BG63084B1 - Нови производни на 2-азабицикло/2.2.1/хептан,получаване и приложение - Google Patents

Нови производни на 2-азабицикло/2.2.1/хептан,получаване и приложение Download PDF

Info

Publication number: BG63084B1
Authority: BG; Bulgaria
Prior art keywords: general formula; radical; substance; carbon atoms; radicals
Prior art date: 1995-05-30

Application number

BG102081A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG102081A (en

Inventor

Denis Largeau

Patrick Leon

Original Assignee

Rhone-Poulenc Rorer S.A.

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.)

1995-05-30

Filing date

1997-11-28

Publication date

2001-03-30

1995-05-30 Priority claimed from FR9506353A external-priority patent/FR2734822B1/fr

1997-11-28 Application filed by Rhone-Poulenc Rorer S.A. filed Critical Rhone-Poulenc Rorer S.A.

1998-11-30 Publication of BG102081A publication Critical patent/BG102081A/xx

2001-03-30 Publication of BG63084B1 publication Critical patent/BG63084B1/bg

Links

238000002360 preparation method Methods 0.000 title claims abstract description 8
GYLMCBOAXJVARF-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptane Chemical class C1C2CCC1NC2 GYLMCBOAXJVARF-UHFFFAOYSA-N 0.000 title claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 41
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 35
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 8
239000000126 substance Substances 0.000 claims description 77
-1 alkyl radical Chemical class 0.000 claims description 50
150000003254 radicals Chemical group 0.000 claims description 35
125000006239 protecting group Chemical group 0.000 claims description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
238000005984 hydrogenation reaction Methods 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
230000033444 hydroxylation Effects 0.000 claims description 5
238000005805 hydroxylation reaction Methods 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
230000003647 oxidation Effects 0.000 claims description 5
238000007254 oxidation reaction Methods 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
LFMTUFVYMCDPGY-UHFFFAOYSA-N n,n-diethylethanamine oxide Chemical compound CC[N+]([O-])(CC)CC LFMTUFVYMCDPGY-UHFFFAOYSA-N 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
239000012286 potassium permanganate Substances 0.000 claims description 3
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
150000003951 lactams Chemical class 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
229910001925 ruthenium oxide Inorganic materials 0.000 claims description 2
WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 2
238000000034 method Methods 0.000 claims 9
125000004433 nitrogen atom Chemical group N* 0.000 claims 6
125000001931 aliphatic group Chemical group 0.000 claims 4
230000021736 acetylation Effects 0.000 claims 1
238000006640 acetylation reaction Methods 0.000 claims 1
230000000694 effects Effects 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000012285 osmium tetroxide Substances 0.000 claims 1
229910000489 osmium tetroxide Inorganic materials 0.000 claims 1
229910052763 palladium Inorganic materials 0.000 claims 1
239000003379 purinergic P1 receptor agonist Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000001228 spectrum Methods 0.000 description 9
238000001914 filtration Methods 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 7
238000003756 stirring Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
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 5
239000012074 organic phase Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052720 vanadium Inorganic materials 0.000 description 5
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 4
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000005708 Sodium hypochlorite Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
229910052762 osmium Inorganic materials 0.000 description 3
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
239000013543 active substance Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000010908 decantation Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
KPFWYFYRULFDQP-UHFFFAOYSA-N 5-azabicyclo[2.2.1]hept-2-ene Chemical compound C1C2CNC1C=C2 KPFWYFYRULFDQP-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
238000005698 Diels-Alder reaction Methods 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
238000006359 acetalization reaction Methods 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
WOBLPDAWNVAVAS-UHFFFAOYSA-N butyl carboxy carbonate Chemical compound CCCCOC(=O)OC(O)=O WOBLPDAWNVAVAS-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
239000008098 formaldehyde solution Substances 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
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
QLLIPBVYTKAGER-UHFFFAOYSA-N n-ethyl-2,3-dihydroxycyclopentane-1-carboxamide Chemical compound CCNC(=O)C1CCC(O)C1O QLLIPBVYTKAGER-UHFFFAOYSA-N 0.000 description 1
125000006502 nitrobenzyl group Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000010926 purge Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
JGKYCLQDFDRUQJ-UHFFFAOYSA-N tert-butyl 2-oxo-3-azabicyclo[2.2.1]heptane-3-carboxylate Chemical compound C1CC2C(=O)N(C(=O)OC(C)(C)C)C1C2 JGKYCLQDFDRUQJ-UHFFFAOYSA-N 0.000 description 1
AJYDSJWVRJUFMI-UHFFFAOYSA-N tert-butyl 3-azabicyclo[2.2.1]heptane-3-carboxylate Chemical compound C1CC2N(C(=O)OC(C)(C)C)CC1C2 AJYDSJWVRJUFMI-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

