DE1518222A1 - Phenylalkylaminoguanidine - Google Patents
PhenylalkylaminoguanidineInfo
- Publication number
- DE1518222A1 DE1518222A1 DE19651518222 DE1518222A DE1518222A1 DE 1518222 A1 DE1518222 A1 DE 1518222A1 DE 19651518222 DE19651518222 DE 19651518222 DE 1518222 A DE1518222 A DE 1518222A DE 1518222 A1 DE1518222 A1 DE 1518222A1
- Authority
- DE
- Germany
- Prior art keywords
- acid addition
- addition salts
- derivative according
- formula
- ethylaminoguanidine
- 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.)
- Pending
Links
- 239000002253 acid Substances 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 230000001077 hypotensive effect Effects 0.000 claims description 6
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical class NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 208000001953 Hypotension Diseases 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 208000021822 hypotensive Diseases 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000002357 guanidines Chemical class 0.000 claims 7
- DVRMUBTVBPZZAT-UHFFFAOYSA-N 2-(ethylamino)guanidine Chemical compound CCNN=C(N)N DVRMUBTVBPZZAT-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 2
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 claims 2
- QUWILARGNKEHLL-UHFFFAOYSA-N 2-(3-phenylpropylamino)guanidine Chemical compound NC(N)=NNCCCC1=CC=CC=C1 QUWILARGNKEHLL-UHFFFAOYSA-N 0.000 claims 1
- DZRRFXIGJMIHGM-UHFFFAOYSA-N 2-(propylamino)guanidine Chemical compound CCCNN=C(N)N DZRRFXIGJMIHGM-UHFFFAOYSA-N 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 229910017604 nitric acid Inorganic materials 0.000 description 25
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- -1 with barium nitrate Chemical class 0.000 description 4
- PMGFHEJUUBDCLU-UHFFFAOYSA-N 2-aminoguanidine;nitric acid Chemical compound O[N+]([O-])=O.NN=C(N)N PMGFHEJUUBDCLU-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229960002748 norepinephrine Drugs 0.000 description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002889 sympathetic effect Effects 0.000 description 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- BZZXQZOBAUXLHZ-UHFFFAOYSA-N (c-methylsulfanylcarbonimidoyl)azanium;sulfate Chemical compound CSC(N)=N.CSC(N)=N.OS(O)(=O)=O BZZXQZOBAUXLHZ-UHFFFAOYSA-N 0.000 description 1
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 description 1
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 1
- ZIXIIJQSFSAZOL-UHFFFAOYSA-N 2-(cinnamylideneamino)guanidine Chemical compound NC(N)=NN=CC=CC1=CC=CC=C1 ZIXIIJQSFSAZOL-UHFFFAOYSA-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
- LZVRTEKMCCIWRU-UHFFFAOYSA-N 3-(2-methylphenyl)propan-1-ol Chemical compound CC1=CC=CC=C1CCCO LZVRTEKMCCIWRU-UHFFFAOYSA-N 0.000 description 1
- CIHMXRXLWPQFTH-UHFFFAOYSA-N 3-(2-methylphenyl)propanal Chemical compound CC1=CC=CC=C1CCC=O CIHMXRXLWPQFTH-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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 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
- 206010012735 Diarrhoea Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 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
- XWROSHJVVFETLV-UHFFFAOYSA-N [B+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O Chemical compound [B+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XWROSHJVVFETLV-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229960003602 guanethidine Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 210000000826 nictitating membrane Anatomy 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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 |
|---|---|---|---|
| CH585464A CH448057A (de) | 1964-05-05 | 1964-05-05 | Verfahren zur Herstellung von Phenylalkylaminoguanidinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1518222A1 true DE1518222A1 (de) | 1969-06-12 |
Family
ID=4300408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651518222 Pending DE1518222A1 (de) | 1964-05-05 | 1965-04-27 | Phenylalkylaminoguanidine |
Country Status (15)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3445339A1 (de) * | 1983-12-12 | 1985-06-13 | Biogál Gyógyszergyár, Debrecen | 3,3-disubstituierte 1-(phenylamino)-guanidinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0325936A3 (en) * | 1988-01-16 | 1990-01-17 | Ono Pharmaceutical Co., Ltd. | Aminoguanidine derivatives and inhibitory agents on maillard reaction containing them as active ingredients |
| WO1998023565A3 (en) * | 1996-11-26 | 1998-07-30 | Dimensional Pharm Inc | Aminoguanidines and alkoxyguanidines as protease inhibitors |
| US6635637B2 (en) | 2000-08-04 | 2003-10-21 | Dimensional Pharmaceuticals, Inc. | Cyclic oxyguanidine protease inhibitors |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR200F (enrdf_load_stackoverflow) * | 1965-11-15 | |||
| US3541218A (en) * | 1969-06-18 | 1970-11-17 | Lilly Co Eli | Omicron-fluorobenzylaminoguanidine for diabetes |
| JPS5051717U (enrdf_load_stackoverflow) * | 1973-09-06 | 1975-05-19 | ||
| JPS5391735U (enrdf_load_stackoverflow) * | 1976-12-27 | 1978-07-27 | ||
| JPS54121027U (enrdf_load_stackoverflow) * | 1978-02-13 | 1979-08-24 | ||
| JPS5625170A (en) * | 1979-06-01 | 1981-03-10 | Wellcome Found | Triazine derivative |
| IL60201A (en) * | 1979-06-01 | 1984-05-31 | Wellcome Found | 3-amino-6-(substituted)phenyl-1,2,4-triazine derivatives,their preparation and pharmaceutical compositions containing them |
| FR2549049B1 (fr) * | 1983-07-13 | 1986-06-20 | Chauvin Blache Lab | Nouvelles amidines, leur procede de preparation et leur application therapeutique |
| CA2250426C (en) * | 1996-03-29 | 2006-05-02 | 3-Dimensional Pharmaceuticals, Inc. | Amidinohydrazones as protease inhibitors |
-
0
- BE BE663481D patent/BE663481A/xx unknown
-
1964
- 1964-05-05 CH CH801766A patent/CH491873A/de not_active IP Right Cessation
- 1964-05-05 CH CH801666A patent/CH511216A/de not_active IP Right Cessation
- 1964-05-05 CH CH585464A patent/CH448057A/de unknown
-
1965
- 1965-04-26 SE SE5414/65A patent/SE317057B/xx unknown
- 1965-04-26 AT AT806366A patent/AT255434B/de active
- 1965-04-26 AT AT806266A patent/AT255433B/de active
- 1965-04-26 SE SE6816331A patent/SE371640B/xx unknown
- 1965-04-26 AT AT381265A patent/AT255432B/de active
- 1965-04-27 DE DE19651518222 patent/DE1518222A1/de active Pending
- 1965-04-28 IL IL23443A patent/IL23443A/xx unknown
- 1965-04-29 ES ES0312384A patent/ES312384A1/es not_active Expired
- 1965-05-03 DK DK224365AA patent/DK107288C/da active
- 1965-05-03 GB GB18547/65A patent/GB1096348A/en not_active Expired
- 1965-05-04 NL NL6505684A patent/NL6505684A/xx unknown
- 1965-05-04 CS CS6249A patent/CS151461B2/cs unknown
- 1965-05-04 FI FI1086/65A patent/FI42316B/fi active
- 1965-05-05 FR FR15815A patent/FR4399M/fr not_active Expired
- 1965-05-05 BR BR169419/65A patent/BR6569419D0/pt unknown
- 1965-05-06 JP JP40026185A patent/JPS4842627B1/ja active Pending
-
1966
- 1966-04-28 DK DK218666AA patent/DK111887B/da unknown
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3445339A1 (de) * | 1983-12-12 | 1985-06-13 | Biogál Gyógyszergyár, Debrecen | 3,3-disubstituierte 1-(phenylamino)-guanidinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0325936A3 (en) * | 1988-01-16 | 1990-01-17 | Ono Pharmaceutical Co., Ltd. | Aminoguanidine derivatives and inhibitory agents on maillard reaction containing them as active ingredients |
| WO1998023565A3 (en) * | 1996-11-26 | 1998-07-30 | Dimensional Pharm Inc | Aminoguanidines and alkoxyguanidines as protease inhibitors |
| US6235778B1 (en) | 1996-11-26 | 2001-05-22 | 3-Dimensional Pharmaceuticals, Inc. | Aminoguanidines and alkoxyguanidines as protease inhibitors |
| US6518310B2 (en) | 1996-11-26 | 2003-02-11 | 3-Dimensional Pharmaceuticals, Inc. | Aminoguanidines and alkoxyguanidines as protease inhibitors |
| US6638931B1 (en) | 1996-11-26 | 2003-10-28 | 3-Dimensional Pharmaceuticals, Inc. | Aminoguanidines and alkoxyguanidines as protease inhibitors |
| US6706765B2 (en) | 1996-11-26 | 2004-03-16 | 3-Dimensional Pharmaceuticals, Inc. | Aminoguanidines and alkoxyguanidines as protease inhibitors |
| US6730783B2 (en) | 1996-11-26 | 2004-05-04 | 3-Dimensional Pharmaceuticals, Inc. | Process for preparing aminoguanidines and alkoxyguanidines as protease inhibitors |
| US6635637B2 (en) | 2000-08-04 | 2003-10-21 | Dimensional Pharmaceuticals, Inc. | Cyclic oxyguanidine protease inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| BR6569419D0 (pt) | 1973-08-02 |
| JPS4842627B1 (enrdf_load_stackoverflow) | 1973-12-13 |
| ES312384A1 (es) | 1966-03-01 |
| BE663481A (enrdf_load_stackoverflow) | |
| CH448057A (de) | 1967-12-15 |
| CH511216A (de) | 1971-08-15 |
| GB1096348A (en) | 1967-12-29 |
| DK107288C (da) | 1967-05-16 |
| AT255432B (de) | 1967-07-10 |
| DK111887B (da) | 1968-10-21 |
| CS151461B2 (enrdf_load_stackoverflow) | 1973-10-19 |
| AT255434B (de) | 1967-07-10 |
| SE317057B (enrdf_load_stackoverflow) | 1969-11-10 |
| SE371640B (enrdf_load_stackoverflow) | 1974-11-25 |
| NL6505684A (enrdf_load_stackoverflow) | 1965-11-08 |
| AT255433B (de) | 1967-07-10 |
| FR4399M (enrdf_load_stackoverflow) | 1966-09-05 |
| FI42316B (enrdf_load_stackoverflow) | 1970-03-31 |
| CH491873A (de) | 1970-06-15 |
| IL23443A (en) | 1968-09-26 |
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