JPS63126823A - 抗潰瘍治療薬 - Google Patents

抗潰瘍治療薬

Info

Publication number: JPS63126823A
Authority: JP; Japan
Prior art keywords: ulcer; methyl; tetrahydroisoquinoline; compound; chloroform
Prior art date: 1986-10-23
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

Application number

JP26801287A

Other languages

English (en)

Japanese (ja)

Inventor

チャブダル・ボリソフ・イワノフ

ネドヤルカ・ストヤノバ・イワノバ

ブラディミル・デイミトロフ・パスコフ

リリアナ・デイミトロバ・ダレバ

デイアナ・ミンコバ・モンデシュカ

ニコリナ・デイミトロバ・ベロバ

ロッシツア・ステファノバ・ラコブスカ

ドンカ・ニコロバ・トシェバ

ヒリスト・ヤンツェフ・ザイコフ

ヨシフ・ニッシム・ニッシモフ

ベッセリン・リュボミロフ・オラチェフ

ルミアナ・ニコロバ・ナチェバ

チョンカ・ネストロバ・タンチェバ

イワンカ・ゲオルギエバ・アンゲロバ

ステファン・エミロフ・ボヤジエフ

グリゴル・ミンチェフ・メクコフ

ボリス・クルモフ・デイミトロフ

ブラデイミル・コンスタンテイノフ・マトフ

ズラブコ・デイミトロフ・ゲンジェフ

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.)

Pharmachim DSO

Original Assignee

Pharmachim DSO

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.)

1986-10-23

Filing date

1987-10-23

Publication date

1988-05-30

1987-10-23 Application filed by Pharmachim DSO filed Critical Pharmachim DSO

1988-05-30 Publication of JPS63126823A publication Critical patent/JPS63126823A/ja

