JPH07107048B2 - 新規の１，２，５，６−テトラヒドロピリジン−３−カルボキサアルデヒドロのオキシムの誘導体、それらの製造方法、それらの薬剤としての使用及びそれらを含有する組成物 - Google Patents

新規の１，２，５，６−テトラヒドロピリジン−３−カルボキサアルデヒドロのオキシムの誘導体、それらの製造方法、それらの薬剤としての使用及びそれらを含有する組成物

Info

Publication number: JPH07107048B2
Authority: JP; Japan
Prior art keywords: carbon atoms; compound; tetrahydropyridine; group; formula
Prior art date: 1987-08-21
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.): Expired - Fee Related

Application number

JP63203962A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6468356A (en

Inventor

ジュリオ・ガルリアーニ

フェルナンド−・バルツァギ

カルラ・ボネッティ

エミリオ・トーヤ

Original Assignee

ルセル−ユクラフ

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.)

1987-08-21

Filing date

1988-08-18

Publication date

1995-11-15

1988-08-18 Application filed by ルセル−ユクラフ filed Critical ルセル−ユクラフ

1989-03-14 Publication of JPS6468356A publication Critical patent/JPS6468356A/ja

1995-11-15 Publication of JPH07107048B2 publication Critical patent/JPH07107048B2/ja

2010-11-15 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 13
239000003814 drug Substances 0.000 title claims description 7
239000000203 mixture Substances 0.000 title description 20
238000002360 preparation method Methods 0.000 title description 3
QGMSPDCKGXYZNB-UHFFFAOYSA-N n-(1,2,3,6-tetrahydropyridin-5-ylmethylidene)hydroxylamine Chemical class ON=CC1=CCCNC1 QGMSPDCKGXYZNB-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 56
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 13
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
206010039966 Senile dementia Diseases 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
150000007524 organic acids Chemical class 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 8
150000007522 mineralic acids Chemical class 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
208000026139 Memory disease Diseases 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
-1 possibly substituted Chemical group 0.000 abstract description 23
125000003118 aryl group Chemical group 0.000 abstract description 3
150000007513 acids Chemical class 0.000 abstract description 2
229910052500 inorganic mineral Inorganic materials 0.000 abstract description 2
239000011707 mineral Substances 0.000 abstract description 2
125000003342 alkenyl group Chemical group 0.000 abstract 2
125000000304 alkynyl group Chemical group 0.000 abstract 2
230000007547 defect Effects 0.000 abstract 1
229910052739 hydrogen Inorganic materials 0.000 abstract 1
239000001257 hydrogen Substances 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 20
238000004458 analytical method Methods 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000003480 eluent Substances 0.000 description 10
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
150000002923 oximes Chemical class 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 6
230000036760 body temperature Effects 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000002904 solvent Substances 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
230000001713 cholinergic effect Effects 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
YIQBHPFHKPIDSO-UHFFFAOYSA-N n-methoxy-1-(1,2,3,6-tetrahydropyridin-5-yl)methanimine Chemical compound CON=CC1=CCCNC1 YIQBHPFHKPIDSO-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 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
238000004821 distillation Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
210000003608 fece Anatomy 0.000 description 3
