OA11112A - Process for preparing 2-azadihydroxybicycloÄ2.2.1Üheptane compounds and the l-tartaric acid salt of the compound - Google Patents

Process for preparing 2-azadihydroxybicycloÄ2.2.1Üheptane compounds and the l-tartaric acid salt of the compound Download PDF

Info

Publication number: OA11112A
Authority: OA; OAPI
Prior art keywords: compound; formula; mol; azadihydroxybicyclo; diastereomer
Prior art date: 1996-10-16

Application number

OA9900080A

Other languages

English (en)

Inventor

Thierry Durand

Denis Largeau

Patrick Leon

Michael O'brien

Matthew Powers

Original Assignee

Rhone Poulenc Rorer Pharma

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.)

1996-10-16

Filing date

1999-04-09

Publication date

2003-04-04

1999-04-09 Application filed by Rhone Poulenc Rorer Pharma filed Critical Rhone Poulenc Rorer Pharma

2003-04-04 Publication of OA11112A publication Critical patent/OA11112A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 38
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 title claims abstract description 24
238000004519 manufacturing process Methods 0.000 title description 2
-1 heptane compound Chemical class 0.000 claims abstract description 48
238000000034 method Methods 0.000 claims abstract description 43
239000001257 hydrogen Substances 0.000 claims abstract description 38
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims abstract description 36
239000002253 acid Substances 0.000 claims abstract description 28
239000012285 osmium tetroxide Substances 0.000 claims abstract description 18
229910000489 osmium tetroxide Inorganic materials 0.000 claims abstract description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
239000007800 oxidant agent Substances 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
230000001590 oxidative effect Effects 0.000 claims abstract description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 10
WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims abstract description 10
230000001172 regenerating effect Effects 0.000 claims abstract description 6
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
125000006239 protecting group Chemical group 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical group CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000003435 aroyl group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims description 3
239000003791 organic solvent mixture Substances 0.000 claims description 3
229910052762 osmium Inorganic materials 0.000 claims description 3
239000011975 tartaric acid Substances 0.000 claims description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 2
235000002906 tartaric acid Nutrition 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 abstract description 22
229910052751 metal Inorganic materials 0.000 abstract 1
239000002184 metal Substances 0.000 abstract 1
239000000047 product Substances 0.000 description 46
239000000243 solution Substances 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
238000003756 stirring Methods 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
239000007787 solid Substances 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
238000001914 filtration Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
239000010410 layer Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
150000003951 lactams Chemical class 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
150000007524 organic acids Chemical class 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
230000003647 oxidation Effects 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
NGAZZOYFWWSOGK-UHFFFAOYSA-N ethyl-n-butyl-ketone Natural products CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 5
USBJLGXPMPMTSL-UHFFFAOYSA-N heptan-3-one Chemical compound [CH2]CC(=O)CCCC USBJLGXPMPMTSL-UHFFFAOYSA-N 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
235000005985 organic acids Nutrition 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 5
239000000126 substance Substances 0.000 description 5
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000007858 starting material Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
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 3
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
239000007832 Na2SO4 Substances 0.000 description 3
229940099408 Oxidizing agent Drugs 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
238000007327 hydrogenolysis reaction Methods 0.000 description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 2
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 2
LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000005708 Sodium hypochlorite Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000013019 agitation Methods 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
YAGCIXJCAUGCGI-UHFFFAOYSA-N butoxycarbonyl butyl carbonate Chemical compound CCCCOC(=O)OC(=O)OCCCC YAGCIXJCAUGCGI-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000002826 coolant 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
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
238000005907 ketalization reaction Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
LFMTUFVYMCDPGY-UHFFFAOYSA-N n,n-diethylethanamine oxide Chemical compound CC[N+]([O-])(CC)CC LFMTUFVYMCDPGY-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
229960001841 potassium permanganate Drugs 0.000 description 2
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 2
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
229960001367 tartaric acid Drugs 0.000 description 2
AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
VXXVUHAXJHEYFH-UAIGNFCESA-N (z)-but-2-enedioic acid;sodium Chemical compound [Na].[Na].OC(=O)\C=C/C(O)=O VXXVUHAXJHEYFH-UAIGNFCESA-N 0.000 description 1
ZQXSFZAMFNRZOQ-UHFFFAOYSA-N 2-methylpropan-2-ol;hydrate Chemical compound O.CC(C)(C)O ZQXSFZAMFNRZOQ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
238000005698 Diels-Alder reaction Methods 0.000 description 1
FDOZDQRGEXDWST-UHFFFAOYSA-N OC(=O)C(F)(F)F.CCNC(=O)C1CCCC1 Chemical compound OC(=O)C(F)(F)F.CCNC(=O)C1CCCC1 FDOZDQRGEXDWST-UHFFFAOYSA-N 0.000 description 1
AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
229910019891 RuCl3 Inorganic materials 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Chemical class CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
238000006359 acetalization reaction Methods 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000004849 alkoxymethyl group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229940045348 brown mixture Drugs 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 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
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
XUZLXCQFXTZASF-UHFFFAOYSA-N nitro(phenyl)methanol Chemical compound [O-][N+](=O)C(O)C1=CC=CC=C1 XUZLXCQFXTZASF-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229910000487 osmium oxide Inorganic materials 0.000 description 1
JIWAALDUIFCBLV-UHFFFAOYSA-N oxoosmium Chemical compound [Os]=O JIWAALDUIFCBLV-UHFFFAOYSA-N 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000003379 purinergic P1 receptor agonist Substances 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
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 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
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—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
- 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
- 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
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)

