IL27271A - Isoprenoid compounds and process for the manufacture thereof - Google Patents
Isoprenoid compounds and process for the manufacture thereofInfo
- Publication number
- IL27271A IL27271A IL27271A IL2727167A IL27271A IL 27271 A IL27271 A IL 27271A IL 27271 A IL27271 A IL 27271A IL 2727167 A IL2727167 A IL 2727167A IL 27271 A IL27271 A IL 27271A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- lower alkyl
- compound
- represents lower
- aldehyde
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- -1 Isoprenoid compounds Chemical class 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- BWKDLDWUVLGWFC-UHFFFAOYSA-N calcium;azanide Chemical compound [NH2-].[NH2-].[Ca+2] BWKDLDWUVLGWFC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- KDOAHVPFGIYCEU-UHFFFAOYSA-N 3-ethoxy-2-methylprop-2-enal Chemical compound CCOC=C(C)C=O KDOAHVPFGIYCEU-UHFFFAOYSA-N 0.000 claims 1
- RXVCZRFZUPUIQQ-UHFFFAOYSA-N 5-(2-methoxypropan-2-yloxy)-3-methylpent-3-en-1-yne Chemical compound COC(C)(C)OCC=C(C)C#C RXVCZRFZUPUIQQ-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 238000006359 acetalization reaction Methods 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000004291 polyenes Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YKLWPGCWVBBCTO-UHFFFAOYSA-N 1-ethenoxyprop-1-ene Chemical compound CC=COC=C YKLWPGCWVBBCTO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/283—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH123266A CH468330A (de) | 1966-01-28 | 1966-01-28 | Verfahren zur Herstellung von isoprenoiden Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27271A true IL27271A (en) | 1971-04-28 |
Family
ID=4205567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL27271A IL27271A (en) | 1966-01-28 | 1967-01-18 | Isoprenoid compounds and process for the manufacture thereof |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3687990A (en0) |
| JP (1) | JPS5019530B1 (en0) |
| BE (1) | BE693072A (en0) |
| CH (1) | CH468330A (en0) |
| DE (1) | DE1568805A1 (en0) |
| ES (1) | ES336151A1 (en0) |
| FR (1) | FR1506896A (en0) |
| GB (2) | GB1153923A (en0) |
| IL (1) | IL27271A (en0) |
| NL (1) | NL6700714A (en0) |
| SE (1) | SE354465B (en0) |
| YU (1) | YU31653B (en0) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3919329A (en) * | 1974-04-25 | 1975-11-11 | Zoecon Corp | Synthesis of the pink bollworm sex pheromone |
| JPS5770892U (en0) * | 1980-10-16 | 1982-04-28 | ||
| JPS5943190U (ja) * | 1982-09-17 | 1984-03-21 | 株式会社大平 | ノツク式ペンシルのノツク冠 |
| PL373780A1 (en) * | 2002-02-25 | 2005-09-19 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| US7759506B2 (en) * | 2002-02-25 | 2010-07-20 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| CN101180257A (zh) | 2005-02-24 | 2008-05-14 | 扩散药品有限公司 | 反式类胡萝卜素、其合成、制剂和用途 |
| WO2008136900A1 (en) * | 2007-04-13 | 2008-11-13 | Diffusion Pharmaceuticals Llc | Use of bipolar trans carotenoids as a pretreatment and in the treatment of peripheral vascular disease |
| BRPI0818119A2 (pt) * | 2007-10-31 | 2015-08-04 | Diffusion Pharmaceuticals Llc | Uma nova classe de produtos terapêuticos que melhoram difusão de molécula pequena |
| CN102458110A (zh) | 2009-06-22 | 2012-05-16 | 扩散药品有限公司 | 扩散促进化合物及其单独或与溶栓药一起的应用 |
| ES2654945T3 (es) | 2010-06-02 | 2018-02-15 | Diffusion Pharmaceuticals Llc | Formulaciones orales de carotenoides trans bipolares |
| CA3018550A1 (en) | 2016-03-24 | 2017-09-28 | Diffusion Pharmaceuticals Llc | Use of bipolar trans carotenoids with chemotherapy and radiotherapy for treatment of cancer |
| CN116854571A (zh) * | 2023-06-28 | 2023-10-10 | 万华化学集团股份有限公司 | 一种阿朴酯中间体的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3489806A (en) * | 1967-01-19 | 1970-01-13 | Hoffmann La Roche | Isoprenoid compounds and a process for producing the same |
-
1966
- 1966-01-28 CH CH123266A patent/CH468330A/de unknown
- 1966-12-13 DE DE19661568805 patent/DE1568805A1/de active Pending
- 1966-12-29 FR FR89266A patent/FR1506896A/fr not_active Expired
-
1967
- 1967-01-11 YU YU0041/67A patent/YU31653B/xx unknown
- 1967-01-17 NL NL6700714A patent/NL6700714A/xx unknown
- 1967-01-18 IL IL27271A patent/IL27271A/en unknown
- 1967-01-24 BE BE693072D patent/BE693072A/xx unknown
- 1967-01-26 JP JP674835A patent/JPS5019530B1/ja active Pending
- 1967-01-27 ES ES336151A patent/ES336151A1/es not_active Expired
- 1967-01-27 GB GB4190/67A patent/GB1153923A/en not_active Expired
- 1967-01-27 GB GB60559/68A patent/GB1153924A/en not_active Expired
- 1967-01-27 SE SE01235/67A patent/SE354465B/xx unknown
-
1969
- 1969-07-01 US US838305A patent/US3687990A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3687990A (en) | 1972-08-29 |
| BE693072A (en0) | 1967-07-24 |
| GB1153923A (en) | 1969-06-04 |
| FR1506896A (fr) | 1967-12-22 |
| JPS5019530B1 (en0) | 1975-07-08 |
| SE354465B (en0) | 1973-03-12 |
| CH468330A (de) | 1969-02-15 |
| GB1153924A (en) | 1969-06-04 |
| ES336151A1 (es) | 1968-04-01 |
| DE1568805A1 (de) | 1970-04-02 |
| YU4167A (en) | 1973-04-30 |
| NL6700714A (en0) | 1967-07-31 |
| YU31653B (en) | 1973-10-31 |
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