210000003405 ileum Anatomy 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
238000005303 weighing Methods 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
MAIZIPFKUVNTLJ-UHFFFAOYSA-N CCOC(=O)N1CCC=C(C=NO)C1 Chemical compound CCOC(=O)N1CCC=C(C=NO)C1 MAIZIPFKUVNTLJ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
229960004373 acetylcholine Drugs 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
238000009736 wetting Methods 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
RYWGPCLTVXMMHO-UHFFFAOYSA-N (4-chlorophenyl) carbonochloridate Chemical compound ClC(=O)OC1=CC=C(Cl)C=C1 RYWGPCLTVXMMHO-UHFFFAOYSA-N 0.000 description 1
MMWNTLCGGPKVFR-UHFFFAOYSA-N 1-(1-ethyl-3,6-dihydro-2h-pyridin-5-yl)-n-methoxymethanimine Chemical compound CCN1CCC=C(C=NOC)C1 MMWNTLCGGPKVFR-UHFFFAOYSA-N 0.000 description 1
PNLZKVOKOVFGMZ-UHFFFAOYSA-N 1-adamantyl carbonofluoridate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)F)C3 PNLZKVOKOVFGMZ-UHFFFAOYSA-N 0.000 description 1
DKULSTMKCYRQCP-UHFFFAOYSA-N 2-phenylethyl carbonochloridate Chemical compound ClC(=O)OCCC1=CC=CC=C1 DKULSTMKCYRQCP-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
229930003347 Atropine Natural products 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OGSQGNOQMVABGK-UHFFFAOYSA-N CC(C)(C)OC(=O)N1CCC=C(C=NO)C1 Chemical compound CC(C)(C)OC(=O)N1CCC=C(C=NO)C1 OGSQGNOQMVABGK-UHFFFAOYSA-N 0.000 description 1
YXBXEGFRALZBRC-UHFFFAOYSA-N CC(C)OC(=O)N1CCC=C(C=NO)C1 Chemical compound CC(C)OC(=O)N1CCC=C(C=NO)C1 YXBXEGFRALZBRC-UHFFFAOYSA-N 0.000 description 1
XJYYMEILNYJYOP-UHFFFAOYSA-N CCCOC(=O)N1CCC=C(C=NO)C1 Chemical compound CCCOC(=O)N1CCC=C(C=NO)C1 XJYYMEILNYJYOP-UHFFFAOYSA-N 0.000 description 1
DRDPHSQWCSQEKS-UHFFFAOYSA-N COC=1C=C(C=CC1OC)OC(=O)N1CC(=CCC1)C=NO Chemical compound COC=1C=C(C=CC1OC)OC(=O)N1CC(=CCC1)C=NO DRDPHSQWCSQEKS-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-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
235000011054 acetic acid Nutrition 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
239000000556 agonist Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
KVILUFYYUJUTDJ-UHFFFAOYSA-N benzene;n,n-diethylethanamine Chemical compound C1=CC=CC=C1.CCN(CC)CC KVILUFYYUJUTDJ-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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 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
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
230000008602 contraction Effects 0.000 description 1
230000001595 contractor effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000006165 cyclic alkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003995 emulsifying agent Substances 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
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
230000001200 fecal consistency Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
244000144993 groups of animals Species 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
230000002475 laxative effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
230000003551 muscarinic effect Effects 0.000 description 1
IRGVZKFUJKODCN-UHFFFAOYSA-N n-prop-2-ynoxy-1-(1,2,3,6-tetrahydropyridin-5-yl)methanimine Chemical compound C#CCON=CC1=CCCNC1 IRGVZKFUJKODCN-UHFFFAOYSA-N 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000004044 response Effects 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical 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)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)

