JPH0148259B2 - - Google Patents

Info

Publication number: JPH0148259B2
Authority: JP; Japan
Prior art keywords: multiplet; formula; piperidinylmethyl; cis; phenoxy
Prior art date: 1981-04-06
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

JP56050535A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57165348A (en

Inventor

Takeo Shibata

Toshihisa Itaya

Nobuaki Yamagoshi

Shigeru Kurata

Naoyuki Koizumi

Masao Taruya

Hideki Sakuma

Kunihiro Konishi

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.)

Aska Pharmaceutical Co Ltd

Original Assignee

Teikoku Hormone Manufacturing 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.)

1981-04-06

Filing date

1981-04-06

Publication date

1989-10-18

1981-04-06 Application filed by Teikoku Hormone Manufacturing Co Ltd filed Critical Teikoku Hormone Manufacturing Co Ltd

1981-04-06 Priority to JP56050535A priority Critical patent/JPS57165348A/ja

1982-10-12 Publication of JPS57165348A publication Critical patent/JPS57165348A/ja

1989-10-18 Publication of JPH0148259B2 publication Critical patent/JPH0148259B2/ja

Status Granted legal-status Critical Current

Links

-1 perhydroazepinyl group Chemical group 0.000 claims description 87
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 102
150000001875 compounds Chemical class 0.000 description 100
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 65
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
239000003921 oil Substances 0.000 description 48
238000000034 method Methods 0.000 description 45
239000007788 liquid Substances 0.000 description 43
239000002904 solvent Substances 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
238000004519 manufacturing process Methods 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 30
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 26
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 20
238000005406 washing Methods 0.000 description 20
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 19
238000003756 stirring Methods 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
235000002639 sodium chloride Nutrition 0.000 description 17
239000000243 solution Substances 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
229960001340 histamine Drugs 0.000 description 13
238000010992 reflux Methods 0.000 description 13
238000004809 thin layer chromatography Methods 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000005457 ice water Substances 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 11
238000001816 cooling Methods 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
238000007112 amidation reaction Methods 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
239000002775 capsule Substances 0.000 description 7
238000001035 drying Methods 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 6
ASVKKRLMJCWVQF-UHFFFAOYSA-N 3-buten-1-amine Chemical compound NCCC=C ASVKKRLMJCWVQF-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
231100000673 dose–response relationship Toxicity 0.000 description 5
239000003814 drug Substances 0.000 description 5
230000027119 gastric acid secretion Effects 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
QFUSOYKIDBRREL-NSCUHMNNSA-N (e)-but-2-en-1-amine Chemical compound C\C=C\CN QFUSOYKIDBRREL-NSCUHMNNSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
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 4
241001465754 Metazoa Species 0.000 description 4
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 4
230000009435 amidation Effects 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
230000008485 antagonism Effects 0.000 description 4
239000003699 antiulcer agent Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000002148 esters Chemical group 0.000 description 4
210000004211 gastric acid Anatomy 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000008101 lactose Substances 0.000 description 4
239000010446 mirabilite Substances 0.000 description 4
229910052698 phosphorus Inorganic materials 0.000 description 4
239000011574 phosphorus Substances 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
DMLYTGPBYWHKHU-UHFFFAOYSA-N (2-amino-2-oxoethyl) acetate Chemical compound CC(=O)OCC(N)=O DMLYTGPBYWHKHU-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000010908 decantation Methods 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
SZOLUXDHHKCYKT-ONEGZZNKSA-N (e)-but-1-en-1-amine Chemical compound CC\C=C\N SZOLUXDHHKCYKT-ONEGZZNKSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
FTKQHXNOTYHHLE-UHFFFAOYSA-N 2-(piperidin-1-ium-1-ylmethyl)phenolate Chemical compound OC1=CC=CC=C1CN1CCCCC1 FTKQHXNOTYHHLE-UHFFFAOYSA-N 0.000 description 2
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
UJDTVJKIOWAUNQ-UHFFFAOYSA-N 3-(piperidin-1-ylmethyl)benzaldehyde Chemical compound O=CC1=CC=CC(CN2CCCCC2)=C1 UJDTVJKIOWAUNQ-UHFFFAOYSA-N 0.000 description 2
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
238000007239 Wittig reaction Methods 0.000 description 2
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 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000001078 anti-cholinergic effect Effects 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
235000015165 citric acid Nutrition 0.000 description 2
238000003745 diagnosis Methods 0.000 description 2
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
210000001198 duodenum Anatomy 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
210000002837 heart atrium Anatomy 0.000 description 2
238000006698 hydrazinolysis reaction Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
229940031826 phenolate Drugs 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
230000004044 response Effects 0.000 description 2
210000005245 right atrium Anatomy 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
231100000397 ulcer Toxicity 0.000 description 2
HBEWADIWKZVJSD-UHFFFAOYSA-N (2-amino-2-oxoethyl) benzoate Chemical compound NC(=O)COC(=O)C1=CC=CC=C1 HBEWADIWKZVJSD-UHFFFAOYSA-N 0.000 description 1
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
FQDIANVAWVHZIR-UPHRSURJSA-N (z)-1,4-dichlorobut-2-ene Chemical compound ClC\C=C/CCl FQDIANVAWVHZIR-UPHRSURJSA-N 0.000 description 1
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
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Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Indole Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyridine Compounds (AREA)
Pyrrole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP56050535A 1981-04-06 1981-04-06 Novel aminoalkylbenzene derivative Granted JPS57165348A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP56050535A JPS57165348A (en)	1981-04-06	1981-04-06	Novel aminoalkylbenzene derivative

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP56050535A JPS57165348A (en)	1981-04-06	1981-04-06	Novel aminoalkylbenzene derivative

Related Child Applications (2)

Application Number	Title	Priority Date	Filing Date
JP1016480A Division JPH02178A (ja)	1989-01-27	1989-01-27	新規なアミノアルキルベンゼン誘導体
JP1101587A Division JPH0256449A (ja)	1989-04-24	1989-04-24	アミノアルキルベンゼン誘導体

Publications (2)

Publication Number	Publication Date
JPS57165348A JPS57165348A (en)	1982-10-12
JPH0148259B2 true JPH0148259B2 (fr)	1989-10-18

Family

ID=12861689

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP56050535A Granted JPS57165348A (en)	1981-04-06	1981-04-06	Novel aminoalkylbenzene derivative

Country Status (1)

Country	Link
JP (1)	JPS57165348A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60255756A (ja) *	1984-06-01	1985-12-17	Ikeda Mohandou:Kk	アミノアルキルフエノキシ誘導体
AU662454B2 (en) *	1992-05-12	1995-08-31	Zeria Pharmaceutical Co., Ltd.	Novel quaternary ammonium salts and use thereof as medicine
WO2013036766A1 (fr) *	2011-09-09	2013-03-14	University Of Georgia Research Foundation, Inc.	Lipocations à base de naphtoquinone et de phtalimide à petites molécules en tant qu'agents anti-parasitaires
EP4196793A1 (fr)	2020-08-11	2023-06-21	Université de Strasbourg	Bloqueurs de h2 ciblant des macrophages du foie pour la prévention et le traitement d'une maladie du foie et du cancer

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS53149936A (en) *	1977-05-17	1978-12-27	Allen & Hanburys Ltd	Novel aminoalkylbenzene derivative process for preparing same medical composition and application thereof
JPS5553247A (en) *	1978-10-17	1980-04-18	Shionogi & Co Ltd	Novel benzylamine derivative

1981
- 1981-04-06 JP JP56050535A patent/JPS57165348A/ja active Granted

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS53149936A (en) *	1977-05-17	1978-12-27	Allen & Hanburys Ltd	Novel aminoalkylbenzene derivative process for preparing same medical composition and application thereof
JPS5553247A (en) *	1978-10-17	1980-04-18	Shionogi & Co Ltd	Novel benzylamine derivative

Also Published As

Publication number	Publication date
JPS57165348A (en)	1982-10-12

Publication	Publication Date	Title
EP0024510B1 (fr)	1983-10-19	Dérivés de la phénoxypropylamine, procédé pour leur préparation, et compositions pharmaceutiques les contenant
JPH05502452A (ja)	1993-04-28	チロシンキナーゼ阻害剤としてのベンジルホスホン酸
JP3419009B2 (ja)	2003-06-23	縮合ベンゼンオキシ酢酸誘導体およびそれらを有効成分として含有する薬剤
US20080227858A1 (en)	2008-09-18	Inhibitors of matrix metalloproteinase
JPH0559119B2 (fr)	1993-08-30
JPS6160074B2 (fr)	1986-12-19
JPH0148259B2 (fr)	1989-10-18
KR20120007566A (ko)	2012-01-20	기질 금속단백분해효소 억제제
JPS58164577A (ja)	1983-09-29	４―ベンジル―１―（２ｈ）イソキノロン誘導体
JPH09328469A (ja)	1997-12-22	新規置換アセトアミド化合物
AU610218B2 (en)	1991-05-16	Improvements in or relating to leukotriene antagonists
JP3077295B2 (ja)	2000-08-14	チアゾール化合物
JPH08188546A (ja)	1996-07-23	カルコン誘導体
JPH0428695B2 (fr)	1992-05-15
JPH0558997A (ja)	1993-03-09	チオカルバモイルアセトニトリル誘導体
US4820722A (en)	1989-04-11	Disubstituted tetrazoles and their use as leukotriene antagonists
JPH0380791B2 (fr)	1991-12-26
JPH0250112B2 (fr)	1990-11-01
JPH0436156B2 (fr)	1992-06-15
JPH10512595A (ja)	1998-12-02	３−（１−ピペラジニル）−１，２−ベンズイソチアゾールを調製するための方法および中間物質
JPH0340025B2 (fr)	1991-06-17
JPH0141615B2 (fr)	1989-09-06
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JPH11292879A (ja)	1999-10-26	カルボキサミド誘導体
JPS6148821B2 (fr)	1986-10-25