HRP20100088T1 - Postupak priprave derivata tetrazola od organskih bor i organskih aluminij azida - Google Patents
Postupak priprave derivata tetrazola od organskih bor i organskih aluminij azida Download PDFInfo
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- HRP20100088T1 HRP20100088T1 HR20100088T HRP20100088T HRP20100088T1 HR P20100088 T1 HRP20100088 T1 HR P20100088T1 HR 20100088 T HR20100088 T HR 20100088T HR P20100088 T HRP20100088 T HR P20100088T HR P20100088 T1 HRP20100088 T1 HR P20100088T1
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- 238000000034 method Methods 0.000 title claims abstract 19
- 229910052796 boron Inorganic materials 0.000 title claims abstract 12
- 238000002360 preparation method Methods 0.000 title claims abstract 11
- 150000003536 tetrazoles Chemical class 0.000 title claims abstract 6
- -1 organo boron Chemical compound 0.000 title claims 7
- 125000002370 organoaluminium group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 40
- 229910052782 aluminium Chemical group 0.000 claims abstract 11
- 150000003839 salts Chemical class 0.000 claims abstract 11
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract 10
- 150000001540 azides Chemical class 0.000 claims abstract 5
- 125000002723 alicyclic group Chemical group 0.000 claims abstract 2
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract 2
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 7
- 238000002955 isolation Methods 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 3
- 125000005997 bromomethyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 230000000269 nucleophilic effect Effects 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims 1
- 229940126317 angiotensin II receptor antagonist Drugs 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- PBSPEQJOIRYRHU-UHFFFAOYSA-N azido(dibutyl)borane Chemical compound CCCCB(N=[N+]=[N-])CCCC PBSPEQJOIRYRHU-UHFFFAOYSA-N 0.000 claims 1
- SOXZLBKYJILYBM-UHFFFAOYSA-N azido(dicyclohexyl)borane Chemical compound C1CCCCC1B(N=[N+]=[N-])C1CCCCC1 SOXZLBKYJILYBM-UHFFFAOYSA-N 0.000 claims 1
- DQGZQAJIHKWEIU-UHFFFAOYSA-N azido(diethyl)alumane Chemical compound [N-]=[N+]=[N-].CC[Al+]CC DQGZQAJIHKWEIU-UHFFFAOYSA-N 0.000 claims 1
- ABCYVPTWWXZRBV-UHFFFAOYSA-N azido(diethyl)borane Chemical compound CCB(CC)N=[N+]=[N-] ABCYVPTWWXZRBV-UHFFFAOYSA-N 0.000 claims 1
- MWMPSUHRZSGXIO-UHFFFAOYSA-N azido(dimethyl)alumane Chemical compound C[Al+]C.[N-]=[N+]=[N-] MWMPSUHRZSGXIO-UHFFFAOYSA-N 0.000 claims 1
- OIQMKWGYLILBKD-UHFFFAOYSA-N azido(diphenyl)borane Chemical compound C=1C=CC=CC=1B(N=[N+]=[N-])C1=CC=CC=C1 OIQMKWGYLILBKD-UHFFFAOYSA-N 0.000 claims 1
- HVSQIYXWVABOJJ-UHFFFAOYSA-N azido(dipropyl)borane Chemical compound CCCB(CCC)N=[N+]=[N-] HVSQIYXWVABOJJ-UHFFFAOYSA-N 0.000 claims 1
- HPCKBIRWBBMNTK-UHFFFAOYSA-N azido-bis(2-methylpropyl)borane Chemical compound CC(C)CB(CC(C)C)N=[N+]=[N-] HPCKBIRWBBMNTK-UHFFFAOYSA-N 0.000 claims 1
- YUGZSAQRWBVQJN-UHFFFAOYSA-N azido-di(propan-2-yl)borane Chemical compound CC(C)B(C(C)C)N=[N+]=[N-] YUGZSAQRWBVQJN-UHFFFAOYSA-N 0.000 claims 1
- HMTULCHRSAPXGU-UHFFFAOYSA-N bis(2-methylpropyl)alumanylium;azide Chemical compound CC(C)C[Al](CC(C)C)N=[N+]=[N-] HMTULCHRSAPXGU-UHFFFAOYSA-N 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- HOSFFWYIXMAFER-UHFFFAOYSA-N di(propan-2-yl)alumanylium;azide Chemical compound [N-]=[N+]=[N-].CC(C)[Al+]C(C)C HOSFFWYIXMAFER-UHFFFAOYSA-N 0.000 claims 1
- ZSTBDNYVSIKSIA-UHFFFAOYSA-N dibutylalumanylium;azide Chemical compound [N-]=[N+]=[N-].CCCC[Al+]CCCC ZSTBDNYVSIKSIA-UHFFFAOYSA-N 0.000 claims 1
