IL100384A - Serotonin antagonists their preparation and pharmaceutical compositions containing them - Google Patents

Serotonin antagonists their preparation and pharmaceutical compositions containing them

Info

Publication number: IL100384A
Authority: IL; Israel
Prior art keywords: alkyl; compound; pharmaceutically acceptable; hydrogen; compounds
Prior art date: 1990-12-18

Application number

IL10038491A

Other languages

English (en)

Other versions

IL100384A0 (en

Original Assignee

Sandoz Ag

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.)

1990-12-18

Filing date

1991-12-16

Publication date

1996-05-14

1990-12-18 Priority claimed from GB909027425A external-priority patent/GB9027425D0/en

1990-12-18 Priority claimed from GB909027424A external-priority patent/GB9027424D0/en

1991-06-24 Priority claimed from GB919113596A external-priority patent/GB9113596D0/en

1991-12-16 Application filed by Sandoz Ag filed Critical Sandoz Ag

1992-09-06 Publication of IL100384A0 publication Critical patent/IL100384A0/xx

1996-05-14 Publication of IL100384A publication Critical patent/IL100384A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 5
229940082988 antihypertensives serotonin antagonists Drugs 0.000 title description 2
239000003420 antiserotonin agent Substances 0.000 title description 2
238000002360 preparation method Methods 0.000 title description 2
-1 3,7-disubstituted indole Chemical class 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 44
125000000217 alkyl group Chemical group 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000012458 free base Substances 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
230000036506 anxiety 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
MSALXMDIYCKASR-UHFFFAOYSA-N 7-methoxy-1h-indole-3-carboxylic acid Chemical compound COC1=CC=CC2=C1NC=C2C(O)=O MSALXMDIYCKASR-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims 1
125000006193 alkinyl group Chemical group 0.000 claims 1
125000003368 amide group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
208000020016 psychiatric disease Diseases 0.000 abstract description 3
229940054051 antipsychotic indole derivative Drugs 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
230000000694 effects Effects 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 3
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 3
125000003884 phenylalkyl group Chemical group 0.000 description 3
150000003242 quaternary ammonium salts Chemical class 0.000 description 3
OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000030136 gastric emptying Effects 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
239000002207 metabolite Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
230000011273 social behavior Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-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
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-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
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 description 1
PHMVYPXOSJQLRW-UHFFFAOYSA-N 7-hydroxy-1h-indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CNC2=C1O PHMVYPXOSJQLRW-UHFFFAOYSA-N 0.000 description 1
208000008811 Agoraphobia 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
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000019022 Mood disease Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
206010041243 Social avoidant behaviour 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
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
208000010877 cognitive disease Diseases 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
206010073071 hepatocellular carcinoma Diseases 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 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
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000036544 posture Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000011514 reflex Effects 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/12—Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Epidemiology (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Compounds Of Unknown Constitution (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

IL10038491A 1990-12-18 1991-12-16 Serotonin antagonists their preparation and pharmaceutical compositions containing them IL100384A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB909027425A GB9027425D0 (en)	1990-12-18	1990-12-18	Improvements in or relating to organic compounds
GB909027424A GB9027424D0 (en)	1990-12-18	1990-12-18	Improvements in or relating to organic compounds
GB919113596A GB9113596D0 (en)	1991-06-24	1991-06-24	Improvements in or relating to organic compounds

Publications (2)

Publication Number	Publication Date
IL100384A0 IL100384A0 (en)	1992-09-06
IL100384A true IL100384A (en)	1996-05-14

Family

ID=27265408

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10038491A IL100384A (en)	1990-12-18	1991-12-16	Serotonin antagonists their preparation and pharmaceutical compositions containing them

Country Status (22)

