CA2246051A1 - Azabicyclic esters of carbamic acids useful in therapy - Google Patents

Azabicyclic esters of carbamic acids useful in therapy Download PDF

Info

Publication number: CA2246051A1
Authority: CA; Canada
Prior art keywords: formula; compound; ester; azabicyclo; octan
Prior art date: 1996-02-23
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA002246051A

Other languages

English (en)

French (fr)

Inventor

John Macor

Edwin Wu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

AstraZeneca AB

Original Assignee

Individual

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.)

1996-02-23

Filing date

1997-02-21

Publication date

1997-08-28

1997-02-21 Application filed by Individual filed Critical Individual

1997-08-28 Publication of CA2246051A1 publication Critical patent/CA2246051A1/en

Status Abandoned legal-status Critical Current

Links

238000002560 therapeutic procedure Methods 0.000 title abstract description 4
150000002148 esters Chemical class 0.000 title description 18
150000001715 carbamic acids Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 108
150000003839 salts Chemical class 0.000 claims abstract description 30
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
239000001257 hydrogen Substances 0.000 claims abstract description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
229910052736 halogen Inorganic materials 0.000 claims abstract description 21
239000000203 mixture Substances 0.000 claims abstract description 21
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 20
150000002367 halogens Chemical group 0.000 claims abstract description 19
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
-1 -OR5 Chemical group 0.000 claims abstract description 17
238000011321 prophylaxis Methods 0.000 claims abstract description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
229910052799 carbon Inorganic materials 0.000 claims abstract description 9
230000006735 deficit Effects 0.000 claims abstract description 9
150000002431 hydrogen Chemical group 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
238000011282 treatment Methods 0.000 claims abstract description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
208000028017 Psychotic disease Diseases 0.000 claims abstract description 5
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims abstract 7
239000002253 acid Substances 0.000 claims description 43
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 20
208000035475 disorder Diseases 0.000 claims description 16
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 13
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 12
239000012442 inert solvent Substances 0.000 claims description 11
229960002715 nicotine Drugs 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
239000012948 isocyanate Substances 0.000 claims description 7
150000002513 isocyanates Chemical class 0.000 claims description 7
229910000085 borane Inorganic materials 0.000 claims description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 5
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150000002540 isothiocyanates Chemical class 0.000 claims description 4
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 4
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208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 3
206010003805 Autism Diseases 0.000 claims description 3
208000020706 Autistic disease Diseases 0.000 claims description 3
208000020925 Bipolar disease Diseases 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 3
208000001456 Jet Lag Syndrome Diseases 0.000 claims description 3
206010026749 Mania Diseases 0.000 claims description 3
208000026139 Memory disease Diseases 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
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239000003085 diluting agent Substances 0.000 claims description 3
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239000001301 oxygen Substances 0.000 claims description 3
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PPPJULCFKXODES-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(4-cyanophenyl)carbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CC=C(C#N)C=C1 PPPJULCFKXODES-UHFFFAOYSA-N 0.000 claims description 2
SSLDFEPTWKCCLA-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(4-methoxyphenyl)carbamate Chemical compound C1=CC(OC)=CC=C1NC(=O)OC1C(CC2)CCN2C1 SSLDFEPTWKCCLA-UHFFFAOYSA-N 0.000 claims description 2
JEPJAGMRBZWMCT-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-phenylcarbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CC=CC=C1 JEPJAGMRBZWMCT-UHFFFAOYSA-N 0.000 claims description 2
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
239000012975 dibutyltin dilaurate Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 3
JRNNBGOEDTYSGH-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(3,4-dichlorophenyl)carbamate Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)OC1C(CC2)CCN2C1 JRNNBGOEDTYSGH-UHFFFAOYSA-N 0.000 claims 2
SLJMPDGIEKZJAU-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(4-bromophenyl)carbamate Chemical compound C1=CC(Br)=CC=C1NC(=O)OC1C(CC2)CCN2C1 SLJMPDGIEKZJAU-UHFFFAOYSA-N 0.000 claims 2
WVQQNNNYMPFHGO-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(4-methylphenyl)carbamate Chemical compound C1=CC(C)=CC=C1NC(=O)OC1C(CC2)CCN2C1 WVQQNNNYMPFHGO-UHFFFAOYSA-N 0.000 claims 2
208000024827 Alzheimer disease Diseases 0.000 claims 2
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208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
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208000025569 Tobacco Use disease Diseases 0.000 claims 2
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
208000015122 neurodegenerative disease Diseases 0.000 claims 2
208000027753 pain disease Diseases 0.000 claims 2
OLMKACMFPQRGRL-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptan-3-yl n-phenylcarbamate Chemical compound C1N(C2)CCC2C1OC(=O)NC1=CC=CC=C1 OLMKACMFPQRGRL-UHFFFAOYSA-N 0.000 claims 1
ONHFLIBNUOFXHA-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(3-methoxyphenyl)carbamate Chemical compound COC1=CC=CC(NC(=O)OC2C3CCN(CC3)C2)=C1 ONHFLIBNUOFXHA-UHFFFAOYSA-N 0.000 claims 1
NBDVCMQUQDOFRR-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-naphthalen-1-ylcarbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CC=CC2=CC=CC=C12 NBDVCMQUQDOFRR-UHFFFAOYSA-N 0.000 claims 1