- CXXRJSVONCZUJK-UHFFFAOYSA-N dicyclohexylalumanylium;azide Chemical compound [N-]=[N+]=[N-].C1CCCCC1[Al+]C1CCCCC1 CXXRJSVONCZUJK-UHFFFAOYSA-N 0.000 claims 1
- DCELNKRTTMTUKK-UHFFFAOYSA-N dipropylalumanylium;azide Chemical compound [N-]=[N+]=[N-].CCC[Al+]CCC DCELNKRTTMTUKK-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 125000005385 peroxodisulfate group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract
Postupak za pripravu tetrazola formuleili njegovog tautomera ili njegove soli, gdje R predstavlja organski ostatak; naznačen time, da obuhvaća (i) reakciju spoja formule R-CN (II a) s azidom formule (R1)(R2)M-N3 (II b), gdje R ima značenje kao gore određeno; R1 i R2, neovisno jedan od drugoga, predstavljaju organski ostatak kao što je alifatski ostatak, aliciklički ostatak, heteroaliciklički ostatak; aliciklički-alifatski ostatak; heteroaliciklički-alifatski ostatak; karbociklički ili heterociklički aromatski ostatak; aralifatski ostatak ili heteroaralifatski ostatak, pri čemu je svaki ostatak, neovisno jedan od drugoga, nesupstituiran ili supstituiran; te M je bor ili aluminij; te (ii) izolaciju rezultirajućeg spoja formule (I). Patent sadrži još 17 patentnih zahtjeva.
Claims (18)
1. Postupak za pripravu tetrazola formule
[image]
ili njegovog tautomera ili njegove soli, gdje R predstavlja organski ostatak;
naznačen time, da obuhvaća
(i) reakciju spoja formule R-CN (II a) s azidom formule (R1)(R2)M-N3 (II b), gdje R ima značenje kao gore određeno; R1 i R2, neovisno jedan od drugoga, predstavljaju organski ostatak kao što je alifatski ostatak, aliciklički ostatak, heteroaliciklički ostatak; aliciklički-alifatski ostatak; heteroaliciklički-alifatski ostatak; karbociklički ili heterociklički aromatski ostatak; aralifatski ostatak ili heteroaralifatski ostatak, pri čemu je svaki ostatak, neovisno jedan od drugoga, nesupstituiran ili supstituiran; te M je bor ili aluminij;
te
(ii) izolaciju rezultirajućeg spoja formule (I).
2. Postupak u skladu sa zahtjevom 1 za pripravu antagonista angiotenzin II receptora koji ima strukturni oblik tetrazola formule (IV)
[image]
ili njegovog tautomernog oblika, gdje Rx predstavlja strukturni element izabran iz skupine koju čine
[image]
[image]
[image]
[image]
[image]
[image]
i
[image]
ili, u svakom slučaju, njegove soli;
naznačen time, da obuhvaća reakciju spoja formule (IV a)
[image]
gdje Rx ima značenje kao gore određeno,
sa spojem formule (R1)(R2)M-N3 (II b), gdje R1 i R2, neovisno jedan od drugoga, predstavljaju organski ostatak i M je aluminij ili bor; te izolaciju rezultirajućeg spoja formule (IV).
3. Postupak u skladu sa zahtjevom 1 za pripravu spoja formule (IV b)
[image]
naznačen time, da obuhvaća reakciju spoja formule (IV c)
[image]
ili njegovog estera s azidom formule (R1)(R2)M-N3 (II b), gdje R1 i R2, neovisno jedan od drugoga, predstavljaju organski ostatak i M je aluminij ili bor; te izolaciju spoja formule (IV b).
4. Postupak u skladu sa zahtjevom 1 za pripravu spoja formule
[image]
ili njegovog tautomernog oblika gdje Ry predstavlja C1-C8-alkil kao što je metil; C1-C8-alkil supstituiran s X' pri čemu X' je halogen, sulfoniloksi, hidroksil, zaštićeni hidroksil, kao što je bromometil, ili acetal formila;
naznačen time, da obuhvaća reakciju spoja formule (V a)
[image]
sa spojem formule (R1)(R2)M-N3 (II b), gdje R1 i R2, neovisno jedan od drugoga, predstavljaju organski ostatak i M je aluminij ili bor; te izolaciju rezultirajućeg spoja formule (V).
