DK142143B - Analogifremgangsmåde til fremstilling af 2,3-methylenprostaglandin F2alfa- eller E2-derivater. - Google Patents
Analogifremgangsmåde til fremstilling af 2,3-methylenprostaglandin F2alfa- eller E2-derivater. Download PDFInfo
- Publication number
- DK142143B DK142143B DK352974AA DK352974A DK142143B DK 142143 B DK142143 B DK 142143B DK 352974A A DK352974A A DK 352974AA DK 352974 A DK352974 A DK 352974A DK 142143 B DK142143 B DK 142143B
- Authority
- DK
- Denmark
- Prior art keywords
- ppm
- trans
- methylene
- spectrum
- methylene chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 6
- -1 2,3-Methylene Prostaglandin Chemical class 0.000 title description 47
- 238000002329 infrared spectrum Methods 0.000 claims description 45
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 45
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 177
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 72
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- 239000000243 solution Substances 0.000 description 52
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- 239000000203 mixture Substances 0.000 description 29
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- WGCXTGBZBFBQPP-UHFFFAOYSA-N prostaglandin E2 methyl ester Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(=O)OC WGCXTGBZBFBQPP-UHFFFAOYSA-N 0.000 description 5
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- 239000013078 crystal Substances 0.000 description 4
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- 230000002496 gastric effect Effects 0.000 description 4
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- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 150000003180 prostaglandins Chemical class 0.000 description 4
- 230000028327 secretion Effects 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- ZTUZIGMVTFAJGH-AQHBPOCSSA-N 2-[(1S,2R)-2-carboxycyclopropyl]ethyl-triphenylphosphanium bromide Chemical compound [Br-].C(=O)(O)[C@H]1[C@@H](C1)CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 ZTUZIGMVTFAJGH-AQHBPOCSSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 210000004291 uterus Anatomy 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
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- 239000001632 sodium acetate Substances 0.000 description 2
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 description 1
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- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003165 prostaglandin E1 derivatives Chemical class 0.000 description 1
- PJDMFGSFLLCCAO-UHFFFAOYSA-N prostaglandin-F2alpha methyl ester Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CC=CCCCC(=O)OC PJDMFGSFLLCCAO-UHFFFAOYSA-N 0.000 description 1
- 230000002997 prostaglandinlike Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NKAAEMMYHLFEFN-ZVGUSBNCSA-M sodium;(2r,3r)-2,3,4-trihydroxy-4-oxobutanoate Chemical compound [Na+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O NKAAEMMYHLFEFN-ZVGUSBNCSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK438575A DK438575A (da) | 1973-07-09 | 1975-09-29 | Carbocycliske forbindelser |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH995973 | 1973-07-09 | ||
| CH995973A CH599147A5 (en) | 1973-07-09 | 1973-07-09 | Long-acting synthetic prostaglandins |
| CH604974 | 1974-05-04 | ||
| CH604974 | 1974-05-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK352974A DK352974A (enrdf_load_stackoverflow) | 1975-03-03 |
| DK142143B true DK142143B (da) | 1980-09-08 |
| DK142143C DK142143C (enrdf_load_stackoverflow) | 1981-02-09 |
Family
ID=25698889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK352974AA DK142143B (da) | 1973-07-09 | 1974-07-01 | Analogifremgangsmåde til fremstilling af 2,3-methylenprostaglandin F2alfa- eller E2-derivater. |
Country Status (15)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2638401A1 (de) * | 1975-09-05 | 1977-03-17 | Sandoz Ag | Neue prostaglandine, ihre verwendung und herstellung |
| JPS52116930U (enrdf_load_stackoverflow) * | 1976-03-03 | 1977-09-05 | ||
| JPS55147056U (enrdf_load_stackoverflow) * | 1979-04-06 | 1980-10-22 | ||
| US4431669A (en) * | 1982-12-17 | 1984-02-14 | Schering Corporation | Cyclopropyl substituted polyenes |
| JPH04204679A (ja) * | 1990-11-30 | 1992-07-27 | Fuji Photo Film Co Ltd | 電子写真式画像記録装置 |
-
1974
- 1974-07-01 NO NO742378A patent/NO742378L/no unknown
- 1974-07-01 FI FI2011/74A patent/FI58117C/fi active
- 1974-07-01 SE SE7408689A patent/SE7408689L/xx unknown
- 1974-07-01 DK DK352974AA patent/DK142143B/da unknown
- 1974-07-03 DE DE2431930A patent/DE2431930A1/de not_active Withdrawn
- 1974-07-05 FR FR7423427A patent/FR2236490B1/fr not_active Expired
- 1974-07-05 NL NL7409119A patent/NL7409119A/xx not_active Application Discontinuation
- 1974-07-05 DD DD179745A patent/DD113348A5/xx unknown
- 1974-07-08 GB GB30268/74A patent/GB1479964A/en not_active Expired
- 1974-07-08 AT AT559874A patent/AT355233B/de not_active IP Right Cessation
- 1974-07-08 IL IL45215A patent/IL45215A/en unknown
- 1974-07-08 GB GB1901/77A patent/GB1479965A/en not_active Expired
- 1974-07-08 JP JP49077462A patent/JPS5040549A/ja active Pending
- 1974-07-08 ES ES74428063A patent/ES428063A1/es not_active Expired
- 1974-07-08 IE IE1443/74A patent/IE41342B1/xx unknown
- 1974-07-08 CA CA204,340A patent/CA1050976A/en not_active Expired
-
1975
- 1975-10-30 SE SE7512194A patent/SE7512194L/xx unknown
-
1976
- 1976-05-17 ES ES448000A patent/ES448000A1/es not_active Expired
- 1976-10-01 FR FR7629555A patent/FR2318169A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2318169A1 (fr) | 1977-02-11 |
| CA1050976A (en) | 1979-03-20 |
| SE7512194L (sv) | 1975-10-30 |
| ATA559874A (de) | 1979-07-15 |
| IL45215A0 (en) | 1975-02-10 |
| JPS5040549A (enrdf_load_stackoverflow) | 1975-04-14 |
| FI58117B (fi) | 1980-08-29 |
| SE7408689L (enrdf_load_stackoverflow) | 1975-01-10 |
| NO742378L (enrdf_load_stackoverflow) | 1975-02-03 |
| DK352974A (enrdf_load_stackoverflow) | 1975-03-03 |
| NL7409119A (nl) | 1975-01-13 |
| FR2236490B1 (enrdf_load_stackoverflow) | 1978-07-21 |
| DK142143C (enrdf_load_stackoverflow) | 1981-02-09 |
| ES448000A1 (es) | 1977-11-01 |
| GB1479964A (en) | 1977-07-13 |
| DE2431930A1 (de) | 1975-01-30 |
| FR2236490A1 (enrdf_load_stackoverflow) | 1975-02-07 |
| IE41342B1 (en) | 1979-12-05 |
| IL45215A (en) | 1977-07-31 |
| FI58117C (fi) | 1980-12-10 |
| DD113348A5 (enrdf_load_stackoverflow) | 1975-06-05 |
| GB1479965A (en) | 1977-07-13 |
| ES428063A1 (es) | 1977-02-01 |
| FR2318169B1 (enrdf_load_stackoverflow) | 1978-11-03 |
| IE41342L (en) | 1975-01-09 |
| FI201174A7 (enrdf_load_stackoverflow) | 1975-01-10 |
| AT355233B (de) | 1980-02-25 |
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