JPS63135370A - Antiallergic agent - Google Patents
Antiallergic agentInfo
- Publication number
- JPS63135370A JPS63135370A JP27978486A JP27978486A JPS63135370A JP S63135370 A JPS63135370 A JP S63135370A JP 27978486 A JP27978486 A JP 27978486A JP 27978486 A JP27978486 A JP 27978486A JP S63135370 A JPS63135370 A JP S63135370A
- Authority
- JP
- Japan
- Prior art keywords
- antiallergic
- acid
- salt
- action
- hydroxyphenyl
- Prior art date
- 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.)
- Pending
Links
- 239000000043 antiallergic agent Substances 0.000 title claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- UYNVMODNBIQBMV-UHFFFAOYSA-N 4-[1-hydroxy-2-[4-(phenylmethyl)-1-piperidinyl]propyl]phenol Chemical compound C1CC(CC=2C=CC=CC=2)CCN1C(C)C(O)C1=CC=C(O)C=C1 UYNVMODNBIQBMV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 230000003266 anti-allergic effect Effects 0.000 abstract description 9
- 208000024891 symptom Diseases 0.000 abstract description 5
- 230000009471 action Effects 0.000 abstract description 4
- 208000026935 allergic disease Diseases 0.000 abstract description 3
- 239000000739 antihistaminic agent Substances 0.000 abstract description 3
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 abstract description 2
- 208000019901 Anxiety disease Diseases 0.000 abstract description 2
- 206010008111 Cerebral haemorrhage Diseases 0.000 abstract description 2
- 206010019233 Headaches Diseases 0.000 abstract description 2
- 241000282414 Homo sapiens Species 0.000 abstract description 2
- 206010039085 Rhinitis allergic Diseases 0.000 abstract description 2
- 201000010105 allergic rhinitis Diseases 0.000 abstract description 2
- 230000036506 anxiety Effects 0.000 abstract description 2
- 208000006673 asthma Diseases 0.000 abstract description 2
- 230000002213 calciumantagonistic effect Effects 0.000 abstract description 2
- 231100000869 headache Toxicity 0.000 abstract description 2
- 230000006872 improvement Effects 0.000 abstract description 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 abstract description 2
- 208000024780 Urticaria Diseases 0.000 abstract 1
- 208000012886 Vertigo Diseases 0.000 abstract 1
- 229940125715 antihistaminic agent Drugs 0.000 abstract 1
- 239000003218 coronary vasodilator agent Substances 0.000 abstract 1
- 231100000889 vertigo Toxicity 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 13
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 229940079593 drug Drugs 0.000 description 12
- 238000000034 method Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229960001340 histamine Drugs 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 229940095064 tartrate Drugs 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 241000282412 Homo Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 210000003405 ileum Anatomy 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010062717 Increased upper airway secretion 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
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 201000005505 Measles Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 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
- 210000001015 abdomen Anatomy 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 230000000794 anti-serotonin Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- -1 fatty acid esters Chemical class 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
イ０発明の目的
本発明は２−（４−ベンジルピペリジノ）−１−（４−
ヒドロキシフエニル）プロパン−１−オールまたはその
塩を含有する抗アレルギー剤に関する。DETAILED DESCRIPTION OF THE INVENTION A. Objects of the Invention The present invention relates to 2-(4-benzylpiperidino)-1-(4-
The present invention relates to an antiallergic agent containing hydroxyphenyl)propan-1-ol or a salt thereof.
従来、アレルギーの発現に関しては種々の機構によって
説明され抗アレルギー剤もそれに応じた種々の作用機序
のものが開発されてきた。例えば抗体ないし感作リンパ
球産生までの過程を抑制する薬剤で通常、免疫抑制剤と
呼ばれるもの、抗原から化学伝達物質までのあいだに作
用する薬剤などがあげられる。Conventionally, the expression of allergy has been explained by various mechanisms, and antiallergic agents with various mechanisms of action have been developed accordingly. Examples include drugs that suppress the process up to the production of antibodies or sensitized lymphocytes, which are usually called immunosuppressants, and drugs that act between antigens and chemical mediators.