BG102081A 1995-05-30 1997-11-28 Нови производни на 2-азабицикло/2.2.1/хептан,получаване и приложение BG63084B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9506353A FR2734822B1 (fr)	1995-05-30	1995-05-30	Nouveaux derives du 2-azabicyclo(2.2.1)heptane, leur preparation et leur application
PCT/FR1996/000793 WO1996038447A1 (fr)	1995-05-30	1996-05-28	Derives du 2-azabicyclo[2.2.1]heptane, leur preparation et leur application

Publications (2)

Publication Number	Publication Date
BG102081A BG102081A (en)	1998-11-30
BG63084B1 true BG63084B1 (bg)	2001-03-30

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ID=9479463

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Application Number	Title	Priority Date	Filing Date
BG102081A BG63084B1 (bg)	1995-05-30	1997-11-28	Нови производни на 2-азабицикло/2.2.1/хептан,получаване и приложение

Country Status (25)

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EP (1)	EP0828740B1 (da)
JP (2)	JP4097287B2 (da)
KR (1)	KR100488393B1 (da)
CN (1)	CN1249034C (da)
AP (1)	AP973A (da)
AT (1)	ATE205210T1 (da)
AU (1)	AU711057B2 (da)
BG (1)	BG63084B1 (da)
BR (1)	BR9608513A (da)
CA (1)	CA2219456A1 (da)
CZ (1)	CZ286483B6 (da)
DE (1)	DE69615020T2 (da)
DK (1)	DK0828740T3 (da)
EA (1)	EA000963B1 (da)
ES (1)	ES2163023T3 (da)
GR (1)	GR3036536T3 (da)
HU (1)	HUP9900787A3 (da)
NO (1)	NO311431B1 (da)
OA (1)	OA10543A (da)
PL (1)	PL186195B1 (da)
PT (1)	PT828740E (da)
RO (1)	RO119414B1 (da)
SI (1)	SI0828740T1 (da)
SK (1)	SK283809B6 (da)
UA (1)	UA64695C2 (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0719719A (ja) *	1993-07-05	1995-01-20	Matsushita Electric Ind Co Ltd	断熱箱体

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4954504A (en) *	1986-11-14	1990-09-04	Ciba-Geigy Corporation	N9 -cyclopentyl-substituted adenine derivatives having adenosine-2 receptor stimulating activity
US5063233A (en) *	1986-11-14	1991-11-05	Ciba-Geigy Corporation	N9 -cyclopentyl-substituted adenine derivatives useful as adenosine receptor agonists
US4803272A (en) *	1987-02-24	1989-02-07	E. I. Du Pont De Nemours And Company	S-modified adenosyl-1,8-diamino-3-thiooctane derivatives
US5561134A (en) *	1990-09-25	1996-10-01	Rhone-Poulenc Rorer Pharmaceuticals Inc.	Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties
GB9301000D0 (en) *	1993-01-20	1993-03-10	Glaxo Group Ltd	Chemical compounds

1996
- 1996-05-28 AU AU60087/96A patent/AU711057B2/en not_active Ceased
- 1996-05-28 EA EA199700440A patent/EA000963B1/ru not_active IP Right Cessation
- 1996-05-28 RO RO97-02201A patent/RO119414B1/ro unknown
- 1996-05-28 SI SI9630340T patent/SI0828740T1/xx unknown
- 1996-05-28 ES ES96917555T patent/ES2163023T3/es not_active Expired - Lifetime
- 1996-05-28 DE DE69615020T patent/DE69615020T2/de not_active Expired - Lifetime
- 1996-05-28 SK SK1612-97A patent/SK283809B6/sk not_active IP Right Cessation
- 1996-05-28 PT PT96917555T patent/PT828740E/pt unknown
- 1996-05-28 BR BR9608513A patent/BR9608513A/pt not_active IP Right Cessation
- 1996-05-28 PL PL96323680A patent/PL186195B1/pl not_active IP Right Cessation
- 1996-05-28 UA UA97115616A patent/UA64695C2/uk unknown
- 1996-05-28 CZ CZ19973777A patent/CZ286483B6/cs not_active IP Right Cessation
- 1996-05-28 EP EP96917555A patent/EP0828740B1/fr not_active Expired - Lifetime
- 1996-05-28 HU HU9900787A patent/HUP9900787A3/hu unknown
- 1996-05-28 KR KR1019970708582A patent/KR100488393B1/ko not_active Expired - Fee Related
- 1996-05-28 AP APAP/P/1997/001149A patent/AP973A/en active
- 1996-05-28 DK DK96917555T patent/DK0828740T3/da active
- 1996-05-28 CA CA002219456A patent/CA2219456A1/fr not_active Abandoned
- 1996-05-28 AT AT96917555T patent/ATE205210T1/de active
- 1996-05-28 JP JP53624696A patent/JP4097287B2/ja not_active Expired - Fee Related
1997
- 1997-11-28 NO NO19975487A patent/NO311431B1/no not_active IP Right Cessation
- 1997-11-28 OA OA70143A patent/OA10543A/fr unknown
- 1997-11-28 BG BG102081A patent/BG63084B1/bg unknown
2001
- 2001-09-06 GR GR20010400676T patent/GR3036536T3/el unknown
2002
- 2002-02-20 CN CNB021046816A patent/CN1249034C/zh not_active Expired - Fee Related
2007
- 2007-07-09 JP JP2007179423A patent/JP2007262089A/ja active Pending

Also Published As

Publication number	Publication date
AP9701149A0 (en)	1998-01-31
PL323680A1 (en)	1998-04-14
RO119414B1 (ro)	2004-10-29
PL186195B1 (pl)	2003-11-28
CN1397549A (zh)	2003-02-19
JP2007262089A (ja)	2007-10-11
PT828740E (pt)	2002-02-28
JPH11505861A (ja)	1999-05-25
KR19990022103A (ko)	1999-03-25
MX9708995A (es)	1998-03-31
NO975487D0 (no)	1997-11-28
AP973A (en)	2001-06-08
GR3036536T3 (en)	2001-12-31
JP4097287B2 (ja)	2008-06-11
HUP9900787A3 (en)	2001-05-28
EA199700440A1 (ru)	1998-08-27
NO975487L (no)	1997-11-28
UA64695C2 (en)	2004-03-15
AU6008796A (en)	1996-12-18
CN1249034C (zh)	2006-04-05
ES2163023T3 (es)	2002-01-16
BR9608513A (pt)	1999-02-02
DE69615020D1 (de)	2001-10-11
SI0828740T1 (en)	2001-12-31
ATE205210T1 (de)	2001-09-15
CZ377797A3 (cs)	1998-03-18
CA2219456A1 (fr)	1996-12-05
DE69615020T2 (de)	2002-03-21
SK161297A3 (en)	1998-04-08
AU711057B2 (en)	1999-10-07
EA000963B1 (ru)	2000-08-28
BG102081A (en)	1998-11-30
OA10543A (fr)	2002-05-31
DK0828740T3 (da)	2002-12-02
NO311431B1 (no)	2001-11-26
CZ286483B6 (en)	2000-04-12
EP0828740B1 (fr)	2001-09-05
SK283809B6 (sk)	2004-02-03
HUP9900787A2 (hu)	1999-07-28
EP0828740A1 (fr)	1998-03-18
KR100488393B1 (ko)	2005-08-30

Publication	Publication Date	Title
Taylor et al.	1985	Thallium in organic synthesis. 68. A convenient synthesis of 2-phenylindoles from anilides
Grierson et al.	1983	2-Cyano Δ3 piperideines—IX: General strategies for the synthesis of corynanthé-strychnos type indole alkaloids
WO2021093846A1 (zh)	2021-05-20	新型四环杂环化合物及其药物用途
BG64701B1 (bg)	2005-12-30	Метод за получаване на 2-азадихидроксибицикло[2.2.1]хептаново съединение и сол на съединението и l-винена киселина
US5631383A (en)	1997-05-20	Derivatives of 2-azabicyclo[2.2.1]heptane, their preparation and their application
US5670649A (en)	1997-09-23	Derivatives of 2-azabicyclo 2.2.1!heptane, their preparation and their application
AP973A (en)	2001-06-08	2-Azabicyclo {2.2.1} heptane derivatives preparation and application thereof.
EP0539486B1 (fr)	1994-09-28	Procede de preparation de derives de streptogramines
MXPA97008995A (en)	1998-10-15	New derivatives of 2-azabiciclo [2.2.1] heptano, its preparation and its application
CN1185782A (zh)	1998-06-24	2－氮杂双环[2,2,1]庚烷的新衍生物,其制备和应用
CN119708112A (zh)	2025-03-28	一种黎芦属异甾体生物碱天然产物的合成方法
WO2024093091A1 (zh)	2024-05-10	一种海鞘素类化合物中间体的制备方法
FR2737208A1 (fr)	1997-01-31	Nouvelles fluorovindolines, precurseurs d'analogues de la vinblastine et de la vinorelbine,leurs procedes de preparation et leur utilisation comme medicament
Ostaszewski et al.	1995	Synthesis and structure of chiral diazacoronands derived from L-tartaric acid1
BE884828A (fr)	1981-02-19	Derives de naphtacene
JPH0156072B2 (da)	1989-11-28
EP1100799A1 (fr)	2001-05-23	Preparation de derives de la camptothecine et de la nothapodytine
JPH0316950B2 (da)	1991-03-06
JPS6314798A (ja)	1988-01-21	ステロイド誘導体及びその製造法