UA68388C2 - Substituted indole derivatives, pharmaceutical composition and method of synthesis (variants) - Google Patents

Substituted indole derivatives, pharmaceutical composition and method of synthesis (variants) Download PDF

Info

Publication number: UA68388C2
Authority: UA; Ukraine
Prior art keywords: general formula; hexahydro; trans; methyl; hydroxy
Prior art date: 1998-07-31

Application number

UA2001021382A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Boehringer Ingelheim Pharma

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.)

1998-07-31

Filing date

1999-07-22

Publication date

2004-08-16

1999-07-22 Application filed by Boehringer Ingelheim Pharma filed Critical Boehringer Ingelheim Pharma

2004-08-16 Publication of UA68388C2 publication Critical patent/UA68388C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 16
150000002475 indoles Chemical class 0.000 title claims abstract description 5
239000008194 pharmaceutical composition Chemical class 0.000 title claims 2
229940054051 antipsychotic indole derivative Drugs 0.000 title abstract description 3
230000015572 biosynthetic process Effects 0.000 title description 4
238000003786 synthesis reaction Methods 0.000 title description 4
238000004519 manufacturing process Methods 0.000 claims abstract 3
239000003814 drug Substances 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 47
239000001257 hydrogen Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
150000002431 hydrogen Chemical class 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
206010021143 Hypoxia Diseases 0.000 claims description 7
229930195712 glutamate Natural products 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
230000003993 interaction Effects 0.000 claims description 5
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229940126601 medicinal product Drugs 0.000 claims description 4
206010002660 Anoxia Diseases 0.000 claims description 3
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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125000000217 alkyl group Chemical group 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
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230000006793 arrhythmia Effects 0.000 claims description 2
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208000029028 brain injury Diseases 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 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 claims description 2
239000012467 final product Substances 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
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208000031225 myocardial ischemia Diseases 0.000 claims description 2
230000004770 neurodegeneration Effects 0.000 claims description 2
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
230000033764 rhythmic process Effects 0.000 claims description 2
208000005809 status epilepticus Diseases 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims 5
239000013067 intermediate product Substances 0.000 claims 4
125000004433 nitrogen atom Chemical group N* 0.000 claims 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
206010008120 Cerebral ischaemia Diseases 0.000 claims 1
208000001953 Hypotension Diseases 0.000 claims 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims 1
239000002253 acid Substances 0.000 claims 1
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239000000546 pharmaceutical excipient Substances 0.000 claims 1
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238000012876 topography Methods 0.000 claims 1
QGPODKIUJLHCDK-UHFFFAOYSA-N 2,3,3a,4,4a,5-hexahydro-1H-benzo[f]indol-8-ol Chemical class OC=1C=CCC2CC3CCNC3=CC21 QGPODKIUJLHCDK-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 23
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 20
239000002904 solvent Substances 0.000 description 17
239000000243 solution Substances 0.000 description 15
239000012074 organic phase Substances 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 12
108010052164 Sodium Channels Proteins 0.000 description 11
102000018674 Sodium Channels Human genes 0.000 description 11
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 11
239000000203 mixture Substances 0.000 description 11
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
229940049920 malate Drugs 0.000 description 6
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
239000013543 active substance Substances 0.000 description 5
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 5
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
239000011575 calcium Substances 0.000 description 4
229910052791 calcium Inorganic materials 0.000 description 4
230000001419 dependent effect Effects 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
230000004941 influx Effects 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
239000000843 powder Substances 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000028161 membrane depolarization Effects 0.000 description 3
238000011084 recovery Methods 0.000 description 3
229910001415 sodium ion Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
238000003828 vacuum filtration Methods 0.000 description 3
PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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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
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-Chlorosuccinimide Substances ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FVECELJHCSPHKY-UHFFFAOYSA-N Veratridine Natural products C1=C(OC)C(OC)=CC=C1C(=O)OC1C2(O)OC34CC5(O)C(CN6C(CCC(C)C6)C6(C)O)C6(O)C(O)CC5(O)C4CCC2C3(C)CC1 FVECELJHCSPHKY-UHFFFAOYSA-N 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
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239000008346 aqueous phase Substances 0.000 description 2
NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 description 2
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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 2
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BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
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230000000694 effects Effects 0.000 description 1
230000002996 emotional effect Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000005284 excitation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000004907 flux Effects 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
150000002306 glutamic acid derivatives Chemical class 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
230000001146 hypoxic effect Effects 0.000 description 1
QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
208000030159 metabolic disease Diseases 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
208000021722 neuropathic pain Diseases 0.000 description 1
210000000929 nociceptor Anatomy 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000004037 social stress Effects 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940125794 sodium channel blocker Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
230000000946 synaptic effect Effects 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
230000008733 trauma Effects 0.000 description 1
230000002792 vascular Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000811 xylitol Substances 0.000 description 1
235000010447 xylitol Nutrition 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
229960002675 xylitol Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
- 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
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Psychology (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Psychiatry (AREA)
Diabetes (AREA)
Emergency Medicine (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Obesity (AREA)
Endocrinology (AREA)
Hospice & Palliative Care (AREA)
Hematology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

UA2001021382A 1998-07-31 1999-07-22 Substituted indole derivatives, pharmaceutical composition and method of synthesis (variants) UA68388C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19834714A DE19834714A1 (de)	1998-07-31	1998-07-31	Neue 2,3,3a,4,9,9a-Hexahydro-8-hydroxy-1H-ben[f]indole, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
PCT/EP1999/005222 WO2000007986A1 (de)	1998-07-31	1999-07-22	Neue 2,3,3a,4,9,9a-hexahydro-8-hydroxy-1h-benz[f]indole, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel

Publications (1)

Publication Number	Publication Date
UA68388C2 true UA68388C2 (en)	2004-08-16

Family

ID=7876092

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2001021382A UA68388C2 (en)	1998-07-31	1999-07-22	Substituted indole derivatives, pharmaceutical composition and method of synthesis (variants)

Country Status (30)

Country	Link
US (1)	US6051583A (ja)
EP (1)	EP1100780B1 (ja)
JP (1)	JP2002522418A (ja)
KR (1)	KR20010072142A (ja)
CN (1)	CN1147470C (ja)
AT (1)	ATE360611T1 (ja)
AU (1)	AU763834B2 (ja)
BG (1)	BG105178A (ja)
BR (1)	BR9912605A (ja)
CA (1)	CA2336783C (ja)
CO (1)	CO5080748A1 (ja)
DE (2)	DE19834714A1 (ja)
EA (1)	EA003370B1 (ja)
EE (1)	EE200100062A (ja)
ES (1)	ES2285851T3 (ja)
HK (1)	HK1038017A1 (ja)
HU (1)	HUP0103518A3 (ja)
ID (1)	ID28292A (ja)
IL (1)	IL140863A0 (ja)
MY (1)	MY133085A (ja)
NO (1)	NO20010513D0 (ja)
NZ (1)	NZ510246A (ja)
PL (1)	PL345808A1 (ja)
SK (1)	SK1502001A3 (ja)
TR (1)	TR200100316T2 (ja)
TW (1)	TW464643B (ja)
UA (1)	UA68388C2 (ja)
WO (1)	WO2000007986A1 (ja)
YU (1)	YU5501A (ja)
ZA (1)	ZA200007770B (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0002666D0 (en)	2000-02-04	2000-03-29	Univ London	Blockade of voltage dependent sodium channels
PT1458386E (pt) *	2001-12-27	2007-06-04	Ortho Mcneil Pharm Inc	''aroilpirrole-heteroarilo e metanóis úteis para o tratamento de um distúrbio do sistema nervoso central''

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR0151699B1 (ko) *	1989-07-13	1998-10-15	로버트 에이. 아미테이지	(1,2n) 및 (3,2n)-카보사이클릭-2-아미노테트랄린 유도체
JPH06507906A (ja) *	1991-05-20	1994-09-08	ジ・アップジョン・カンパニー	カルボキサミド−（３，２ｎ）−カルボサイクリック−２−アミノテトラリン誘導体
GB9612153D0 (en) *	1996-06-11	1996-08-14	Smithkline Beecham Plc	Compounds

1998
- 1998-07-31 DE DE19834714A patent/DE19834714A1/de not_active Ceased
1999
- 1999-07-22 WO PCT/EP1999/005222 patent/WO2000007986A1/de active IP Right Grant
- 1999-07-22 AT AT99936584T patent/ATE360611T1/de not_active IP Right Cessation
- 1999-07-22 ES ES99936584T patent/ES2285851T3/es not_active Expired - Lifetime
- 1999-07-22 HU HU0103518A patent/HUP0103518A3/hu unknown
- 1999-07-22 CN CNB998089702A patent/CN1147470C/zh not_active Expired - Fee Related
- 1999-07-22 NZ NZ510246A patent/NZ510246A/en unknown
- 1999-07-22 PL PL99345808A patent/PL345808A1/xx not_active Application Discontinuation
- 1999-07-22 EP EP99936584A patent/EP1100780B1/de not_active Expired - Lifetime
- 1999-07-22 IL IL14086399A patent/IL140863A0/xx unknown
- 1999-07-22 AU AU51626/99A patent/AU763834B2/en not_active Ceased
- 1999-07-22 BR BR9912605-2A patent/BR9912605A/pt not_active IP Right Cessation
- 1999-07-22 TR TR2001/00316T patent/TR200100316T2/xx unknown
- 1999-07-22 EA EA200100107A patent/EA003370B1/ru not_active IP Right Cessation
- 1999-07-22 JP JP2000563620A patent/JP2002522418A/ja active Pending
- 1999-07-22 SK SK150-2001A patent/SK1502001A3/sk unknown
- 1999-07-22 YU YU5501A patent/YU5501A/sh unknown
- 1999-07-22 EE EEP200100062A patent/EE200100062A/xx unknown
- 1999-07-22 CA CA002336783A patent/CA2336783C/en not_active Expired - Fee Related
- 1999-07-22 KR KR1020017001334A patent/KR20010072142A/ko not_active Application Discontinuation
- 1999-07-22 ID IDW20010244A patent/ID28292A/id unknown
- 1999-07-22 DE DE59914314T patent/DE59914314D1/de not_active Expired - Fee Related
- 1999-07-22 UA UA2001021382A patent/UA68388C2/uk unknown
- 1999-07-29 MY MYPI99003229A patent/MY133085A/en unknown
- 1999-07-29 TW TW088112896A patent/TW464643B/zh not_active IP Right Cessation
- 1999-07-30 CO CO99048374A patent/CO5080748A1/es unknown
- 1999-07-30 US US09/365,064 patent/US6051583A/en not_active Expired - Lifetime
2000
- 2000-12-21 ZA ZA200007770A patent/ZA200007770B/en unknown
2001
- 2001-01-24 BG BG105178A patent/BG105178A/xx active Pending
- 2001-01-30 NO NO20010513A patent/NO20010513D0/no not_active Application Discontinuation
- 2001-12-19 HK HK01108875A patent/HK1038017A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
TW464643B (en)	2001-11-21
SK1502001A3 (en)	2001-09-11
DE19834714A1 (de)	2000-02-03
HUP0103518A2 (hu)	2002-01-28
BG105178A (en)	2001-12-29
ES2285851T3 (es)	2007-11-16
CA2336783C (en)	2009-04-28
WO2000007986A1 (de)	2000-02-17
AU5162699A (en)	2000-02-28
AU763834B2 (en)	2003-07-31
ID28292A (id)	2001-05-10
HUP0103518A3 (en)	2002-12-28
PL345808A1 (en)	2002-01-02
JP2002522418A (ja)	2002-07-23
TR200100316T2 (tr)	2001-07-23
NZ510246A (en)	2003-08-29
NO20010513L (no)	2001-01-30
EA003370B1 (ru)	2003-04-24
CO5080748A1 (es)	2001-09-25
CN1147470C (zh)	2004-04-28
EA200100107A1 (ru)	2001-08-27
EP1100780B1 (de)	2007-04-25
HK1038017A1 (en)	2002-03-01
CA2336783A1 (en)	2000-02-17
DE59914314D1 (de)	2007-06-06
KR20010072142A (ko)	2001-07-31
EP1100780A1 (de)	2001-05-23
YU5501A (sh)	2003-04-30
ATE360611T1 (de)	2007-05-15
CN1310707A (zh)	2001-08-29
ZA200007770B (en)	2002-01-17
MY133085A (en)	2007-10-31
BR9912605A (pt)	2001-05-02
IL140863A0 (en)	2002-02-10
NO20010513D0 (no)	2001-01-30
US6051583A (en)	2000-04-18
EE200100062A (et)	2002-06-17

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JP2005504823A (ja)	2005-02-17	神経栄養剤としてのトリアゼピン誘導体
WO1995029910A1 (en)	1995-11-09	Imidazolidinedione derivative
CZ2001399A3 (cs)	2001-05-16	Nové 2,3,3a,4,9,9a -hexahydro-8-hydroxy-lHbenz(f)indoly, způsob jejich výroby a použití jako léčiva