JPH0231693B2 - - Google Patents
Info
- Publication number
- JPH0231693B2 JPH0231693B2 JP57113339A JP11333982A JPH0231693B2 JP H0231693 B2 JPH0231693 B2 JP H0231693B2 JP 57113339 A JP57113339 A JP 57113339A JP 11333982 A JP11333982 A JP 11333982A JP H0231693 B2 JPH0231693 B2 JP H0231693B2
- Authority
- JP
- Japan
- Prior art keywords
- insulin
- drug
- chymotrypsin inhibitor
- formula
- blood sugar
- 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
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 68
- 102000004877 Insulin Human genes 0.000 claims description 34
- 108090001061 Insulin Proteins 0.000 claims description 34
- 229940125396 insulin Drugs 0.000 claims description 34
- 239000003541 chymotrypsin inhibitor Substances 0.000 claims description 27
- 229940122644 Chymotrypsin inhibitor Drugs 0.000 claims description 25
- 101710137926 Chymotrypsin inhibitor Proteins 0.000 claims description 25
- 229940079593 drug Drugs 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 20
- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- -1 phenyl ester Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000008280 blood Substances 0.000 description 26
- 210000004369 blood Anatomy 0.000 description 26
- 238000000034 method Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 10
- 238000000691 measurement method Methods 0.000 description 10
- 210000001035 gastrointestinal tract Anatomy 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002753 trypsin inhibitor Substances 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 239000002702 enteric coating Substances 0.000 description 4
- 238000009505 enteric coating Methods 0.000 description 4
- 230000002218 hypoglycaemic effect Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 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 3
- 239000000829 suppository Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108090000317 Chymotrypsin Proteins 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 239000004366 Glucose oxidase Substances 0.000 description 2
- 108010015776 Glucose oxidase Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229940122618 Trypsin inhibitor Drugs 0.000 description 2
- 101710162629 Trypsin inhibitor Proteins 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000003472 antidiabetic agent Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229940105329 carboxymethylcellulose Drugs 0.000 description 2
- 229960002376 chymotrypsin Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229940116332 glucose oxidase Drugs 0.000 description 2
- 235000019420 glucose oxidase Nutrition 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- AKARIZHKZBLDNW-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)CCCC2=C1 AKARIZHKZBLDNW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- WJNRAOKRAWFGFS-UHFFFAOYSA-N 7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid Chemical compound C1CCC(C(O)=O)C2=CC(OC)=CC=C21 WJNRAOKRAWFGFS-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 101000621959 Daboia siamensis Kunitz-type serine protease inhibitor C10 Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- RPLMKCBNPADRQO-UHFFFAOYSA-N [4-(4-ethylpiperazine-1-carbonyl)phenyl] 1,2,3,4-tetrahydronaphthalene-1-carboxylate;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1CN(CC)CCN1C(=O)C(C=C1)=CC=C1OC(=O)C1C2=CC=CC=C2CCC1 RPLMKCBNPADRQO-UHFFFAOYSA-N 0.000 description 1
- XDMHRIXNMMSEIU-UHFFFAOYSA-N [4-(4-methylpiperazine-1-carbonyl)phenyl] 7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylate Chemical compound C12=CC(OC)=CC=C2CCCC1C(=O)OC(C=C1)=CC=C1C(=O)N1CCN(C)CC1 XDMHRIXNMMSEIU-UHFFFAOYSA-N 0.000 description 1
