JPS632949B2 - - Google Patents

Info

Publication number: JPS632949B2
Authority: JP; Japan
Prior art keywords: formula; diethoxybutylamine; diethoxybutylammonium; bis; succinate
Prior art date: 1983-12-13
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

Application number

JP58235622A

Other languages

English (en)

Japanese (ja)

Other versions

JPS60126252A (ja

Inventor

Yukio Yanagimoto

Yoshio Fukuda

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.)

Individual

Original Assignee

Individual

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.)

1983-12-13

Filing date

1983-12-13

Publication date

1988-01-21

1983-12-13 Application filed by Individual filed Critical Individual

1983-12-13 Priority to JP58235622A priority Critical patent/JPS60126252A/ja

1985-07-05 Publication of JPS60126252A publication Critical patent/JPS60126252A/ja

1988-01-21 Publication of JPS632949B2 publication Critical patent/JPS632949B2/ja

Status Granted legal-status Critical Current

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
235000019441 ethanol Nutrition 0.000 claims description 8
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 5
-1 aliphatic carboxylate Chemical class 0.000 claims description 3
210000003169 central nervous system Anatomy 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
230000002401 inhibitory effect Effects 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
125000001931 aliphatic group Chemical group 0.000 claims 1
150000001734 carboxylic acid salts Chemical class 0.000 claims 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 16
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 12
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 6
239000001530 fumaric acid Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
238000009472 formulation Methods 0.000 description 5
241000699670 Mus sp. Species 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
239000001384 succinic acid Substances 0.000 description 4
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 2
GFLPSABXBDCMCN-UHFFFAOYSA-N 4,4-diethoxybutan-1-amine Chemical compound CCOC(OCC)CCCN GFLPSABXBDCMCN-UHFFFAOYSA-N 0.000 description 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229960003692 gamma aminobutyric acid Drugs 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
230000006742 locomotor activity Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000002243 precursor Substances 0.000 description 2
230000001629 suppression Effects 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
XJHNCGVHPLDMRK-UHFFFAOYSA-N 4,4-dimethoxybutanenitrile Chemical compound COC(OC)CCC#N XJHNCGVHPLDMRK-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003874 central nervous system depressant Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000011570 nicotinamide Substances 0.000 description 1
229960003966 nicotinamide Drugs 0.000 description 1
235000005152 nicotinamide Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
238000007670 refining Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000021055 solid food Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000002123 temporal effect Effects 0.000 description 1
230000004102 tricarboxylic acid cycle Effects 0.000 description 1
150000003628 tricarboxylic acids Chemical class 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP58235622A 1983-12-13 1983-12-13 ４・４’−ジエトオキシブチルアミンの脂肪族カルボン酸塩およびその製造方法 Granted JPS60126252A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP58235622A JPS60126252A (ja)	1983-12-13	1983-12-13	４・４’−ジエトオキシブチルアミンの脂肪族カルボン酸塩およびその製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP58235622A JPS60126252A (ja)	1983-12-13	1983-12-13	４・４’−ジエトオキシブチルアミンの脂肪族カルボン酸塩およびその製造方法

Publications (2)

Publication Number	Publication Date
JPS60126252A JPS60126252A (ja)	1985-07-05
JPS632949B2 true JPS632949B2 (da)	1988-01-21

Family

ID=16988734

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58235622A Granted JPS60126252A (ja)	1983-12-13	1983-12-13	４・４’−ジエトオキシブチルアミンの脂肪族カルボン酸塩およびその製造方法

Country Status (1)

Country	Link
JP (1)	JPS60126252A (da)

1983
- 1983-12-13 JP JP58235622A patent/JPS60126252A/ja active Granted

Also Published As

Publication number	Publication date
JPS60126252A (ja)	1985-07-05

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