RYDWZFYEYKGKQN-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-pyridin-2-ylcarbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CC=CC=N1 RYDWZFYEYKGKQN-UHFFFAOYSA-N 0.000 claims 1
IVUHKEGDYXRUHB-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-pyridin-4-ylcarbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CC=NC=C1 IVUHKEGDYXRUHB-UHFFFAOYSA-N 0.000 claims 1
SOGRRKOWZXEBMI-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-quinolin-3-ylcarbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CN=C(C=CC=C2)C2=C1 SOGRRKOWZXEBMI-UHFFFAOYSA-N 0.000 claims 1
JEPJAGMRBZWMCT-ZDUSSCGKSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-phenylcarbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)NC1=CC=CC=C1 JEPJAGMRBZWMCT-ZDUSSCGKSA-N 0.000 claims 1
JEPJAGMRBZWMCT-CYBMUJFWSA-N [(3s)-1-azabicyclo[2.2.2]octan-3-yl] n-phenylcarbamate Chemical compound O([C@H]1C2CCN(CC2)C1)C(=O)NC1=CC=CC=C1 JEPJAGMRBZWMCT-CYBMUJFWSA-N 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
230000005494 condensation Effects 0.000 claims 1
OVPWBKSJYFYQPC-UHFFFAOYSA-N o-(1-azabicyclo[2.2.2]octan-3-yl) n-phenylcarbamothioate Chemical compound C1N(CC2)CCC2C1OC(=S)NC1=CC=CC=C1 OVPWBKSJYFYQPC-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 5
238000003786 synthesis reaction Methods 0.000 abstract description 5
239000000543 intermediate Substances 0.000 abstract 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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239000011541 reaction mixture Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
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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 4
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PHVSUUGFGMGZPE-UHFFFAOYSA-N (4-bromophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(Br)C=C1 PHVSUUGFGMGZPE-UHFFFAOYSA-N 0.000 description 2
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SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
ULHIMEHJZGFPKJ-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(2-fluorophenyl)carbamate Chemical compound FC1=CC=CC=C1NC(=O)OC1C(CC2)CCN2C1 ULHIMEHJZGFPKJ-UHFFFAOYSA-N 0.000 description 1
QCWZYJPDPROWAC-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(3-chlorophenyl)carbamate Chemical compound ClC1=CC=CC(NC(=O)OC2C3CCN(CC3)C2)=C1 QCWZYJPDPROWAC-UHFFFAOYSA-N 0.000 description 1
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KHINMWCEXQIYHR-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(4-chlorophenyl)carbamate Chemical compound C1=CC(Cl)=CC=C1NC(=O)OC1C(CC2)CCN2C1 KHINMWCEXQIYHR-UHFFFAOYSA-N 0.000 description 1
CZQIJQFTRGDODI-UHFFFAOYSA-N 1-bromo-4-isocyanatobenzene Chemical compound BrC1=CC=C(N=C=O)C=C1 CZQIJQFTRGDODI-UHFFFAOYSA-N 0.000 description 1
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BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
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241001465754 Metazoa Species 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
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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
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000036592 analgesia Effects 0.000 description 1
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
229960000396 atropine Drugs 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
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210000004556 brain Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000000872 buffer Substances 0.000 description 1
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
229960004484 carbachol Drugs 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004296 chiral HPLC Methods 0.000 description 1
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238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
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PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
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238000007405 data analysis Methods 0.000 description 1
229910052805 deuterium Inorganic materials 0.000 description 1
MUCZHBLJLSDCSD-UHFFFAOYSA-N diisopropyl fluorophosphate Chemical compound CC(C)OP(F)(=O)OC(C)C MUCZHBLJLSDCSD-UHFFFAOYSA-N 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
229960005051 fluostigmine Drugs 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000003278 haem Chemical class 0.000 description 1
125000005241 heteroarylamino group Chemical group 0.000 description 1
230000000971 hippocampal effect Effects 0.000 description 1
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150000002466 imines Chemical class 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
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239000007788 liquid Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000012528 membrane Substances 0.000 description 1
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238000002156 mixing Methods 0.000 description 1
208000005264 motor neuron disease Diseases 0.000 description 1
239000000472 muscarinic agonist Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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230000003287 optical effect Effects 0.000 description 1
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
OUCYWJAACMAXQD-UHFFFAOYSA-N pyridin-2-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=N1 OUCYWJAACMAXQD-UHFFFAOYSA-N 0.000 description 1
FKSXRCPGQMOMBI-UHFFFAOYSA-N pyridin-4-ylcarbamic acid Chemical compound OC(=O)NC1=CC=NC=C1 FKSXRCPGQMOMBI-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000005586 smoking cessation Effects 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
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239000000725 suspension Substances 0.000 description 1
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239000000454 talc Substances 0.000 description 1
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235000002906 tartaric acid Nutrition 0.000 description 1
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150000003512 tertiary amines Chemical class 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Neurology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Medicinal Chemistry (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Addiction (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
Pain & Pain Management (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)