5. Postupak u skladu sa zahtjevom 1 za pripravu spoja formule
[image]
ili njegovog tautomera ili njegove soli, naznačen time, da obuhvaća
(a) tretiranje spoja formule (VI a)
[image]
gdje X predstavlja odlazeću skupinu, najprije sa nukleofilnim sredstvom i zatim sa „solvolitičkom“ bazom rezultirajući spojem formule (VI b)
[image]
(b) reakciju spoja formule (VI b) s azidom formule (R1)(R2)M-N3 (II b), gdje varijable R1 i R2, neovisno jedna od druge, te M, imaju značenja kao gore određeno; rezultirajući spojem formule (VI c)
[image]
ili njegovim tautomerom ili njegovom soli;
(c) oksidaciju spoja formule (VI c) ili njegovog tautomera ili njegove soli rezultirajući spojem formule (VI)
[image]
ili njegovim tautomerom ili njegovom soli; te
(d) izolaciju spoja formule (VI) ili njegovog tautomera ili njegove soli.
6. Postupak u skladu sa zahtjevom 5, naznačen time, da se oksidacijski korak c provodi u prisutnosti oksidacijskog sredstva izabranog iz skupine koju čine HNO2, HNO3 ili njihovi odgovarajući anhidridi, te peroksodisulfat, te pri čemu se kao otapalo koristi alklilirano aromatsko ugljikovodikovo otapalo kao što je toluen.
7. Postupak za pripravu tetrazola formule I, ili njegovog tautomera ili njegove soli, u skladu sa zahtjevom 1, naznačen time, da obuhvaća:
(i) reakciju spoja formule R-CN (II a), gdje R sadrži zaštićenu reaktivnu skupinu, s azidom formule R1R2MN3 (II b), te
(ii) uklanjanje zaštine skupine s rezultirajućeg tetrazola formule (I), gdje F sadrži zaštićenu reaktivnu skupinu.
8. Postupak u skladu sa zahtjevom 7, naznačen time, da navedena reaktivna skupina je hidroksilna skupina.
9. Postupak u skladu sa zahtjevom 8, naznačen time, da navedena hidroksilna skupina je zaštićena tretiranjem sa spojem formule M'(R3)n (II d) gdje
M' predstavlja element skupina 1a, 2a, 3a i 4a Periodične tablice elemenata;
R3, neovisno jedan od drugoga, je vodik, odlazeća skupina kao što je halogen, NH2, C1-C8-alkil, C3-C7-cikloalkil, karbociklički aril, karbociklički aril-alkil, C1-C8-alkoksi;
indeks „n“ odgovara valenciji elementa M';
te R3 može samo predstavljati jednu odlazeću skupinu kao što je halogen.
10. Postupak u skladu sa zahtjevom 9, naznačen time, da M' je izabran iz skupine koju čine Li, Na, K, Mg, Ca, B, Al i Si.
11. Postupak u skladu s bilo kojim zahtjevom 1 ili 7 do 10 za pripravu spoja formule I ili njegovog tautomera ili njegove soli, naznačen time, da reagirajući spoj formule R-CN (II a) je formule (VI b)
[image]
ili njegova sol.
12. Postupak u skladu sa zahtjevom 11, naznačen time, da je spoj formule (VI b) pripravljen tretiranjem spoja formule (VI a)
[image]
gdje X predstavlja odlazeću skupinu, najprije s nukleofilnim sredstvom i zatim sa „solvolitičkom“ bazom.
13. Postupak u skladu sa zahtjevom 1 za pripravu spoja formule
[image]
njegovog tautomernog oblika, gdje Ry predstavlja C1-C8-alkil ili C1-C8-alkil supstituiran s X' pri čemu X' je halogen, sulfoniloksi, hidroksil, zaštićeni hidroksil, kao što je bromometil, ili acetal formila;
naznačen time, da obuhvaća reakciju spoja formule (VII a')
[image]
sa spojem formule (R1)(R2)M-N3 (II b), gdje R1 i R2, neovisno jedan od drugoga, predstavljaju organski ostatak i M je aluminij ili bor; te izolaciju rezultirajućeg spoja formule (VII').
