JPH0447673B2 - - Google Patents

Info

Publication number: JPH0447673B2
Authority: JP; Japan
Prior art keywords: formula; compound; alkyl group; add; mol
Prior art date: 1983-12-12
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP59262636A

Other languages

English (en)

Japanese (ja)

Other versions

JPS60149588A (ja

Inventor

Bigu Denisu

Moreru Kuroodo

Seburin Mireiru

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Synthelabo SA

Original Assignee

Synthelabo SA

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.)

1983-12-12

Filing date

1984-12-11

Publication date

1992-08-04

1984-12-11 Application filed by Synthelabo SA filed Critical Synthelabo SA

1985-08-07 Publication of JPS60149588A publication Critical patent/JPS60149588A/ja

1992-08-04 Publication of JPH0447673B2 publication Critical patent/JPH0447673B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 33
238000000034 method Methods 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
JLTRNSWADPSQBA-UHFFFAOYSA-N 4-azatricyclo[5.3.1.04,11]undeca-1(11),2,5,7,9-pentaene Chemical class C1=CC2=CC=CC3=C2N1C=C3 JLTRNSWADPSQBA-UHFFFAOYSA-N 0.000 claims description 4
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
150000002475 indoles Chemical class 0.000 claims 2
239000004480 active ingredient Substances 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
229940124597 therapeutic agent Drugs 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 17
239000000203 mixture Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical class 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000010410 layer Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
229910052786 argon Inorganic materials 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000012300 argon atmosphere Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
-1 alkyl compound Chemical class 0.000 description 4
238000010992 reflux Methods 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
229940099112 cornstarch Drugs 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
WVEBQVBMPNXJCK-UHFFFAOYSA-N hexane;trimethylalumane Chemical compound C[Al](C)C.CCCCCC WVEBQVBMPNXJCK-UHFFFAOYSA-N 0.000 description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
239000002253 acid Substances 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011734 sodium Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000011343 solid material Substances 0.000 description 2
SKJFTWMIXZFOBU-WLHGVMLRSA-N (e)-but-2-enedioic acid;1h-indole Chemical compound OC(=O)\C=C\C(O)=O.C1=CC=C2NC=CC2=C1 SKJFTWMIXZFOBU-WLHGVMLRSA-N 0.000 description 1
UQSBOFBTKISJCK-UHFFFAOYSA-N 3-(4,5-dihydro-1H-imidazol-2-yl)-3-methyl-4-azatricyclo[5.3.1.04,11]undeca-1(10),7(11),8-triene Chemical compound C1C(C2=3)=CC=CC=3CCN2C1(C)C1=NCCN1 UQSBOFBTKISJCK-UHFFFAOYSA-N 0.000 description 1
WVBHCUWSWTXWHJ-UHFFFAOYSA-N 3-(4,5-dihydro-1H-imidazol-2-yl)-9-methyl-3-propyl-4-azatricyclo[5.3.1.04,11]undeca-1(10),7(11),8-triene Chemical compound C1C(C2=3)=CC(C)=CC=3CCN2C1(CCC)C1=NCCN1 WVBHCUWSWTXWHJ-UHFFFAOYSA-N 0.000 description 1
ZWOGGICAYONHFT-UHFFFAOYSA-N 4,5-dihydro-pyrrolo[3,2,1-hi]indole-2-carboxylic acid ethyl ester Chemical compound CCOC(=O)C1=CC2=CC=CC3=C2N1CC3 ZWOGGICAYONHFT-UHFFFAOYSA-N 0.000 description 1
FSTVICMJCCOMTN-UHFFFAOYSA-N 5-methyl-1-nitroso-2,3-dihydroindole Chemical compound CC1=CC=C2N(N=O)CCC2=C1 FSTVICMJCCOMTN-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
206010033799 Paralysis Diseases 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000000670 adrenergic alpha-2 receptor antagonist Substances 0.000 description 1
239000000556 agonist Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229960002896 clonidine Drugs 0.000 description 1
229960003920 ***e Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
GTXQUUOBEPXOMP-UHFFFAOYSA-N ethyl 2-[(5-methyl-2,3-dihydroindol-1-yl)imino]propanoate Chemical compound CC1=CC=C2N(N=C(C)C(=O)OCC)CCC2=C1 GTXQUUOBEPXOMP-UHFFFAOYSA-N 0.000 description 1
AVBDICWQVWLMKO-UHFFFAOYSA-N ethyl 4-azatricyclo[5.3.1.04,11]undeca-1(10),7(11),8-triene-3-carboxylate Chemical compound CCOC(=O)C1CC2=CC=CC3=C2N1CC3 AVBDICWQVWLMKO-UHFFFAOYSA-N 0.000 description 1
ZHCVPFBBHUOFDP-UHFFFAOYSA-N ethyl 9-methyl-4-azatricyclo[5.3.1.04,11]undeca-1(10),7(11),8-triene-3-carboxylate Chemical compound CCOC(=O)C1CC2=CC(C)=CC3=C2N1CC3 ZHCVPFBBHUOFDP-UHFFFAOYSA-N 0.000 description 1
SEYWHHOCPRIAIS-UHFFFAOYSA-N ethyl 9-methyl-4-azatricyclo[5.3.1.04,11]undeca-1(11),2,7,9-tetraene-3-carboxylate Chemical compound CCOC(=O)C1=CC2=CC(C)=CC3=C2N1CC3 SEYWHHOCPRIAIS-UHFFFAOYSA-N 0.000 description 1
229940117360 ethyl pyruvate Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
VUSYGSNEEYEGGX-UHFFFAOYSA-N indol-1-amine Chemical compound C1=CC=C2N(N)C=CC2=C1 VUSYGSNEEYEGGX-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
229960001289 prazosin Drugs 0.000 description 1
150000005592 pyrroloindoles Chemical class 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
210000001177 vas deferen Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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, ***e
- 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
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Pain & Pain Management (AREA)
Obesity (AREA)
Hematology (AREA)
Child & Adolescent Psychology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

JP59262636A 1983-12-12 1984-12-11 インドール誘導体およびその医薬への応用 Granted JPS60149588A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR8319850		1983-12-12
FR8319850A FR2556345B3 (fr)	1983-12-12	1983-12-12	Derive de pyrrolo(3,2,1-hi) indole, sa preparatio n et son application en therapeutique
FR8414839		1984-09-27

Publications (2)

Publication Number	Publication Date
JPS60149588A JPS60149588A (ja)	1985-08-07
JPH0447673B2 true JPH0447673B2 (xx)	1992-08-04

Family

ID=9295079

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59262636A Granted JPS60149588A (ja)	1983-12-12	1984-12-11	インドール誘導体およびその医薬への応用

Country Status (4)

Country	Link
JP (1)	JPS60149588A (xx)
CA (1)	CA1238326A (xx)
FR (1)	FR2556345B3 (xx)
ZA (1)	ZA849645B (xx)

1983
- 1983-12-12 FR FR8319850A patent/FR2556345B3/fr not_active Expired
1984
- 1984-12-11 ZA ZA849645A patent/ZA849645B/xx unknown
- 1984-12-11 JP JP59262636A patent/JPS60149588A/ja active Granted
- 1984-12-11 CA CA000469792A patent/CA1238326A/en not_active Expired

Also Published As

Publication number	Publication date
CA1238326A (en)	1988-06-21
ZA849645B (en)	1985-07-31
JPS60149588A (ja)	1985-08-07
FR2556345B3 (fr)	1986-07-11
FR2556345A1 (fr)	1985-06-14

Publication	Publication Date	Title
EP0268793A1 (en)	1988-06-01	Aminoalkyl tetracyclic benzodiazepines, a process for their preparation and their use as medicaments
JPH0347179A (ja)	1991-02-28	Ｎ―ヘテロアリール―４―キノリンアミンおよびその製造法
HU190984B (en)	1986-12-28	Process for producing new furo-, thieno- or pinolo-azepin derivatives
US4567177A (en)	1986-01-28	Imidazoline derivatives as α2 -antagonists
JPH04266873A (ja)	1992-09-22	ピペリジン誘導体
WO1995001334A1 (fr)	1995-01-12	Composes indoliques derives d'arylamines comme ligands selectifs des recepteurs 5ht1d et 5ht¿1b?
JPH0447673B2 (xx)	1992-08-04
SU908248A3 (ru)	1982-02-23	Способ получени дибензо- [а,D-ЦИКЛООКТЕН-6,12-ИМИНОВ ИЛИ ИХ ФАРМАЦЕВТИЧЕСКИ ПРИЕМЛЕМЫХ СОЛЕЙ
US5726323A (en)	1998-03-10	4- and 6-carbamates related to physostigmine and intermediates for the preparation thereof
JP5143326B2 (ja)	2013-02-13	６−（４−クロロフェニル）−２，２−ジメチル−７−フェニル−２，３−ジヒドロ−１ｈ−ピロリジン−５−イル酢酸の製造法
KR910005851B1 (ko)	1991-08-05	피롤로[3,2,1-hi]인돌유도체 및 약학적으로 허용되는 그의 산부가염을 제조하는 방법
JPH0395161A (ja)	1991-04-19	（１，２，３，４―テトラヒドロ‐９‐アクリジンイミノ）シクロヘキサンカルボン酸および関連化合物
JPH02169571A (ja)	1990-06-29	置換アリルアミン誘導体
EP0531078B1 (en)	1996-06-05	(R)-3-Methoxy-4- 1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-ylmethyl -N-(2-methylsulphonyl)benzamide in crystalline form
EP0319073B1 (en)	1995-08-23	Cyclo-octane neuroprotective agents
JPS6230779A (ja)	1987-02-09	新規化合物，その製法及びそれを含む医薬組成物
JPS59219283A (ja)	1984-12-10	スピロ〔インドロ〔１，７ａｂ〕〔１，５〕ベンゾジアゼピン−２，４′−ピペリジン〕類およびそれらの中間体
JPH10505610A (ja)	1998-06-02	Ｒ（＋）１，２，３，６−テトラヒドロ−４−フェニル−１−〔（３−フェニル−３−シクロヘキセン−１−イル）メチル〕ピリジン、中枢神経系薬剤のための改善された方法
JPH02131485A (ja)	1990-05-21	３−置換テトラヒドロチオピラノ〔２，３−ｂ〕インドール誘導体及びその中間体
JP4353570B2 (ja)	2009-10-28	Ｎ−ヒドロキシ尿素誘導体
JP5009280B2 (ja)	2012-08-22	６−（４−クロロフェニル）−２，２−ジメチル−７−フェニル−２，３−ジヒドロ−１ｈ−ピロリジン−１−イル酢酸の結晶多形
WO1991018900A1 (fr)	1991-12-12	Derive de tetrahydroimidazopyridine ou son sel
FR2565230A1 (fr)	1985-12-06	Derives de (1h-dihydro-4,5 imidazolyl-2)-2 hexahydro-1,2,4,5,6,7 azepino (3,2,1-hi) indole, leur preparation et leur application en therapeutique
CZ20022500A3 (cs)	2003-05-14	Způsob přípravy 6-(4-chlorophenyI)-2,2 dimethyl-7-fenyl-2,3-dihydro-lH-pyrrolizin-5- yloctové kyseliny
FR2559485A2 (fr)	1985-08-16	Derives de pyrrolo-quinoline, leur preparation et leur application en therapeutique