CA002246051A 1996-02-23 1997-02-21 Azabicyclic esters of carbamic acids useful in therapy Abandoned CA2246051A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
SE9600683A SE9600683D0 (sv)	1996-02-23	1996-02-23	Azabicyclic esters of carbamic acids useful in therapy
SE9600683-8		1996-02-23
PCT/SE1997/000294 WO1997030998A1 (en)	1996-02-23	1997-02-21	Azabicyclic esters of carbamic acids useful in therapy

Publications (1)

Publication Number	Publication Date
CA2246051A1 true CA2246051A1 (en)	1997-08-28

Family

ID=20401517

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002246051A Abandoned CA2246051A1 (en)	1996-02-23	1997-02-21	Azabicyclic esters of carbamic acids useful in therapy

Country Status (26)

Country	Link
US (2)	US5998429A (2)
EP (1)	EP0885221B1 (2)
JP (1)	JP2000505452A (2)
KR (1)	KR19990087184A (2)
CN (1)	CN1063749C (2)
AR (1)	AR005876A1 (2)
AT (1)	ATE219081T1 (2)
AU (1)	AU706944B2 (2)
BR (1)	BR9707616A (2)
CA (1)	CA2246051A1 (2)
CZ (1)	CZ289110B6 (2)
DE (1)	DE69713295T2 (2)
EE (1)	EE9800250A (2)
HU (1)	HUP9901273A3 (2)
ID (1)	ID15969A (2)
IL (2)	IL125620A (2)
IS (1)	IS4830A (2)
NO (1)	NO983711L (2)
NZ (1)	NZ331145A (2)
PL (1)	PL328614A1 (2)
RU (1)	RU2172739C2 (2)
SE (1)	SE9600683D0 (2)
SK (1)	SK102798A3 (2)
TR (1)	TR199801642T2 (2)
WO (1)	WO1997030998A1 (2)
ZA (1)	ZA971082B (2)