そして、抗アレルギー作用の確認方法においては、一般
にヒスタミンやセロトニンなどに対する抑制、ＰＣ＆（
受身皮膚アナフィラキシ−反応）などが観察されている
。In general, methods for confirming anti-allergic effects include suppression of histamine and serotonin, PC&(
Passive cutaneous anaphylactic reactions have been observed.
近年、大気汚染、化学物質などによるアレルギーの問題
に鑑み、新規な抗アレルギー剤だ対する要望は社会的に
極めて大きなものである。In recent years, in view of the problems of allergies caused by air pollution, chemical substances, etc., there has been an extremely large social demand for new anti-allergic agents.
本発明薬剤に含有される２−（４−ベンジルピペリジノ
）−１−（４−ヒドロキシフエニル）プロパン−１−オ
ールの酒石酸塩は脳出血後遺症に併なう、めまい、頭痛
、抑うつ、不安、興奮などの症状改善の効能を有する化
合物として知られており〔買弁ら、薬理と治療、第５巻
第１０号第３１０７頁（１９７７年）〕、また、他の薬
理作用としてカルシウム拮抗作用、冠血管拡張作用（特
開昭６１−１７２８２０号及び特開昭６１−１８６３１
１号公報）が見い出されているが、抗アレルギー作用に
ついては何ら知られていない。The tartrate of 2-(4-benzylpiperidino)-1-(4-hydroxyphenyl)propan-1-ol contained in the drug of the present invention may cause dizziness, headache, depression, and anxiety associated with cerebral hemorrhage sequelae. It is known as a compound that has the efficacy of improving symptoms such as excitement [Kabane et al., Pharmacology and Treatment, Vol. 5, No. 10, p. 3107 (1977)], and has other pharmacological actions such as calcium antagonistic action Coronary vasodilation effect (JP-A-61-172820 and JP-A-61-18631)
1), but nothing is known about its anti-allergic effect.
ロ０発明の構成
今回、本発明者らは鋭意研究を行なった結果、本発明を
完成させるに到りた。すなわち、本発明は２−（４−ベ
ルジルピペリジノ）−１−（４−ヒドロキシフエニル）
フロノくノー１−オールまたはその塩を有効成分として
含有する抗アレルギー作用に関する。本発明における上
記化合物のような骨格を有するものが抗アレルギー作用
を有することは未だ知られていない。B0 Structure of the Invention As a result of intensive research, the present inventors have completed the present invention. That is, the present invention provides 2-(4-berzylpiperidino)-1-(4-hydroxyphenyl)
The present invention relates to an anti-allergic effect containing furono-1-ol or a salt thereof as an active ingredient. It is not yet known that compounds having a skeleton like the above-mentioned compounds in the present invention have antiallergic effects.
本発明薬剤の２−（４−ベンジルピペリジノ）−１−（
４−ヒドロキシフエニル）ブロック／−１−オールは、
下記構造を有する化合物〔以下、化合物（Ｉ）と略称す
ることもある〕である。化合物（Ｉ）は、立体化
（Ｌ）
学的にエリスＯ（ｅｒｙｔｈｒｏ）体とスレオ（ｔｈｒ
ｅｏ）体とを包含するが、通常はエリスロ体＋中テ〒′
１村、−一ムーーーーー亭の方が好ましく使用される。2-(4-benzylpiperidino)-1-( of the drug of the present invention
4-hydroxyphenyl) block/-1-ol is
It is a compound (hereinafter sometimes abbreviated as compound (I)) having the following structure. Compound (I) has three-dimensional (L) chemically erythro (erythro) form and threo (thr) form.
eo) body, but usually includes erythro body + middle te
1 village, -1 mu--tei are more preferably used.
・６゛ｈ化合物（Ｉ）の塩としては、有機酸ないし
無機°′酸の塩が挙げられる。かかる有機酸の塩として
゛は、酒石酸、乳酸、酢酸、リンゴ酸、クエン酸、７
マール酸、マレイン酸、コ／・り酸、ノくルミチン酸、
ステアリン酸、オレイン酸、リノール酸、リルン酸など
の脂肪族カルボン酸の塩；トシル酸、メシル酸、ナプシ
ル酸などのスルホン酸の塩が例示され、また無機酸の塩
としては、塩酸、臭化水素酸、リン酸、硫飯などの無機
鉱酸の塩が代表的である。・Salts of 6゛h compound (I) include salts of organic acids or inorganic acids. Salts of such organic acids include tartaric acid, lactic acid, acetic acid, malic acid, citric acid,
Maric acid, maleic acid, co/・phosphoric acid, noclumitic acid,
Examples include salts of aliphatic carboxylic acids such as stearic acid, oleic acid, linoleic acid, and linolic acid; salts of sulfonic acids such as tosylic acid, mesylic acid, and napsylic acid; and salts of inorganic acids such as hydrochloric acid and brominated acid. Typical examples include salts of inorganic mineral acids such as hydrogen acid, phosphoric acid, and sulfuric acid.
本発明薬剤は、化合物（Ｉ）またはその塩をそのまま用
いてもよいが、通常は薬理学的、製剤学的に許容される
添加物を加えて使用するのが良い。当該添加物を用いる
場合、本発明薬剤中の化合物（Ｉ）の配合量は通常は０
．１〜１０重量係、好ましくは０．２〜５重−１ｑｂで
ある。Although compound (I) or a salt thereof may be used as it is in the drug of the present invention, it is usually preferable to use it with pharmacologically and pharmaceutically acceptable additives added thereto. When using the additive, the amount of compound (I) in the drug of the present invention is usually 0.
．． It is 1 to 10 weight, preferably 0.2 to 5 weight - 1 qb.
上記添加物としては、内服用製剤（経口剤）、注射用製
剤（注射剤）、粘膜投与剤（バッカル、トローチ、層剤
等）、外用剤（軟膏、貼付剤等）などの投与経路に応じ
た適当な製剤用成分から使用される。例えば、経口剤お
よび粘膜投与剤にあっては、賦形剤（例：でんぷん、乳
糖）、崩壊剤（例：カルボキシメチルセルロース）、滑
沢剤（例ニステアリン酸マグネシウム）、コーチインク
剤（例：ヒドロキシエチルセルロース）、矯味剤などの
製剤用成分が、また注射剤にあっては、水性注射剤を構
成し得る溶解剤ないし溶解補助剤（例：注射用蒸留水、
生理食塩水、プロピレングリコール）、懸濁化剤（例：
ポリソルベート８０などの界面活性剤）、ｐＨ調整剤（
例：有機酸またはその金属塩）、安定化剤などの製剤用
成分が、さらに外用剤にあっては、水性ないし油性の溶
解剤ないし溶解補助剤（例：アルコール、脂肪酸エステ
ル類）、粘着剤（例：カルボキシビニルポリマー、多糖
類）、乳化剤（例：界面活性剤）などの製剤用成分が使
用される。以上の製剤用成分については、公知のもの〔
例えば、Ａ、 Ｏ，Ｃｈａ ｌ ｒｍａｎら編、ｒＲｅ
−ｍｉｎｇｔｏｎ’ ｓ Ｐｈａｒｍａｃｅｕｔｉｃａ
ｌ ５ｃｉｅｎｃｅＪ １９８０年版、Ｍａｃｋ Ｐｕ
ｂｌｉｓｈｉｎｇ Ｃｏ、発行（米国）に記載の製剤成
分〕を便宜に採用することができる。The above additives are used depending on the route of administration, such as internal preparations (oral preparations), injection preparations (injection preparations), mucosal preparations (buccal, trochees, layered preparations, etc.), and external preparations (ointments, patches, etc.). It is used from suitable formulation ingredients. For example, for oral preparations and mucosal administration preparations, excipients (e.g. starch, lactose), disintegrants (e.g. carboxymethylcellulose), lubricants (e.g. magnesium nistearate), coach inks (e.g. In the case of injections, solubilizers or solubilizers (e.g. distilled water for injection,
saline, propylene glycol), suspending agents (e.g.
surfactants such as polysorbate 80), pH adjusters (
For external preparations, formulation ingredients such as organic acids or their metal salts), stabilizers, and aqueous or oil-based solubilizers or solubilizers (e.g., alcohol, fatty acid esters), adhesives, etc. (e.g., carboxyvinyl polymers, polysaccharides), emulsifiers (e.g., surfactants), and other formulation ingredients are used. The above formulation ingredients are publicly known [
For example, A. O. Challman et al., eds. rRe
-mington's Pharmaceutica
l 5scienceJ 1980 edition, Mack Pu
Blishing Co., Publication (USA)] can be conveniently employed.
上記構成を有する本発明薬剤は、公知の製造法、例えば
日本薬局方第１０版（日周Ｘ）製剤総則記載の方法ない
し適当なモディフィケーシヨンを加えた方法によって製
造することができる。The drug of the present invention having the above-mentioned structure can be manufactured by a known manufacturing method, for example, the method described in the Japanese Pharmacopoeia, 10th edition (Diurnal X) General Rules for Preparations, or a method with appropriate modifications.
化合物（Ｉ）およびその塩は、ヒト、サル、イヌ、ネコ
、ウサギ、ラット、マウスなどの哺乳動物に対して抗ア
レルギー作用を有するので、本発明薬剤はヒトの気管支
喘息、アレルギー性鼻炎、じん麻疹、枯草熱などの種々
のアレルギー性疾患に対して、その症状改善ないし予防
、治療の目的で使用することができる。この際、化合物
（Ｉ）ないしその塩または前述の添加物を加え製剤化し
たものを、経口的ないし非経口的に使用できる。Compound (I) and its salts have antiallergic effects on mammals such as humans, monkeys, dogs, cats, rabbits, rats, and mice, so the drug of the present invention can be used to treat bronchial asthma, allergic rhinitis, and phlegm in humans. It can be used for symptom improvement, prevention, and treatment of various allergic diseases such as measles and hay fever. In this case, compound (I) or a salt thereof, or a formulation prepared by adding the above-mentioned additives, can be used orally or parenterally.
上記における本発明薬剤のヒト成人に対する投与量は、
化合物（Ｉ）またはその塩の童に換算して、経口剤、外
用剤にあっては、１０〜１５０１ＨＩ／１日を１日２〜
４回に分版するのがよく、また注射剤、粘膜投与剤にあ
っては、上記投与量の１／２〜１／１０量で充分なこと
が多い。しかし、対象疾患の種類と症状、患者の年令、
性別などてよって適宜増減して投与するのが望ましい。The above dosage of the drug of the present invention for adult human beings is as follows:
For oral preparations and external preparations of Compound (I) or its salt, the dosage is 10 to 1501 HI/day for 2 to 2 days.
It is preferable to divide into 4 times, and in the case of injections and mucosal administration agents, 1/2 to 1/10 of the above-mentioned dose is often sufficient. However, the type and symptoms of the target disease, the age of the patient,
It is desirable to increase or decrease the dose as appropriate depending on gender, etc.
次に、本発明薬剤の化合物（Ｉ）の抗アレルギー作用に
関する薬理試験例を示す。Next, pharmacological test examples regarding the antiallergic effect of compound (I) of the drug of the present invention will be shown.
試験例１ ラットのＰＣＡ阻害効果
〔方法〕
抗卵白アルブミン血清（ＩｇＥ）を腹部皮下に注射して
感作したラットに検体（酒石酸イアエンプロジル）を経
口投与した。その１５分後に卵白アルブミン血清とエバ
ンスブルーの混液を静脈内投与して、ＰＣＡ反応を誘発
した。抗アレルギー効果の判定にあたっては、ＰＣＡ反
応のブルースポットにおいて５０１以上抑制を以って効
果と判定した。Test Example 1 PCA inhibitory effect in rats [Method] A specimen (iaenprodil tartrate) was orally administered to rats that had been sensitized by subcutaneously injecting anti-ovalbumin serum (IgE) into the abdomen. Fifteen minutes later, a mixture of ovalbumin serum and Evans blue was administered intravenously to induce a PCA reaction. In determining the antiallergic effect, an inhibition of 501 or more in blue spots of PCA reaction was judged to be effective.
検体の投与ｆＩｔ（ＷＶ１Ｃ９） 抑制作用（チ
）試験例２ ヒスタミンＨ□抑制作用〔方法〕
ラットに検体（酒石酸イアエンプロジル）を経口投与し
たのち、ヒスタミン（３０ｍｃｇ７０．０５ｍ）を皮肉
に注射し、注射の１０分後に屠殺した。ヒスタミンによ
り惹起される腫脹の５０１以上の抑制を以って、ヒスタ
ミンのＨ□−抑制効果と判定した。Administration of specimen fIt (WV1C9) Inhibitory effect (H) Test example 2 Histamine H□ inhibitory effect [Method] After orally administering the specimen (iaenprodil tartrate) to rats, histamine (30 mcg 70.05 m) was injected ironically. Animals were sacrificed 10 minutes after injection. Suppression of histamine-induced swelling of 501 or more was determined to be an H□-suppressing effect of histamine.
試験例３ 抗ヒスタミン作用 （Ｉｎ Ｖｉｔｒｏ
）〔方法〕
検体（酒石酸イアエンプロジル）投与時におけるモルモ
ット摘出回腸のヒスタミン（０，５ｍｅ ｇ／ｍｌ ）
による収縮に対する抑制を調べた。Test Example 3 Antihistamine effect (In Vitro
) [Method] Histamine (0.5 meg/ml) in isolated guinea pig ileum at the time of administration of sample (iaenprodil tartrate)
We investigated the inhibition of contraction caused by
検体の投与ｉｔ （ｍｅ ｇ ） 抑制作用５．
０＋
２．５＋
１、Ｏ＋
０．５−
試験例４ 抗セロトニン作用 （Ｉｎ Ｖｉｔｒｏ
）Ｃ方法〕
検体（酒石酸イ７エングロジル）投与時におけるモルロ
ットの摘出回腸のセロトニン（１ｍｃｇ／ｄ）による収
縮に対する抑制を調べた。Administration of specimen it (meg) Suppressive effect 5.
0+ 2.5+ 1, O+ 0.5- Test Example 4 Anti-serotonin effect (In Vitro
) Method C] The suppression of contraction of the isolated ileum of morlots by serotonin (1 mcg/d) during administration of the sample (i7engrodil tartrate) was investigated.
５．０＋
２．５−
ハ６発明の効果
以上から発明の効果は明らかである。すなわち１本発明
によつて抗アレルギー作用、殊に抗ヒスタミン作用を有
し、医療上有用な価値を有する薬剤が提供され、本発明
薬剤は産業上有用なものである。5.0+ 2.5- C6 Effects of the invention From the above, the effects of the invention are clear. That is, the present invention provides a drug that has antiallergic action, especially antihistamine action, and has medically useful value, and the drug of the present invention is industrially useful.
Claims (1)
シフエニル）プロパン−１−オールまたはその塩を有効
成分とする抗アレルギー剤Antiallergic agent containing 2-(4-benzylpiperidino)-1-(4-hydroxyphenyl)propan-1-ol or its salt as an active ingredient
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27978486A JPS63135370A (en) | 1986-11-26 | 1986-11-26 | Antiallergic agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27978486A JPS63135370A (en) | 1986-11-26 | 1986-11-26 | Antiallergic agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63135370A true JPS63135370A (en) | 1988-06-07 |
Family
ID=17615867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27978486A Pending JPS63135370A (en) | 1986-11-26 | 1986-11-26 | Antiallergic agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63135370A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5289244A (en) * | 1990-10-16 | 1994-02-22 | Asahi Kogaku Kogyo Kabushiki Kaisha | Wrinkle prevention structure for electrophotographic printer |
| EP0804181A4 (en) * | 1995-09-19 | 2005-02-02 | Cellular Sciences Inc | Method and composition for treating mammalian diseases caused by inflammatory response |
-
1986
- 1986-11-26 JP JP27978486A patent/JPS63135370A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5289244A (en) * | 1990-10-16 | 1994-02-22 | Asahi Kogaku Kogyo Kabushiki Kaisha | Wrinkle prevention structure for electrophotographic printer |
| EP0804181A4 (en) * | 1995-09-19 | 2005-02-02 | Cellular Sciences Inc | Method and composition for treating mammalian diseases caused by inflammatory response |
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