Status Pending legal-status Critical Current

Links

230000000259 anti-tumor effect Effects 0.000 title 1
229910052736 halogen Inorganic materials 0.000 claims description 4
125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
230000000694 effects Effects 0.000 description 28
230000000767 anti-ulcer Effects 0.000 description 25
208000025865 Ulcer Diseases 0.000 description 22
231100000397 ulcer Toxicity 0.000 description 22
150000001875 compounds Chemical class 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
229960000620 ranitidine Drugs 0.000 description 17
VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000012458 free base Substances 0.000 description 13
241001465754 Metazoa Species 0.000 description 11
241000700159 Rattus Species 0.000 description 10
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
229960001380 cimetidine Drugs 0.000 description 9
CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 9
239000003814 drug Substances 0.000 description 9
208000000718 duodenal ulcer Diseases 0.000 description 9
230000005764 inhibitory process Effects 0.000 description 9
229940049920 malate Drugs 0.000 description 9
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
230000002378 acidificating effect Effects 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
239000011975 tartaric acid Substances 0.000 description 8
206010042220 Stress ulcer Diseases 0.000 description 7
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229940095064 tartrate Drugs 0.000 description 6
238000012360 testing method Methods 0.000 description 6
VOZWXKYLVQXXCK-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinolin-8-amine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=C(Cl)C=C1 VOZWXKYLVQXXCK-UHFFFAOYSA-N 0.000 description 5
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
229940125890 compound Ia Drugs 0.000 description 5
229940079593 drug Drugs 0.000 description 5
229960000905 indomethacin Drugs 0.000 description 5
GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 4
PJIBWJPNKNAWGQ-UHFFFAOYSA-N 8-chloro-2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(Cl)=C2CN(C)CC1C1=CC=CC=C1 PJIBWJPNKNAWGQ-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
241000700157 Rattus norvegicus Species 0.000 description 4
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 4
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-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
230000000052 comparative effect Effects 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
230000001066 destructive effect Effects 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 4
229960003147 reserpine Drugs 0.000 description 4
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
210000002784 stomach Anatomy 0.000 description 4
230000035882 stress Effects 0.000 description 4
230000001629 suppression Effects 0.000 description 4
102000003710 Histamine H2 Receptors Human genes 0.000 description 3
108090000050 Histamine H2 Receptors Proteins 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
210000004051 gastric juice Anatomy 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
230000028327 secretion Effects 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
-1 aminochlorobenzyl methylamine Chemical compound 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
FQPXAXLGKPKAMF-UHFFFAOYSA-N ethyl n-(2-methyl-4-phenyl-3,4-dihydro-1h-isoquinolin-8-yl)carbamate Chemical compound C1N(C)CC=2C(NC(=O)OCC)=CC=CC=2C1C1=CC=CC=C1 FQPXAXLGKPKAMF-UHFFFAOYSA-N 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
230000009291 secondary effect Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
DIWGZVQKFSFNLH-UHFFFAOYSA-N 1-(2-chlorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=CC=C1Cl DIWGZVQKFSFNLH-UHFFFAOYSA-N 0.000 description 1
BRFNMGAFJUYWRU-UHFFFAOYSA-N 1-[(2-chlorophenyl)methylamino]-1-phenylpropan-1-ol Chemical compound ClC1=C(CNC(CC)(O)C2=CC=CC=C2)C=CC=C1 BRFNMGAFJUYWRU-UHFFFAOYSA-N 0.000 description 1
VEUVRHMVUVVBFC-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl-methylamino]-1-phenylethanol Chemical compound C=1C=CC=C(Cl)C=1CN(C)CC(O)C1=CC=CC=C1 VEUVRHMVUVVBFC-UHFFFAOYSA-N 0.000 description 1
HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
201000010000 Agranulocytosis Diseases 0.000 description 1
206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
206010018687 Granulocytopenia Diseases 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
108010079943 Pentagastrin Proteins 0.000 description 1
208000007107 Stomach Ulcer Diseases 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
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000006598 aminocarbonylamino group Chemical group 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
239000003699 antiulcer agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000036471 bradycardia Effects 0.000 description 1
208000006218 bradycardia Diseases 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
230000007012 clinical effect Effects 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000002183 duodenal effect Effects 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
230000002857 effect on ulcer Effects 0.000 description 1
230000003628 erosive effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000003721 gunpowder Substances 0.000 description 1
208000006454 hepatitis Diseases 0.000 description 1
231100000283 hepatitis Toxicity 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
JFOZKMSJYSPYLN-QHCPKHFHSA-N lifitegrast Chemical compound CS(=O)(=O)C1=CC=CC(C[C@H](NC(=O)C=2C(=C3CCN(CC3=CC=2Cl)C(=O)C=2C=C3OC=CC3=CC=2)Cl)C(O)=O)=C1 JFOZKMSJYSPYLN-QHCPKHFHSA-N 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
231100000324 minimal toxicity Toxicity 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
XXPANQJNYNUNES-UHFFFAOYSA-N nomifensine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=CC=C1 XXPANQJNYNUNES-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
229960000444 pentagastrin Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

JP26801287A 1986-10-23 1987-10-23 抗潰瘍治療薬 Pending JPS63126823A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
BG76843		1986-10-23
BG7684386A BG45572A1 (en)	1986-10-23	1986-10-23	Antiulcer means

Publications (1)

Publication Number	Publication Date
JPS63126823A true JPS63126823A (ja)	1988-05-30

Family

ID=3917941

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP26801287A Pending JPS63126823A (ja)	1986-10-23	1987-10-23	抗潰瘍治療薬

Country Status (7)

Country	Link
JP (1)	JPS63126823A (da)
AU (1)	AU612989B2 (da)
BG (1)	BG45572A1 (da)
CA (1)	CA1309349C (da)
DK (1)	DK556587A (da)
FI (1)	FI874677A7 (da)
HU (1)	HU203474B (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MD3972C2 (ro) *	2009-03-11	2010-07-31	Ион МЕРЕУЦЭ	Remediu şi metodă de tratament al stărilor precanceroase

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS543078A (en) *	1977-06-01	1979-01-11	Hoechst Ag	44phenyll88aminoo tetrahydroisoquinoline compound
JPS545045A (en) *	1977-06-01	1979-01-16	Hoechst Ag	Pharmaceutical composition
JPS59176260A (ja) *	1983-03-25	1984-10-05	ヘキスト・アクチエンゲゼルシヤフト	８−アミノ−２−メチル−４−フエニル−１，２，３，４−テトラヒドロイソキノリンの光学対掌体
JPS615017A (ja) *	1984-04-13	1986-01-10	タルゴフスコ・プロイツボドストベノ・オベデイネニエ”フアルマチム”	抗潰瘍組成物