OA9900080A 1996-10-16 1999-04-09 Process for preparing 2-azadihydroxybicycloÄ2.2.1Üheptane compounds and the l-tartaric acid salt of the compound OA11112A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/732,024 US5684159A (en)	1995-05-30	1996-10-16	L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds

Publications (1)

Publication Number	Publication Date
OA11112A true OA11112A (en)	2003-04-04

Family

ID=24941881

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900080A OA11112A (en)	1996-10-16	1999-04-09	Process for preparing 2-azadihydroxybicycloÄ2.2.1Üheptane compounds and the l-tartaric acid salt of the compound

Country Status (21)

Country	Link
US (4)	US5684159A (cs)
EP (1)	EP0934268A4 (cs)
JP (1)	JP2001502329A (cs)
KR (1)	KR20000049195A (cs)
CN (2)	CN1094927C (cs)
AP (1)	AP942A (cs)
AU (1)	AU721965B2 (cs)
BG (2)	BG64701B1 (cs)
BR (1)	BR9711910A (cs)
CA (1)	CA2268652A1 (cs)
CZ (1)	CZ291387B6 (cs)
EA (3)	EA200100661A1 (cs)
HU (1)	HUP9903583A3 (cs)
IL (1)	IL129231A (cs)
NO (2)	NO320332B1 (cs)
OA (1)	OA11112A (cs)
PL (1)	PL332827A1 (cs)
SK (1)	SK43799A3 (cs)
UA (1)	UA52702C2 (cs)
WO (1)	WO1998016510A1 (cs)
ZA (1)	ZA979268B (cs)

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US5684159A (en) *	1995-05-30	1997-11-04	Rhone-Poulenc Rorer S.A.	L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds
EP1146040B1 (en) *	1997-12-25	2006-11-29	Kuraray Co., Ltd.	Method of crystallizing 2-azabicyclo(2.2.1)hept-5-en-3-one
TW396337B (en) *	1998-02-13	2000-07-01	Mediatek Inc	The automatic regulating device of cdrom optimum focusing spot and the method thereof
US5952339A (en) *	1998-04-02	1999-09-14	Bencherif; Merouane	Pharmaceutical compositions and methods of using nicotinic antagonists for treating a condition or disorder characterized by alteration in normal neurotransmitter release
US5986100A (en) *	1998-04-02	1999-11-16	Crooks; Peter Anthony	Pharmaceutical compositions and methods for use
US6057446A (en)	1998-04-02	2000-05-02	Crooks; Peter Anthony	Certain 1-aza-tricyclo [3.3.1-13,7 ] decane compounds
PT1140933E (pt)	1998-12-31	2004-12-31	Aventis Pharma Inc	Processo para preparar derivados n6-substituidos de desaza-adenosina
US6387033B1 (en) *	2000-11-22	2002-05-14	Council Of Scientific And Industrial Research	Preparation of new layered double hydroxides exchanged with osmate for asymmetric dihydroxylation of olefins to vicinal diols
WO2002091988A2 (en) *	2001-05-10	2002-11-21	Aventis Pharma Deutschland Gmbh	Novel processes for the preparation of adenosine compounds and intermediates thereto
EP1574508A1 (de) *	2004-01-30	2005-09-14	Lonza AG	Verfahren zur Herstellung von Acetalen und Ketalen von 3-Amino-5-(hydroxymethyl)-cyclopentan-1,2-diolen, sowie deren Derivaten und Salzen
ATE537148T1 (de) *	2006-10-11	2011-12-15	Nippon Soda Co	Verfahren zur herstellung eines azabicycloalkanolderivats
CN102311440B (zh) *	2010-07-02	2015-01-07	无锡药明康德生物技术有限公司	1-甲氧羰基-3-苄基-8-叔丁氧羰基-3,8-二氮杂双环[3.2.1]辛烷及制备方法

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NL7513818A (nl) *	1974-12-13	1976-06-15	Merck & Co Inc	Werkwijze voor het scheiden van enantiomere 1-tert.butylamino 2.3-dihydroxypropanen.
US4508911A (en) *	1982-06-21	1985-04-02	The Upjohn Company	Amine intermediates for analgesic compounds
US5284769A (en) *	1989-10-16	1994-02-08	Chiros Ltd.	Process for preparing a single enantiomer of a lactam using lactamase
CA2032124A1 (en) *	1989-12-13	1991-06-14	Theunis G. Fourie	Polycyclic nitrile compounds and pharmaceutical compositions thereof
JP2891740B2 (ja) *	1990-03-30	1999-05-17	塩野義製薬株式会社	光学活性ノルボルナン系アミン誘導体の製造方法
SG80526A1 (en) *	1990-09-25	2001-05-22	Rhone Poulenc Rorer Int	Compounds having antihypertensive and anti- ischemic properies
US5700895A (en) *	1993-08-23	1997-12-23	Sumitomo Chemical Company, Limited	Ethylene-α-olefin copolymer and molded article thereof
US5684159A (en) *	1995-05-30	1997-11-04	Rhone-Poulenc Rorer S.A.	L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds
FR2734822B1 (fr) *	1995-05-30	1997-07-04	Rhone Poulenc Rorer Sa	Nouveaux derives du 2-azabicyclo(2.2.1)heptane, leur preparation et leur application
US5670649A (en) *	1995-05-30	1997-09-23	Rhone-Poulenc Rorer S.A.	Derivatives of 2-azabicyclo 2.2.1!heptane, their preparation and their application
US5856497A (en) *	1995-12-11	1999-01-05	Boehringer Ingelheim Pharmaceuticals, Inc.	Asymmetric synthesis of α-cycloalkylalkyl substituted methanamines

1996
- 1996-10-16 US US08/732,024 patent/US5684159A/en not_active Expired - Fee Related
1997
- 1997-06-10 US US08/873,096 patent/US5886192A/en not_active Expired - Fee Related
- 1997-06-10 US US08/873,284 patent/US5831096A/en not_active Expired - Fee Related
- 1997-06-10 US US08/873,285 patent/US5808093A/en not_active Expired - Fee Related
- 1997-10-15 CA CA002268652A patent/CA2268652A1/en not_active Abandoned
- 1997-10-15 AP APAP/P/1999/001486A patent/AP942A/en active
- 1997-10-15 EP EP97910894A patent/EP0934268A4/en not_active Withdrawn
- 1997-10-15 UA UA99052680A patent/UA52702C2/uk unknown
- 1997-10-15 JP JP10518472A patent/JP2001502329A/ja not_active Ceased
- 1997-10-15 CN CN97198783A patent/CN1094927C/zh not_active Expired - Fee Related
- 1997-10-15 HU HU9903583A patent/HUP9903583A3/hu unknown
- 1997-10-15 EA EA200100661A patent/EA200100661A1/ru unknown
- 1997-10-15 EA EA199900382A patent/EA002438B1/ru not_active IP Right Cessation
- 1997-10-15 WO PCT/US1997/018365 patent/WO1998016510A1/en not_active Ceased
- 1997-10-15 AU AU48160/97A patent/AU721965B2/en not_active Ceased
- 1997-10-15 CZ CZ19991312A patent/CZ291387B6/cs not_active IP Right Cessation
- 1997-10-15 KR KR1019990703293A patent/KR20000049195A/ko not_active Abandoned
- 1997-10-15 BR BR9711910A patent/BR9711910A/pt not_active Application Discontinuation
- 1997-10-15 EA EA200100660A patent/EA200100660A1/ru unknown
- 1997-10-15 SK SK437-99A patent/SK43799A3/sk unknown
- 1997-10-15 PL PL97332827A patent/PL332827A1/xx not_active IP Right Cessation
- 1997-10-15 IL IL12923197A patent/IL129231A/xx unknown
- 1997-10-16 ZA ZA979268A patent/ZA979268B/xx unknown
1999
- 1999-03-30 BG BG103296A patent/BG64701B1/bg unknown
- 1999-03-30 BG BG108906A patent/BG64733B1/bg unknown
- 1999-04-09 OA OA9900080A patent/OA11112A/en unknown
- 1999-04-15 NO NO19991800A patent/NO320332B1/no unknown
2002
- 2002-06-05 CN CN02122409A patent/CN1385422A/zh active Pending
2005
- 2005-04-08 NO NO20051757A patent/NO20051757D0/no unknown

