JPH06505706A - 新規な１−アザビシクロアルカン誘導体、それを含む製剤組成物及びその製法 - Google Patents

新規な１−アザビシクロアルカン誘導体、それを含む製剤組成物及びその製法

Info

Publication number: JPH06505706A
Authority: JP; Japan
Prior art keywords: endo; general formula; acid; ene; mmol
Prior art date: 1990-11-05
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.): Pending

Application number

JP4500523A

Other languages

English (en)

Japanese (ja)

Inventor

ソーリョム，サーンドル

アブラハム，ギゼラ

ソェロェシュイ，マーリタ

ボルシ，ヨージェフ

ヴィターリシュ，ベアータ

カリムネー　タプフェル，マリアン

サボーネー　バディ，エルジェーベト

ツッズィ，エメシェ

ゴルヂュッツミドトゥネー　ホルヴァートゥ，カタリン

マーテ，ヂョェルヂネー

リング，イシュトゥヴァーン

ミクローシュネー　コヴァーチュ，アニコー

Original Assignee

ヂョーヂセルクタトー　インテーゼト　カーエフテー

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.)

1990-11-05

Filing date

1991-11-05

Publication date

1994-06-30

1991-11-05 Application filed by ヂョーヂセルクタトー　インテーゼト　カーエフテー filed Critical ヂョーヂセルクタトー　インテーゼト　カーエフテー

1994-06-30 Publication of JPH06505706A publication Critical patent/JPH06505706A/ja

Status Pending legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 6
239000008194 pharmaceutical composition Substances 0.000 title claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 111
150000001875 compounds Chemical class 0.000 claims description 52
238000000034 method Methods 0.000 claims description 38
239000002253 acid Substances 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 35
YCBSHDKATAPNIA-UHFFFAOYSA-N non-3-ene Chemical compound CCCCCC=CCC YCBSHDKATAPNIA-UHFFFAOYSA-N 0.000 claims description 34
-1 methoxy, methylthio Chemical group 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000001624 naphthyl group Chemical group 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 4
238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
AKCVBCRPNQCGNB-UHFFFAOYSA-N 1-hydroxy-2h-pyridine-2,3,6-triol Chemical class OC1N(O)C(O)=CC=C1O AKCVBCRPNQCGNB-UHFFFAOYSA-N 0.000 claims 1
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
239000000047 product Substances 0.000 description 77
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
239000000203 mixture Substances 0.000 description 66
238000002844 melting Methods 0.000 description 64
230000008018 melting Effects 0.000 description 64
239000011541 reaction mixture Substances 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 33
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 28
239000002585 base Substances 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
239000012044 organic layer Substances 0.000 description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
238000001953 recrystallisation Methods 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
239000012043 crude product Substances 0.000 description 14
229910000029 sodium carbonate Inorganic materials 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
239000013078 crystal Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
238000001704 evaporation Methods 0.000 description 9
239000007858 starting material Substances 0.000 description 9
238000012360 testing method Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
GGZQLTVZPOGLCC-UHFFFAOYSA-N 2-(2-bromoethyl)-1,3-dioxolane Chemical compound BrCCC1OCCO1 GGZQLTVZPOGLCC-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000012452 mother liquor Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
238000011282 treatment Methods 0.000 description 6
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
239000003480 eluent Substances 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
229910052749 magnesium Inorganic materials 0.000 description 4
239000000463 material Substances 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
YCTDZYMMFQCTEO-FNORWQNLSA-N (E)-3-octene Chemical compound CCCC\C=C\CC YCTDZYMMFQCTEO-FNORWQNLSA-N 0.000 description 3
208000000044 Amnesia Diseases 0.000 description 3
208000031091 Amnestic disease Diseases 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
230000006986 amnesia Effects 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
238000010828 elution Methods 0.000 description 3
239000002024 ethyl acetate extract Substances 0.000 description 3
239000012467 final product Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
IATJWQHWZUYXGC-UHFFFAOYSA-N nonane;hydrochloride Chemical compound Cl.CCCCCCCCC IATJWQHWZUYXGC-UHFFFAOYSA-N 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 2
QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 2
208000024827 Alzheimer disease Diseases 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 2
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229910052776 Thorium Inorganic materials 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
229960004217 benzyl alcohol Drugs 0.000 description 2
239000002775 capsule Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
230000001713 cholinergic effect Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
210000003127 knee Anatomy 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
230000003551 muscarinic effect Effects 0.000 description 2
YMYAGTRATSSHHT-UHFFFAOYSA-N oct-3-ene;hydrochloride Chemical compound Cl.CCCCC=CCC YMYAGTRATSSHHT-UHFFFAOYSA-N 0.000 description 2
239000006186 oral dosage form Substances 0.000 description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000004033 plastic Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
238000012549 training Methods 0.000 description 2
238000005303 weighing Methods 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IRRBLYIEYFCACE-UHFFFAOYSA-N 1-[2-(1,3-dioxolan-2-yl)ethyl]-4-(4-fluorophenyl)piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC(F)=CC=2)CCN1CCC1OCCO1 IRRBLYIEYFCACE-UHFFFAOYSA-N 0.000 description 1
WOICZUZBFJVANR-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-2-yl benzoate Chemical compound C1C(CC2)CCN2C1OC(=O)C1=CC=CC=C1 WOICZUZBFJVANR-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
WMDHQEHPOVOEOG-UHFFFAOYSA-N 2-(2-bromoethyl)-1,3-dioxane Chemical compound BrCCC1OCCCO1 WMDHQEHPOVOEOG-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
JLBJYGCSAOHRPK-UHFFFAOYSA-N 4-(4-chloroanilino)-2,3-dihydroxy-4-oxobutanoic acid Chemical compound OC(=O)C(O)C(O)C(=O)NC1=CC=C(Cl)C=C1 JLBJYGCSAOHRPK-UHFFFAOYSA-N 0.000 description 1
LZAYOZUFUAMFLD-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-hydroxypiperidine Chemical compound C=1C=C(Cl)C=CC=1C1(O)CCNCC1 LZAYOZUFUAMFLD-UHFFFAOYSA-N 0.000 description 1
UIDHWZHWPNGJFS-UHFFFAOYSA-N 4-(4-methylsulfanylphenyl)piperidin-4-ol;hydrochloride Chemical compound Cl.C1=CC(SC)=CC=C1C1(O)CCNCC1 UIDHWZHWPNGJFS-UHFFFAOYSA-N 0.000 description 1
UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 description 1
TXKPOHRJWZOUNR-UHFFFAOYSA-N 6-methyl-4-phenyl-1-azabicyclo[3.3.1]nona-3,6-diene Chemical compound C1C2C(C)=CCN1CC=C2C1=CC=CC=C1 TXKPOHRJWZOUNR-UHFFFAOYSA-N 0.000 description 1
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 1
229930000680 A04AD01 - Scopolamine Natural products 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229930003347 Atropine Natural products 0.000 description 1
101150071434 BAR1 gene Proteins 0.000 description 1
241001658044 Beata Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
244000304337 Cuminum cyminum Species 0.000 description 1
235000007129 Cuminum cyminum Nutrition 0.000 description 1
206010012289 Dementia Diseases 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
241000790917 Dioxys <bee> Species 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 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
BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
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 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 1
238000011672 OFA rat Methods 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000053208 Porcellio laevis Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
206010040047 Sepsis Diseases 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
235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
244000250129 Trigonella foenum graecum Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
CDXSJGDDABYYJV-UHFFFAOYSA-N acetic acid;ethanol Chemical compound CCO.CC(O)=O CDXSJGDDABYYJV-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
NMPVEAUIHMEAQP-UHFFFAOYSA-N alpha-bromo-acetaldehyde Natural products BrCC=O NMPVEAUIHMEAQP-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000003496 anti-amnesic effect Effects 0.000 description 1
239000003420 antiserotonin agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
229960000396 atropine Drugs 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
CEVDPSDZXGCLEI-UHFFFAOYSA-N bicyclo[3.3.1]non-3-ene Chemical compound C1C=CC2CCCC1C2 CEVDPSDZXGCLEI-UHFFFAOYSA-N 0.000 description 1
230000027455 binding Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
244000309464 bull Species 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
239000001768 carboxy methyl cellulose Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000029087 digestion Effects 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
SXAZIVDIJFIFIH-UHFFFAOYSA-N ethyl 4-hydroxy-4-(2-methoxyphenyl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(O)C1=CC=CC=C1OC SXAZIVDIJFIFIH-UHFFFAOYSA-N 0.000 description 1
DQFLBZNBUVFLCE-UHFFFAOYSA-N ethyl 4-hydroxy-4-(4-methoxyphenyl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(O)C1=CC=C(OC)C=C1 DQFLBZNBUVFLCE-UHFFFAOYSA-N 0.000 description 1
LUBGFMZTGFXIIN-UHFFFAOYSA-N ethyl 4-oxopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(=O)CC1 LUBGFMZTGFXIIN-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
SAVROPQJUYSBDD-UHFFFAOYSA-N formyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CO SAVROPQJUYSBDD-UHFFFAOYSA-N 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
230000006870 function Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000003446 ligand Substances 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
239000006166 lysate Substances 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
229960005337 lysine hydrochloride Drugs 0.000 description 1
235000005398 marita Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003149 muscarinic antagonist Substances 0.000 description 1
GXSKKEQDZDDIQS-UHFFFAOYSA-N n,n-diethylethanamine;phenylmethanol Chemical compound CCN(CC)CC.OCC1=CC=CC=C1 GXSKKEQDZDDIQS-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000004526 pharmaceutical effect Effects 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical class OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000003672 processing method Methods 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000011514 reflex Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000013391 scatchard analysis Methods 0.000 description 1
STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
229960002646 scopolamine Drugs 0.000 description 1
230000036299 sexual function Effects 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000010972 statistical evaluation Methods 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP4500523A 1990-11-05 1991-11-05 新規な１−アザビシクロアルカン誘導体、それを含む製剤組成物及びその製法 Pending JPH06505706A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
HU907014A HU209451B (en)	1990-11-05	1990-11-05	Process for the production of 1-azabicyclo-alkan -derivatives and pharmaceutical preparations containing the same
HU7014/90		1990-11-05
PCT/HU1991/000048 WO1992007854A1 (en)	1990-11-05	1991-11-05	New 1-azabicycloalkane derivatives, pharmaceutical compositions containing them and process for preparing same

Publications (1)

Publication Number	Publication Date
JPH06505706A true JPH06505706A (ja)	1994-06-30

Family

ID=10972102

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4500523A Pending JPH06505706A (ja)	1990-11-05	1991-11-05	新規な１−アザビシクロアルカン誘導体、それを含む製剤組成物及びその製法

Country Status (9)

Country	Link
EP (1)	EP0556342A1 (cs)
JP (1)	JPH06505706A (cs)
KR (1)	KR930702290A (cs)
AU (1)	AU645377B2 (cs)
CA (1)	CA2093417A1 (cs)
CZ (1)	CZ75293A3 (cs)
FI (1)	FI932034A0 (cs)
HU (1)	HU209451B (cs)
WO (1)	WO1992007854A1 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6150376A (en) *	1998-08-05	2000-11-21	Georgetown University	Bi- and tri-cyclic aza compounds and their uses
US6875774B2 (en) *	2002-08-06	2005-04-05	The University Of North Carolina	Aza-bridged bicyclic amine derivatives for use as novel cholinergic receptor ligands

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8520616D0 (en) *	1985-08-16	1985-09-25	Beecham Group Plc	Compounds
GB8615785D0 (en) *	1986-06-27	1986-08-06	Beecham Group Plc	Compounds
NZ227841A (en) *	1988-02-12	1991-08-27	Merck Sharp & Dohme	Heterocyclic compounds with at least two non-condensed five membered rings and pharmaceutical compositions

1990
- 1990-11-05 HU HU907014A patent/HU209451B/hu not_active IP Right Cessation
1991
- 1991-11-05 EP EP92902582A patent/EP0556342A1/en not_active Withdrawn
- 1991-11-05 JP JP4500523A patent/JPH06505706A/ja active Pending
- 1991-11-05 CZ CS93752A patent/CZ75293A3/cs unknown
- 1991-11-05 KR KR1019930701327A patent/KR930702290A/ko not_active Withdrawn
- 1991-11-05 AU AU89113/91A patent/AU645377B2/en not_active Ceased
- 1991-11-05 CA CA002093417A patent/CA2093417A1/en not_active Abandoned
- 1991-11-05 WO PCT/HU1991/000048 patent/WO1992007854A1/en not_active Ceased
1993
- 1993-05-05 FI FI932034A patent/FI932034A0/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
HU209451B (en)	1994-06-28
CA2093417A1 (en)	1992-05-06
FI932034A7 (fi)	1993-05-05
HU907014D0 (en)	1991-05-28
WO1992007854A1 (en)	1992-05-14
AU8911391A (en)	1992-05-26
HUT59922A (en)	1992-07-28
EP0556342A1 (en)	1993-08-25
AU645377B2 (en)	1994-01-13
KR930702290A (ko)	1993-09-08
CZ75293A3 (en)	1994-02-16
FI932034A0 (fi)	1993-05-05

Publication	Publication Date	Title
JP2535134B2 (ja)	1996-09-18	縮合三環式窒素含有複素環
AU720358B2 (en)	2000-06-01	Tropane-derivatives, their preparation and use
EP0585328B1 (en)	2002-01-09	Substituted 3-aminoquinuclidines
DE69034146T2 (de)	2005-07-14	Chemische Verbindungen
AU2016217461B2 (en)	2018-07-05	Amide compounds as 5-HT4 receptor agonists
JPH0578354A (ja)	1993-03-30	アザ二環式化合物、これを含有する医薬組成物及び治療のための使用方法
CA2071800A1 (en)	1992-12-25	Azabicyclic compounds, pharmaceutical compositions containing them and their use in therapy
HRP20000495A2 (en)	2003-06-30	N-acyl cyclic amine derivatives
US6677338B2 (en)	2004-01-13	Serotonin transport inhibitors
CA2354606C (en)	2005-12-06	Azabicycloalkane derivatives and therapeutic uses thereof
US5179109A (en)	1993-01-12	Pharmaceutical compositions for neuroprotection containing arylcyclohexylamines
US5468875A (en)	1995-11-21	1-azabicycloheptane derivatives
US5716965A (en)	1998-02-10	Substituted 3-aminoquinuclidines
JPH06505706A (ja)	1994-06-30	新規な１−アザビシクロアルカン誘導体、それを含む製剤組成物及びその製法
WO2021132311A1 (ja)	2021-07-01	脂肪族酸アミド誘導体
JPH07503462A (ja)	1995-04-13	カルシウムチャンネル拮抗薬としてのアザビシクロ化合物
US5668144A (en)	1997-09-16	1-azabicyclopheptane derivatives
KR20150129698A (ko)	2015-11-20	피롤리딘-3-일 아세트산 유도체의 염 및 그의 결정
JPH02215782A (ja)	1990-08-28	新規化合物、その製法及びそれを含む医薬組成物
JP2719063B2 (ja)	1998-02-25	置換３−アミノキヌクリジンｐ物質拮抗剤
HK1263040A1 (en)	2020-01-24	Crystalline forms and processes for the preparation of condensed azacycles (cannabinoid receptor modulators)