CA1306252C - Derives quinaldinamides et leur preparation - Google Patents

Derives quinaldinamides et leur preparation

Info

Publication number: CA1306252C
Authority: CA; Canada
Prior art keywords: quinaldinamide; acid; derivative; formula; compound
Prior art date: 1986-08-13
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 - Fee Related

Application number

CA000515907A

Other languages

English (en)

Inventor

Mitsuo Masaki

Naoya Moritoh

Koichi Hashimoto

Haruhiko Shinozaki

Toshiro Kamishiro

Masaru Satoh

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.)

Nippon Chemiphar Co Ltd

Original Assignee

Nippon Chemiphar Co Ltd

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.)

1986-08-13

Filing date

1986-08-13

Publication date

1992-08-11

1986-08-13 Application filed by Nippon Chemiphar Co Ltd filed Critical Nippon Chemiphar Co Ltd

1986-08-13 Priority to CA000515907A priority Critical patent/CA1306252C/fr

1992-08-11 Application granted granted Critical

1992-08-11 Publication of CA1306252C publication Critical patent/CA1306252C/fr

2009-08-11 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

WEHFQXPHQWWTGF-UHFFFAOYSA-N 2-quinolin-2-ylacetamide Chemical class C1=CC=CC2=NC(CC(=O)N)=CC=C21 WEHFQXPHQWWTGF-UHFFFAOYSA-N 0.000 title claims abstract description 27
238000002360 preparation method Methods 0.000 title abstract description 36
150000003839 salts Chemical class 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims description 21
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 16
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 13
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
239000001530 fumaric acid Substances 0.000 claims description 5
JGCVEGCWYLFXBA-UHFFFAOYSA-N n-(1-phenyl-3-piperidin-1-ylpropyl)-2-quinolin-2-ylacetamide Chemical compound C=1C=C2C=CC=CC2=NC=1CC(=O)NC(C=1C=CC=CC=1)CCN1CCCCC1 JGCVEGCWYLFXBA-UHFFFAOYSA-N 0.000 claims description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
239000011976 maleic acid Substances 0.000 claims description 2
229940098779 methanesulfonic acid Drugs 0.000 claims description 2
NMIOGVKCNALTSE-UHFFFAOYSA-N n-[1-(3-methylphenyl)-3-piperidin-1-ylpropyl]-2-quinolin-2-ylacetamide Chemical compound CC1=CC=CC(C(CCN2CCCCC2)NC(=O)CC=2N=C3C=CC=CC3=CC=2)=C1 NMIOGVKCNALTSE-UHFFFAOYSA-N 0.000 claims description 2
235000006408 oxalic acid Nutrition 0.000 claims description 2
239000011975 tartaric acid Substances 0.000 claims description 2
235000002906 tartaric acid Nutrition 0.000 claims description 2
TUNWJLLTTGZTNU-UHFFFAOYSA-N n-[1-(4-methoxyphenyl)-3-piperidin-1-ylpropyl]-2-quinolin-2-ylacetamide Chemical compound C1=CC(OC)=CC=C1C(NC(=O)CC=1N=C2C=CC=CC2=CC=1)CCN1CCCCC1 TUNWJLLTTGZTNU-UHFFFAOYSA-N 0.000 claims 1
SFQZDCPSHUAKJY-UHFFFAOYSA-N n-[1-(4-methylphenyl)-3-piperidin-1-ylpropyl]-2-quinolin-2-ylacetamide Chemical compound C1=CC(C)=CC=C1C(NC(=O)CC=1N=C2C=CC=CC2=CC=1)CCN1CCCCC1 SFQZDCPSHUAKJY-UHFFFAOYSA-N 0.000 claims 1
AONYFFNTDZDRIJ-UHFFFAOYSA-N n-[3-(azepan-1-yl)-1-phenylpropyl]-2-quinolin-2-ylacetamide Chemical compound C=1C=C2C=CC=CC2=NC=1CC(=O)NC(C=1C=CC=CC=1)CCN1CCCCCC1 AONYFFNTDZDRIJ-UHFFFAOYSA-N 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 10
-1 amine compound Chemical class 0.000 abstract description 8
208000007502 anemia Diseases 0.000 abstract description 6
239000003158 myorelaxant agent Substances 0.000 abstract description 5
230000002040 relaxant effect Effects 0.000 abstract description 4
238000006482 condensation reaction Methods 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 description 61
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 28
238000000034 method Methods 0.000 description 26
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 21
239000000047 product Substances 0.000 description 20
125000003118 aryl group Chemical group 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
238000007792 addition Methods 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
235000013350 formula milk Nutrition 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
208000002740 Muscle Rigidity Diseases 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
101150041968 CDC13 gene Proteins 0.000 description 11
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 11
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 11
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
229940093499 ethyl acetate Drugs 0.000 description 10
235000019439 ethyl acetate Nutrition 0.000 description 10
PQVWSOJILKYXCV-UHFFFAOYSA-N 2-quinolin-2-ylacetyl chloride Chemical compound C1=CC=CC2=NC(CC(=O)Cl)=CC=C21 PQVWSOJILKYXCV-UHFFFAOYSA-N 0.000 description 8