14. Postupak u skladu sa zahtjevom 1 za pripravu spoja formule
[image]
njegovog tautomernog oblika, gdje Ry predstavlja C1-C8-alkil kao što je metil; C1-C8-alkil supstituiran s X' pri čemu X' je halogen, sulfoniloksi, hidroksil, zaštićeni hidroksil, kao što je bromometil, formil ili njegov acetal;
naznačen time, da obuhvaća reakciju spoja formule (VII a)
[image]
sa spojem formule (R1)(R2)M-N3 (II b), gdje R1 i R2, neovisno jedan od drugoga, predstavljaju organski ostatak i M je aluminij ili bor; te izolaciju rezultirajućeg spoja formule (VII).
15. Postupak u skladu s bilo kojim zahtjevom 1 do 14, naznačen time, da se koristi spoj formule (R1)(R2)M-N3 (II b), gdje M je aluminij ili bor; te R1 i R2, neovisno jedan od drugoga, su C1-C8-alkil kao što je metil, etil, propil, diizobutil, terc.-butil ili n-oktil; C3-C7-alkenil kao što je alil ili krotil, C3-C7-cikloalkil kao što je cikloheksil; fenil-C1-C4-alkil kao što je benzil ili 2-fenetil; fenil-C3-C5-alkenil kao što je cinamil, ili C3-C8-cikloalkil-C1-C8-alkil kao što je ciklopropilmetil ili cikloheksilmetil.
16. Postupak u skladu s bilo kojim zahtjevom 1 do 14, naznačen time, da se koristi spoj formule (R1)(R2)M-N3 (II b), gdje M je aluminij ili bor; te R1 i R2, neovisno jedan od drugoga, su C1-C8-alkil, C3-C8-cikloalkil, C3-C8-cikloalkil-C1-C8-alkil ili aril-C1-C8-alkil.
17. Postupak u skladu s bilo kojim zahtjevom 1 do 14, naznačen time, da spoj formule (II b) je izabran iz skupine koju čine: dimetil aluminij azid, dietil aluminij azid, diizopropil aluminij azid, dipropil aluminij azid, diizobutil aluminij azid, dibutil aluminij azid, dicikloheksil aluminij azid, dietil bor azid, diizopropil bor azid, dipropil bor azid, diizobutil bor azid, dibutil bor azid, dicikloheksil bor azid i difenil bor azid.
18. Spoj, naznačen time, da je formule (R1)(R2)M-N3 (II b), gdje M je aluminij ili bor; te R1 i R2, neovisno jedan od drugoga, su C3-C7-alkenil kao što je alil ili krotil, C3-C7-cikloalkil kao što je cikloheksil; fenil-C1-C4-alkil kao što je benzil ili 2-fenetil; fenil-C3-C5-alkenil kao što je cinamil, ili C3-C8-cikloalkil-C1-C8-alkil kao što je ciklopropilmetil ili cikloheksilmetil.
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PCT/EP2004/007980 WO2005014602A1 (en) | 2003-07-15 | 2004-07-15 | Process for the preparation of tetrazole derivatives from organo boron and organo aluminium azides |
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GB0514206D0 (en) * | 2005-07-11 | 2005-08-17 | Novartis Ag | Organic compounds |
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CN101200455B (zh) * | 2007-09-29 | 2010-08-18 | 泰兴市江神化工有限公司 | 沙坦类治疗高血压药物主环5-(4'-甲酰基联苯-2-基)-1h-四氮唑的制备方法 |
JP4792128B2 (ja) | 2007-10-12 | 2011-10-12 | アークル インコーポレイテッド | 癌に対するhsp90阻害剤としての5−(2−ヒドロキシフェニル)テトラゾール |
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CN102712606A (zh) * | 2009-11-17 | 2012-10-03 | 田边三菱制药株式会社 | 联苯基衍生物的制备方法 |
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KR101942064B1 (ko) * | 2011-04-25 | 2019-01-24 | 주식회사 엘지화학 | 신규한 아연 아지드 착물 및 이를 이용한 테트라졸 유도체의 제조방법 |
CN102351804B (zh) * | 2011-09-30 | 2013-07-31 | 浙江新赛科药业有限公司 | 一种缬沙坦消旋体的回收方法 |
CN102702117B (zh) * | 2012-06-01 | 2016-04-13 | 浙江沙星医药化工有限公司 | 一种制备5-(4’-溴代甲基-2-联苯基)-1-三苯甲基四氮唑的方法 |
CN103265560B (zh) * | 2013-05-17 | 2016-05-04 | 中国科学院上海高等研究院 | 棉酚/棉酮衍生物及其制备方法和抗肿瘤药物中的应用 |
KR101956281B1 (ko) * | 2013-08-13 | 2019-03-08 | 삼성전기주식회사 | 수지 조성물, 이를 이용한 인쇄회로기판 및 그 제조방법 |
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