Country	Link
US (2)	US5272154A (de)
EP (1)	EP0491664B1 (de)
JP (1)	JP2740777B2 (de)
KR (1)	KR920011489A (de)
AT (1)	ATE163648T1 (de)
AU (1)	AU651640B2 (de)
CA (1)	CA2057391A1 (de)
CZ (1)	CZ280647B6 (de)
DE (1)	DE69129009T2 (de)
DK (1)	DK0491664T3 (de)
ES (1)	ES2113368T3 (de)
FI (1)	FI102069B1 (de)
GR (1)	GR3026506T3 (de)
HU (1)	HU211081B (de)
IE (1)	IE914387A1 (de)
IL (1)	IL100384A (de)
MX (1)	MX9102582A (de)
MY (1)	MY109983A (de)
NZ (1)	NZ240993A (de)
PT (1)	PT99829B (de)
SG (1)	SG47026A1 (de)
SK (1)	SK278597B6 (de)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5342845A (en) *	1990-08-31	1994-08-30	Nippon Shinyaku Company Limited	Indole derivatives and drugs
IL117438A (en) *	1995-03-16	2001-12-23	Lilly Co Eli	Indazolecarboxamides, their preparation and pharmaceutical compositions containing them
US5654320A (en) *	1995-03-16	1997-08-05	Eli Lilly And Company	Indazolecarboxamides
US6069152A (en) *	1997-10-07	2000-05-30	Eli Lilly And Company	5-HT4 agonists and antagonists
RU2183631C2 (ru) *	2000-09-20	2002-06-20	Институт физико-органической химии и углехимии им.Л.М.Литвиненко НАН Украины	Способ получения 8-метил-8-азабицикло[3,2,1]окт-3-илового эфира индол-3-карбоновой кислоты
AR036041A1 (es) *	2001-06-12	2004-08-04	Upjohn Co	Compuestos aromaticos heterociclicos sustituidos con quinuclidina y composiciones farmaceuticas que los contienen
AR036040A1 (es)	2001-06-12	2004-08-04	Upjohn Co	Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen
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1991
- 1991-12-04 HU HU913792A patent/HU211081B/hu not_active IP Right Cessation
- 1991-12-16 DE DE69129009T patent/DE69129009T2/de not_active Expired - Fee Related
- 1991-12-16 CZ CS913815A patent/CZ280647B6/cs not_active IP Right Cessation
- 1991-12-16 EP EP91810981A patent/EP0491664B1/de not_active Expired - Lifetime
- 1991-12-16 DK DK91810981T patent/DK0491664T3/da active
- 1991-12-16 ES ES91810981T patent/ES2113368T3/es not_active Expired - Lifetime
- 1991-12-16 IL IL10038491A patent/IL100384A/en not_active IP Right Cessation
- 1991-12-16 SK SK3815-91A patent/SK278597B6/sk unknown
- 1991-12-16 AT AT91810981T patent/ATE163648T1/de not_active IP Right Cessation
- 1991-12-16 MX MX9102582A patent/MX9102582A/es unknown
- 1991-12-16 SG SG1996002729A patent/SG47026A1/en unknown
- 1991-12-16 AU AU89791/91A patent/AU651640B2/en not_active Ceased
- 1991-12-16 FI FI915920A patent/FI102069B1/fi active IP Right Grant
- 1991-12-16 NZ NZ240993A patent/NZ240993A/en unknown
- 1991-12-16 MY MYPI91002317A patent/MY109983A/en unknown
- 1991-12-17 CA CA002057391A patent/CA2057391A1/en not_active Abandoned
- 1991-12-17 PT PT99829A patent/PT99829B/pt not_active IP Right Cessation
- 1991-12-17 JP JP3333271A patent/JP2740777B2/ja not_active Expired - Lifetime
- 1991-12-17 KR KR1019910023435A patent/KR920011489A/ko not_active Ceased
- 1991-12-17 IE IE438791A patent/IE914387A1/en not_active Application Discontinuation
- 1991-12-18 US US07/809,815 patent/US5272154A/en not_active Expired - Fee Related
1995
- 1995-04-21 US US08/426,558 patent/US5543426A/en not_active Expired - Fee Related
1998
- 1998-04-03 GR GR980400689T patent/GR3026506T3/el unknown

