DD300105A5 - Neue R(-)3-Quinuliclidinol - Derivate - Google Patents

Neue R(-)3-Quinuliclidinol - Derivate Download PDF

Info

Publication number: DD300105A5
Authority: DD; German Democratic Republic
Prior art keywords: phenyl; oxo; carboxylate; octyl; compounds
Prior art date: 1989-06-20

Application number

DD341777A

Other languages

German (de)

English (en)

Original Assignee

Angeli Inst Spa

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.)

1989-06-20

Filing date

1990-06-18

Publication date

1992-05-21

1990-06-18 Application filed by Angeli Inst Spa filed Critical Angeli Inst Spa

1992-05-21 Publication of DD300105A5 publication Critical patent/DD300105A5/de

Links

150000001875 compounds Chemical class 0.000 claims abstract description 79
238000000034 method Methods 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
-1 3-quinuclidinyl Chemical group 0.000 claims abstract description 13
238000002360 preparation method Methods 0.000 claims abstract description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
208000035475 disorder Diseases 0.000 claims abstract description 11
238000011282 treatment Methods 0.000 claims abstract description 11
239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
239000001301 oxygen Substances 0.000 claims abstract description 8
230000008569 process Effects 0.000 claims abstract description 7
210000002345 respiratory system Anatomy 0.000 claims abstract description 7
229910052799 carbon Inorganic materials 0.000 claims abstract description 6
150000007522 mineralic acids Chemical class 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 5
150000007524 organic acids Chemical class 0.000 claims abstract description 5
238000006467 substitution reaction Methods 0.000 claims abstract description 5
239000011593 sulfur Substances 0.000 claims abstract description 5
206010006482 Bronchospasm Diseases 0.000 claims abstract description 4
125000002252 acyl group Chemical group 0.000 claims abstract description 4
150000001450 anions Chemical class 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 4
230000007885 bronchoconstriction Effects 0.000 claims abstract description 4
125000004185 ester group Chemical group 0.000 claims abstract description 4
206010006458 Bronchitis chronic Diseases 0.000 claims abstract description 3
206010014561 Emphysema Diseases 0.000 claims abstract description 3
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
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206010006451 bronchitis Diseases 0.000 claims abstract description 3
208000007451 chronic bronchitis Diseases 0.000 claims abstract description 3
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 21
239000004480 active ingredient Substances 0.000 claims description 17
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 9
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
IVLICPVPXWEGCA-ZETCQYMHSA-N (3r)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1CC2[C@@H](O)CN1CC2 IVLICPVPXWEGCA-ZETCQYMHSA-N 0.000 claims description 8
229940102396 methyl bromide Drugs 0.000 claims description 6
230000001148 spastic effect Effects 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
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239000012442 inert solvent Substances 0.000 claims description 3
230000000414 obstructive effect Effects 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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LIUAALCHBQSCCX-SSDOTTSWSA-N (2r)-1-azoniabicyclo[2.2.2]octane-2-carboxylate Chemical compound C1CN2[C@@H](C(=O)O)CC1CC2 LIUAALCHBQSCCX-SSDOTTSWSA-N 0.000 claims description 2
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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 claims description 2
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AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 claims description 2
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AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
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235000002906 tartaric acid Nutrition 0.000 claims description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 1
206010007645 Cardiospasm Diseases 0.000 claims 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
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239000004606 Fillers/Extenders Substances 0.000 claims 1
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239000011734 sodium Substances 0.000 description 16
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
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239000012044 organic layer Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
230000003551 muscarinic effect Effects 0.000 description 6
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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 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
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VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
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125000003545 alkoxy group Chemical group 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
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QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
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 3
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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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
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Pulmonology (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyrrole Compounds (AREA)

DD341777A 1989-06-20 1990-06-18 Neue R(-)3-Quinuliclidinol - Derivate DD300105A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT8920929A IT1230881B (it)	1989-06-20	1989-06-20	Derivati del r(-) 3-chinuclidinolo

Publications (1)

Publication Number	Publication Date
DD300105A5 true DD300105A5 (de)	1992-05-21

Family

ID=11174223

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD341777A DD300105A5 (de)	1989-06-20	1990-06-18	Neue R(-)3-Quinuliclidinol - Derivate

Country Status (19)