- HZADVQQWFAJFJX-UHFFFAOYSA-N [4-[4-[2-(dimethylamino)-2-oxoethyl]piperazine-1-carbonyl]phenyl] 1,2,3,4-tetrahydronaphthalene-1-carboxylate;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1CN(CC(=O)N(C)C)CCN1C(=O)C(C=C1)=CC=C1OC(=O)C1C2=CC=CC=C2CCC1 HZADVQQWFAJFJX-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 229940127003 anti-diabetic drug Drugs 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- FSEKIHNIDBATFG-UHFFFAOYSA-N camostat mesylate Chemical compound CS([O-])(=O)=O.C1=CC(CC(=O)OCC(=O)N(C)C)=CC=C1OC(=O)C1=CC=C([NH+]=C(N)N)C=C1 FSEKIHNIDBATFG-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229950009941 chloralose Drugs 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XWYHSKXLXUSUSJ-UHFFFAOYSA-N ethyl 2-[4-(4-hydroxybenzoyl)piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1C(=O)C1=CC=C(O)C=C1 XWYHSKXLXUSUSJ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000002350 laparotomy Methods 0.000 description 1
- GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 1
- 108010052968 leupeptin Proteins 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- XPLZPVIDWASNGU-UHFFFAOYSA-N methanesulfonic acid;[4-[4-(2-oxo-2-piperidin-1-ylethyl)piperazine-1-carbonyl]phenyl] 1,2,3,4-tetrahydronaphthalene-1-carboxylate Chemical compound CS(O)(=O)=O.C1CN(C(=O)C=2C=CC(OC(=O)C3C4=CC=CC=C4CCC3)=CC=2)CCN1CC(=O)N1CCCCC1 XPLZPVIDWASNGU-UHFFFAOYSA-N 0.000 description 1
- WXUVMQXIRSOLLW-UHFFFAOYSA-N methanesulfonic acid;[4-[4-[2-oxo-2-(propan-2-ylamino)ethyl]piperazine-1-carbonyl]phenyl] 1,2,3,4-tetrahydronaphthalene-1-carboxylate Chemical compound CS(O)(=O)=O.C1CN(CC(=O)NC(C)C)CCN1C(=O)C(C=C1)=CC=C1OC(=O)C1C2=CC=CC=C2CCC1 WXUVMQXIRSOLLW-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001631 vena cava inferior Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57113339A JPS595115A (ja) | 1982-06-30 | 1982-06-30 | 糖尿病治療用薬剤 |
EP82303902A EP0071433A1 (fr) | 1981-07-28 | 1982-07-23 | Médicament pour le traitement du diabète |
DK334282A DK334282A (da) | 1981-07-28 | 1982-07-27 | Medicinsk komposition samt fremgangsmaade og middel til dens fremstilling |
CA000408188A CA1174597A (fr) | 1981-07-28 | 1982-07-27 | Medicament pour le traitement du diabete |
AU86503/82A AU8650382A (en) | 1981-07-28 | 1982-07-28 | Synthetic phenyl ester chymotrypsin inhibitor to treat diabetes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57113339A JPS595115A (ja) | 1982-06-30 | 1982-06-30 | 糖尿病治療用薬剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS595115A JPS595115A (ja) | 1984-01-12 |
JPH0231693B2 true JPH0231693B2 (fr) | 1990-07-16 |
Family
ID=14609733
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57113339A Granted JPS595115A (ja) | 1981-07-28 | 1982-06-30 | 糖尿病治療用薬剤 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS595115A (fr) |
Families Citing this family (3)
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 |
JPS6253954A (ja) | 1985-09-02 | 1987-03-09 | Ajinomoto Co Inc | フエニルアラニン誘導体およびその用途 |
ES2618024T3 (es) | 2011-06-07 | 2017-06-20 | Ea Pharma Co., Ltd. | Derivado de éster de ácido carboxílico heterocíclico |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5315412A (en) * | 1976-07-27 | 1978-02-13 | Ono Pharmaceut Co Ltd | Suppository for diabetics |
JPS55149240A (en) * | 1979-05-09 | 1980-11-20 | Kowa Co | Hydroxybenzoic acid derivative and its acid addition salt |
JPS56158737A (en) * | 1980-05-07 | 1981-12-07 | Kowa Co | Phenyl ester |
-
1982
- 1982-06-30 JP JP57113339A patent/JPS595115A/ja active Granted
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5315412A (en) * | 1976-07-27 | 1978-02-13 | Ono Pharmaceut Co Ltd | Suppository for diabetics |
JPS55149240A (en) * | 1979-05-09 | 1980-11-20 | Kowa Co | Hydroxybenzoic acid derivative and its acid addition salt |
JPS56158737A (en) * | 1980-05-07 | 1981-12-07 | Kowa Co | Phenyl ester |
Also Published As
Publication number | Publication date |
---|---|
JPS595115A (ja) | 1984-01-12 |
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