JP63203962A 1987-08-21 1988-08-18 新規の１，２，５，６−テトラヒドロピリジン−３−カルボキサアルデヒドロのオキシムの誘導体、それらの製造方法、それらの薬剤としての使用及びそれらを含有する組成物 Expired - Fee Related JPH07107048B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT21687-A/87		1987-08-21
IT8721687A IT1222526B (it)	1987-08-21	1987-08-21	Derivati dell' ossima della 1,2,5,6-tetraidropiridin-3-carbossaldeide,loro procedimento di preparazione e loro impiego come sostanze medicinali

Publications (2)

Publication Number	Publication Date
JPS6468356A JPS6468356A (en)	1989-03-14
JPH07107048B2 true JPH07107048B2 (ja)	1995-11-15

Family

ID=11185397

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63203962A Expired - Fee Related JPH07107048B2 (ja)	1987-08-21	1988-08-18	新規の１，２，５，６−テトラヒドロピリジン−３−カルボキサアルデヒドロのオキシムの誘導体、それらの製造方法、それらの薬剤としての使用及びそれらを含有する組成物

Country Status (22)

Country	Link
US (1)	US4921868A (2)
EP (1)	EP0308283B1 (2)
JP (1)	JPH07107048B2 (2)
KR (1)	KR960014998B1 (2)
AT (1)	ATE71938T1 (2)
AU (1)	AU608643B2 (2)
CA (1)	CA1340987C (2)
DE (1)	DE3867986D1 (2)
DK (1)	DK457388A (2)
ES (1)	ES2038776T3 (2)
FI (1)	FI90070C (2)
GR (1)	GR3004249T3 (2)
HU (2)	HU201012B (2)
IE (1)	IE61537B1 (2)
IL (1)	IL87430A0 (2)
IT (1)	IT1222526B (2)
MX (1)	MX12707A (2)
NO (1)	NO174504B (2)
NZ (1)	NZ225902A (2)
PT (1)	PT88302B (2)
SU (1)	SU1681723A3 (2)
ZA (1)	ZA886131B (2)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5231107A (en) *	1987-08-21	1993-07-27	Roussel Uclaf	Derivatives of the oxime of 1,2,5,6-tetrahydropyridine 3-carboxaldehyde, the process for their preparation, their use as medicaments and the compositions containing them
PT90266B (pt) *	1988-04-15	1994-07-29	Beecham Group Plc	Processo para a preparacao de compostos azabiciclicos
SG48315A1 (en) *	1989-04-13	1998-04-17	Beecham Group Plc	Novel compounds
US5278170A (en) *	1989-04-13	1994-01-11	Beecham Group P.L.C.	Azabicylo oxime compounds
IT1240603B (it) *	1990-03-14	1993-12-17	Roussel Maestretti Spa	Derivati della 1,2,5,6-tetraidropiridina 3- carbossaldeide ossima, loro procedimento di preparazione e loro impiego come sostanza medicinale
IT1241138B (it) *	1990-05-15	1993-12-29	Roussel Pharma	Derivati dell'ossina della 1,2,5,6- tetraidropiridin-3-carbossaldeide,loro procedimento di preparazione e loro impiego come sostanze medicinali
WO1992003435A1 (en) *	1990-08-24	1992-03-05	Beecham Group Plc	Azabicyclic compounds, process and intermediates for their preparation and pharmaceutical compositions containing them
GB9019095D0 (en) *	1990-09-01	1990-10-17	Beecham Group Plc	Novel compounds
CA2093823A1 (en) *	1990-10-12	1992-04-13	Steven M. Bromidge	1,2,5,6-tetrahydropyridine oxime derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1258847A (fr) *	1960-02-12	1961-04-21	Ciba Geigy	Procédé de préparation de nouveaux dérivés pyridiniques, entre autres de l'oxime de la l-méthyl-3 ou 4-acétyl-1, 2, 5, 6-tétrahydropyridine
IL81610A (en) *	1986-02-27	1990-12-23	Roussel Uclaf	Derivatives of 1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime,their preparation and pharmaceutical compositions containing them
US4786648A (en) *	1986-12-08	1988-11-22	Warner-Lambert Company	O-substituted tetrahydropyridine oxime cholinergic agents
IT1203971B (it) *	1987-04-24	1989-02-23	Roussel Maestretti Spa	Derivati di 1,2,5,6-tetraidropiridina, loro procedimento di preparazione e loro applicazione come medicamenti

1987
- 1987-08-21 IT IT8721687A patent/IT1222526B/it active
1988
- 1988-08-08 NO NO883521A patent/NO174504B/no unknown
- 1988-08-12 IL IL8887430A patent/IL87430A0/xx not_active IP Right Cessation
- 1988-08-16 DK DK457388A patent/DK457388A/da not_active Application Discontinuation
- 1988-08-17 MX MX1270788A patent/MX12707A/es unknown
- 1988-08-18 JP JP63203962A patent/JPH07107048B2/ja not_active Expired - Fee Related
- 1988-08-18 ZA ZA886131A patent/ZA886131B/xx unknown
- 1988-08-19 AU AU21100/88A patent/AU608643B2/en not_active Ceased
- 1988-08-19 FI FI883869A patent/FI90070C/fi not_active IP Right Cessation
- 1988-08-19 SU SU4356622A patent/SU1681723A3/ru active
- 1988-08-19 HU HU884414A patent/HU201012B/hu not_active IP Right Cessation
- 1988-08-19 EP EP88402128A patent/EP0308283B1/fr not_active Expired - Lifetime
- 1988-08-19 IE IE253888A patent/IE61537B1/en not_active IP Right Cessation
- 1988-08-19 AT AT88402128T patent/ATE71938T1/de not_active IP Right Cessation
- 1988-08-19 CA CA000575166A patent/CA1340987C/fr not_active Expired - Fee Related
- 1988-08-19 PT PT88302A patent/PT88302B/pt not_active IP Right Cessation
- 1988-08-19 ES ES198888402128T patent/ES2038776T3/es not_active Expired - Lifetime
- 1988-08-19 DE DE8888402128T patent/DE3867986D1/de not_active Expired - Fee Related
- 1988-08-22 US US07/234,632 patent/US4921868A/en not_active Expired - Fee Related
- 1988-08-22 KR KR1019880010676A patent/KR960014998B1/ko not_active Expired - Fee Related
- 1988-08-22 NZ NZ225902A patent/NZ225902A/xx unknown
1992
- 1992-04-02 GR GR910402203T patent/GR3004249T3/el unknown
1995
- 1995-06-29 HU HU95P/P00578P patent/HU211913A9/hu unknown

