CH621773A5 - Process for the preparation of novel 9-oxo-15zeta-hydroxy-20-alkylideneprost-13(trans)enoic acid derivatives - Google Patents
Process for the preparation of novel 9-oxo-15zeta-hydroxy-20-alkylideneprost-13(trans)enoic acid derivatives Download PDFInfo
- Publication number
- CH621773A5 CH621773A5 CH1217075A CH1217075A CH621773A5 CH 621773 A5 CH621773 A5 CH 621773A5 CH 1217075 A CH1217075 A CH 1217075A CH 1217075 A CH1217075 A CH 1217075A CH 621773 A5 CH621773 A5 CH 621773A5
- Authority
- CH
- Switzerland
- Prior art keywords
- trans
- oxo
- methyl
- acid
- hydroxy
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 170
- 238000002360 preparation method Methods 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 18
- -1 alkyl radicals Chemical class 0.000 claims description 215
- 150000001875 compounds Chemical class 0.000 claims description 199
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 96
- 125000006239 protecting group Chemical group 0.000 claims description 91
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 13
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
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- 230000032050 esterification Effects 0.000 claims description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000126 substance Substances 0.000 claims description 2
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- 238000006243 chemical reaction Methods 0.000 description 128
- 239000000243 solution Substances 0.000 description 100
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- 238000002329 infrared spectrum Methods 0.000 description 90
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 82
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 63
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- 101150041968 CDC13 gene Proteins 0.000 description 43
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- 239000000284 extract Substances 0.000 description 38
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
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- 230000002829 reductive effect Effects 0.000 description 17
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 15
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 14
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- 229910002027 silica gel Inorganic materials 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
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- 125000000217 alkyl group Chemical group 0.000 description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
- 239000003638 chemical reducing agent Substances 0.000 description 11
- 150000003180 prostaglandins Chemical class 0.000 description 11
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- 229960003975 potassium Drugs 0.000 description 10
- 239000011591 potassium Substances 0.000 description 10
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- 239000012300 argon atmosphere Substances 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- QHINYJQPBCMLCJ-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan Chemical compound C1COC2CCCC21 QHINYJQPBCMLCJ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 230000002496 gastric effect Effects 0.000 description 7
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 230000028327 secretion Effects 0.000 description 7
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- 229910000104 sodium hydride Inorganic materials 0.000 description 7
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 6
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
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- 125000003118 aryl group Chemical group 0.000 description 4
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- 125000004122 cyclic group Chemical group 0.000 description 3
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- 238000010253 intravenous injection Methods 0.000 description 3
- HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 3
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- 210000002784 stomach Anatomy 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- RGYLYUZOGHTBRF-BIHRQFPBSA-N tetragastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C2=CC=CC=C2NC=1)CCSC)C(N)=O)C1=CC=CC=C1 RGYLYUZOGHTBRF-BIHRQFPBSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- JJPVWQWOOQYHCB-UHFFFAOYSA-N triethyl(phenyl)azanium Chemical compound CC[N+](CC)(CC)C1=CC=CC=C1 JJPVWQWOOQYHCB-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000008096 xylene 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
- 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
- C07F9/4015—Esters of acyclic unsaturated acids
-
- 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)
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10814374A JPS5434724B2 (da) | 1974-09-19 | 1974-09-19 | |
| JP6052075A JPS5835184B2 (ja) | 1975-05-21 | 1975-05-21 | プロスタグランジンユウドウタイノセイホウ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621773A5 true CH621773A5 (en) | 1981-02-27 |
Family
ID=26401594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1217075A CH621773A5 (en) | 1974-09-19 | 1975-09-19 | Process for the preparation of novel 9-oxo-15zeta-hydroxy-20-alkylideneprost-13(trans)enoic acid derivatives |
Country Status (9)
| Country | Link |
|---|---|
| CA (1) | CA1072956A (da) |
| CH (1) | CH621773A5 (da) |
| DE (1) | DE2541883C2 (da) |
| DK (1) | DK418675A (da) |
| ES (1) | ES441126A1 (da) |
| FR (1) | FR2285124A1 (da) |
| GB (1) | GB1499018A (da) |
| NL (1) | NL170413C (da) |
| SE (1) | SE413023B (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2635985A1 (de) * | 1976-08-06 | 1978-02-09 | Schering Ag | Prostansaeurederivat und verfahren zu ihrer herstellung |
| IT1078774B (it) * | 1976-09-07 | 1985-05-08 | Lpb Ist Farm | Derivato dell acido 19 metil 9 cheto 15 idrossi prost 18 enoico |
| GB2048254B (en) * | 1979-04-02 | 1983-05-25 | Upjohn Co | 19,20 -didehydro-19-hydroxy and 19-oxo-prostaglandin derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA711840B (en) * | 1970-04-20 | 1972-01-26 | Upjohn Co | Pge3-type compounds |
-
1975
- 1975-09-12 GB GB37626/75A patent/GB1499018A/en not_active Expired
- 1975-09-18 SE SE7510466A patent/SE413023B/xx not_active IP Right Cessation
- 1975-09-18 DK DK418675A patent/DK418675A/da not_active Application Discontinuation
- 1975-09-18 FR FR7528588A patent/FR2285124A1/fr active Granted
- 1975-09-18 CA CA235,783A patent/CA1072956A/en not_active Expired
- 1975-09-19 DE DE2541883A patent/DE2541883C2/de not_active Expired
- 1975-09-19 NL NLAANVRAGE7511127,A patent/NL170413C/xx not_active IP Right Cessation
- 1975-09-19 ES ES441126A patent/ES441126A1/es not_active Expired
- 1975-09-19 CH CH1217075A patent/CH621773A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1072956A (en) | 1980-03-04 |
| FR2285124A1 (fr) | 1976-04-16 |
| NL7511127A (nl) | 1976-03-23 |
| SE413023B (sv) | 1980-03-31 |
| FR2285124B1 (da) | 1979-09-14 |
| NL170413B (nl) | 1982-06-01 |
| NL170413C (nl) | 1982-11-01 |
| DK418675A (da) | 1976-03-20 |
| GB1499018A (en) | 1978-01-25 |
| SE7510466L (sv) | 1976-03-22 |
| DE2541883A1 (de) | 1976-04-01 |
| DE2541883C2 (de) | 1984-03-29 |
| ES441126A1 (es) | 1977-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |