UA71911C2 - B-carboline derivatives, methods for the preparation thereof and medicament based thereon - Google Patents

B-carboline derivatives, methods for the preparation thereof and medicament based thereon Download PDF

Info

Publication number: UA71911C2
Authority: UA; Ukraine
Prior art keywords: methoxy; radical; group; alkyl; hydrogen atom
Prior art date: 1998-03-17

Application number

UA2000105839A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Macef

Bezene Iscovesco Lab

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.)

1998-03-17

Filing date

1999-03-17

Publication date

2005-01-17

1998-03-17 Priority claimed from US09/042,990 external-priority patent/US6048868A/en

1999-03-17 Application filed by Macef, Bezene Iscovesco Lab filed Critical Macef

2005-01-17 Publication of UA71911C2 publication Critical patent/UA71911C2/uk

Links

238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title description 7
239000003814 drug Substances 0.000 title description 2
125000000217 alkyl group Chemical group 0.000 claims abstract description 52
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 38
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 36
125000003545 alkoxy group Chemical group 0.000 claims abstract description 27
229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
125000004434 sulfur atom Chemical group 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 48
-1 Ka - alkyl Chemical group 0.000 claims description 46
229910052736 halogen Inorganic materials 0.000 claims description 42
150000002367 halogens Chemical class 0.000 claims description 41
239000000203 mixture Substances 0.000 claims description 32
125000004663 dialkyl amino group Chemical group 0.000 claims description 25
150000003254 radicals Chemical class 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 22
DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 claims description 22
125000003282 alkyl amino group Chemical group 0.000 claims description 20
YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 claims description 19
229960003987 melatonin Drugs 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
230000000694 effects Effects 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 14
230000000147 hypnotic effect Effects 0.000 claims description 14
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
125000004076 pyridyl group Chemical group 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
ZIXWTPREILQLAC-UHFFFAOYSA-N isoquinolin-8-ol Chemical compound C1=NC=C2C(O)=CC=CC2=C1 ZIXWTPREILQLAC-UHFFFAOYSA-N 0.000 claims description 12
239000003153 chemical reaction reagent Substances 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
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 claims description 6
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239000000126 substance Substances 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
ZUVKZCTUVRLOAQ-UHFFFAOYSA-N quinolizin-4-one Chemical compound C1=CC=CN2C(=O)C=CC=C21 ZUVKZCTUVRLOAQ-UHFFFAOYSA-N 0.000 claims description 5
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RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 claims description 4
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125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
125000001207 fluorophenyl group Chemical group 0.000 claims description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
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239000013543 active substance Substances 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
238000010531 catalytic reduction reaction Methods 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
239000003158 myorelaxant agent Substances 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 11
230000001670 myorelaxant effect Effects 0.000 claims 1
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125000000547 substituted alkyl group Chemical group 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 18
125000003118 aryl group Chemical group 0.000 abstract description 17
125000000753 cycloalkyl group Chemical group 0.000 abstract description 13
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 6
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125000005843 halogen group Chemical group 0.000 abstract description 4
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238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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239000000047 product Substances 0.000 description 22
235000019439 ethyl acetate Nutrition 0.000 description 21
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238000001819 mass spectrum Methods 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 16
241000282472 Canis lupus familiaris Species 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 15
238000001704 evaporation Methods 0.000 description 15
239000002904 solvent Substances 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
125000004390 alkyl sulfonyl group Chemical group 0.000 description 13
238000010992 reflux Methods 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
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ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 12
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 12
239000008096 xylene Substances 0.000 description 12
239000003480 eluent Substances 0.000 description 11
238000001914 filtration Methods 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
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QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
238000009826 distribution Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
241000287828 Gallus gallus Species 0.000 description 9
235000013330 chicken meat Nutrition 0.000 description 9
206010041349 Somnolence Diseases 0.000 description 8
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125000004414 alkyl thio group Chemical group 0.000 description 7
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125000004659 aryl alkyl thio group Chemical group 0.000 description 7
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125000004104 aryloxy group Chemical group 0.000 description 7
239000012043 crude product Substances 0.000 description 7
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239000000902 placebo Substances 0.000 description 7
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229940125898 compound 5 Drugs 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
230000003400 hallucinatory effect Effects 0.000 description 1
125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
125000003106 haloaryl group Chemical group 0.000 description 1
125000004997 halocarbonyl group Chemical group 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
235000003642 hunger Nutrition 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
210000003016 hypothalamus Anatomy 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
230000004118 muscle contraction Effects 0.000 description 1
MMDQDKPDWJZCKM-UHFFFAOYSA-N n-[2-(7-methoxynaphthalen-1-yl)ethyl]-2-phenylacetamide Chemical compound C12=CC(OC)=CC=C2C=CC=C1CCNC(=O)CC1=CC=CC=C1 MMDQDKPDWJZCKM-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
210000004237 neck muscle Anatomy 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000004999 nitroaryl group Chemical group 0.000 description 1
LTHCSWBWNVGEFE-UHFFFAOYSA-N octanamide Chemical compound CCCCCCCC(N)=O LTHCSWBWNVGEFE-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
210000000062 pectoralis major Anatomy 0.000 description 1
229960002275 pentobarbital sodium Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
125000006684 polyhaloalkyl group Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003368 psychostimulant agent Substances 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
230000004599 slow eye movement Effects 0.000 description 1
230000037322 slow-wave sleep Effects 0.000 description 1
239000012453 solvate Substances 0.000 description 1
230000037351 starvation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
230000001360 synchronised effect Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
230000007704 transition Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- 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
- A61P15/18—Feminine contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- A61P25/04—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
- A61P25/18—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
- A61P25/22—Anxiolytics
- 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
- A61P35/00—Antineoplastic agents
- 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
- 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
- C07D471/04—Ortho-condensed systems
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Gynecology & Obstetrics (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Anesthesiology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)

UA2000105839A 1998-03-17 1999-03-17 B-carboline derivatives, methods for the preparation thereof and medicament based thereon UA71911C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US09/042,990 US6048868A (en)	1994-09-14	1998-03-17	Melatonin-antagonist β-carboline derivatives and analogues thereof containing naphthalenic structure, process for their preparation and their use as medicinal products
PCT/IB1999/000494 WO1999047521A1 (en)	1998-03-17	1999-03-17	HYPNOTIC β-CARBOLINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS MEDICINAL PRODUCTS

Publications (1)

Publication Number	Publication Date
UA71911C2 true UA71911C2 (en)	2005-01-17

Family

ID=21924862

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2000105839A UA71911C2 (en)	1998-03-17	1999-03-17	B-carboline derivatives, methods for the preparation thereof and medicament based thereon

Country Status (24)

Country	Link
EP (1)	EP1064284B1 (de)
JP (1)	JP4333036B2 (de)
CN (1)	CN1115342C (de)
AR (1)	AR018767A1 (de)
AT (1)	ATE215087T1 (de)
AU (1)	AU752364B2 (de)
BG (1)	BG63973B1 (de)
BR (1)	BR9908833A (de)
CA (1)	CA2324270A1 (de)
DE (1)	DE69901098T2 (de)
DK (1)	DK1064284T3 (de)
ES (1)	ES2174632T3 (de)
HU (1)	HUP0101234A3 (de)
IL (1)	IL138442A (de)
IS (1)	IS2199B (de)
NO (1)	NO317296B1 (de)
NZ (1)	NZ506913A (de)
PL (1)	PL193450B1 (de)
PT (1)	PT1064284E (de)
RU (1)	RU2210571C2 (de)
SK (1)	SK284387B6 (de)
TR (1)	TR200003596T2 (de)
UA (1)	UA71911C2 (de)
WO (1)	WO1999047521A1 (de)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2824829B1 (fr) *	2001-05-16	2005-06-03	Macef	Nouveaux derives de dihydroimidazo [5,1-a]-beta-carboline, leur procede de preparation et leur application a titre de medicament
FR2904973A1 (fr) *	2006-08-18	2008-02-22	Fourtillan Snc	Derives de 1-methylidene-pyrido[3,4-b]indole et leur utilisation en therapeutique.
FR2916200A1 (fr) *	2007-05-18	2008-11-21	Fourtillan Snc	Nouveaux derives des 1,2,3,4,6,7,12,12a-octahydro pyrazino[1',2':1,6]pyrido[3,4-b]indoles, leur preparation et leur utilisation en therapeutique
KR101614723B1 (ko)	2008-01-11	2016-04-22	알바니 몰레큘라 리써치, 인크.	Ｍｃｈ 길항물질로서 (1-아지논)-치환된 피리도인돌
US8618299B2 (en)	2009-07-01	2013-12-31	Albany Molecular Research, Inc.	Azinone-substituted azapolycycle MCH-1 antagonists, methods of making, and use thereof
JP2012532144A (ja)	2009-07-01	2012-12-13	アルバニーモレキュラーリサーチ，インコーポレイテッド	アジノン置換アゼピノ［ｂ］インドールおよびピリド−ピロロ−アゼピンｍｃｈ−１拮抗薬、ならびにその作製方法および使用
US9073925B2 (en)	2009-07-01	2015-07-07	Albany Molecular Research, Inc.	Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof
WO2011003007A1 (en)	2009-07-01	2011-01-06	Albany Molecular Research, Inc.	Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof
US8993765B2 (en)	2010-12-21	2015-03-31	Albany Molecular Research, Inc.	Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof
US8697700B2 (en)	2010-12-21	2014-04-15	Albany Molecular Research, Inc.	Piperazinone-substituted tetrahydro-carboline MCH-1 antagonists, methods of making, and uses thereof
FI130627B (en) *	2021-03-31	2023-12-18	Equinorm Ltd	Novel heterocyclic compounds and their use

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5283343A (en) *	1987-08-17	1994-02-01	Whitby Research, Inc.	2-aryl substituted N-acetyltryptamines and process of preparing such
HU207070B (en) *	1990-10-31	1993-03-01	Richter Gedeon Vegyeszet	Process for producing 1beta-ethyl-1alpha-hydroxymethyl-1,2,3,4,6,712,12balpha-octahydroindolo(2,3-a) quinolizine
RU2067980C1 (ru) *	1992-06-30	1996-10-20	Глэксо Груп Лимитед	Производные лактама и фармацевтическая композиция, являющаяся антагонистом 5-окситраптамина /5-нт/ на 5- нт3 -рецепторах или их физиологически приемлемые соли и соловаты
RU2068847C1 (ru) *	1994-05-18	1996-11-10	Всероссийский научный центр по безопасности биологически активных веществ	ПРОИЗВОДНЫЕ 3,4-ДИГИДРО- ИЛИ 1,2,3,4-ТЕТРАГИДРО- β -КАРБОЛИНОВ ИЛИ ИХ СОЛИ С ОРГАНИЧЕСКИМИ ИЛИ НЕОРГАНИЧЕСКИМИ КИСЛОТАМИ, ПРОЯВЛЯЮЩИЕ АНТИМИКРОБНУЮ АКТИВНОСТЬ
FR2724384B1 (fr) *	1994-09-14	1999-04-16	Cemaf	Nouveaux derives de la 3,4-dihydro beta-carboline agonistes de la melatonine, leur procede de preparation et leur utilisation a titre de medicament

1999
- 1999-03-17 HU HU0101234A patent/HUP0101234A3/hu unknown
- 1999-03-17 DK DK99939844T patent/DK1064284T3/da active
- 1999-03-17 TR TR2000/03596T patent/TR200003596T2/xx unknown
- 1999-03-17 RU RU2000126288/04A patent/RU2210571C2/ru not_active IP Right Cessation
- 1999-03-17 CA CA002324270A patent/CA2324270A1/en not_active Abandoned
- 1999-03-17 EP EP99939844A patent/EP1064284B1/de not_active Expired - Lifetime
- 1999-03-17 IL IL138442A patent/IL138442A/en not_active IP Right Cessation
- 1999-03-17 AU AU32707/99A patent/AU752364B2/en not_active Ceased
- 1999-03-17 JP JP2000536716A patent/JP4333036B2/ja not_active Expired - Fee Related
- 1999-03-17 CN CN99805687A patent/CN1115342C/zh not_active Expired - Fee Related
- 1999-03-17 AR ARP990101166A patent/AR018767A1/es active IP Right Grant
- 1999-03-17 DE DE69901098T patent/DE69901098T2/de not_active Expired - Lifetime
- 1999-03-17 NZ NZ506913A patent/NZ506913A/en unknown
- 1999-03-17 WO PCT/IB1999/000494 patent/WO1999047521A1/en not_active Ceased
- 1999-03-17 UA UA2000105839A patent/UA71911C2/uk unknown
- 1999-03-17 ES ES99939844T patent/ES2174632T3/es not_active Expired - Lifetime
- 1999-03-17 BR BR9908833-9A patent/BR9908833A/pt not_active Application Discontinuation
- 1999-03-17 SK SK1385-2000A patent/SK284387B6/sk not_active IP Right Cessation
- 1999-03-17 PL PL99342929A patent/PL193450B1/pl not_active IP Right Cessation
- 1999-03-17 PT PT99939844T patent/PT1064284E/pt unknown
- 1999-03-17 AT AT99939844T patent/ATE215087T1/de not_active IP Right Cessation
2000
- 2000-09-12 IS IS5627A patent/IS2199B/is unknown
- 2000-09-14 BG BG104768A patent/BG63973B1/bg unknown
- 2000-09-15 NO NO20004638A patent/NO317296B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
HUP0101234A3 (en)	2002-12-28
NO20004638L (no)	2000-11-16
WO1999047521A1 (en)	1999-09-23
EP1064284A1 (de)	2001-01-03
PL342929A1 (en)	2001-07-16
CA2324270A1 (en)	1999-09-23
JP2002506867A (ja)	2002-03-05
AR018767A1 (es)	2001-12-12
BG63973B1 (bg)	2003-08-29
NO317296B1 (no)	2004-10-04
DK1064284T3 (da)	2002-07-22
EP1064284B1 (de)	2002-03-27
IL138442A0 (en)	2001-10-31
ATE215087T1 (de)	2002-04-15
PT1064284E (pt)	2002-09-30
IS2199B (is)	2007-02-15
NO20004638D0 (no)	2000-09-15
CN1299361A (zh)	2001-06-13
BG104768A (en)	2001-05-31
DE69901098T2 (de)	2002-11-21
SK13852000A3 (sk)	2001-09-11
HUP0101234A2 (hu)	2001-12-28
CN1115342C (zh)	2003-07-23
ES2174632T3 (es)	2002-11-01
PL193450B1 (pl)	2007-02-28
BR9908833A (pt)	2000-11-21
JP4333036B2 (ja)	2009-09-16
DE69901098D1 (de)	2002-05-02
RU2210571C2 (ru)	2003-08-20
TR200003596T2 (tr)	2001-04-20
IS5627A (is)	2000-09-12
IL138442A (en)	2006-12-10
AU3270799A (en)	1999-10-11
AU752364B2 (en)	2002-09-19
SK284387B6 (sk)	2005-02-04
NZ506913A (en)	2003-07-25

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