HU209245B - Process for producing new cimetidine derivatives, as well as new gastric acid secretion inhibiting and gastrocytoprotective pharmaceuitcal compositions - Google Patents
Process for producing new cimetidine derivatives, as well as new gastric acid secretion inhibiting and gastrocytoprotective pharmaceuitcal compositions Download PDFInfo
- Publication number
- HU209245B HU209245B HU406791A HU406791A HU209245B HU 209245 B HU209245 B HU 209245B HU 406791 A HU406791 A HU 406791A HU 406791 A HU406791 A HU 406791A HU 209245 B HU209245 B HU 209245B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- cimetidine
- compound
- hydrogen
- new
- Prior art date
Links
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical class N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 title claims description 34
- 230000027119 gastric acid secretion Effects 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 9
- 239000000203 mixture Substances 0.000 title description 18
- 230000002401 inhibitory effect Effects 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 37
- 229960001380 cimetidine Drugs 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 230000005764 inhibitory process Effects 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052717 sulfur Chemical group 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 230000000694 effects Effects 0.000 description 18
- 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 12
- 239000004480 active ingredient Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- -1 5-methylimidazol-4-yl Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- RVMGXWBCQGAWBR-UHFFFAOYSA-N 4-oxo-1-benzopyran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC(=O)C2=C1 RVMGXWBCQGAWBR-UHFFFAOYSA-N 0.000 description 7
- 208000007107 Stomach Ulcer Diseases 0.000 description 7
- 201000005917 gastric ulcer Diseases 0.000 description 7
- AIDUVDSNSWBMJT-UHFFFAOYSA-N 4-oxothiochromene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC(=O)C2=C1 AIDUVDSNSWBMJT-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 208000025865 Ulcer Diseases 0.000 description 6
- 229960000905 indomethacin Drugs 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- ZPPVZUSDLLELAN-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonylprop-2-enoic acid Chemical compound OC(=O)C=CS(=O)(=O)C1=CC=C(Cl)C=C1 ZPPVZUSDLLELAN-UHFFFAOYSA-N 0.000 description 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 5
- 229960001138 acetylsalicylic acid Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 231100000397 ulcer Toxicity 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- 241000700159 Rattus Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000036269 ulceration Effects 0.000 description 2
- BJFWNTBQQWFCIK-UHFFFAOYSA-N 3-(benzenesulfonyl)prop-2-enoic acid Chemical compound OC(=O)C=CS(=O)(=O)C1=CC=CC=C1 BJFWNTBQQWFCIK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU406791A HU209245B (en) | 1991-12-20 | 1991-12-20 | Process for producing new cimetidine derivatives, as well as new gastric acid secretion inhibiting and gastrocytoprotective pharmaceuitcal compositions |
| PCT/HU1992/000059 WO1993012787A1 (en) | 1991-12-20 | 1992-12-18 | New pharmaceutical compositions inhibiting gastric acid secretion and exerting gastrocytoprotective effect |
| CN 92115369 CN1075255A (zh) | 1991-12-20 | 1992-12-19 | 抑制胃酸分泌并具有胃细胞保护作用的新的药物组合物 |
| TW81110294A TW232015B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-12-20 | 1992-12-21 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU406791A HU209245B (en) | 1991-12-20 | 1991-12-20 | Process for producing new cimetidine derivatives, as well as new gastric acid secretion inhibiting and gastrocytoprotective pharmaceuitcal compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU914067D0 HU914067D0 (en) | 1992-03-30 |
| HUT63955A HUT63955A (en) | 1993-11-29 |
| HU209245B true HU209245B (en) | 1994-04-28 |
Family
ID=10966768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU406791A HU209245B (en) | 1991-12-20 | 1991-12-20 | Process for producing new cimetidine derivatives, as well as new gastric acid secretion inhibiting and gastrocytoprotective pharmaceuitcal compositions |
Country Status (4)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000022532A (ko) * | 1996-06-27 | 2000-04-25 | 오노 야꾸힝 고교 가부시키가이샤 | 아릴(설파이드, 설폭시드 및 설폰)유도체 및 이를 활성 성분으로 함유하는 약물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040489A1 (en) * | 1980-05-17 | 1981-11-25 | FISONS plc | Mixtures, salts, packages and pharmaceutical compositions containing 5-(2-hydroxypropoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylic acid or a derivative thereof and an H2 receptor antagonist antihistamine |
| EP0156233A3 (en) * | 1984-03-19 | 1986-02-19 | Merck & Co. Inc. | Use of leukotriene antagonists for producing cytoprotective pharmaceutical compositions and process for producing cytoprotective pharmaceutical compositions |
| FI902400A0 (fi) * | 1988-09-14 | 1990-05-14 | Biota Scient Management | Kromonderivat. |
| HU203839B (en) * | 1989-07-14 | 1991-10-28 | Richter Gedeon Vegyeszet | Process for producing pharmaceutical composition containing acrylic acid derivatives |
-
1991
- 1991-12-20 HU HU406791A patent/HU209245B/hu not_active IP Right Cessation
-
1992
- 1992-12-18 WO PCT/HU1992/000059 patent/WO1993012787A1/en active Application Filing
- 1992-12-19 CN CN 92115369 patent/CN1075255A/zh active Pending
- 1992-12-21 TW TW81110294A patent/TW232015B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| HU914067D0 (en) | 1992-03-30 |
| TW232015B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-10-11 |
| WO1993012787A1 (en) | 1993-07-08 |
| CN1075255A (zh) | 1993-08-18 |
| HUT63955A (en) | 1993-11-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| UA43841C2 (uk) | Імідазопіридини та фармацевтична композиція на їх основі | |
| US4078063A (en) | Piperazinylpyridines | |
| CS208661B2 (en) | Method of making the n-/2-phenyl-2-hydroxyethyl/-1,1-dimethyl-3-phenylpropylamin derivatives | |
| JPS6229566A (ja) | 新規グアニジノメチル安息香酸誘導体 | |
| RU2043994C1 (ru) | Глутатионалкиловые эфиры окисленного типа и способ их получения | |
| US4087526A (en) | (3-Amino-5-substituted-6-fluoropyrazinoyl or pyrazamido)-guanidines and their derivatives bearing substituents on the guanidino nitrogens | |
| DE68911776T2 (de) | Konjugierte Oxybutenolide zur Behandlung von Ulcera. | |
| US4308207A (en) | Morphanthridine derivatives | |
| GB2045756A (en) | Hydroxy derivatives of 2- isopropylamino-pyrimidine | |
| HU195486B (en) | Process for preparing new pyridine derivatives | |
| US4461775A (en) | Hydroxythioether fatty acid derivatives | |
| US4233310A (en) | Antiarteriosclerotic N-(mercaptoacyl)-histidines | |
| DE69215482T2 (de) | 2,2'-Alkylendiindolderivate, Verfahren zu ihrer Herstellung, sie enthaltende Arzneimittel und deren Verwendung als Ulcustherapeutikum | |
| WO1989005799A1 (en) | Novel tetrahydropyridine derivatives, pharmaceutical compositions containing them and process for preparing same | |
| CA2433190C (en) | Amlodipine hemimaleate | |
| US4515806A (en) | Furan derivatives and addition salts thereof pharmaceutical compositions and the therapeutical applications thereof | |
| HU210154B (en) | Process for producing new famotidin-salts and pharmaceutical compositions of gastro-acid-secretion-inhibiting and gastro-citoprotective activity, containing them | |
| HU209245B (en) | Process for producing new cimetidine derivatives, as well as new gastric acid secretion inhibiting and gastrocytoprotective pharmaceuitcal compositions | |
| US4406900A (en) | Neuroleptic use of morphanthridines | |
| HU181947B (en) | Process for producing pyridyl-indol derivatives | |
| US4267181A (en) | Halogeno derivatives of isopropylamino pyrimidine and therapeutic use | |
| GB2054556A (en) | Preparation of hydroxy derivatives of 2-isopropylamino-pyrimidine | |
| JPS5943460B2 (ja) | ２−アミノ−６−ジアルキルアミノジヒドロピリジンの製造方法 | |
| US3917833A (en) | Amino-substituted benzocycloheptenones for inducing sleep | |
| JPH0154326B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |