YU46781B - Postupak za dobijanje tetrazolovih intermedijera - Google Patents
Postupak za dobijanje tetrazolovih intermedijeraInfo
- Publication number
- YU46781B YU46781B YU36488A YU36488A YU46781B YU 46781 B YU46781 B YU 46781B YU 36488 A YU36488 A YU 36488A YU 36488 A YU36488 A YU 36488A YU 46781 B YU46781 B YU 46781B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- formula
- compound
- methyl
- hydrogen
- solvent
- Prior art date
Links
- 150000003536 tetrazoles Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 abstract 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
POSTUPAK ZA DOBIJANJE TETRAZOLOVIH INTERMEDIJERA formula: u kojoj R1, R2, R3, R4, R5 i R6 svaki nezavisno predstavljaju vodonik, metil, metoksi ili fluoro i B je vodonik, metil, CH2X ili CHO, gde je X hloro, bromo ili jodo, naznacen time, sto benzofenon formule: u kojoj su R1, R2, R3, R4, R5 i R6 kao sto je definisano gore, u intertnom organskom rastvaracu kao sto je tetrahidrofuran, dietil etar ili 1,2-dimetoksietan, u prisustvu jake baze kao sto je n-butil-litijum i na temperaturi od -20 do -78°C, reaguje sa tetrazolom formule: u kojoj R8 predstavlja vodonik ili metil, da bi se dobilo jedinjenje formule: u kojoj su R1, R2, R3, R4, R5, R6 i R8 kao sto je definisano gore; sto se jedinjenje formule (VII) podvrgava dehidrataciji zagrevanjem u pogodnom rastvaracu, kao sto je toluol, benzol ili ksilol, sa organskom ili mineralnom kiselinom kao sto je p-toluolsulfonska ili sumporna kiselina i uz uklanjanje vode sredstvom za susenje ili na azeotropni nacin, da bi se dobilo jedinjenje formule (I) u kojoj je B vodonik (formula Ic) ili metil (formula Id); sto se zatim, po potrebi, jedinjenje formule (Ic) prevodi u jedinjenje formule (I) u kojoj B predstavlja CHO (formula III) reakcijom sa etil formijatom u inertnom organskom rastvaracu kao sto je tetrahidrofuran ili 1,2-dimetoksietan, na temperaturi od -20 do -78°C i u prisustvu jake baze kao sto je n-butilltijum; ili se jedinjenje formule (Id), po potrebi, prevodi u jedinjenje formule (I) u kojoj B predstavlja grupu CH2X (formula Ie), gde je X kao sto je definisano gore, halogenovanjem sa N-halosukcinimidom kao sto je N-bromosukcinimid, u rastvaracu kao sto je ugljen tetrahlorid i u prisustvu katalizatora kao sto je azobis-izobutironitril ili benzoil peroksid nakon cega se, po potrebi, jedinjenje formule (Ie) prevodi u jedinjenje formule (III) reakcijom sa 2-nitropropanom, u rastvaracu kao sto je etanol i u prisustvu baze, kao sto je natrijum etoksid.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU145189A YU46635B (sh) | 1987-02-25 | 1989-07-19 | Postupak za dobijanje tetrazolovih intermedijera |
| YU145289A YU46636B (sh) | 1987-02-25 | 1989-07-19 | Postupak za dobijanje antihiper-holesterolskih derivata tetrazola |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1855887A | 1987-02-25 | 1987-02-25 | |
| US07/151,512 US4898949A (en) | 1987-02-25 | 1988-02-18 | Intermediates for the preparation of antihypercholesterolemic tetrazole compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU36488A YU36488A (en) | 1990-02-28 |
| YU46781B true YU46781B (sh) | 1994-05-10 |
Family
ID=26691250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU36488A YU46781B (sh) | 1987-02-25 | 1988-02-25 | Postupak za dobijanje tetrazolovih intermedijera |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4898949A (sh) |
| JP (1) | JP2603284B2 (sh) |
| KR (1) | KR960007167B1 (sh) |
| CN (1) | CN1030077C (sh) |
| AT (1) | AT395588B (sh) |
| AU (1) | AU610562B2 (sh) |
| BE (1) | BE1002115A3 (sh) |
| CA (1) | CA1328269C (sh) |
| CH (1) | CH678182A5 (sh) |
| DE (1) | DE3805789C2 (sh) |
| DK (2) | DK97388A (sh) |
| ES (1) | ES2009547A6 (sh) |
| FI (1) | FI96600C (sh) |
| FR (1) | FR2611201B1 (sh) |
| GB (1) | GB2202845B (sh) |
| GR (1) | GR1000473B (sh) |
| HU (3) | HU201534B (sh) |
| IE (1) | IE61608B1 (sh) |
| IT (1) | IT1216752B (sh) |
| LU (1) | LU87143A1 (sh) |
| MY (1) | MY102290A (sh) |
| NL (1) | NL8800468A (sh) |
| NO (1) | NO178432C (sh) |
| NZ (1) | NZ223621A (sh) |
| PT (1) | PT86821B (sh) |
| SE (3) | SE504553C2 (sh) |
| YU (1) | YU46781B (sh) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4870187A (en) * | 1988-08-23 | 1989-09-26 | Bristol-Myers Company | Antihypercholesterolemic tetrazol-1-yl compounds |
| FI94339C (fi) | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| US5260325A (en) * | 1991-08-19 | 1993-11-09 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking tertiary amides |
| CA2137049A1 (en) * | 1993-12-15 | 1995-06-16 | John K. Thottathil | Amino acid salts of and methods for preparing antihypercholesterolemic tetrazole compounds |
| KR100681366B1 (ko) * | 1997-12-19 | 2007-02-12 | 워너-램버트 익스포트 리미티드 | 1,3-디올의 합성방법 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160100A (en) * | 1973-03-23 | 1979-07-03 | American Home Products Corporation | Oxamic acid derivatives |
| US4013647A (en) * | 1976-03-23 | 1977-03-22 | American Home Products Corporation | Morpholine containing tetrazole-5-carboxamide derivatives |
| JPS53147073A (en) * | 1977-05-24 | 1978-12-21 | Sankyo Co Ltd | Mevalonolactone derivatives |
| NZ194557A (en) * | 1979-08-17 | 1984-09-28 | Merck & Co Inc | Substituted pyranone derivatives;dihydroxy acids therefrom;pharmaceutical compositions |
| US4567289A (en) * | 1979-08-17 | 1986-01-28 | Merck & Co., Inc. | Substituted pyranone inhibitors of cholesterol synthesis |
| US4375475A (en) * | 1979-08-17 | 1983-03-01 | Merck & Co., Inc. | Substituted pyranone inhibitors of cholesterol synthesis |
| EP0068038B1 (en) * | 1981-06-29 | 1985-09-25 | Merck & Co. Inc. | (+)-(4r,6s)-(e)-6-(2-(4'-fluoro-3,3',5-trimethyl-(1,1'-biphenyl)-2-yl)ethenyl)-3,4,5,6-tetrahydro-4-hydroxy-2h-pyran-2-one, a process for preparing and a pharmaceutical composition containing the same |
| AU570021B2 (en) * | 1982-11-22 | 1988-03-03 | Novartis Ag | Analogs of mevalolactone |
| US4739073A (en) * | 1983-11-04 | 1988-04-19 | Sandoz Pharmaceuticals Corp. | Intermediates in the synthesis of indole analogs of mevalonolactone and derivatives thereof |
| PT77996B (en) * | 1983-01-24 | 1986-05-30 | Sandoz Sa | Process of the preparations of mevalonelactone analogs and derivatives thereof and of pharmaceutical compositions containing them |
| US5105017A (en) * | 1983-07-18 | 1992-04-14 | Eli Lilly And Company | Leukotriene antagonist intermediates |
| CA1327360C (en) * | 1983-11-14 | 1994-03-01 | William F. Hoffman | Oxo-analogs of mevinolin-like antihypercholesterolemic agents |
| US4613610A (en) * | 1984-06-22 | 1986-09-23 | Sandoz Pharmaceuticals Corp. | Cholesterol biosynthesis inhibiting pyrazole analogs of mevalonolactone and its derivatives |
