DE2831457C2 - - Google Patents
Info
- Publication number
- DE2831457C2 DE2831457C2 DE2831457A DE2831457A DE2831457C2 DE 2831457 C2 DE2831457 C2 DE 2831457C2 DE 2831457 A DE2831457 A DE 2831457A DE 2831457 A DE2831457 A DE 2831457A DE 2831457 C2 DE2831457 C2 DE 2831457C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- benzamidine
- pharmaceutically acceptable
- addition salts
- compounds
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 2
- BOJVHVNSFYVHNM-UHFFFAOYSA-N n'-(3-phenyl-1,2,4-oxadiazol-5-yl)-3-(trifluoromethyl)benzenecarboximidamide Chemical compound FC(F)(F)C1=CC=CC(C(=N)NC=2ON=C(N=2)C=2C=CC=CC=2)=C1 BOJVHVNSFYVHNM-UHFFFAOYSA-N 0.000 claims description 2
- JEWFJQWVHWGHOQ-UHFFFAOYSA-N n'-cyanobenzenecarboximidamide Chemical compound N#CN=C(N)C1=CC=CC=C1 JEWFJQWVHWGHOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- SLQNOMTYBAWNTG-UHFFFAOYSA-N 4-chloro-n'-(3-phenyl-1,2,4-oxadiazol-5-yl)benzenecarboximidamide Chemical compound C1=CC(Cl)=CC=C1C(=N)NC1=NC(C=2C=CC=CC=2)=NO1 SLQNOMTYBAWNTG-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- DOMPVUUMLACEKV-UHFFFAOYSA-N n'-(3-phenyl-1,2,4-oxadiazol-5-yl)benzenecarboximidamide Chemical compound C=1C=CC=CC=1C(=N)NC(ON=1)=NC=1C1=CC=CC=C1 DOMPVUUMLACEKV-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 229960001138 acetylsalicylic acid Drugs 0.000 description 8
- 231100000397 ulcer Toxicity 0.000 description 8
- 108010093965 Polymyxin B Proteins 0.000 description 7
- 229920000024 polymyxin B Polymers 0.000 description 7
- 229960005266 polymyxin b Drugs 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229960002895 phenylbutazone Drugs 0.000 description 6
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 6
- BQENDLAVTKRQMS-SBBGFIFASA-L Carbenoxolone sodium Chemical compound [Na+].[Na+].C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C([O-])=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](OC(=O)CCC([O-])=O)C1(C)C BQENDLAVTKRQMS-SBBGFIFASA-L 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 229960000530 carbenoxolone Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000028327 secretion Effects 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 102000015728 Mucins Human genes 0.000 description 4
- 108010063954 Mucins Proteins 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229940051875 mucins Drugs 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
- -1 N- (1,2,4-oxadiazol-5-yl) benzamidine derivatives Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 230000036269 ulceration Effects 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-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
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 210000001156 gastric mucosa Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 210000003097 mucus Anatomy 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DUJSBRSLDRKKKR-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-(trichloromethyl)-2h-oxadiazole Chemical compound C1=CC(Cl)=CC=C1N1C=C(C(Cl)(Cl)Cl)ON1 DUJSBRSLDRKKKR-UHFFFAOYSA-N 0.000 description 1
- JRWQLKZLTWPEBO-UHFFFAOYSA-N 3-(trifluoromethyl)benzenecarboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC=CC(C(F)(F)F)=C1 JRWQLKZLTWPEBO-UHFFFAOYSA-N 0.000 description 1
- IVAXNEHOHKGZEG-UHFFFAOYSA-N 5-chloro-3-phenyl-2h-oxadiazole Chemical compound N1OC(Cl)=CN1C1=CC=CC=C1 IVAXNEHOHKGZEG-UHFFFAOYSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- YHMSRTXLFOMTIY-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NOC(=N1)C1=C(C(=N)N)C=CC=C1 Chemical compound C1(=CC=CC=C1)C1=NOC(=N1)C1=C(C(=N)N)C=CC=C1 YHMSRTXLFOMTIY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 230000009704 beneficial physiological effect Effects 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000001744 histochemical effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100000053 low toxicity Toxicity 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000020925 non fasting Nutrition 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000003405 preventing effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000980 vagolytic effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or 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 to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or 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 to ring carbon atoms
