IL99378A - Synthesis of monoalkanoyl prodrugs - Google Patents

Synthesis of monoalkanoyl prodrugs

Info

Publication number: IL99378A
Authority: IL; Israel
Prior art keywords: process according; ferrocene; ferrocene derivative; anhydride; acid
Prior art date: 1990-10-03

Application number

IL9937891A

Other languages

English (en)

Hebrew (he)

Other versions

IL99378A0 (en

Original Assignee

Poudres & Explosifs Ste Nale

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-10-03

Filing date

1991-09-03

Publication date

1995-12-31

1991-09-03 Application filed by Poudres & Explosifs Ste Nale filed Critical Poudres & Explosifs Ste Nale

1992-08-18 Publication of IL99378A0 publication Critical patent/IL99378A0/xx

1995-12-31 Publication of IL99378A publication Critical patent/IL99378A/en

Links

230000015572 biosynthetic process Effects 0.000 title claims description 13
238000003786 synthesis reaction Methods 0.000 title claims description 13
KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical class [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
238000000034 method Methods 0.000 claims description 20
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 16
150000008064 anhydrides Chemical class 0.000 claims description 11
150000004820 halides Chemical class 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000012074 organic phase Substances 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
238000001704 evaporation Methods 0.000 claims description 3
238000001914 filtration Methods 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
229910004664 Cerium(III) chloride Inorganic materials 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 1
239000000243 solution Substances 0.000 description 16
YYCOVCKXTXEBNV-UHFFFAOYSA-N ClCCCC(=O)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] Chemical compound ClCCCC(=O)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] YYCOVCKXTXEBNV-UHFFFAOYSA-N 0.000 description 10
-1 carboxylic acid halide Chemical class 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 5
230000000052 comparative effect Effects 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
FCBQZFWYMGKDNR-UHFFFAOYSA-N [Fe++].c1cc[cH-]c1.[SiH3][c-]1cccc1 Chemical class [Fe++].c1cc[cH-]c1.[SiH3][c-]1cccc1 FCBQZFWYMGKDNR-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000012043 crude product Substances 0.000 description 2
FCNXGBYXGSKCDG-UHFFFAOYSA-N ethylferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.CC[C-]1C=CC=C1 FCNXGBYXGSKCDG-UHFFFAOYSA-N 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000011084 recovery Methods 0.000 description 2
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
FRPBWRRYBHCJCW-UHFFFAOYSA-N 2-chloro-1-cyclopenta-2,4-dien-1-ylethanone cyclopenta-1,3-diene iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.ClCC(=O)[c-]1cccc1 FRPBWRRYBHCJCW-UHFFFAOYSA-N 0.000 description 1
CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 1
KOORPTPWUZWGBJ-UHFFFAOYSA-N BrCCCCC(=O)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] Chemical compound BrCCCCC(=O)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] KOORPTPWUZWGBJ-UHFFFAOYSA-N 0.000 description 1
ICLYFLWKHQGPBM-UHFFFAOYSA-N ClCCC(=O)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] Chemical compound ClCCC(=O)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] ICLYFLWKHQGPBM-UHFFFAOYSA-N 0.000 description 1
MPRAJAJNLRLDDL-UHFFFAOYSA-N [C-]1(C=CC=C1)C(=O)CCCCCBr.[CH-]1C=CC=C1.[Fe+2] Chemical compound [C-]1(C=CC=C1)C(=O)CCCCCBr.[CH-]1C=CC=C1.[Fe+2] MPRAJAJNLRLDDL-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
ACNAXEZQQXXWAE-UHFFFAOYSA-M cyclopenta-1,3-diene;1-cyclopenta-2,4-dien-1-ylidene-3,5,5-trimethylhexan-1-olate;iron(2+) Chemical compound [Fe+2].C=1C=C[CH-]C=1.CC(C)(C)CC(C)CC([O-])=C1C=CC=C1 ACNAXEZQQXXWAE-UHFFFAOYSA-M 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002483 medication Methods 0.000 description 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 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL9937891A 1990-10-03 1991-09-03 Synthesis of monoalkanoyl prodrugs IL99378A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9012157A FR2667600B1 (fr)	1990-10-03	1990-10-03	Procede de synthese de monohalogenoalcanoylferrocenes.

Publications (2)

Publication Number	Publication Date
IL99378A0 IL99378A0 (en)	1992-08-18
IL99378A true IL99378A (en)	1995-12-31

Family

ID=9400879

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9937891A IL99378A (en)	1990-10-03	1991-09-03	Synthesis of monoalkanoyl prodrugs

Country Status (6)

Country	Link
US (1)	US5190671A (de)
EP (1)	EP0479664B1 (de)
JP (1)	JPH04273887A (de)
DE (1)	DE69109791T2 (de)
FR (1)	FR2667600B1 (de)
IL (1)	IL99378A (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2721028B1 (fr) *	1994-06-14	1996-07-12	Poudres & Explosifs Ste Nale	Procédé de synthèse d'halogénoalkylferrocènes.
DE19516517C1 (de) *	1995-05-05	1997-02-06	Pluto Chem Betriebe	Ferrocenverbindungen, Verfahren zu deren Herstellung sowie der Zwischenprodukte
DE60012372T2 (de) *	2000-03-31	2005-07-28	Council Of Scientific And Industrial Research	Verbesserte herstellungsmethode für acylferrocene
WO2011048615A1 (en)	2009-10-19	2011-04-28	Cbz Chemicals Limited	Process for the synthesis of silylferrocene compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE587379A (de) *	1959-02-09
DE2623487A1 (de) *	1976-05-26	1977-12-15	Hoechst Ag	Ferrocenderivate und verfahren zu ihrer herstellung
DE2623486C2 (de) *	1976-05-26	1982-12-30	Hoechst Ag, 6000 Frankfurt	3.5.5-Trimethylhexanoyl-ferrocen, Verfahren zu seiner Herstellung und pharmazeutische Präparate

1990
- 1990-10-03 FR FR9012157A patent/FR2667600B1/fr not_active Expired - Fee Related
1991
- 1991-09-03 IL IL9937891A patent/IL99378A/en not_active IP Right Cessation
- 1991-09-24 JP JP3242944A patent/JPH04273887A/ja active Pending
- 1991-10-01 EP EP91402611A patent/EP0479664B1/de not_active Expired - Lifetime
- 1991-10-01 DE DE69109791T patent/DE69109791T2/de not_active Expired - Fee Related
- 1991-10-02 US US07/769,776 patent/US5190671A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US5190671A (en)	1993-03-02
IL99378A0 (en)	1992-08-18
DE69109791D1 (de)	1995-06-22
EP0479664B1 (de)	1995-05-17
JPH04273887A (ja)	1992-09-30
FR2667600A1 (fr)	1992-04-10
DE69109791T2 (de)	1995-09-14
FR2667600B1 (fr)	1993-07-23
EP0479664A1 (de)	1992-04-08

Legal Events

Date	Code	Title
1996-06-18	FF	Patent granted
1998-02-08	KB	Patent renewed
2002-05-23	MM9K	Patent not in force due to non-payment of renewal fees

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