Country	Link
US (1)	US5164386A (no)
EP (1)	EP0404737A3 (no)
JP (1)	JPH0331279A (no)
KR (1)	KR910000720A (no)
AU (1)	AU634787B2 (no)
CA (1)	CA2019251A1 (no)
DD (1)	DD300105A5 (no)
FI (1)	FI94131C (no)
HU (1)	HUT54151A (no)
IE (1)	IE902208A1 (no)
IL (1)	IL94763A (no)
IT (1)	IT1230881B (no)
NO (1)	NO174053C (no)
NZ (1)	NZ234157A (no)
PL (1)	PL164218B1 (no)
PT (1)	PT94408A (no)
RU (1)	RU2034843C1 (no)
YU (1)	YU47356B (no)
ZA (1)	ZA904736B (no)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9106571D0 (en) *	1991-03-27	1991-05-15	Erba Carlo Spa	Derivatives of substituted imidazol-2-one and process for their preparation
AU7618991A (en) *	1990-05-14	1991-11-14	Syntex (U.S.A.) Inc.	Novel tricyclic compounds
US5202318A (en) *	1990-05-14	1993-04-13	Syntex (U.S.A.) Inc.	Tricyclic compounds acting at serotonin receptor subtypes
HUT65612A (en) *	1991-01-10	1994-07-28	Pfizer	Process n-alcyl-quinuclidinium salts of p-antagonistic activity
US5340826A (en) *	1993-02-04	1994-08-23	Pfizer Inc.	Pharmaceutical agents for treatment of urinary incontinence
US7214686B2 (en) *	1997-06-30	2007-05-08	Targacept, Inc.	Pharmaceutical compositions and methods for effecting dopamine release
EE05404B1 (et)	2000-12-28	2011-04-15	Almirall Prodesfarma Ag	Kinuklidiini derivaat, selle saamine ja kasutamine ravimi valmistamiseks, mis on ette nhtud respiratoorsete, kuseelundite v?i mao-soolte haiguste ravimiseks, ning seda sisaldav ravimkompositsioon
WO2014105655A1 (en)	2012-12-24	2014-07-03	Neurogastrx, Inc.	Methods for treating gi tract disorders
WO2015200369A1 (en)	2014-06-24	2015-12-30	Neurogastrx, Inc.	Prodrugs of metopimazine
KR102423577B1 (ko)	2017-04-07	2022-07-21	삼성전자주식회사	가전기기
US10836757B1 (en)	2020-04-02	2020-11-17	Neurogastrx, Inc.	Polymorphic forms of metopimazine

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3290316A (en) *	1962-08-03	1966-12-06	Hoffmann La Roche	Alpha-3-pyridylmandelic acid and derivatives thereof
CH664567A5 (de) *	1983-08-26	1988-03-15	Sandoz Ag	Aromatische carbonsaeure- und sulfonsaeureester oder -amide.
CA1307790C (en) *	1987-08-04	1992-09-22	Ian Anthony Cliffe	Ethers
ZA886585B (en) *	1987-09-08	1990-05-30	Lilly Co Eli	Specific 5-ht,antagonists
US4921982A (en) *	1988-07-21	1990-05-01	Eli Lilly And Company	5-halo-2,3-dihydro-2,2-dimethylbenzofuran-7-carboxylic acids useful as intermediates for 5-HT3 antagonists
IT1231413B (it) *	1987-09-23	1991-12-04	Angeli Inst Spa	Derivati dell'acido benzimidazolin-2-osso-1-carbossilico utili come antagonisti dei recettori 5-ht
US4975437A (en) *	1989-12-14	1990-12-04	Marion Laboratories, Inc.	Isomers of 1-azabicyclo(2.2.2)oct-3-yl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-nitropyridine-3-carboxylate

1989
- 1989-06-20 IT IT8920929A patent/IT1230881B/it active
1990
- 1990-06-18 PL PL90285669A patent/PL164218B1/pl unknown
- 1990-06-18 IL IL9476390A patent/IL94763A/en not_active IP Right Cessation
- 1990-06-18 DD DD341777A patent/DD300105A5/de unknown
- 1990-06-19 EP EP19900830281 patent/EP0404737A3/en not_active Withdrawn
- 1990-06-19 HU HU903908A patent/HUT54151A/hu unknown
- 1990-06-19 NO NO902710A patent/NO174053C/no unknown
- 1990-06-19 IE IE220890A patent/IE902208A1/en unknown
- 1990-06-19 YU YU120290A patent/YU47356B/sh unknown
- 1990-06-19 JP JP2161192A patent/JPH0331279A/ja active Pending
- 1990-06-19 KR KR1019900008991A patent/KR910000720A/ko not_active Application Discontinuation
- 1990-06-19 PT PT94408A patent/PT94408A/pt not_active Application Discontinuation
- 1990-06-19 ZA ZA904736A patent/ZA904736B/xx unknown
- 1990-06-19 FI FI903077A patent/FI94131C/fi not_active IP Right Cessation
- 1990-06-19 CA CA002019251A patent/CA2019251A1/en not_active Abandoned
- 1990-06-20 NZ NZ234157A patent/NZ234157A/xx unknown
- 1990-06-20 AU AU57649/90A patent/AU634787B2/en not_active Ceased
- 1990-06-20 US US07/541,106 patent/US5164386A/en not_active Expired - Fee Related
1992
- 1992-03-10 RU SU925011061A patent/RU2034843C1/ru active

