NO320332B1 - Fremgangsmate ved fremstilling av 2-azadihydroksybicyklo [2.2.2]-heptanforbindelser samt L-tartarsyresalter av forbindelsene - Google Patents

Fremgangsmate ved fremstilling av 2-azadihydroksybicyklo [2.2.2]-heptanforbindelser samt L-tartarsyresalter av forbindelsene Download PDF

Info

Publication number: NO320332B1
Authority: NO; Norway
Prior art keywords: mol; azadihydroxybicyclo; heptane; formula; compound
Prior art date: 1996-10-16

Application number

NO19991800A

Other languages

English (en)

Norwegian (no)

Other versions

NO991800D0 (no

NO991800L (no

Inventor

Patrick Leon

Michael O'brien

Denis Largeau

Matthew Powers

Thierry Durand

Original Assignee

Aventis Pharma Inc

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

1999-04-15

Publication date

2005-11-21

1999-04-15 Application filed by Aventis Pharma Inc filed Critical Aventis Pharma Inc

1999-04-15 Publication of NO991800D0 publication Critical patent/NO991800D0/no

1999-06-15 Publication of NO991800L publication Critical patent/NO991800L/no

2005-11-21 Publication of NO320332B1 publication Critical patent/NO320332B1/no

Links

IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 title claims description 30
238000000034 method Methods 0.000 title claims description 27
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 description 19
238000002360 preparation method Methods 0.000 title claims description 13
150000001875 compounds Chemical class 0.000 title claims description 12
-1 heptane compound Chemical class 0.000 claims description 24
229910000489 osmium tetroxide Inorganic materials 0.000 claims description 22
239000012285 osmium tetroxide Substances 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical group CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 claims description 7
239000007800 oxidant agent Substances 0.000 claims description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
230000001172 regenerating effect Effects 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000003791 organic solvent mixture Substances 0.000 claims description 3
239000011877 solvent mixture Substances 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
239000000203 mixture Substances 0.000 description 17
150000003839 salts Chemical class 0.000 description 14
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
150000007524 organic acids Chemical class 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 4
235000005985 organic acids Nutrition 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000003513 alkali Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000006243 chemical reaction Methods 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
125000000753 cycloalkyl group Chemical group 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 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
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 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
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000008098 formaldehyde solution Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
239000011707 mineral Substances 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
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229910052762 osmium Inorganic materials 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000002390 rotary evaporation Methods 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 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
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 1
DJFRYQWIMHWWIP-LREBCSMRSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;heptane Chemical compound CCCCCCC.OC(=O)[C@H](O)[C@@H](O)C(O)=O DJFRYQWIMHWWIP-LREBCSMRSA-N 0.000 description 1
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
XVKXOQWFJYJRSK-UHFFFAOYSA-N 2,3-dimethoxybutanedioic acid Chemical compound COC(C(O)=O)C(OC)C(O)=O XVKXOQWFJYJRSK-UHFFFAOYSA-N 0.000 description 1
FTMADZLQESXXAW-UHFFFAOYSA-N 2-benzoyl-3-oxo-3-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(=O)O)C(=O)C1=CC=CC=C1 FTMADZLQESXXAW-UHFFFAOYSA-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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
238000005698 Diels-Alder reaction Methods 0.000 description 1
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 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-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
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001476 alcoholic effect Effects 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
239000012300 argon atmosphere Substances 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
239000002585 base Substances 0.000 description 1
150000007514 bases Chemical class 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
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229940045348 brown mixture Drugs 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 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
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 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
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
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000003287 optical effect Effects 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
239000012286 potassium permanganate Substances 0.000 description 1
239000002244 precipitate 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
238000000746 purification Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method 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
229910052708 sodium Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 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)

NO19991800A 1996-10-16 1999-04-15 Fremgangsmate ved fremstilling av 2-azadihydroksybicyklo [2.2.2]-heptanforbindelser samt L-tartarsyresalter av forbindelsene NO320332B1 (no)

Applications Claiming Priority (2)

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
PCT/US1997/018365 WO1998016510A1 (en)	1996-10-16	1997-10-15	Process for preparing 2-azadihydroxybicyclo[2.2.1]heptane compounds and the l-tartaric acid salt of the compound

Publications (3)

Publication Number	Publication Date
NO991800D0 NO991800D0 (no)	1999-04-15
NO991800L NO991800L (no)	1999-06-15
NO320332B1 true NO320332B1 (no)	2005-11-21

Family

ID=24941881

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO19991800A NO320332B1 (no)	1996-10-16	1999-04-15	Fremgangsmate ved fremstilling av 2-azadihydroksybicyklo [2.2.2]-heptanforbindelser samt L-tartarsyresalter av forbindelsene
NO20051757A NO20051757D0 (no)	1996-10-16	2005-04-08	Fremgangsmõte ved fremstilling av 2-azadihydroksybicyklo [2.2.2]-heptanforbindelser samt L-tartarsyresalter av forbindelsene

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO20051757A NO20051757D0 (no)	1996-10-16	2005-04-08	Fremgangsmõte ved fremstilling av 2-azadihydroksybicyklo [2.2.2]-heptanforbindelser samt L-tartarsyresalter av forbindelsene

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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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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CA2032124A1 (en) *	1989-12-13	1991-06-14	Theunis G. Fourie	Polycyclic nitrile compounds and pharmaceutical compositions thereof
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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
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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
OA11112A (en)	2003-04-04
CA2268652A1 (en)	1998-04-23
HUP9903583A3 (en)	2000-10-30
PL332827A1 (en)	1999-10-11
EA200100660A1 (ru)	2001-12-24

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