Also Published As

Publication number	Publication date
BG103296A (en)	2000-11-30
AP9901486A0 (en)	1999-03-31
HUP9903583A2 (hu)	2000-04-28
HK1022475A1 (en)	2000-08-11
NO991800D0 (no)	1999-04-15
EP0934268A4 (en)	2001-04-18
BR9711910A (pt)	1999-08-24
US5808093A (en)	1998-09-15
AP942A (en)	2001-02-16
SK43799A3 (en)	2000-04-10
IL129231A0 (en)	2000-02-17
US5684159A (en)	1997-11-04
EA200100661A1 (ru)	2001-12-24
EP0934268A1 (en)	1999-08-11
EA002438B1 (ru)	2002-04-25
ZA979268B (en)	1998-07-27
BG64701B1 (bg)	2005-12-30
NO991800L (no)	1999-06-15
CZ131299A3 (cs)	2000-06-14
KR20000049195A (ko)	2000-07-25
IL129231A (en)	2003-07-06
AU4816097A (en)	1998-05-11
CN1094927C (zh)	2002-11-27
BG64733B1 (bg)	2006-01-31
NO20051757D0 (no)	2005-04-08
US5886192A (en)	1999-03-23
EA199900382A1 (ru)	1999-10-28
UA52702C2 (uk)	2003-01-15
CN1385422A (zh)	2002-12-18
CZ291387B6 (cs)	2003-02-12
WO1998016510A1 (en)	1998-04-23
NO20051757L (no)	1999-06-15
CN1233239A (zh)	1999-10-27
AU721965B2 (en)	2000-07-20
US5831096A (en)	1998-11-03
JP2001502329A (ja)	2001-02-20
CA2268652A1 (en)	1998-04-23
HUP9903583A3 (en)	2000-10-30
PL332827A1 (en)	1999-10-11
NO320332B1 (no)	2005-11-21
EA200100660A1 (ru)	2001-12-24

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IL200692A (en)	2011-11-30	Method of preparing a desired diastereomer of a tetrahydro-beta-carboline and use thereof for preparing an indole-1,4-dione derivative
OA11112A (en)	2003-04-04	Process for preparing 2-azadihydroxybicycloÄ2.2.1Üheptane compounds and the l-tartaric acid salt of the compound
US6184380B1 (en)	2001-02-06	Process for preparing naphthyridones and intermediates
WO1989000158A1 (en)	1989-01-12	Bridged-diazabicycloalkyl quinolone carboxylic acids and esters
JPH02292288A (ja)	1990-12-03	２，７‐ジアザビシクロ［３．３．０］オクタン類
JP2848538B2 (ja)	1999-01-20	２環性アミノ基で置換されたピリドンカルボン酸誘導体、そのエステルおよびその塩ならびにこれらの中間体たる２環性アミン
US5631383A (en)	1997-05-20	Derivatives of 2-azabicyclo[2.2.1]heptane, their preparation and their application
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US5912365A (en)	1999-06-15	Derivatives of 2-azabicyclo 2.2.1! heptane, their preparation and their application
DE69615020T2 (de)	2002-03-21	2-azabicyclo[2.2.1]heptan-derivate, ihre herstellung und ihre anwendung
CA1232280A (en)	1988-02-02	Bicyclic aminoacid intermediates, process for their preparation, agents containing these compounds and their use
US5929240A (en)	1999-07-27	Process and intermediates for preparing naphthyridonecarboxylic acid salts
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HK1051189A (en)	2003-07-25	Process for preparing 2-azadihydroxybicyclo[2.2.1]heptane compounds and the l-tartaric acid salt of the compound
HK1025318A (en)	2000-11-10	Process for preparing trovafloxacin acid salts
MXPA97008995A (en)	1998-10-15	New derivatives of 2-azabiciclo [2.2.1] heptano, its preparation and its application