | 1975-01-15 | 1977-10-25 | Syntex (U.S.A.) Inc. | Novel prostaglandin intermediates and process for the production thereof |
| US4026909A (en) * | 1975-07-14 | 1977-05-31 | The Upjohn Company | Cis-13-PGF2.sub.α analogs |
| FR2353287A1 (fr) * | 1975-08-29 | 1977-12-30 | Roussel Uclaf | Nouveaux derives du cyclopentanol, leur procede de preparation et leur application comme medicaments |
-
1972
- 1972-07-18 US US272880A patent/US3867377A/en not_active Expired - Lifetime
-
1973
- 1973-05-29 CA CA172,898A patent/CA1038378A/en not_active Expired
- 1973-06-01 IL IL42425A patent/IL42425A/en unknown
- 1973-06-12 GB GB2799873A patent/GB1430995A/en not_active Expired
- 1973-06-14 AU AU56904/73A patent/AU474934B2/en not_active Expired
- 1973-07-09 DE DE2357571*A patent/DE2357571A1/de active Pending
- 1973-07-09 DE DE19732334764 patent/DE2334764A1/de active Pending
- 1973-07-13 FR FR7325794A patent/FR2192830B1/fr not_active Expired
- 1973-07-16 BE BE133514A patent/BE802386A/xx unknown
- 1973-07-16 BE BE133513A patent/BE802385A/xx unknown
- 1973-07-17 JP JP48082451A patent/JPS4992027A/ja active Pending
- 1973-07-17 ES ES416998A patent/ES416998A1/es not_active Expired
- 1973-07-18 CH CH1052673A patent/CH592620A5/xx not_active IP Right Cessation
- 1973-07-18 AT AT632673A patent/AT341688B/de not_active IP Right Cessation
- 1973-07-18 NL NL7310007A patent/NL7310007A/xx not_active Application Discontinuation
-
1975
- 1975-04-25 FR FR7513144A patent/FR2283118A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IL42425A0 (en) | 1973-08-29 |
| ATA632673A (de) | 1977-06-15 |
| ES416998A1 (es) | 1976-06-16 |
| US3867377A (en) | 1975-02-18 |
| FR2283118B1 (th) | 1979-07-27 |
| AU5690473A (en) | 1974-12-19 |
| BE802386A (fr) | 1974-01-16 |
| JPS4992027A (th) | 1974-09-03 |
| AT341688B (de) | 1978-02-27 |
| BE802385A (fr) | 1974-01-16 |
| DE2334764A1 (de) | 1974-02-14 |
| FR2283118A1 (fr) | 1976-03-26 |
| GB1430995A (en) | 1976-04-07 |
| DE2357571A1 (de) | 1974-10-03 |
| CA1038378A (en) | 1978-09-12 |
| CH592620A5 (th) | 1977-10-31 |
| FR2192830A1 (th) | 1974-02-15 |
| FR2192830B1 (th) | 1977-07-01 |
| NL7310007A (th) | 1974-01-22 |
| AU474934B2 (en) | 1976-08-05 |
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