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US8914114B2 (en)	2000-05-23	2014-12-16	The Feinstein Institute For Medical Research	Inhibition of inflammatory cytokine production by cholinergic agonists and vagus nerve stimulation
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US6479510B2 (en)	2000-08-18	2002-11-12	Pharmacia & Upjohn Company	Quinuclidine-substituted aryl compounds for treatment of disease
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US6492385B2 (en)	2000-08-18	2002-12-10	Pharmacia & Upjohn Company	Quinuclidine-substituted heteroaryl moieties for treatment of disease
WO2002016355A2 (en) *	2000-08-21	2002-02-28	Pharmacia & Upjohn Company	Quinuclidine-substituted heteroaryl moieties for treatment of disease (nicotinic) acetylcholine receptor ligands
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AU2001282875A1 (en) *	2000-08-21	2002-03-04	Pharmacia And Upjohn Company	Quinuclidine-substituted heteroaryl moieties for treatment of disease
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AR036040A1 (es)	2001-06-12	2004-08-04	Upjohn Co	Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen
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JP2005504059A (ja) *	2001-08-24	2005-02-10	ファルマシアアンドアップジョンカンパニーリミティドライアビリティーカンパニー	疾患を処置するための置換アリール７−アザ［２．２．１］ビシクロヘプタン
DE60218493D1 (de) *	2001-09-12	2007-04-12	Pharmacia & Upjohn Co Llc	Substituierte 7-aza-ä2.2.1übicycloheptane für die behandlung von krankheiten
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CA2466375A1 (en)	2001-11-08	2003-05-15	Pharmacia & Upjohn Company	Azabicyclic-substituted-heteroaryl compounds for the treatment of disease
MXPA04004373A (es)	2001-11-09	2004-08-11	Upjohn Co	Compuestos heterociclicos condensados con fenilo azabiciclo para el tratamiento de enfermedades.
HUP0501017A3 (en)	2001-12-14	2010-06-28	Targacept	Methods and compositions for treatment of central nervous system disorders
DE10164139A1 (de)	2001-12-27	2003-07-10	Bayer Ag	2-Heteroarylcarbonsäureamide
EP1480977A2 (en)	2002-02-15	2004-12-01	PHARMACIA & UPJOHN COMPANY	Substituted aryl compounds for treatment of disease
CA2476681A1 (en) *	2002-02-19	2003-08-28	Bruce N. Rogers	Fused bicyclic-n-bridged-heteroaromatic carboxamides for the treatment of disease
CA2476624A1 (en) *	2002-02-19	2003-08-28	Pharmacia & Upjohn Company	Azabicyclic compounds for the treatment of disease
WO2003072578A1 (en) *	2002-02-20	2003-09-04	Pharmacia & Upjohn Company	Azabicyclic compounds with alfa7 nicotinic acetylcholine receptor activity
DE10211416A1 (de) *	2002-03-15	2003-09-25	Bayer Ag	Essig- und Propionsäureamide
DE10211415A1 (de) *	2002-03-15	2003-09-25	Bayer Ag	Bicyclische N-Biarylamide
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Publication number	Publication date
HUP9901273A3 (en)	2000-06-28
AU706944B2 (en)	1999-07-01
TR199801642T2 (xx)	1998-11-23
CZ265998A3 (cs)	2000-02-16
JP2000505452A (ja)	2000-05-09
EP0885221B1 (en)	2002-06-12
HK1017357A1 (en)	1999-11-19
IL137585A0 (en)	2001-07-24
NZ331145A (en)	2000-02-28
BR9707616A (pt)	1999-07-27
EP0885221A1 (en)	1998-12-23
PL328614A1 (en)	1999-02-01
WO1997030998A1 (en)	1997-08-28
IL125620A (en)	2001-09-13
CN1211983A (zh)	1999-03-24
US6054464A (en)	2000-04-25
DE69713295T2 (de)	2003-01-09
US5998429A (en)	1999-12-07
DE69713295D1 (de)	2002-07-18
AU2238797A (en)	1997-09-10
NO983711D0 (no)	1998-08-13
IL125620A0 (en)	1999-04-11
IS4830A (is)	1998-08-20
SK102798A3 (en)	1999-01-11
RU2172739C2 (ru)	2001-08-27
ID15969A (id)	1997-08-21
CN1063749C (zh)	2001-03-28
KR19990087184A (ko)	1999-12-15
ZA971082B (en)	1997-08-25
AR005876A1 (es)	1999-07-21
NO983711L (no)	1998-08-13
HUP9901273A2 (hu)	1999-07-28
CZ289110B6 (cs)	2001-11-14
ATE219081T1 (de)	2002-06-15
SE9600683D0 (sv)	1996-02-23
EE9800250A (et)	1999-02-15

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CA2246051A1 (en)	1997-08-28	Azabicyclic esters of carbamic acids useful in therapy
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CA2196995C (en)	2008-05-13	Spiro-azabicyclic compounds useful in therapy
AU2003224545B2 (en)	2009-08-13	Thienyl compounds
ZA200605027B (en)	2007-12-27	Nicotinic acetylcholine receptor ligands
CN100445285C (zh)	2008-12-24	烟碱性乙酰胆碱受体配体
HK1010370B (en)	2000-07-28	Spiro-azabicyclic compounds useful in therapy