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
150000008065 acid anhydrides Chemical class 0.000 description 7
239000013078 crystal Substances 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
229940125782 compound 2 Drugs 0.000 description 5
229960002989 glutamic acid Drugs 0.000 description 5
GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
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238000002474 experimental method Methods 0.000 description 4
235000013922 glutamic acid Nutrition 0.000 description 4
239000004220 glutamic acid Substances 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
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235000011152 sodium sulphate Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
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AQRWYAQXDIBCCU-UHFFFAOYSA-N 1-phenyl-3-piperidin-1-ylpropan-1-amine Chemical compound C=1C=CC=CC=1C(N)CCN1CCCCC1 AQRWYAQXDIBCCU-UHFFFAOYSA-N 0.000 description 3
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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RKRRWBZERULWBL-UHFFFAOYSA-N n-(1-phenyl-3-pyrrolidin-1-ylpropyl)-2-quinolin-2-ylacetamide Chemical compound C=1C=C2C=CC=CC2=NC=1CC(=O)NC(C=1C=CC=CC=1)CCN1CCCC1 RKRRWBZERULWBL-UHFFFAOYSA-N 0.000 description 3
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OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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210000003194 forelimb Anatomy 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
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125000005843 halogen group Chemical group 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000000749 insecticidal effect Effects 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
229940080428 lactose 200 mg Drugs 0.000 description 1
RYZCLUQMCYZBJQ-UHFFFAOYSA-H lead(2+);dicarbonate;dihydroxide Chemical compound [OH-].[OH-].[Pb+2].[Pb+2].[Pb+2].[O-]C([O-])=O.[O-]C([O-])=O RYZCLUQMCYZBJQ-UHFFFAOYSA-H 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000028161 membrane depolarization Effects 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
230000003387 muscular Effects 0.000 description 1
210000001087 myotubule Anatomy 0.000 description 1
RIIVGTUMDNURCE-UHFFFAOYSA-N n-[1-(2-methylphenyl)-3-piperidin-1-ylpropyl]-2-quinolin-2-ylacetamide Chemical compound CC1=CC=CC=C1C(NC(=O)CC=1N=C2C=CC=CC2=CC=1)CCN1CCCCC1 RIIVGTUMDNURCE-UHFFFAOYSA-N 0.000 description 1
UFJHGYUYLAJNGD-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-quinolin-2-ylacetamide Chemical compound C1=CC=CC2=NC(CC(=O)NCCN(CC)CC)=CC=C21 UFJHGYUYLAJNGD-UHFFFAOYSA-N 0.000 description 1
VKHHDIRHXMRBDA-UHFFFAOYSA-N n-[3-(dimethylamino)-1-phenylpropyl]-2-quinolin-2-ylacetamide Chemical compound C=1C=C2C=CC=CC2=NC=1CC(=O)NC(CCN(C)C)C1=CC=CC=C1 VKHHDIRHXMRBDA-UHFFFAOYSA-N 0.000 description 1
IOPVRVCLNRDLTA-UHFFFAOYSA-N n-[3-(dipropylamino)-1-phenylpropyl]-2-quinolin-2-ylacetamide Chemical compound C=1C=C2C=CC=CC2=NC=1CC(=O)NC(CCN(CCC)CCC)C1=CC=CC=C1 IOPVRVCLNRDLTA-UHFFFAOYSA-N 0.000 description 1
210000000715 neuromuscular junction Anatomy 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
210000000103 occipital bone Anatomy 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
YTXGZVZCMZIRRQ-UHFFFAOYSA-N oxalic acid 1-phenyl-3-piperidin-1-ylpropan-1-amine Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.C=1C=CC=CC=1C(N)CCN1CCCCC1 YTXGZVZCMZIRRQ-UHFFFAOYSA-N 0.000 description 1
NWEKDUYHRNNGBD-UHFFFAOYSA-N oxalic acid;n-(1-phenyl-3-pyrrolidin-1-ylpropyl)-2-quinolin-2-ylacetamide Chemical compound OC(=O)C(O)=O.C=1C=C2C=CC=CC2=NC=1CC(=O)NC(C=1C=CC=CC=1)CCN1CCCC1 NWEKDUYHRNNGBD-UHFFFAOYSA-N 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
235000002020 sage Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
229960005334 tolperisone Drugs 0.000 description 1
POSZUTFLHGNLHX-KSBRXOFISA-N tris maleate Chemical compound OCC(N)(CO)CO.OCC(N)(CO)CO.OC(=O)\C=C/C(O)=O POSZUTFLHGNLHX-KSBRXOFISA-N 0.000 description 1
231100000691 up-and-down procedure Toxicity 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000515907A 1986-08-13 1986-08-13 Derives quinaldinamides et leur preparation Expired - Fee Related CA1306252C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000515907A CA1306252C (fr)	1986-08-13	1986-08-13	Derives quinaldinamides et leur preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000515907A CA1306252C (fr)	1986-08-13	1986-08-13	Derives quinaldinamides et leur preparation