Also Published As

Publication number	Publication date
PT88302B (pt)	1995-03-31
DK457388D0 (da)	1988-08-16
IT8721687A0 (it)	1987-08-21
IE61537B1 (en)	1994-11-16
KR960014998B1 (ko)	1996-10-23
EP0308283A1 (fr)	1989-03-22
NO883521L (no)	1989-02-22
FI90070B (fi)	1993-09-15
AU608643B2 (en)	1991-04-11
JPS6468356A (en)	1989-03-14
KR890003692A (ko)	1989-04-17
FI90070C (fi)	1993-12-27
GR3004249T3 (2)	1993-03-31
CA1340987C (fr)	2000-05-09
MX12707A (es)	1993-10-01
ATE71938T1 (de)	1992-02-15
NO174504B (no)	1994-02-07
NO174504C (2)	1994-05-18
HU201012B (en)	1990-09-28
IL87430A0 (en)	1989-01-31
HU211913A9 (en)	1996-01-29
NZ225902A (en)	1990-06-26
DK457388A (da)	1989-02-22
PT88302A (pt)	1989-09-14
HUT49328A (en)	1989-09-28
IE882538L (en)	1989-02-21
NO883521D0 (no)	1988-08-08
EP0308283B1 (fr)	1992-01-22
IT1222526B (it)	1990-09-05
FI883869A7 (fi)	1989-02-22
FI883869A0 (fi)	1988-08-19
DE3867986D1 (de)	1992-03-05
US4921868A (en)	1990-05-01
AU2110088A (en)	1989-02-23
ZA886131B (en)	1989-10-25
ES2038776T3 (es)	1993-08-01
SU1681723A3 (ru)	1991-09-30

Legal Events

Date	Code	Title	Description
2003-11-15	LAPS	Cancellation because of no payment of annual fees

Publication	Publication Date	Title
US5219872A (en)	1993-06-15	Compounds of 1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime which are useful as cholinergic agents
EP1499589B1 (fr)	2007-05-02	Derives de n-¬phenyl(piperidin-2-yl)methyl\|benzamide, leur preparation et leur application en therapeutique
JP2727192B2 (ja)	1998-03-11	新規の１，２，５，６−テトラヒドロピリジン誘導体、それらの製造方法、それらの薬剤としての使用及びそれらを含有する組成物
JP2660430B2 (ja)	1997-10-08	新規の１，２，５，６−テトラヒドロピリジン−３−カルボキサアルデヒドのオキシム誘導体、それらの製造方法、それらの薬剤としての使用及びそれらを含有する組成物
US5053416A (en)	1991-10-01	Derivatives of 1,2,5,6-tetrahydropyridine substituted by a thiazolyl or oxazolyl radical, their use as medicaments and compositions containing them
KR960014998B1 (ko)	1996-10-23	1,2,5,6-테트라히드로피리딘-3-카르복스알데히드의 옥심유도체, 이들의 제조방법, 약제로서의 이들의 용도 및 이들을 함유하는 조성물
EP0366561A2 (fr)	1990-05-02	Nouveaux dérivés 1-azabicycloalkanes, leur procédé de préparation et leur application comme médicaments
US4927837A (en)	1990-05-22	Derivatives of 3-piperidine carbaldehyde oxime and their use as medicaments
US5219873A (en)	1993-06-15	Compounds of 1,2,5,6-tetrahydropyridine which are useful as cholinergic agents
JPH0346467B2 (2)	1991-07-16
US5231107A (en)	1993-07-27	Derivatives of the oxime of 1,2,5,6-tetrahydropyridine 3-carboxaldehyde, the process for their preparation, their use as medicaments and the compositions containing them
US5183893A (en)	1993-02-02	1-azabicycloalkane derivatives, their preparation process and their use as medicaments
US5183896A (en)	1993-02-02	Derivatives of 1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime
JPH0143758B2 (2)	1989-09-22