| JPS61502467A (ja) * | 1984-06-22 | 1986-10-30 | サンド・アクチエンゲゼルシヤフト | メバロノラクトンのピラゾ−ル同族体およびその誘導体、それらの製造方法ならびに用途 |
| US4668794A (en) * | 1985-05-22 | 1987-05-26 | Sandoz Pharm. Corp. | Intermediate imidazole acrolein analogs |
| US4621099A (en) * | 1985-09-23 | 1986-11-04 | Usv Pharmaceutical Corporation | Polyene compounds useful in the treatment of allergic responses |
| US4681893A (en) * | 1986-05-30 | 1987-07-21 | Warner-Lambert Company | Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthesis |
| US4678806A (en) * | 1986-09-02 | 1987-07-07 | Merck & Co., Inc. | Prodrugs of antihypercholesterolemic compounds |
| AU601264B2 (en) * | 1987-02-25 | 1990-09-06 | Bristol-Myers Squibb Company | Antihypercholesterolemic tetrazole compounds |
-
1988
- 1988-02-18 US US07/151,512 patent/US4898949A/en not_active Expired - Lifetime
- 1988-02-24 AT AT0046088A patent/AT395588B/de not_active IP Right Cessation
- 1988-02-24 JP JP63041828A patent/JP2603284B2/ja not_active Expired - Fee Related
- 1988-02-24 ES ES8800533A patent/ES2009547A6/es not_active Expired
- 1988-02-24 FR FR888802212A patent/FR2611201B1/fr not_active Expired - Fee Related
- 1988-02-24 AU AU12132/88A patent/AU610562B2/en not_active Ceased
- 1988-02-24 IE IE50288A patent/IE61608B1/en not_active IP Right Cessation
- 1988-02-24 IT IT8819526A patent/IT1216752B/it active
- 1988-02-24 CH CH691/88A patent/CH678182A5/de not_active IP Right Cessation
- 1988-02-24 GR GR880100100A patent/GR1000473B/el not_active IP Right Cessation
- 1988-02-24 KR KR1019880001915A patent/KR960007167B1/ko not_active IP Right Cessation
- 1988-02-24 NL NL8800468A patent/NL8800468A/nl not_active Application Discontinuation
- 1988-02-24 HU HU895133A patent/HU201534B/hu not_active IP Right Cessation
- 1988-02-24 CA CA000559671A patent/CA1328269C/en not_active Expired - Fee Related
- 1988-02-24 GB GB8804281A patent/GB2202845B/en not_active Expired - Fee Related
- 1988-02-24 DE DE3805789A patent/DE3805789C2/de not_active Expired - Fee Related
- 1988-02-24 MY MYPI88000180A patent/MY102290A/en unknown
- 1988-02-24 FI FI880868A patent/FI96600C/fi not_active IP Right Cessation
- 1988-02-24 HU HU895124A patent/HU201533B/hu not_active IP Right Cessation
- 1988-02-24 NO NO880802A patent/NO178432C/no not_active IP Right Cessation
- 1988-02-24 HU HU88885A patent/HU201532B/hu not_active IP Right Cessation
- 1988-02-24 DK DK097388A patent/DK97388A/da not_active Application Discontinuation
- 1988-02-24 SE SE8800637A patent/SE504553C2/sv not_active IP Right Cessation
- 1988-02-24 NZ NZ223621A patent/NZ223621A/en unknown
- 1988-02-24 PT PT86821A patent/PT86821B/pt not_active IP Right Cessation
- 1988-02-25 LU LU87143A patent/LU87143A1/fr unknown
- 1988-02-25 BE BE8800219A patent/BE1002115A3/fr not_active IP Right Cessation
- 1988-02-25 YU YU36488A patent/YU46781B/sh unknown
-
1992
- 1992-10-20 CN CN92111551A patent/CN1030077C/zh not_active Expired - Fee Related
-
1993
- 1993-03-24 SE SE9300976A patent/SE503201C2/sv not_active IP Right Cessation
- 1993-03-24 SE SE9300977A patent/SE512485C2/sv not_active IP Right Cessation
-
1997
- 1997-10-06 DK DK113897A patent/DK113897A/da not_active Application Discontinuation
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