IL48544A - Tetrazolylalkyltriphenylphosphonium salt - Google Patents
Tetrazolylalkyltriphenylphosphonium saltInfo
- Publication number
- IL48544A IL48544A IL48544A IL4854472A IL48544A IL 48544 A IL48544 A IL 48544A IL 48544 A IL48544 A IL 48544A IL 4854472 A IL4854472 A IL 4854472A IL 48544 A IL48544 A IL 48544A
- Authority
- IL
- Israel
- Prior art keywords
- alpha
- double
- thp
- cis
- trans
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims abstract description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 5
- GJVUAUBGMGCLEB-UHFFFAOYSA-M triphenyl-[4-(2h-tetrazol-5-yl)butyl]phosphanium;bromide Chemical compound [Br-].N=1N=NNC=1CCCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GJVUAUBGMGCLEB-UHFFFAOYSA-M 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 150000003180 prostaglandins Chemical class 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 208000026817 47,XYY syndrome Diseases 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- -1 oct-1-yl Chemical class 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 230000002997 prostaglandinlike Effects 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- NIIFINHILCUHNF-UHFFFAOYSA-M 4-cyanobutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC#N)C1=CC=CC=C1 NIIFINHILCUHNF-UHFFFAOYSA-M 0.000 description 1
- NWWWGAKVHCSAEU-UHFFFAOYSA-N 5-bromopentanenitrile Chemical compound BrCCCCC#N NWWWGAKVHCSAEU-UHFFFAOYSA-N 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- 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
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Title compds. are of formula (I): where R = or ; A = alpha-OR3 where R3 = H or THP or B=H or A and B form a single bond; Y = a single or trans-double bond; X and Z = single or cis-double bonds, and if Z = cis-double Y is trans-double and X is cis-double; R' = H or l.alkyl, R2 = H or THP, and THP = tetrahydropyranyl. I have prostaglandin-like actions with prolonged activity. I are prepd. by reacting the novel reagent. II (prepd. from Ph3P(CH2)4CN with NaN3/NH4Cl/LiCl/DMF, followed by NaH), with 2- 5 alpha-hydroxy-3 alpha(OTHP)-2 beta-(3 alpha(OTHP)-trans-oct-1-ene 1-yl) cyclopent-1 alpha-yl aldehyde gamma-hemiacetal the oct-1-yl analogue, or the corresp. l.alkyl derivs. as required for I, and transforming the subsequent intermediate, by methods usual to prostaglandin chemistry.
[FR2283134A1]
Description
tetrazolylalkyltriphenylphosphonium salt PFIZER INC.
Cs 45344 P.C. (Ph) 5357 - Div. I This is a division of Israeli Patent Application No. 40183, filed August 22, 1972.
This invention relates to a novel intermediate useful in the preparation of compounds which can be converted into 2-descarboxy-2- [tetrazol-5-yl] prostaglandins .
The present invention comprises 4- (tetrazol-5-yl) -butyltriphenylphosphonium bromide, and a process for preparing a compound of the formula: characterized by reacting a compound of the formula: with sodium azide in the presence of ammonium chloride and lithium chloride in dimethylformamide .
An example of its use is as follows: As shown above, Hemiacetal II is caused to react with the novel reagent I to product III, the tetrazoyl analog of the bis-THP ether of PGF -.
An example for the preparation of the compound of this invention follows.
E X A M P L E A mixture of 5-bromovaleronitrile (16.2 g., 0.10 mole), triphenylphosphine (26.2 g., 0.10 mole) and toluene (100 ml.) was heated to reflux with stirring under nitrogen for 16 hours. The resulting thick white suspension was cooled to room temperature and filtered. The residue was washed with benzene and air dried to give 33.0 g. of a white crystalline solid, m.p. 230-232°, which was 4-cyanobutyltri-phenylphosphonium bromide.
Anal. |. Calc'd for C23H23BrNP: C, 65.10; H, 5.47; N, 3.30.
Found: C, 65.01; H, 5.40; N, 3.19.
A mixture of the phosphonium salt above (10.0 g., 23.5 mmoles) , ammonium chloride (1.60 g., 30.0 mmoles) , lithium chloride (0.032 g., 0.76 mmole) , sodium azide (1.91 g., 29.3 mmoles), and dimethylformamide (50 ml.) was heated to 127° (oil bath) under nitrogen with stirring for 18 hours.