Publications (1)

Publication Number	Publication Date
CA1306252C true CA1306252C (fr)	1992-08-11

Family

ID=4133724

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000515907A Expired - Fee Related CA1306252C (fr)	1986-08-13	1986-08-13	Derives quinaldinamides et leur preparation

Country Status (1)

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CA (1)	CA1306252C (fr)

1986
- 1986-08-13 CA CA000515907A patent/CA1306252C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1997-08-11	MKLA	Lapsed

Publication	Publication Date	Title
SU820659A3 (ru)	1981-04-07	Способ получени производных 4-амино- 5-АлКилСульфОНилОАНизАМидОВ, иХ СОлЕй,ОКиСЕй, лЕВО- и пРАВОВРАщАющиХизОМЕРОВ /иХ ВАРиАНТы/
JP2624901B2 (ja)	1997-06-25	ナフタレン構造を有する新しい誘導体、その製造方法及びそれを含む薬学的組成物
US4683232A (en)	1987-07-28	Heterocyclic compounds having cardiotonic use
US5708020A (en)	1998-01-13	Arylalkyl(thio)amides
HK32289A (en)	1989-04-28	2-substituted 4-amino-6,7-dimethoxyquinolines
US4267174A (en)	1981-05-12	Immune-stimulating and cancerostatic 1-acyl-2-cyanoaziridines
CH653021A5 (fr)	1985-12-13	Derives piperidino, piperazino et homopiperazino, n-substitues par un groupe heterocyclique aromatique, leur procede de preparation et composition therapeutique les contenant.
CA1184180A (fr)	1985-03-19	Derives de (quinolyl-2, ou -3 ou -4)-1 (piperidyl ou pyrrolidinyl-2 ou -3)-2 ou -3 ethanone ou propanone, procedes pour leur preparation, et leur utilisation comme medicaments
JPS5989625A (ja)	1984-05-23	芳香族置換環状アミジン止瀉剤
JPH0676395B2 (ja)	1994-09-28	新規の（１−ナフチル）ピペラジン誘導体、その製造方法およびそれを含有する薬剤組成物
US3852291A (en)	1974-12-03	Heterocyclic derivatives of phenoxypropanolamines
JPH0226629B2 (fr)	1990-06-12
SU1097198A3 (ru)	1984-06-07	Способ получени производных таурина
US3752823A (en)	1973-08-14	N alkyl tetrahydrocarbazoles
EP0256181B1 (fr)	1991-01-23	Dérivés d'amide de l'acide quinoléine-2-carboxylique et leur préparation
DE2461802A1 (de)	1975-07-17	Pyrazinderivate
EP0326106A2 (fr)	1989-08-02	Alcène-diamines
US3560503A (en)	1971-02-02	Di-lower alkyl-substituted octahydropyrazinopyrimidinones
JPH07113015B2 (ja)	1995-12-06	３―アミノピロール、その製造方法およびその薬品または薬剤としての使用
CA1306252C (fr)	1992-08-11	Derives quinaldinamides et leur preparation
SU1402251A3 (ru)	1988-06-07	Способ получени производных 3-фенил-2-пропенамина в виде геометрических изомеров или их смесей, а также фармакологически приемлемых солей
SU1549480A3 (ru)	1990-03-07	Способ получени производных иминотиазолидина или их гидрохлоридов
US4582838A (en)	1986-04-15	Derivatives of dihydro-1H-pyrrolo[1,2-c]imidazol-3,5-dione as cognition activators
US4353911A (en)	1982-10-12	Indolo(2,3-a)quinolizidines, useful in increasing femoral and vertebral blood flow
DE2609437C2 (fr)	1987-10-01