1986
- 1986-10-23 BG BG7684386A patent/BG45572A1/xx unknown
1987
- 1987-10-23 FI FI874677A patent/FI874677A7/fi not_active Application Discontinuation
- 1987-10-23 JP JP26801287A patent/JPS63126823A/ja active Pending
- 1987-10-23 CA CA000550075A patent/CA1309349C/en not_active Expired - Lifetime
- 1987-10-23 DK DK556587A patent/DK556587A/da not_active Application Discontinuation
- 1987-10-23 AU AU80119/87A patent/AU612989B2/en not_active Expired - Fee Related
- 1987-12-17 HU HU874727A patent/HU203474B/hu not_active IP Right Cessation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS543078A (en) *	1977-06-01	1979-01-11	Hoechst Ag	44phenyll88aminoo tetrahydroisoquinoline compound
JPS545045A (en) *	1977-06-01	1979-01-16	Hoechst Ag	Pharmaceutical composition
JPS59176260A (ja) *	1983-03-25	1984-10-05	ヘキスト・アクチエンゲゼルシヤフト	８−アミノ−２−メチル−４−フエニル−１，２，３，４−テトラヒドロイソキノリンの光学対掌体
JPS615017A (ja) *	1984-04-13	1986-01-10	タルゴフスコ・プロイツボドストベノ・オベデイネニエ”フアルマチム”	抗潰瘍組成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MD3972C2 (ro) *	2009-03-11	2010-07-31	Ион МЕРЕУЦЭ	Remediu şi metodă de tratament al stărilor precanceroase

Also Published As

Publication number	Publication date
FI874677A0 (fi)	1987-10-23
DK556587D0 (da)	1987-10-23
AU612989B2 (en)	1991-07-25
AU8011987A (en)	1988-04-28
HU203474B (en)	1991-08-28
FI874677A7 (fi)	1988-04-24
HUT44928A (en)	1988-05-30
BG45572A1 (en)	1989-07-14
DK556587A (da)	1988-04-24
CA1309349C (en)	1992-10-27

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JPS636058B2 (da)	1988-02-08
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JPS58188879A (ja)	1983-11-04	シプロヘプタジン−３−カルボン酸及び構造的に関連した化合物のエステル
KR960007752B1 (ko)	1996-06-12	심부전증 치료제
JPH0317078A (ja)	1991-01-25	８‐置換４‐（ヘテロサイクリルメチルアミノ）‐キノリン
FI61182C (fi)	1982-06-10	Foerfarande foer framstaellning av farmaceutiskt aktiva butylaminderivat
JP2800830B2 (ja)	1998-09-21	１，２，３，４−テトラヒドロイソキノリン抗不整脈薬
JPH05503525A (ja)	1993-06-10	インドール誘導体、その製造及び使用
JPS61500437A (ja)	1986-03-13	ｎ−プロパノ−ルアミン誘導体のエ−テル
US3959476A (en)	1976-05-25	Antihypertensive substituted triazoles
US6476020B1 (en)	2002-11-05	Imidazo-benzazepine compounds, their compositions and uses
CA3191714A1 (en)	2022-02-17	Benzylamine derivative, preparation method therefor and use thereof
CA1309349C (en)	1992-10-27	Anti-ulcer-remedy containing tetrahydroisoquinoline derivatives
US3903165A (en)	1975-09-02	Ethynylaryl amines and processes for their preparation
JPS62108863A (ja)	1987-05-20	２−ピリジル酢酸誘導体、その製法およびそれを含む医薬
US4042584A (en)	1977-08-16	Ethynylaryl phenyl cyclopropyl thiazines and morpholines
JPS5976083A (ja)	1984-04-28	ジヒドロピリジン類
US3760082A (en)	1973-09-18	Compositions containing 5-amino-3-ethyl-1-phenyl-4-pyrazolecarboxamides and methods of using the same
JPS63126860A (ja)	1988-05-30	グアニジノメチル安息香酸誘導体

JPS63126823A - 抗潰瘍治療薬 - Google Patents

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