The resulting suspension was cooled and filtered. The residue was washed with dimethylformamide and the combined filtrate and washings were concentrated (aspirator pressure, ca. 45°). The oily residue was crystallized from water at 0° and air dried to give a white crystalline solid (8.11 g.), m.p. 100-102°. The product was recrystallized from methanol-ether to give white prisms (7.18 g.), m.p. 197-206°. An analytical sample was prepared by recrystallization from 2-propanol to give a white crystalline powder, m.p. 212-213°, which was 4- (tetrazol-5-yl)butyltriphenylphosphonium bromide. Anal.
Calc'd for C23H24H4PBr: C, 59.10; H, 5.17; N, 11.99; P, 6.63; Br, 17.09.
Found: C, 59.35; H, 5.28; N, 12.31; P, 6.78; Br, 17.26.
Claims (2)
1. 4- (Tetrazol-5-yl) -butyltriphenylphosphonium bromide.
2. A process for preparing a compound of the formula: characterized by reacting a c Nund of the formula: with sodium azide in the presence of ammonium chloride and lithium chloride in dimethylformamide . For the/AppRcanb DR. RBtWoUytOHM AMD PA (
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17710271A | 1971-09-01 | 1971-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL48544A true IL48544A (en) | 1977-06-30 |
Family
ID=22647201
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40183A IL40183A (en) | 1971-09-01 | 1972-08-22 | Tetrazolyl derivatives of naturally occurring prostaglandins |
| IL48544A IL48544A (en) | 1971-09-01 | 1972-08-22 | Tetrazolylalkyltriphenylphosphonium salt |
| IL48544A IL48544A0 (en) | 1971-09-01 | 1975-11-26 | A tetrazolylalkyltriphenylphosphonium salt |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40183A IL40183A (en) | 1971-09-01 | 1972-08-22 | Tetrazolyl derivatives of naturally occurring prostaglandins |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL48544A IL48544A0 (en) | 1971-09-01 | 1975-11-26 | A tetrazolylalkyltriphenylphosphonium salt |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5724348B2 (en) |
| AR (4) | AR197304A1 (en) |
| AT (3) | AT327219B (en) |
| CA (1) | CA978939A (en) |
| DK (1) | DK144730C (en) |
| ES (3) | ES406250A1 (en) |
| FI (1) | FI55497C (en) |
| FR (3) | FR2283147A1 (en) |
| IL (3) | IL40183A (en) |
| PH (3) | PH10023A (en) |
| SE (4) | SE409032B (en) |
| ZA (1) | ZA725827B (en) |
-
1972
- 1972-08-22 IL IL40183A patent/IL40183A/en unknown
- 1972-08-22 IL IL48544A patent/IL48544A/en unknown
- 1972-08-24 ZA ZA725827A patent/ZA725827B/en unknown
- 1972-08-29 PH PH13850A patent/PH10023A/en unknown
- 1972-08-29 AT AT51974*7A patent/AT327219B/en not_active IP Right Cessation
- 1972-08-29 AT AT51974*A patent/ATA51974A/en not_active IP Right Cessation
- 1972-08-29 AT AT743472A patent/AT335079B/en not_active IP Right Cessation
- 1972-08-30 SE SE7211233A patent/SE409032B/en unknown
- 1972-08-30 FI FI2387/72A patent/FI55497C/en active
- 1972-08-31 ES ES406250A patent/ES406250A1/en not_active Expired
- 1972-08-31 CA CA150,669A patent/CA978939A/en not_active Expired
- 1972-08-31 DK DK430772A patent/DK144730C/en not_active IP Right Cessation
- 1972-08-31 AR AR243845A patent/AR197304A1/en active
- 1972-09-01 JP JP8784872A patent/JPS5724348B2/ja not_active Expired
-
1973
- 1973-06-22 AR AR248682A patent/AR199573A1/en active
- 1973-06-22 AR AR248681A patent/AR199784A1/en active
- 1973-06-22 AR AR248683A patent/AR199574A1/en active
- 1973-08-03 ES ES417558A patent/ES417558A1/en not_active Expired
- 1973-08-03 ES ES417557A patent/ES417557A1/en not_active Expired
-
1974
- 1974-06-03 PH PH15888A patent/PH10443A/en unknown
- 1974-06-03 PH PH15889A patent/PH10416A/en unknown
-
1975
- 1975-11-26 IL IL48544A patent/IL48544A0/en unknown
- 1975-11-26 FR FR7536205A patent/FR2283147A1/en active Granted
- 1975-11-26 FR FR7536203A patent/FR2283136A1/en active Granted
- 1975-11-26 FR FR7536204A patent/FR2283134A1/en active Granted
-
1976
- 1976-06-11 SE SE7606689A patent/SE421525B/en unknown
- 1976-06-11 SE SE7606690A patent/SE421526B/en unknown
- 1976-06-11 SE SE7606691A patent/SE424185B/en unknown
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