Also Published As

Publication number	Publication date
FI102069B (fi)	1998-10-15
SK278597B6 (en)	1997-11-05
EP0491664A1 (de)	1992-06-24
PT99829B (pt)	2000-08-31
JP2740777B2 (ja)	1998-04-15
DE69129009T2 (de)	1998-07-23
MY109983A (en)	1997-10-31
IE914387A1 (en)	1992-07-01
AU8979191A (en)	1992-06-25
NZ240993A (en)	1994-08-26
CS381591A3 (en)	1992-07-15
DE69129009D1 (de)	1998-04-09
DK0491664T3 (da)	1998-09-28
FI915920A0 (fi)	1991-12-16
US5272154A (en)	1993-12-21
EP0491664B1 (de)	1998-03-04
ATE163648T1 (de)	1998-03-15
SG47026A1 (en)	1998-03-20
KR920011489A (ko)	1992-07-24
HU913792D0 (en)	1992-02-28
FI102069B1 (fi)	1998-10-15
ES2113368T3 (es)	1998-05-01
AU651640B2 (en)	1994-07-28
JPH04308590A (ja)	1992-10-30
US5543426A (en)	1996-08-06
PT99829A (pt)	1992-12-31
HU211081B (en)	1995-10-30
HUT61543A (en)	1993-01-28
CZ280647B6 (cs)	1996-03-13
CA2057391A1 (en)	1992-06-19
MX9102582A (es)	1993-01-01
GR3026506T3 (en)	1998-07-31
IL100384A0 (en)	1992-09-06
FI915920L (fi)	1992-06-19

Legal Events

Date	Code	Title
1996-10-16	FF	Patent granted
1996-12-05	KB	Patent renewed
1997-11-20	HC	Change of name of proprietor(s)
1998-04-05	KB	Patent renewed
2002-08-14	MM9K	Patent not in force due to non-payment of renewal fees

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CA2066640C (en)	2000-08-01	Heterocyclic compounds
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RU2098415C1 (ru)	1997-12-10	Способ получения производных замещенного бензофурана или их фармацевтически приемлемых солей
JP3315144B2 (ja)	2002-08-19	置換イミダゾール−２−オンの誘導体及びその製造方法
JPH02503569A (ja)	1990-10-25	新規な化合物
JPH06503332A (ja)	1994-04-14	ハロゲン化安息香酸のアザ二環式アミドまたはエステル
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JP3140155B2 (ja)	2001-03-05	Ｎ，ｎ’−ジ置換アミド誘導体
CA2042443A1 (en)	1991-11-15	Tricyclic compounds
RU2058985C1 (ru)	1996-04-27	Производные индола, способ их получения и фармацевтическая композиция для лечения психических расстройств на их основе
JPH06510064A (ja)	1994-11-10	置換イミダゾベンズオキサジン−１−オンの誘導体及び該誘導体の製造方法
HU217427B (hu)	2000-01-28	Heterociklusos vegyületek, ezeket hatóanyagként tartalmazó gyógyászati készítmények, és eljárás előállításukra
PL168230B1 (pl)	1996-01-31	Sposób wytwarzania 3,7-dipodstawionych pochodnych indolu
US5225419A (en)	1993-07-06	Certain 1,8-ethano or propano-1,4-dihydro-4-oxo-quinoline-3-carboxamides and derivatives thereof
FR2694292A1 (fr)	1994-02-04	Dérivés de benzimidazole-2-thione-, leur préparation et leur application en tant que médicament.
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JPWO1990014347A1 (ja)	1991-05-09	インドール誘導体及び医薬
JPH05271230A (ja)	1993-10-19	ジアザビシクロ誘導体