Also Published As

Publication number	Publication date
FI94131C (fi)	1995-07-25
US5164386A (en)	1992-11-17
EP0404737A2 (en)	1990-12-27
FI94131B (fi)	1995-04-13
PT94408A (pt)	1991-02-08
YU47356B (sh)	1995-01-31
FI903077A0 (fi)	1990-06-19
IT1230881B (it)	1991-11-08
RU2034843C1 (ru)	1995-05-10
HUT54151A (en)	1991-01-28
ZA904736B (en)	1992-02-26
IL94763A0 (en)	1991-04-15
NO174053C (no)	1994-03-16
NO902710D0 (no)	1990-06-19
EP0404737A3 (en)	1992-03-11
CA2019251A1 (en)	1990-12-20
NO902710L (no)	1990-12-21
IE902208L (en)	1990-12-20
AU5764990A (en)	1991-01-03
IE902208A1 (en)	1991-01-02
AU634787B2 (en)	1993-03-04
HU903908D0 (en)	1990-11-28
PL164218B1 (pl)	1994-07-29
NO174053B (no)	1993-11-29
YU120290A (sh)	1992-12-21
PL285669A1 (en)	1991-03-11
NZ234157A (en)	1992-09-25
KR910000720A (ko)	1991-01-30
IL94763A (en)	1994-08-26
JPH0331279A (ja)	1991-02-12
IT8920929A0 (it)	1989-06-20

Publication	Publication Date	Title
DE60020994T2 (de)	2006-04-27	Neue verwendung sowie neue n-azabicycloamid-verbindungen
EP1487834B1 (de)	2007-04-25	Aza-bicyclische n-biarylamide mit affinität zum alpha7 nikotinischen acetylcholin-rezeptor
EP0528922B1 (de)	1999-06-16	Neue sulfonylverbindungen
CH667657A5 (de)	1988-10-31	Carbocyclische und heterocyclische carbonylmethylen- und methylpiperidine und -pyrrolidine.
DE69020277T2 (de)	1995-12-21	(+)-Isomere von Endoetheno/Endoethano-epoxymorphinan-Derivaten als Mittel gegen Husten.
WO2003078430A1 (de)	2003-09-25	Essig- und propionsäureamide
EP0149840B1 (de)	1989-04-26	Substituierte 5,11-Dihydro-6H-dibenz(b,e)azepin-6-one, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE60002733T2 (de)	2004-03-18	Diester prodrugs von decahydroischinoline-3-carbonsäure
DD300105A5 (de)	1992-05-21	Neue R(-)3-Quinuliclidinol - Derivate
DE69628200T2 (de)	2003-11-27	Diarylalkenylamin-derivate
DE69113284T2 (de)	1996-02-22	Chinolinderivat.
DE69232484T2 (de)	2002-10-31	Hydroisochinolinderivate
EP0085899B1 (de)	1986-10-29	Neue Pyridobenzodiazepinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0085892B1 (de)	1985-12-18	Substituierte Dibenzodiazepinone, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE3882571T2 (de)	1994-01-20	Sulfonyldecahydro-8H-isochino[2,1-g][1,6]naphthyridine, optische Isomere davon und verwandte Verbindungen.
EP0213293B1 (de)	1992-01-02	In 11-Stellung substituierte 5,11-Dihydro-6H-pyrido-[2,3-b][1,4]benzodiazepin-6-one, Verfahren zur ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0254955A2 (de)	1988-02-03	Substituierte Pyrido-[2,3-b][1,4]benzodiazepin-6-one, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0312895A2 (de)	1989-04-26	Kondensierte Diazepinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE69918046T2 (de)	2005-07-14	Neue basische Derivate von Benz(e)isoindol-1-onen und Pyrrolo(3,4-c)chinolin-1-onen mit 5-HT3-antagonistischer Aktivität, ihre Herstellung und ihre therapeutische Verwendung
EP1651645B1 (de)	2007-02-21	N-biarylamide
DE4131584A1 (de)	1993-03-25	Imidazolylmethyl-pyridine, ihre herstellung und anwendung als pharmazeutika
EP0369286A2 (de)	1990-05-23	Dibenzazepin-Derivate zur Behandlung von akuten und chronischen obstruktiven Atemwegserkrankungen
EP0086982A1 (de)	1983-08-31	Substituierte Thienobenzodiazepinone, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2821813A1 (de)	1979-11-22	Neue, in 11-stellung substituierte 5, 11-dihydro-6h-pyrido eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0085893B1 (de)	1986-05-14	Pyridobenzodiazepinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel