JPH0339063B2 - - Google Patents
Info
- Publication number
- JPH0339063B2 JPH0339063B2 JP57109192A JP10919282A JPH0339063B2 JP H0339063 B2 JPH0339063 B2 JP H0339063B2 JP 57109192 A JP57109192 A JP 57109192A JP 10919282 A JP10919282 A JP 10919282A JP H0339063 B2 JPH0339063 B2 JP H0339063B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- compound
- present
- observed
- administered
- 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.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 claims description 5
- VUNXBQRNMNVUMV-UHFFFAOYSA-N phenyl(piperazin-1-yl)methanone Chemical class C=1C=CC=CC=1C(=O)N1CCNCC1 VUNXBQRNMNVUMV-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 7
- 108090000317 Chymotrypsin Proteins 0.000 description 6
- 229960002376 chymotrypsin Drugs 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- -1 4-substituted phenol Chemical class 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 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
- 230000014759 maintenance of location Effects 0.000 description 3
- VDLWTJCSPSUGOA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)CCCC2=C1 VDLWTJCSPSUGOA-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 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
- TWADEBCIPVNACR-ZDUSSCGKSA-N (2s)-2-(n-(4-methylphenyl)sulfonylanilino)propanoic acid Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N([C@@H](C)C(O)=O)C1=CC=CC=C1 TWADEBCIPVNACR-ZDUSSCGKSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- SKAWDTAMLOJQNK-UHFFFAOYSA-N 2-acetamido-3-(4-hydroxyphenyl)propanoic acid ethyl ester Chemical compound CCOC(=O)C(NC(C)=O)CC1=CC=C(O)C=C1 SKAWDTAMLOJQNK-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 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
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 206010060891 General symptom Diseases 0.000 description 1
- 208000016222 Pancreatic disease Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 230000005856 abnormality Effects 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000010410 layer 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- BVNMUHYZMQDZPJ-UHFFFAOYSA-N methanesulfonic acid;[4-(4-propan-2-ylpiperazine-1-carbonyl)phenyl] 1,2,3,4-tetrahydronaphthalene-1-carboxylate Chemical compound CS(O)(=O)=O.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1OC(=O)C1C2=CC=CC=C2CCC1 BVNMUHYZMQDZPJ-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 208000024691 pancreas disease Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57109192A JPS58225080A (ja) | 1982-06-25 | 1982-06-25 | ベンゾイルピペラジン誘導体 |
| AU15931/83A AU545463B2 (en) | 1982-06-25 | 1983-06-20 | Benzoyl piperacine esters |
| AT83303583T ATE28868T1 (de) | 1982-06-25 | 1983-06-22 | Benzoylpiperazinester und verfahren zu ihrer herstellung. |
| EP83303583A EP0098713B1 (en) | 1982-06-25 | 1983-06-22 | Benzoylpiperazine esters and a process for their production |
| DE8383303583T DE3372966D1 (en) | 1982-06-25 | 1983-06-22 | Benzoylpiperazine esters and a process for their production |
| ES523561A ES523561A0 (es) | 1982-06-25 | 1983-06-23 | Proceso para producir un ester de benzoilpiperazina. |
| CA000431034A CA1210005A (en) | 1982-06-25 | 1983-06-23 | Benzoylpiperazine esters and a process for their production |
| DK290583A DK158983C (da) | 1982-06-25 | 1983-06-23 | Analogifremgangsmaade til fremstilling af benzoylpiperazinestre eller syreadditionssalte deraf |
| ZA834600A ZA834600B (en) | 1982-06-25 | 1983-06-23 | Benzoylpiperazine esters and a process for their production |
| KR1019830002868A KR900003278B1 (ko) | 1982-06-25 | 1983-06-25 | 벤조일 피페라진 에스테르의 제조방법 |
| US06/796,525 US4898876A (en) | 1982-06-25 | 1985-11-12 | Benzoylpiperazine esters and a process for their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57109192A JPS58225080A (ja) | 1982-06-25 | 1982-06-25 | ベンゾイルピペラジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58225080A JPS58225080A (ja) | 1983-12-27 |
| JPH0339063B2 true JPH0339063B2 (no) | 1991-06-12 |
Family
ID=14503961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57109192A Granted JPS58225080A (ja) | 1982-06-25 | 1982-06-25 | ベンゾイルピペラジン誘導体 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS58225080A (no) |
| ZA (1) | ZA834600B (no) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59222484A (ja) * | 1983-06-02 | 1984-12-14 | Kowa Co | テトラヒドロナフチルカルボン酸フエニルエステル誘導体 |
| JPS608225A (ja) * | 1983-06-29 | 1985-01-17 | Kowa Co | 腸管吸収医薬組成物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56158737A (en) * | 1980-05-07 | 1981-12-07 | Kowa Co | Phenyl ester |
-
1982
- 1982-06-25 JP JP57109192A patent/JPS58225080A/ja active Granted
-
1983
- 1983-06-23 ZA ZA834600A patent/ZA834600B/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56158737A (en) * | 1980-05-07 | 1981-12-07 | Kowa Co | Phenyl ester |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA834600B (en) | 1984-08-29 |
| JPS58225080A (ja) | 1983-12-27 |
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