- C07D261/14—Nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30523/77A GB1587945A (en) | 1977-07-20 | 1977-07-20 | Benzamidine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2831457A1 DE2831457A1 (de) | 1979-02-01 |
| DE2831457C2 true DE2831457C2 (en, 2012) | 1988-07-14 |
Family
ID=10309001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782831457 Granted DE2831457A1 (de) | 1977-07-20 | 1978-07-18 | Benzamidinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4246272A (en, 2012) |
| JP (1) | JPS5452077A (en, 2012) |
| AT (1) | AT359491B (en, 2012) |
| AU (1) | AU516005B2 (en, 2012) |
| BE (1) | BE868659A (en, 2012) |
| CA (1) | CA1095055A (en, 2012) |
| CH (1) | CH633000A5 (en, 2012) |
| DE (1) | DE2831457A1 (en, 2012) |
| ES (2) | ES471895A1 (en, 2012) |
| FR (1) | FR2398066A1 (en, 2012) |
| GB (1) | GB1587945A (en, 2012) |
| IL (1) | IL55088A (en, 2012) |
| IT (1) | IT1107844B (en, 2012) |
| NL (1) | NL7807679A (en, 2012) |
| SE (1) | SE447249B (en, 2012) |
| ZA (1) | ZA783830B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4636243A (en) * | 1980-09-16 | 1987-01-13 | Eli Lilly And Company | Benzamides, compositions and agricultural method |
| US4943634A (en) * | 1980-09-16 | 1990-07-24 | Eli Lilly And Company | N-heterocyclic benzamides |
| US4416683A (en) * | 1980-09-16 | 1983-11-22 | Eli Lilly And Company | Benzamides, compositions and agricultural method |
| US5086184A (en) * | 1980-09-16 | 1992-02-04 | Dowelanco | N-heterocyclic benzamides |
| IL165365A0 (en) | 2004-11-24 | 2006-01-15 | Q Core Ltd | Finger-type peristaltic pump |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1161896B (de) * | 1961-08-25 | 1964-01-30 | Hoechst Ag | Verfahren zur Herstellung von an der Amidogruppe mit Carbonsaeureester substituierten Carbonsaeureamidinen |
| DE1668851B2 (de) * | 1963-03-22 | 1973-05-03 | Amidine und verfahren zu ihrer herstellung | |
| GB1267009A (en, 2012) * | 1969-07-25 | 1972-03-15 | ||
| CA1039308A (en) * | 1974-10-02 | 1978-09-26 | James R. Mccarthy (Jr.) | N,n'-disubstituted halophenylacetamidines and n,n'-disubstituted benzamidines |
-
1977
- 1977-07-20 GB GB30523/77A patent/GB1587945A/en not_active Expired
-
1978
- 1978-06-30 BE BE189009A patent/BE868659A/xx not_active IP Right Cessation
- 1978-06-30 CH CH713578A patent/CH633000A5/fr not_active IP Right Cessation
- 1978-07-04 ZA ZA00783830A patent/ZA783830B/xx unknown
- 1978-07-04 FR FR7819905A patent/FR2398066A1/fr active Granted
- 1978-07-05 US US05/922,232 patent/US4246272A/en not_active Expired - Lifetime
- 1978-07-05 IL IL55088A patent/IL55088A/xx unknown
- 1978-07-10 AT AT497478A patent/AT359491B/de not_active IP Right Cessation
- 1978-07-10 CA CA307,055A patent/CA1095055A/en not_active Expired
- 1978-07-17 AU AU38088/78A patent/AU516005B2/en not_active Expired
- 1978-07-17 SE SE7807881A patent/SE447249B/sv not_active IP Right Cessation
- 1978-07-18 NL NL7807679A patent/NL7807679A/xx not_active Application Discontinuation
- 1978-07-18 DE DE19782831457 patent/DE2831457A1/de active Granted
- 1978-07-19 IT IT68716/78A patent/IT1107844B/it active
- 1978-07-19 JP JP8824178A patent/JPS5452077A/ja active Granted
- 1978-07-20 ES ES471895A patent/ES471895A1/es not_active Expired
-
1979
- 1979-03-30 ES ES479110A patent/ES479110A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5452077A (en) | 1979-04-24 |
| SE447249B (sv) | 1986-11-03 |
| FR2398066B1 (en, 2012) | 1980-09-26 |
| JPS6223751B2 (en, 2012) | 1987-05-25 |
| IL55088A (en) | 1981-07-31 |
| GB1587945A (en) | 1981-04-15 |
| DE2831457A1 (de) | 1979-02-01 |
| ES471895A1 (es) | 1979-10-01 |
| AU516005B2 (en) | 1981-05-14 |
| ZA783830B (en) | 1979-07-25 |
| AT359491B (de) | 1980-11-10 |
| FR2398066A1 (fr) | 1979-02-16 |
| SE7807881L (sv) | 1979-01-21 |
| ES479110A1 (es) | 1979-07-01 |
| US4246272A (en) | 1981-01-20 |
| IT1107844B (it) | 1985-12-02 |
| CA1095055A (en) | 1981-02-03 |
| IT7868716A0 (it) | 1978-07-19 |
| ATA497478A (de) | 1980-04-15 |
| AU3808878A (en) | 1980-01-17 |
| NL7807679A (nl) | 1979-01-23 |
| BE868659A (fr) | 1979-01-02 |
| CH633000A5 (fr) | 1982-11-15 |
| IL55088A0 (en) | 1978-09-29 |
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